US20170135994A9 - Nampt inhibitors - Google Patents
Nampt inhibitors Download PDFInfo
- Publication number
- US20170135994A9 US20170135994A9 US14/878,858 US201514878858A US2017135994A9 US 20170135994 A9 US20170135994 A9 US 20170135994A9 US 201514878858 A US201514878858 A US 201514878858A US 2017135994 A9 US2017135994 A9 US 2017135994A9
- Authority
- US
- United States
- Prior art keywords
- pyridin
- ylmethyl
- imidazo
- piperidin
- benzamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 108010064862 Nicotinamide phosphoribosyltransferase Proteins 0.000 title abstract description 28
- 239000003112 inhibitor Substances 0.000 title description 14
- 102100033223 Nicotinamide phosphoribosyltransferase Human genes 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 16
- 201000010099 disease Diseases 0.000 claims abstract description 13
- -1 3-{4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidin-1-yl}-3-oxopropyl Chemical group 0.000 claims description 99
- 150000003839 salts Chemical class 0.000 claims description 34
- 206010028980 Neoplasm Diseases 0.000 claims description 14
- 201000011510 cancer Diseases 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 12
- 208000030507 AIDS Diseases 0.000 claims description 10
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 10
- 208000023275 Autoimmune disease Diseases 0.000 claims description 7
- 206010012601 diabetes mellitus Diseases 0.000 claims description 7
- 230000002757 inflammatory effect Effects 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 6
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 5
- 206010003591 Ataxia Diseases 0.000 claims description 5
- 206010006895 Cachexia Diseases 0.000 claims description 5
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 5
- 206010048768 Dermatosis Diseases 0.000 claims description 5
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 5
- 208000017604 Hodgkin disease Diseases 0.000 claims description 5
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 239000004201 L-cysteine Substances 0.000 claims description 5
- 206010025323 Lymphomas Diseases 0.000 claims description 5
- 208000001132 Osteoporosis Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 5
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 5
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 5
- 208000036142 Viral infection Diseases 0.000 claims description 5
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 5
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 201000008937 atopic dermatitis Diseases 0.000 claims description 5
- 210000000481 breast Anatomy 0.000 claims description 5
- 210000003169 central nervous system Anatomy 0.000 claims description 5
- 210000003679 cervix uteri Anatomy 0.000 claims description 5
- 210000001072 colon Anatomy 0.000 claims description 5
- 230000003176 fibrotic effect Effects 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 208000032839 leukemia Diseases 0.000 claims description 5
- 210000004072 lung Anatomy 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 210000000056 organ Anatomy 0.000 claims description 5
- 201000008482 osteoarthritis Diseases 0.000 claims description 5
- 210000001672 ovary Anatomy 0.000 claims description 5
- 210000000496 pancreas Anatomy 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 210000002307 prostate Anatomy 0.000 claims description 5
- 208000037803 restenosis Diseases 0.000 claims description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- 210000003491 skin Anatomy 0.000 claims description 5
- 230000037380 skin damage Effects 0.000 claims description 5
- 208000017520 skin disease Diseases 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 210000001519 tissue Anatomy 0.000 claims description 5
- 230000017423 tissue regeneration Effects 0.000 claims description 5
- 210000003932 urinary bladder Anatomy 0.000 claims description 5
- 230000009385 viral infection Effects 0.000 claims description 5
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 4
- MGASOEMIIUPMCU-UHFFFAOYSA-N 5-[1-[[1-[3-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]propanoyl]-4-methylpiperidin-4-yl]methyl]pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=C(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C=NN1CC1(C)CCN(C(=O)CCOCCOCCOCCOCCN)CC1 MGASOEMIIUPMCU-UHFFFAOYSA-N 0.000 claims description 3
- DRWTYKYVRHAWNF-UHFFFAOYSA-N 5-[1-[[3,5-dimethyl-7-[2-(methylamino)ethoxy]-1-adamantyl]methyl]-5-methylpyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(C=N1)=C(C)N1CC1(C2)CC(C)(C3)CC2(C)CC3(OCCNC)C1 DRWTYKYVRHAWNF-UHFFFAOYSA-N 0.000 claims description 3
- SFSLVQKEHGAOGG-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[[4-methyl-1-(2-piperazin-1-ylethyl)piperidin-4-yl]methyl]pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1CC(C)(CN2N=CC(=C2)C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1CCN1CCNCC1 SFSLVQKEHGAOGG-UHFFFAOYSA-N 0.000 claims description 3
- 208000000277 Splenic Neoplasms Diseases 0.000 claims description 2
- 201000002471 spleen cancer Diseases 0.000 claims description 2
- 102000015532 Nicotinamide phosphoribosyltransferase Human genes 0.000 abstract description 26
- 230000000694 effects Effects 0.000 abstract description 9
- 239000000203 mixture Substances 0.000 abstract description 6
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 729
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 729
- 125000001424 substituent group Chemical group 0.000 description 394
- 125000000217 alkyl group Chemical group 0.000 description 355
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 352
- 239000000460 chlorine Substances 0.000 description 346
- 229910052801 chlorine Inorganic materials 0.000 description 339
- 229910052740 iodine Inorganic materials 0.000 description 339
- 229910052794 bromium Inorganic materials 0.000 description 338
- 229910052731 fluorine Inorganic materials 0.000 description 327
- 229910052739 hydrogen Inorganic materials 0.000 description 283
- 125000003118 aryl group Chemical group 0.000 description 273
- 125000000623 heterocyclic group Chemical group 0.000 description 265
- 125000000753 cycloalkyl group Chemical group 0.000 description 226
- 125000003342 alkenyl group Chemical group 0.000 description 192
- 125000000304 alkynyl group Chemical group 0.000 description 174
- 239000001257 hydrogen Substances 0.000 description 146
- 125000000392 cycloalkenyl group Chemical group 0.000 description 141
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 140
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 140
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 124
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 112
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 111
- 229910006074 SO2NH2 Inorganic materials 0.000 description 110
- OTXBWGUYZNKPMG-UHFFFAOYSA-N isofulminic acid Chemical compound O[N+]#[C-] OTXBWGUYZNKPMG-UHFFFAOYSA-N 0.000 description 110
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 107
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 65
- 125000003545 alkoxy group Chemical group 0.000 description 57
- 125000001188 haloalkyl group Chemical group 0.000 description 56
- 150000002431 hydrogen Chemical group 0.000 description 31
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 30
- 125000001544 thienyl group Chemical group 0.000 description 30
- 125000000335 thiazolyl group Chemical group 0.000 description 28
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 15
- 125000006413 ring segment Chemical group 0.000 description 15
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 13
- 125000004429 atom Chemical group 0.000 description 13
- 125000004452 carbocyclyl group Chemical group 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 125000002541 furyl group Chemical group 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 125000003367 polycyclic group Chemical group 0.000 description 8
- 229940079593 drug Drugs 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 229950006238 nadide Drugs 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- BAWFJGJZGIEFAR-NNYOXOHSSA-O NAD(+) Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-O 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 108091000080 Phosphotransferase Proteins 0.000 description 3
- 210000001744 T-lymphocyte Anatomy 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229910052805 deuterium Inorganic materials 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 102000020233 phosphotransferase Human genes 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 230000019491 signal transduction Effects 0.000 description 3
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 2
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- AUDBJBDAORWTQK-UHFFFAOYSA-N 4-(1-benzoylpiperidin-4-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CC=C1 AUDBJBDAORWTQK-UHFFFAOYSA-N 0.000 description 2
- NHIKGUGEBFJAMF-UHFFFAOYSA-N 4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 NHIKGUGEBFJAMF-UHFFFAOYSA-N 0.000 description 2
- ZWGFJCNOMWRROL-UHFFFAOYSA-N 4-[1-(2-acetylbenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound CC(=O)C1=CC=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 ZWGFJCNOMWRROL-UHFFFAOYSA-N 0.000 description 2
- GJVQMJPDRJMWKJ-UHFFFAOYSA-N 4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound ClC1=CC(C#N)=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 GJVQMJPDRJMWKJ-UHFFFAOYSA-N 0.000 description 2
- KQYFFOCIDMBKPR-UHFFFAOYSA-N 4-[1-(2-chlorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound ClC1=CC=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 KQYFFOCIDMBKPR-UHFFFAOYSA-N 0.000 description 2
- WECVQSLVXULPGD-UHFFFAOYSA-N 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 WECVQSLVXULPGD-UHFFFAOYSA-N 0.000 description 2
- LNVYDMFYZLRLGY-UHFFFAOYSA-N 4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound CC1=CC=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1O LNVYDMFYZLRLGY-UHFFFAOYSA-N 0.000 description 2
- JYIGLALYGWBIDJ-UHFFFAOYSA-N 4-[1-(3,5-dimethoxybenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound COC1=CC(OC)=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 JYIGLALYGWBIDJ-UHFFFAOYSA-N 0.000 description 2
- DURLVYXFKSYVDN-UHFFFAOYSA-N 4-[1-(3-chlorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound ClC1=CC=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 DURLVYXFKSYVDN-UHFFFAOYSA-N 0.000 description 2
- QGEMAFQOZBFDNX-UHFFFAOYSA-N 4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=C(C#N)C(F)=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 QGEMAFQOZBFDNX-UHFFFAOYSA-N 0.000 description 2
- WEQRQSJTJHCYCB-UHFFFAOYSA-N 4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC(C#N)=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 WEQRQSJTJHCYCB-UHFFFAOYSA-N 0.000 description 2
- RAKCJVYPIPHBML-UHFFFAOYSA-N 4-[1-(3-fluoro-4-methoxybenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=C(F)C(OC)=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 RAKCJVYPIPHBML-UHFFFAOYSA-N 0.000 description 2
- LVTSHABAQNQNKL-UHFFFAOYSA-N 4-[1-(3-fluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 LVTSHABAQNQNKL-UHFFFAOYSA-N 0.000 description 2
- AHWAPGOJDWMJOM-UHFFFAOYSA-N 4-[1-(4-chlorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 AHWAPGOJDWMJOM-UHFFFAOYSA-N 0.000 description 2
- QHZZXDCJKNXJKZ-UHFFFAOYSA-N 4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC(C#N)=CC(F)=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 QHZZXDCJKNXJKZ-UHFFFAOYSA-N 0.000 description 2
- BXZIFIQDOIQMDA-UHFFFAOYSA-N 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CC(F)=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 BXZIFIQDOIQMDA-UHFFFAOYSA-N 0.000 description 2
- JZGAYGDGJKORIZ-UHFFFAOYSA-N 4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC=C(C#N)C=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 JZGAYGDGJKORIZ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- 230000008484 agonism Effects 0.000 description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 230000000155 isotopic effect Effects 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- WVOCSBWMQZYSAJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxy-6-methylbenzoyl)piperidin-4-yl]benzamide Chemical compound COC1=CC=CC(C)=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 WVOCSBWMQZYSAJ-UHFFFAOYSA-N 0.000 description 2
- PROLTIQGZSCCAS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)piperidin-4-yl]benzamide Chemical compound CC1=CC=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 PROLTIQGZSCCAS-UHFFFAOYSA-N 0.000 description 2
- YTRFCOCLOUFPHX-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[2-(methoxymethyl)benzoyl]piperidin-4-yl]benzamide Chemical compound COCC1=CC=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 YTRFCOCLOUFPHX-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- YETODIXQMRZKEG-RITPCOANSA-N (3ar,6ar)-1,2,3,3a,4,5,6,6a-octahydropyrrolo[2,3-c]pyrrole Chemical group C1NC[C@@H]2NCC[C@@H]21 YETODIXQMRZKEG-RITPCOANSA-N 0.000 description 1
- DLUDAUJQMXTXGQ-RQJHMYQMSA-N (3ar,6ar)-5-methyl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical group C1CN[C@H]2CN(C)C[C@H]21 DLUDAUJQMXTXGQ-RQJHMYQMSA-N 0.000 description 1
- YQURLNGUWNDBIR-KNVOCYPGSA-N (3as,6ar)-5-methyl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical group C1NC[C@@H]2CN(C)C[C@@H]21 YQURLNGUWNDBIR-KNVOCYPGSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- RQPDLNSKAAOHTF-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydro-1,5-naphthyridine Chemical group C1CCNC2CCCNC21 RQPDLNSKAAOHTF-UHFFFAOYSA-N 0.000 description 1
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- 125000000196 1,4-pentadienyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])=C([H])[H] 0.000 description 1
- RTSYDSYMEPRCNR-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-[4-(1-propylpyrazol-4-yl)phenyl]urea Chemical compound C1=NN(CCC)C=C1C(C=C1)=CC=C1NC(=O)NCC1=CN2C=CN=C2C=C1 RTSYDSYMEPRCNR-UHFFFAOYSA-N 0.000 description 1
- ATCNGCFGSWFBIH-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-[4-[1-(2-methylpropyl)pyrazol-4-yl]phenyl]urea Chemical compound C1=NN(CC(C)C)C=C1C(C=C1)=CC=C1NC(=O)NCC1=CN2C=CN=C2C=C1 ATCNGCFGSWFBIH-UHFFFAOYSA-N 0.000 description 1
- FSCLDFVJMDDQOR-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-phenoxyphenyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 FSCLDFVJMDDQOR-UHFFFAOYSA-N 0.000 description 1
- NHIXGKAENXAJRB-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-propylpyrazol-4-yl)phenyl]urea Chemical compound C1=NN(CCC)C=C1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 NHIXGKAENXAJRB-UHFFFAOYSA-N 0.000 description 1
- TYKKAZYLEZUYHK-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[(2-phenylphenyl)sulfonylamino]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 TYKKAZYLEZUYHK-UHFFFAOYSA-N 0.000 description 1
- DAIFRZDISWXVLH-HXUWFJFHSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[(3r)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxyphenyl]urea Chemical compound C1N(C(=O)C(C)C)CC[C@H]1OC(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 DAIFRZDISWXVLH-HXUWFJFHSA-N 0.000 description 1
- JZIJOFPRMAMNSS-JOCHJYFZSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[(3r)-1-(oxane-4-carbonyl)pyrrolidin-3-yl]oxyphenyl]urea Chemical compound C([C@H](C1)OC2=CC=C(C=C2)NC(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)C1CCOCC1 JZIJOFPRMAMNSS-JOCHJYFZSA-N 0.000 description 1
- XJJNCFOQTJQELV-BDPMCISCSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[(3r)-1-(oxolane-3-carbonyl)pyrrolidin-3-yl]oxyphenyl]urea Chemical compound C([C@H](C1)OC2=CC=C(C=C2)NC(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)C1CCOC1 XJJNCFOQTJQELV-BDPMCISCSA-N 0.000 description 1
- ZPTBKHYOECLLEW-NHCUHLMSSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[(3r)-1-[(2r)-oxolane-2-carbonyl]pyrrolidin-3-yl]oxyphenyl]urea Chemical compound C([C@H](C1)OC2=CC=C(C=C2)NC(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)[C@H]1CCCO1 ZPTBKHYOECLLEW-NHCUHLMSSA-N 0.000 description 1
- VWODPQJKFSSIEP-LAUBAEHRSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[(3r)-1-[(2s)-2-methylbutanoyl]pyrrolidin-3-yl]oxyphenyl]urea Chemical compound C1N(C(=O)[C@@H](C)CC)CC[C@H]1OC(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 VWODPQJKFSSIEP-LAUBAEHRSA-N 0.000 description 1
- ZPTBKHYOECLLEW-RTWAWAEBSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[(3r)-1-[(2s)-oxolane-2-carbonyl]pyrrolidin-3-yl]oxyphenyl]urea Chemical compound C([C@H](C1)OC2=CC=C(C=C2)NC(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)[C@@H]1CCCO1 ZPTBKHYOECLLEW-RTWAWAEBSA-N 0.000 description 1
- CNRBDZMSJFKSPI-HSZRJFAPSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[(3r)-1-[2-(oxan-4-yl)acetyl]pyrrolidin-3-yl]oxyphenyl]urea Chemical compound C([C@H](C1)OC2=CC=C(C=C2)NC(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)CC1CCOCC1 CNRBDZMSJFKSPI-HSZRJFAPSA-N 0.000 description 1
- MCYBKQVVXQFEHI-HSZRJFAPSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[(3r)-1-[4-(trifluoromethyl)benzoyl]pyrrolidin-3-yl]oxyphenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)N1C[C@H](OC=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 MCYBKQVVXQFEHI-HSZRJFAPSA-N 0.000 description 1
- WDNWWXUZOWXBPX-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(1-methyl-4,5,6,7-tetrahydroindazole-3-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1CCCC2=C1C(C(=O)N1CCC(CC1)C=1C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=1)=NN2C WDNWWXUZOWXBPX-UHFFFAOYSA-N 0.000 description 1
- QKYGHYKETZAFQF-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(1-methyl-5-propylpyrazole-4-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=NN(C)C(CCC)=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 QKYGHYKETZAFQF-UHFFFAOYSA-N 0.000 description 1
- GNVCYRLNRKZVMV-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(1-methylindazole-4-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=C2C=NN(C)C2=CC=C1 GNVCYRLNRKZVMV-UHFFFAOYSA-N 0.000 description 1
- ACYLSJFPRSSHIZ-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(1-methylindazole-6-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=C2C=NN(C)C2=C1 ACYLSJFPRSSHIZ-UHFFFAOYSA-N 0.000 description 1
- OOEMPICOPPHXIM-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(1-methylindazole-7-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=C2N(C)N=CC2=CC=C1 OOEMPICOPPHXIM-UHFFFAOYSA-N 0.000 description 1
- WRLJGYOWTBEPJH-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(1-oxo-2,3-dihydroindene-4-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CC2=C1CCC2=O WRLJGYOWTBEPJH-UHFFFAOYSA-N 0.000 description 1
- LEOULSOFNJKRHT-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(1-propan-2-ylpyrazole-3-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound CC(C)N1C=CC(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=N1 LEOULSOFNJKRHT-UHFFFAOYSA-N 0.000 description 1
- PTULFHJQXGKICB-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(1-pyridin-2-ylcyclopropanecarbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1(C=2N=CC=CC=2)CC1 PTULFHJQXGKICB-UHFFFAOYSA-N 0.000 description 1
- AFCYFEXNMNOGQJ-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-methoxy-5-methylpyridine-3-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound COC1=NC=C(C)C=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 AFCYFEXNMNOGQJ-UHFFFAOYSA-N 0.000 description 1
- MWIGOQBAYJABQH-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-methoxyethyl)pyrazol-4-yl]phenyl]urea Chemical compound C1=NN(CCOC)C=C1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 MWIGOQBAYJABQH-UHFFFAOYSA-N 0.000 description 1
- XJRRMMXJELIBOH-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-methyl-1,3-benzoxazole-6-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=C2N=C(C)OC2=C1 XJRRMMXJELIBOH-UHFFFAOYSA-N 0.000 description 1
- ZGXMUKNPFFYUOF-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-methyl-2,3-dihydro-1-benzofuran-5-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=C(OC(C)C2)C2=C1 ZGXMUKNPFFYUOF-UHFFFAOYSA-N 0.000 description 1
- MTSBESQKNGJAEY-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-methyl-4,5,6,7-tetrahydroindazole-3-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=C2CCCCC2=NN1C MTSBESQKNGJAEY-UHFFFAOYSA-N 0.000 description 1
- JTZCJPJUGHAWGU-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-methylcyclopentene-1-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1CCC(C)=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 JTZCJPJUGHAWGU-UHFFFAOYSA-N 0.000 description 1
- LEDLTLWYGKPXJI-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-methylcyclopropanecarbonyl)piperidin-4-yl]phenyl]urea Chemical compound CC1CC1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 LEDLTLWYGKPXJI-UHFFFAOYSA-N 0.000 description 1
- NONIIYHIGYCLKA-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-methylindazole-4-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CC2=NN(C)C=C21 NONIIYHIGYCLKA-UHFFFAOYSA-N 0.000 description 1
- ZHZWEBOVDNPHJI-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-methylindazole-6-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC2=NN(C)C=C2C=C1 ZHZWEBOVDNPHJI-UHFFFAOYSA-N 0.000 description 1
- HIYMPISBICTBJG-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-methylpropanoyl)azetidin-3-yl]oxyphenyl]urea Chemical compound C1N(C(=O)C(C)C)CC1OC(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 HIYMPISBICTBJG-UHFFFAOYSA-N 0.000 description 1
- PFERSGSEHFXLQO-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-methylpropanoyl)azetidin-3-yl]phenyl]urea Chemical compound C1N(C(=O)C(C)C)CC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 PFERSGSEHFXLQO-UHFFFAOYSA-N 0.000 description 1
- WUQQYKMPUXFYOK-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-methylpropanoyl)piperidin-4-yl]oxyphenyl]urea Chemical compound C1CN(C(=O)C(C)C)CCC1OC(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 WUQQYKMPUXFYOK-UHFFFAOYSA-N 0.000 description 1
- PEMRXNWKHYUXJA-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl]urea Chemical compound C1CN(C(=O)C(C)C)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 PEMRXNWKHYUXJA-UHFFFAOYSA-N 0.000 description 1
- XRADIGFPECHUQR-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]phenyl]urea Chemical compound C1N(C(=O)C(C)C)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 XRADIGFPECHUQR-UHFFFAOYSA-N 0.000 description 1
- LHCUIOLMPLGJIK-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-methylpropyl)pyrazol-4-yl]phenyl]urea Chemical compound C1=NN(CC(C)C)C=C1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 LHCUIOLMPLGJIK-UHFFFAOYSA-N 0.000 description 1
- ULVDSUBKYCDXBC-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-morpholin-4-ylacetyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)CN1CCOCC1 ULVDSUBKYCDXBC-UHFFFAOYSA-N 0.000 description 1
- AOMMCPWGMAJUTP-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-morpholin-4-ylacetyl)pyrrolidin-3-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(C1)CCN1C(=O)CN1CCOCC1 AOMMCPWGMAJUTP-UHFFFAOYSA-N 0.000 description 1
- HWHRSRIEEIQGIF-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-phenylacetyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)CC1=CC=CC=C1 HWHRSRIEEIQGIF-UHFFFAOYSA-N 0.000 description 1
- KETXOWAAACNTFU-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-propan-2-yl-1,3-oxazole-4-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound O1C(C(C)C)=NC(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 KETXOWAAACNTFU-UHFFFAOYSA-N 0.000 description 1
- FRNOCQPUJBKKLL-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-propan-2-yloxyacetyl)azetidin-3-yl]oxyphenyl]urea Chemical compound C1N(C(=O)COC(C)C)CC1OC(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 FRNOCQPUJBKKLL-UHFFFAOYSA-N 0.000 description 1
- BKYAYIVHGPLCMY-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-propan-2-yloxyacetyl)azetidin-3-yl]phenyl]urea Chemical compound C1N(C(=O)COC(C)C)CC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 BKYAYIVHGPLCMY-UHFFFAOYSA-N 0.000 description 1
- ODHZYSYDDUEFOD-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-propan-2-yloxyacetyl)piperidin-4-yl]oxyphenyl]urea Chemical compound C1CN(C(=O)COC(C)C)CCC1OC(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 ODHZYSYDDUEFOD-UHFFFAOYSA-N 0.000 description 1
- HTDAXWPFHKCXJB-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(2-propan-2-yloxyacetyl)pyrrolidin-3-yl]phenyl]urea Chemical compound C1N(C(=O)COC(C)C)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 HTDAXWPFHKCXJB-UHFFFAOYSA-N 0.000 description 1
- TYOILJWCJPSHGJ-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]phenyl]urea Chemical compound C1CN(C(=O)CC(F)(F)F)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 TYOILJWCJPSHGJ-UHFFFAOYSA-N 0.000 description 1
- XGKQGVDQILFJQY-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(3-methoxythiophene-2-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CSC(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1OC XGKQGVDQILFJQY-UHFFFAOYSA-N 0.000 description 1
- CMZLSKKOPOJUPU-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(3-methylbut-2-enoyl)piperidin-4-yl]phenyl]urea Chemical compound C1CN(C(=O)C=C(C)C)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 CMZLSKKOPOJUPU-UHFFFAOYSA-N 0.000 description 1
- ISCUKDFXSYSVOT-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]phenyl]urea Chemical compound C1CN(C(=O)CCC(F)(F)F)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 ISCUKDFXSYSVOT-UHFFFAOYSA-N 0.000 description 1
- VPCGSQAHYCLLSJ-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(4,5,6,7-tetrahydro-1,3-benzothiazole-2-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1CCCC(S2)=C1N=C2C(=O)N(CC1)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 VPCGSQAHYCLLSJ-UHFFFAOYSA-N 0.000 description 1
- ZOFJQYCITUWOKW-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(4,5,6,7-tetrahydro-2,1-benzoxazole-3-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound O1N=C2CCCCC2=C1C(=O)N(CC1)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 ZOFJQYCITUWOKW-UHFFFAOYSA-N 0.000 description 1
- DQBQLUYMFSOPHX-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(4-methoxy-5-methylpyridine-2-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=C(C)C(OC)=CC(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=N1 DQBQLUYMFSOPHX-UHFFFAOYSA-N 0.000 description 1
- KBEBRNQFEWMRDD-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(4-methoxycyclohexanecarbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1CC(OC)CCC1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 KBEBRNQFEWMRDD-UHFFFAOYSA-N 0.000 description 1
- UUSPWBIZEXGHKD-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(4-methoxythiophene-2-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound COC1=CSC(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 UUSPWBIZEXGHKD-UHFFFAOYSA-N 0.000 description 1
- KQFFBDXYEWNEHG-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(4-methylfuro[3,2-b]pyrrole-5-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C(N1C)=CC2=C1C=CO2 KQFFBDXYEWNEHG-UHFFFAOYSA-N 0.000 description 1
- RITXUXUEQIITLD-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(4-propan-2-ylpyrimidine-5-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound CC(C)C1=NC=NC=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 RITXUXUEQIITLD-UHFFFAOYSA-N 0.000 description 1
- IBLDVGKOQGXISW-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(5,6,7,8-tetrahydroquinoline-3-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1CCCC2=CC(C(=O)N3CCC(CC3)C3=CC=C(C=C3)NC(NCC3=CC4=NC=CN4C=C3)=O)=CN=C21 IBLDVGKOQGXISW-UHFFFAOYSA-N 0.000 description 1
- TYLGMPAOXMMZCC-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(5-methyl-2-prop-2-enylpyrazole-3-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C=CCN1N=C(C)C=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 TYLGMPAOXMMZCC-UHFFFAOYSA-N 0.000 description 1
- DWOYSNCCKGVJFO-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(8-methylimidazo[1,2-a]pyridine-2-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CN2C=CC=C(C)C2=N1 DWOYSNCCKGVJFO-UHFFFAOYSA-N 0.000 description 1
- CJICPZFRBPVYKX-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(isoquinoline-4-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CC=C2C(C(=O)N3CCC(CC3)C3=CC=C(C=C3)NC(NCC3=CC4=NC=CN4C=C3)=O)=CN=CC2=C1 CJICPZFRBPVYKX-UHFFFAOYSA-N 0.000 description 1
- WMKOEIBJCMAIRW-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(isoquinoline-7-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN=CC2=CC(C(=O)N3CCC(CC3)C3=CC=C(C=C3)NC(NCC3=CC4=NC=CN4C=C3)=O)=CC=C21 WMKOEIBJCMAIRW-UHFFFAOYSA-N 0.000 description 1
- GLNWFQCYIPBLBP-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(isoquinoline-8-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=NC=C2C(C(=O)N3CCC(CC3)C3=CC=C(C=C3)NC(NCC3=CC4=NC=CN4C=C3)=O)=CC=CC2=C1 GLNWFQCYIPBLBP-UHFFFAOYSA-N 0.000 description 1
- GLKDXVNDBJLOAE-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(oxan-4-ylmethyl)pyrazol-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(=C1)C=NN1CC1CCOCC1 GLKDXVNDBJLOAE-UHFFFAOYSA-N 0.000 description 1
- JVZDJVIHTGQHMI-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(oxane-4-carbonyl)azetidin-3-yl]oxyphenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1OC(C1)CN1C(=O)C1CCOCC1 JVZDJVIHTGQHMI-UHFFFAOYSA-N 0.000 description 1
- BKBZJSLSUUMIPF-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(oxane-4-carbonyl)azetidin-3-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(C1)CN1C(=O)C1CCOCC1 BKBZJSLSUUMIPF-UHFFFAOYSA-N 0.000 description 1
- ZBHQSLLSLDYJMQ-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(oxane-4-carbonyl)piperidin-4-yl]oxyphenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1OC(CC1)CCN1C(=O)C1CCOCC1 ZBHQSLLSLDYJMQ-UHFFFAOYSA-N 0.000 description 1
- OXKFPYPTXDEWMD-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(oxane-4-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1CCOCC1 OXKFPYPTXDEWMD-UHFFFAOYSA-N 0.000 description 1
- GANVLOFTPNUBCS-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(oxane-4-carbonyl)pyrrolidin-3-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(C1)CCN1C(=O)C1CCOCC1 GANVLOFTPNUBCS-UHFFFAOYSA-N 0.000 description 1
- QUWRTSAWUMLEQC-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(oxolan-2-ylmethyl)pyrazol-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(=C1)C=NN1CC1CCCO1 QUWRTSAWUMLEQC-UHFFFAOYSA-N 0.000 description 1
- VCQSWBFGSLSHPV-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(oxolane-2-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1CCCO1 VCQSWBFGSLSHPV-UHFFFAOYSA-N 0.000 description 1
- JHKSHCVJLHIAEU-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(pyrazolo[1,5-a]pyridine-2-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=C2C=CC=CN2N=C1C(=O)N(CC1)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 JHKSHCVJLHIAEU-UHFFFAOYSA-N 0.000 description 1
- YIZGUPOMZUMWSV-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(quinoline-7-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CC=NC2=CC(C(=O)N3CCC(CC3)C3=CC=C(C=C3)NC(NCC3=CC4=NC=CN4C=C3)=O)=CC=C21 YIZGUPOMZUMWSV-UHFFFAOYSA-N 0.000 description 1
- SESHTECZTDYGCM-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(quinoxaline-2-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CC=CC2=NC(C(=O)N3CCC(CC3)C3=CC=C(C=C3)NC(NCC3=CC4=NC=CN4C=C3)=O)=CN=C21 SESHTECZTDYGCM-UHFFFAOYSA-N 0.000 description 1
- OPZFEKBICINAEG-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-(thieno[3,2-b]furan-5-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C(S1)=CC2=C1C=CO2 OPZFEKBICINAEG-UHFFFAOYSA-N 0.000 description 1
- ROQPKCSQRGMFIZ-HXUWFJFHSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(2r)-oxolane-2-carbonyl]azetidin-3-yl]oxyphenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1OC(C1)CN1C(=O)[C@H]1CCCO1 ROQPKCSQRGMFIZ-HXUWFJFHSA-N 0.000 description 1
- LUHYSENLDDVLJT-HXUWFJFHSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(2r)-oxolane-2-carbonyl]azetidin-3-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(C1)CN1C(=O)[C@H]1CCCO1 LUHYSENLDDVLJT-HXUWFJFHSA-N 0.000 description 1
- UKNSFBKVPAIRLB-JOCHJYFZSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(2r)-oxolane-2-carbonyl]piperidin-4-yl]oxyphenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1OC(CC1)CCN1C(=O)[C@H]1CCCO1 UKNSFBKVPAIRLB-JOCHJYFZSA-N 0.000 description 1
- VCQSWBFGSLSHPV-JOCHJYFZSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(2r)-oxolane-2-carbonyl]piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)[C@H]1CCCO1 VCQSWBFGSLSHPV-JOCHJYFZSA-N 0.000 description 1
- JPMPWSMGRMTHLW-VGAJERRHSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(2r)-oxolane-2-carbonyl]pyrrolidin-3-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(C1)CCN1C(=O)[C@H]1CCCO1 JPMPWSMGRMTHLW-VGAJERRHSA-N 0.000 description 1
- IKLDTRPOYTUFJG-INIZCTEOSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(2s)-2-methylbutanoyl]azetidin-3-yl]oxyphenyl]urea Chemical compound C1N(C(=O)[C@@H](C)CC)CC1OC(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 IKLDTRPOYTUFJG-INIZCTEOSA-N 0.000 description 1
- QWCAQZWKAOLLNM-INIZCTEOSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(2s)-2-methylbutanoyl]azetidin-3-yl]phenyl]urea Chemical compound C1N(C(=O)[C@@H](C)CC)CC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 QWCAQZWKAOLLNM-INIZCTEOSA-N 0.000 description 1
- ILEVARWXNAFAGZ-SFHVURJKSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(2s)-2-methylbutanoyl]piperidin-4-yl]oxyphenyl]urea Chemical compound C1CN(C(=O)[C@@H](C)CC)CCC1OC(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 ILEVARWXNAFAGZ-SFHVURJKSA-N 0.000 description 1
- OTSBXOZQBHYLBH-SFHVURJKSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(2s)-2-methylbutanoyl]piperidin-4-yl]phenyl]urea Chemical compound C1CN(C(=O)[C@@H](C)CC)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 OTSBXOZQBHYLBH-SFHVURJKSA-N 0.000 description 1
- SZYSIEYMGKENEE-DIMJTDRSSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(2s)-2-methylbutanoyl]pyrrolidin-3-yl]phenyl]urea Chemical compound C1N(C(=O)[C@@H](C)CC)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 SZYSIEYMGKENEE-DIMJTDRSSA-N 0.000 description 1
- ROQPKCSQRGMFIZ-FQEVSTJZSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(2s)-oxolane-2-carbonyl]azetidin-3-yl]oxyphenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1OC(C1)CN1C(=O)[C@@H]1CCCO1 ROQPKCSQRGMFIZ-FQEVSTJZSA-N 0.000 description 1
- LUHYSENLDDVLJT-FQEVSTJZSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(2s)-oxolane-2-carbonyl]azetidin-3-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(C1)CN1C(=O)[C@@H]1CCCO1 LUHYSENLDDVLJT-FQEVSTJZSA-N 0.000 description 1
- UKNSFBKVPAIRLB-QFIPXVFZSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(2s)-oxolane-2-carbonyl]piperidin-4-yl]oxyphenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1OC(CC1)CCN1C(=O)[C@@H]1CCCO1 UKNSFBKVPAIRLB-QFIPXVFZSA-N 0.000 description 1
- VCQSWBFGSLSHPV-QFIPXVFZSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(2s)-oxolane-2-carbonyl]piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)[C@@H]1CCCO1 VCQSWBFGSLSHPV-QFIPXVFZSA-N 0.000 description 1
- JPMPWSMGRMTHLW-QWAKEFERSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(2s)-oxolane-2-carbonyl]pyrrolidin-3-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(C1)CCN1C(=O)[C@@H]1CCCO1 JPMPWSMGRMTHLW-QWAKEFERSA-N 0.000 description 1
- AUUZMLPXFMUXDO-OAQYLSRUSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(3r)-oxolane-3-carbonyl]piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)[C@@H]1CCOC1 AUUZMLPXFMUXDO-OAQYLSRUSA-N 0.000 description 1
- AUUZMLPXFMUXDO-NRFANRHFSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(3s)-oxolane-3-carbonyl]piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)[C@H]1CCOC1 AUUZMLPXFMUXDO-NRFANRHFSA-N 0.000 description 1
- CNMMRTBTKRJNCM-ANYOKISRSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(3s)-oxolane-3-carbonyl]pyrrolidin-3-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(C1)CCN1C(=O)[C@H]1CCOC1 CNMMRTBTKRJNCM-ANYOKISRSA-N 0.000 description 1
- BXXGSXKLDLCZEW-JFQJCAQQSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(e)-2-methylbut-2-enoyl]piperidin-4-yl]phenyl]urea Chemical compound C1CN(C(=O)C(/C)=C/C)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 BXXGSXKLDLCZEW-JFQJCAQQSA-N 0.000 description 1
- RSEHWNRHASURSC-RMKNXTFCSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(e)-3-(2-methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl]phenyl]urea Chemical compound COC1=NC=CC=C1\C=C\C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 RSEHWNRHASURSC-RMKNXTFCSA-N 0.000 description 1
- YOYIHCCYELBKBC-CMDGGOBGSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[(e)-3-pyridin-2-ylprop-2-enoyl]piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)\C=C\C1=CC=CC=N1 YOYIHCCYELBKBC-CMDGGOBGSA-N 0.000 description 1
- MYQDJRHHXHRTSV-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[2-(1h-indol-3-yl)acetyl]piperidin-4-yl]phenyl]urea Chemical compound C1=CC=C2C(CC(=O)N3CCC(CC3)C3=CC=C(C=C3)NC(NCC3=CC4=NC=CN4C=C3)=O)=CNC2=C1 MYQDJRHHXHRTSV-UHFFFAOYSA-N 0.000 description 1
- ADXVDUDFZVXKDM-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[2-(2-methoxyphenyl)acetyl]piperidin-4-yl]phenyl]urea Chemical compound COC1=CC=CC=C1CC(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 ADXVDUDFZVXKDM-UHFFFAOYSA-N 0.000 description 1
- LNKNJFCIRUVUDH-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[2-(3-methoxyphenyl)acetyl]piperidin-4-yl]phenyl]urea Chemical compound COC1=CC=CC(CC(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 LNKNJFCIRUVUDH-UHFFFAOYSA-N 0.000 description 1
- WYHWUKRVUGNYGI-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[2-(oxan-4-yl)acetyl]azetidin-3-yl]oxyphenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1OC(C1)CN1C(=O)CC1CCOCC1 WYHWUKRVUGNYGI-UHFFFAOYSA-N 0.000 description 1
- FAMXVPOGENOFKR-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[2-(oxan-4-yl)acetyl]azetidin-3-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(C1)CN1C(=O)CC1CCOCC1 FAMXVPOGENOFKR-UHFFFAOYSA-N 0.000 description 1
- LAXRFCZMWSMEIQ-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[2-(oxan-4-yl)acetyl]piperidin-4-yl]oxyphenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1OC(CC1)CCN1C(=O)CC1CCOCC1 LAXRFCZMWSMEIQ-UHFFFAOYSA-N 0.000 description 1
- RLAWTTJYHMXULR-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[2-(oxan-4-yl)acetyl]piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)CC1CCOCC1 RLAWTTJYHMXULR-UHFFFAOYSA-N 0.000 description 1
- ZEGJKXWKSQYLBQ-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[2-(oxan-4-yl)acetyl]pyrrolidin-3-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(C1)CCN1C(=O)CC1CCOCC1 ZEGJKXWKSQYLBQ-UHFFFAOYSA-N 0.000 description 1
- UBFDVJRQCFKRHA-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[2-(oxolan-2-yl)acetyl]piperidin-4-yl]phenyl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)CC1CCCO1 UBFDVJRQCFKRHA-UHFFFAOYSA-N 0.000 description 1
- CGZJHGRWGZWKHO-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-[1-[2-(trifluoromethyl)furan-3-carbonyl]piperidin-4-yl]phenyl]urea Chemical compound O1C=CC(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1C(F)(F)F CGZJHGRWGZWKHO-UHFFFAOYSA-N 0.000 description 1
- HTSXKWGJNLIWRH-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[5-(piperidine-1-carbonyl)-1,3-thiazol-2-yl]urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(S1)=NC=C1C(=O)N1CCCCC1 HTSXKWGJNLIWRH-UHFFFAOYSA-N 0.000 description 1
- OXJYMSGTTUNHPP-UHFFFAOYSA-N 1-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-3-[4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl]urea Chemical compound C1CN(C(=O)C(C)C)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=C(Cl)N2C=C1 OXJYMSGTTUNHPP-UHFFFAOYSA-N 0.000 description 1
- OLLUCRMFTWELPT-UHFFFAOYSA-N 1-[2-fluoro-4-[1-(2-methylpropanoyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1N(C(=O)C(C)C)CCC(C=2C=C(F)C(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 OLLUCRMFTWELPT-UHFFFAOYSA-N 0.000 description 1
- WMEVWEKXBKCUBH-UHFFFAOYSA-N 1-[2-fluoro-4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CN(C(=O)C(C)C)CCC1C(C=C1F)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 WMEVWEKXBKCUBH-UHFFFAOYSA-N 0.000 description 1
- FUKHCKXYLDJOEW-UHFFFAOYSA-N 1-[2-fluoro-4-[1-(4-methylpentanoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CN(C(=O)CCC(C)C)CCC1C(C=C1F)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 FUKHCKXYLDJOEW-UHFFFAOYSA-N 0.000 description 1
- ADZKCPWARTZQCO-UHFFFAOYSA-N 1-[2-fluoro-4-[1-(oxane-4-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C=1C=C(NC(=O)NCC2=CC3=NC=CN3C=C2)C(F)=CC=1C(CC1)CCN1C(=O)C1CCOCC1 ADZKCPWARTZQCO-UHFFFAOYSA-N 0.000 description 1
- SCIYRQGRUIEIQD-UHFFFAOYSA-N 1-[2-fluoro-4-[1-(oxolane-2-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C=1C=C(NC(=O)NCC2=CC3=NC=CN3C=C2)C(F)=CC=1C(CC1)=CCN1C(=O)C1CCCO1 SCIYRQGRUIEIQD-UHFFFAOYSA-N 0.000 description 1
- CXOHDWOMPKLZHZ-UHFFFAOYSA-N 1-[2-fluoro-4-[1-(pyridine-2-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C=1C=C(NC(=O)NCC2=CC3=NC=CN3C=C2)C(F)=CC=1C(CC1)CCN1C(=O)C1=CC=CC=N1 CXOHDWOMPKLZHZ-UHFFFAOYSA-N 0.000 description 1
- BOUXTOUDVPQYRH-KRWDZBQOSA-N 1-[2-fluoro-4-[1-[(2s)-2-methylbutanoyl]piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CN(C(=O)[C@@H](C)CC)CCC1C(C=C1F)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 BOUXTOUDVPQYRH-KRWDZBQOSA-N 0.000 description 1
- VDJXXQQHQJCDQB-UHFFFAOYSA-N 1-[2-fluoro-4-[1-[2-(oxan-4-yl)acetyl]-3,6-dihydro-2h-pyridin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C=1C=C(NC(=O)NCC2=CC3=NC=CN3C=C2)C(F)=CC=1C(CC1)=CCN1C(=O)CC1CCOCC1 VDJXXQQHQJCDQB-UHFFFAOYSA-N 0.000 description 1
- YURYRHOCMIQNKJ-UHFFFAOYSA-N 1-[4-(1-acetylazetidin-3-yl)oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1N(C(=O)C)CC1OC(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 YURYRHOCMIQNKJ-UHFFFAOYSA-N 0.000 description 1
- FJIRRMXEJVFLAL-UHFFFAOYSA-N 1-[4-(1-acetylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1N(C(=O)C)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 FJIRRMXEJVFLAL-UHFFFAOYSA-N 0.000 description 1
- NXYWUXQKHSQVAX-UHFFFAOYSA-N 1-[4-(1-benzoyl-3,6-dihydro-2h-pyridin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C=1C=C(NC(=O)NCC2=CC3=NC=CN3C=C2)C(F)=CC=1C(CC1)=CCN1C(=O)C1=CC=CC=C1 NXYWUXQKHSQVAX-UHFFFAOYSA-N 0.000 description 1
- JPKLXCBIYUVNHR-UHFFFAOYSA-N 1-[4-(1-benzoylazetidin-3-yl)oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1OC(C1)CN1C(=O)C1=CC=CC=C1 JPKLXCBIYUVNHR-UHFFFAOYSA-N 0.000 description 1
- NZXATZDVHVRNAG-UHFFFAOYSA-N 1-[4-(1-benzoylazetidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(C1)CN1C(=O)C1=CC=CC=C1 NZXATZDVHVRNAG-UHFFFAOYSA-N 0.000 description 1
- KZSVWXYFSPRAMS-UHFFFAOYSA-N 1-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C=1C=C(NC(=O)NCC2=CC3=NC=CN3C=C2)C(F)=CC=1C(CC1)CCN1C(=O)C1=CC=CC=C1 KZSVWXYFSPRAMS-UHFFFAOYSA-N 0.000 description 1
- UQAWYYJJFMQQHT-UHFFFAOYSA-N 1-[4-(1-benzoylpiperidin-4-yl)butyl]-3-imidazo[1,2-a]pyridin-6-ylurea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NCCCCC(CC1)CCN1C(=O)C1=CC=CC=C1 UQAWYYJJFMQQHT-UHFFFAOYSA-N 0.000 description 1
- IODQZESAAVXLTK-UHFFFAOYSA-N 1-[4-(1-benzoylpiperidin-4-yl)butyl]-3-imidazo[1,2-a]pyridin-7-ylurea Chemical compound C1=CN2C=CN=C2C=C1NC(=O)NCCCCC(CC1)CCN1C(=O)C1=CC=CC=C1 IODQZESAAVXLTK-UHFFFAOYSA-N 0.000 description 1
- JZXVQYZLDBKNHI-UHFFFAOYSA-N 1-[4-(1-benzoylpiperidin-4-yl)oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1OC(CC1)CCN1C(=O)C1=CC=CC=C1 JZXVQYZLDBKNHI-UHFFFAOYSA-N 0.000 description 1
- GGMHQOXQGFXMND-UHFFFAOYSA-N 1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CC=C1 GGMHQOXQGFXMND-UHFFFAOYSA-N 0.000 description 1
- FILMRFRYTMMCRG-UHFFFAOYSA-N 1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-imidazo[1,2-a]pyridin-6-ylurea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CC=C1 FILMRFRYTMMCRG-UHFFFAOYSA-N 0.000 description 1
- QTHGVGUAPUYEJW-UHFFFAOYSA-N 1-[4-(1-benzoylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(C1)CCN1C(=O)C1=CC=CC=C1 QTHGVGUAPUYEJW-UHFFFAOYSA-N 0.000 description 1
- QZZUSIMRBQFBEF-UHFFFAOYSA-N 1-[4-(1-butanoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CN(C(=O)CCC)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 QZZUSIMRBQFBEF-UHFFFAOYSA-N 0.000 description 1
- MHXYCLKSZJWOMJ-OAQYLSRUSA-N 1-[4-[(3r)-1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC(F)=CC=C1C(=O)N1C[C@H](OC=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 MHXYCLKSZJWOMJ-OAQYLSRUSA-N 0.000 description 1
- IXIDDOMGULBCPP-OAQYLSRUSA-N 1-[4-[(3r)-1-(2-chlorobenzoyl)pyrrolidin-3-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound ClC1=CC=CC=C1C(=O)N1C[C@H](OC=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 IXIDDOMGULBCPP-OAQYLSRUSA-N 0.000 description 1
- UJYGAKCFKDHJCD-OAQYLSRUSA-N 1-[4-[(3r)-1-(2-cyclopropylacetyl)pyrrolidin-3-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C([C@H](C1)OC2=CC=C(C=C2)NC(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)CC1CC1 UJYGAKCFKDHJCD-OAQYLSRUSA-N 0.000 description 1
- NTMBNFUUWUPTCI-OAQYLSRUSA-N 1-[4-[(3r)-1-(2-fluorobenzoyl)pyrrolidin-3-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC=CC=C1C(=O)N1C[C@H](OC=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 NTMBNFUUWUPTCI-OAQYLSRUSA-N 0.000 description 1
- VZDPWAZBPNLIHL-LJQANCHMSA-N 1-[4-[(3r)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1N(C(=O)C(C)(O)C)CC[C@H]1OC(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 VZDPWAZBPNLIHL-LJQANCHMSA-N 0.000 description 1
- GGMHXCNWHPECFJ-HSZRJFAPSA-N 1-[4-[(3r)-1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC(F)=CC(C(=O)N2C[C@@H](CC2)OC=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 GGMHXCNWHPECFJ-HSZRJFAPSA-N 0.000 description 1
- JOOUMGXZGHFAHE-HSZRJFAPSA-N 1-[4-[(3r)-1-(3-fluorobenzoyl)pyrrolidin-3-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC=CC(C(=O)N2C[C@@H](CC2)OC=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 JOOUMGXZGHFAHE-HSZRJFAPSA-N 0.000 description 1
- CKFBFDMQPGKCKT-HSZRJFAPSA-N 1-[4-[(3r)-1-(4-chlorobenzoyl)pyrrolidin-3-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CC(Cl)=CC=C1C(=O)N1C[C@H](OC=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 CKFBFDMQPGKCKT-HSZRJFAPSA-N 0.000 description 1
- JQDDLTDKSADOJZ-HSZRJFAPSA-N 1-[4-[(3r)-1-(4-fluorobenzoyl)pyrrolidin-3-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@H](OC=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 JQDDLTDKSADOJZ-HSZRJFAPSA-N 0.000 description 1
- BWLLDQFCISFXTJ-HXUWFJFHSA-N 1-[4-[(3r)-1-(cyclopropanecarbonyl)pyrrolidin-3-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C([C@H](C1)OC2=CC=C(C=C2)NC(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)C1CC1 BWLLDQFCISFXTJ-HXUWFJFHSA-N 0.000 description 1
- VECUTRMHSGUUOC-HSZRJFAPSA-N 1-[4-[(3r)-1-benzoylpyrrolidin-3-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C([C@H](C1)OC2=CC=C(C=C2)NC(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)C1=CC=CC=C1 VECUTRMHSGUUOC-HSZRJFAPSA-N 0.000 description 1
- IGANXNXKTNKDPL-UHFFFAOYSA-N 1-[4-[1-(1,1-dioxothiane-4-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-3-imidazo[1,2-a]pyridin-6-ylurea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(CC1)=CCN1C(=O)C1CCS(=O)(=O)CC1 IGANXNXKTNKDPL-UHFFFAOYSA-N 0.000 description 1
- QIGPOTXYCZZJHN-UHFFFAOYSA-N 1-[4-[1-(1,1-dioxothiane-4-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1CCS(=O)(=O)CC1 QIGPOTXYCZZJHN-UHFFFAOYSA-N 0.000 description 1
- VNBVNLNSKOOQFO-UHFFFAOYSA-N 1-[4-[1-(1,2,3-benzothiadiazole-5-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=C2SN=NC2=CC(C(=O)N2CCC(CC2)C2=CC=C(C=C2)NC(NCC2=CC3=NC=CN3C=C2)=O)=C1 VNBVNLNSKOOQFO-UHFFFAOYSA-N 0.000 description 1
- JNIDPBDVPSGOKS-UHFFFAOYSA-N 1-[4-[1-(1,3-benzothiazole-2-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CC=C2SC(C(=O)N3CCC(CC3)C3=CC=C(C=C3)NC(NCC3=CC4=NC=CN4C=C3)=O)=NC2=C1 JNIDPBDVPSGOKS-UHFFFAOYSA-N 0.000 description 1
- YTPLAMUYKPLTMB-UHFFFAOYSA-N 1-[4-[1-(1,3-benzothiazole-5-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=C2SC=NC2=CC(C(=O)N2CCC(CC2)C2=CC=C(C=C2)NC(NCC2=CC3=NC=CN3C=C2)=O)=C1 YTPLAMUYKPLTMB-UHFFFAOYSA-N 0.000 description 1
- VMMDFTWBXZBSQS-UHFFFAOYSA-N 1-[4-[1-(1,3-benzothiazole-7-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CC2=C1SC=N2 VMMDFTWBXZBSQS-UHFFFAOYSA-N 0.000 description 1
- PYZIMWZHPYONBO-UHFFFAOYSA-N 1-[4-[1-(1,4-dioxane-2-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-3-imidazo[1,2-a]pyridin-6-ylurea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(CC1)=CCN1C(=O)C1COCCO1 PYZIMWZHPYONBO-UHFFFAOYSA-N 0.000 description 1
- JGEFYLTYVNLZQE-UHFFFAOYSA-N 1-[4-[1-(1,4-dioxane-2-carbonyl)azetidin-3-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1OC(C1)CN1C(=O)C1COCCO1 JGEFYLTYVNLZQE-UHFFFAOYSA-N 0.000 description 1
- BEOVFORLXHDZNK-UHFFFAOYSA-N 1-[4-[1-(1,4-dioxane-2-carbonyl)piperidin-4-yl]butyl]-3-imidazo[1,2-a]pyridin-6-ylurea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NCCCCC(CC1)CCN1C(=O)C1COCCO1 BEOVFORLXHDZNK-UHFFFAOYSA-N 0.000 description 1
- CNUOXNYWVBOYED-UHFFFAOYSA-N 1-[4-[1-(1,4-dioxane-2-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1COCCO1 CNUOXNYWVBOYED-UHFFFAOYSA-N 0.000 description 1
- QETZHOXCQDYBMT-UHFFFAOYSA-N 1-[4-[1-(1,4-dioxane-2-carbonyl)pyrrolidin-3-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(C1)CCN1C(=O)C1COCCO1 QETZHOXCQDYBMT-UHFFFAOYSA-N 0.000 description 1
- WKLVRHBNJSNLEE-UHFFFAOYSA-N 1-[4-[1-(1,5-diethyltriazole-4-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound N1=NN(CC)C(CC)=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 WKLVRHBNJSNLEE-UHFFFAOYSA-N 0.000 description 1
- DOLYHUQTHLZACK-UHFFFAOYSA-N 1-[4-[1-(1-benzofuran-3-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CC=C2C(C(=O)N3CCC(CC3)C3=CC=C(C=C3)NC(NCC3=CC4=NC=CN4C=C3)=O)=COC2=C1 DOLYHUQTHLZACK-UHFFFAOYSA-N 0.000 description 1
- QTKJNMCEQHLRBZ-UHFFFAOYSA-N 1-[4-[1-(1-benzofuran-5-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=C2OC=CC2=CC(C(=O)N2CCC(CC2)C2=CC=C(C=C2)NC(NCC2=CC3=NC=CN3C=C2)=O)=C1 QTKJNMCEQHLRBZ-UHFFFAOYSA-N 0.000 description 1
- SYTJIAJPIKLMPC-UHFFFAOYSA-N 1-[4-[1-(1-cyano-3-methylcyclobutanecarbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1C(C)CC1(C#N)C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 SYTJIAJPIKLMPC-UHFFFAOYSA-N 0.000 description 1
- IYXYVJCCOYMBAG-UHFFFAOYSA-N 1-[4-[1-(1-cyanocyclopentanecarbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1(C#N)CCCC1 IYXYVJCCOYMBAG-UHFFFAOYSA-N 0.000 description 1
- UEOOCFUQOURNSE-UHFFFAOYSA-N 1-[4-[1-(1-cyclopentylpyrazole-3-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C(=N1)C=CN1C1CCCC1 UEOOCFUQOURNSE-UHFFFAOYSA-N 0.000 description 1
- LZDDMRIUHCTDDS-UHFFFAOYSA-N 1-[4-[1-(1-ethyl-3-propan-2-ylpyrazole-4-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound CC(C)C1=NN(CC)C=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 LZDDMRIUHCTDDS-UHFFFAOYSA-N 0.000 description 1
- AJJODHKAETUYKE-UHFFFAOYSA-N 1-[4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CN(C(=O)C(C)(C)C)CCC1C(C=C1F)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 AJJODHKAETUYKE-UHFFFAOYSA-N 0.000 description 1
- YTIXOYQKEUYPRH-UHFFFAOYSA-N 1-[4-[1-(2,3-dihydro-1,4-benzodioxine-3-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 YTIXOYQKEUYPRH-UHFFFAOYSA-N 0.000 description 1
- PTOWJKCMQKGGET-UHFFFAOYSA-N 1-[4-[1-(2,3-dihydro-1,4-benzodioxine-5-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound O1CCOC2=C1C=CC=C2C(=O)N(CC1)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 PTOWJKCMQKGGET-UHFFFAOYSA-N 0.000 description 1
- LROVTUQDSNIDLQ-UHFFFAOYSA-N 1-[4-[1-(2,3-dihydro-1-benzofuran-2-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1C2=CC=CC=C2OC1C(=O)N(CC1)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 LROVTUQDSNIDLQ-UHFFFAOYSA-N 0.000 description 1
- ADPHUXSCQRQZEM-UHFFFAOYSA-N 1-[4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC(F)=CC=C1C(=O)N1CCC(OC=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 ADPHUXSCQRQZEM-UHFFFAOYSA-N 0.000 description 1
- UKLYDEAVVQMESB-UHFFFAOYSA-N 1-[4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC(F)=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 UKLYDEAVVQMESB-UHFFFAOYSA-N 0.000 description 1
- MZYHLWSNWIWCLP-UHFFFAOYSA-N 1-[4-[1-(2,4-dimethoxybenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound COC1=CC(OC)=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 MZYHLWSNWIWCLP-UHFFFAOYSA-N 0.000 description 1
- ZJQLHWAHIZQSFD-UHFFFAOYSA-N 1-[4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC=C(F)C(C(=O)N2CCC(CC2)OC=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 ZJQLHWAHIZQSFD-UHFFFAOYSA-N 0.000 description 1
- UCHZZMLZCSJQAJ-UHFFFAOYSA-N 1-[4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC=C(F)C(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 UCHZZMLZCSJQAJ-UHFFFAOYSA-N 0.000 description 1
- CKXABKPQWGPREN-UHFFFAOYSA-N 1-[4-[1-(2,5-dimethoxybenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound COC1=CC=C(OC)C(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 CKXABKPQWGPREN-UHFFFAOYSA-N 0.000 description 1
- GCXANRUIFJMSDV-UHFFFAOYSA-N 1-[4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound COC1=CC=CC(OC)=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 GCXANRUIFJMSDV-UHFFFAOYSA-N 0.000 description 1
- GMTHSARAOYQLSA-UHFFFAOYSA-N 1-[4-[1-(2-chloro-3-fluoropyridine-4-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=C(Cl)N=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 GMTHSARAOYQLSA-UHFFFAOYSA-N 0.000 description 1
- JIXPHKNRIWYZOP-UHFFFAOYSA-N 1-[4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound ClC1=CC(C#N)=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 JIXPHKNRIWYZOP-UHFFFAOYSA-N 0.000 description 1
- RHQXVUILOALKLS-UHFFFAOYSA-N 1-[4-[1-(2-chloro-5-fluoropyridine-4-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CN=C(Cl)C=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 RHQXVUILOALKLS-UHFFFAOYSA-N 0.000 description 1
- MBPBIQZBXIFPQQ-UHFFFAOYSA-N 1-[4-[1-(2-chloro-6-methylpyridine-4-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound ClC1=NC(C)=CC(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 MBPBIQZBXIFPQQ-UHFFFAOYSA-N 0.000 description 1
- VZLJOZFSYMREFB-UHFFFAOYSA-N 1-[4-[1-(2-chloropyridine-3-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound ClC1=NC=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 VZLJOZFSYMREFB-UHFFFAOYSA-N 0.000 description 1
- DGBAUFQFPXTZDV-UHFFFAOYSA-N 1-[4-[1-(2-cyanobenzoyl)piperidin-4-yl]-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C=1C=C(NC(=O)NCC2=CC3=NC=CN3C=C2)C(F)=CC=1C(CC1)CCN1C(=O)C1=CC=CC=C1C#N DGBAUFQFPXTZDV-UHFFFAOYSA-N 0.000 description 1
- PYZJPRWSUFNAAJ-UHFFFAOYSA-N 1-[4-[1-(2-cyclopentylpyrazole-3-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=NN1C1CCCC1 PYZJPRWSUFNAAJ-UHFFFAOYSA-N 0.000 description 1
- WBSKLLMNCAFARL-UHFFFAOYSA-N 1-[4-[1-(2-cyclopropyl-1,3-thiazole-5-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C(S1)=CN=C1C1CC1 WBSKLLMNCAFARL-UHFFFAOYSA-N 0.000 description 1
- BGMMYHRBPBZDGC-UHFFFAOYSA-N 1-[4-[1-(2-cyclopropylacetyl)azetidin-3-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1OC(C1)CN1C(=O)CC1CC1 BGMMYHRBPBZDGC-UHFFFAOYSA-N 0.000 description 1
- QDRZJKMHLSZIEC-UHFFFAOYSA-N 1-[4-[1-(2-cyclopropylacetyl)azetidin-3-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(C1)CN1C(=O)CC1CC1 QDRZJKMHLSZIEC-UHFFFAOYSA-N 0.000 description 1
- LTKDNLSEMXPNRL-UHFFFAOYSA-N 1-[4-[1-(2-cyclopropylacetyl)piperidin-4-yl]butyl]-3-imidazo[1,2-a]pyridin-6-ylurea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NCCCCC(CC1)CCN1C(=O)CC1CC1 LTKDNLSEMXPNRL-UHFFFAOYSA-N 0.000 description 1
- OYNVMUCCNUEROO-UHFFFAOYSA-N 1-[4-[1-(2-cyclopropylacetyl)piperidin-4-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1OC(CC1)CCN1C(=O)CC1CC1 OYNVMUCCNUEROO-UHFFFAOYSA-N 0.000 description 1
- HSJYQHSWTSZZCF-UHFFFAOYSA-N 1-[4-[1-(2-cyclopropylacetyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)CC1CC1 HSJYQHSWTSZZCF-UHFFFAOYSA-N 0.000 description 1
- ICESFQBKABAPPS-UHFFFAOYSA-N 1-[4-[1-(2-cyclopropylacetyl)pyrrolidin-3-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(C1)CCN1C(=O)CC1CC1 ICESFQBKABAPPS-UHFFFAOYSA-N 0.000 description 1
- FNBORWAHHDWJLI-UHFFFAOYSA-N 1-[4-[1-(2-ethoxyacetyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-3-imidazo[1,2-a]pyridin-6-ylurea Chemical compound C1N(C(=O)COCC)CCC(C=2C=CC(NC(=O)NC3=CN4C=CN=C4C=C3)=CC=2)=C1 FNBORWAHHDWJLI-UHFFFAOYSA-N 0.000 description 1
- XGWFVOORLUSPRY-UHFFFAOYSA-N 1-[4-[1-(2-ethoxypyridine-4-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=NC(OCC)=CC(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 XGWFVOORLUSPRY-UHFFFAOYSA-N 0.000 description 1
- VONPUSMSIGXBBR-UHFFFAOYSA-N 1-[4-[1-(2-ethyl-1,3-thiazole-4-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound S1C(CC)=NC(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 VONPUSMSIGXBBR-UHFFFAOYSA-N 0.000 description 1
- QFUMWXDRFWEKKJ-UHFFFAOYSA-N 1-[4-[1-(2-ethylbutanoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CN(C(=O)C(CC)CC)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 QFUMWXDRFWEKKJ-UHFFFAOYSA-N 0.000 description 1
- TWHXPSRYAFWVLQ-UHFFFAOYSA-N 1-[4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 TWHXPSRYAFWVLQ-UHFFFAOYSA-N 0.000 description 1
- HEZWRJDBPYQOMJ-UHFFFAOYSA-N 1-[4-[1-(2-hydroxy-2-methylpropanoyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-3-imidazo[1,2-a]pyridin-6-ylurea Chemical compound C1N(C(=O)C(C)(O)C)CCC(C=2C=CC(NC(=O)NC3=CN4C=CN=C4C=C3)=CC=2)=C1 HEZWRJDBPYQOMJ-UHFFFAOYSA-N 0.000 description 1
- AQGZTNDLMYAXSS-UHFFFAOYSA-N 1-[4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1N(C(=O)C(C)(O)C)CC1OC(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 AQGZTNDLMYAXSS-UHFFFAOYSA-N 0.000 description 1
- JFYDDJCRGIEWOB-UHFFFAOYSA-N 1-[4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1N(C(=O)C(C)(O)C)CC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 JFYDDJCRGIEWOB-UHFFFAOYSA-N 0.000 description 1
- LDHKUSSZEHFNNV-UHFFFAOYSA-N 1-[4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CN(C(=O)C(C)(O)C)CCC1OC(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 LDHKUSSZEHFNNV-UHFFFAOYSA-N 0.000 description 1
- FKBOXTAHXDANPT-UHFFFAOYSA-N 1-[4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CN(C(=O)C(C)(O)C)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 FKBOXTAHXDANPT-UHFFFAOYSA-N 0.000 description 1
- AFPQASMTFKSQNB-UHFFFAOYSA-N 1-[4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1N(C(=O)C(C)(O)C)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 AFPQASMTFKSQNB-UHFFFAOYSA-N 0.000 description 1
- NUJPATOUUMPOCL-UHFFFAOYSA-N 1-[4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound CC1=CC=CC(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1O NUJPATOUUMPOCL-UHFFFAOYSA-N 0.000 description 1
- UROYKDDYVAZGBM-UHFFFAOYSA-N 1-[4-[1-(2-tert-butyl-5-methylpyrazole-3-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound CC(C)(C)N1N=C(C)C=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 UROYKDDYVAZGBM-UHFFFAOYSA-N 0.000 description 1
- VIIITIGNHDGZBW-UHFFFAOYSA-N 1-[4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CN(C(=O)CC(C)(C)C)CCC1C(C=C1F)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 VIIITIGNHDGZBW-UHFFFAOYSA-N 0.000 description 1
- XBUOCFBSYMIXFU-UHFFFAOYSA-N 1-[4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CN(C(=O)CC(C)(C)C)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 XBUOCFBSYMIXFU-UHFFFAOYSA-N 0.000 description 1
- JWUQFOCQGHOLSA-UHFFFAOYSA-N 1-[4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=C(F)C(F)=CC=C1C(=O)N1CCC(OC=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 JWUQFOCQGHOLSA-UHFFFAOYSA-N 0.000 description 1
- MUYNLYKRWAJTRI-UHFFFAOYSA-N 1-[4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=C(F)C(F)=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 MUYNLYKRWAJTRI-UHFFFAOYSA-N 0.000 description 1
- OMNMNYFWQUWPRH-UHFFFAOYSA-N 1-[4-[1-(3,4-dihydro-2h-pyrano[2,3-b]pyridine-6-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound O1CCCC2=CC(C(=O)N3CCC(CC3)C3=CC=C(C=C3)NC(NCC3=CC4=NC=CN4C=C3)=O)=CN=C21 OMNMNYFWQUWPRH-UHFFFAOYSA-N 0.000 description 1
- VIEYXUJBPVVUDE-UHFFFAOYSA-N 1-[4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC(F)=CC(C(=O)N2CCC(CC2)OC=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 VIEYXUJBPVVUDE-UHFFFAOYSA-N 0.000 description 1
- NQKIUXYVFNTWFB-UHFFFAOYSA-N 1-[4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC(F)=CC(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 NQKIUXYVFNTWFB-UHFFFAOYSA-N 0.000 description 1
- GCKDKMNWXRXTJI-UHFFFAOYSA-N 1-[4-[1-(3,5-difluoropyridine-2-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC(F)=CN=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 GCKDKMNWXRXTJI-UHFFFAOYSA-N 0.000 description 1
- PCLGKIZTIMLDPX-UHFFFAOYSA-N 1-[4-[1-(3-chloro-5-cyanopyridine-2-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound ClC1=CC(C#N)=CN=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 PCLGKIZTIMLDPX-UHFFFAOYSA-N 0.000 description 1
- WZAAUAYZYGDBSS-UHFFFAOYSA-N 1-[4-[1-(3-chloropyridine-2-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound ClC1=CC=CN=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 WZAAUAYZYGDBSS-UHFFFAOYSA-N 0.000 description 1
- SFSIPOQFICWBAH-UHFFFAOYSA-N 1-[4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=C(C#N)C(F)=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 SFSIPOQFICWBAH-UHFFFAOYSA-N 0.000 description 1
- VJXNSBLOTAQJRH-UHFFFAOYSA-N 1-[4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC(C#N)=CC(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 VJXNSBLOTAQJRH-UHFFFAOYSA-N 0.000 description 1
- XEMFQHBMNSBLQB-UHFFFAOYSA-N 1-[4-[1-(3-cyanothiophene-2-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C=1SC=CC=1C#N XEMFQHBMNSBLQB-UHFFFAOYSA-N 0.000 description 1
- CSDWTFOQJHPYKY-UHFFFAOYSA-N 1-[4-[1-(3-cyclopropyl-1,2-oxazole-5-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C(ON=1)=CC=1C1CC1 CSDWTFOQJHPYKY-UHFFFAOYSA-N 0.000 description 1
- FYRWHCLZLYDDOI-UHFFFAOYSA-N 1-[4-[1-(3-ethyl-1,2-oxazole-5-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound O1N=C(CC)C=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 FYRWHCLZLYDDOI-UHFFFAOYSA-N 0.000 description 1
- ZHQKTHGRVDCNMF-UHFFFAOYSA-N 1-[4-[1-(3-fluoro-6-methylpyridine-2-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound CC1=CC=C(F)C(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=N1 ZHQKTHGRVDCNMF-UHFFFAOYSA-N 0.000 description 1
- NYRIVOJZTDGKPO-UHFFFAOYSA-N 1-[4-[1-(3-fluorobenzoyl)piperidin-4-yl]oxyphenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC=CC(C(=O)N2CCC(CC2)OC=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 NYRIVOJZTDGKPO-UHFFFAOYSA-N 0.000 description 1
- CZYSCOTUNSQKNW-UHFFFAOYSA-N 1-[4-[1-(3-fluorobenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC=CC(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 CZYSCOTUNSQKNW-UHFFFAOYSA-N 0.000 description 1
- DPXGDRBXPKCPOZ-UHFFFAOYSA-N 1-[4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CCN1C(=O)C(CO)C1=CC=CC=C1 DPXGDRBXPKCPOZ-UHFFFAOYSA-N 0.000 description 1
- WMEHBINAFHNPPF-UHFFFAOYSA-N 1-[4-[1-(3-hydroxy-3-methylbutanoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CN(C(=O)CC(C)(O)C)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 WMEHBINAFHNPPF-UHFFFAOYSA-N 0.000 description 1
- IQZLVNAPQKXUJJ-UHFFFAOYSA-N 1-[4-[1-(4,4-difluorocyclohexanecarbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CC(F)(F)CCC1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 IQZLVNAPQKXUJJ-UHFFFAOYSA-N 0.000 description 1
- AAAKHNVBEUJFMM-UHFFFAOYSA-N 1-[4-[1-(4-chloro-1,3-thiazole-5-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound N1=CSC(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1Cl AAAKHNVBEUJFMM-UHFFFAOYSA-N 0.000 description 1
- XLMIGNNWAHTFBC-UHFFFAOYSA-N 1-[4-[1-(4-chloro-2,5-dimethylpyrazole-3-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound CC1=NN(C)C(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1Cl XLMIGNNWAHTFBC-UHFFFAOYSA-N 0.000 description 1
- DCDDHTHAKLFADT-UHFFFAOYSA-N 1-[4-[1-(4-chloro-2,6-dimethylpyridine-3-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound CC1=NC(C)=CC(Cl)=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 DCDDHTHAKLFADT-UHFFFAOYSA-N 0.000 description 1
- XRWHOCJNMVKCHT-UHFFFAOYSA-N 1-[4-[1-(4-chloro-2-ethylpyrazole-3-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound CCN1N=CC(Cl)=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 XRWHOCJNMVKCHT-UHFFFAOYSA-N 0.000 description 1
- AUGZALLKLAYWSU-UHFFFAOYSA-N 1-[4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC(C#N)=CC(F)=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 AUGZALLKLAYWSU-UHFFFAOYSA-N 0.000 description 1
- DWCVIOGYPJMGTO-UHFFFAOYSA-N 1-[4-[1-(4-fluorobenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CC(F)=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 DWCVIOGYPJMGTO-UHFFFAOYSA-N 0.000 description 1
- NBFNGPHWGWNNNZ-UHFFFAOYSA-N 1-[4-[1-(5,6-dimethoxypyridine-2-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound N1=C(OC)C(OC)=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 NBFNGPHWGWNNNZ-UHFFFAOYSA-N 0.000 description 1
- ISVVGWSFPMZUFP-UHFFFAOYSA-N 1-[4-[1-(5,6-dimethylpyridine-3-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound N1=C(C)C(C)=CC(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 ISVVGWSFPMZUFP-UHFFFAOYSA-N 0.000 description 1
- VGQMRUXDFRTZMB-UHFFFAOYSA-N 1-[4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC1=CC=C(C#N)C=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 VGQMRUXDFRTZMB-UHFFFAOYSA-N 0.000 description 1
- XMZGBZKBKQHFGR-UHFFFAOYSA-N 1-[4-[1-(5-cyanothiophene-2-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=C(C#N)S1 XMZGBZKBKQHFGR-UHFFFAOYSA-N 0.000 description 1
- ZKTXNYGAZLLLQO-UHFFFAOYSA-N 1-[4-[1-(5-cyclopropyl-2-methylpyrazole-3-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=C(C(=O)N2CCC(CC2)C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)N(C)N=C1C1CC1 ZKTXNYGAZLLLQO-UHFFFAOYSA-N 0.000 description 1
- BOTGYNDHTZRQNU-UHFFFAOYSA-N 1-[4-[1-(5-cyclopropylpyridine-2-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C(N=C1)=CC=C1C1CC1 BOTGYNDHTZRQNU-UHFFFAOYSA-N 0.000 description 1
- ZKPGNTZKAVGPAT-UHFFFAOYSA-N 1-[4-[1-(5-ethylpyridine-2-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound N1=CC(CC)=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 ZKPGNTZKAVGPAT-UHFFFAOYSA-N 0.000 description 1
- APHMIOOOJIYBSK-UHFFFAOYSA-N 1-[4-[1-(cinnoline-4-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CC=C2C(C(=O)N3CCC(CC3)C3=CC=C(C=C3)NC(NCC3=CC4=NC=CN4C=C3)=O)=CN=NC2=C1 APHMIOOOJIYBSK-UHFFFAOYSA-N 0.000 description 1
- CLDYDTLUQCHFJQ-UHFFFAOYSA-N 1-[4-[1-(cyclohex-3-ene-1-carbonyl)piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1CCC=CC1 CLDYDTLUQCHFJQ-UHFFFAOYSA-N 0.000 description 1
- YQRDWNFLELOIBJ-UHFFFAOYSA-N 1-[4-[1-(cyclopentanecarbonyl)piperidin-4-yl]butyl]-3-imidazo[1,2-a]pyridin-6-ylurea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NCCCCC(CC1)CCN1C(=O)C1CCCC1 YQRDWNFLELOIBJ-UHFFFAOYSA-N 0.000 description 1
- YTIXOYQKEUYPRH-SANMLTNESA-N 1-[4-[1-[(3s)-2,3-dihydro-1,4-benzodioxine-3-carbonyl]piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1OC2=CC=CC=C2O[C@@H]1C(=O)N(CC1)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 YTIXOYQKEUYPRH-SANMLTNESA-N 0.000 description 1
- NXIBGTGWJWSMSQ-UHFFFAOYSA-N 1-[4-[1-[2-(2-ethylpiperidin-1-yl)-2-oxoacetyl]piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound CCC1CCCCN1C(=O)C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 NXIBGTGWJWSMSQ-UHFFFAOYSA-N 0.000 description 1
- NRMHMDJZTDOYJY-UHFFFAOYSA-N 1-[4-[1-[2-(3-cyclopropylpyrazol-1-yl)propanoyl]piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CCN1C(=O)C(C)N(N=1)C=CC=1C1CC1 NRMHMDJZTDOYJY-UHFFFAOYSA-N 0.000 description 1
- CKILORCPODFPNL-UHFFFAOYSA-N 1-[4-[1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CCN1C(=O)C(C)OC1=CC=CC(F)=C1 CKILORCPODFPNL-UHFFFAOYSA-N 0.000 description 1
- MFBOETROUFPTKM-UHFFFAOYSA-N 1-[4-[1-[2-(4-cyanophenyl)acetyl]piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)CC1=CC=C(C#N)C=C1 MFBOETROUFPTKM-UHFFFAOYSA-N 0.000 description 1
- OMRFYLFYMSIUOY-UHFFFAOYSA-N 1-[4-[1-[2-(4-fluorophenoxy)acetyl]piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1=CC(F)=CC=C1OCC(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 OMRFYLFYMSIUOY-UHFFFAOYSA-N 0.000 description 1
- ZXRMVUYVLUEIJC-UHFFFAOYSA-N 1-[4-[1-[2-(difluoromethyl)pyrazole-3-carbonyl]piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound FC(F)N1N=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)CC1 ZXRMVUYVLUEIJC-UHFFFAOYSA-N 0.000 description 1
- NAXGGFSKFLKXMW-UHFFFAOYSA-N 1-[4-[1-[3-(diethylamino)propanoyl]piperidin-4-yl]phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea Chemical compound C1CN(C(=O)CCN(CC)CC)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 NAXGGFSKFLKXMW-UHFFFAOYSA-N 0.000 description 1
- 125000006083 1-bromoethyl group Chemical group 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- LYXSNCJPWRMEEE-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-(1-methylpiperidine-4-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]urea Chemical compound C1CN(C)CCC1C(=O)N1CC=C(C=2C=CC(NC(=O)NC3=CN4C=CN=C4C=C3)=CC=2)CC1 LYXSNCJPWRMEEE-UHFFFAOYSA-N 0.000 description 1
- FLJLGIKMNVREIG-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-(2-methylpropanoyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]urea Chemical compound C1N(C(=O)C(C)C)CCC(C=2C=CC(NC(=O)NC3=CN4C=CN=C4C=C3)=CC=2)=C1 FLJLGIKMNVREIG-UHFFFAOYSA-N 0.000 description 1
- PMXUTGDGOPSICK-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl]urea Chemical compound C1CN(C(=O)C(C)C)CCC1C(C=C1)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 PMXUTGDGOPSICK-UHFFFAOYSA-N 0.000 description 1
- AUNHDDFBBABHTO-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-(2-methylpropyl)pyrazol-4-yl]phenyl]urea Chemical compound C1=NN(CC(C)C)C=C1C(C=C1)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 AUNHDDFBBABHTO-UHFFFAOYSA-N 0.000 description 1
- ZFAJKWNRCQKEIK-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-(2-morpholin-4-ylacetyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]urea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(CC1)=CCN1C(=O)CN1CCOCC1 ZFAJKWNRCQKEIK-UHFFFAOYSA-N 0.000 description 1
- CODICSQTDXCJIS-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-(2-morpholin-4-ylacetyl)piperidin-4-yl]butyl]urea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NCCCCC(CC1)CCN1C(=O)CN1CCOCC1 CODICSQTDXCJIS-UHFFFAOYSA-N 0.000 description 1
- PHJJXWBJKONMHX-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-(2-propan-2-yloxyacetyl)piperidin-4-yl]butyl]urea Chemical compound C1CN(C(=O)COC(C)C)CCC1CCCCNC(=O)NC1=CN2C=CN=C2C=C1 PHJJXWBJKONMHX-UHFFFAOYSA-N 0.000 description 1
- PDLYEBWVRGQIPL-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]butyl]urea Chemical compound C1CN(C(=O)CCC(F)(F)F)CCC1CCCCNC(=O)NC1=CN2C=CN=C2C=C1 PDLYEBWVRGQIPL-UHFFFAOYSA-N 0.000 description 1
- VYJKSXWVFFVBEM-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-(oxane-4-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]urea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(CC1)=CCN1C(=O)C1CCOCC1 VYJKSXWVFFVBEM-UHFFFAOYSA-N 0.000 description 1
- YPPZNNQEJHSYPG-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-(oxane-4-carbonyl)piperidin-4-yl]butyl]urea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NCCCCC(CC1)CCN1C(=O)C1CCOCC1 YPPZNNQEJHSYPG-UHFFFAOYSA-N 0.000 description 1
- VLZDQHARMCLKOQ-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-(oxane-4-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1CCOCC1 VLZDQHARMCLKOQ-UHFFFAOYSA-N 0.000 description 1
- OLFKZBJHACUOHQ-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-(oxolane-2-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]urea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(CC1)=CCN1C(=O)C1CCCO1 OLFKZBJHACUOHQ-UHFFFAOYSA-N 0.000 description 1
- MGSWPIGTOFPWFW-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-(oxolane-2-carbonyl)piperidin-4-yl]butyl]urea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NCCCCC(CC1)CCN1C(=O)C1CCCO1 MGSWPIGTOFPWFW-UHFFFAOYSA-N 0.000 description 1
- FWPCMCDWDUNUQF-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-(oxolane-2-carbonyl)piperidin-4-yl]phenyl]urea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1CCCO1 FWPCMCDWDUNUQF-UHFFFAOYSA-N 0.000 description 1
- DPODCOJTNMICNY-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-(oxolane-3-carbonyl)piperidin-4-yl]butyl]urea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NCCCCC(CC1)CCN1C(=O)C1CCOC1 DPODCOJTNMICNY-UHFFFAOYSA-N 0.000 description 1
- QDMICLCELCOPQR-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-[2-(2-methoxyethoxy)acetyl]-3,6-dihydro-2h-pyridin-4-yl]phenyl]urea Chemical compound C1N(C(=O)COCCOC)CCC(C=2C=CC(NC(=O)NC3=CN4C=CN=C4C=C3)=CC=2)=C1 QDMICLCELCOPQR-UHFFFAOYSA-N 0.000 description 1
- BQISOSLZUYOLSZ-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-[2-(2-methoxyethoxy)acetyl]piperidin-4-yl]butyl]urea Chemical compound C1CN(C(=O)COCCOC)CCC1CCCCNC(=O)NC1=CN2C=CN=C2C=C1 BQISOSLZUYOLSZ-UHFFFAOYSA-N 0.000 description 1
- LHRBQOYVOBSEMD-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-[2-(oxan-4-yl)acetyl]piperidin-4-yl]butyl]urea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NCCCCC(CC1)CCN1C(=O)CC1CCOCC1 LHRBQOYVOBSEMD-UHFFFAOYSA-N 0.000 description 1
- UWBOQLLEUMSPDW-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-[2-(oxolan-2-yl)acetyl]piperidin-4-yl]butyl]urea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NCCCCC(CC1)CCN1C(=O)CC1CCCO1 UWBOQLLEUMSPDW-UHFFFAOYSA-N 0.000 description 1
- VEDIFZULZMRYCS-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-[2-(oxolan-2-yl)acetyl]piperidin-4-yl]phenyl]urea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)CC1CCCO1 VEDIFZULZMRYCS-UHFFFAOYSA-N 0.000 description 1
- MZWQZHKRLDDTHH-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-[2-(oxolan-3-yl)acetyl]-3,6-dihydro-2h-pyridin-4-yl]phenyl]urea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(CC1)=CCN1C(=O)CC1CCOC1 MZWQZHKRLDDTHH-UHFFFAOYSA-N 0.000 description 1
- QMRHLASYIAVOOZ-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-[2-(oxolan-3-yl)acetyl]piperidin-4-yl]butyl]urea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NCCCCC(CC1)CCN1C(=O)CC1CCOC1 QMRHLASYIAVOOZ-UHFFFAOYSA-N 0.000 description 1
- SOSVGWJUMZOMBZ-UHFFFAOYSA-N 1-imidazo[1,2-a]pyridin-6-yl-3-[4-[1-[2-(oxolan-3-yl)acetyl]piperidin-4-yl]phenyl]urea Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)CC1CCOC1 SOSVGWJUMZOMBZ-UHFFFAOYSA-N 0.000 description 1
- JMWPSCUIQIMVQH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-pyrrolo[3,4-c]pyridine Chemical group C1NCCC2CNCC21 JMWPSCUIQIMVQH-UHFFFAOYSA-N 0.000 description 1
- QFKVQNJEBLYEAH-UHFFFAOYSA-N 2,3,3a,4,6,6a-hexahydro-1h-furo[3,4-b]pyrrole Chemical group C1OCC2NCCC21 QFKVQNJEBLYEAH-UHFFFAOYSA-N 0.000 description 1
- KSCPLKVBWDOSAI-UHFFFAOYSA-N 2,3,4,4a,5,6,7,7a-octahydro-1h-pyrrolo[3,4-b]pyridine Chemical group N1CCCC2CNCC21 KSCPLKVBWDOSAI-UHFFFAOYSA-N 0.000 description 1
- LSESNOMCHBUBEH-UHFFFAOYSA-N 2,4-difluoro-n-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenyl]benzamide Chemical compound FC1=CC(F)=CC=C1C(=O)NC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 LSESNOMCHBUBEH-UHFFFAOYSA-N 0.000 description 1
- YLPKUCGIBRNKFU-UHFFFAOYSA-N 2,5-difluoro-n-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenyl]benzamide Chemical compound FC1=CC=C(F)C(C(=O)NC=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 YLPKUCGIBRNKFU-UHFFFAOYSA-N 0.000 description 1
- NNLXRZSGSPUDCK-UHFFFAOYSA-N 2-(1,3-dihydroisoindol-2-yl)-n-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(S1)=NC=C1C(=O)NCC1=CN2C=CN=C2C=C1 NNLXRZSGSPUDCK-UHFFFAOYSA-N 0.000 description 1
- HRIDHVUJOAMALY-UHFFFAOYSA-N 2-(1-benzoyl-3,6-dihydro-2h-pyridin-4-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CN=C1C(CC1)=CCN1C(=O)C1=CC=CC=C1 HRIDHVUJOAMALY-UHFFFAOYSA-N 0.000 description 1
- IASJKAUZJLSALN-UHFFFAOYSA-N 2-(1-benzoylpiperidin-4-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CN=C1C(CC1)CCN1C(=O)C1=CC=CC=C1 IASJKAUZJLSALN-UHFFFAOYSA-N 0.000 description 1
- YXIKMXLAUBMWQX-UHFFFAOYSA-N 2-(1-benzoylpyrrolidin-3-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CN=C1C(C1)CCN1C(=O)C1=CC=CC=C1 YXIKMXLAUBMWQX-UHFFFAOYSA-N 0.000 description 1
- PNYRYIZLQXUUCL-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinolin-2-yl)-n-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C1CC2=CC=CC=C2CN1C(S1)=NC=C1C(=O)NCC1=CN2C=CN=C2C=C1 PNYRYIZLQXUUCL-UHFFFAOYSA-N 0.000 description 1
- JTBNDXKFFJZFET-UHFFFAOYSA-N 2-(4-benzoylpiperazin-1-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CN=C1N(CC1)CCN1C(=O)C1=CC=CC=C1 JTBNDXKFFJZFET-UHFFFAOYSA-N 0.000 description 1
- LYCRBARUCPYJOV-UHFFFAOYSA-N 2-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoylamino)-n-(3-methylbutyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NCCC(C)C)=CN=C1NC(=O)NCC1=CC2=NC=CN2C=C1 LYCRBARUCPYJOV-UHFFFAOYSA-N 0.000 description 1
- FKPQOSDTFKSPIE-LBPRGKRZSA-N 2-[(2s)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound OC[C@@H]1CCC(=O)N1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 FKPQOSDTFKSPIE-LBPRGKRZSA-N 0.000 description 1
- XWFDVGSEQLJVFZ-UHFFFAOYSA-N 2-[(4-cyanophenyl)methyl-(3-methoxypropanoyl)amino]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)SC=1N(C(=O)CCOC)CC1=CC=C(C#N)C=C1 XWFDVGSEQLJVFZ-UHFFFAOYSA-N 0.000 description 1
- AVSLJMATKXMBJS-UHFFFAOYSA-N 2-[(4-cyanophenyl)methyl-(3-methoxypropanoyl)amino]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)SC=1N(C(=O)CCOC)CC1=CC=C(C#N)C=C1 AVSLJMATKXMBJS-UHFFFAOYSA-N 0.000 description 1
- WCESURPIEMHPGL-UHFFFAOYSA-N 2-[(4-cyanophenyl)methyl-(3-methoxypropanoyl)amino]-n-imidazo[1,2-a]pyridin-6-yl-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NC2=CN3C=CN=C3C=C2)SC=1N(C(=O)CCOC)CC1=CC=C(C#N)C=C1 WCESURPIEMHPGL-UHFFFAOYSA-N 0.000 description 1
- FBAYTAZZNQNGMM-UHFFFAOYSA-N 2-[(4-cyanophenyl)methyl-(3-methylbutanoyl)amino]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)SC=1N(C(=O)CC(C)C)CC1=CC=C(C#N)C=C1 FBAYTAZZNQNGMM-UHFFFAOYSA-N 0.000 description 1
- GYZNIHIZBGBWCU-UHFFFAOYSA-N 2-[(4-cyanophenyl)methyl-(3-methylbutanoyl)amino]-n-imidazo[1,2-a]pyridin-6-yl-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NC2=CN3C=CN=C3C=C2)SC=1N(C(=O)CC(C)C)CC1=CC=C(C#N)C=C1 GYZNIHIZBGBWCU-UHFFFAOYSA-N 0.000 description 1
- FRBBNANAQWQASP-UHFFFAOYSA-N 2-[1-(2-fluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound FC1=CC=CC=C1C(=O)N1CCC(C=2SC(=CN=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 FRBBNANAQWQASP-UHFFFAOYSA-N 0.000 description 1
- LKXQMHPBMOCMLB-UHFFFAOYSA-N 2-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound FC1=CC=CC=C1C(=O)N1CC(C=2SC(=CN=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 LKXQMHPBMOCMLB-UHFFFAOYSA-N 0.000 description 1
- QHMWIDJFFAKWII-UHFFFAOYSA-N 2-[1-(2-hydroxy-2-methylpropyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C1=NN(CC(C)(O)C)C=C1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 QHMWIDJFFAKWII-UHFFFAOYSA-N 0.000 description 1
- IHFYCZDWHJDLEK-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CN=C1C(C1)CCN1S(=O)(=O)C1=CC=CC=C1 IHFYCZDWHJDLEK-UHFFFAOYSA-N 0.000 description 1
- XMTYRDUCNLZDSL-UHFFFAOYSA-N 2-[3-(3,5-dimethyl-1,2-oxazol-4-yl)propanoyl-(oxolan-2-ylmethyl)amino]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC1=NOC(C)=C1CCC(=O)N(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)CC1OCCC1 XMTYRDUCNLZDSL-UHFFFAOYSA-N 0.000 description 1
- LNRVZASCOYFVMJ-UHFFFAOYSA-N 2-[3-(3-chloro-1,2-oxazol-5-yl)propanoyl-(oxolan-2-ylmethyl)amino]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound O1N=C(Cl)C=C1CCC(=O)N(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)CC1OCCC1 LNRVZASCOYFVMJ-UHFFFAOYSA-N 0.000 description 1
- CTHZTZMLXHLEJZ-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-2-oxo-1,3-oxazolidin-3-yl]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1OC(=O)N(C=2SC(=CN=2)C(=O)NCC2=CN3C=CN=C3C=C2)C1 CTHZTZMLXHLEJZ-UHFFFAOYSA-N 0.000 description 1
- AMWOVVAFFWEWFJ-UHFFFAOYSA-N 2-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound O=C1OC(CO)CN1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 AMWOVVAFFWEWFJ-UHFFFAOYSA-N 0.000 description 1
- WCEYUAWYIJAAST-UHFFFAOYSA-N 2-[[2-(1,3-dimethylpyrazol-4-yl)acetyl]-(oxolan-2-ylmethyl)amino]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC1=NN(C)C=C1CC(=O)N(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)CC1OCCC1 WCEYUAWYIJAAST-UHFFFAOYSA-N 0.000 description 1
- RPKMGPQUHDJTKB-UHFFFAOYSA-N 2-[[2-(1,5-dimethylpyrazol-3-yl)acetyl]-(oxolan-2-ylmethyl)amino]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CN1C(C)=CC(CC(=O)N(CC2OCCC2)C=2SC(=CN=2)C(=O)NCC2=CN3C=CN=C3C=C2)=N1 RPKMGPQUHDJTKB-UHFFFAOYSA-N 0.000 description 1
- VBGWUDCAESRNKE-LJQANCHMSA-N 2-[[2-(1,5-dimethylpyrazol-3-yl)acetyl]-[[(2r)-oxolan-2-yl]methyl]amino]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CN1C(C)=CC(CC(=O)N(C[C@@H]2OCCC2)C=2SC(=CN=2)C(=O)NCC2=CC3=NC=CN3C=C2)=N1 VBGWUDCAESRNKE-LJQANCHMSA-N 0.000 description 1
- QGOQBJJRESOVEF-UHFFFAOYSA-N 2-[[2-(3,5-dimethyl-1,2-oxazol-4-yl)acetyl]-(oxolan-2-ylmethyl)amino]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC1=NOC(C)=C1CC(=O)N(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)CC1OCCC1 QGOQBJJRESOVEF-UHFFFAOYSA-N 0.000 description 1
- RIOZRKBKHAWVOJ-GOSISDBHSA-N 2-[[2-(3,5-dimethyl-1,2-oxazol-4-yl)acetyl]-[[(2r)-oxolan-2-yl]methyl]amino]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC1=NOC(C)=C1CC(=O)N(C=1SC(=CN=1)C(=O)NCC1=CC2=NC=CN2C=C1)C[C@@H]1OCCC1 RIOZRKBKHAWVOJ-GOSISDBHSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- LPFNDZVYZORLJT-UHFFFAOYSA-N 2-cyclopentyl-n-[4-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethylcarbamoylamino)phenyl]acetamide Chemical compound C=1C=C(NC(=O)NCC2=CC3=NC=NN3C=C2)C=CC=1NC(=O)CC1CCCC1 LPFNDZVYZORLJT-UHFFFAOYSA-N 0.000 description 1
- BGIMTEMTZICJCB-UHFFFAOYSA-N 2-cyclopentyl-n-[4-(imidazo[1,2-a]pyrazin-6-ylmethylcarbamoylamino)phenyl]acetamide Chemical compound C=1C=C(NC(=O)NCC=2N=CC3=NC=CN3C=2)C=CC=1NC(=O)CC1CCCC1 BGIMTEMTZICJCB-UHFFFAOYSA-N 0.000 description 1
- JMKHETSLDSFYER-UHFFFAOYSA-N 2-cyclopentyl-n-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]acetamide Chemical compound C=1C=C(NC(=O)NC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CC1CCCC1 JMKHETSLDSFYER-UHFFFAOYSA-N 0.000 description 1
- HMIJFUZAAIQDIG-UHFFFAOYSA-N 2-cyclopentyl-n-[4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoylamino)phenyl]acetamide Chemical compound C=1C=C(NC(=O)NCC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CC1CCCC1 HMIJFUZAAIQDIG-UHFFFAOYSA-N 0.000 description 1
- OXYOSMRXLKRBCU-UHFFFAOYSA-N 2-cyclopentyl-n-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoylamino)phenyl]acetamide Chemical compound C=1C=C(NC(=O)NCC2=CC3=NC=CN3C=C2)C=CC=1NC(=O)CC1CCCC1 OXYOSMRXLKRBCU-UHFFFAOYSA-N 0.000 description 1
- DXTPDWKXMVVISK-UHFFFAOYSA-N 2-cyclopentyl-n-[4-[(2-imidazo[1,2-a]pyridin-6-ylacetyl)amino]phenyl]acetamide Chemical compound C=1C=C(NC(=O)CC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CC1CCCC1 DXTPDWKXMVVISK-UHFFFAOYSA-N 0.000 description 1
- FXXYSENNCNWSSQ-UHFFFAOYSA-N 2-cyclopentyl-n-[4-[(2-imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl]acetamide Chemical compound C=1C=C(NC(=O)CC2=CC3=NC=CN3C=C2)C=CC=1NC(=O)CC1CCCC1 FXXYSENNCNWSSQ-UHFFFAOYSA-N 0.000 description 1
- ASMLGXREXHIQOP-UHFFFAOYSA-N 2-cyclopentyl-n-[4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl]acetamide Chemical compound C=1C=C(CC(=O)NC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CC1CCCC1 ASMLGXREXHIQOP-UHFFFAOYSA-N 0.000 description 1
- XYFGSNANSPESNX-UHFFFAOYSA-N 2-ethoxy-n-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]acetamide Chemical compound C1=CC(NC(=O)COCC)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 XYFGSNANSPESNX-UHFFFAOYSA-N 0.000 description 1
- VPRXUTPZVOIHFE-UHFFFAOYSA-N 2-fluoro-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]benzamide Chemical compound C1CC(C=2C=C(F)C(C(=O)NCC=3N=CC4=NC=CN4C=3)=CC=2)CCN1C(=O)C1(C)CC1 VPRXUTPZVOIHFE-UHFFFAOYSA-N 0.000 description 1
- VUVWVRQFHFBGHM-UHFFFAOYSA-N 2-fluoro-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide Chemical compound C1CN(C(=O)C(C)C)CCC1C(C=C1F)=CC=C1C(=O)NCC(N=C1)=CN2C1=NC=C2 VUVWVRQFHFBGHM-UHFFFAOYSA-N 0.000 description 1
- LUEQNPUQEDQMLV-UHFFFAOYSA-N 2-fluoro-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide Chemical compound C=1C=C(C(=O)NCC=2N=CC3=NC=CN3C=2)C(F)=CC=1C1CCN(C(=O)CC(F)(F)F)CC1 LUEQNPUQEDQMLV-UHFFFAOYSA-N 0.000 description 1
- PNBPUQITHPXDTF-UHFFFAOYSA-N 2-fluoro-n-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenyl]benzamide Chemical compound FC1=CC=CC=C1C(=O)NC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 PNBPUQITHPXDTF-UHFFFAOYSA-N 0.000 description 1
- OVLZDXMKLVUEPZ-UHFFFAOYSA-N 2-imidazo[1,2-a]pyridin-6-yl-n-[4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl]acetamide Chemical compound C1CN(C(=O)C(C)C)CCC1C(C=C1)=CC=C1NC(=O)CC1=CN2C=CN=C2C=C1 OVLZDXMKLVUEPZ-UHFFFAOYSA-N 0.000 description 1
- JRWZEKZNLMQYFT-UHFFFAOYSA-N 2-imidazo[1,2-a]pyridin-7-yl-n-[4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl]acetamide Chemical compound C1CN(C(=O)C(C)C)CCC1C(C=C1)=CC=C1NC(=O)CC1=CC2=NC=CN2C=C1 JRWZEKZNLMQYFT-UHFFFAOYSA-N 0.000 description 1
- BCPWYBRKWGULFF-UHFFFAOYSA-N 2-methylpropyl 4-[5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 BCPWYBRKWGULFF-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- HQQVXVKQOPZRBJ-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydro-1h-furo[3,4-c]pyrrole Chemical group C1OCC2CNCC21 HQQVXVKQOPZRBJ-UHFFFAOYSA-N 0.000 description 1
- UKCOMTPMRDBKFQ-UHFFFAOYSA-N 3,4-difluoro-n-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenyl]benzamide Chemical compound C1=C(F)C(F)=CC=C1C(=O)NC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 UKCOMTPMRDBKFQ-UHFFFAOYSA-N 0.000 description 1
- YCSWSSAZELCOSE-UHFFFAOYSA-N 3,5-difluoro-n-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenyl]benzamide Chemical compound FC1=CC(F)=CC(C(=O)NC=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 YCSWSSAZELCOSE-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- VUPDVQSFLREURD-UHFFFAOYSA-N 3-cyclopentyl-n-[4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoylamino)phenyl]propanamide Chemical compound C=1C=C(NC(=O)NCC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CCC1CCCC1 VUPDVQSFLREURD-UHFFFAOYSA-N 0.000 description 1
- BELKZHQWRHTNQG-UHFFFAOYSA-N 3-cyclopentyl-n-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoylamino)phenyl]propanamide Chemical compound C=1C=C(NC(=O)NCC2=CC3=NC=CN3C=C2)C=CC=1NC(=O)CCC1CCCC1 BELKZHQWRHTNQG-UHFFFAOYSA-N 0.000 description 1
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical group C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 description 1
- DKDRPSJRQYSVNN-UHFFFAOYSA-N 4,4,4-trifluoro-n-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]butanamide Chemical compound C1=CC(NC(=O)CCC(F)(F)F)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 DKDRPSJRQYSVNN-UHFFFAOYSA-N 0.000 description 1
- BOQXJWOXRFRNFG-UHFFFAOYSA-N 4-(1-acetylpiperidin-4-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CN(C(=O)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 BOQXJWOXRFRNFG-UHFFFAOYSA-N 0.000 description 1
- KSISNXIGEHIQJC-UHFFFAOYSA-N 4-(1-acetylpiperidin-4-yl)oxy-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C1CN(C(=O)C)CCC1OC1=CC=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=C1 KSISNXIGEHIQJC-UHFFFAOYSA-N 0.000 description 1
- ZJLVXRJMVJSSED-UHFFFAOYSA-N 4-(1-acetylpiperidin-4-yl)oxy-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CN(C(=O)C)CCC1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 ZJLVXRJMVJSSED-UHFFFAOYSA-N 0.000 description 1
- DHIYOLAXQYKISN-UHFFFAOYSA-N 4-(1-benzoyl-3,6-dihydro-2h-pyridin-4-yl)-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)=CCN1C(=O)C1=CC=CC=C1 DHIYOLAXQYKISN-UHFFFAOYSA-N 0.000 description 1
- LSMQCBMYBZFRGN-UHFFFAOYSA-N 4-(1-benzoylazetidin-3-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C1=CC=CC=C1 LSMQCBMYBZFRGN-UHFFFAOYSA-N 0.000 description 1
- NTNXLOIUBALPIJ-UHFFFAOYSA-N 4-(1-benzoylazetidin-3-yl)oxy-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1OC(C1)CN1C(=O)C1=CC=CC=C1 NTNXLOIUBALPIJ-UHFFFAOYSA-N 0.000 description 1
- HCTXFVRBBYWZAI-UHFFFAOYSA-N 4-(1-benzoylpiperidin-4-yl)-2-fluoro-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC=2N=CC3=NC=CN3C=2)C(F)=CC=1C(CC1)CCN1C(=O)C1=CC=CC=C1 HCTXFVRBBYWZAI-UHFFFAOYSA-N 0.000 description 1
- MSNNPPSCGUYICH-UHFFFAOYSA-N 4-(1-benzoylpiperidin-4-yl)oxy-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1OC(CC1)CCN1C(=O)C1=CC=CC=C1 MSNNPPSCGUYICH-UHFFFAOYSA-N 0.000 description 1
- MMCLVZMWLIKPKE-UHFFFAOYSA-N 4-(1-benzoylpyrrolidin-3-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C1=CC=CC=C1 MMCLVZMWLIKPKE-UHFFFAOYSA-N 0.000 description 1
- RLGYYYOQHXWAGO-UHFFFAOYSA-N 4-(1-butanoylpiperidin-4-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CN(C(=O)CCC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 RLGYYYOQHXWAGO-UHFFFAOYSA-N 0.000 description 1
- YDGVMRBNLQKZFQ-UHFFFAOYSA-N 4-(1-butanoylpiperidin-4-yl)oxy-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C1CN(C(=O)CCC)CCC1OC1=CC=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=C1 YDGVMRBNLQKZFQ-UHFFFAOYSA-N 0.000 description 1
- AQNSYBVJFZCFSL-UHFFFAOYSA-N 4-(1-cyclopropylsulfonylazetidin-3-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1S(=O)(=O)C1CC1 AQNSYBVJFZCFSL-UHFFFAOYSA-N 0.000 description 1
- IMGNLMVXPGCFAX-UHFFFAOYSA-N 4-(1-cyclopropylsulfonylpiperidin-4-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1S(=O)(=O)C1CC1 IMGNLMVXPGCFAX-UHFFFAOYSA-N 0.000 description 1
- XXIPAUWKKAECKM-UHFFFAOYSA-N 4-(1-cyclopropylsulfonylpyrrolidin-3-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1S(=O)(=O)C1CC1 XXIPAUWKKAECKM-UHFFFAOYSA-N 0.000 description 1
- BAVXAPRYCNUEQN-UHFFFAOYSA-N 4-(1-ethylsulfonylazetidin-3-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1N(S(=O)(=O)CC)CC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 BAVXAPRYCNUEQN-UHFFFAOYSA-N 0.000 description 1
- FPUUHAYKQYLUBM-UHFFFAOYSA-N 4-(1-ethylsulfonylpyrrolidin-3-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1N(S(=O)(=O)CC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 FPUUHAYKQYLUBM-UHFFFAOYSA-N 0.000 description 1
- MEKXABCGDCQJIT-UHFFFAOYSA-N 4-(3-cyclopentylpropanoylamino)-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CCC1CCCC1 MEKXABCGDCQJIT-UHFFFAOYSA-N 0.000 description 1
- VAFUYGVSTBIBKV-UHFFFAOYSA-N 4-(3-cyclopentylpropanoylamino)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=CC=1NC(=O)CCC1CCCC1 VAFUYGVSTBIBKV-UHFFFAOYSA-N 0.000 description 1
- LVWNWYLDDYUNFJ-UHFFFAOYSA-N 4-(benzenesulfonyl)-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)benzamide Chemical compound C1=CC2=NC=NN2C=C1CNC(=O)C(C=C1)=CC=C1S(=O)(=O)C1=CC=CC=C1 LVWNWYLDDYUNFJ-UHFFFAOYSA-N 0.000 description 1
- PRVCHOMCHFIKDN-UHFFFAOYSA-N 4-(benzenesulfonyl)-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide Chemical compound C=1N2C=CN=C2C=NC=1CNC(=O)C(C=C1)=CC=C1S(=O)(=O)C1=CC=CC=C1 PRVCHOMCHFIKDN-UHFFFAOYSA-N 0.000 description 1
- WZSQGPCDLYBLMU-UHFFFAOYSA-N 4-(benzenesulfonyl)-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(C=C1)=CC=C1S(=O)(=O)C1=CC=CC=C1 WZSQGPCDLYBLMU-UHFFFAOYSA-N 0.000 description 1
- RMTRJFBSYIGOOU-UHFFFAOYSA-N 4-(benzenesulfonyl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1S(=O)(=O)C1=CC=CC=C1 RMTRJFBSYIGOOU-UHFFFAOYSA-N 0.000 description 1
- RBCJEZMRHOUAFB-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-(2-methylbutyl)benzamide Chemical compound C1=CC(C(=O)NCC(C)CC)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 RBCJEZMRHOUAFB-UHFFFAOYSA-N 0.000 description 1
- RXENSJZZUABQCT-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(=O)NCCN1CCOCC1 RXENSJZZUABQCT-UHFFFAOYSA-N 0.000 description 1
- VTPWPHABZBWZDC-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-(2-phenoxyethyl)benzamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(=O)NCCOC1=CC=CC=C1 VTPWPHABZBWZDC-UHFFFAOYSA-N 0.000 description 1
- XBQZBRPRURCZBP-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-(2-phenylethyl)benzamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(=O)NCCC1=CC=CC=C1 XBQZBRPRURCZBP-UHFFFAOYSA-N 0.000 description 1
- UEAHQNGZTINFIR-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-(2-propan-2-yloxyethyl)benzamide Chemical compound C1=CC(C(=O)NCCOC(C)C)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 UEAHQNGZTINFIR-UHFFFAOYSA-N 0.000 description 1
- YYEBMYYAQPDNRE-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(=O)NCCN1CCCC1 YYEBMYYAQPDNRE-UHFFFAOYSA-N 0.000 description 1
- FTKHUKACWXMXCW-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-(3-methylbutyl)benzamide Chemical compound C1=CC(C(=O)NCCC(C)C)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 FTKHUKACWXMXCW-UHFFFAOYSA-N 0.000 description 1
- WKNYTEHYZCGTES-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-(3-morpholin-4-ylpropyl)benzamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(=O)NCCCN1CCOCC1 WKNYTEHYZCGTES-UHFFFAOYSA-N 0.000 description 1
- RKFUFDSNXGZQDF-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-(3-piperidin-1-ylpropyl)benzamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(=O)NCCCN1CCCCC1 RKFUFDSNXGZQDF-UHFFFAOYSA-N 0.000 description 1
- MLNSFKZDQJQYRN-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-(oxan-2-ylmethyl)benzamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(=O)NCC1CCCCO1 MLNSFKZDQJQYRN-UHFFFAOYSA-N 0.000 description 1
- ZHFFDTQBHOIIRD-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-(oxan-4-ylmethyl)benzamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(=O)NCC1CCOCC1 ZHFFDTQBHOIIRD-UHFFFAOYSA-N 0.000 description 1
- XSPGRWCOCSBJCB-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-(oxolan-2-ylmethyl)benzamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(=O)NCC1CCCO1 XSPGRWCOCSBJCB-UHFFFAOYSA-N 0.000 description 1
- MKEKGIMWHSENLU-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-[2-(2-oxopyrrolidin-1-yl)ethyl]benzamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(=O)NCCN1CCCC1=O MKEKGIMWHSENLU-UHFFFAOYSA-N 0.000 description 1
- IGOLXGYRMPACSM-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-[3-(2-oxopyrrolidin-1-yl)propyl]benzamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(=O)NCCCN1CCCC1=O IGOLXGYRMPACSM-UHFFFAOYSA-N 0.000 description 1
- FAZLDRQWWMKFHJ-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-phenylbenzamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1 FAZLDRQWWMKFHJ-UHFFFAOYSA-N 0.000 description 1
- NOIHWZFFJPQQRR-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)-n-propylbenzamide Chemical compound C1=CC(C(=O)NCCC)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 NOIHWZFFJPQQRR-UHFFFAOYSA-N 0.000 description 1
- GFVOTMLPQIMNRM-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoylamino)-n-(3-methylbutyl)benzamide Chemical compound C1=CC(C(=O)NCCC(C)C)=CC=C1NC(=O)NCC1=CN2C=CN=C2C=C1 GFVOTMLPQIMNRM-UHFFFAOYSA-N 0.000 description 1
- NPESGWAZJKTHJG-UHFFFAOYSA-N 4-(imidazo[1,2-a]pyridin-7-ylcarbamoylamino)-n-(3-methylbutyl)benzamide Chemical compound C1=CC(C(=O)NCCC(C)C)=CC=C1NC(=O)NC1=CC2=NC=CN2C=C1 NPESGWAZJKTHJG-UHFFFAOYSA-N 0.000 description 1
- IVWKKZZHMMFUMA-UHFFFAOYSA-N 4-[(2,2-difluoro-2-phenylacetyl)amino]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=CC=1NC(=O)C(F)(F)C1=CC=CC=C1 IVWKKZZHMMFUMA-UHFFFAOYSA-N 0.000 description 1
- DANCDYDCHCLBGO-UHFFFAOYSA-N 4-[(2-cyclopentylacetyl)amino]-2-fluoro-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC=2N=CC3=NC=CN3C=2)C(F)=CC=1NC(=O)CC1CCCC1 DANCDYDCHCLBGO-UHFFFAOYSA-N 0.000 description 1
- WYVYWBDBWDVVCS-UHFFFAOYSA-N 4-[(2-cyclopentylacetyl)amino]-2-fluoro-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)C(F)=CC=1NC(=O)CC1CCCC1 WYVYWBDBWDVVCS-UHFFFAOYSA-N 0.000 description 1
- IEKXDUNPDWYRLI-UHFFFAOYSA-N 4-[(2-cyclopentylacetyl)amino]-2-fluoro-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)C(F)=CC=1NC(=O)CC1CCCC1 IEKXDUNPDWYRLI-UHFFFAOYSA-N 0.000 description 1
- SWPKJIBFHWWKKS-UHFFFAOYSA-N 4-[(2-cyclopentylacetyl)amino]-3-fluoro-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC(C(=O)NCC2=CC3=NC=CN3C=C2)=CC=C1NC(=O)CC1CCCC1 SWPKJIBFHWWKKS-UHFFFAOYSA-N 0.000 description 1
- KYKIMGONIDWJSN-UHFFFAOYSA-N 4-[(2-cyclopentylacetyl)amino]-n-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=NN3C=C2)C=CC=1NC(=O)CC1CCCC1 KYKIMGONIDWJSN-UHFFFAOYSA-N 0.000 description 1
- FCUSBSCRONIGTQ-UHFFFAOYSA-N 4-[(2-cyclopentylacetyl)amino]-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC=2N=CC3=NC=CN3C=2)C=CC=1NC(=O)CC1CCCC1 FCUSBSCRONIGTQ-UHFFFAOYSA-N 0.000 description 1
- LXRXLWIIICNXLP-UHFFFAOYSA-N 4-[(2-cyclopentylacetyl)amino]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CC1CCCC1 LXRXLWIIICNXLP-UHFFFAOYSA-N 0.000 description 1
- QTSOYQNLOYMWSR-UHFFFAOYSA-N 4-[(2-cyclopentylacetyl)amino]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=CC=1NC(=O)CC1CCCC1 QTSOYQNLOYMWSR-UHFFFAOYSA-N 0.000 description 1
- YNWBUBVEBQFRRT-UHFFFAOYSA-N 4-[(2-cyclopentylacetyl)amino]-n-(imidazo[1,2-b]pyridazin-6-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC2=NN3C=CN=C3C=C2)C=CC=1NC(=O)CC1CCCC1 YNWBUBVEBQFRRT-UHFFFAOYSA-N 0.000 description 1
- SNWNIGDVJWBBKQ-UHFFFAOYSA-N 4-[(2-cyclopentylacetyl)amino]-n-[(7-fluoroimidazo[1,2-a]pyridin-6-yl)methyl]benzamide Chemical compound FC1=CC2=NC=CN2C=C1CNC(=O)C(C=C1)=CC=C1NC(=O)CC1CCCC1 SNWNIGDVJWBBKQ-UHFFFAOYSA-N 0.000 description 1
- LVGFFXJBMGHQJG-UHFFFAOYSA-N 4-[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoylamino]-n-(oxan-2-ylmethyl)benzamide Chemical compound C=1N2C(Cl)=CN=C2C=CC=1NC(=O)NC(C=C1)=CC=C1C(=O)NCC1CCCCO1 LVGFFXJBMGHQJG-UHFFFAOYSA-N 0.000 description 1
- ZGJVVUJYEHYSJA-HSZRJFAPSA-N 4-[(3r)-1-benzoylpyrrolidin-3-yl]oxy-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C([C@H](C1)OC2=CC=C(C=C2)C(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)C1=CC=CC=C1 ZGJVVUJYEHYSJA-HSZRJFAPSA-N 0.000 description 1
- QYGCOGOOMKMQFB-NRFANRHFSA-N 4-[(3s)-1-(2-cyclopropylacetyl)pyrrolidin-3-yl]oxy-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C([C@H](CC1)OC=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)N1C(=O)CC1CC1 QYGCOGOOMKMQFB-NRFANRHFSA-N 0.000 description 1
- JYDISGHFLYMCDE-IBGZPJMESA-N 4-[(3s)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1N(C(=O)C(C)(O)C)CC[C@@H]1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 JYDISGHFLYMCDE-IBGZPJMESA-N 0.000 description 1
- ZIXYDAWCUFFATP-FQEVSTJZSA-N 4-[(3s)-1-(3-hydroxy-3-methylbutanoyl)pyrrolidin-3-yl]oxy-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1N(C(=O)CC(C)(O)C)CC[C@@H]1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 ZIXYDAWCUFFATP-FQEVSTJZSA-N 0.000 description 1
- FNQUXXCUIFHNHH-FQEVSTJZSA-N 4-[(3s)-1-(cyclopropanecarbonyl)pyrrolidin-3-yl]oxy-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C([C@@H](C1)OC2=CC=C(C=C2)C(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)C1CC1 FNQUXXCUIFHNHH-FQEVSTJZSA-N 0.000 description 1
- ZGJVVUJYEHYSJA-QHCPKHFHSA-N 4-[(3s)-1-benzoylpyrrolidin-3-yl]oxy-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C([C@@H](C1)OC2=CC=C(C=C2)C(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)C1=CC=CC=C1 ZGJVVUJYEHYSJA-QHCPKHFHSA-N 0.000 description 1
- CNSCKCLCVZMFTG-FQEVSTJZSA-N 4-[(3s)-1-butanoylpyrrolidin-3-yl]oxy-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1N(C(=O)CCC)CC[C@@H]1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 CNSCKCLCVZMFTG-FQEVSTJZSA-N 0.000 description 1
- OKTJOVQWRUUONF-UHFFFAOYSA-N 4-[(4-cyanophenyl)methyl-(2-cyclopentylacetyl)amino]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C=1C=C(C#N)C=CC=1CN(C=1C=CC(=CC=1)C(=O)NCC1=CN2C=CN=C2C=C1)C(=O)CC1CCCC1 OKTJOVQWRUUONF-UHFFFAOYSA-N 0.000 description 1
- KYPKHVSQHIURJY-UHFFFAOYSA-N 4-[(4-cyanophenyl)methyl-(3-methoxypropanoyl)amino]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=CC=1N(C(=O)CCOC)CC1=CC=C(C#N)C=C1 KYPKHVSQHIURJY-UHFFFAOYSA-N 0.000 description 1
- HUTWSPREADASQL-UHFFFAOYSA-N 4-[1-(1,1-dioxothiane-4-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1CCS(=O)(=O)CC1 HUTWSPREADASQL-UHFFFAOYSA-N 0.000 description 1
- XSNMPHBUPXDAKI-UHFFFAOYSA-N 4-[1-(1,2,3-benzothiadiazole-5-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=C2SN=NC2=CC(C(=O)N2CCC(CC2)C2=CC=C(C=C2)C(NCC2=CC3=NC=CN3C=C2)=O)=C1 XSNMPHBUPXDAKI-UHFFFAOYSA-N 0.000 description 1
- NGAGOEYUTVKMMI-UHFFFAOYSA-N 4-[1-(1,3-benzothiazole-2-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CC=C2SC(C(=O)N3CCC(CC3)C3=CC=C(C=C3)C(NCC3=CC4=NC=CN4C=C3)=O)=NC2=C1 NGAGOEYUTVKMMI-UHFFFAOYSA-N 0.000 description 1
- IIGWJYBHJLMRKK-UHFFFAOYSA-N 4-[1-(1,3-benzothiazole-5-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=C2SC=NC2=CC(C(=O)N2CCC(CC2)C2=CC=C(C=C2)C(NCC2=CC3=NC=CN3C=C2)=O)=C1 IIGWJYBHJLMRKK-UHFFFAOYSA-N 0.000 description 1
- YEJTYQRHHYMMEU-UHFFFAOYSA-N 4-[1-(1,3-benzothiazole-7-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CC2=C1SC=N2 YEJTYQRHHYMMEU-UHFFFAOYSA-N 0.000 description 1
- MNRVYBKHSNUULS-UHFFFAOYSA-N 4-[1-(1,4-dioxane-2-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)=CCN1C(=O)C1COCCO1 MNRVYBKHSNUULS-UHFFFAOYSA-N 0.000 description 1
- TWNOYMNEBBEDET-UHFFFAOYSA-N 4-[1-(1,4-dioxane-2-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1COCCO1 TWNOYMNEBBEDET-UHFFFAOYSA-N 0.000 description 1
- JHIWRDOOOQLYET-UHFFFAOYSA-N 4-[1-(1,4-dioxane-2-carbonyl)piperidin-4-yl]oxy-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(C=C1)=CC=C1OC(CC1)CCN1C(=O)C1COCCO1 JHIWRDOOOQLYET-UHFFFAOYSA-N 0.000 description 1
- GTNAHPZCDKVWBI-UHFFFAOYSA-N 4-[1-(1,4-dioxane-2-carbonyl)piperidin-4-yl]oxy-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1OC(CC1)CCN1C(=O)C1COCCO1 GTNAHPZCDKVWBI-UHFFFAOYSA-N 0.000 description 1
- QXHHIBJTIWRHMZ-UHFFFAOYSA-N 4-[1-(1,4-dioxane-2-carbonyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C1COCCO1 QXHHIBJTIWRHMZ-UHFFFAOYSA-N 0.000 description 1
- LDALNQFXBBHGOW-UHFFFAOYSA-N 4-[1-(1,5-diethyltriazole-4-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound N1=NN(CC)C(CC)=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 LDALNQFXBBHGOW-UHFFFAOYSA-N 0.000 description 1
- JBNVOZFGKPEUGT-UHFFFAOYSA-N 4-[1-(1-benzofuran-3-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CC=C2C(C(=O)N3CCC(CC3)C3=CC=C(C=C3)C(NCC3=CC4=NC=CN4C=C3)=O)=COC2=C1 JBNVOZFGKPEUGT-UHFFFAOYSA-N 0.000 description 1
- WIZKDGVHDXNEAS-UHFFFAOYSA-N 4-[1-(1-benzofuran-5-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=C2OC=CC2=CC(C(=O)N2CCC(CC2)C2=CC=C(C=C2)C(NCC2=CC3=NC=CN3C=C2)=O)=C1 WIZKDGVHDXNEAS-UHFFFAOYSA-N 0.000 description 1
- ZYVZBAMBXJPLEI-UHFFFAOYSA-N 4-[1-(1-cyano-3-methylcyclobutanecarbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1C(C)CC1(C#N)C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 ZYVZBAMBXJPLEI-UHFFFAOYSA-N 0.000 description 1
- PWPYTJAFUMCFPI-UHFFFAOYSA-N 4-[1-(1-cyanocyclopentanecarbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1(C#N)CCCC1 PWPYTJAFUMCFPI-UHFFFAOYSA-N 0.000 description 1
- DLINJZYRTNZCGS-UHFFFAOYSA-N 4-[1-(1-cyanocyclopropanecarbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1(C#N)CC1 DLINJZYRTNZCGS-UHFFFAOYSA-N 0.000 description 1
- VILFOXJOZATSAV-UHFFFAOYSA-N 4-[1-(1-cyclopentylpyrazole-3-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C(=N1)C=CN1C1CCCC1 VILFOXJOZATSAV-UHFFFAOYSA-N 0.000 description 1
- VKICPWCMLLWAGV-UHFFFAOYSA-N 4-[1-(1-ethyl-3-propan-2-ylpyrazole-4-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound CC(C)C1=NN(CC)C=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 VKICPWCMLLWAGV-UHFFFAOYSA-N 0.000 description 1
- OWPPRWRPRDNKMU-UHFFFAOYSA-N 4-[1-(2,2-difluoro-2-phenylacetyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)C(F)(F)C1=CC=CC=C1 OWPPRWRPRDNKMU-UHFFFAOYSA-N 0.000 description 1
- LENMKOBIKRJBBE-UHFFFAOYSA-N 4-[1-(2,2-dimethylbutanoyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1N(C(=O)C(C)(C)CC)CC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 LENMKOBIKRJBBE-UHFFFAOYSA-N 0.000 description 1
- OWWNSLYAEBWUPE-UHFFFAOYSA-N 4-[1-(2,2-dimethylbutanoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CN(C(=O)C(C)(C)CC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 OWWNSLYAEBWUPE-UHFFFAOYSA-N 0.000 description 1
- VXBISLBRCOEAAL-UHFFFAOYSA-N 4-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1N(C(=O)C(C)(C)CC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 VXBISLBRCOEAAL-UHFFFAOYSA-N 0.000 description 1
- XHAWJJMRONGIMM-UHFFFAOYSA-N 4-[1-(2,2-dimethylpropanoyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1N(C(=O)C(C)(C)C)CC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 XHAWJJMRONGIMM-UHFFFAOYSA-N 0.000 description 1
- SZWWUJSRIJGVDA-UHFFFAOYSA-N 4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CN(C(=O)C(C)(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 SZWWUJSRIJGVDA-UHFFFAOYSA-N 0.000 description 1
- WIQSQRQHCPAWBF-UHFFFAOYSA-N 4-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1N(C(=O)C(C)(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 WIQSQRQHCPAWBF-UHFFFAOYSA-N 0.000 description 1
- NKQVABQIHPWVRT-UHFFFAOYSA-N 4-[1-(2,3-dihydro-1,4-benzodioxine-3-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCC1C(C=C1)=CC=C1C(=O)NCC1=CC2=NC=CN2C=C1 NKQVABQIHPWVRT-UHFFFAOYSA-N 0.000 description 1
- PLDOPMYJYVEQPX-UHFFFAOYSA-N 4-[1-(2,3-dihydro-1,4-benzodioxine-5-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound O1CCOC2=C1C=CC=C2C(=O)N(CC1)CCC1C(C=C1)=CC=C1C(=O)NCC1=CC2=NC=CN2C=C1 PLDOPMYJYVEQPX-UHFFFAOYSA-N 0.000 description 1
- QUPLPVQZQBAPLP-UHFFFAOYSA-N 4-[1-(2,3-dimethylbutanoyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1N(C(=O)C(C)C(C)C)CC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 QUPLPVQZQBAPLP-UHFFFAOYSA-N 0.000 description 1
- JHERBNVEGUAQLW-UHFFFAOYSA-N 4-[1-(2,3-dimethylbutanoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CN(C(=O)C(C)C(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 JHERBNVEGUAQLW-UHFFFAOYSA-N 0.000 description 1
- AUKRGBBGUNMZMU-UHFFFAOYSA-N 4-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1N(C(=O)C(C)C(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 AUKRGBBGUNMZMU-UHFFFAOYSA-N 0.000 description 1
- HSQJTGGESYUFFU-UHFFFAOYSA-N 4-[1-(2,4-difluorobenzoyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC(F)=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C1 HSQJTGGESYUFFU-UHFFFAOYSA-N 0.000 description 1
- WYKIFYNQDZOSJT-UHFFFAOYSA-N 4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC(F)=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 WYKIFYNQDZOSJT-UHFFFAOYSA-N 0.000 description 1
- HYVADCHRZCDSJO-UHFFFAOYSA-N 4-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC(F)=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 HYVADCHRZCDSJO-UHFFFAOYSA-N 0.000 description 1
- UYLAOPQKYWOAED-UHFFFAOYSA-N 4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide Chemical compound FC1=CC=C(F)C(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC=2N=CC3=NC=CN3C=2)=C1 UYLAOPQKYWOAED-UHFFFAOYSA-N 0.000 description 1
- SLOARJNQWWMXDH-UHFFFAOYSA-N 4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC=C(F)C(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 SLOARJNQWWMXDH-UHFFFAOYSA-N 0.000 description 1
- BVHZAIUAHHSFCO-UHFFFAOYSA-N 4-[1-(2,5-dimethylfuran-3-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound O1C(C)=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1C BVHZAIUAHHSFCO-UHFFFAOYSA-N 0.000 description 1
- SNEKAQSEXBMVLY-UHFFFAOYSA-N 4-[1-(2,6-difluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 SNEKAQSEXBMVLY-UHFFFAOYSA-N 0.000 description 1
- KDTGXICPZKDKDK-UHFFFAOYSA-N 4-[1-(2-chloro-3-fluoropyridine-4-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=C(Cl)N=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 KDTGXICPZKDKDK-UHFFFAOYSA-N 0.000 description 1
- QUHDITJYPTXLNF-UHFFFAOYSA-N 4-[1-(2-chloro-5-fluoropyridine-4-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CN=C(Cl)C=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 QUHDITJYPTXLNF-UHFFFAOYSA-N 0.000 description 1
- UIMMRXFISPFMGW-UHFFFAOYSA-N 4-[1-(2-chloro-6-methylpyridine-4-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound ClC1=NC(C)=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 UIMMRXFISPFMGW-UHFFFAOYSA-N 0.000 description 1
- FFJDUFAVRTYGHA-UHFFFAOYSA-N 4-[1-(2-chlorobenzoyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound ClC1=CC=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C1 FFJDUFAVRTYGHA-UHFFFAOYSA-N 0.000 description 1
- LFKORWSXAZYKAR-UHFFFAOYSA-N 4-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound ClC1=CC=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 LFKORWSXAZYKAR-UHFFFAOYSA-N 0.000 description 1
- LQWCPXWQEOBGJN-UHFFFAOYSA-N 4-[1-(2-chloropyridine-3-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound ClC1=NC=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 LQWCPXWQEOBGJN-UHFFFAOYSA-N 0.000 description 1
- FAAPEUCTUOLSDJ-UHFFFAOYSA-N 4-[1-(2-cyanobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CC=C1C#N FAAPEUCTUOLSDJ-UHFFFAOYSA-N 0.000 description 1
- XBQQBEPKDKKZQX-UHFFFAOYSA-N 4-[1-(2-cyclohexylacetyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1C(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)CC1CCCCC1 XBQQBEPKDKKZQX-UHFFFAOYSA-N 0.000 description 1
- DBKNIOVSSNNTHT-UHFFFAOYSA-N 4-[1-(2-cyclohexylacetyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)CC1CCCCC1 DBKNIOVSSNNTHT-UHFFFAOYSA-N 0.000 description 1
- UDYZHGTWJMDAOG-UHFFFAOYSA-N 4-[1-(2-cyclohexyloxyacetyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)COC1CCCCC1 UDYZHGTWJMDAOG-UHFFFAOYSA-N 0.000 description 1
- ZFOWTRZRFVZCLN-UHFFFAOYSA-N 4-[1-(2-cyclopentylacetyl)-3,6-dihydro-2h-pyridin-4-yl]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)=CCN1C(=O)CC1CCCC1 ZFOWTRZRFVZCLN-UHFFFAOYSA-N 0.000 description 1
- UDOUAAXCLYELIN-UHFFFAOYSA-N 4-[1-(2-cyclopentylacetyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1C(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)CC1CCCC1 UDOUAAXCLYELIN-UHFFFAOYSA-N 0.000 description 1
- FTIIKUKTXFDNIT-UHFFFAOYSA-N 4-[1-(2-cyclopentylacetyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)CC1CCCC1 FTIIKUKTXFDNIT-UHFFFAOYSA-N 0.000 description 1
- XBNANYVTWZMMCU-UHFFFAOYSA-N 4-[1-(2-cyclopentylpyrazole-3-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=NN1C1CCCC1 XBNANYVTWZMMCU-UHFFFAOYSA-N 0.000 description 1
- LQSMGHNHTAVULX-UHFFFAOYSA-N 4-[1-(2-cyclopropyl-1,3-thiazole-5-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C(S1)=CN=C1C1CC1 LQSMGHNHTAVULX-UHFFFAOYSA-N 0.000 description 1
- CMLCANFBOOBJKP-UHFFFAOYSA-N 4-[1-(2-cyclopropylacetyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1C(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)CC1CC1 CMLCANFBOOBJKP-UHFFFAOYSA-N 0.000 description 1
- ODACPEPHWXSVLP-UHFFFAOYSA-N 4-[1-(2-cyclopropylacetyl)azetidin-3-yl]oxy-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1C(OC=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)CC1CC1 ODACPEPHWXSVLP-UHFFFAOYSA-N 0.000 description 1
- BCLJFSGLGKMAOT-UHFFFAOYSA-N 4-[1-(2-cyclopropylacetyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)CC1CC1 BCLJFSGLGKMAOT-UHFFFAOYSA-N 0.000 description 1
- BULHRCJZAHLFCI-UHFFFAOYSA-N 4-[1-(2-cyclopropylacetyl)piperidin-4-yl]oxy-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C1CC(OC=2C=CC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)CCN1C(=O)CC1CC1 BULHRCJZAHLFCI-UHFFFAOYSA-N 0.000 description 1
- BFOVRAZCDNEDPH-UHFFFAOYSA-N 4-[1-(2-cyclopropylacetyl)piperidin-4-yl]oxy-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CC(OC=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)CC1CC1 BFOVRAZCDNEDPH-UHFFFAOYSA-N 0.000 description 1
- OJYMULYCMPKLKG-UHFFFAOYSA-N 4-[1-(2-cyclopropylacetyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)CC1CC1 OJYMULYCMPKLKG-UHFFFAOYSA-N 0.000 description 1
- FLVOHPRPYOOPOP-UHFFFAOYSA-N 4-[1-(2-ethoxypyridine-4-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=NC(OCC)=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 FLVOHPRPYOOPOP-UHFFFAOYSA-N 0.000 description 1
- XUFGMRGXSSCJKQ-UHFFFAOYSA-N 4-[1-(2-ethyl-1,3-thiazole-4-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound S1C(CC)=NC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 XUFGMRGXSSCJKQ-UHFFFAOYSA-N 0.000 description 1
- KLVTZPRMZQORES-UHFFFAOYSA-N 4-[1-(2-ethylbutanoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CN(C(=O)C(CC)CC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 KLVTZPRMZQORES-UHFFFAOYSA-N 0.000 description 1
- PFLWMLJCXHIZNQ-UHFFFAOYSA-N 4-[1-(2-fluorobenzoyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C1 PFLWMLJCXHIZNQ-UHFFFAOYSA-N 0.000 description 1
- ALNHAFCOQQRADI-UHFFFAOYSA-N 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide Chemical compound FC1=CC=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC=2N=CC3=NC=CN3C=2)CC1 ALNHAFCOQQRADI-UHFFFAOYSA-N 0.000 description 1
- IDJSZXRPIPLVQF-UHFFFAOYSA-N 4-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 IDJSZXRPIPLVQF-UHFFFAOYSA-N 0.000 description 1
- XEPLOZUERLNWLQ-UHFFFAOYSA-N 4-[1-(2-hydroxy-2-methylpropanoyl)-3,6-dihydro-2h-pyridin-4-yl]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C1N(C(=O)C(C)(O)C)CCC(C=2C=CC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)=C1 XEPLOZUERLNWLQ-UHFFFAOYSA-N 0.000 description 1
- BVOORWQCEOZXJM-UHFFFAOYSA-N 4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1N(C(=O)C(C)(O)C)CC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 BVOORWQCEOZXJM-UHFFFAOYSA-N 0.000 description 1
- DUMFYCVCDUBSPA-UHFFFAOYSA-N 4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CN(C(=O)C(C)(O)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 DUMFYCVCDUBSPA-UHFFFAOYSA-N 0.000 description 1
- JJOIXGLFPRBPFT-UHFFFAOYSA-N 4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C1CN(C(=O)C(C)(O)C)CCC1OC1=CC=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=C1 JJOIXGLFPRBPFT-UHFFFAOYSA-N 0.000 description 1
- IKRMJBOLBMHCSI-UHFFFAOYSA-N 4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CN(C(=O)C(C)(O)C)CCC1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 IKRMJBOLBMHCSI-UHFFFAOYSA-N 0.000 description 1
- QRUYSCCYOSCMTF-UHFFFAOYSA-N 4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1N(C(=O)C(C)(O)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 QRUYSCCYOSCMTF-UHFFFAOYSA-N 0.000 description 1
- IUZJEPPWXLABKN-UHFFFAOYSA-N 4-[1-(2-hydroxy-2-methylpropyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=NN(CC(C)(O)C)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 IUZJEPPWXLABKN-UHFFFAOYSA-N 0.000 description 1
- BDWVIWYYQJFYLB-UHFFFAOYSA-N 4-[1-(2-tert-butyl-5-methylpyrazole-3-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound CC(C)(C)N1N=C(C)C=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 BDWVIWYYQJFYLB-UHFFFAOYSA-N 0.000 description 1
- IUGRKBZPLBFNDJ-UHFFFAOYSA-N 4-[1-(2h-chromene-3-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CC=C2OCC(C(=O)N3CCC(CC3)C3=CC=C(C=C3)C(NCC3=CC4=NC=CN4C=C3)=O)=CC2=C1 IUGRKBZPLBFNDJ-UHFFFAOYSA-N 0.000 description 1
- MYOKROAKEMYXBR-UHFFFAOYSA-N 4-[1-(3,3-difluorocyclobutanecarbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1C(F)(F)CC1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 MYOKROAKEMYXBR-UHFFFAOYSA-N 0.000 description 1
- ACKRRFMXOPONKK-UHFFFAOYSA-N 4-[1-(3,3-dimethylbutanoyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1N(C(=O)CC(C)(C)C)CC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 ACKRRFMXOPONKK-UHFFFAOYSA-N 0.000 description 1
- GZISDTYFUGWFFR-UHFFFAOYSA-N 4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CN(C(=O)CC(C)(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 GZISDTYFUGWFFR-UHFFFAOYSA-N 0.000 description 1
- RLYRDRNMDUVCGX-UHFFFAOYSA-N 4-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1N(C(=O)CC(C)(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 RLYRDRNMDUVCGX-UHFFFAOYSA-N 0.000 description 1
- UMSBZPSGDFSOTK-UHFFFAOYSA-N 4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=C(F)C(F)=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 UMSBZPSGDFSOTK-UHFFFAOYSA-N 0.000 description 1
- AUSUIHYXTSPUNE-UHFFFAOYSA-N 4-[1-(3,4-dihydro-2h-chromene-6-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound O1CCCC2=CC(C(=O)N3CCC(CC3)C3=CC=C(C=C3)C(NCC3=CC4=NC=CN4C=C3)=O)=CC=C21 AUSUIHYXTSPUNE-UHFFFAOYSA-N 0.000 description 1
- XRRNMNJOXRYGDS-UHFFFAOYSA-N 4-[1-(3,4-dihydro-2h-pyrano[2,3-b]pyridine-6-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound O1CCCC2=CC(C(=O)N3CCC(CC3)C3=CC=C(C=C3)C(NCC3=CC4=NC=CN4C=C3)=O)=CN=C21 XRRNMNJOXRYGDS-UHFFFAOYSA-N 0.000 description 1
- BSCKROYLLNDCOC-UHFFFAOYSA-N 4-[1-(3,5-difluorobenzoyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC(F)=CC(C(=O)N2CC(C2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 BSCKROYLLNDCOC-UHFFFAOYSA-N 0.000 description 1
- LLJBCOWHEXSBMG-UHFFFAOYSA-N 4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC(F)=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 LLJBCOWHEXSBMG-UHFFFAOYSA-N 0.000 description 1
- XRDJXQASBRCUNN-UHFFFAOYSA-N 4-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC(F)=CC(C(=O)N2CC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 XRDJXQASBRCUNN-UHFFFAOYSA-N 0.000 description 1
- MIXCBTNZUMHUAX-UHFFFAOYSA-N 4-[1-(3,5-difluoropyridine-2-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC(F)=CN=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 MIXCBTNZUMHUAX-UHFFFAOYSA-N 0.000 description 1
- AZXZHUQSMBDTIL-UHFFFAOYSA-N 4-[1-(3,5-dimethyl-1,2-oxazole-4-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound CC1=NOC(C)=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 AZXZHUQSMBDTIL-UHFFFAOYSA-N 0.000 description 1
- IFOYAKGVZWBDQQ-UHFFFAOYSA-N 4-[1-(3-chloro-5-cyanopyridine-2-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound ClC1=CC(C#N)=CN=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 IFOYAKGVZWBDQQ-UHFFFAOYSA-N 0.000 description 1
- MJESZMNSUXQGRZ-UHFFFAOYSA-N 4-[1-(3-chlorobenzoyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound ClC1=CC=CC(C(=O)N2CC(C2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 MJESZMNSUXQGRZ-UHFFFAOYSA-N 0.000 description 1
- PNVPXEBEDMOTJM-UHFFFAOYSA-N 4-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound ClC1=CC=CC(C(=O)N2CC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 PNVPXEBEDMOTJM-UHFFFAOYSA-N 0.000 description 1
- WDQRAJXLPUJAIV-UHFFFAOYSA-N 4-[1-(3-chloropyridine-2-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound ClC1=CC=CN=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 WDQRAJXLPUJAIV-UHFFFAOYSA-N 0.000 description 1
- ZILLWTSBHHFREU-UHFFFAOYSA-N 4-[1-(3-cyanobenzoyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C1=CC=CC(C#N)=C1 ZILLWTSBHHFREU-UHFFFAOYSA-N 0.000 description 1
- ZFNNKGBKOFYOEE-UHFFFAOYSA-N 4-[1-(3-cyanobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CC(C#N)=C1 ZFNNKGBKOFYOEE-UHFFFAOYSA-N 0.000 description 1
- CIYCOVYRLLBDBH-UHFFFAOYSA-N 4-[1-(3-cyanobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C1=CC=CC(C#N)=C1 CIYCOVYRLLBDBH-UHFFFAOYSA-N 0.000 description 1
- OGQPPZWZYZYXAI-UHFFFAOYSA-N 4-[1-(3-cyanothiophene-2-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C=1SC=CC=1C#N OGQPPZWZYZYXAI-UHFFFAOYSA-N 0.000 description 1
- DKLOVCUPYYAKMJ-UHFFFAOYSA-N 4-[1-(3-cyclopropyl-1,2-oxazole-5-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C(ON=1)=CC=1C1CC1 DKLOVCUPYYAKMJ-UHFFFAOYSA-N 0.000 description 1
- XXPFHVVKSURDBC-UHFFFAOYSA-N 4-[1-(3-ethyl-1,2-oxazole-5-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound O1N=C(CC)C=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 XXPFHVVKSURDBC-UHFFFAOYSA-N 0.000 description 1
- ITFSQDGDQLJZIL-UHFFFAOYSA-N 4-[1-(3-fluoro-6-methylpyridine-2-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound CC1=CC=C(F)C(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=N1 ITFSQDGDQLJZIL-UHFFFAOYSA-N 0.000 description 1
- LXSNWNMURQVOKK-UHFFFAOYSA-N 4-[1-(3-fluorobenzoyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC=CC(C(=O)N2CC(C2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 LXSNWNMURQVOKK-UHFFFAOYSA-N 0.000 description 1
- HNYAAHJEHCYZLM-UHFFFAOYSA-N 4-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC=CC(C(=O)N2CC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 HNYAAHJEHCYZLM-UHFFFAOYSA-N 0.000 description 1
- SJXJYJZMUCAUJF-UHFFFAOYSA-N 4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)C(CO)C1=CC=CC=C1 SJXJYJZMUCAUJF-UHFFFAOYSA-N 0.000 description 1
- HOSXOSJFCKJJPL-UHFFFAOYSA-N 4-[1-(4,4-difluorocyclohexanecarbonyl)-3,6-dihydro-2h-pyridin-4-yl]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C1CC(F)(F)CCC1C(=O)N1CC=C(C=2C=CC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)CC1 HOSXOSJFCKJJPL-UHFFFAOYSA-N 0.000 description 1
- UJLDXMCQHOTOHQ-UHFFFAOYSA-N 4-[1-(4,4-difluorocyclohexanecarbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CC(F)(F)CCC1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 UJLDXMCQHOTOHQ-UHFFFAOYSA-N 0.000 description 1
- AUWFENQPEWZIAH-UHFFFAOYSA-N 4-[1-(4-chloro-1,3-thiazole-5-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound N1=CSC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1Cl AUWFENQPEWZIAH-UHFFFAOYSA-N 0.000 description 1
- HWJDZSDQHQPUSH-UHFFFAOYSA-N 4-[1-(4-chloro-2,5-dimethylpyrazole-3-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound CC1=NN(C)C(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1Cl HWJDZSDQHQPUSH-UHFFFAOYSA-N 0.000 description 1
- SCFQCMZAQHAOHB-UHFFFAOYSA-N 4-[1-(4-chlorobenzoyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C1 SCFQCMZAQHAOHB-UHFFFAOYSA-N 0.000 description 1
- GLTDKQYTQUALTI-UHFFFAOYSA-N 4-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 GLTDKQYTQUALTI-UHFFFAOYSA-N 0.000 description 1
- YSDLEMTVKQHRKY-UHFFFAOYSA-N 4-[1-(4-cyanobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=C(C#N)C=C1 YSDLEMTVKQHRKY-UHFFFAOYSA-N 0.000 description 1
- FLGHVRGWTVJULS-UHFFFAOYSA-N 4-[1-(4-cyanothiophene-2-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC(C#N)=CS1 FLGHVRGWTVJULS-UHFFFAOYSA-N 0.000 description 1
- XCPKEGFDZALBLN-UHFFFAOYSA-N 4-[1-(4-fluorobenzoyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C1 XCPKEGFDZALBLN-UHFFFAOYSA-N 0.000 description 1
- MOZWAXOHYBSQCS-UHFFFAOYSA-N 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide Chemical compound C1=CC(F)=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC=2N=CC3=NC=CN3C=2)CC1 MOZWAXOHYBSQCS-UHFFFAOYSA-N 0.000 description 1
- RCVWLOKNBAKKPU-UHFFFAOYSA-N 4-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 RCVWLOKNBAKKPU-UHFFFAOYSA-N 0.000 description 1
- KVZGLDNSTBRKSE-UHFFFAOYSA-N 4-[1-(5,6-dimethoxypyridine-2-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound N1=C(OC)C(OC)=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 KVZGLDNSTBRKSE-UHFFFAOYSA-N 0.000 description 1
- XMADOWHPVBDRNX-UHFFFAOYSA-N 4-[1-(5,6-dimethylpyridine-3-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound N1=C(C)C(C)=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 XMADOWHPVBDRNX-UHFFFAOYSA-N 0.000 description 1
- MUKROUDUFVOKJC-UHFFFAOYSA-N 4-[1-(5-cyanothiophene-2-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=C(C#N)S1 MUKROUDUFVOKJC-UHFFFAOYSA-N 0.000 description 1
- ZFVMVTWEWZOMOO-UHFFFAOYSA-N 4-[1-(5-cyclopropyl-1,2-oxazole-3-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C(=NO1)C=C1C1CC1 ZFVMVTWEWZOMOO-UHFFFAOYSA-N 0.000 description 1
- HTLSSLMIIFCRJQ-UHFFFAOYSA-N 4-[1-(5-cyclopropyl-2-methylpyrazole-3-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=C(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)N(C)N=C1C1CC1 HTLSSLMIIFCRJQ-UHFFFAOYSA-N 0.000 description 1
- HIHJOPFLPDKGBV-UHFFFAOYSA-N 4-[1-(5-cyclopropylpyridine-2-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C(N=C1)=CC=C1C1CC1 HIHJOPFLPDKGBV-UHFFFAOYSA-N 0.000 description 1
- JAODMPKYBAWIHL-UHFFFAOYSA-N 4-[1-(5-ethylpyridine-2-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound N1=CC(CC)=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 JAODMPKYBAWIHL-UHFFFAOYSA-N 0.000 description 1
- MAPYIPDQZVNNMG-UHFFFAOYSA-N 4-[1-(benzenesulfonyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1S(=O)(=O)C1=CC=CC=C1 MAPYIPDQZVNNMG-UHFFFAOYSA-N 0.000 description 1
- UVRBJLSPRMPKJV-UHFFFAOYSA-N 4-[1-(benzenesulfonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide Chemical compound C=1N2C=CN=C2C=NC=1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 UVRBJLSPRMPKJV-UHFFFAOYSA-N 0.000 description 1
- XAYSCQKUWSORPL-UHFFFAOYSA-N 4-[1-(benzenesulfonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 XAYSCQKUWSORPL-UHFFFAOYSA-N 0.000 description 1
- HEZVWEKUYVBCHE-UHFFFAOYSA-N 4-[1-(benzenesulfonyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1S(=O)(=O)C1=CC=CC=C1 HEZVWEKUYVBCHE-UHFFFAOYSA-N 0.000 description 1
- PWCRZBZYVBRDHR-UHFFFAOYSA-N 4-[1-(cyclohex-3-ene-1-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1CCC=CC1 PWCRZBZYVBRDHR-UHFFFAOYSA-N 0.000 description 1
- ZWYLWWCOPUNZHI-UHFFFAOYSA-N 4-[1-(cyclohexanecarbonyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C1CCCCC1 ZWYLWWCOPUNZHI-UHFFFAOYSA-N 0.000 description 1
- CPMCYCURXKUKMR-UHFFFAOYSA-N 4-[1-(cyclohexanecarbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1CCCCC1 CPMCYCURXKUKMR-UHFFFAOYSA-N 0.000 description 1
- VAQSWTIGDPPVOH-UHFFFAOYSA-N 4-[1-(cyclohexanecarbonyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C1CCCCC1 VAQSWTIGDPPVOH-UHFFFAOYSA-N 0.000 description 1
- PDSTTXPCCNIFHY-UHFFFAOYSA-N 4-[1-(cyclopentanecarbonyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C1CCCC1 PDSTTXPCCNIFHY-UHFFFAOYSA-N 0.000 description 1
- AULGFFSQKMDEBL-UHFFFAOYSA-N 4-[1-(cyclopentanecarbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1CCCC1 AULGFFSQKMDEBL-UHFFFAOYSA-N 0.000 description 1
- VNSCEPGLFIMQET-UHFFFAOYSA-N 4-[1-(cyclopentanecarbonyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C1CCCC1 VNSCEPGLFIMQET-UHFFFAOYSA-N 0.000 description 1
- RUWAAPMJKKLQJB-UHFFFAOYSA-N 4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1CC1 RUWAAPMJKKLQJB-UHFFFAOYSA-N 0.000 description 1
- IYCJJGDEQCDZNE-UHFFFAOYSA-N 4-[1-(cyclopropanecarbonyl)piperidin-4-yl]oxy-n-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(C=C1)=CC=C1OC(CC1)CCN1C(=O)C1CC1 IYCJJGDEQCDZNE-UHFFFAOYSA-N 0.000 description 1
- WBVICLZNTMVYGF-UHFFFAOYSA-N 4-[1-(furan-2-carbonyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C1=CC=CO1 WBVICLZNTMVYGF-UHFFFAOYSA-N 0.000 description 1
- LEVSJVWKZYETRG-UHFFFAOYSA-N 4-[1-(furan-2-carbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CO1 LEVSJVWKZYETRG-UHFFFAOYSA-N 0.000 description 1
- MRUJSDKERFKWFZ-UHFFFAOYSA-N 4-[1-(furan-2-carbonyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C1=CC=CO1 MRUJSDKERFKWFZ-UHFFFAOYSA-N 0.000 description 1
- HWEACVJTAHEGTO-UHFFFAOYSA-N 4-[1-(furan-3-carbonyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C=1C=COC=1 HWEACVJTAHEGTO-UHFFFAOYSA-N 0.000 description 1
- LWAMXGQVOWFEOB-UHFFFAOYSA-N 4-[1-(furan-3-carbonyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C=1C=COC=1 LWAMXGQVOWFEOB-UHFFFAOYSA-N 0.000 description 1
- AVVBNDNDKHEZOI-UHFFFAOYSA-N 4-[1-[1-(difluoromethyl)-5-methylpyrazole-3-carbonyl]piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC(F)N1C(C)=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=N1 AVVBNDNDKHEZOI-UHFFFAOYSA-N 0.000 description 1
- MSMSCGJLQXSLOD-UHFFFAOYSA-N 4-[1-[2-(2-chloropyridin-3-yl)acetyl]piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound ClC1=NC=CC=C1CC(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 MSMSCGJLQXSLOD-UHFFFAOYSA-N 0.000 description 1
- BCSWPXRHGVBIIA-UHFFFAOYSA-N 4-[1-[2-(2-ethylpiperidin-1-yl)-2-oxoacetyl]piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound CCC1CCCCN1C(=O)C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 BCSWPXRHGVBIIA-UHFFFAOYSA-N 0.000 description 1
- AAEPCASWPNXWPZ-UHFFFAOYSA-N 4-[1-[2-(3-cyclopropylpyrazol-1-yl)propanoyl]piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)C(C)N(N=1)C=CC=1C1CC1 AAEPCASWPNXWPZ-UHFFFAOYSA-N 0.000 description 1
- NVHATXDJZOTPML-UHFFFAOYSA-N 4-[1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)C(C)OC1=CC=CC(F)=C1 NVHATXDJZOTPML-UHFFFAOYSA-N 0.000 description 1
- IVFIIPIGAVNEEM-UHFFFAOYSA-N 4-[1-[2-(4-cyanophenyl)acetyl]piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)CC1=CC=C(C#N)C=C1 IVFIIPIGAVNEEM-UHFFFAOYSA-N 0.000 description 1
- OKIUWKQDHLGJNZ-UHFFFAOYSA-N 4-[1-[2-(4-fluorophenoxy)acetyl]piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CC(F)=CC=C1OCC(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 OKIUWKQDHLGJNZ-UHFFFAOYSA-N 0.000 description 1
- BWYISUKMVJSJDC-UHFFFAOYSA-N 4-[1-[2-(difluoromethyl)pyrazole-3-carbonyl]piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC(F)N1N=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 BWYISUKMVJSJDC-UHFFFAOYSA-N 0.000 description 1
- YQJSMARIHGHXNS-UHFFFAOYSA-N 4-[1-[3-(diethylamino)propanoyl]piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1CN(C(=O)CCN(CC)CC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 YQJSMARIHGHXNS-UHFFFAOYSA-N 0.000 description 1
- YPKKMTVQNYMINT-UHFFFAOYSA-N 4-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenyl]-n,n-dimethylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 YPKKMTVQNYMINT-UHFFFAOYSA-N 0.000 description 1
- PAKSPSTYDQVVHH-UHFFFAOYSA-N 4-[[2-(2,4-difluorophenyl)acetyl]amino]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC(F)=CC=C1CC(=O)NC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 PAKSPSTYDQVVHH-UHFFFAOYSA-N 0.000 description 1
- XRCAGSQGSVMBHO-UHFFFAOYSA-N 4-[[2-(2,5-difluorophenyl)acetyl]amino]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC=C(F)C(CC(=O)NC=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 XRCAGSQGSVMBHO-UHFFFAOYSA-N 0.000 description 1
- ZNPVDSDPLXHMRG-UHFFFAOYSA-N 4-[[2-(2-fluorophenyl)acetyl]amino]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound FC1=CC=CC=C1CC(=O)NC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 ZNPVDSDPLXHMRG-UHFFFAOYSA-N 0.000 description 1
- YUUPCIMSHGTJLT-UHFFFAOYSA-N 4-benzamido-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1 YUUPCIMSHGTJLT-UHFFFAOYSA-N 0.000 description 1
- SXYYQOAFVXYGNM-UHFFFAOYSA-N 4-chloro-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=NN(CC(C)C)C=C1C1=C(Cl)C=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 SXYYQOAFVXYGNM-UHFFFAOYSA-N 0.000 description 1
- IHSNCIATFHFQDS-OAHLLOKOSA-N 4-chloro-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[[(3r)-oxolan-3-yl]methyl]pyrazol-4-yl]thiophene-2-carboxamide Chemical compound ClC=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)SC=1C(=C1)C=NN1C[C@H]1CCOC1 IHSNCIATFHFQDS-OAHLLOKOSA-N 0.000 description 1
- UYMIYCMQGRZIOO-UHFFFAOYSA-N 4-n-(imidazo[1,2-a]pyridin-6-ylmethyl)-1-n-(3-methylbutyl)benzene-1,4-dicarboxamide Chemical compound C1=CC(C(=O)NCCC(C)C)=CC=C1C(=O)NCC1=CN2C=CN=C2C=C1 UYMIYCMQGRZIOO-UHFFFAOYSA-N 0.000 description 1
- AGDVOLAHIWEGNN-INIZCTEOSA-N 4-n-(imidazo[1,2-a]pyridin-6-ylmethyl)-1-n-[[(3s)-oxolan-3-yl]methyl]benzene-1,4-dicarboxamide Chemical compound C=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=CC=1C(=O)NC[C@@H]1CCOC1 AGDVOLAHIWEGNN-INIZCTEOSA-N 0.000 description 1
- GAIJTSVFBCDRMC-UHFFFAOYSA-N 4-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1-n-(3-methylbutyl)benzene-1,4-dicarboxamide Chemical compound C1=CC(C(=O)NCCC(C)C)=CC=C1C(=O)NCC1=CC2=NC=CN2C=C1 GAIJTSVFBCDRMC-UHFFFAOYSA-N 0.000 description 1
- QGKMOPIEZUEPPB-INIZCTEOSA-N 4-n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1-n-[[(3s)-oxolan-3-yl]methyl]benzene-1,4-dicarboxamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=CC=1C(=O)NC[C@@H]1CCOC1 QGKMOPIEZUEPPB-INIZCTEOSA-N 0.000 description 1
- IFKSCJGSSCJKBL-UHFFFAOYSA-N 4-n-[(2,5-difluorophenyl)methyl]-1-n-(imidazo[1,2-a]pyridin-7-ylmethyl)benzene-1,4-dicarboxamide Chemical compound FC1=CC=C(F)C(CNC(=O)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 IFKSCJGSSCJKBL-UHFFFAOYSA-N 0.000 description 1
- 125000002471 4H-quinolizinyl group Chemical group C=1(C=CCN2C=CC=CC12)* 0.000 description 1
- CODVONFVQKMUHW-UHFFFAOYSA-N 5-(1-acetyl-3,6-dihydro-2h-pyridin-4-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1N(C(=O)C)CCC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 CODVONFVQKMUHW-UHFFFAOYSA-N 0.000 description 1
- YINMPEZYZNZKGP-UHFFFAOYSA-N 5-(1-acetylpiperidin-4-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1CN(C(=O)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 YINMPEZYZNZKGP-UHFFFAOYSA-N 0.000 description 1
- IHWMVSRAIPBHOX-UHFFFAOYSA-N 5-(1-benzamidocyclobutyl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C1(NC(=O)C=2C=CC=CC=2)CCC1 IHWMVSRAIPBHOX-UHFFFAOYSA-N 0.000 description 1
- IIJDWTYALGCHQY-UHFFFAOYSA-N 5-(1-benzoyl-3,6-dihydro-2h-pyridin-4-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(O1)=CC=C1C(CC1)=CCN1C(=O)C1=CC=CC=C1 IIJDWTYALGCHQY-UHFFFAOYSA-N 0.000 description 1
- YZWKRHDTEOBWFU-UHFFFAOYSA-N 5-(1-benzoyl-3-hydroxyazetidin-3-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1C(O)(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)C1=CC=CC=C1 YZWKRHDTEOBWFU-UHFFFAOYSA-N 0.000 description 1
- KUMDAJGRFLWHKU-UHFFFAOYSA-N 5-(1-benzoyl-4-hydroxypiperidin-4-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1CC(O)(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)C1=CC=CC=C1 KUMDAJGRFLWHKU-UHFFFAOYSA-N 0.000 description 1
- WVXDQZRWBWUQJW-UHFFFAOYSA-N 5-(1-benzoylpyrrolidin-3-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(C1)CCN1C(=O)C1=CC=CC=C1 WVXDQZRWBWUQJW-UHFFFAOYSA-N 0.000 description 1
- INZAEIQEIGKQBN-UHFFFAOYSA-N 5-(1-benzylpyrazol-4-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(O1)=CC=C1C(=C1)C=NN1CC1=CC=CC=C1 INZAEIQEIGKQBN-UHFFFAOYSA-N 0.000 description 1
- UREIGWLITVJBCT-UHFFFAOYSA-N 5-(1-benzylpyrazol-4-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1=CC=CC=C1 UREIGWLITVJBCT-UHFFFAOYSA-N 0.000 description 1
- WKHOLJKXUVCULJ-UHFFFAOYSA-N 5-(1-butanoylpyrrolidin-3-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1N(C(=O)CCC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 WKHOLJKXUVCULJ-UHFFFAOYSA-N 0.000 description 1
- UGCXQJRUIKTWKL-UHFFFAOYSA-N 5-(1-cyclopropylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(CC1)=CCN1S(=O)(=O)C1CC1 UGCXQJRUIKTWKL-UHFFFAOYSA-N 0.000 description 1
- DTTOWMFHCQOBCP-UHFFFAOYSA-N 5-(1-ethylpyrazol-4-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=NN(CC)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 DTTOWMFHCQOBCP-UHFFFAOYSA-N 0.000 description 1
- SGBHJKPPQXPZSL-UHFFFAOYSA-N 5-(1-propan-2-ylsulfonylpiperidin-4-yl)-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1CN(S(=O)(=O)C(C)C)CCC1C1=CC=C(C(=O)NCC2=CN3N=CN=C3C=C2)S1 SGBHJKPPQXPZSL-UHFFFAOYSA-N 0.000 description 1
- DYHHZSABBJWEHJ-UHFFFAOYSA-N 5-(2-benzyl-5-cyclopropylpyrazol-3-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C1=CC(C2CC2)=NN1CC1=CC=CC=C1 DYHHZSABBJWEHJ-UHFFFAOYSA-N 0.000 description 1
- SFFXVSAHGFUTSD-UHFFFAOYSA-N 5-(3-benzamidooxetan-3-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C1(NC(=O)C=2C=CC=CC=2)COC1 SFFXVSAHGFUTSD-UHFFFAOYSA-N 0.000 description 1
- QTCBQXURCJHIGF-UHFFFAOYSA-N 5-(4-hydroxyoxan-4-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)SC=1C1(O)CCOCC1 QTCBQXURCJHIGF-UHFFFAOYSA-N 0.000 description 1
- NZPXMPZLYBCKLY-UHFFFAOYSA-N 5-(5-cyclopropyl-2-methylpyrazol-3-yl)-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=C(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)N(C)N=C1C1CC1 NZPXMPZLYBCKLY-UHFFFAOYSA-N 0.000 description 1
- SZWKGOSGBKUUCL-QGZVFWFLSA-N 5-[(1r)-1-(cyclopropanecarbonylamino)-3-methylbutyl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound N([C@H](CC(C)C)C=1SC(=CC=1)C(=O)NCC1=CC2=NC=CN2C=C1)C(=O)C1CC1 SZWKGOSGBKUUCL-QGZVFWFLSA-N 0.000 description 1
- SZWKGOSGBKUUCL-KRWDZBQOSA-N 5-[(1s)-1-(cyclopropanecarbonylamino)-3-methylbutyl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound N([C@@H](CC(C)C)C=1SC(=CC=1)C(=O)NCC1=CC2=NC=CN2C=C1)C(=O)C1CC1 SZWKGOSGBKUUCL-KRWDZBQOSA-N 0.000 description 1
- VQPGQPMDMVVHNT-GFCCVEGCSA-N 5-[(4r)-4-hydroxy-2-oxopyrrolidin-1-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound O=C1C[C@@H](O)CN1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 VQPGQPMDMVVHNT-GFCCVEGCSA-N 0.000 description 1
- VQPGQPMDMVVHNT-LBPRGKRZSA-N 5-[(4s)-4-hydroxy-2-oxopyrrolidin-1-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound O=C1C[C@H](O)CN1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 VQPGQPMDMVVHNT-LBPRGKRZSA-N 0.000 description 1
- FACYWRVJXDAPDH-UHFFFAOYSA-N 5-[1-(1,1-dioxothiolan-3-yl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1C1CCS(=O)(=O)C1 FACYWRVJXDAPDH-UHFFFAOYSA-N 0.000 description 1
- MCOPFFICBVDDQH-UHFFFAOYSA-N 5-[1-(1,4-dioxan-2-ylmethyl)pyrazol-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CC2=NC=NN2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1COCCO1 MCOPFFICBVDDQH-UHFFFAOYSA-N 0.000 description 1
- XIBROPLBNGCITA-UHFFFAOYSA-N 5-[1-(1,4-dioxan-2-ylmethyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1COCCO1 XIBROPLBNGCITA-UHFFFAOYSA-N 0.000 description 1
- GVWKOUYWDWJUHC-UHFFFAOYSA-N 5-[1-(1-cyanocyclopropanecarbonyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(C1)CCN1C(=O)C1(C#N)CC1 GVWKOUYWDWJUHC-UHFFFAOYSA-N 0.000 description 1
- BYHAIZHLPURSCC-UHFFFAOYSA-N 5-[1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1CC(C=2SC(=CC=2)C(=O)NCC2=CN3N=CN=C3C=C2)CCN1C(=O)C1(C)CC1 BYHAIZHLPURSCC-UHFFFAOYSA-N 0.000 description 1
- YCCLPOHACUMPKA-UHFFFAOYSA-N 5-[1-(1-methylpiperidine-4-carbonyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1CN(C)CCC1C(=O)N1CCC(C=2SC(=CC=2)C(=O)NCC2=CN3N=CN=C3C=C2)CC1 YCCLPOHACUMPKA-UHFFFAOYSA-N 0.000 description 1
- ARXVJSLNKVLCMZ-UHFFFAOYSA-N 5-[1-(2,2-dimethyl-3-piperazin-1-ylpropyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=C(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C=NN1CC(C)(C)CN1CCNCC1 ARXVJSLNKVLCMZ-UHFFFAOYSA-N 0.000 description 1
- XMEWEISJPLWBMS-UHFFFAOYSA-N 5-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1N(C(=O)C(C)(C)CC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 XMEWEISJPLWBMS-UHFFFAOYSA-N 0.000 description 1
- QLNFAGDKGSYPKN-UHFFFAOYSA-N 5-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1N(C(=O)C(C)(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 QLNFAGDKGSYPKN-UHFFFAOYSA-N 0.000 description 1
- GMCSVPTVOGJDQS-UHFFFAOYSA-N 5-[1-(2,2-dimethylpropyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1=NN(CC(C)(C)C)C=C1C1=CC=C(C(=O)NCC=2N=CC3=NC=CN3C=2)S1 GMCSVPTVOGJDQS-UHFFFAOYSA-N 0.000 description 1
- FLUXWBNUPQZEMC-UHFFFAOYSA-N 5-[1-(2,2-dimethylpropyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide Chemical compound C1=NN(CC(C)(C)C)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)O1 FLUXWBNUPQZEMC-UHFFFAOYSA-N 0.000 description 1
- DMVWIDMLLYCIBK-UHFFFAOYSA-N 5-[1-(2,2-dimethylpropyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=NN(CC(C)(C)C)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 DMVWIDMLLYCIBK-UHFFFAOYSA-N 0.000 description 1
- QLBHUQMVBSIMKU-UHFFFAOYSA-N 5-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1N(C(=O)C(C)C(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 QLBHUQMVBSIMKU-UHFFFAOYSA-N 0.000 description 1
- HOSHFIQSKJKIBT-UHFFFAOYSA-N 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC(F)=CC=C1C(=O)N1CCC(C=2SC(=CC=2)C(=O)NCC2=CN3N=CN=C3C=C2)CC1 HOSHFIQSKJKIBT-UHFFFAOYSA-N 0.000 description 1
- RYWLAHLHMDJYQY-UHFFFAOYSA-N 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC(F)=CC=C1C(=O)N1CCC(C=2SC(=CC=2)C(=O)NCC=2N=CC3=NC=CN3C=2)CC1 RYWLAHLHMDJYQY-UHFFFAOYSA-N 0.000 description 1
- MIFHKZGFUXAEEU-UHFFFAOYSA-N 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC(F)=CC=C1C(=O)N1CCC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 MIFHKZGFUXAEEU-UHFFFAOYSA-N 0.000 description 1
- FHUGKFGNHYQZBI-UHFFFAOYSA-N 5-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC(F)=CC=C1C(=O)N1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 FHUGKFGNHYQZBI-UHFFFAOYSA-N 0.000 description 1
- CUFYHDQKHSTGOV-UHFFFAOYSA-N 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC=C(F)C(C(=O)N2CCC(CC2)C=2SC(=CC=2)C(=O)NCC2=CN3N=CN=C3C=C2)=C1 CUFYHDQKHSTGOV-UHFFFAOYSA-N 0.000 description 1
- IUMYQPDLGZZPQK-UHFFFAOYSA-N 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC=C(F)C(C(=O)N2CCC(CC2)C=2SC(=CC=2)C(=O)NCC=2N=CC3=NC=CN3C=2)=C1 IUMYQPDLGZZPQK-UHFFFAOYSA-N 0.000 description 1
- KRYOUSVJJZAUFE-UHFFFAOYSA-N 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC=C(F)C(C(=O)N2CCC(CC2)C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 KRYOUSVJJZAUFE-UHFFFAOYSA-N 0.000 description 1
- WZZYNLFRMFXVPR-UHFFFAOYSA-N 5-[1-(2,5-difluorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC=C(F)C(C(=O)N2CC(CC2)C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 WZZYNLFRMFXVPR-UHFFFAOYSA-N 0.000 description 1
- QWQSKXMUSIFLKM-UHFFFAOYSA-N 5-[1-(2,5-dimethylfuran-3-carbonyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound O1C(C)=CC(C(=O)N2CC(CC2)C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1C QWQSKXMUSIFLKM-UHFFFAOYSA-N 0.000 description 1
- WUMHTGDDHNEMGN-UHFFFAOYSA-N 5-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound ClC1=CC=CC=C1C(=O)N1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 WUMHTGDDHNEMGN-UHFFFAOYSA-N 0.000 description 1
- MAOWSQBLIIDOGA-UHFFFAOYSA-N 5-[1-(2-cyano-2-methylpropyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=NN(CC(C)(C)C#N)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 MAOWSQBLIIDOGA-UHFFFAOYSA-N 0.000 description 1
- NVIKZNIMALAJOB-UHFFFAOYSA-N 5-[1-(2-cyanobenzoyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CC2=NC=NN2C=C1CNC(=O)C(S1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CC=C1C#N NVIKZNIMALAJOB-UHFFFAOYSA-N 0.000 description 1
- LEHNLCNLLKWWTH-UHFFFAOYSA-N 5-[1-(2-cyclopropylacetyl)-3,6-dihydro-2h-pyridin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide Chemical compound C1CC(C=2OC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=CCN1C(=O)CC1CC1 LEHNLCNLLKWWTH-UHFFFAOYSA-N 0.000 description 1
- KNHIATBPACPWNW-UHFFFAOYSA-N 5-[1-(2-cyclopropylacetyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)CC1CC1 KNHIATBPACPWNW-UHFFFAOYSA-N 0.000 description 1
- CUIOVEGLAJASKT-UHFFFAOYSA-N 5-[1-(2-fluorobenzoyl)-3,6-dihydro-2h-pyridin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide Chemical compound FC1=CC=CC=C1C(=O)N1CC=C(C=2OC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 CUIOVEGLAJASKT-UHFFFAOYSA-N 0.000 description 1
- CCBXBLSKKAYMKM-UHFFFAOYSA-N 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC=CC=C1C(=O)N1CCC(C=2SC(=CC=2)C(=O)NCC2=CN3N=CN=C3C=C2)CC1 CCBXBLSKKAYMKM-UHFFFAOYSA-N 0.000 description 1
- APJHBPHCAKWNBI-UHFFFAOYSA-N 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC=CC=C1C(=O)N1CCC(C=2SC(=CC=2)C(=O)NCC=2N=CC3=NC=CN3C=2)CC1 APJHBPHCAKWNBI-UHFFFAOYSA-N 0.000 description 1
- HEKVPRGBUOOJSJ-UHFFFAOYSA-N 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide Chemical compound FC1=CC=CC=C1C(=O)N1CCC(C=2OC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 HEKVPRGBUOOJSJ-UHFFFAOYSA-N 0.000 description 1
- KCZRQIKOGYCRDT-UHFFFAOYSA-N 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC=CC=C1C(=O)N1CCC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 KCZRQIKOGYCRDT-UHFFFAOYSA-N 0.000 description 1
- QOJSMCZKNRIXNG-UHFFFAOYSA-N 5-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC=CC=C1C(=O)N1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 QOJSMCZKNRIXNG-UHFFFAOYSA-N 0.000 description 1
- KIKCHNUBJRUYPM-UHFFFAOYSA-N 5-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1CN(C(=O)C(C)(O)C)CCC1C1=CC=C(C(=O)NCC2=CN3N=CN=C3C=C2)S1 KIKCHNUBJRUYPM-UHFFFAOYSA-N 0.000 description 1
- IYRDYDRYGJVGML-UHFFFAOYSA-N 5-[1-(2-hydroxy-2-methylpropyl)pyrazol-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1=NN(CC(C)(O)C)C=C1C1=CC=C(C(=O)NCC2=CN3N=CN=C3C=C2)S1 IYRDYDRYGJVGML-UHFFFAOYSA-N 0.000 description 1
- NYZYVIBQIFXBNW-UHFFFAOYSA-N 5-[1-(2-hydroxy-2-methylpropyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1=NN(CC(C)(O)C)C=C1C1=CC=C(C(=O)NCC2=CN3C=CN=C3C=C2)S1 NYZYVIBQIFXBNW-UHFFFAOYSA-N 0.000 description 1
- USJCECRGKZOTOQ-UHFFFAOYSA-N 5-[1-(2-hydroxy-2-methylpropyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide Chemical compound C1=NN(CC(C)(O)C)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)O1 USJCECRGKZOTOQ-UHFFFAOYSA-N 0.000 description 1
- RDIYUXWWZHPEOU-UHFFFAOYSA-N 5-[1-(2-hydroxy-2-methylpropyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=NN(CC(C)(O)C)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 RDIYUXWWZHPEOU-UHFFFAOYSA-N 0.000 description 1
- RJYZDUOADJKVIG-UHFFFAOYSA-N 5-[1-(2-hydroxyethyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=NN(CCO)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 RJYZDUOADJKVIG-UHFFFAOYSA-N 0.000 description 1
- UGIUVJZJHDETJA-UHFFFAOYSA-N 5-[1-(2-methylpropanoyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1CN(C(=O)C(C)C)CCC1C1=CC=C(C(=O)NCC2=CN3N=CN=C3C=C2)S1 UGIUVJZJHDETJA-UHFFFAOYSA-N 0.000 description 1
- UQSABWPHTGFEHM-UHFFFAOYSA-N 5-[1-(2-methylpropyl)pyrazol-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide Chemical compound C1=NN(CC(C)C)C=C1C1=CC=C(C(=O)NCC2=CN3N=CN=C3C=C2)O1 UQSABWPHTGFEHM-UHFFFAOYSA-N 0.000 description 1
- GOWWYAJAYPKKOJ-UHFFFAOYSA-N 5-[1-(2-methylpropyl)pyrazol-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=NN(CC(C)C)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=NN3C=C2)S1 GOWWYAJAYPKKOJ-UHFFFAOYSA-N 0.000 description 1
- LBRUIBGFFNAZIV-UHFFFAOYSA-N 5-[1-(3,3-dimethylbutanoyl)-3,6-dihydro-2h-pyridin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide Chemical compound C1N(C(=O)CC(C)(C)C)CCC(C=2OC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 LBRUIBGFFNAZIV-UHFFFAOYSA-N 0.000 description 1
- LBOMYEKWSHLHPA-UHFFFAOYSA-N 5-[1-(3,3-dimethylbutanoyl)-4-hydroxypiperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1CN(C(=O)CC(C)(C)C)CCC1(O)C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 LBOMYEKWSHLHPA-UHFFFAOYSA-N 0.000 description 1
- XRGUUFXRJXZLTO-UHFFFAOYSA-N 5-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1N(C(=O)CC(C)(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 XRGUUFXRJXZLTO-UHFFFAOYSA-N 0.000 description 1
- HCYWQQJHRSHOFY-UHFFFAOYSA-N 5-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC(F)=CC(C(=O)N2CCC(CC2)C=2SC(=CC=2)C(=O)NCC2=CN3N=CN=C3C=C2)=C1 HCYWQQJHRSHOFY-UHFFFAOYSA-N 0.000 description 1
- MECOFIUTOXFXTL-UHFFFAOYSA-N 5-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC(F)=CC(C(=O)N2CC(CC2)C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 MECOFIUTOXFXTL-UHFFFAOYSA-N 0.000 description 1
- SNFKXFJXLSDEFY-UHFFFAOYSA-N 5-[1-(3,5-dimethyl-1,2-oxazole-4-carbonyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound CC1=NOC(C)=C1C(=O)N1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 SNFKXFJXLSDEFY-UHFFFAOYSA-N 0.000 description 1
- RGCSWPWHDJJUJY-UHFFFAOYSA-N 5-[1-(3-amino-2,2-dimethylpropyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=NN(CC(C)(CN)C)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 RGCSWPWHDJJUJY-UHFFFAOYSA-N 0.000 description 1
- KRKSNYSWRPSHJZ-UHFFFAOYSA-N 5-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound ClC1=CC=CC(C(=O)N2CC(CC2)C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 KRKSNYSWRPSHJZ-UHFFFAOYSA-N 0.000 description 1
- NJFADWRSRICEJT-UHFFFAOYSA-N 5-[1-(3-fluorobenzoyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC=CC(C(=O)N2CCC(CC2)C=2SC(=CC=2)C(=O)NCC2=CN3N=CN=C3C=C2)=C1 NJFADWRSRICEJT-UHFFFAOYSA-N 0.000 description 1
- YCLPUGAPZFEMRI-UHFFFAOYSA-N 5-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC=CC(C(=O)N2CC(CC2)C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 YCLPUGAPZFEMRI-UHFFFAOYSA-N 0.000 description 1
- PVDDJGXTYMGKRH-UHFFFAOYSA-N 5-[1-(3-methylbutanoyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1CN(C(=O)CC(C)C)CCC1C1=CC=C(C(=O)NCC2=CN3N=CN=C3C=C2)S1 PVDDJGXTYMGKRH-UHFFFAOYSA-N 0.000 description 1
- JSEVDUHUQZMRLL-UHFFFAOYSA-N 5-[1-(4,4-difluorocyclohexanecarbonyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1CC(F)(F)CCC1C(=O)N1CCC(C=2SC(=CC=2)C(=O)NCC2=CN3N=CN=C3C=C2)CC1 JSEVDUHUQZMRLL-UHFFFAOYSA-N 0.000 description 1
- YMVJVXQNDMJMCQ-UHFFFAOYSA-N 5-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 YMVJVXQNDMJMCQ-UHFFFAOYSA-N 0.000 description 1
- KAVHMFAFLYRFMX-UHFFFAOYSA-N 5-[1-(4-cyanobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(C1)CCN1C(=O)C1=CC=C(C#N)C=C1 KAVHMFAFLYRFMX-UHFFFAOYSA-N 0.000 description 1
- VHMLZACDNQFBDL-UHFFFAOYSA-N 5-[1-(4-fluorobenzoyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CC(F)=CC=C1C(=O)N1CCC(C=2SC(=CC=2)C(=O)NCC2=CN3N=CN=C3C=C2)CC1 VHMLZACDNQFBDL-UHFFFAOYSA-N 0.000 description 1
- XBGPIPXGULTLIG-UHFFFAOYSA-N 5-[1-(4-fluorobenzoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CC(F)=CC=C1C(=O)N1CCC(C=2SC(=CC=2)C(=O)NCC=2N=CC3=NC=CN3C=2)CC1 XBGPIPXGULTLIG-UHFFFAOYSA-N 0.000 description 1
- RSJBSIQTRIHKSJ-UHFFFAOYSA-N 5-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 RSJBSIQTRIHKSJ-UHFFFAOYSA-N 0.000 description 1
- WRQKJQODBBQFHF-UHFFFAOYSA-N 5-[1-(benzenesulfonyl)-3,6-dihydro-2h-pyridin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(O1)=CC=C1C(CC1)=CCN1S(=O)(=O)C1=CC=CC=C1 WRQKJQODBBQFHF-UHFFFAOYSA-N 0.000 description 1
- OANDQWYUAHLBBW-UHFFFAOYSA-N 5-[1-(benzenesulfonyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CC2=NC=NN2C=C1CNC(=O)C(S1)=CC=C1C(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 OANDQWYUAHLBBW-UHFFFAOYSA-N 0.000 description 1
- RBTKMLOEXOVGKI-UHFFFAOYSA-N 5-[1-(cyclobutylmethyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1CCC1 RBTKMLOEXOVGKI-UHFFFAOYSA-N 0.000 description 1
- OFTGRMDDEUMQOQ-UHFFFAOYSA-N 5-[1-(cyclobutylmethyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(O1)=CC=C1C(=C1)C=NN1CC1CCC1 OFTGRMDDEUMQOQ-UHFFFAOYSA-N 0.000 description 1
- OQSHCMFAPNWBFZ-UHFFFAOYSA-N 5-[1-(cyclobutylmethyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1CCC1 OQSHCMFAPNWBFZ-UHFFFAOYSA-N 0.000 description 1
- DWLGHVRTZWARTH-UHFFFAOYSA-N 5-[1-(cyclohexylmethyl)-5-ethylpyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound CCC1=C(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C=NN1CC1CCCCC1 DWLGHVRTZWARTH-UHFFFAOYSA-N 0.000 description 1
- AASUTBCBDWRDCO-UHFFFAOYSA-N 5-[1-(cyclohexylmethyl)pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1CCCCC1 AASUTBCBDWRDCO-UHFFFAOYSA-N 0.000 description 1
- UWFCEILIGUXNTP-UHFFFAOYSA-N 5-[1-(cyclopentanecarbonyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(C1)CCN1C(=O)C1CCCC1 UWFCEILIGUXNTP-UHFFFAOYSA-N 0.000 description 1
- SOIPQSOKDNRGGT-UHFFFAOYSA-N 5-[1-(cyclopropanecarbonyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(CC1)CCN1C(=O)C1CC1 SOIPQSOKDNRGGT-UHFFFAOYSA-N 0.000 description 1
- KECKCMFSHZGVSK-UHFFFAOYSA-N 5-[1-(cyclopropanecarbonyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(C1)CCN1C(=O)C1CC1 KECKCMFSHZGVSK-UHFFFAOYSA-N 0.000 description 1
- RLJLEJBCCHJUQU-UHFFFAOYSA-N 5-[1-(furan-2-carbonyl)pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(C1)CCN1C(=O)C1=CC=CO1 RLJLEJBCCHJUQU-UHFFFAOYSA-N 0.000 description 1
- XDOJGEMMFDRUIM-UHFFFAOYSA-N 5-[1-(oxane-4-carbonyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CC2=NC=NN2C=C1CNC(=O)C(S1)=CC=C1C(CC1)CCN1C(=O)C1CCOCC1 XDOJGEMMFDRUIM-UHFFFAOYSA-N 0.000 description 1
- PBFXSPAHOOSXOT-UHFFFAOYSA-N 5-[1-(pyridine-2-carbonyl)piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CC2=NC=NN2C=C1CNC(=O)C(S1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CC=N1 PBFXSPAHOOSXOT-UHFFFAOYSA-N 0.000 description 1
- CIHXKSQXTLZUCL-UHFFFAOYSA-N 5-[1-[(1,1-dioxothian-3-yl)methyl]pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1CCCS(=O)(=O)C1 CIHXKSQXTLZUCL-UHFFFAOYSA-N 0.000 description 1
- MKZDBMUFRMZJCH-MRXNPFEDSA-N 5-[1-[(2r)-2-hydroxybutyl]pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1=NN(C[C@H](O)CC)C=C1C1=CC=C(C(=O)NCC2=CN3C=CN=C3C=C2)S1 MKZDBMUFRMZJCH-MRXNPFEDSA-N 0.000 description 1
- YRDVBEOCWPLNKX-CYBMUJFWSA-N 5-[1-[(2r)-2-hydroxypropyl]pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=NN(C[C@H](O)C)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 YRDVBEOCWPLNKX-CYBMUJFWSA-N 0.000 description 1
- SQQMFNVMGCPZMC-HNNXBMFYSA-N 5-[1-[(2s)-2-methylbutanoyl]piperidin-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1CN(C(=O)[C@@H](C)CC)CCC1C1=CC=C(C(=O)NCC2=CN3N=CN=C3C=C2)S1 SQQMFNVMGCPZMC-HNNXBMFYSA-N 0.000 description 1
- OJOBCXVUIGSDJV-UHFFFAOYSA-N 5-[1-[(4-fluorooxan-4-yl)methyl]pyrazol-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide Chemical compound C1=C(C=2OC(=CC=2)C(=O)NCC2=CN3N=CN=C3C=C2)C=NN1CC1(F)CCOCC1 OJOBCXVUIGSDJV-UHFFFAOYSA-N 0.000 description 1
- LRSLNETVCFMAMV-UHFFFAOYSA-N 5-[1-[(4-fluorooxan-4-yl)methyl]pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide Chemical compound C1=C(C=2OC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C=NN1CC1(F)CCOCC1 LRSLNETVCFMAMV-UHFFFAOYSA-N 0.000 description 1
- WEIIQMSRICRSJS-UHFFFAOYSA-N 5-[1-[(4-fluorooxan-4-yl)methyl]pyrazol-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=C(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C=NN1CC1(F)CCOCC1 WEIIQMSRICRSJS-UHFFFAOYSA-N 0.000 description 1
- ZSGLWDXNHRAQMD-UHFFFAOYSA-N 5-[1-[(4-methyloxan-4-yl)methyl]pyrazol-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide Chemical compound C1=C(C=2OC(=CC=2)C(=O)NCC2=CN3N=CN=C3C=C2)C=NN1CC1(C)CCOCC1 ZSGLWDXNHRAQMD-UHFFFAOYSA-N 0.000 description 1
- JLMCZSKVHLVBJW-UHFFFAOYSA-N 5-[1-[(4-methyloxan-4-yl)methyl]pyrazol-4-yl]-n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide Chemical compound C1=C(C=2SC(=CC=2)C(=O)NCC2=CN3N=CN=C3C=C2)C=NN1CC1(C)CCOCC1 JLMCZSKVHLVBJW-UHFFFAOYSA-N 0.000 description 1
- MMHPGEHNNWAUJG-UHFFFAOYSA-N 5-[1-[2-(2-fluorophenyl)acetyl]pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC=CC=C1CC(=O)N1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 MMHPGEHNNWAUJG-UHFFFAOYSA-N 0.000 description 1
- IQGLALPWLVSIFI-UHFFFAOYSA-N 5-[1-[2-(3,5-difluorophenyl)acetyl]pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC(F)=CC(CC(=O)N2CC(CC2)C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 IQGLALPWLVSIFI-UHFFFAOYSA-N 0.000 description 1
- IGHWCIVSCUADJM-UHFFFAOYSA-N 5-[1-[2-(3-fluorophenyl)acetyl]pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound FC1=CC=CC(CC(=O)N2CC(CC2)C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 IGHWCIVSCUADJM-UHFFFAOYSA-N 0.000 description 1
- ZBOZQQJOGQXEMZ-UHFFFAOYSA-N 5-[1-[2-(4-fluorophenyl)acetyl]pyrrolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=CC(F)=CC=C1CC(=O)N1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 ZBOZQQJOGQXEMZ-UHFFFAOYSA-N 0.000 description 1
- RJPYYVANNAHZHH-UHFFFAOYSA-N 5-[2-benzyl-5-(2-methylpropyl)pyrazol-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound N1=C(CC(C)C)C=C(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)N1CC1=CC=CC=C1 RJPYYVANNAHZHH-UHFFFAOYSA-N 0.000 description 1
- ZTAQFRPQBIZSOI-UHFFFAOYSA-N 5-[3-hydroxy-1-(2-methylpropanoyl)azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1N(C(=O)C(C)C)CC1(O)C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 ZTAQFRPQBIZSOI-UHFFFAOYSA-N 0.000 description 1
- XRVGPPQTIOIATE-AWEZNQCLSA-N 5-[3-hydroxy-1-[(2s)-2-methylbutanoyl]azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1N(C(=O)[C@@H](C)CC)CC1(O)C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 XRVGPPQTIOIATE-AWEZNQCLSA-N 0.000 description 1
- CUIYBZFIFPYMRA-UHFFFAOYSA-N 5-[3-hydroxy-1-[2-(oxan-4-yl)acetyl]azetidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1C(O)(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)CC1CCOCC1 CUIYBZFIFPYMRA-UHFFFAOYSA-N 0.000 description 1
- HVFDMWHCFFEUCJ-UHFFFAOYSA-N 5-[4-hydroxy-1-(2-methylpropanoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1CN(C(=O)C(C)C)CCC1(O)C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 HVFDMWHCFFEUCJ-UHFFFAOYSA-N 0.000 description 1
- TWKYRVKFRZJYBW-UHFFFAOYSA-N 5-[4-hydroxy-1-(3-methylbutanoyl)piperidin-4-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1CN(C(=O)CC(C)C)CCC1(O)C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 TWKYRVKFRZJYBW-UHFFFAOYSA-N 0.000 description 1
- QBHGDTAXWLXHJZ-UHFFFAOYSA-N 5-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound O=C1OC(CO)CN1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 QBHGDTAXWLXHJZ-UHFFFAOYSA-N 0.000 description 1
- CURWQECUSPYJKF-UHFFFAOYSA-N 5-[5-cyclopropyl-2-(2-methoxyethyl)pyrazol-3-yl]-n-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide Chemical compound C1=C(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)N(CCOC)N=C1C1CC1 CURWQECUSPYJKF-UHFFFAOYSA-N 0.000 description 1
- ZWONMHVYQRHJGX-UHFFFAOYSA-N 7-methyl-4,7-diazabicyclo[3.2.0]heptane Chemical group N1CCC2N(C)CC21 ZWONMHVYQRHJGX-UHFFFAOYSA-N 0.000 description 1
- 208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000006416 CBr Chemical group BrC* 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- 125000006415 CF Chemical group FC* 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 230000033616 DNA repair Effects 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 108091006027 G proteins Proteins 0.000 description 1
- 102000030782 GTP binding Human genes 0.000 description 1
- 108091000058 GTP-Binding Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 102000000424 Matrix Metalloproteinase 2 Human genes 0.000 description 1
- 108010016165 Matrix Metalloproteinase 2 Proteins 0.000 description 1
- 102000001776 Matrix metalloproteinase-9 Human genes 0.000 description 1
- 108010015302 Matrix metalloproteinase-9 Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 108010057466 NF-kappa B Proteins 0.000 description 1
- 102000003945 NF-kappa B Human genes 0.000 description 1
- ZAHXYMFVNNUHCP-UHFFFAOYSA-N Naphazoline nitrate Chemical group O[N+]([O-])=O.C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 ZAHXYMFVNNUHCP-UHFFFAOYSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 102000011990 Sirtuin Human genes 0.000 description 1
- 108050002485 Sirtuin Proteins 0.000 description 1
- QAOWNCQODCNURD-ZSJDYOACSA-N Sulfuric acid-d2 Chemical compound [2H]OS(=O)(=O)O[2H] QAOWNCQODCNURD-ZSJDYOACSA-N 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical group 0.000 description 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 description 1
- 125000004686 alkyl sulfanyl alkyl group Chemical group 0.000 description 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000002785 azepinyl group Chemical group 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004602 benzodiazinyl group Chemical group N1=NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000005750 disease progression Effects 0.000 description 1
- 238000004980 dosimetry Methods 0.000 description 1
- 201000002491 encephalomyelitis Diseases 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 208000012997 experimental autoimmune encephalomyelitis Diseases 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 1
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 description 1
- 125000005438 isoindazolyl group Chemical group 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000005969 isothiazolinyl group Chemical group 0.000 description 1
- 238000001948 isotopic labelling Methods 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 229940043355 kinase inhibitor Drugs 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- QVFDMLMUOWETNX-UHFFFAOYSA-N n-(1-hydroxy-2-methylpropan-2-yl)-4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)benzamide Chemical compound C1=CC(C(=O)NC(C)(CO)C)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 QVFDMLMUOWETNX-UHFFFAOYSA-N 0.000 description 1
- SQGJQDLIGNKXNE-UHFFFAOYSA-N n-(2-hydroxy-2-methylpropyl)-4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)benzamide Chemical compound C1=CC(C(=O)NCC(C)(O)C)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 SQGJQDLIGNKXNE-UHFFFAOYSA-N 0.000 description 1
- AMQAXQMRUYRGKE-UHFFFAOYSA-N n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1CN(C(=O)CC(F)(F)F)CCC1C1=CC=C(C(=O)NCC2=CN3N=CN=C3C=C2)S1 AMQAXQMRUYRGKE-UHFFFAOYSA-N 0.000 description 1
- QTFSVNDJQVYASV-UHFFFAOYSA-N n-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1CN(C(=O)CCC(F)(F)F)CCC1C1=CC=C(C(=O)NCC2=CN3N=CN=C3C=C2)S1 QTFSVNDJQVYASV-UHFFFAOYSA-N 0.000 description 1
- QBFQLMXVNLYHGE-UHFFFAOYSA-N n-(cyclopentylmethyl)-4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)benzamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(=O)NCC1CCCC1 QBFQLMXVNLYHGE-UHFFFAOYSA-N 0.000 description 1
- PQNUGKZSNWGKCD-UHFFFAOYSA-N n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(1-propan-2-ylsulfonylpiperidin-4-yl)benzamide Chemical compound C1CN(S(=O)(=O)C(C)C)CCC1C1=CC=C(C(=O)NCC=2N=CC3=NC=CN3C=2)C=C1 PQNUGKZSNWGKCD-UHFFFAOYSA-N 0.000 description 1
- FYRVARDSVMHONG-UHFFFAOYSA-N n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC=2N=CC3=NC=CN3C=2)CCN1C(=O)C1(C)CC1 FYRVARDSVMHONG-UHFFFAOYSA-N 0.000 description 1
- NOXXTCGFPPMFGW-UHFFFAOYSA-N n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide Chemical compound C1CN(C(=O)C(C)C)CCC1C1=CC=C(C(=O)NCC=2N=CC3=NC=CN3C=2)C=C1 NOXXTCGFPPMFGW-UHFFFAOYSA-N 0.000 description 1
- KMIOEWSIRNFUDX-UHFFFAOYSA-N n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide Chemical compound C1CN(C(=O)CC(F)(F)F)CCC1C1=CC=C(C(=O)NCC=2N=CC3=NC=CN3C=2)C=C1 KMIOEWSIRNFUDX-UHFFFAOYSA-N 0.000 description 1
- CWONJUGIMJGECZ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(3-methylbutanoyl)piperidin-4-yl]benzamide Chemical compound C1CN(C(=O)CC(C)C)CCC1C1=CC=C(C(=O)NCC=2N=CC3=NC=CN3C=2)C=C1 CWONJUGIMJGECZ-UHFFFAOYSA-N 0.000 description 1
- AVTHIBDEKILSJU-UHFFFAOYSA-N n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1CC(C=2SC(=CC=2)C(=O)NCC=2N=CC3=NC=CN3C=2)CCN1C(=O)C1(C)CC1 AVTHIBDEKILSJU-UHFFFAOYSA-N 0.000 description 1
- OIYIOASYWIFTIT-UHFFFAOYSA-N n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1CN(C(=O)C(C)C)CCC1C1=CC=C(C(=O)NCC=2N=CC3=NC=CN3C=2)S1 OIYIOASYWIFTIT-UHFFFAOYSA-N 0.000 description 1
- AKOCFRDGJLXLSY-UHFFFAOYSA-N n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropyl)pyrazol-4-yl]furan-2-carboxamide Chemical compound C1=NN(CC(C)C)C=C1C1=CC=C(C(=O)NCC=2N=CC3=NC=CN3C=2)O1 AKOCFRDGJLXLSY-UHFFFAOYSA-N 0.000 description 1
- VEXUYHXKGAHJMB-UHFFFAOYSA-N n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=NN(CC(C)C)C=C1C1=CC=C(C(=O)NCC=2N=CC3=NC=CN3C=2)S1 VEXUYHXKGAHJMB-UHFFFAOYSA-N 0.000 description 1
- VQZUXCDDCUOXIB-UHFFFAOYSA-N n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-piperazin-1-ylethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C=1N2C=CN=C2C=NC=1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CCN1CCNCC1 VQZUXCDDCUOXIB-UHFFFAOYSA-N 0.000 description 1
- RVMYUEORZSFGJA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(3-methylbutanoyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1CN(C(=O)CC(C)C)CCC1C1=CC=C(C(=O)NCC=2N=CC3=NC=CN3C=2)S1 RVMYUEORZSFGJA-UHFFFAOYSA-N 0.000 description 1
- QROHSQHETDSEEI-UHFFFAOYSA-N n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1CN(C(=O)CCC(F)(F)F)CCC1C1=CC=C(C(=O)NCC=2N=CC3=NC=CN3C=2)S1 QROHSQHETDSEEI-UHFFFAOYSA-N 0.000 description 1
- XEOSEIHOXNUTNT-UHFFFAOYSA-N n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(oxane-4-carbonyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C=1N2C=CN=C2C=NC=1CNC(=O)C(S1)=CC=C1C(CC1)CCN1C(=O)C1CCOCC1 XEOSEIHOXNUTNT-UHFFFAOYSA-N 0.000 description 1
- NFJOSZWWOOLNFX-UHFFFAOYSA-N n-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-[(4-methyloxan-4-yl)methyl]pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=C(C=2SC(=CC=2)C(=O)NCC=2N=CC3=NC=CN3C=2)C=NN1CC1(C)CCOCC1 NFJOSZWWOOLNFX-UHFFFAOYSA-N 0.000 description 1
- HEGBEBKFULLTLS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)-1,3-thiazole-5-carboxamide Chemical compound C1CC2=CC=CC=C2CCN1C(S1)=NC=C1C(=O)NCC1=CN2C=CN=C2C=C1 HEGBEBKFULLTLS-UHFFFAOYSA-N 0.000 description 1
- DCPFHDXGJCWQJJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(2-oxo-5-phenyl-1,3-oxazolidin-3-yl)-1,3-thiazole-5-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CN=C1N(C(O1)=O)CC1C1=CC=CC=C1 DCPFHDXGJCWQJJ-UHFFFAOYSA-N 0.000 description 1
- GKVCZTOQWKMVNL-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(3-methylbutanoylamino)-1,3-thiazole-5-carboxamide Chemical compound S1C(NC(=O)CC(C)C)=NC=C1C(=O)NCC1=CN2C=CN=C2C=C1 GKVCZTOQWKMVNL-UHFFFAOYSA-N 0.000 description 1
- KNGPHMOOHYYSPM-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(3-methylbutylamino)-1,3-thiazole-5-carboxamide Chemical compound S1C(NCCC(C)C)=NC=C1C(=O)NCC1=CN2C=CN=C2C=C1 KNGPHMOOHYYSPM-UHFFFAOYSA-N 0.000 description 1
- VNSSFSGJXAKXEG-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(3-phenylpyrrolidin-1-yl)-1,3-thiazole-5-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CN=C1N(C1)CCC1C1=CC=CC=C1 VNSSFSGJXAKXEG-UHFFFAOYSA-N 0.000 description 1
- VUGHUZSMFMXSNQ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[2-methoxyethylcarbamoyl(oxan-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)SC=1N(C(=O)NCCOC)CC1CCOCC1 VUGHUZSMFMXSNQ-UHFFFAOYSA-N 0.000 description 1
- GLJGQUQUPMEDJG-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[2-methoxyethylcarbamoyl(oxolan-3-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)SC=1N(C(=O)NCCOC)CC1CCOC1 GLJGQUQUPMEDJG-UHFFFAOYSA-N 0.000 description 1
- LCJIQBUOAKYDKB-MRXNPFEDSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[2-methoxyethylcarbamoyl-[[(2r)-oxolan-2-yl]methyl]amino]-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)SC=1N(C(=O)NCCOC)C[C@H]1CCCO1 LCJIQBUOAKYDKB-MRXNPFEDSA-N 0.000 description 1
- LCJIQBUOAKYDKB-INIZCTEOSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[2-methoxyethylcarbamoyl-[[(2s)-oxolan-2-yl]methyl]amino]-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)SC=1N(C(=O)NCCOC)C[C@@H]1CCCO1 LCJIQBUOAKYDKB-INIZCTEOSA-N 0.000 description 1
- HDKFNJYGRBDGHI-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[2-oxo-4-(oxolan-3-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CN=C1N(C(OC1)=O)C1C1CCOC1 HDKFNJYGRBDGHI-UHFFFAOYSA-N 0.000 description 1
- LFUUUFUNUURQIC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[3-(1,2-oxazol-4-yl)propanoyl-(oxolan-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound C1CCOC1CN(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)C(=O)CCC=1C=NOC=1 LFUUUFUNUURQIC-UHFFFAOYSA-N 0.000 description 1
- STPMOSYNVAHJRN-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[3-(1,2-oxazol-5-yl)propanoyl-(oxolan-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound C1CCOC1CN(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)C(=O)CCC1=CC=NO1 STPMOSYNVAHJRN-UHFFFAOYSA-N 0.000 description 1
- LBPWSXISGWWBMC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[3-(1-methylpyrazol-4-yl)propanoyl-(oxolan-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound C1=NN(C)C=C1CCC(=O)N(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)CC1OCCC1 LBPWSXISGWWBMC-UHFFFAOYSA-N 0.000 description 1
- YQBMUFVYNOYJFB-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[3-(1-methylpyrrol-2-yl)propanoyl-(oxolan-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound CN1C=CC=C1CCC(=O)N(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)CC1OCCC1 YQBMUFVYNOYJFB-UHFFFAOYSA-N 0.000 description 1
- ZDUQRVMORVDHHV-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[3-(3-methoxy-1,2-oxazol-5-yl)propanoyl-(oxolan-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound O1N=C(OC)C=C1CCC(=O)N(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)CC1OCCC1 ZDUQRVMORVDHHV-UHFFFAOYSA-N 0.000 description 1
- RBDNPFQPRGLTAZ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[3-(4-methyl-1,3-thiazol-5-yl)propanoyl-(oxolan-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound N1=CSC(CCC(=O)N(CC2OCCC2)C=2SC(=CN=2)C(=O)NCC2=CN3C=CN=C3C=C2)=C1C RBDNPFQPRGLTAZ-UHFFFAOYSA-N 0.000 description 1
- FXXDCCXBYBAUNF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[3-methoxypropanoyl(3-methylbutyl)amino]-1,3-thiazole-5-carboxamide Chemical compound S1C(N(CCC(C)C)C(=O)CCOC)=NC=C1C(=O)NCC1=CN2C=CN=C2C=C1 FXXDCCXBYBAUNF-UHFFFAOYSA-N 0.000 description 1
- QXACXODVKZTOSE-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[3-methoxypropanoyl(oxan-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)SC=1N(C(=O)CCOC)CC1CCOCC1 QXACXODVKZTOSE-UHFFFAOYSA-N 0.000 description 1
- ZIVPGUIMWNDYNQ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[3-methoxypropanoyl(oxolan-3-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)SC=1N(C(=O)CCOC)CC1CCOC1 ZIVPGUIMWNDYNQ-UHFFFAOYSA-N 0.000 description 1
- CJOZVENPFMWMDF-MRXNPFEDSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[3-methoxypropanoyl-[[(2r)-oxolan-2-yl]methyl]amino]-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)SC=1N(C(=O)CCOC)C[C@H]1CCCO1 CJOZVENPFMWMDF-MRXNPFEDSA-N 0.000 description 1
- CJOZVENPFMWMDF-INIZCTEOSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[3-methoxypropanoyl-[[(2s)-oxolan-2-yl]methyl]amino]-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)SC=1N(C(=O)CCOC)C[C@@H]1CCCO1 CJOZVENPFMWMDF-INIZCTEOSA-N 0.000 description 1
- ODCOXSHQJPDPJG-GOSISDBHSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[[(2r)-oxolan-2-yl]methyl-(2-propan-2-yloxyethylcarbamoyl)amino]-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)SC=1N(C(=O)NCCOC(C)C)C[C@H]1CCCO1 ODCOXSHQJPDPJG-GOSISDBHSA-N 0.000 description 1
- ODCOXSHQJPDPJG-SFHVURJKSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[[(2s)-oxolan-2-yl]methyl-(2-propan-2-yloxyethylcarbamoyl)amino]-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)SC=1N(C(=O)NCCOC(C)C)C[C@@H]1CCCO1 ODCOXSHQJPDPJG-SFHVURJKSA-N 0.000 description 1
- CTFFQAYASADOCX-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[[2-(1,2-oxazol-3-yl)acetyl]-(oxolan-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound C1CCOC1CN(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)C(=O)CC=1C=CON=1 CTFFQAYASADOCX-UHFFFAOYSA-N 0.000 description 1
- CSEBDGOKCGUBLE-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[[2-(1-methylpyrazol-4-yl)acetyl]-(oxolan-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound C1=NN(C)C=C1CC(=O)N(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)CC1OCCC1 CSEBDGOKCGUBLE-UHFFFAOYSA-N 0.000 description 1
- MQOPUNGSVXBVCL-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[[2-(2-methyl-1,3-thiazol-4-yl)acetyl]-(oxolan-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(CC(=O)N(CC2OCCC2)C=2SC(=CN=2)C(=O)NCC2=CN3C=CN=C3C=C2)=C1 MQOPUNGSVXBVCL-UHFFFAOYSA-N 0.000 description 1
- XDDDDYBNVAEULV-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[[2-(2-methyl-1,3-thiazol-5-yl)acetyl]-(oxolan-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC=C1CC(=O)N(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)CC1OCCC1 XDDDDYBNVAEULV-UHFFFAOYSA-N 0.000 description 1
- CRRVFHXZYHZITO-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[[2-(3-methyl-1,2-oxazol-5-yl)acetyl]-(oxolan-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound O1N=C(C)C=C1CC(=O)N(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)CC1OCCC1 CRRVFHXZYHZITO-UHFFFAOYSA-N 0.000 description 1
- XYOWEVKQPJOCPQ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[oxan-4-ylmethyl(2-propan-2-yloxyethylcarbamoyl)amino]-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)SC=1N(C(=O)NCCOC(C)C)CC1CCOCC1 XYOWEVKQPJOCPQ-UHFFFAOYSA-N 0.000 description 1
- KCANBJPGSSHAIC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[oxan-4-ylmethyl(oxolane-3-carbonyl)amino]-1,3-thiazole-5-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CN=C1N(C(=O)C1COCC1)CC1CCOCC1 KCANBJPGSSHAIC-UHFFFAOYSA-N 0.000 description 1
- ZEBOUZBPINKTKC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[oxane-4-carbonyl(oxan-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CN=C1N(C(=O)C1CCOCC1)CC1CCOCC1 ZEBOUZBPINKTKC-UHFFFAOYSA-N 0.000 description 1
- XTIPQWBUYFCKCB-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[oxane-4-carbonyl(oxolan-3-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CN=C1N(C(=O)C1CCOCC1)CC1CCOC1 XTIPQWBUYFCKCB-UHFFFAOYSA-N 0.000 description 1
- BPTADIJFSKTIAJ-GOSISDBHSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[oxane-4-carbonyl-[[(2r)-oxolan-2-yl]methyl]amino]-1,3-thiazole-5-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CN=C1N(C(=O)C1CCOCC1)C[C@H]1CCCO1 BPTADIJFSKTIAJ-GOSISDBHSA-N 0.000 description 1
- BPTADIJFSKTIAJ-SFHVURJKSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[oxane-4-carbonyl-[[(2s)-oxolan-2-yl]methyl]amino]-1,3-thiazole-5-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CN=C1N(C(=O)C1CCOCC1)C[C@@H]1CCCO1 BPTADIJFSKTIAJ-SFHVURJKSA-N 0.000 description 1
- ODCOXSHQJPDPJG-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[oxolan-2-ylmethyl(2-propan-2-yloxyethylcarbamoyl)amino]-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)SC=1N(C(=O)NCCOC(C)C)CC1CCCO1 ODCOXSHQJPDPJG-UHFFFAOYSA-N 0.000 description 1
- OQTDVBHQOFSADZ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[oxolan-2-ylmethyl-[2-(1,3-thiazol-4-yl)acetyl]amino]-1,3-thiazole-5-carboxamide Chemical compound C1CCOC1CN(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)C(=O)CC1=CSC=N1 OQTDVBHQOFSADZ-UHFFFAOYSA-N 0.000 description 1
- OGVWBRHHTXFTAG-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[oxolan-2-ylmethyl-[2-(2h-tetrazol-5-yl)acetyl]amino]-1,3-thiazole-5-carboxamide Chemical compound C1CCOC1CN(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)C(=O)CC1=NN=NN1 OGVWBRHHTXFTAG-UHFFFAOYSA-N 0.000 description 1
- XOCPUSAVIWGSKT-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[oxolan-2-ylmethyl-[3-(1,3-thiazol-2-yl)propanoyl]amino]-1,3-thiazole-5-carboxamide Chemical compound C1CCOC1CN(C=1SC(=CN=1)C(=O)NCC1=CN2C=CN=C2C=C1)C(=O)CCC1=NC=CS1 XOCPUSAVIWGSKT-UHFFFAOYSA-N 0.000 description 1
- XFOZZAVEHBHWLA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[oxolan-3-ylmethyl(2-propan-2-yloxyethylcarbamoyl)amino]-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)SC=1N(C(=O)NCCOC(C)C)CC1CCOC1 XFOZZAVEHBHWLA-UHFFFAOYSA-N 0.000 description 1
- RAHOAHIHFOUJLN-ZYMOGRSISA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[oxolane-3-carbonyl-[[(2r)-oxolan-2-yl]methyl]amino]-1,3-thiazole-5-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CN=C1N(C(=O)C1COCC1)C[C@H]1CCCO1 RAHOAHIHFOUJLN-ZYMOGRSISA-N 0.000 description 1
- RAHOAHIHFOUJLN-DJNXLDHESA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[oxolane-3-carbonyl-[[(2s)-oxolan-2-yl]methyl]amino]-1,3-thiazole-5-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CN=C1N(C(=O)C1COCC1)C[C@@H]1CCCO1 RAHOAHIHFOUJLN-DJNXLDHESA-N 0.000 description 1
- CMQAQTIXOYECNA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(2-morpholin-4-ylacetyl)amino]benzamide Chemical compound C=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CN1CCOCC1 CMQAQTIXOYECNA-UHFFFAOYSA-N 0.000 description 1
- IRTRMXCBSQWESD-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(2-propan-2-yloxyacetyl)amino]benzamide Chemical compound C1=CC(NC(=O)COC(C)C)=CC=C1C(=O)NCC1=CN2C=CN=C2C=C1 IRTRMXCBSQWESD-UHFFFAOYSA-N 0.000 description 1
- NJSZRYSJBANYBX-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropanoyl)-3,6-dihydro-2h-pyridin-4-yl]benzamide Chemical compound C1N(C(=O)C(C)C)CCC(C=2C=CC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)=C1 NJSZRYSJBANYBX-UHFFFAOYSA-N 0.000 description 1
- YDVBYKFJVUMQCN-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]oxybenzamide Chemical compound C1CN(C(=O)C(C)C)CCC1OC1=CC=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=C1 YDVBYKFJVUMQCN-UHFFFAOYSA-N 0.000 description 1
- LARFFVYGPRPKAJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropyl)pyrazol-4-yl]benzamide Chemical compound C1=NN(CC(C)C)C=C1C1=CC=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=C1 LARFFVYGPRPKAJ-UHFFFAOYSA-N 0.000 description 1
- RGEKYSRCJWIICG-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-morpholin-4-ylacetyl)-3,6-dihydro-2h-pyridin-4-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)=CCN1C(=O)CN1CCOCC1 RGEKYSRCJWIICG-UHFFFAOYSA-N 0.000 description 1
- SAHBTXMVUZCLIC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-propan-2-yloxyacetyl)-3,6-dihydro-2h-pyridin-4-yl]benzamide Chemical compound C1N(C(=O)COC(C)C)CCC(C=2C=CC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)=C1 SAHBTXMVUZCLIC-UHFFFAOYSA-N 0.000 description 1
- ZVJFNRCULLIPHI-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-propan-2-yloxyacetyl)piperidin-4-yl]oxybenzamide Chemical compound C1CN(C(=O)COC(C)C)CCC1OC1=CC=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=C1 ZVJFNRCULLIPHI-UHFFFAOYSA-N 0.000 description 1
- OQOPMDUTIYDECV-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]oxybenzamide Chemical compound C1CN(C(=O)CC(F)(F)F)CCC1OC1=CC=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=C1 OQOPMDUTIYDECV-UHFFFAOYSA-N 0.000 description 1
- AXACBBYHKIIVMA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(3-methoxy-2-methylpropanoyl)piperidin-4-yl]oxybenzamide Chemical compound C1CN(C(=O)C(C)COC)CCC1OC1=CC=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=C1 AXACBBYHKIIVMA-UHFFFAOYSA-N 0.000 description 1
- DFDBZRDSNXXVRJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(oxane-4-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]benzamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)=CCN1C(=O)C1CCOCC1 DFDBZRDSNXXVRJ-UHFFFAOYSA-N 0.000 description 1
- KJPDXCWJNUOVFH-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(oxane-4-carbonyl)piperidin-4-yl]oxybenzamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(C=C1)=CC=C1OC(CC1)CCN1C(=O)C1CCOCC1 KJPDXCWJNUOVFH-UHFFFAOYSA-N 0.000 description 1
- PYKZTCBXINEENJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(oxolane-2-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]benzamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)=CCN1C(=O)C1CCCO1 PYKZTCBXINEENJ-UHFFFAOYSA-N 0.000 description 1
- ZIAGDSHACZLIBV-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(oxolane-3-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]benzamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)=CCN1C(=O)C1CCOC1 ZIAGDSHACZLIBV-UHFFFAOYSA-N 0.000 description 1
- KJNIBUNKLPJQGA-JOCHJYFZSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-[(2r)-oxolane-2-carbonyl]piperidin-4-yl]oxybenzamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(C=C1)=CC=C1OC(CC1)CCN1C(=O)[C@H]1CCCO1 KJNIBUNKLPJQGA-JOCHJYFZSA-N 0.000 description 1
- KJNIBUNKLPJQGA-QFIPXVFZSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-[(2s)-oxolane-2-carbonyl]piperidin-4-yl]oxybenzamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(C=C1)=CC=C1OC(CC1)CCN1C(=O)[C@@H]1CCCO1 KJNIBUNKLPJQGA-QFIPXVFZSA-N 0.000 description 1
- QBRQIVLBVBRKHY-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-[2-(2-methoxyethoxy)acetyl]-3,6-dihydro-2h-pyridin-4-yl]benzamide Chemical compound C1N(C(=O)COCCOC)CCC(C=2C=CC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)=C1 QBRQIVLBVBRKHY-UHFFFAOYSA-N 0.000 description 1
- QHJAWQXTOVYHCP-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-[2-(oxan-4-yl)acetyl]-3,6-dihydro-2h-pyridin-4-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)=CCN1C(=O)CC1CCOCC1 QHJAWQXTOVYHCP-UHFFFAOYSA-N 0.000 description 1
- FVWXWUMAJXZXLT-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-[2-(oxan-4-yl)acetyl]piperidin-4-yl]oxybenzamide Chemical compound C1CC(OC=2C=CC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)CCN1C(=O)CC1CCOCC1 FVWXWUMAJXZXLT-UHFFFAOYSA-N 0.000 description 1
- BBWQPTLIICUFBR-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-[2-(oxolan-2-yl)acetyl]-3,6-dihydro-2h-pyridin-4-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)=CCN1C(=O)CC1CCCO1 BBWQPTLIICUFBR-UHFFFAOYSA-N 0.000 description 1
- FMXPTVVRNXUYAL-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-[2-(oxolan-2-yl)acetyl]piperidin-4-yl]oxybenzamide Chemical compound C1CC(OC=2C=CC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)CCN1C(=O)CC1CCCO1 FMXPTVVRNXUYAL-UHFFFAOYSA-N 0.000 description 1
- UOHVYCJMEDEFQG-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-[2-(oxolan-3-yl)acetyl]-3,6-dihydro-2h-pyridin-4-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)=CCN1C(=O)CC1CCOC1 UOHVYCJMEDEFQG-UHFFFAOYSA-N 0.000 description 1
- QWIGLBINJAWRHD-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-[3-(oxolan-2-yl)propanoyl]-3,6-dihydro-2h-pyridin-4-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)=CCN1C(=O)CCC1CCCO1 QWIGLBINJAWRHD-UHFFFAOYSA-N 0.000 description 1
- HNJOQJRQHCMBKI-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[[2-(oxan-4-yl)acetyl]amino]benzamide Chemical compound C=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CC1CCOCC1 HNJOQJRQHCMBKI-UHFFFAOYSA-N 0.000 description 1
- CLVWRWCZVMSNNL-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[[2-(oxolan-2-yl)acetyl]amino]benzamide Chemical compound C=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CC1CCCO1 CLVWRWCZVMSNNL-UHFFFAOYSA-N 0.000 description 1
- TWHDVOWFLKOBAJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[[2-(oxolan-3-yl)acetyl]amino]benzamide Chemical compound C=1C=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CC1CCOC1 TWHDVOWFLKOBAJ-UHFFFAOYSA-N 0.000 description 1
- HAYCXLBUNOKBNC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropanoyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=NN(C(=O)C(C)C)C=C1C1=CC=C(C(=O)NCC2=CN3C=CN=C3C=C2)S1 HAYCXLBUNOKBNC-UHFFFAOYSA-N 0.000 description 1
- UCGUGRPZDNCFHS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)pyrazol-4-yl]furan-2-carboxamide Chemical compound C1=NN(CC(C)C)C=C1C1=CC=C(C(=O)NCC2=CN3C=CN=C3C=C2)O1 UCGUGRPZDNCFHS-UHFFFAOYSA-N 0.000 description 1
- UFRCJEQHOOYXPN-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=NN(CC(C)C)C=C1C1=CC=C(C(=O)NCC2=CN3C=CN=C3C=C2)S1 UFRCJEQHOOYXPN-UHFFFAOYSA-N 0.000 description 1
- QOEMWUAOSDJDPV-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(oxan-2-ylmethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1CCCCO1 QOEMWUAOSDJDPV-UHFFFAOYSA-N 0.000 description 1
- SWGIDALOIAOZFT-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(oxan-3-ylmethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1CCCOC1 SWGIDALOIAOZFT-UHFFFAOYSA-N 0.000 description 1
- MPQJVKHWOKGGLA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(oxan-4-ylmethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1CCOCC1 MPQJVKHWOKGGLA-UHFFFAOYSA-N 0.000 description 1
- RICMOSPCIDVNQF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(oxolan-2-ylmethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1CCCO1 RICMOSPCIDVNQF-UHFFFAOYSA-N 0.000 description 1
- SYZQXYIYISNVAJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(oxolan-3-ylmethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CC2=NC=CN2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1CCOC1 SYZQXYIYISNVAJ-UHFFFAOYSA-N 0.000 description 1
- JDBZSWRPLFGLLJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-[(3-methyloxetan-3-yl)methyl]pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=C(C=2SC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)C=NN1CC1(C)COC1 JDBZSWRPLFGLLJ-UHFFFAOYSA-N 0.000 description 1
- FUENPQXJXBSQLC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-1-[1-(3-methylbutanoyl)piperidin-4-yl]pyrazole-3-carboxamide Chemical compound C1CN(C(=O)CC(C)C)CCC1N1N=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 FUENPQXJXBSQLC-UHFFFAOYSA-N 0.000 description 1
- BPMSWPMRJUVNEZ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1-phenylpiperidin-4-yl)-1,3-thiazole-5-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CN=C1C(CC1)CCN1C1=CC=CC=C1 BPMSWPMRJUVNEZ-UHFFFAOYSA-N 0.000 description 1
- RJIAHFJCYCIPNE-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1-pyridin-2-ylpiperidin-4-yl)-1,3-thiazole-5-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CN=C1C(CC1)CCN1C1=CC=CC=N1 RJIAHFJCYCIPNE-UHFFFAOYSA-N 0.000 description 1
- MFAIGNRCPBSYOG-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(4-propan-2-ylpiperazin-1-yl)-1,3-thiazole-5-carboxamide Chemical compound C1CN(C(C)C)CCN1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 MFAIGNRCPBSYOG-UHFFFAOYSA-N 0.000 description 1
- XGSJFCSNRAMXQP-GOSISDBHSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4r)-2-oxo-4-(phenylmethoxymethyl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound C([C@H]1N(C(OC1)=O)C1=NC=C(S1)C(NCC1=CC2=NC=CN2C=C1)=O)OCC1=CC=CC=C1 XGSJFCSNRAMXQP-GOSISDBHSA-N 0.000 description 1
- AHIMFJMKCOBQTL-ZDUSSCGKSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4r)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC(C)[C@@H]1COC(=O)N1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 AHIMFJMKCOBQTL-ZDUSSCGKSA-N 0.000 description 1
- IEQHEIPMKBLDEG-SNVBAGLBSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4r)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound C[C@@H]1COC(=O)N1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 IEQHEIPMKBLDEG-SNVBAGLBSA-N 0.000 description 1
- XGSJFCSNRAMXQP-SFHVURJKSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4s)-2-oxo-4-(phenylmethoxymethyl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound C([C@@H]1N(C(OC1)=O)C1=NC=C(S1)C(NCC1=CC2=NC=CN2C=C1)=O)OCC1=CC=CC=C1 XGSJFCSNRAMXQP-SFHVURJKSA-N 0.000 description 1
- AHIMFJMKCOBQTL-CYBMUJFWSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4s)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC(C)[C@H]1COC(=O)N1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 AHIMFJMKCOBQTL-CYBMUJFWSA-N 0.000 description 1
- QZFPIIMTLXAHLJ-CQSZACIVSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(5r)-2-oxo-5-(propan-2-yloxymethyl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound O=C1O[C@@H](COC(C)C)CN1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 QZFPIIMTLXAHLJ-CQSZACIVSA-N 0.000 description 1
- QZFPIIMTLXAHLJ-AWEZNQCLSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(5s)-2-oxo-5-(propan-2-yloxymethyl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound O=C1O[C@H](COC(C)C)CN1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 QZFPIIMTLXAHLJ-AWEZNQCLSA-N 0.000 description 1
- OXFKCKMWSZQQQP-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)-3,6-dihydro-2h-pyridin-4-yl]-1,3-thiazole-5-carboxamide Chemical compound C1N(C(=O)C(C)C)CCC(C=2SC(=CN=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 OXFKCKMWSZQQQP-UHFFFAOYSA-N 0.000 description 1
- WUMKZAHTJDLIQJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide Chemical compound C1CN(C(=O)C(C)C)CCC1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 WUMKZAHTJDLIQJ-UHFFFAOYSA-N 0.000 description 1
- NXQNZNIKZAKAMG-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound C1N(C(=O)C(C)C)CCC1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 NXQNZNIKZAKAMG-UHFFFAOYSA-N 0.000 description 1
- UHZKDPYOZAALMN-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropyl)pyrazol-4-yl]-1,3-thiazole-5-carboxamide Chemical compound C1=NN(CC(C)C)C=C1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 UHZKDPYOZAALMN-UHFFFAOYSA-N 0.000 description 1
- RGLGMGMKTDQPEG-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropylsulfonyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound C1N(S(=O)(=O)CC(C)C)CCC1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 RGLGMGMKTDQPEG-UHFFFAOYSA-N 0.000 description 1
- FKMAFSWKICQHEB-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide Chemical compound C1CN(C(=O)CC(C)C)CCC1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 FKMAFSWKICQHEB-UHFFFAOYSA-N 0.000 description 1
- IPTIICKBGIDOCD-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound C1N(C(=O)CC(C)C)CCC1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 IPTIICKBGIDOCD-UHFFFAOYSA-N 0.000 description 1
- OTOPIXPTQGYBCT-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(oxane-4-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]-1,3-thiazole-5-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CN=C1C(CC1)=CCN1C(=O)C1CCOCC1 OTOPIXPTQGYBCT-UHFFFAOYSA-N 0.000 description 1
- PNRNCIOKMIRWDL-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[2-methoxyethylcarbamoyl(oxolan-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)SC=1N(C(=O)NCCOC)CC1CCCO1 PNRNCIOKMIRWDL-UHFFFAOYSA-N 0.000 description 1
- BHLMAWDHNMEEFX-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[2-oxo-5-(phenylmethoxymethyl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CN=C1N(C(O1)=O)CC1COCC1=CC=CC=C1 BHLMAWDHNMEEFX-UHFFFAOYSA-N 0.000 description 1
- QZFPIIMTLXAHLJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[2-oxo-5-(propan-2-yloxymethyl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound O=C1OC(COC(C)C)CN1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 QZFPIIMTLXAHLJ-UHFFFAOYSA-N 0.000 description 1
- FSONBQLIQXWPIR-GOSISDBHSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[3-(1,2-oxazol-4-yl)propanoyl-[[(2r)-oxolan-2-yl]methyl]amino]-1,3-thiazole-5-carboxamide Chemical compound C([C@@H]1OCCC1)N(C=1SC(=CN=1)C(=O)NCC1=CC2=NC=CN2C=C1)C(=O)CCC=1C=NOC=1 FSONBQLIQXWPIR-GOSISDBHSA-N 0.000 description 1
- DLMXCEVJGNWCJR-GOSISDBHSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[3-(1,2-oxazol-5-yl)propanoyl-[[(2r)-oxolan-2-yl]methyl]amino]-1,3-thiazole-5-carboxamide Chemical compound C([C@@H]1OCCC1)N(C=1SC(=CN=1)C(=O)NCC1=CC2=NC=CN2C=C1)C(=O)CCC1=CC=NO1 DLMXCEVJGNWCJR-GOSISDBHSA-N 0.000 description 1
- QUMHICYSGHNLSC-LJQANCHMSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[3-(1-methylpyrazol-4-yl)propanoyl-[[(2r)-oxolan-2-yl]methyl]amino]-1,3-thiazole-5-carboxamide Chemical compound C1=NN(C)C=C1CCC(=O)N(C=1SC(=CN=1)C(=O)NCC1=CC2=NC=CN2C=C1)C[C@@H]1OCCC1 QUMHICYSGHNLSC-LJQANCHMSA-N 0.000 description 1
- ZFJKRRJTUPFSJC-HXUWFJFHSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[3-(1-methylpyrrol-2-yl)propanoyl-[[(2r)-oxolan-2-yl]methyl]amino]-1,3-thiazole-5-carboxamide Chemical compound CN1C=CC=C1CCC(=O)N(C=1SC(=CN=1)C(=O)NCC1=CC2=NC=CN2C=C1)C[C@@H]1OCCC1 ZFJKRRJTUPFSJC-HXUWFJFHSA-N 0.000 description 1
- ZPHARPLCXPHBGN-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[3-methoxypropanoyl(oxolan-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)SC=1N(C(=O)CCOC)CC1CCCO1 ZPHARPLCXPHBGN-UHFFFAOYSA-N 0.000 description 1
- AZMNQBPNYGJYPQ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(2-methoxyethyl)piperazin-1-yl]-1,3-thiazole-5-carboxamide Chemical compound C1CN(CCOC)CCN1C1=NC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 AZMNQBPNYGJYPQ-UHFFFAOYSA-N 0.000 description 1
- ZLQQRHREUMXTEU-QGZVFWFLSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[[(2r)-oxolan-2-yl]methyl-[2-(1,3-thiazol-4-yl)acetyl]amino]-1,3-thiazole-5-carboxamide Chemical compound C([C@@H]1OCCC1)N(C=1SC(=CN=1)C(=O)NCC1=CC2=NC=CN2C=C1)C(=O)CC1=CSC=N1 ZLQQRHREUMXTEU-QGZVFWFLSA-N 0.000 description 1
- WCRKUZIPTLSOCG-QGZVFWFLSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[[2-(1,2-oxazol-3-yl)acetyl]-[[(2r)-oxolan-2-yl]methyl]amino]-1,3-thiazole-5-carboxamide Chemical compound C([C@@H]1OCCC1)N(C=1SC(=CN=1)C(=O)NCC1=CC2=NC=CN2C=C1)C(=O)CC=1C=CON=1 WCRKUZIPTLSOCG-QGZVFWFLSA-N 0.000 description 1
- FMFOIMQGUNQHTO-GOSISDBHSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[[2-(1-methylpyrazol-4-yl)acetyl]-[[(2r)-oxolan-2-yl]methyl]amino]-1,3-thiazole-5-carboxamide Chemical compound C1=NN(C)C=C1CC(=O)N(C=1SC(=CN=1)C(=O)NCC1=CC2=NC=CN2C=C1)C[C@@H]1OCCC1 FMFOIMQGUNQHTO-GOSISDBHSA-N 0.000 description 1
- YQYJQYBXUSKPDR-GOSISDBHSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[[2-(5-methyl-1,2-oxazol-3-yl)acetyl]-[[(2r)-oxolan-2-yl]methyl]amino]-1,3-thiazole-5-carboxamide Chemical compound O1C(C)=CC(CC(=O)N(C[C@@H]2OCCC2)C=2SC(=CN=2)C(=O)NCC2=CC3=NC=CN3C=C2)=N1 YQYJQYBXUSKPDR-GOSISDBHSA-N 0.000 description 1
- RTTZPSDCITVZRH-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-phenyl-1,3-thiazole-5-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CN=C1C1=CC=CC=C1 RTTZPSDCITVZRH-UHFFFAOYSA-N 0.000 description 1
- IBBHOENOMCVPJJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-methylsulfonylazetidin-3-yl)benzamide Chemical compound C1N(S(=O)(=O)C)CC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 IBBHOENOMCVPJJ-UHFFFAOYSA-N 0.000 description 1
- SOGPXXSBYVAVRT-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-methylsulfonylpyrrolidin-3-yl)benzamide Chemical compound C1N(S(=O)(=O)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 SOGPXXSBYVAVRT-UHFFFAOYSA-N 0.000 description 1
- BHHCTNZEXUJYDM-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-propan-2-ylsulfonylazetidin-3-yl)benzamide Chemical compound C1N(S(=O)(=O)C(C)C)CC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 BHHCTNZEXUJYDM-UHFFFAOYSA-N 0.000 description 1
- DWTPEQDNAVMYOM-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-propan-2-ylsulfonylpiperidin-4-yl)benzamide Chemical compound C1CN(S(=O)(=O)C(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 DWTPEQDNAVMYOM-UHFFFAOYSA-N 0.000 description 1
- DESOZINIYLXPGW-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-propan-2-ylsulfonylpyrrolidin-3-yl)benzamide Chemical compound C1N(S(=O)(=O)C(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 DESOZINIYLXPGW-UHFFFAOYSA-N 0.000 description 1
- BBPIFYHQGAXFFR-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-propanoylpiperidin-4-yl)benzamide Chemical compound C1CN(C(=O)CC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 BBPIFYHQGAXFFR-UHFFFAOYSA-N 0.000 description 1
- LHSLAVSFRKNUTR-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-pyrimidin-4-yl-3,6-dihydro-2h-pyridin-4-yl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)=CCN1C1=CC=NC=N1 LHSLAVSFRKNUTR-UHFFFAOYSA-N 0.000 description 1
- JBNNYZVEHYOCGK-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(2-propan-2-ylpyrrolidine-1-carbonyl)benzamide Chemical compound CC(C)C1CCCN1C(=O)C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 JBNNYZVEHYOCGK-UHFFFAOYSA-N 0.000 description 1
- ZYJJKVUTOZBQCA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(4-methylpentanoylamino)benzamide Chemical compound C1=CC(NC(=O)CCC(C)C)=CC=C1C(=O)NCC1=CC2=NC=CN2C=C1 ZYJJKVUTOZBQCA-UHFFFAOYSA-N 0.000 description 1
- KTUYTEXXAOKSDS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidine-1-carbonyl)benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(=O)N1CCCCC1 KTUYTEXXAOKSDS-UHFFFAOYSA-N 0.000 description 1
- CUKRYSDDNWCDJC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(2-methyl-2-phenylpropanoyl)amino]benzamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=CC=1NC(=O)C(C)(C)C1=CC=CC=C1 CUKRYSDDNWCDJC-UHFFFAOYSA-N 0.000 description 1
- KXFAUJSCRUPKBS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(2-phenylacetyl)amino]benzamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=CC=1NC(=O)CC1=CC=CC=C1 KXFAUJSCRUPKBS-UHFFFAOYSA-N 0.000 description 1
- KBRWLBNPPBGXKV-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(2-propan-2-yloxyacetyl)amino]benzamide Chemical compound C1=CC(NC(=O)COC(C)C)=CC=C1C(=O)NCC1=CC2=NC=CN2C=C1 KBRWLBNPPBGXKV-UHFFFAOYSA-N 0.000 description 1
- DCBABALBLAFNCG-LJQANCHMSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(2r)-2-(methoxymethyl)pyrrolidine-1-carbonyl]benzamide Chemical compound COC[C@H]1CCCN1C(=O)C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 DCBABALBLAFNCG-LJQANCHMSA-N 0.000 description 1
- VPVFRDMNHBQMQY-HXUWFJFHSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(3r)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxybenzamide Chemical compound C1N(C(=O)C(C)C)CC[C@H]1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 VPVFRDMNHBQMQY-HXUWFJFHSA-N 0.000 description 1
- OVVUKHIRZZNNOW-LAUBAEHRSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(3r)-1-[(2s)-2-methylbutanoyl]pyrrolidin-3-yl]oxybenzamide Chemical compound C1N(C(=O)[C@@H](C)CC)CC[C@H]1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 OVVUKHIRZZNNOW-LAUBAEHRSA-N 0.000 description 1
- QDZRWPQQZXPYIH-PZJWPPBQSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(3r)-1-[(3s)-oxolane-3-carbonyl]pyrrolidin-3-yl]oxybenzamide Chemical compound C([C@H](C1)OC2=CC=C(C=C2)C(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)[C@H]1CCOC1 QDZRWPQQZXPYIH-PZJWPPBQSA-N 0.000 description 1
- VPVFRDMNHBQMQY-FQEVSTJZSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(3s)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxybenzamide Chemical compound C1N(C(=O)C(C)C)CC[C@@H]1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 VPVFRDMNHBQMQY-FQEVSTJZSA-N 0.000 description 1
- OXDIBSMOLTUEDT-LFABVHOISA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(3s)-1-(3-methoxy-2-methylpropanoyl)pyrrolidin-3-yl]oxybenzamide Chemical compound C1N(C(=O)C(C)COC)CC[C@@H]1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 OXDIBSMOLTUEDT-LFABVHOISA-N 0.000 description 1
- NQUPKTBTGBGJAP-QFIPXVFZSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(3s)-1-(oxane-4-carbonyl)pyrrolidin-3-yl]oxybenzamide Chemical compound C([C@@H](C1)OC2=CC=C(C=C2)C(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)C1CCOCC1 NQUPKTBTGBGJAP-QFIPXVFZSA-N 0.000 description 1
- MWEXCBSMYBSGNK-LEWJYISDSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(3s)-1-[(2r)-oxolane-2-carbonyl]pyrrolidin-3-yl]oxybenzamide Chemical compound C([C@@H](C1)OC2=CC=C(C=C2)C(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)[C@H]1CCCO1 MWEXCBSMYBSGNK-LEWJYISDSA-N 0.000 description 1
- OVVUKHIRZZNNOW-UWJYYQICSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(3s)-1-[(2s)-2-methylbutanoyl]pyrrolidin-3-yl]oxybenzamide Chemical compound C1N(C(=O)[C@@H](C)CC)CC[C@@H]1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 OVVUKHIRZZNNOW-UWJYYQICSA-N 0.000 description 1
- MWEXCBSMYBSGNK-SFTDATJTSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(3s)-1-[(2s)-oxolane-2-carbonyl]pyrrolidin-3-yl]oxybenzamide Chemical compound C([C@@H](C1)OC2=CC=C(C=C2)C(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)[C@@H]1CCCO1 MWEXCBSMYBSGNK-SFTDATJTSA-N 0.000 description 1
- QDZRWPQQZXPYIH-CTNGQTDRSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(3s)-1-[(3r)-oxolane-3-carbonyl]pyrrolidin-3-yl]oxybenzamide Chemical compound C([C@@H](C1)OC2=CC=C(C=C2)C(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)[C@@H]1CCOC1 QDZRWPQQZXPYIH-CTNGQTDRSA-N 0.000 description 1
- QDZRWPQQZXPYIH-FPOVZHCZSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(3s)-1-[(3s)-oxolane-3-carbonyl]pyrrolidin-3-yl]oxybenzamide Chemical compound C([C@@H](C1)OC2=CC=C(C=C2)C(NCC2=CC3=NC=CN3C=C2)=O)CN1C(=O)[C@H]1CCOC1 QDZRWPQQZXPYIH-FPOVZHCZSA-N 0.000 description 1
- FRDHVHPBANAKEE-QHCPKHFHSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(3s)-1-[2-(oxan-4-yl)acetyl]pyrrolidin-3-yl]oxybenzamide Chemical compound C([C@H](CC1)OC=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)N1C(=O)CC1CCOCC1 FRDHVHPBANAKEE-QHCPKHFHSA-N 0.000 description 1
- XFDQFHKRUCUAII-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazole-2-carbonyl)azetidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C1=NC=CS1 XFDQFHKRUCUAII-UHFFFAOYSA-N 0.000 description 1
- NONQANZZXBJIFS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazole-2-carbonyl)pyrrolidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C1=NC=CS1 NONQANZZXBJIFS-UHFFFAOYSA-N 0.000 description 1
- SYMFWHQVHZSIBX-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazole-4-carbonyl)azetidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C1=CSC=N1 SYMFWHQVHZSIBX-UHFFFAOYSA-N 0.000 description 1
- ILIRYPZLZGCGGM-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazole-4-carbonyl)pyrrolidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C1=CSC=N1 ILIRYPZLZGCGGM-UHFFFAOYSA-N 0.000 description 1
- UQKHWPYINJTFPJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazole-5-carbonyl)azetidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C1=CN=CS1 UQKHWPYINJTFPJ-UHFFFAOYSA-N 0.000 description 1
- LTXFFXLGAKUWGW-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazole-5-carbonyl)pyrrolidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C1=CN=CS1 LTXFFXLGAKUWGW-UHFFFAOYSA-N 0.000 description 1
- QLXVAVLWVJOTEG-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-methyl-4,5,6,7-tetrahydroindazole-3-carbonyl)piperidin-4-yl]benzamide Chemical compound C1CCCC2=C1C(C(=O)N1CCC(CC1)C=1C=CC(=CC=1)C(=O)NCC1=CC3=NC=CN3C=C1)=NN2C QLXVAVLWVJOTEG-UHFFFAOYSA-N 0.000 description 1
- FYLSOHKWENLLCA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-methyl-5-propylpyrazole-4-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=NN(C)C(CCC)=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 FYLSOHKWENLLCA-UHFFFAOYSA-N 0.000 description 1
- XJUJRHWNSZJOID-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-methylcyclohexanecarbonyl)azetidin-3-yl]benzamide Chemical compound C1C(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)C1(C)CCCCC1 XJUJRHWNSZJOID-UHFFFAOYSA-N 0.000 description 1
- DDUIKJAQUDCSOM-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-methylcyclohexanecarbonyl)pyrrolidin-3-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)C1(C)CCCCC1 DDUIKJAQUDCSOM-UHFFFAOYSA-N 0.000 description 1
- VRZXYMSEMLEJAS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-methylcyclopropanecarbonyl)azetidin-3-yl]benzamide Chemical compound C1C(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)C1(C)CC1 VRZXYMSEMLEJAS-UHFFFAOYSA-N 0.000 description 1
- HQFFTIVVGNOMKB-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)C1(C)CC1 HQFFTIVVGNOMKB-UHFFFAOYSA-N 0.000 description 1
- AVJXKWSMMYLXTL-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-methylcyclopropanecarbonyl)pyrrolidin-3-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)C1(C)CC1 AVJXKWSMMYLXTL-UHFFFAOYSA-N 0.000 description 1
- UROLTAOABPUAOY-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-methylindazole-4-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=C2C=NN(C)C2=CC=C1 UROLTAOABPUAOY-UHFFFAOYSA-N 0.000 description 1
- LFEFBQUFPLLEKS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-methylindazole-6-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=C2C=NN(C)C2=C1 LFEFBQUFPLLEKS-UHFFFAOYSA-N 0.000 description 1
- YTRFBYVVALPPTF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-methylpyrazole-3-carbonyl)azetidin-3-yl]benzamide Chemical compound CN1C=CC(C(=O)N2CC(C2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=N1 YTRFBYVVALPPTF-UHFFFAOYSA-N 0.000 description 1
- OHYULATUSXSZAW-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-methylpyrazole-3-carbonyl)pyrrolidin-3-yl]benzamide Chemical compound CN1C=CC(C(=O)N2CC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=N1 OHYULATUSXSZAW-UHFFFAOYSA-N 0.000 description 1
- YLOAKAOBOZAGPF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-methylpyrazole-4-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=NN(C)C=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 YLOAKAOBOZAGPF-UHFFFAOYSA-N 0.000 description 1
- HMFURVAECAWHJF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-methylpyrrole-2-carbonyl)azetidin-3-yl]benzamide Chemical compound CN1C=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C1 HMFURVAECAWHJF-UHFFFAOYSA-N 0.000 description 1
- DRFSKPVKUYRXJE-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-methylpyrrole-2-carbonyl)piperidin-4-yl]benzamide Chemical compound CN1C=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 DRFSKPVKUYRXJE-UHFFFAOYSA-N 0.000 description 1
- NNUDWYQULNWTGJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-methylpyrrole-2-carbonyl)pyrrolidin-3-yl]benzamide Chemical compound CN1C=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 NNUDWYQULNWTGJ-UHFFFAOYSA-N 0.000 description 1
- QMRGKSPOWUGPLM-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-propan-2-ylpyrazole-3-carbonyl)piperidin-4-yl]benzamide Chemical compound CC(C)N1C=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=N1 QMRGKSPOWUGPLM-UHFFFAOYSA-N 0.000 description 1
- WAADXMNAHSTCEC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1-pyridin-2-ylcyclopropanecarbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1(C=2N=CC=CC=2)CC1 WAADXMNAHSTCEC-UHFFFAOYSA-N 0.000 description 1
- KNYTUXMNIFGVIF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxy-5-methylpyridine-3-carbonyl)piperidin-4-yl]benzamide Chemical compound COC1=NC=C(C)C=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 KNYTUXMNIFGVIF-UHFFFAOYSA-N 0.000 description 1
- XESGJGZBEJZTPF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)azetidin-3-yl]benzamide Chemical compound COC1=CC=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C1 XESGJGZBEJZTPF-UHFFFAOYSA-N 0.000 description 1
- LUHLXLCOYBVSIE-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)piperidin-4-yl]benzamide Chemical compound COC1=CC=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 LUHLXLCOYBVSIE-UHFFFAOYSA-N 0.000 description 1
- CXBHWTSBWOPBFO-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]benzamide Chemical compound COC1=CC=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 CXBHWTSBWOPBFO-UHFFFAOYSA-N 0.000 description 1
- QQOKPYVGMJBTJQ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methyl-1,3-benzoxazole-6-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=C2N=C(C)OC2=C1 QQOKPYVGMJBTJQ-UHFFFAOYSA-N 0.000 description 1
- DKBTTXWLRMHKLI-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methyl-2,3-dihydro-1-benzofuran-7-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=C(OC(C)C2)C2=CC=C1 DKBTTXWLRMHKLI-UHFFFAOYSA-N 0.000 description 1
- PBHMQYVVRGJEGI-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methyl-2-phenylpropanoyl)pyrrolidin-3-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)C(C)(C)C1=CC=CC=C1 PBHMQYVVRGJEGI-UHFFFAOYSA-N 0.000 description 1
- NWILEHOFADHOBO-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methyl-4,5,6,7-tetrahydroindazole-3-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=C2CCCCC2=NN1C NWILEHOFADHOBO-UHFFFAOYSA-N 0.000 description 1
- NABYNEFGYBWFLA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methyl-5-propan-2-ylfuran-3-carbonyl)piperidin-4-yl]benzamide Chemical compound O1C(C(C)C)=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1C NABYNEFGYBWFLA-UHFFFAOYSA-N 0.000 description 1
- XXWIDJZKYIVBSF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)azetidin-3-yl]benzamide Chemical compound CC1=CC=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C1 XXWIDJZKYIVBSF-UHFFFAOYSA-N 0.000 description 1
- UWPTVMQXQKOBFT-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)piperidin-4-yl]benzamide Chemical compound CC1=CC=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 UWPTVMQXQKOBFT-UHFFFAOYSA-N 0.000 description 1
- AYPHZFWOJSZOKV-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)pyrrolidin-3-yl]benzamide Chemical compound CC1=CC=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 AYPHZFWOJSZOKV-UHFFFAOYSA-N 0.000 description 1
- CBVPFWJZDMSLBY-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylcyclopentene-1-carbonyl)piperidin-4-yl]benzamide Chemical compound C1CCC(C)=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 CBVPFWJZDMSLBY-UHFFFAOYSA-N 0.000 description 1
- LLYCWYAYHXOZSN-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylcyclopropanecarbonyl)azetidin-3-yl]benzamide Chemical compound CC1CC1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C1 LLYCWYAYHXOZSN-UHFFFAOYSA-N 0.000 description 1
- SOWQEUKKCKEXFB-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylcyclopropanecarbonyl)pyrrolidin-3-yl]benzamide Chemical compound CC1CC1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 SOWQEUKKCKEXFB-UHFFFAOYSA-N 0.000 description 1
- SJNBLFPRZLGXHK-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylindazole-4-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CC2=NN(C)C=C21 SJNBLFPRZLGXHK-UHFFFAOYSA-N 0.000 description 1
- QVCJKPAGFYIJBQ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylindazole-6-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC2=NN(C)C=C2C=C1 QVCJKPAGFYIJBQ-UHFFFAOYSA-N 0.000 description 1
- RBBNPVBHBUXMRS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)azetidin-3-yl]benzamide Chemical compound C1N(C(=O)C(C)C)CC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 RBBNPVBHBUXMRS-UHFFFAOYSA-N 0.000 description 1
- KYIFJNGXVHWBHI-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)azetidin-3-yl]oxybenzamide Chemical compound C1N(C(=O)C(C)C)CC1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 KYIFJNGXVHWBHI-UHFFFAOYSA-N 0.000 description 1
- XHXXKDKXCAMGCF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide Chemical compound C1CN(C(=O)C(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 XHXXKDKXCAMGCF-UHFFFAOYSA-N 0.000 description 1
- IGOZIBLQEJVBLI-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]oxybenzamide Chemical compound C1CN(C(=O)C(C)C)CCC1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 IGOZIBLQEJVBLI-UHFFFAOYSA-N 0.000 description 1
- LQZLKINPCZXDQD-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]benzamide Chemical compound C1N(C(=O)C(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 LQZLKINPCZXDQD-UHFFFAOYSA-N 0.000 description 1
- JFQIKPSCCHUKLD-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropyl)pyrazol-4-yl]benzamide Chemical compound C1=NN(CC(C)C)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 JFQIKPSCCHUKLD-UHFFFAOYSA-N 0.000 description 1
- AAQOKGNGSJWIMT-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpyrazole-3-carbonyl)piperidin-4-yl]benzamide Chemical compound CN1N=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 AAQOKGNGSJWIMT-UHFFFAOYSA-N 0.000 description 1
- FIKNWNDNZJWOKI-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpyrimidin-4-yl)-3,6-dihydro-2h-pyridin-4-yl]benzamide Chemical compound CC1=NC=CC(N2CC=C(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=N1 FIKNWNDNZJWOKI-UHFFFAOYSA-N 0.000 description 1
- NSWLKWNNVPRRLW-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-morpholin-4-ylacetyl)piperidin-4-yl]oxybenzamide Chemical compound C1CC(OC=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)CN1CCOCC1 NSWLKWNNVPRRLW-UHFFFAOYSA-N 0.000 description 1
- AJPNFFJSKMSXNF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-oxobutanoyl)piperidin-4-yl]benzamide Chemical compound C1CN(C(=O)C(=O)CC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 AJPNFFJSKMSXNF-UHFFFAOYSA-N 0.000 description 1
- HKFLFKNQPRFWOV-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenoxypropanoyl)piperidin-4-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)C(C)OC1=CC=CC=C1 HKFLFKNQPRFWOV-UHFFFAOYSA-N 0.000 description 1
- RWBBSWOZJAEIFQ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenylacetyl)piperidin-4-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)CC1=CC=CC=C1 RWBBSWOZJAEIFQ-UHFFFAOYSA-N 0.000 description 1
- VHHCECUYARZLNJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenylacetyl)pyrrolidin-3-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)CC1=CC=CC=C1 VHHCECUYARZLNJ-UHFFFAOYSA-N 0.000 description 1
- SSWFKZDMRFGXSU-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenylpropanoyl)piperidin-4-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)C(C)C1=CC=CC=C1 SSWFKZDMRFGXSU-UHFFFAOYSA-N 0.000 description 1
- XQRZUGDSUNAYMG-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-propan-2-yl-1,3-oxazole-4-carbonyl)piperidin-4-yl]benzamide Chemical compound O1C(C(C)C)=NC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 XQRZUGDSUNAYMG-UHFFFAOYSA-N 0.000 description 1
- PSRRLTIUQWLAAP-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-propan-2-yl-1,3-thiazole-4-carbonyl)piperidin-4-yl]benzamide Chemical compound S1C(C(C)C)=NC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 PSRRLTIUQWLAAP-UHFFFAOYSA-N 0.000 description 1
- YYPVIOVTYKZPRE-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-propan-2-yloxane-4-carbonyl)piperidin-4-yl]benzamide Chemical compound C1COC(C(C)C)CC1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 YYPVIOVTYKZPRE-UHFFFAOYSA-N 0.000 description 1
- WTGZLQSAKICHTQ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-propan-2-yloxyacetyl)piperidin-4-yl]benzamide Chemical compound C1CN(C(=O)COC(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 WTGZLQSAKICHTQ-UHFFFAOYSA-N 0.000 description 1
- CHTBHSQMLZSPJJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-propan-2-yloxyacetyl)piperidin-4-yl]oxybenzamide Chemical compound C1CN(C(=O)COC(C)C)CCC1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 CHTBHSQMLZSPJJ-UHFFFAOYSA-N 0.000 description 1
- LTCXAQBZSOCJJM-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-propan-2-yloxyacetyl)pyrrolidin-3-yl]benzamide Chemical compound C1N(C(=O)COC(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 LTCXAQBZSOCJJM-UHFFFAOYSA-N 0.000 description 1
- YPWLAMBOFLVFJD-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-propan-2-ylpyrimidine-4-carbonyl)piperidin-4-yl]benzamide Chemical compound CC(C)C1=NC=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=N1 YPWLAMBOFLVFJD-UHFFFAOYSA-N 0.000 description 1
- SJXVWCZBTJCKKZ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide Chemical compound C1CN(C(=O)CC(F)(F)F)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 SJXVWCZBTJCKKZ-UHFFFAOYSA-N 0.000 description 1
- FVOZMSJETJBHNO-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)azetidin-3-yl]benzamide Chemical compound COC1=CC=CC(C(=O)N2CC(C2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 FVOZMSJETJBHNO-UHFFFAOYSA-N 0.000 description 1
- XBVQHEQJZDSZAY-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)piperidin-4-yl]benzamide Chemical compound COC1=CC=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 XBVQHEQJZDSZAY-UHFFFAOYSA-N 0.000 description 1
- MBCUUYKMGSQHEC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]benzamide Chemical compound COC1=CC=CC(C(=O)N2CC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 MBCUUYKMGSQHEC-UHFFFAOYSA-N 0.000 description 1
- XSMMHHMBIBIISN-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxythiophene-2-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CSC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1OC XSMMHHMBIBIISN-UHFFFAOYSA-N 0.000 description 1
- WTIQKEHOGCTIGX-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine-1-carbonyl)piperidin-4-yl]benzamide Chemical compound C1CCCN2C(C)=NC(C(=O)N3CCC(CC3)C=3C=CC(=CC=3)C(=O)NCC3=CC4=NC=CN4C=C3)=C21 WTIQKEHOGCTIGX-UHFFFAOYSA-N 0.000 description 1
- IBYSNLBWRYRLGY-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)azetidin-3-yl]benzamide Chemical compound CC1=CC=CC(C(=O)N2CC(C2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 IBYSNLBWRYRLGY-UHFFFAOYSA-N 0.000 description 1
- XZDDQEMWWQRYLY-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)pyrrolidin-3-yl]benzamide Chemical compound CC1=CC=CC(C(=O)N2CC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 XZDDQEMWWQRYLY-UHFFFAOYSA-N 0.000 description 1
- KEYYCVFTOXKPKU-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbut-2-enoyl)piperidin-4-yl]benzamide Chemical compound C1CN(C(=O)C=C(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 KEYYCVFTOXKPKU-UHFFFAOYSA-N 0.000 description 1
- KJYHMODDXCXLII-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)azetidin-3-yl]benzamide Chemical compound C1N(C(=O)CC(C)C)CC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 KJYHMODDXCXLII-UHFFFAOYSA-N 0.000 description 1
- CTNLIYWSEMPLOU-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)piperidin-4-yl]benzamide Chemical compound C1CN(C(=O)CC(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 CTNLIYWSEMPLOU-UHFFFAOYSA-N 0.000 description 1
- HMTJEEVZRNWUNW-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)pyrrolidin-3-yl]benzamide Chemical compound C1N(C(=O)CC(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 HMTJEEVZRNWUNW-UHFFFAOYSA-N 0.000 description 1
- MQFXCTUPFHVNAC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methyloxetane-3-carbonyl)piperidin-4-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)C1(C)COC1 MQFXCTUPFHVNAC-UHFFFAOYSA-N 0.000 description 1
- HDMSOPJXQWQCLJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)azetidin-3-yl]benzamide Chemical compound C1N(C(=O)CC(C)CC)CC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 HDMSOPJXQWQCLJ-UHFFFAOYSA-N 0.000 description 1
- QQSPKLIZJAHABM-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)pyrrolidin-3-yl]benzamide Chemical compound C1N(C(=O)CC(C)CC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 QQSPKLIZJAHABM-UHFFFAOYSA-N 0.000 description 1
- ITFVOGPENUGKQK-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylthiophene-2-carbonyl)azetidin-3-yl]benzamide Chemical compound C1=CSC(C(=O)N2CC(C2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1C ITFVOGPENUGKQK-UHFFFAOYSA-N 0.000 description 1
- RCXIXKUOVYPJMA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylthiophene-2-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CSC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1C RCXIXKUOVYPJMA-UHFFFAOYSA-N 0.000 description 1
- DVAOTSPCXVQHIU-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylthiophene-2-carbonyl)pyrrolidin-3-yl]benzamide Chemical compound C1=CSC(C(=O)N2CC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1C DVAOTSPCXVQHIU-UHFFFAOYSA-N 0.000 description 1
- TZBURIPIECMUNJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-1,3-benzothiazole-2-carbonyl)piperidin-4-yl]benzamide Chemical compound C1CCCC(S2)=C1N=C2C(=O)N(CC1)CCC1C(C=C1)=CC=C1C(=O)NCC1=CC2=NC=CN2C=C1 TZBURIPIECMUNJ-UHFFFAOYSA-N 0.000 description 1
- WCLUTKHCJVUPHH-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-2,1-benzoxazole-3-carbonyl)piperidin-4-yl]benzamide Chemical compound O1N=C2CCCCC2=C1C(=O)N(CC1)CCC1C(C=C1)=CC=C1C(=O)NCC1=CC2=NC=CN2C=C1 WCLUTKHCJVUPHH-UHFFFAOYSA-N 0.000 description 1
- PBVAEPYLYULCDL-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxy-5-methylpyridine-2-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=C(C)C(OC)=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=N1 PBVAEPYLYULCDL-UHFFFAOYSA-N 0.000 description 1
- QIWJZEUMTJLFGU-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)azetidin-3-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C1 QIWJZEUMTJLFGU-UHFFFAOYSA-N 0.000 description 1
- TYCRQQLSABIZMX-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)piperidin-4-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 TYCRQQLSABIZMX-UHFFFAOYSA-N 0.000 description 1
- ORDFJBQVGZHXFT-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 ORDFJBQVGZHXFT-UHFFFAOYSA-N 0.000 description 1
- WFEHMPAEUKJBAD-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxycyclohexanecarbonyl)piperidin-4-yl]benzamide Chemical compound C1CC(OC)CCC1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 WFEHMPAEUKJBAD-UHFFFAOYSA-N 0.000 description 1
- JPWVFCSFVQIUHR-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxythiophene-2-carbonyl)piperidin-4-yl]benzamide Chemical compound COC1=CSC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 JPWVFCSFVQIUHR-UHFFFAOYSA-N 0.000 description 1
- MAZMZHUMOQYLCN-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)azetidin-3-yl]benzamide Chemical compound C1=CC(C)=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C1 MAZMZHUMOQYLCN-UHFFFAOYSA-N 0.000 description 1
- YAFGBUKCKKAQMZ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)piperidin-4-yl]benzamide Chemical compound C1=CC(C)=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 YAFGBUKCKKAQMZ-UHFFFAOYSA-N 0.000 description 1
- LCNHQZIIJAFKIR-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)pyrrolidin-3-yl]benzamide Chemical compound C1=CC(C)=CC=C1C(=O)N1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 LCNHQZIIJAFKIR-UHFFFAOYSA-N 0.000 description 1
- FXGMGSBGGGKIRU-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylfuro[3,2-b]pyrrole-5-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C(N1C)=CC2=C1C=CO2 FXGMGSBGGGKIRU-UHFFFAOYSA-N 0.000 description 1
- NLLUBCHGELCGTF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-propan-2-ylpyrimidine-5-carbonyl)piperidin-4-yl]benzamide Chemical compound CC(C)C1=NC=NC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 NLLUBCHGELCGTF-UHFFFAOYSA-N 0.000 description 1
- UELATMAAELOPAO-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(5,6,7,8-tetrahydroquinoline-3-carbonyl)piperidin-4-yl]benzamide Chemical compound C1CCCC2=CC(C(=O)N3CCC(CC3)C3=CC=C(C=C3)C(NCC3=CC4=NC=CN4C=C3)=O)=CN=C21 UELATMAAELOPAO-UHFFFAOYSA-N 0.000 description 1
- QRSGTRSXCPSDPN-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(5-methyl-2-prop-2-enylpyrazole-3-carbonyl)piperidin-4-yl]benzamide Chemical compound C=CCN1N=C(C)C=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 QRSGTRSXCPSDPN-UHFFFAOYSA-N 0.000 description 1
- IKBUMYHNBHKLEY-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(8-methylimidazo[1,2-a]pyridine-2-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CN2C=CC=C(C)C2=N1 IKBUMYHNBHKLEY-UHFFFAOYSA-N 0.000 description 1
- GJABYIIIBMAJHD-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinoline-4-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CC=C2C(C(=O)N3CCC(CC3)C3=CC=C(C=C3)C(NCC3=CC4=NC=CN4C=C3)=O)=CN=CC2=C1 GJABYIIIBMAJHD-UHFFFAOYSA-N 0.000 description 1
- IULBTOPDKZQROZ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinoline-7-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN=CC2=CC(C(=O)N3CCC(CC3)C3=CC=C(C=C3)C(NCC3=CC4=NC=CN4C=C3)=O)=CC=C21 IULBTOPDKZQROZ-UHFFFAOYSA-N 0.000 description 1
- SOVXKPHSQHAVAF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinoline-8-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=NC=C2C(C(=O)N3CCC(CC3)C3=CC=C(C=C3)C(NCC3=CC4=NC=CN4C=C3)=O)=CC=CC2=C1 SOVXKPHSQHAVAF-UHFFFAOYSA-N 0.000 description 1
- QVZFTEQLDJBKSZ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(oxane-4-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1CCOCC1 QVZFTEQLDJBKSZ-UHFFFAOYSA-N 0.000 description 1
- GNRWRAIQURZKMU-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(oxane-4-carbonyl)piperidin-4-yl]oxybenzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1OC(CC1)CCN1C(=O)C1CCOCC1 GNRWRAIQURZKMU-UHFFFAOYSA-N 0.000 description 1
- RNBCCTJNGFGKOH-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(oxane-4-carbonyl)pyrrolidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C1CCOCC1 RNBCCTJNGFGKOH-UHFFFAOYSA-N 0.000 description 1
- CZUSNFIGQHPBIW-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(oxolane-3-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1CCOC1 CZUSNFIGQHPBIW-UHFFFAOYSA-N 0.000 description 1
- FTNIIAXUOUQDKS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(piperidine-1-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)N1CCCCC1 FTNIIAXUOUQDKS-UHFFFAOYSA-N 0.000 description 1
- DIKQEUPTMVDOCW-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazine-2-carbonyl)azetidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C1=CN=CC=N1 DIKQEUPTMVDOCW-UHFFFAOYSA-N 0.000 description 1
- WPWXIRNPJQNTNA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazine-2-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CN=CC=N1 WPWXIRNPJQNTNA-UHFFFAOYSA-N 0.000 description 1
- DJDUWAGBJSOZGF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazolo[1,5-a]pyridine-2-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=C2C=CC=CN2N=C1C(=O)N(CC1)CCC1C(C=C1)=CC=C1C(=O)NCC1=CC2=NC=CN2C=C1 DJDUWAGBJSOZGF-UHFFFAOYSA-N 0.000 description 1
- RWHPEZOGCGZKJP-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridine-2-carbonyl)azetidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C1=CC=CC=N1 RWHPEZOGCGZKJP-UHFFFAOYSA-N 0.000 description 1
- FTXCRUVJTSTUEV-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridine-2-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CC=N1 FTXCRUVJTSTUEV-UHFFFAOYSA-N 0.000 description 1
- IHXIUQRWJYNPQP-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridine-2-carbonyl)pyrrolidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C1=CC=CC=N1 IHXIUQRWJYNPQP-UHFFFAOYSA-N 0.000 description 1
- SHMHLWBJGQPGSI-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridine-3-carbonyl)azetidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C1=CC=CN=C1 SHMHLWBJGQPGSI-UHFFFAOYSA-N 0.000 description 1
- HQLFMTOVGKZSGZ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridine-3-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CN=C1 HQLFMTOVGKZSGZ-UHFFFAOYSA-N 0.000 description 1
- IAOLXVWLBARBFL-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridine-3-carbonyl)pyrrolidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C1=CC=CN=C1 IAOLXVWLBARBFL-UHFFFAOYSA-N 0.000 description 1
- ABIPREAOSNPBMU-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridine-4-carbonyl)azetidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C1=CC=NC=C1 ABIPREAOSNPBMU-UHFFFAOYSA-N 0.000 description 1
- GHSLBACXBGJEMY-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridine-4-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=NC=C1 GHSLBACXBGJEMY-UHFFFAOYSA-N 0.000 description 1
- YGSRMTWEWQODOX-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridine-4-carbonyl)pyrrolidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C1=CC=NC=C1 YGSRMTWEWQODOX-UHFFFAOYSA-N 0.000 description 1
- LOCUJNNMBHWBHM-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrimidine-4-carbonyl)azetidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C1=CC=NC=N1 LOCUJNNMBHWBHM-UHFFFAOYSA-N 0.000 description 1
- VZDWIITXDVJZTO-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrrolidine-1-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)N1CCCC1 VZDWIITXDVJZTO-UHFFFAOYSA-N 0.000 description 1
- KANPDUWRPVKICM-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinoline-7-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CC=NC2=CC(C(=O)N3CCC(CC3)C3=CC=C(C=C3)C(NCC3=CC4=NC=CN4C=C3)=O)=CC=C21 KANPDUWRPVKICM-UHFFFAOYSA-N 0.000 description 1
- UDFHPGIDIPIGMC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinoxaline-2-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CC=CC2=NC(C(=O)N3CCC(CC3)C3=CC=C(C=C3)C(NCC3=CC4=NC=CN4C=C3)=O)=CN=C21 UDFHPGIDIPIGMC-UHFFFAOYSA-N 0.000 description 1
- HRMYMPSKFKMLQL-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thieno[3,2-b]pyridine-2-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CC=C2SC(C(=O)N3CCC(CC3)C3=CC=C(C=C3)C(NCC3=CC4=NC=CN4C=C3)=O)=CC2=N1 HRMYMPSKFKMLQL-UHFFFAOYSA-N 0.000 description 1
- VSCYYSTUBYGQOL-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophene-2-carbonyl)azetidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C1=CC=CS1 VSCYYSTUBYGQOL-UHFFFAOYSA-N 0.000 description 1
- FTRAHVQSVCAOCS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophene-2-carbonyl)piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CS1 FTRAHVQSVCAOCS-UHFFFAOYSA-N 0.000 description 1
- XNAHMPSUMXYFFB-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophene-2-carbonyl)pyrrolidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C1=CC=CS1 XNAHMPSUMXYFFB-UHFFFAOYSA-N 0.000 description 1
- CBUDZGDKGFXYDO-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophene-3-carbonyl)azetidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CN1C(=O)C=1C=CSC=1 CBUDZGDKGFXYDO-UHFFFAOYSA-N 0.000 description 1
- LUSFGFYWWFPNDZ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophene-3-carbonyl)pyrrolidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)C=1C=CSC=1 LUSFGFYWWFPNDZ-UHFFFAOYSA-N 0.000 description 1
- CUQBFFRPLZNMOF-JOCHJYFZSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(2r)-oxolane-2-carbonyl]piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)[C@H]1CCCO1 CUQBFFRPLZNMOF-JOCHJYFZSA-N 0.000 description 1
- HICALKZVOBFVFU-JOCHJYFZSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(2r)-oxolane-2-carbonyl]piperidin-4-yl]oxybenzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1OC(CC1)CCN1C(=O)[C@H]1CCCO1 HICALKZVOBFVFU-JOCHJYFZSA-N 0.000 description 1
- ZMCKOSFRDYJIHT-BPGUCPLFSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(2r)-oxolane-2-carbonyl]pyrrolidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)[C@H]1CCCO1 ZMCKOSFRDYJIHT-BPGUCPLFSA-N 0.000 description 1
- DIMQTSBDLQTAKF-INIZCTEOSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(2s)-2-methylbutanoyl]azetidin-3-yl]benzamide Chemical compound C1N(C(=O)[C@@H](C)CC)CC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 DIMQTSBDLQTAKF-INIZCTEOSA-N 0.000 description 1
- OOFSFUJSCOBTMJ-INIZCTEOSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(2s)-2-methylbutanoyl]azetidin-3-yl]oxybenzamide Chemical compound C1N(C(=O)[C@@H](C)CC)CC1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 OOFSFUJSCOBTMJ-INIZCTEOSA-N 0.000 description 1
- AHCBZTHQDZCCLB-SFHVURJKSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(2s)-2-methylbutanoyl]piperidin-4-yl]benzamide Chemical compound C1CN(C(=O)[C@@H](C)CC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 AHCBZTHQDZCCLB-SFHVURJKSA-N 0.000 description 1
- DFAYLZZIKRBIQR-SFHVURJKSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(2s)-2-methylbutanoyl]piperidin-4-yl]oxybenzamide Chemical compound C1CN(C(=O)[C@@H](C)CC)CCC1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 DFAYLZZIKRBIQR-SFHVURJKSA-N 0.000 description 1
- VJPXGDRIFMDJDX-PBVYKCSPSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(2s)-2-methylbutanoyl]pyrrolidin-3-yl]benzamide Chemical compound C1N(C(=O)[C@@H](C)CC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 VJPXGDRIFMDJDX-PBVYKCSPSA-N 0.000 description 1
- CUQBFFRPLZNMOF-QFIPXVFZSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(2s)-oxolane-2-carbonyl]piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)[C@@H]1CCCO1 CUQBFFRPLZNMOF-QFIPXVFZSA-N 0.000 description 1
- HICALKZVOBFVFU-QFIPXVFZSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(2s)-oxolane-2-carbonyl]piperidin-4-yl]oxybenzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1OC(CC1)CCN1C(=O)[C@@H]1CCCO1 HICALKZVOBFVFU-QFIPXVFZSA-N 0.000 description 1
- ZMCKOSFRDYJIHT-LBAQZLPGSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(2s)-oxolane-2-carbonyl]pyrrolidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)[C@@H]1CCCO1 ZMCKOSFRDYJIHT-LBAQZLPGSA-N 0.000 description 1
- CZUSNFIGQHPBIW-JOCHJYFZSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(3r)-oxolane-3-carbonyl]piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)[C@@H]1CCOC1 CZUSNFIGQHPBIW-JOCHJYFZSA-N 0.000 description 1
- CZUSNFIGQHPBIW-QFIPXVFZSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(3s)-oxolane-3-carbonyl]piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)[C@H]1CCOC1 CZUSNFIGQHPBIW-QFIPXVFZSA-N 0.000 description 1
- HWMAGWMIEIRDLZ-LBAQZLPGSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(3s)-oxolane-3-carbonyl]pyrrolidin-3-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(C1)CCN1C(=O)[C@H]1CCOC1 HWMAGWMIEIRDLZ-LBAQZLPGSA-N 0.000 description 1
- NNWGEBIBPAELPQ-JFQJCAQQSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(e)-2-methylbut-2-enoyl]piperidin-4-yl]benzamide Chemical compound C1CN(C(=O)C(/C)=C/C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 NNWGEBIBPAELPQ-JFQJCAQQSA-N 0.000 description 1
- NESIHWDJVPCVRM-RMOCHZDMSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(e)-2-methylpent-2-enoyl]piperidin-4-yl]benzamide Chemical compound C1CN(C(=O)C(/C)=C/CC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 NESIHWDJVPCVRM-RMOCHZDMSA-N 0.000 description 1
- ZFQVJAULNUCEMQ-CMDGGOBGSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(e)-3-(2-methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl]benzamide Chemical compound COC1=NC=CC=C1\C=C\C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 ZFQVJAULNUCEMQ-CMDGGOBGSA-N 0.000 description 1
- RFMBALBTVDASKC-CMDGGOBGSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[(e)-3-pyridin-2-ylprop-2-enoyl]piperidin-4-yl]benzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1C(CC1)CCN1C(=O)\C=C\C1=CC=CC=N1 RFMBALBTVDASKC-CMDGGOBGSA-N 0.000 description 1
- QCVHUTCNKLWNOS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[2-(1-propan-2-ylpyrazol-3-yl)acetyl]piperidin-4-yl]benzamide Chemical compound CC(C)N1C=CC(CC(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=N1 QCVHUTCNKLWNOS-UHFFFAOYSA-N 0.000 description 1
- CHJJMCVEKGWZNV-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[2-(2-methoxy-5-methylphenyl)acetyl]piperidin-4-yl]benzamide Chemical compound COC1=CC=C(C)C=C1CC(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 CHJJMCVEKGWZNV-UHFFFAOYSA-N 0.000 description 1
- VPKPFJFXBYGDPA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[2-(2-methoxyphenyl)acetyl]piperidin-4-yl]benzamide Chemical compound COC1=CC=CC=C1CC(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 VPKPFJFXBYGDPA-UHFFFAOYSA-N 0.000 description 1
- GAPQGMUPWGMIEB-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[2-(2-methylpropylsulfonyl)acetyl]piperidin-4-yl]benzamide Chemical compound C1CN(C(=O)CS(=O)(=O)CC(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 GAPQGMUPWGMIEB-UHFFFAOYSA-N 0.000 description 1
- OYRKMLQLEDATJQ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[2-(3-methoxyphenyl)acetyl]piperidin-4-yl]benzamide Chemical compound COC1=CC=CC(CC(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 OYRKMLQLEDATJQ-UHFFFAOYSA-N 0.000 description 1
- DMMIPNMJUIIPKW-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[2-(oxan-4-yl)acetyl]azetidin-3-yl]benzamide Chemical compound C1C(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)CC1CCOCC1 DMMIPNMJUIIPKW-UHFFFAOYSA-N 0.000 description 1
- UIKFAUULMGXYLZ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[2-(oxan-4-yl)acetyl]piperidin-4-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)CC1CCOCC1 UIKFAUULMGXYLZ-UHFFFAOYSA-N 0.000 description 1
- ASCJYIQLHUEMSH-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[2-(oxan-4-yl)acetyl]piperidin-4-yl]oxybenzamide Chemical compound C1CC(OC=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)CC1CCOCC1 ASCJYIQLHUEMSH-UHFFFAOYSA-N 0.000 description 1
- RJVJHSZZZWCHIQ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[2-(oxan-4-yl)acetyl]pyrrolidin-3-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)CC1CCOCC1 RJVJHSZZZWCHIQ-UHFFFAOYSA-N 0.000 description 1
- RQNYCMNIDQQYSO-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[2-(oxolan-2-yl)acetyl]piperidin-4-yl]benzamide Chemical compound C1CC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)CC1CCCO1 RQNYCMNIDQQYSO-UHFFFAOYSA-N 0.000 description 1
- UUYYHBRHSHYZOF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[2-(trifluoromethoxy)benzoyl]piperidin-4-yl]benzamide Chemical compound FC(F)(F)OC1=CC=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 UUYYHBRHSHYZOF-UHFFFAOYSA-N 0.000 description 1
- DXMKSYWGLOCLCX-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[2-(trifluoromethyl)benzoyl]piperidin-4-yl]benzamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 DXMKSYWGLOCLCX-UHFFFAOYSA-N 0.000 description 1
- HREQMABOBVOHCB-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[2-(trifluoromethyl)furan-3-carbonyl]piperidin-4-yl]benzamide Chemical compound O1C=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1C(F)(F)F HREQMABOBVOHCB-UHFFFAOYSA-N 0.000 description 1
- SXZHBFUXJLIDRE-HFZDXXHNSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[2-[(1r,2s)-2-methylcyclohexyl]oxyacetyl]piperidin-4-yl]benzamide Chemical compound C[C@H]1CCCC[C@H]1OCC(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 SXZHBFUXJLIDRE-HFZDXXHNSA-N 0.000 description 1
- SNHIHKSEAPUBQL-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[3-(trifluoromethoxy)benzoyl]azetidin-3-yl]benzamide Chemical compound FC(F)(F)OC1=CC=CC(C(=O)N2CC(C2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 SNHIHKSEAPUBQL-UHFFFAOYSA-N 0.000 description 1
- VVHLXYFQDTUGBU-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[3-(trifluoromethoxy)benzoyl]piperidin-4-yl]benzamide Chemical compound FC(F)(F)OC1=CC=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 VVHLXYFQDTUGBU-UHFFFAOYSA-N 0.000 description 1
- ZPHNBITYBRFWCE-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[3-(trifluoromethoxy)benzoyl]pyrrolidin-3-yl]benzamide Chemical compound FC(F)(F)OC1=CC=CC(C(=O)N2CC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 ZPHNBITYBRFWCE-UHFFFAOYSA-N 0.000 description 1
- YYFUQFZNMZJAAP-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[3-(trifluoromethyl)benzoyl]azetidin-3-yl]benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)N2CC(C2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 YYFUQFZNMZJAAP-UHFFFAOYSA-N 0.000 description 1
- IWPKJQHFLKMDAI-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[3-(trifluoromethyl)benzoyl]piperidin-4-yl]benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)N2CCC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 IWPKJQHFLKMDAI-UHFFFAOYSA-N 0.000 description 1
- KUBVTUFYZZUAEY-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[3-(trifluoromethyl)benzoyl]pyrrolidin-3-yl]benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)N2CC(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 KUBVTUFYZZUAEY-UHFFFAOYSA-N 0.000 description 1
- NDTPUKAJUMFTIA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[4-(trifluoromethoxy)benzoyl]piperidin-4-yl]benzamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 NDTPUKAJUMFTIA-UHFFFAOYSA-N 0.000 description 1
- BWJPZYWHZXQUOJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[4-(trifluoromethyl)benzoyl]piperidin-4-yl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)N1CCC(C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 BWJPZYWHZXQUOJ-UHFFFAOYSA-N 0.000 description 1
- KJURXXBCTRZHNC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-[6-(trifluoromethyl)pyrimidin-4-yl]-3,6-dihydro-2h-pyridin-4-yl]benzamide Chemical compound C1=NC(C(F)(F)F)=CC(N2CC=C(CC2)C=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=N1 KJURXXBCTRZHNC-UHFFFAOYSA-N 0.000 description 1
- NQUBRTIAXXVLLH-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[2-(2-methylpropyl)pyrrolidine-1-carbonyl]benzamide Chemical compound CC(C)CC1CCCN1C(=O)C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 NQUBRTIAXXVLLH-UHFFFAOYSA-N 0.000 description 1
- BFTAGNLGQKPAIA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[3-(oxolan-2-yl)propanoylamino]benzamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=CC=1NC(=O)CCC1CCCO1 BFTAGNLGQKPAIA-UHFFFAOYSA-N 0.000 description 1
- NESJDYHLXDFHQK-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[[2-(2-methoxyphenyl)acetyl]amino]benzamide Chemical compound COC1=CC=CC=C1CC(=O)NC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 NESJDYHLXDFHQK-UHFFFAOYSA-N 0.000 description 1
- VQYQQMYSLYVKHL-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[[2-(oxan-4-yl)acetyl]amino]benzamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=CC=1NC(=O)CC1CCOCC1 VQYQQMYSLYVKHL-UHFFFAOYSA-N 0.000 description 1
- ZIZNMQJMNGUJSC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[[2-(oxolan-2-yl)acetyl]amino]benzamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=CC=1NC(=O)CC1CCCO1 ZIZNMQJMNGUJSC-UHFFFAOYSA-N 0.000 description 1
- OEEIZKJPYAVRQB-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[[2-(oxolan-3-yl)acetyl]amino]benzamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=CC=1NC(=O)CC1CCOC1 OEEIZKJPYAVRQB-UHFFFAOYSA-N 0.000 description 1
- DWBIKZFOTXKMPH-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-phenoxybenzamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 DWBIKZFOTXKMPH-UHFFFAOYSA-N 0.000 description 1
- BXKUCODTGKXPIJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methylpyrazol-4-yl)thiophene-2-carboxamide Chemical compound C1=NN(C)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 BXKUCODTGKXPIJ-UHFFFAOYSA-N 0.000 description 1
- INHJAHXWEMJDAW-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)thiophene-2-carboxamide Chemical compound C1N(S(=O)(=O)C)CCC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 INHJAHXWEMJDAW-UHFFFAOYSA-N 0.000 description 1
- YOTUSKNVBVNBNT-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methylsulfonylpiperidin-4-yl)thiophene-2-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 YOTUSKNVBVNBNT-UHFFFAOYSA-N 0.000 description 1
- ASJCDTKAHMVMTJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-propanoylpyrrolidin-3-yl)thiophene-2-carboxamide Chemical compound C1N(C(=O)CC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 ASJCDTKAHMVMTJ-UHFFFAOYSA-N 0.000 description 1
- AGNHDYAFCPYGNY-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-propylpyrazol-4-yl)thiophene-2-carboxamide Chemical compound C1=NN(CCC)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 AGNHDYAFCPYGNY-UHFFFAOYSA-N 0.000 description 1
- FFECXUHCRBINAK-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(2-methylpyrazol-3-yl)thiophene-2-carboxamide Chemical compound CN1N=CC=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 FFECXUHCRBINAK-UHFFFAOYSA-N 0.000 description 1
- BXAORNFXEKZRKK-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(3-propan-2-yloxyphenyl)thiophene-2-carboxamide Chemical compound CC(C)OC1=CC=CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 BXAORNFXEKZRKK-UHFFFAOYSA-N 0.000 description 1
- LWWQOQWSKFBRCM-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(6-morpholin-4-ylpyridin-3-yl)thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(C=N1)=CC=C1N1CCOCC1 LWWQOQWSKFBRCM-UHFFFAOYSA-N 0.000 description 1
- GJWLKJIBXOBFMD-MUMRKEEXSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[(1r)-3-methyl-1-[[2-(oxolan-3-yl)acetyl]amino]butyl]thiophene-2-carboxamide Chemical compound N([C@H](CC(C)C)C=1SC(=CC=1)C(=O)NCC1=CC2=NC=CN2C=C1)C(=O)CC1CCOC1 GJWLKJIBXOBFMD-MUMRKEEXSA-N 0.000 description 1
- SINMHEHJFDAITK-OAHLLOKOSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[(2r)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thiophene-2-carboxamide Chemical compound COC[C@H]1CCCN1C(=O)C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 SINMHEHJFDAITK-OAHLLOKOSA-N 0.000 description 1
- BGFALTMZGBUFSA-AWEZNQCLSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[(4r)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]thiophene-2-carboxamide Chemical compound CC(C)[C@@H]1COC(=O)N1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 BGFALTMZGBUFSA-AWEZNQCLSA-N 0.000 description 1
- VOYVGLVHGJCROQ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(1,2-oxazole-5-carbonyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(CC1)CCN1C(=O)C1=CC=NO1 VOYVGLVHGJCROQ-UHFFFAOYSA-N 0.000 description 1
- CFSONYDHGNMVIA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(1-methylcyclopropanecarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)C1(C)CC1 CFSONYDHGNMVIA-UHFFFAOYSA-N 0.000 description 1
- ANXTXIVZHGUBPT-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(1-methylpyrazole-4-carbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1=NN(C)C=C1C(=O)N1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 ANXTXIVZHGUBPT-UHFFFAOYSA-N 0.000 description 1
- NNPUGGVQOOMOAG-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(1-methylpyrrole-2-carbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound CN1C=CC=C1C(=O)N1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 NNPUGGVQOOMOAG-UHFFFAOYSA-N 0.000 description 1
- WPLGBQWVYJXWIO-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2,2,2-trifluoroethyl)pyrazol-4-yl]furan-2-carboxamide Chemical compound C1=NN(CC(F)(F)F)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)O1 WPLGBQWVYJXWIO-UHFFFAOYSA-N 0.000 description 1
- ALWLYAKLAUMSKK-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methoxyacetyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1CN(C(=O)COC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 ALWLYAKLAUMSKK-UHFFFAOYSA-N 0.000 description 1
- AMRZGYHMOJJKMY-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound COC1=CC=CC=C1C(=O)N1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 AMRZGYHMOJJKMY-UHFFFAOYSA-N 0.000 description 1
- KOKUXXZONIVMGU-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methoxyethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=NN(CCOC)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 KOKUXXZONIVMGU-UHFFFAOYSA-N 0.000 description 1
- KIJPTRISNWEGOJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methyl-2-piperazin-1-ylpropanoyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)C(C)(C)N1CCNCC1 KIJPTRISNWEGOJ-UHFFFAOYSA-N 0.000 description 1
- DKHRWWYICIWCCL-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound CC1=CC=CC=C1C(=O)N1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 DKHRWWYICIWCCL-UHFFFAOYSA-N 0.000 description 1
- VQZIJUMVVLYNSO-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)-3,6-dihydro-2h-pyridin-4-yl]furan-2-carboxamide Chemical compound C1N(C(=O)C(C)C)CCC(C=2OC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 VQZIJUMVVLYNSO-UHFFFAOYSA-N 0.000 description 1
- AQMFDRGILQECBF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]furan-2-carboxamide Chemical compound C1CN(C(=O)C(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)O1 AQMFDRGILQECBF-UHFFFAOYSA-N 0.000 description 1
- IMGIDPLCWCVHAZ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1CN(C(=O)C(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 IMGIDPLCWCVHAZ-UHFFFAOYSA-N 0.000 description 1
- LNAHRBLLGLJGHX-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1N(C(=O)C(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 LNAHRBLLGLJGHX-UHFFFAOYSA-N 0.000 description 1
- FBOXRYKTVNPPOP-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoylamino)cyclobutyl]thiophene-2-carboxamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)SC=1C1(NC(=O)C(C)C)CCC1 FBOXRYKTVNPPOP-UHFFFAOYSA-N 0.000 description 1
- GZWHGLWVGRLDST-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)pyrazol-4-yl]furan-2-carboxamide Chemical compound C1=NN(CC(C)C)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)O1 GZWHGLWVGRLDST-UHFFFAOYSA-N 0.000 description 1
- MAVIUJGEXDYOED-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=NN(CC(C)C)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 MAVIUJGEXDYOED-UHFFFAOYSA-N 0.000 description 1
- BIWJZCDYQFYTEY-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropylsulfonyl)-3,6-dihydro-2h-pyridin-4-yl]furan-2-carboxamide Chemical compound C1N(S(=O)(=O)CC(C)C)CCC(C=2OC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 BIWJZCDYQFYTEY-UHFFFAOYSA-N 0.000 description 1
- OPLQQHLGNJRRPO-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropylsulfonyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1CN(S(=O)(=O)CC(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 OPLQQHLGNJRRPO-UHFFFAOYSA-N 0.000 description 1
- VSXGERIEVRNCRQ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpyrazole-3-carbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound CN1N=CC=C1C(=O)N1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 VSXGERIEVRNCRQ-UHFFFAOYSA-N 0.000 description 1
- LBIDNLBKFLYNKS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylsulfonylethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=NN(CCS(=O)(=O)C)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 LBIDNLBKFLYNKS-UHFFFAOYSA-N 0.000 description 1
- QWUJJHHGEIYRLB-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CCN1CCOCC1 QWUJJHHGEIYRLB-UHFFFAOYSA-N 0.000 description 1
- HGXSPVDHHOUTCP-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-piperazin-1-ylethyl)pyrazol-4-yl]furan-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(O1)=CC=C1C(=C1)C=NN1CCN1CCNCC1 HGXSPVDHHOUTCP-UHFFFAOYSA-N 0.000 description 1
- GEFKIYAAKOSMFN-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-piperazin-1-ylethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CCN1CCNCC1 GEFKIYAAKOSMFN-UHFFFAOYSA-N 0.000 description 1
- YHMKELZHCSIMAC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1CN(C(=O)CC(F)(F)F)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 YHMKELZHCSIMAC-UHFFFAOYSA-N 0.000 description 1
- CWMNCBHWBYGIFP-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1N(C(=O)CC(F)(F)F)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 CWMNCBHWBYGIFP-UHFFFAOYSA-N 0.000 description 1
- XCHJVEVMWNLGAU-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoylamino)cyclobutyl]thiophene-2-carboxamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)SC=1C1(NC(=O)CC(F)(F)F)CCC1 XCHJVEVMWNLGAU-UHFFFAOYSA-N 0.000 description 1
- MNNSSEBIEQSJJE-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound COC1=CC=CC(C(=O)N2CC(CC2)C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 MNNSSEBIEQSJJE-UHFFFAOYSA-N 0.000 description 1
- ABOKSORUJDXHAS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)-3,6-dihydro-2h-pyridin-4-yl]furan-2-carboxamide Chemical compound C1N(C(=O)CC(C)C)CCC(C=2OC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 ABOKSORUJDXHAS-UHFFFAOYSA-N 0.000 description 1
- JAKUJJPNFMKLAU-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1CN(C(=O)CC(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 JAKUJJPNFMKLAU-UHFFFAOYSA-N 0.000 description 1
- AEWIRXOLKMJCCA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1N(C(=O)CC(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 AEWIRXOLKMJCCA-UHFFFAOYSA-N 0.000 description 1
- BKQCCJNAEWPVME-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoylamino)cyclobutyl]thiophene-2-carboxamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)SC=1C1(NC(=O)CC(C)C)CCC1 BKQCCJNAEWPVME-UHFFFAOYSA-N 0.000 description 1
- HGZFKTYOFKMKMP-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methyloxetane-3-carbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CN1C(=O)C1(C)COC1 HGZFKTYOFKMKMP-UHFFFAOYSA-N 0.000 description 1
- AICSAZWATUKBKS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylthiophene-2-carbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1=CSC(C(=O)N2CC(CC2)C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1C AICSAZWATUKBKS-UHFFFAOYSA-N 0.000 description 1
- ZNSCDKYSMOTZCP-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1CN(C(=O)CCC(F)(F)F)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 ZNSCDKYSMOTZCP-UHFFFAOYSA-N 0.000 description 1
- RQOPPQXLMJNHSR-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1N(C(=O)CCC(F)(F)F)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 RQOPPQXLMJNHSR-UHFFFAOYSA-N 0.000 description 1
- BUHUSSWJMFFHOE-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C(=O)N1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 BUHUSSWJMFFHOE-UHFFFAOYSA-N 0.000 description 1
- HPKHSBYAVDOTMH-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1=CC(C)=CC=C1C(=O)N1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CC1 HPKHSBYAVDOTMH-UHFFFAOYSA-N 0.000 description 1
- YGGCUOHNFYVZAK-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(oxan-2-ylmethyl)pyrazol-4-yl]furan-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(O1)=CC=C1C(=C1)C=NN1CC1CCCCO1 YGGCUOHNFYVZAK-UHFFFAOYSA-N 0.000 description 1
- JJGGSQPINFFKJW-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(oxan-2-ylmethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1CCCCO1 JJGGSQPINFFKJW-UHFFFAOYSA-N 0.000 description 1
- SXWFAKZKWICWJD-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(oxan-3-ylmethyl)pyrazol-4-yl]furan-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(O1)=CC=C1C(=C1)C=NN1CC1CCCOC1 SXWFAKZKWICWJD-UHFFFAOYSA-N 0.000 description 1
- LXISSHQIDYLPHX-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(oxan-3-ylmethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1CCCOC1 LXISSHQIDYLPHX-UHFFFAOYSA-N 0.000 description 1
- MQJMDITVMGEWIS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(oxan-4-yl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1C1CCOCC1 MQJMDITVMGEWIS-UHFFFAOYSA-N 0.000 description 1
- RXKBEZWAQSFQLP-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(oxan-4-ylmethyl)pyrazol-4-yl]furan-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(O1)=CC=C1C(=C1)C=NN1CC1CCOCC1 RXKBEZWAQSFQLP-UHFFFAOYSA-N 0.000 description 1
- SDORIEMQDXGBSA-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(oxan-4-ylmethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1CCOCC1 SDORIEMQDXGBSA-UHFFFAOYSA-N 0.000 description 1
- LYGHUHATAHYBIJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(oxolan-2-ylmethyl)pyrazol-4-yl]furan-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(O1)=CC=C1C(=C1)C=NN1CC1CCCO1 LYGHUHATAHYBIJ-UHFFFAOYSA-N 0.000 description 1
- YKQMGNDUJLWTBH-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(oxolan-2-ylmethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1CCCO1 YKQMGNDUJLWTBH-UHFFFAOYSA-N 0.000 description 1
- HEUXHHWHWMCWLY-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(oxolan-3-ylmethyl)pyrazol-4-yl]furan-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(O1)=CC=C1C(=C1)C=NN1CC1CCOC1 HEUXHHWHWMCWLY-UHFFFAOYSA-N 0.000 description 1
- UXYWFFZUSQBYFJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(oxolan-3-ylmethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1CCOC1 UXYWFFZUSQBYFJ-UHFFFAOYSA-N 0.000 description 1
- FBMNPCMZFHMNFP-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(oxolane-3-carbonyl)piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(CC1)CCN1C(=O)C1CCOC1 FBMNPCMZFHMNFP-UHFFFAOYSA-N 0.000 description 1
- JPPPELVQQQTFJT-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(piperidin-4-ylmethyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1CC1CCNCC1 JPPPELVQQQTFJT-UHFFFAOYSA-N 0.000 description 1
- BGVRCYBHQKBHTI-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyrazine-2-carbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(C1)CCN1C(=O)C1=CN=CC=N1 BGVRCYBHQKBHTI-UHFFFAOYSA-N 0.000 description 1
- PRQULRBQRQWYTJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridine-2-carbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(C1)CCN1C(=O)C1=CC=CC=N1 PRQULRBQRQWYTJ-UHFFFAOYSA-N 0.000 description 1
- UBVNJOGCWYNTIP-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridine-3-carbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(C1)CCN1C(=O)C1=CC=CN=C1 UBVNJOGCWYNTIP-UHFFFAOYSA-N 0.000 description 1
- JINZOMTVEVGFCN-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridine-4-carbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(C1)CCN1C(=O)C1=CC=NC=C1 JINZOMTVEVGFCN-UHFFFAOYSA-N 0.000 description 1
- KCTADHIUGVUWET-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(thiophene-2-carbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(C1)CCN1C(=O)C1=CC=CS1 KCTADHIUGVUWET-UHFFFAOYSA-N 0.000 description 1
- MUYORJUGRGJOMB-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[(1-methoxy-3,3-dimethylcyclohexyl)methyl]-5-methylpyrazol-4-yl]thiophene-2-carboxamide Chemical compound N1=CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C(C)N1CC1(OC)CCCC(C)(C)C1 MUYORJUGRGJOMB-UHFFFAOYSA-N 0.000 description 1
- ONCDTXADGHDRDW-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[(2-methyloxan-2-yl)methyl]pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=C(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C=NN1CC1(C)CCCCO1 ONCDTXADGHDRDW-UHFFFAOYSA-N 0.000 description 1
- PNFZXJIXIOHJQP-INIZCTEOSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[(2s)-2-methylbutanoyl]-3,6-dihydro-2h-pyridin-4-yl]furan-2-carboxamide Chemical compound C1N(C(=O)[C@@H](C)CC)CCC(C=2OC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 PNFZXJIXIOHJQP-INIZCTEOSA-N 0.000 description 1
- BSCYFBFOYBQYSV-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[(3-methyloxetan-3-yl)methyl]pyrazol-4-yl]furan-2-carboxamide Chemical compound C1=C(C=2OC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C=NN1CC1(C)COC1 BSCYFBFOYBQYSV-UHFFFAOYSA-N 0.000 description 1
- NCIGEYKRLJGIGK-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[(3-methyloxetan-3-yl)methyl]pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=C(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C=NN1CC1(C)COC1 NCIGEYKRLJGIGK-UHFFFAOYSA-N 0.000 description 1
- FZNHYGAXAXGWTI-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[(4-methyloxan-4-yl)methyl]pyrazol-4-yl]furan-2-carboxamide Chemical compound C1=C(C=2OC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C=NN1CC1(C)CCOCC1 FZNHYGAXAXGWTI-UHFFFAOYSA-N 0.000 description 1
- QAOVBOOZUWAONS-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[(4-methyloxan-4-yl)methyl]pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=C(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C=NN1CC1(C)CCOCC1 QAOVBOOZUWAONS-UHFFFAOYSA-N 0.000 description 1
- HDTNODJYVOMWJF-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[(4-methylpiperidin-4-yl)methyl]pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=C(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)C=NN1CC1(C)CCNCC1 HDTNODJYVOMWJF-UHFFFAOYSA-N 0.000 description 1
- JDYIOPICTSCAJN-AYSLTRBKSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[(e)-2-methylpent-2-enoyl]pyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1N(C(=O)C(/C)=C/CC)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 JDYIOPICTSCAJN-AYSLTRBKSA-N 0.000 description 1
- PXJNJXVYNMBSHJ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[2-(oxan-4-yl)acetyl]piperidin-4-yl]thiophene-2-carboxamide Chemical compound C1CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCN1C(=O)CC1CCOCC1 PXJNJXVYNMBSHJ-UHFFFAOYSA-N 0.000 description 1
- LYGHUHATAHYBIJ-QGZVFWFLSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[[(2r)-oxolan-2-yl]methyl]pyrazol-4-yl]furan-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(O1)=CC=C1C(=C1)C=NN1C[C@H]1CCCO1 LYGHUHATAHYBIJ-QGZVFWFLSA-N 0.000 description 1
- YKQMGNDUJLWTBH-QGZVFWFLSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[[(2r)-oxolan-2-yl]methyl]pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1C[C@H]1CCCO1 YKQMGNDUJLWTBH-QGZVFWFLSA-N 0.000 description 1
- NEQXHCCOTRDSNI-HNNXBMFYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[[(2s)-2-methylbutanoyl]amino]cyclobutyl]thiophene-2-carboxamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)SC=1C1(NC(=O)[C@@H](C)CC)CCC1 NEQXHCCOTRDSNI-HNNXBMFYSA-N 0.000 description 1
- LYGHUHATAHYBIJ-KRWDZBQOSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[[(2s)-oxolan-2-yl]methyl]pyrazol-4-yl]furan-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(O1)=CC=C1C(=C1)C=NN1C[C@@H]1CCCO1 LYGHUHATAHYBIJ-KRWDZBQOSA-N 0.000 description 1
- YKQMGNDUJLWTBH-KRWDZBQOSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-[[(2s)-oxolan-2-yl]methyl]pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C(=C1)C=NN1C[C@@H]1CCCO1 YKQMGNDUJLWTBH-KRWDZBQOSA-N 0.000 description 1
- QYKLBDCVVSJVTR-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[2-(2-methylpropyl)pyrazol-3-yl]furan-2-carboxamide Chemical compound CC(C)CN1N=CC=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)O1 QYKLBDCVVSJVTR-UHFFFAOYSA-N 0.000 description 1
- KDXWUNBKGGMOSI-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[2-(2-methylpropyl)pyrazol-3-yl]thiophene-2-carboxamide Chemical compound CC(C)CN1N=CC=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 KDXWUNBKGGMOSI-UHFFFAOYSA-N 0.000 description 1
- XGHGBPOYFHSLEZ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[2-(2-methylpropyl)pyrrolidine-1-carbonyl]thiophene-2-carboxamide Chemical compound CC(C)CC1CCCN1C(=O)C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 XGHGBPOYFHSLEZ-UHFFFAOYSA-N 0.000 description 1
- QUQMDALSJHEHHV-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[2-(3-methylbutyl)pyrazol-3-yl]furan-2-carboxamide Chemical compound CC(C)CCN1N=CC=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)O1 QUQMDALSJHEHHV-UHFFFAOYSA-N 0.000 description 1
- CHHIUQRJHCQCSC-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[2-methyl-5-(2-methylpropyl)pyrazol-3-yl]thiophene-2-carboxamide Chemical compound CN1N=C(CC(C)C)C=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 CHHIUQRJHCQCSC-UHFFFAOYSA-N 0.000 description 1
- DXWBUDMGCBRUPZ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(2-methylpropanoylamino)oxetan-3-yl]thiophene-2-carboxamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)SC=1C1(NC(=O)C(C)C)COC1 DXWBUDMGCBRUPZ-UHFFFAOYSA-N 0.000 description 1
- KUWUWZRYQVKYGK-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(pentanoylamino)oxetan-3-yl]thiophene-2-carboxamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)SC=1C1(NC(=O)CCCC)COC1 KUWUWZRYQVKYGK-UHFFFAOYSA-N 0.000 description 1
- LKPRLWKVURJKRF-AWEZNQCLSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-[[(2s)-2-methylbutanoyl]amino]oxetan-3-yl]thiophene-2-carboxamide Chemical compound C=1C=C(C(=O)NCC2=CC3=NC=CN3C=C2)SC=1C1(NC(=O)[C@@H](C)CC)COC1 LKPRLWKVURJKRF-AWEZNQCLSA-N 0.000 description 1
- NXSVUJSCKFZJLX-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-[[2-(oxolan-3-yl)acetyl]amino]oxetan-3-yl]thiophene-2-carboxamide Chemical compound C1OCC1(C=1SC(=CC=1)C(=O)NCC1=CC2=NC=CN2C=C1)NC(=O)CC1CCOC1 NXSVUJSCKFZJLX-UHFFFAOYSA-N 0.000 description 1
- MSRMYMOADXKCSZ-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[4-(2-methylpropyl)phenyl]furan-2-carboxamide Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)O1 MSRMYMOADXKCSZ-UHFFFAOYSA-N 0.000 description 1
- SNMGFFOSMQPATB-UHFFFAOYSA-N n-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-phenylthiophene-2-carboxamide Chemical compound C1=CN2C=CN=C2C=C1CNC(=O)C(S1)=CC=C1C1=CC=CC=C1 SNMGFFOSMQPATB-UHFFFAOYSA-N 0.000 description 1
- GPAKKOPBVDPWTO-UHFFFAOYSA-N n-[(1,1-dioxothiolan-3-yl)methyl]-4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)benzamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(=O)NCC1CCS(=O)(=O)C1 GPAKKOPBVDPWTO-UHFFFAOYSA-N 0.000 description 1
- HCKFPINALODOAO-UHFFFAOYSA-N n-[(3-chloroimidazo[1,2-a]pyrazin-6-yl)methyl]-4-[(2-cyclopentylacetyl)amino]benzamide Chemical compound C=1N2C(Cl)=CN=C2C=NC=1CNC(=O)C(C=C1)=CC=C1NC(=O)CC1CCCC1 HCKFPINALODOAO-UHFFFAOYSA-N 0.000 description 1
- QSIUNEFEMIOOQE-UHFFFAOYSA-N n-[(3-chloroimidazo[1,2-a]pyridin-6-yl)methyl]-4-[[2-(oxolan-3-yl)acetyl]amino]benzamide Chemical compound C=1N2C(Cl)=CN=C2C=CC=1CNC(=O)C(C=C1)=CC=C1NC(=O)CC1CCOC1 QSIUNEFEMIOOQE-UHFFFAOYSA-N 0.000 description 1
- IPXIVQLVZDJPKR-UHFFFAOYSA-N n-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide Chemical compound C1CN(C(=O)C(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=C(Cl)N3C=C2)C=C1 IPXIVQLVZDJPKR-UHFFFAOYSA-N 0.000 description 1
- IBYBXELIPMZDQR-UHFFFAOYSA-N n-[(7-fluoroimidazo[1,2-a]pyridin-6-yl)methyl]-5-[1-(2-methylpropyl)pyrazol-4-yl]thiophene-2-carboxamide Chemical compound C1=NN(CC(C)C)C=C1C1=CC=C(C(=O)NCC=2C(=CC3=NC=CN3C=2)F)S1 IBYBXELIPMZDQR-UHFFFAOYSA-N 0.000 description 1
- MFCYZCOEVSVPQC-UHFFFAOYSA-N n-[1-[5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl]cyclobutyl]oxane-4-carboxamide Chemical compound C1COCCC1C(=O)NC1(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)CCC1 MFCYZCOEVSVPQC-UHFFFAOYSA-N 0.000 description 1
- GKDWNVLGYRLJDO-UHFFFAOYSA-N n-[2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)benzamide Chemical compound C1=CC(OC)=CC=C1C(CO)NC(=O)C(C=C1)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 GKDWNVLGYRLJDO-UHFFFAOYSA-N 0.000 description 1
- ZLOJEMAQTFONFC-UHFFFAOYSA-N n-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-2-imidazo[1,2-a]pyridin-7-ylacetamide Chemical compound C=1C=C(NC(=O)CC2=CC3=NC=CN3C=C2)C(F)=CC=1C(CC1)CCN1C(=O)C1=CC=CC=C1 ZLOJEMAQTFONFC-UHFFFAOYSA-N 0.000 description 1
- IMKULPLFDBNTBB-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]-1,1-dioxothiane-4-carboxamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1NC(=O)C1CCS(=O)(=O)CC1 IMKULPLFDBNTBB-UHFFFAOYSA-N 0.000 description 1
- CPHYNRNOLWJZAX-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]-1,4-dioxane-2-carboxamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1NC(=O)C1COCCO1 CPHYNRNOLWJZAX-UHFFFAOYSA-N 0.000 description 1
- MRGFSEGWPDTOFZ-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]-1-methylpiperidine-4-carboxamide Chemical compound C1CN(C)CCC1C(=O)NC(C=C1)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 MRGFSEGWPDTOFZ-UHFFFAOYSA-N 0.000 description 1
- OHLBFWUGYJOCAH-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]-2-(2-methoxyethoxy)acetamide Chemical compound C1=CC(NC(=O)COCCOC)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 OHLBFWUGYJOCAH-UHFFFAOYSA-N 0.000 description 1
- ZFOXAKZBEOKOFA-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]-2-(oxan-4-yl)acetamide Chemical compound C=1C=C(NC(=O)NC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CC1CCOCC1 ZFOXAKZBEOKOFA-UHFFFAOYSA-N 0.000 description 1
- XDKNIUUIHBKQOK-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]-2-(oxolan-3-yl)acetamide Chemical compound C=1C=C(NC(=O)NC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CC1CCOC1 XDKNIUUIHBKQOK-UHFFFAOYSA-N 0.000 description 1
- MOCRZZANEDGDMS-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]-2-morpholin-4-ylacetamide Chemical compound C=1C=C(NC(=O)NC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CN1CCOCC1 MOCRZZANEDGDMS-UHFFFAOYSA-N 0.000 description 1
- RDGUNQWLGUNWSI-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]-3-methoxy-2-methylpropanamide Chemical compound C1=CC(NC(=O)C(C)COC)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 RDGUNQWLGUNWSI-UHFFFAOYSA-N 0.000 description 1
- ZNARNNOGHKGBSW-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]-4-methylpentanamide Chemical compound C1=CC(NC(=O)CCC(C)C)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 ZNARNNOGHKGBSW-UHFFFAOYSA-N 0.000 description 1
- LNTBEACWPYBUAX-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 LNTBEACWPYBUAX-UHFFFAOYSA-N 0.000 description 1
- AJSUGNQESYBEMI-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]butanamide Chemical compound C1=CC(NC(=O)CCC)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 AJSUGNQESYBEMI-UHFFFAOYSA-N 0.000 description 1
- GVIOIGBLMONSAY-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]oxane-4-carboxamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1NC(=O)C1CCOCC1 GVIOIGBLMONSAY-UHFFFAOYSA-N 0.000 description 1
- YYBISABQQQSNOH-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoylamino)phenyl]-2-(oxan-4-yl)acetamide Chemical compound C=1C=C(NC(=O)NCC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CC1CCOCC1 YYBISABQQQSNOH-UHFFFAOYSA-N 0.000 description 1
- VSOCYXAPBKOWBE-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoylamino)phenyl]-2-(oxolan-2-yl)acetamide Chemical compound C=1C=C(NC(=O)NCC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CC1CCCO1 VSOCYXAPBKOWBE-UHFFFAOYSA-N 0.000 description 1
- PYWRSROLPMCUAP-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoylamino)phenyl]-2-propan-2-yloxyacetamide Chemical compound C1=CC(NC(=O)COC(C)C)=CC=C1NC(=O)NCC1=CN2C=CN=C2C=C1 PYWRSROLPMCUAP-UHFFFAOYSA-N 0.000 description 1
- HFXLCOLEFFUECM-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoylamino)phenyl]-3-phenylpropanamide Chemical compound C=1C=C(NC(=O)NCC2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CCC1=CC=CC=C1 HFXLCOLEFFUECM-UHFFFAOYSA-N 0.000 description 1
- OINGQWFKETUJCG-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoylamino)phenyl]-4-methylpentanamide Chemical compound C1=CC(NC(=O)CCC(C)C)=CC=C1NC(=O)NCC1=CN2C=CN=C2C=C1 OINGQWFKETUJCG-UHFFFAOYSA-N 0.000 description 1
- KPIPTTNJNQQVOK-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenyl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 KPIPTTNJNQQVOK-UHFFFAOYSA-N 0.000 description 1
- FUKNTCYTRWOJIG-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 FUKNTCYTRWOJIG-UHFFFAOYSA-N 0.000 description 1
- QZNFHGFHTLKSRE-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoylamino)phenyl]-2-(oxan-4-yl)acetamide Chemical compound C=1C=C(NC(=O)NCC2=CC3=NC=CN3C=C2)C=CC=1NC(=O)CC1CCOCC1 QZNFHGFHTLKSRE-UHFFFAOYSA-N 0.000 description 1
- RXHXHIANWMVWHR-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoylamino)phenyl]-2-(oxolan-2-yl)acetamide Chemical compound C=1C=C(NC(=O)NCC2=CC3=NC=CN3C=C2)C=CC=1NC(=O)CC1CCCO1 RXHXHIANWMVWHR-UHFFFAOYSA-N 0.000 description 1
- MWRYDGKNXZOSPO-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoylamino)phenyl]-2-propan-2-yloxyacetamide Chemical compound C1=CC(NC(=O)COC(C)C)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 MWRYDGKNXZOSPO-UHFFFAOYSA-N 0.000 description 1
- OXBVUJDRBRQYKR-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoylamino)phenyl]-3-phenylpropanamide Chemical compound C=1C=C(NC(=O)NCC2=CC3=NC=CN3C=C2)C=CC=1NC(=O)CCC1=CC=CC=C1 OXBVUJDRBRQYKR-UHFFFAOYSA-N 0.000 description 1
- UVJCMJULVBRBMU-UHFFFAOYSA-N n-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoylamino)phenyl]-4-methylpentanamide Chemical compound C1=CC(NC(=O)CCC(C)C)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 UVJCMJULVBRBMU-UHFFFAOYSA-N 0.000 description 1
- NUHMDOUDZQBLNS-UHFFFAOYSA-N n-[4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl]-2-imidazo[1,2-a]pyridin-6-ylacetamide Chemical compound FC1=CC(F)=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)CC3=CN4C=CN=C4C=C3)=CC=2)CC1 NUHMDOUDZQBLNS-UHFFFAOYSA-N 0.000 description 1
- INPCBVPNMWVBBK-UHFFFAOYSA-N n-[4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl]-2-imidazo[1,2-a]pyridin-7-ylacetamide Chemical compound FC1=CC(F)=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)CC3=CC4=NC=CN4C=C3)=CC=2)CC1 INPCBVPNMWVBBK-UHFFFAOYSA-N 0.000 description 1
- PADJWXYTCWMNCV-UHFFFAOYSA-N n-[4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl]-2-imidazo[1,2-a]pyridin-6-ylacetamide Chemical compound FC1=CC=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)CC3=CN4C=CN=C4C=C3)=CC=2)CC1 PADJWXYTCWMNCV-UHFFFAOYSA-N 0.000 description 1
- WSWFNSJXKABCQV-UHFFFAOYSA-N n-[4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl]-2-imidazo[1,2-a]pyridin-7-ylacetamide Chemical compound FC1=CC=CC=C1C(=O)N1CCC(C=2C=CC(NC(=O)CC3=CC4=NC=CN4C=C3)=CC=2)CC1 WSWFNSJXKABCQV-UHFFFAOYSA-N 0.000 description 1
- JLGQXYDIZWRHSX-UHFFFAOYSA-N n-[4-[5-(2,2-dimethylpropyl)-1,3,4-oxadiazol-2-yl]phenyl]-2-imidazo[1,2-a]pyridin-7-ylacetamide Chemical compound O1C(CC(C)(C)C)=NN=C1C(C=C1)=CC=C1NC(=O)CC1=CC2=NC=CN2C=C1 JLGQXYDIZWRHSX-UHFFFAOYSA-N 0.000 description 1
- IZQCCOZOXCEWOC-UHFFFAOYSA-N n-[[4-[(2-cyclopentylacetyl)amino]phenyl]methyl]imidazo[1,2-a]pyridine-6-carboxamide Chemical compound C=1C=C(CNC(=O)C2=CN3C=CN=C3C=C2)C=CC=1NC(=O)CC1CCCC1 IZQCCOZOXCEWOC-UHFFFAOYSA-N 0.000 description 1
- POFVWRVNTLTQSV-UHFFFAOYSA-N n-benzyl-4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)benzamide Chemical compound C1=CC2=NC=CN2C=C1NC(=O)NC(C=C1)=CC=C1C(=O)NCC1=CC=CC=C1 POFVWRVNTLTQSV-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000005880 oxathiolanyl group Chemical group 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000003585 oxepinyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000005731 poly ADP ribosylation Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- HVFJLJZUFLIULG-UHFFFAOYSA-N propan-2-yl 4-[5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 HVFJLJZUFLIULG-UHFFFAOYSA-N 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LLEIKUGOSHBOFI-HXUWFJFHSA-N tert-butyl (3R)-3-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenoxy]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@H]1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 LLEIKUGOSHBOFI-HXUWFJFHSA-N 0.000 description 1
- BJTWGYKRQOLTDX-HXUWFJFHSA-N tert-butyl (3R)-3-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoylamino)phenoxy]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@H]1OC(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 BJTWGYKRQOLTDX-HXUWFJFHSA-N 0.000 description 1
- IGDJBUCFPCODGB-UHFFFAOYSA-N tert-butyl 3-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenoxy]azetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 IGDJBUCFPCODGB-UHFFFAOYSA-N 0.000 description 1
- JJVVIKXMODUKGQ-UHFFFAOYSA-N tert-butyl 3-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenyl]azetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 JJVVIKXMODUKGQ-UHFFFAOYSA-N 0.000 description 1
- CLVDVHABSCQPTN-UHFFFAOYSA-N tert-butyl 3-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenyl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 CLVDVHABSCQPTN-UHFFFAOYSA-N 0.000 description 1
- HNVXQBOVSYTJPE-UHFFFAOYSA-N tert-butyl 3-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoylamino)phenyl]azetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 HNVXQBOVSYTJPE-UHFFFAOYSA-N 0.000 description 1
- XHVGHTRMCGUJHJ-UHFFFAOYSA-N tert-butyl 3-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoylamino)phenyl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 XHVGHTRMCGUJHJ-UHFFFAOYSA-N 0.000 description 1
- MAUJLJVGWXVDEJ-UHFFFAOYSA-N tert-butyl 4-[2-[4-[5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl]pyrazol-1-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CCN1N=CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 MAUJLJVGWXVDEJ-UHFFFAOYSA-N 0.000 description 1
- CMEAKAXTOYNYIT-UHFFFAOYSA-N tert-butyl 4-[3-fluoro-4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoylamino)phenyl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=C(F)C(NC(=O)NCC3=CC4=NC=CN4C=C3)=CC=2)=C1 CMEAKAXTOYNYIT-UHFFFAOYSA-N 0.000 description 1
- YGGAJPLWFYVNOQ-UHFFFAOYSA-N tert-butyl 4-[3-fluoro-4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoylamino)phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C(C=C1F)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 YGGAJPLWFYVNOQ-UHFFFAOYSA-N 0.000 description 1
- XZPZBBSJMCRONL-UHFFFAOYSA-N tert-butyl 4-[3-fluoro-4-[(2-imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C(C=C1F)=CC=C1NC(=O)CC1=CC2=NC=CN2C=C1 XZPZBBSJMCRONL-UHFFFAOYSA-N 0.000 description 1
- MZYRQEHZJILEGF-UHFFFAOYSA-N tert-butyl 4-[4-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethylcarbamoyl)phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=NN3C=C2)C=C1 MZYRQEHZJILEGF-UHFFFAOYSA-N 0.000 description 1
- FSJCQTUTDFQUMM-UHFFFAOYSA-N tert-butyl 4-[4-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethylcarbamoylamino)phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=NN2C=C1 FSJCQTUTDFQUMM-UHFFFAOYSA-N 0.000 description 1
- VMOKMFQYCJKWGX-UHFFFAOYSA-N tert-butyl 4-[4-(imidazo[1,2-a]pyrazin-6-ylmethylcarbamoyl)phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(C(=O)NCC=2N=CC3=NC=CN3C=2)C=C1 VMOKMFQYCJKWGX-UHFFFAOYSA-N 0.000 description 1
- QJBMKTBDCJTSEF-UHFFFAOYSA-N tert-butyl 4-[4-(imidazo[1,2-a]pyrazin-6-ylmethylcarbamoylamino)phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1NC(=O)NCC(N=C1)=CN2C1=NC=C2 QJBMKTBDCJTSEF-UHFFFAOYSA-N 0.000 description 1
- JRBBZTATYOJCPR-UHFFFAOYSA-N tert-butyl 4-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoyl)phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(C(=O)NC2=CN3C=CN=C3C=C2)C=C1 JRBBZTATYOJCPR-UHFFFAOYSA-N 0.000 description 1
- UWSVDQYBPXLLCR-UHFFFAOYSA-N tert-butyl 4-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)butyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCCCNC(=O)NC1=CN2C=CN=C2C=C1 UWSVDQYBPXLLCR-UHFFFAOYSA-N 0.000 description 1
- QMQAKVGZARWWSM-UHFFFAOYSA-N tert-butyl 4-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=CC(NC(=O)NC3=CN4C=CN=C4C=C3)=CC=2)=C1 QMQAKVGZARWWSM-UHFFFAOYSA-N 0.000 description 1
- UAPHJZCEYLFUNF-UHFFFAOYSA-N tert-butyl 4-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoylamino)phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1NC(=O)NC1=CN2C=CN=C2C=C1 UAPHJZCEYLFUNF-UHFFFAOYSA-N 0.000 description 1
- XOYDONRTQQCMBR-UHFFFAOYSA-N tert-butyl 4-[4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)phenoxy]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=C(C(=O)NCC2=CN3C=CN=C3C=C2)C=C1 XOYDONRTQQCMBR-UHFFFAOYSA-N 0.000 description 1
- MSECYIPRRQVIBX-UHFFFAOYSA-N tert-butyl 4-[4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)phenyl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=CC(=CC=2)C(=O)NCC2=CN3C=CN=C3C=C2)=C1 MSECYIPRRQVIBX-UHFFFAOYSA-N 0.000 description 1
- YLLYYRKNKHRICA-UHFFFAOYSA-N tert-butyl 4-[4-(imidazo[1,2-a]pyridin-7-ylcarbamoyl)phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(C(=O)NC2=CC3=NC=CN3C=C2)C=C1 YLLYYRKNKHRICA-UHFFFAOYSA-N 0.000 description 1
- HKLVFFBIEWTTEE-UHFFFAOYSA-N tert-butyl 4-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenoxy]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 HKLVFFBIEWTTEE-UHFFFAOYSA-N 0.000 description 1
- DWLNLSHYFRKLBB-UHFFFAOYSA-N tert-butyl 4-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)C=C1 DWLNLSHYFRKLBB-UHFFFAOYSA-N 0.000 description 1
- VGSDGCVTNKHSPX-UHFFFAOYSA-N tert-butyl 4-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoylamino)phenoxy]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 VGSDGCVTNKHSPX-UHFFFAOYSA-N 0.000 description 1
- IRRIOZMFFHPOEA-UHFFFAOYSA-N tert-butyl 4-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoylamino)phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1NC(=O)NCC1=CC2=NC=CN2C=C1 IRRIOZMFFHPOEA-UHFFFAOYSA-N 0.000 description 1
- CLJXIFLCXVKYIU-UHFFFAOYSA-N tert-butyl 4-[4-(imidazo[1,2-b]pyridazin-6-ylmethylcarbamoyl)phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(C(=O)NCC2=NN3C=CN=C3C=C2)C=C1 CLJXIFLCXVKYIU-UHFFFAOYSA-N 0.000 description 1
- VRTDJKMILCASAF-UHFFFAOYSA-N tert-butyl 4-[4-[(2-imidazo[1,2-a]pyridin-6-ylacetyl)amino]phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1NC(=O)CC1=CN2C=CN=C2C=C1 VRTDJKMILCASAF-UHFFFAOYSA-N 0.000 description 1
- VCQDEPHTDVVRAM-UHFFFAOYSA-N tert-butyl 4-[4-[(2-imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1NC(=O)CC1=CC2=NC=CN2C=C1 VCQDEPHTDVVRAM-UHFFFAOYSA-N 0.000 description 1
- KBZISYOJTNBQLD-UHFFFAOYSA-N tert-butyl 4-[4-[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoyl]phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(C(=O)NC2=CN3C(Cl)=CN=C3C=C2)C=C1 KBZISYOJTNBQLD-UHFFFAOYSA-N 0.000 description 1
- IDZUVPSBXLNXOJ-UHFFFAOYSA-N tert-butyl 4-[4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=CC(CC(=O)NC3=CN4C=CN=C4C=C3)=CC=2)=C1 IDZUVPSBXLNXOJ-UHFFFAOYSA-N 0.000 description 1
- CUTXAAGYMICASP-UHFFFAOYSA-N tert-butyl 4-[[4-[5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl]pyrazol-1-yl]methyl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C)CN1N=CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 CUTXAAGYMICASP-UHFFFAOYSA-N 0.000 description 1
- BOBSBLILWBUXJO-UHFFFAOYSA-N tert-butyl 4-[[4-[5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl]pyrazol-1-yl]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CN1N=CC(C=2SC(=CC=2)C(=O)NCC2=CC3=NC=CN3C=C2)=C1 BOBSBLILWBUXJO-UHFFFAOYSA-N 0.000 description 1
- NGCQUZIJAAHPNJ-UHFFFAOYSA-N tert-butyl 4-hydroxy-4-[5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(O)C1=CC=C(C(=O)NCC2=CC3=NC=CN3C=C2)S1 NGCQUZIJAAHPNJ-UHFFFAOYSA-N 0.000 description 1
- AORNZTKPXNOPIK-UHFFFAOYSA-N tert-butyl N-[2-fluoro-4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenyl]carbamate Chemical compound C1=C(F)C(NC(=O)OC(C)(C)C)=CC=C1C(=O)NCC1=CC2=NC=CN2C=C1 AORNZTKPXNOPIK-UHFFFAOYSA-N 0.000 description 1
- ODLKHRLTUGDRLM-UHFFFAOYSA-N tert-butyl N-[4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1C(=O)NCC1=CC2=NC=CN2C=C1 ODLKHRLTUGDRLM-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000003777 thiepinyl group Chemical group 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 125000005032 thiofuranyl group Chemical group S1C(=CC=C1)* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 210000003556 vascular endothelial cell Anatomy 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Definitions
- This invention pertains to compounds which inhibit the activity of NAMPT, compositions containing the compounds, and methods of treating diseases during which NAMPT is expressed.
- NAD+ (nicotinamide adenine dinucleotide) is a coenzyme that plays a critical role in many physiologically essential processes (Ziegkel, M. Eur. J. Biochem. 267, 1550-1564, 2000). NAD is necessary for several signaling pathways including among others poly ADP-ribosylation in DNA repair, mono-ADP-ribosylation in both the immune system and G-protein-coupled signaling, and NAD is also required by sirtuins for their deacetylase activity (Garten, A. et al Trends in Endocrinology and Metabolism, 20, 130-138, 2008).
- NAMPT also known as pre-B-cell-colony-enhancing factor (PBEF) and visfatin
- PBEF pre-B-cell-colony-enhancing factor
- visfatin is an enzyme that catalyzes the phosphoribosylation of nicotinamide and is the rate-limiting enzyme in one of two pathways that salvage NAD.
- NAMPT inhibitors have potential as anticancer agents. Cancer cells have a higher basal turnover of NAD and also display higher energy requirements compared with normal cells. Additionally, increased NAMPT expression has been reported in colorectal cancer (Van Beijnum, J. R. et al Int. J. Cancer 101, 118-127, 2002) and NAMPT is involved in angiogenesis (Kim, S. R. et al. Biochem. Biophys. Res. Commun. 357, 150-156, 2007). Small-molecule inhibitors of NAMPT have been shown to cause depletion of intracellular NAD+ levels and ultimately induce tumor cell death (Hansen, C M et al. Anticancer Res. 20, 42111-4220, 2000) as well as inhibit tumor growth in xenograft models (Olese, U. H. et al. Mol Cancer Ther. 9, 1609-1617, 2010).
- NAMPT inhibitors also have potential as therapeutic agents in inflammatory and metabolic disorders (Galli, M. et al Cancer Res. 70, 8-11, 2010).
- NAMPT is the predominant enzyme in T and B lymphocytes.
- Selective inhibition of NAMPT leads to NAD+ depletion in lymphocytes blocking the expansion that accompanies autoimmune disease progression whereas cell types expressing the other NAD+ generating pathways might be spared.
- a small molecule NAMPT inhibitor (FK866) has been shown to selectively block proliferation and induce apoptosis of activated T cells and was efficacious in animal models of arthritis (collagen-induced arthritis) (Busso, N. et al. Plos One 3, e2267, 2008).
- FK866 ameliorated the manifestations of experimental autoimmune encephalomyelitis (EAE), a model of T-cell mediated autoimmune disorders.
- EAE experimental autoimmune encephalomyelitis
- NaMPT activity increases NF-kB transcriptional activity in human vascular endothelial cell, resulting in MMP-2 and MMP-9 activation, suggesting a role for NAMPT inhibitors in the prevention of inflammatory mediated complications of obesity and type 2 diabetes (Adya, R. et. Al. Diabetes Care, 31, 758-760, 2008).
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IB)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and
- Z is CH, C—F, C—Cl, C—Br, C—I or N;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 1 is hydrogen, F, Cl, Br, or I
- Z is CR 2 ;
- R 2 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R 3x phenyl and heterocyclyl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 at each occurrence is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I;
- R 11 at each occurrence is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 11 alkyl is optionally substituted with NH(CH 3 ), heterocyclyl, SCH 2 CH(NH 2 )C(O)OH, OCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 NH 2 , or NHC(O)CH 2 CH(NH 2 )C(O)OH;
- n 4, 5, or 6;
- n 1 or 2;
- R 1 is NHC(O)R 3 ;
- R 2 is hydrogen; and
- R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenyl;
- R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
- R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is furanyl; the R 3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
- R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is thienyl; the R 3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
- R 1 is NHC(O)NHR 3 ; and R 2 is hydrogen.
- R 1 is CH 2 NHC(O)R 3 ; and R 2 is hydrogen.
- R 1 is hydrogen; and R 2 is CH 2 NHC(O)NHR 3 .
- R 1 is hydrogen; and R 2 is CH 2 NHC(O)R 3 .
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 1 is NHC(O)NHR 3 ;
- R 2 is hydrogen; and
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 1 is CH 2 NHC(O)R 3 ;
- R 2 is hydrogen; and
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 1 is hydrogen;
- R 2 is CH 2 NHC(O)NHR 3 ; and
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 1 is hydrogen;
- R 2 is CH 2 NHC(O)R 3 ; and
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 1 is NHC(O)NHR 3 ;
- R 2 is hydrogen; and
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 1 is CH 2 NHC(O)R 3 ;
- R 2 is hydrogen; and
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 1 is hydrogen;
- R 2 is CH 2 NHC(O)NHR 3 ; and
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 1 is hydrogen;
- R 2 is CH 2 NHC(O)R 3 ; and
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- Still another embodiment pertains to compounds, which are
- Still another embodiment pertains to compounds of Formula (IA), selected from the group consisting of
- Another embodiment pertains to a composition for treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic upus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress
- Another embodiment pertains to a method of treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult
- Another embodiment pertains to a method of treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult
- alkyl (alone or in combination with another term(s)) means a straight- or branched-chain saturated hydrocarbyl substituent typically containing from 1 to about 10 carbon atoms; or in another embodiment, from 1 to about 8 carbon atoms; in another embodiment, from 1 to about 6 carbon atoms; and in another embodiment, from 1 to about 4 carbon atoms.
- substituents include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, and hexyl and the like.
- alkenyl (alone or in combination with another term(s)) means a straight- or branched-chain hydrocarbyl substituent containing one or more double bonds and typically from 2 to about 10 carbon atoms; or in another embodiment, from 2 to about 8 carbon atoms; in another embodiment, from 2 to about 6 carbon atoms; and in another embodiment, from 2 to about 4 carbon atoms.
- substituents include ethenyl (vinyl), 2-propenyl, 3-propenyl, 1,4-pentadienyl, 1,4-butadienyl, 1-butenyl, 2-butenyl, and 3-butenyl and the like.
- alkynyl (alone or in combination with another term(s)) means a straight- or branched-chain hydrocarbyl substituent containing one or more triple bonds and typically from 2 to about 10 carbon atoms; or in another embodiment, from 2 to about 8 carbon atoms; in another embodiment, from 2 to about 6 carbon atoms; and in another embodiment, from 2 to about 4 carbon atoms.
- substituents include ethynyl, 2-propynyl, 3-propynyl, 2-butynyl, and 3-butynyl and the like.
- carbocyclyl (alone or in combination with another term(s)) means a saturated cyclic (i.e., “cycloalkyl”), partially saturated cyclic (i.e., “cycloalkenyl”), or completely unsaturated (i.e., “aryl”) hydrocarbyl substituent containing from 3 to 14 carbon ring atoms (“ring atoms” are the atoms bound together to form the ring or rings of a cyclic substituent).
- a carbocyclyl may be a single-ring (monocyclic) or polycyclic ring structure.
- a carbocyclyl may be a single ring structure, which typically contains from 3 to 8 ring atoms, more typically from 3 to 6 ring atoms, and even more typically 5 to 6 ring atoms.
- Examples of such single-ring carbocyclyls include cyclopropyl (cyclopropanyl), cyclobutyl (cyclobutanyl), cyclopentyl (cyclopentanyl), cyclopentenyl, cyclopentadienyl, cyclohexyl (cyclohexanyl), cyclohexenyl, cyclohexadienyl, and phenyl.
- a carbocyclyl may alternatively be polycyclic (i.e., may contain more than one ring).
- polycyclic carbocyclyls include bridged, fused, and spirocyclic carbocyclyls.
- a spirocyclic carbocyclyl one atom is common to two different rings.
- An example of a spirocyclic carbocyclyl is spiropentanyl.
- a bridged carbocyclyl the rings share at least two common non-adjacent atoms.
- bridged carbocyclyls include bicyclo[2.2.1]heptanyl, bicyclo[2.2.1]hept-2-enyl, and adamantanyl.
- two or more rings may be fused together, such that two rings share one common bond.
- Examples of two- or three-fused ring carbocyclyls include naphthalenyl, tetrahydronaphthalenyl (tetralinyl), indenyl, indanyl (dihydroindenyl), anthracenyl, phenanthrenyl, and decalinyl.
- cycloalkyl (alone or in combination with another term(s)) means a saturated cyclic hydrocarbyl substituent containing from 3 to 14 carbon ring atoms.
- a cycloalkyl may be a single carbon ring, which typically contains from 3 to 8 carbon ring atoms and more typically from 3 to 6 ring atoms.
- single-ring cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
- a cycloalkyl may alternatively be polycyclic or contain more than one ring. Examples of polycyclic cycloalkyls include bridged, fused, and spirocyclic carbocyclyls.
- aryl (alone or in combination with another term(s)) means an aromatic carbocyclyl containing from 6 to 14 carbon ring atoms.
- An aryl may be monocyclic or polycyclic (i.e., may contain more than one ring). In the case of polycyclic aromatic rings, only one ring the polycyclic system is required to be unsaturated while the remaining ring(s) may be saturated, partially saturated or unsaturated.
- aryls include phenyl, naphthalenyl, indenyl, indanyl, and tetrahydronapthyl.
- the number of carbon atoms in a hydrocarbyl substituent is indicated by the prefix “C x -C y -”, wherein x is the minimum and y is the maximum number of carbon atoms in the substituent.
- C 1 -C 6 -alkyl refers to an alkyl substituent containing from 1 to 6 carbon atoms.
- C 3 -C 8 -cycloalkyl means a saturated hydrocarbyl ring containing from 3 to 8 carbon ring atoms.
- hydrogen (alone or in combination with another term(s)) means a hydrogen radical, and may be depicted as —H.
- hydroxy (alone or in combination with another term(s)) means —OH.
- amino (alone or in combination with another term(s)) means —NH 2 .
- halogen or “halo” (alone or in combination with another term(s)) means a fluorine radical (which may be depicted as —F), chlorine radical (which may be depicted as —Cl), bromine radical (which may be depicted as —Br), or iodine radical (which may be depicted as —I).
- a non-hydrogen radical is in the place of hydrogen radical on a carbon or nitrogen of the substituent.
- a substituted alkyl substituent is an alkyl substituent in which at least one non-hydrogen radical is in the place of a hydrogen radical on the alkyl substituent.
- monofluoroalkyl is alkyl substituted with a fluoro radical
- difluoroalkyl is alkyl substituted with two fluoro radicals. It should be recognized that if there are more than one substitution on a substituent, each non-hydrogen radical may be identical or different (unless otherwise stated).
- substituent may be either (1) not substituted or (2) substituted. If a substituent is described as being optionally substituted with up to a particular number of non-hydrogen radicals, that substituent may be either (1) not substituted; or (2) substituted by up to that particular number of non-hydrogen radicals or by up to the maximum number of substitutable positions on the substituent, whichever is less. Thus, for example, if a substituent is described as a heteroaryl optionally substituted with up to 3 non-hydrogen radicals, then any heteroaryl with less than 3 substitutable positions would be optionally substituted by up to only as many non-hydrogen radicals as the heteroaryl has substitutable positions.
- tetrazolyl (which has only one substitutable position) would be optionally substituted with up to one non-hydrogen radical.
- an amino nitrogen is described as being optionally substituted with up to 2 non-hydrogen radicals, then a primary amino nitrogen will be optionally substituted with up to 2 non-hydrogen radicals, whereas a secondary amino nitrogen will be optionally substituted with up to only 1 non-hydrogen radical.
- haloalkyl means an alkyl substituent in which at least one hydrogen radical is replaced with a halogen radical.
- haloalkyls include chloromethyl, 1-bromoethyl, fluoromethyl, difluoromethyl, trifluoromethyl, and 1,1,1-trifluoroethyl. It should be recognized that if a substituent is substituted by more than one halogen radical, those halogen radicals may be identical or different (unless otherwise stated).
- the prefix “perhalo” indicates that every hydrogen radical on the substituent to which the prefix is attached is replaced with independently selected halogen radicals, i.e., each hydrogen radical on the substituent is replaced with a halogen radical. If all the halogen radicals are identical, the prefix typically will identify the halogen radical. Thus, for example, the term “perfluoro” means that every hydrogen radical on the substituent to which the prefix is attached is substituted with a fluorine radical. To illustrate, the term “perfluoroalkyl” means an alkyl substituent wherein a fluorine radical is in the place of each hydrogen radical.
- carbonyl (alone or in combination with another term(s)) means —C(O)—.
- aminocarbonyl (alone or in combination with another term(s)) means —C(O)—NH 2 .
- oxy (alone or in combination with another term(s)) means an ether substituent, and may be depicted as —O—.
- alkylhydroxy (alone or in combination with another term(s)) means -alkyl-OH.
- alkylamino (alone or in combination with another term(s)) means -alkyl-NH 2 .
- alkyloxy (alone or in combination with another term(s)) means an alkylether substituent, i.e., —O-alkyl.
- alkylether substituent i.e., —O-alkyl.
- substituents include methoxy (—O—CH 3 ), ethoxy, n-propoxy, isopropoxy, n-butoxy, iso-butoxy, sec-butoxy, and tert-butoxy.
- alkylcarbonyl (alone or in combination with another term(s)) means —C(O)-alkyl.
- aminoalkylcarbonyl (alone or in combination with another term(s)) means —C(O)-alkyl-NH 2 .
- alkyloxycarbonyl (alone or in combination with another term(s)) means —C(O)—O-alkyl.
- carbocyclylcarbonyl (alone or in combination with another term(s)) means —C(O)-carbocyclyl.
- heterocyclylcarbonyl (alone or in combination with another term(s)) means —C(O)-heterocyclyl.
- carbocyclylalkylcarbonyl (alone or in combination with another term(s)) means —C(O)-alkyl-carbocyclyl.
- heterocyclylalkylcarbonyl (alone or in combination with another term(s)) means —C(O)-alkyl-heterocyclyl.
- carbocyclyloxycarbonyl (alone or in combination with another term(s)) means —C(O)—O-carbocyclyl.
- carbocyclylalkyloxycarbonyl (alone or in combination with another term(s)) means —C(O)—O-alkyl-carbocyclyl.
- thio or “thia” (alone or in combination with another term(s)) means a thiaether substituent, i.e., an ether substituent wherein a divalent sulfur atom is in the place of the ether oxygen atom. Such a substituent may be depicted as —S—.
- alkyl-thio-alkyl means alkyl-S-alkyl (alkyl-sulfanyl-alkyl).
- thiol or “sulfhydryl” (alone or in combination with another term(s)) means a sulfhydryl substituent, and may be depicted as —SH.
- (thiocarbonyl) (alone or in combination with another term(s)) means a carbonyl wherein the oxygen atom has been replaced with a sulfur. Such a substituent may be depicted as —C(S)—.
- sulfonyl (alone or in combination with another term(s)) means —S(O) 2 —.
- aminosulfonyl (alone or in combination with another term(s)) means —S(O) 2 —NH 2 .
- sulfinyl or “sulfoxido” (alone or in combination with another term(s)) means —S(O)—.
- heterocyclyl (alone or in combination with another term(s)) means a saturated (i.e., “heterocycloalkyl”), partially saturated (i.e., “heterocycloalkenyl”), or completely unsaturated (i.e., “heteroaryl”) ring structure containing a total of 3 to 14 ring atoms. At least one of the ring atoms is a heteroatom (i.e., oxygen, nitrogen, or sulfur), with the remaining ring atoms being independently selected from the group consisting of carbon, oxygen, nitrogen, and sulfur.
- a heterocyclyl may be a single-ring (monocyclic) or polycyclic ring structure.
- a heterocyclyl may be a single ring, which typically contains from 3 to 7 ring atoms, more typically from 3 to 6 ring atoms, and even more typically 5 to 6 ring atoms.
- single-ring heterocyclyls include 1,2,3,6-tetrahydropyridine, thiomorpholinyl, tetrahydropyranyl, furanyl, dihydrofuranyl, tetrahydrofuranyl, thiophenyl (thiofuranyl), dihydrothiophenyl, tetrahydrothiophenyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, triazolyl, tetrazolyl, oxazolyl, oxazolidinyl, isoxazolidinyl, isox
- a heterocyclyl may alternatively be polycyclic (i.e., may contain more than one ring).
- polycyclic heterocyclyls include bridged, fused, and spirocyclic heterocyclyls.
- a spirocyclic heterocyclyl one atom is common to two different rings.
- a bridged heterocyclyl the rings share at least two common non-adjacent atoms.
- two or more rings may be fused together, such that two rings share one common bond.
- fused-ring heterocyclyls include hexahydro-furo[3,4-c]pyrrole, hexahydro-furo[3,4-b]pyrrole, octahydro-pyrrolo[3,4-b]pyridine, octahydro-pyrrolo[3,4-c]pyridine, (3aR,6aR)-5-methyl-octahydro-pyrrolo[3,4-b]pyrrole, (3aR,6aR)-octahydro-pyrrolo[3,4-b]pyrrole, 6-methyl-2,6-diaza-bicyclo[3.2.0]heptane, (3aS,6aR)-2-methyl-octahydro-pyrrolo[3,4-c]pyrrole, decahydro-[1,5]naphthyridine, 2,3-dihydrobenzofuranyl, 2,3,4,9-tetrahydro-1H-pyrido[3,
- fused-ring heterocyclyls include benzo-fused heterocyclyls, such as benzimidazolyl, benzo[d][1,3]dioxolyl, indolyl, isoindolyl (isobenzazolyl, pseudoisoindolyl), indoleninyl (pseudoindolyl), isoindazolyl (benzpyrazolyl), benzazinyl (including quinolinyl (1-benzazinyl) or isoquinolinyl (2-benzazinyl)), phthalazinyl, quinoxalinyl, quinazolinyl, benzodiazinyl (including cinnolinyl (1,2-benzodiazinyl) or quinazolinyl (1,3-benzodiazinyl)), benzopyranyl (including chromanyl or isochromanyl), benzoxazinyl (including 1,3,2-benzoxazinyl,
- 5-6 membered heteroaryl (alone or in combination with another term(s)) means aromatic heterocyclyl containing a total of 5 to 6 ring atoms. At least one of the ring atoms is a heteroatom (i.e., oxygen, nitrogen, or sulfur), with the remaining ring atoms being independently selected from the group consisting of carbon, oxygen, nitrogen, and sulfur.
- a heteroatom i.e., oxygen, nitrogen, or sulfur
- heterocycloalkyl (alone or in combination with another term(s)) means a saturated heterocyclyl.
- heteroaryl (alone or in combination with another term(s)) means an aromatic heterocyclyl containing from 5 to 14 ring atoms.
- a heteroaryl may be a single ring or 2 or 3 fused rings.
- heteroaryl substituents include 6-membered ring substituents such as pyridyl, pyrazyl, pyrimidinyl, pyridazinyl, and 1,3,5-, 1,2,4- or 1,2,3-triazinyl; 5-membered ring substituents such as imidazyl, furanyl, thiophenyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, 1,2,3-, 1,2,4-, 1,2,5-, or 1,3,4-oxadiazolyl and isothiazolyl; 6/5-membered fused ring substituents such as benzothiofuranyl, benzisoxazolyl, benzoxazoly
- alkylcycloalkyl contains two components: alkyl and cycloalkyl.
- the C 1 -C 6 -prefix on C 1 -C 6 -alkylcycloalkyl means that the alkyl component of the alkylcycloalkyl contains from 1 to 6 carbon atoms; the C 1 -C 6 -prefix does not describe the cycloalkyl component.
- the prefix “halo” on haloalkyloxyalkyl indicates that only the alkyloxy component of the alkyloxyalkyl substituent is substituted with one or more halogen radicals.
- halogen substitution may alternatively or additionally occur on the alkyl component, the substituent would instead be described as “halogen-substituted alkyloxyalkyl” rather than “haloalkyloxyalkyl.” And finally, if the halogen substitution may only occur on the alkyl component, the substituent would instead be described as “alkyloxyhaloalkyl.”
- treat refers to a method of alleviating or abrogating a disease and/or its attendant symptoms.
- prevent refers to a method of preventing the onset of a disease and/or its attendant symptoms or barring a subject from acquiring a disease.
- prevent also include delaying the onset of a disease and/or its attendant symptoms and reducing a subject's risk of acquiring a disease.
- terapéuticaally effective amount refers to that amount of the compound being administered sufficient to prevent development of or alleviate to some extent one or more of the symptoms of the condition or disorder being treated.
- modulate refers to the ability of a compound to increase or decrease the function, or activity, of a kinase.
- “Modulation”, as used herein in its various forms, is intended to encompass antagonism, agonism, partial antagonism and/or partial agonism of the activity associated with kinase.
- Kinase inhibitors are compounds that, e.g., bind to, partially or totally block stimulation, decrease, prevent, delay activation, inactivate, desensitize, or down regulate signal transduction.
- Kinase activators are compounds that, e.g., bind to, stimulate, increase, open, activate, facilitate, enhance activation, sensitize or up regulate signal transduction.
- composition as used herein is intended to encompass a product comprising the specified ingredients in the specified amounts, as well as any product which results, directly or indirectly, from combination of the specified ingredients in the specified amounts.
- pharmaceutically acceptable it is meant the carrier, diluent or excipient must be compatible with the other ingredients of the formulation and not deleterious to the recipient thereof.
- the “subject” is defined herein to include animals such as mammals, including, but not limited to, primates (e.g., humans), cows, sheep, goats, horses, dogs, cats, rabbits, rats, mice and the like. In preferred embodiments, the subject is a human.
- the isotope-labeled compounds contain deuterium ( 2 H), tritium ( 3 H) or 14 C isotopes.
- Isotope-labeled compounds of this invention can be prepared by the general methods well known to persons having ordinary skill in the art. Such isotope-labeled compounds can be conveniently prepared by carrying out the procedures disclosed in the Examples disclosed herein and Schemes by substituting a readily available isotope-labeled reagent for a non-labeled reagent.
- compounds may be treated with isotope-labeled reagents to exchange a normal atom with its isotope, for example, hydrogen for deuterium can be exchanged by the action of a deuteric acid such as D 2 SO 4 /D 2 O.
- a deuteric acid such as D 2 SO 4 /D 2 O.
- non-radio active isotope containing drugs such as deuterated drugs called “heavy drugs,” can be used for the treatment of diseases and conditions related to NAMPT activity.
- Increasing the amount of an isotope present in a compound above its natural abundance is called enrichment.
- Examples of the amount of enrichment include from about 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 12, 16, 21, 25, 29, 33, 37, 42, 46, 50, 54, 58, 63, 67, 71, 75, 79, 84, 88, 92, 96, to about 100 mol %.
- Stable isotope labeling of a drug can alter its physico-chemical properties such as pKa and lipid solubility. These effects and alterations can affect the pharmacodynamic response of the drug molecule if the isotopic substitution affects a region involved in a ligand-receptor interaction. While some of the physical properties of a stable isotope-labeled molecule are different from those of the unlabeled one, the chemical and biological properties are the same, with one important exception: because of the increased mass of the heavy isotope, any bond involving the heavy isotope and another atom will be stronger than the same bond between the light isotope and that atom. Accordingly, the incorporation of an isotope at a site of metabolism or enzymatic transformation will slow said reactions potentially altering the pharmacokinetic profile or efficacy relative to the non-isotopic compound.
- Suitable groups for X, R 1 , and Z in all Formulas are independently selected.
- the described embodiments of the present invention may be combined. Such combination is contemplated and within the scope of the present invention.
- embodiments for any of X, R 1 , and Z can be combined with embodiments defined for any other of X, R 1 , and Z.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (I)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 ; and CH 2 NHC(O)R 3 ; and
- Z is CH or N;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 1 is hydrogen
- Z is CR 2 ;
- R 2 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 ; and CH 2 NHC(O)R 3 ; and
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R 3x phenyl and heterocyclyl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl;
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- n 4, 5, or 6;
- n 1 or 2;
- R 1 is NHC(O)R 3 ;
- R 2 is hydrogen; and
- R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenyl;
- R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
- R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is furanyl; the R 3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
- R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is thienyl; the R 3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
- X is N or CY 1 . In another embodiment of Formula (I), X is N. In another embodiment of Formula (I), X is CY 1 .
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I.
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I.
- X is CY 1 ; and Y 1 is Cl.
- X is CY 1 ; and Y 1 is hydrogen.
- Z is CH or N;
- R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and R 2 is hydrogen.
- Z is CH or N; R 1 is NHC(O)NHR 3 ; and R 2 is hydrogen.
- Z is CH or N; R 1 is NHC(O)NH(CH 2 ) m R 3x ; and R 2 is hydrogen.
- Z is CH or N; R 1 is CH 2 NHC(O)NHR 3 ; and R 2 is hydrogen.
- Z is CH or N; R 1 is NHC(O)R 3 ; and R 2 is hydrogen.
- Z is CH or N; R 1 is NHC(O)(CH 2 ) n R 3 ; and R 2 is hydrogen.
- Z is CH or N; R 1 is C(O)NH(CH 2 ) n R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R 1 is NHC(O)(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R 1 is C(O)NH(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R 1 is CH 2 C(O)NHR 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R 1 is CH 2 NHC(O)R 3 ; and R 2 is hydrogen.
- Z is CH;
- R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and R 2 is hydrogen.
- Z is CH; R 1 is NHC(O)NHR 3 ; and R 2 is hydrogen.
- Z is CH; R 1 is NHC(O)NH(CH 2 ) m R 3x ; and R 2 is hydrogen.
- Z is CH; R 1 is CH 2 NHC(O)NHR 3 ; and R 2 is hydrogen.
- Z is CH; R 1 is NHC(O)R 3 ; and R 2 is hydrogen.
- Z is CH; R 1 is NHC(O)(CH 2 ) n R 3 ; and R 2 is hydrogen.
- Z is CH; R 1 is C(O)NH(CH 2 ) n R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH; R 1 is NHC(O)(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH; R 1 is C(O)NH(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH; R 1 is CH 2 C(O)NHR 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH; R 1 is CH 2 NHC(O)R 3 ; and R 2 is hydrogen.
- Z is N;
- R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and R 2 is hydrogen.
- Z is N; R 1 is NHC(O)NHR 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is NHC(O)NH(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is CH 2 NHC(O)NHR 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is NHC(O)R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is NHC(O)(CH 2 ) n R 3 ; and R 2 is hydrogen.
- Z is N; R 1 is C(O)NH(CH 2 ) n R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is NHC(O)(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is C(O)NH(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is CH 2 C(O)NHR 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is CH 2 NHC(O)R 3 ; and R 2 is hydrogen.
- R 1 is hydrogen; Z is CR 2 ; and R 2 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3 , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)NHR 3 .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)NH(CH 2 ) m R 3x .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is CH 2 NHC(O)NHR 3 .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)R 3 .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)(CH 2 ) n R 3 .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is C(O)NH(CH 2 ) n R 3 .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)(CH 2 ) m R 3x .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is C(O)NH(CH 2 ) m R 3x .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is CH 2 C(O)NHR 3 .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is CH 2 NHC(O)R 3 .
- m is 4, 5, or 6. In another embodiment of Formula (I), m is 4. In another embodiment of Formula (I), m is 5. In another embodiment of Formula (I), m is 6.
- n is 1 or 2. In another embodiment of Formula (I), n is 1. In another embodiment of Formula (I), n is 2.
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R 3x phenyl and heterocycyl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 ,
- R 4 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NR 5 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I.
- R 7 at each occurrence, is alkyl or heterocyclyl.
- R 8 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (I), R 8 at each occurrence, is independently alkyl.
- R 9 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)
- R 9 at each occurrence is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (I), R 10 at each occurrence, is independently haloalkyl or alkyl.
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (I), R 11 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (I)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 ; and CH 2 NHC(O)R 3 ; and
- Z is CH or N;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen F, Cl, Br, and I;
- R 1 is hydrogen
- Z is CR 2 ;
- R 2 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , CH 2 C(O)NHR 3 ; and CH 2 NHC(O)R 3 ; and
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F,
- R 3x is independently heterocyclyl; wherein each R 3x heterocyclyl is substituted with one substituents independently selected from the group consisting of C(O)R 4 , CO(O)R 4 , F, Cl, Br and I;
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R 8 at each occurrence, is alkyl
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, and alkyl;
- R 11 at each occurrence, is alkyl
- n 4, or 5;
- n 1;
- R 1 is NHC(O)R 3 ;
- R 2 is hydrogen; and
- R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenyl;
- R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
- R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is furanyl; the R 3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
- R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is thienyl; the R 3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
- Still another embodiment pertains to compounds having Formula (I), which includes Examples 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114
- the present invention provides compounds of Formula (II)
- One embodiment pertains to compounds of Formula (II) or pharmaceutically acceptable salts thereof;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl;
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- X is N or CY 1 . In another embodiment of Formula (II), X is N. In another embodiment of Formula (II), X is CY 1 .
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I.
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I.
- X is CY 1 ; and Y 1 is Cl.
- X is CY 1 ; and Y 1 is hydrogen.
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)NHR 4 , NR 4
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 4 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NR 5 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I.
- R 7 at each occurrence, is alkyl or heterocyclyl.
- R 8 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (II), R 8 at each occurrence, is independently alkyl.
- R 9 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O
- R 9 at each occurrence is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (II), R 10 at each occurrence, is independently haloalkyl or alkyl.
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (II), R 11 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (II)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F,
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R 8 at each occurrence, is alkyl
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, and alkyl;
- R 11 at each occurrence, is alkyl
- Still another embodiment pertains to compounds having Formula (II), which includes Example 2; and pharmaceutically acceptable salts thereof.
- the present invention provides compounds of Formula (III)
- One embodiment pertains to compounds of Formula (III) or pharmaceutically acceptable salts thereof;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl;
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- X is N or CY 1 . In another embodiment of Formula (III), X is N. In another embodiment of Formula (III), X is CY 1 .
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I.
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I.
- X is CY 1 ; and Y 1 is Cl.
- X is CY 1 ; and Y 1 is hydrogen.
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 4 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NR 5 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I.
- R 7 at each occurrence, is alkyl or heterocyclyl.
- R 8 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (III), R 8 at each occurrence, is independently alkyl.
- R 9 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)
- R 9 at each occurrence is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (III), R 10 at each occurrence, is independently haloalkyl or alkyl.
- R 1 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (III), R 1 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (III)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F,
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R 8 at each occurrence, is alkyl
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, and alkyl;
- R 11 at each occurrence, is alkyl
- Still another embodiment pertains to compounds having Formula (III), which includes Examples 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 89, 106, 109, 110, 111, 112, 113, 396, and pharmaceutically acceptable salts thereof.
- Formula (III) includes Examples 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 89, 106, 109, 110, 111, 112, 113, 396, and pharmaceutically acceptable salts thereof.
- the present invention provides compounds of Formula (IV)
- One embodiment pertains to compounds of Formula (IV) or pharmaceutically acceptable salts thereof;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl;
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- X is N or CY 1 . In another embodiment of Formula (IV), X is N. In another embodiment of Formula (IV), X is CY 1 .
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I.
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I.
- X is CY 1 ; and Y 1 is Cl.
- X is CY 1 ; and Y 1 is hydrogen.
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 4 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NR 5 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I.
- R 7 at each occurrence, is alkyl or heterocyclyl.
- R 8 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IV), R 8 at each occurrence, is independently alkyl.
- R 9 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)
- R 9 at each occurrence is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IV), R 10 at each occurrence, is independently haloalkyl or alkyl.
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IV), R 11 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IV)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F,
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R 8 at each occurrence, is alkyl
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, and alkyl;
- R 11 at each occurrence, is alkyl
- Still another embodiment pertains to compounds having Formula (IV), which includes Examples 118, 216, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 243, 280, 281, 282, 283, 284, 285, 286, 287, 288, 289, 290, 291, 302, 303, 306, 307, 328, 329, 330, 331, 332, 333, 334, 335, 336, 337, 338, 364, 366, 379, 380, 381, 382, 383, 384, 385, 386, 387, 388, 389, 390, 391, 392, 404, 407, 424, 425, 426, 427, 428, 429, 430, 431, 432, 433, 434, 435, 438, 439, 442, 443, 444, 445, 446, 447, 448, 449, 450, 451, 452, 453, 454, 455, 456, 457, 458, 459, 460
- the present invention provides compounds of Formula (V)
- One embodiment pertains to compounds of Formula (V) or pharmaceutically acceptable salts thereof;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl;
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- X is N or CY 1 . In another embodiment of Formula (V), X is N. In another embodiment of Formula (V), X is CY 1 .
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I.
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I.
- X is CY 1 ; and Y 1 is Cl.
- X is CY 1 ; and Y 1 is hydrogen.
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 4 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NR 5 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I.
- R 7 at each occurrence, is alkyl or heterocyclyl.
- R 8 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (V), R 8 at each occurrence, is independently alkyl.
- R 9 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)
- R 9 at each occurrence is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (V), R 10 at each occurrence, is independently haloalkyl or alkyl.
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (V), R 11 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (V)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F,
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R 8 at each occurrence, is alkyl
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, and alkyl;
- R 11 at each occurrence, is alkyl
- Still another embodiment pertains to compounds having Formula (V), which include Examples 59, 60, 274, 275, 276, 277, 278, 279, 360, 362, and pharmaceutically acceptable salts thereof.
- the present invention provides compounds of Formula (VI)
- One embodiment pertains to compounds of Formula (VI) or pharmaceutically acceptable salts thereof;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl;
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- X is N or CY 1 . In another embodiment of Formula (VI), X is N. In another embodiment of Formula (VI), X is CY 1 .
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I.
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I.
- X is CY 1 ; and Y 1 is Cl.
- X is CY 1 ; and Y 1 is hydrogen.
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 4 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NR 5 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I.
- R 7 at each occurrence, is alkyl or heterocyclyl.
- R 8 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VI), R 8 at each occurrence, is independently alkyl.
- R 9 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)
- R 9 at each occurrence is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VI), R 10 at each occurrence, is independently haloalkyl or alkyl.
- R 10 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VI), R 10 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VI)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F,
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R 8 at each occurrence, is alkyl
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, and alkyl;
- R 11 at each occurrence, is alkyl
- Still another embodiment pertains to compounds having Formula (VI), which includes Examples 57, 117, 121, 138, 174, 181, 182, 185, 187, 188, 192, 193, 194, 195, 196, 197, 198, 199, 202, 203, 204, 205, 207, 208, 209, 210, 211, 212, 213, 214, 217, 218, 230, 231, 232, 233, 234, 235, 236, 237, 238, 239, 241, 242, 244, 245, 246, 247, 248, 249, 250, 251, 252, 253, 254, 255, 256, 257, 258, 259, 260, 261, 262, 263, 264, 265, 266, 267, 268, 269, 271, 272, 273, 292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 304, 305, 308, 309, 310, 311, 312, 313, 315, 316, 3
- the present invention provides compounds of Formula (VII)
- One embodiment pertains to compounds of Formula (VII) or pharmaceutically acceptable salts thereof;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl;
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- X is N or CY 1 . In another embodiment of Formula (VII), X is N. In another embodiment of Formula (VII), X is CY 1 .
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I.
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I.
- X is CY 1 ; and Y 1 is Cl.
- X is CY 1 ; and Y 1 is hydrogen.
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)NHR 4 , NR 4
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 4 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NR 5 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I.
- R 7 at each occurrence, is alkyl or heterocyclyl.
- R 8 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VII), R 8 at each occurrence, is independently alkyl.
- R 9 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O
- R 9 at each occurrence is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VII), R 10 at each occurrence, is independently haloalkyl or alkyl.
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VII), R 11 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VII)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F,
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R 8 at each occurrence, is alkyl
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, and alkyl;
- R 11 at each occurrence, is alkyl
- Still another embodiment pertains to compounds having Formula (VII), which includes Examples 52, 55, 56, 61, 75, 77, 78, 79, 80, 81, 82, 83, 85, 86, 87, 88, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 108, 114, 115, 116, 119, 120, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 17
- the present invention provides compounds of Formula (VIII)
- One embodiment pertains to compounds of Formula (VIII) or pharmaceutically acceptable salts thereof;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl;
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- X is N or CY 1 . In another embodiment of Formula (VIII), X is N. In another embodiment of Formula (VIII), X is CY 1 .
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I.
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I.
- X is CY 1 ; and Y 1 is Cl.
- X is CY 1 ; and Y 1 is hydrogen.
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)NHR 4 , NR 4
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 4 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NR 5 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(
- R 5 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I.
- R 7 at each occurrence, is alkyl or heterocyclyl.
- R 8 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIII), R 8 at each occurrence, is independently alkyl.
- R 9 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O
- R 9 at each occurrence is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIII), R 10 at each occurrence, is independently haloalkyl or alkyl.
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIII), R 11 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VIII)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F,
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R 8 at each occurrence, is alkyl
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, and alkyl;
- R 11 at each occurrence, is alkyl
- Still another embodiment pertains to compounds having Formula (VIII), which includes Example 322, and pharmaceutically acceptable salts thereof.
- the present invention provides compounds of Formula (IX)
- One embodiment pertains to compounds of Formula (IX) or pharmaceutically acceptable salts thereof;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl;
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- X is N or CY 1 . In another embodiment of Formula (IX), X is N. In another embodiment of Formula (IX), X is CY 1 .
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I.
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I.
- X is CY 1 ; and Y 1 is Cl.
- X is CY 1 ; and Y 1 is hydrogen.
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)NHR 4 , NR 4
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 4 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NR 5 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I.
- R 7 at each occurrence, is alkyl or heterocyclyl.
- R 8 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IX), R 8 at each occurrence, is independently alkyl.
- R 9 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O
- R 9 at each occurrence is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IX), R 10 at each occurrence, is independently haloalkyl or alkyl.
- R 11 at each occurrence is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IX), R 11 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IX)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F,
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R 8 at each occurrence, is alkyl
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
- R 10 at each occurrence is independently selected from the group consisting of haloalkyl, and alkyl;
- R 11 at each occurrence, is alkyl
- Still another embodiment pertains to compounds having Formula (IX), which includes Examples 53, 54, 76, 314, 323, 491, and pharmaceutically acceptable salts thereof.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IA)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and
- Z is CH, C—F, C—Cl, C—Br, C—I or N;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 1 is hydrogen, F, Cl, Br, or I
- Z is CR 2 ;
- R 2 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R 3x phenyl and heterocyclyl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 at each occurrence is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I;
- R 11 at each occurrence is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
- n 4, 5, or 6;
- n 1 or 2;
- R 1 is NHC(O)R 3 ;
- R 2 is hydrogen; and
- R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenyl;
- R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
- R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is furanyl; the R 3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
- R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is thienyl; the R 3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
- X is N or CY 1 . In another embodiment of Formula (IA), X is N. In another embodiment of Formula (IA), X is CY 1 .
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I.
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I.
- X is CY 1 ; and Y 1 is Cl.
- X is CY 1 ; and Y 1 is hydrogen.
- Z is CH, C—F, C—Cl, C—Br, C—I or N; and R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 .
- Z is CH or N; and R 1 is NHC(O)NHR 3 .
- Z is CH or N; and R 1 is NHC(O)NH(CH 2 ) m R 3x .
- Z is CH or N; and R 1 is CH 2 NHC(O)NHR 3 .
- Z is CH or N; and R 1 is NHC(O)R 3 .
- Z is CH or N; and R 1 is NHC(O)(CH 2 ) n R 3 .
- Z is CH or N; and R 1 is C(O)NH(CH 2 ) n R 3 .
- Z is CH or N; and R 1 is NHC(O)(CH 2 ) m R 3x .
- Z is CH or N; and R 1 is C(O)NH(CH 2 ) m R 3x .
- Z is CH or N; and R 1 is CH 2 C(O)NHR 3 .
- Z is CH or N; and R 1 is CH 2 NHC(O)R 3 .
- Z is CH; and R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 .
- Z is CH; and R 1 is NHC(O)NHR 3 .
- Z is CH; and R 1 is NHC(O)NH(CH 2 ) m R 3x .
- Z is CH; and R 1 is CH 2 NHC(O)NHR 3 .
- Z is CH; and R 1 is NHC(O)R 3 .
- Z is CH; and R 1 is NHC(O)(CH 2 ) n R 3 .
- Z is CH; and R 1 is C(O)NH(CH 2 ) n R 3 .
- Z is CH; and R 1 is NHC(O)(CH 2 ) m R 3x .
- Z is CH; and R 1 is C(O)NH(CH 2 ) m R 3x .
- Z is CH; and R 1 is CH 2 C(O)NHR 3 .
- Z is CH; and R 1 is CH 2 NHC(O)R 3 .
- Z is N; and R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 .
- Z is N; and R 1 is NHC(O)NHR 3 .
- Z is N; and R 1 is NHC(O)NH(CH 2 ) m R 3x .
- Z is N; and R 1 is CH 2 NHC(O)NHR 3 .
- Z is N; and R 1 is NHC(O)R 3 .
- Z is N; and R 1 is NHC(O)(CH 2 ) n R 3 .
- Z is N; and R 1 is C(O)NH(CH 2 ) n R 3 .
- Z is N; and R 1 is NHC(O)(CH 2 ) m R 3x .
- Z is N; and R 1 is C(O)NH(CH 2 ) m R 3x .
- Z is N; and R 1 is CH 2 C(O)NHR 3 .
- Z is N; and R 1 is CH 2 NHC(O)R 3 .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)NHR 3 .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)NH(CH 2 ) m R 3x .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is CH 2 NHC(O)NHR 3 .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)R 3 .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)(CH 2 ) n R 3 .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is C(O)NH(CH 2 ) n R 3 .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)(CH 2 ) m R 3x .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is C(O)NH(CH 2 ) m R 3x .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is CH 2 C(O)NHR 3 .
- R 1 is hydrogen; Z is CR 2 ; and R 2 is CH 2 NHC(O)R 3 .
- m is 4, 5, or 6. In another embodiment of Formula (IA), m is 4. In another embodiment of Formula (IA), m is 5. In another embodiment of Formula (IA), m is 6.
- n is 1 or 2. In another embodiment of Formula (IA), n is 1. In another embodiment of Formula (IA), n is 2.
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)NHR 4 , NR 4
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , SO 2 R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , SO 2 R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R 3x phenyl and heterocycyl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NHC(O)NHR
- R 4 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NR 5 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I.
- R 7 at each occurrence, is alkyl or heterocyclyl.
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IA), R 8 , at each occurrence, is independently alkyl.
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, and Cl.
- R 10 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I.
- R 10 at each occurrence is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- R 11 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IA), R 11 , at each occurrence, is independently alkyl.
- R 11 at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IA)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and
- Z is CH, C—F, or N;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, and Cl;
- R 1 is hydrogen
- Z is CR 2 ;
- R 2 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)OR
- R 3x is heterocyclyl; wherein the R 3x heterocyclyl is substituted with one, two, three or four substituents independently selected from the group consisting of C(O)R 4 , CO(O)R 4 , F, Cl, Br and I;
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
- R 5 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R 8 at each occurrence, is independently alkyl
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, Cl, Br and I;
- R 10 at each occurrence is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F;
- R 11 at each occurrence, is independently cycloalkyl or alkyl
- n 4, or 5;
- n 1;
- R 1 is NHC(O)R 3 ;
- R 2 is hydrogen; and
- R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenyl;
- R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
- R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is furanyl; the R 3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
- R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is thienyl; the R 3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
- Still another embodiment pertains to compounds having Formula (IA), which includes Examples 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113,
- the present invention provides compounds of Formula (IIA)
- One embodiment pertains to compounds of Formula (IIA) or pharmaceutically acceptable salts thereof;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R 11 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
- X is N or CY 1 . In another embodiment of Formula (IIA), X is N. In another embodiment of Formula (IIA), X is CY 1 .
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I.
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I.
- X is CY 1 ; and Y 1 is Cl.
- X is CY 1 ; and Y 1 is hydrogen.
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)NHR 4 , NR 4
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 4 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NR 5 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I.
- R 7 at each occurrence, is alkyl or heterocyclyl.
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IIA), R 8 , at each occurrence, is independently alkyl.
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
- R 10 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I.
- R 10 is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- R 11 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IIA), R 11 , at each occurrence, is independently alkyl. In another embodiment of Formula (IIA), R 11 , at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IIA)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
- R 5 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R 8 at each occurrence, is independently alkyl
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, Cl, Br and I;
- R 10 is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R 11 at each occurrence, is independently cycloalkyl or alkyl
- Still another embodiment pertains to compounds having Formula (IIA), which includes Example 2; and pharmaceutically acceptable salts thereof.
- the present invention provides compounds of Formula (IIIA)
- One embodiment pertains to compounds of Formula (IIIA) or pharmaceutically acceptable salts thereof;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R 11 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
- X is N or CY 1 . In another embodiment of Formula (IIIA), X is N. In another embodiment of Formula (IIIA), X is CY 1 .
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I.
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I.
- X is CY 1 ; and Y 1 is Cl.
- X is CY 1 ; and Y 1 is hydrogen.
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)NHR 4 , NR 4
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 4 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NR 5 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I.
- R 7 at each occurrence, is alkyl or heterocyclyl.
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IIIA), R 8 , at each occurrence, is independently alkyl.
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
- R 10 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I.
- R 10 is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- R 11 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IIIA), R 11 , at each occurrence, is independently alkyl. In another embodiment of Formula (IIIA), R 11 , at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IIIA)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
- R 5 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R 8 at each occurrence, is independently alkyl
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, Cl, Br and I;
- R 10 is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R 11 at each occurrence, is independently cycloalkyl or alkyl
- Still another embodiment pertains to compounds having Formula (IIIA), which includes 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 89, 106, 109, 110, 111, 112, 113, 396, and pharmaceutically acceptable salts thereof.
- Formula (IIIA) includes 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 89, 106, 109, 110, 111, 112, 113, 396, and pharmaceutically acceptable salts thereof.
- the present invention provides compounds of Formula (IVA)
- One embodiment pertains to compounds of Formula (IVA) or pharmaceutically acceptable salts thereof;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R 11 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
- X is N or CY 1 . In another embodiment of Formula (IVA), X is N. In another embodiment of Formula (IVA), X is CY 1 .
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I.
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I.
- X is CY 1 ; and Y 1 is Cl.
- X is CY 1 ; and Y 1 is hydrogen.
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)NHR 4 , NR 4
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 4 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NR 5 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I.
- R 7 at each occurrence, is alkyl or heterocyclyl.
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IVA), R 8 , at each occurrence, is independently alkyl.
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
- R 10 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I.
- R 10 in another embodiment, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- R 11 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IVA), R 11 , at each occurrence, is independently alkyl. In another embodiment of Formula (IVA), R 11 , at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IVA)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
- R 5 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R 8 at each occurrence, is independently alkyl
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, Cl, Br and I;
- R 10 is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R 11 at each occurrence, is independently cycloalkyl or alkyl
- Still another embodiment pertains to compounds having Formula (IVA), which includes Examples 118, 216, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 243, 280, 281, 282, 283, 284, 285, 286, 287, 288, 289, 290, 291, 302, 303, 306, 307, 328, 329, 330, 331, 332, 333, 334, 335, 336, 337, 338, 364, 366, 379, 380, 381, 382, 383, 384, 385, 386, 387, 388, 389, 390, 391, 392, 404, 407, 424, 425, 426, 427, 428, 429, 430, 431, 432, 433, 434, 435, 438, 439, 442, 443, 444, 445, 446, 447, 448, 449, 450, 451, 452, 453, 454, 455, 456, 457, 458, 459,
- the present invention provides compounds of Formula (VA)
- One embodiment pertains to compounds of Formula (VA) or pharmaceutically acceptable salts thereof;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 1 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R 11 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
- X is N or CY 1 . In another embodiment of Formula (VA), X is N. In another embodiment of Formula (VA), X is CY 1 .
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I.
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I.
- X is CY 1 ; and Y 1 is Cl.
- X is CY 1 ; and Y 1 is hydrogen.
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)N
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 4 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NR 5 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)
- R 5 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I.
- R 7 at each occurrence, is alkyl or heterocyclyl.
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VA), R 8 , at each occurrence, is independently alkyl.
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
- R 10 is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I.
- R 10 is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- R 11 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VA), R 11 , at each occurrence, is independently alkyl. In another embodiment of Formula (VA), R 11 , at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VA)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
- R 5 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R 8 at each occurrence, is independently alkyl
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, Cl, Br and I;
- R 10 is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R 11 at each occurrence, is independently cycloalkyl or alkyl
- Still another embodiment pertains to compounds having Formula (VA), which includes 59, 60, 274, 275, 276, 277, 278, 279, 360, 362, and pharmaceutically acceptable salts thereof.
- VA Formula (VA)
- the present invention provides compounds of Formula (VIA)
- One embodiment pertains to compounds of Formula (VIA) or pharmaceutically acceptable salts thereof;
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2
- R 4 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NH 2 ,
- R 7 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(
- R 10 is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R 11 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
- X is N or CY 1 . In another embodiment of Formula (VIA), X is N. In another embodiment of Formula (VIA), X is CY 1 .
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I.
- X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I.
- X is CY 1 ; and Y 1 is Cl.
- X is CY 1 ; and Y 1 is hydrogen.
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)NHR 4 , NR 4
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)
- R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I.
- R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
- R 4 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NR 5 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
- R 5 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(
- R 5 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
- R 6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I.
- R 7 at each occurrence, is alkyl or heterocyclyl.
- R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIA), R 8 , at each occurrence, is independently alkyl.
- R 9 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C
- R 9 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
- R 10 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I.
- R 10 is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- R 11 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIA), R 11 , at each occurrence, is independently alkyl. In another embodiment of Formula (VIA), R 11 , at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VIA)
- X is N or CY 1 ;
- Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)OR
- R 4 is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
- R 5 is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
- R 6 is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
- R 7 at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Dermatology (AREA)
- Virology (AREA)
- Diabetes (AREA)
- Communicable Diseases (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Transplantation (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Molecular Biology (AREA)
- Obesity (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
Abstract
Disclosed are compounds which inhibit the activity of NAMPT, compositions containing the compounds and methods of treating diseases during which NAMPT is expressed.
Description
- This application claims priority to U.S. Provisional Application Ser. No. 61/645,679, filed May 11, 2012, U.S. Provisional Application Ser. No. 61/718,998, filed Oct. 26, 2012, and U.S. Provisional Application Ser. No. 61/779,626, filed Mar. 13, 2013, which are incorporated by reference in their entirety.
- This invention pertains to compounds which inhibit the activity of NAMPT, compositions containing the compounds, and methods of treating diseases during which NAMPT is expressed.
- NAD+ (nicotinamide adenine dinucleotide) is a coenzyme that plays a critical role in many physiologically essential processes (Ziegkel, M. Eur. J. Biochem. 267, 1550-1564, 2000). NAD is necessary for several signaling pathways including among others poly ADP-ribosylation in DNA repair, mono-ADP-ribosylation in both the immune system and G-protein-coupled signaling, and NAD is also required by sirtuins for their deacetylase activity (Garten, A. et al Trends in Endocrinology and Metabolism, 20, 130-138, 2008).
- NAMPT (also known as pre-B-cell-colony-enhancing factor (PBEF) and visfatin) is an enzyme that catalyzes the phosphoribosylation of nicotinamide and is the rate-limiting enzyme in one of two pathways that salvage NAD.
- Increasing evidence suggests that NAMPT inhibitors have potential as anticancer agents. Cancer cells have a higher basal turnover of NAD and also display higher energy requirements compared with normal cells. Additionally, increased NAMPT expression has been reported in colorectal cancer (Van Beijnum, J. R. et al Int. J. Cancer 101, 118-127, 2002) and NAMPT is involved in angiogenesis (Kim, S. R. et al. Biochem. Biophys. Res. Commun. 357, 150-156, 2007). Small-molecule inhibitors of NAMPT have been shown to cause depletion of intracellular NAD+ levels and ultimately induce tumor cell death (Hansen, C M et al. Anticancer Res. 20, 42111-4220, 2000) as well as inhibit tumor growth in xenograft models (Olese, U. H. et al. Mol Cancer Ther. 9, 1609-1617, 2010).
- NAMPT inhibitors also have potential as therapeutic agents in inflammatory and metabolic disorders (Galli, M. et al Cancer Res. 70, 8-11, 2010). For example, NAMPT is the predominant enzyme in T and B lymphocytes. Selective inhibition of NAMPT leads to NAD+ depletion in lymphocytes blocking the expansion that accompanies autoimmune disease progression whereas cell types expressing the other NAD+ generating pathways might be spared. A small molecule NAMPT inhibitor (FK866) has been shown to selectively block proliferation and induce apoptosis of activated T cells and was efficacious in animal models of arthritis (collagen-induced arthritis) (Busso, N. et al. Plos One 3, e2267, 2008). FK866 ameliorated the manifestations of experimental autoimmune encephalomyelitis (EAE), a model of T-cell mediated autoimmune disorders. (Bruzzone, S et al. Plos One 4, e7897, 2009). NaMPT activity increases NF-kB transcriptional activity in human vascular endothelial cell, resulting in MMP-2 and MMP-9 activation, suggesting a role for NAMPT inhibitors in the prevention of inflammatory mediated complications of obesity and type 2 diabetes (Adya, R. et. Al. Diabetes Care, 31, 758-760, 2008).
- One embodiment, therefore, pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IB)
- or a therapeutically acceptable salt thereof, wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R1 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3; and
- Z is CH, C—F, C—Cl, C—Br, C—I or N; or
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R1 is hydrogen, F, Cl, Br, or I;
- Z is CR2; and
- R2 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3; and
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R3x phenyl and heterocyclyl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I;
- R11 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- m is 4, 5, or 6; and
- n is 1 or 2;
- with the provisos that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent;
- when X is CY1 and Y1 is hydrogen; R1 is NHC(O)R3; R2 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenyl;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is furanyl; the R3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is thienyl; the R3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is R3 phenyl; the phenyl is not substituted at the para position with SO2R4 or SO2NHR4.
- In another embodiment of Formula (IB), R1 is NHC(O)NHR3; and R2 is hydrogen. In another embodiment of Formula (IB), R1 is CH2NHC(O)R3; and R2 is hydrogen. In another embodiment of Formula (IB), R1 is hydrogen; and R2 is CH2NHC(O)NHR3. In another embodiment of Formula (IB), R1 is hydrogen; and R2 is CH2NHC(O)R3. In one embodiment of Formula (IB), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In one embodiment of Formula (IB), R1 is NHC(O)NHR3; R2 is hydrogen; and R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In one embodiment of Formula (IB), R1 is CH2NHC(O)R3; R2 is hydrogen; and R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In one embodiment of Formula (IB), R1 is hydrogen; R2 is CH2NHC(O)NHR3; and R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In one embodiment of Formula (IB), R1 is hydrogen; R2 is CH2NHC(O)R3; and R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IB), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IB), R1 is NHC(O)NHR3; R2 is hydrogen; and R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IB), R1 is CH2NHC(O)R3; R2 is hydrogen; and R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IB), R1 is hydrogen; R2 is CH2NHC(O)NHR3; and R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IB), R1 is hydrogen; R2 is CH2NHC(O)R3; and R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- Still another embodiment pertains to compounds, which are
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(3-methylbutyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-7-ylcarbamoyl)amino]-N-(3-methylbutyl)benzamide;
- 2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-phenylethyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(morpholin-4-yl)ethyl]benzamide;
- N-(1-hydroxy-2-methylpropan-2-yl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- N-benzyl-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- N-(cyclopentylmethyl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(piperidin-1-yl)propyl]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-phenoxyethyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(pyrrolidin-1-yl)ethyl]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(propan-2-yloxy)ethyl]benzamide;
- N-(2-hydroxy-2-methylpropyl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(2-oxopyrrolidin-1-yl)ethyl]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydrofuran-2-ylmethyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-propylbenzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(morpholin-4-yl)propyl]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-phenylbenzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-methylbutyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(2-oxopyrrolidin-1-yl)propyl]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydro-2H-pyran-4-ylmethyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydro-2H-pyran-2-ylmethyl)benzamide;
- N-[(1,1-dioxidotetrahydrothiophen-3-yl)methyl]-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(tetrahydrofuran-3-yl)acetamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea;
- 1-{4-[1-(2-hydroxy-2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(morpholin-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea;
- 1-{4-[1-(ethoxyacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(2-methoxyethoxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea;
- 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(1-methylpiperidin-4-yl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)urea;
- 1-(4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea;
- 2-ethoxy-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(tetrahydro-2H-pyran-4-yl)acetamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(morpholin-4-yl)acetamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(2-methoxyethoxy)acetamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-3-methoxy-2-methylpropanamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}butanamide;
- 4,4,4-trifluoro-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}butanamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}tetrahydro-2H-pyran-4-carboxamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-4-methylpentanamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-1-methylpiperidine-4-carboxamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}tetrahydro-2H-thiopyran-4-carboxamide 1,1-dioxide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-1,4-dioxane-2-carboxamide;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea;
- 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 2-[(4-cyanobenzyl)(3-methylbutanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide;
- 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide;
- 2-[(4-cyanobenzyl)(3-methylbutanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]butyl}piperidine-1-carboxylate;
- 4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}-N-(3-methylbutyl)benzamide;
- 2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)acetamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(3-methylbutyl)amino]-1,3-thiazole-5-carboxamide;
- 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(propan-2-yloxy)acetyl]piperidin-4-yl}butyl)urea;
- 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]butyl}-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-{4-[1-(cyclopropylacetyl)piperidin-4-yl]butyl}-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]butyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]butyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]butyl}urea;
- 1-{4-[1-(cyclopentylcarbonyl)piperidin-4-yl]butyl}-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]butyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(2-methoxyethoxy)acetyl]piperidin-4-yl}butyl)urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(morpholin-4-ylacetyl)piperidin-4-yl]butyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]butyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)piperidin-4-yl]butyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]butyl}urea;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 2-cyclopentyl-N-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}acetamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydrofuran-2-ylacetyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydro-2H-pyran-4-ylacetyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(morpholin-4-ylacetyl)amino]benzamide;
- 4-[(3-cyclopentylpropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[(propan-2-yloxy)acetyl]amino}benzamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate;
- N-{4-[(cyclopentylacetyl)amino]benzyl}imidazo[1,2-a]pyridine-6-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(3-phenylpyrrolidin-1-yl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methylbutyl)amino]-1,3-thiazole-5-carboxamide;
- 2-(1,3-dihydro-2H-isoindol-2-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- 4-[1-(2-hydroxy-2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(morpholin-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-3-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-2-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[3-(tetrahydrofuran-2-yl)propanoyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide;
- 4-[1-(cyclopentylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-3-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- 4-[1-(1,4-dioxan-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[(2-methoxyethoxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide;
- 4-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 4-{1-[(4,4-difluorocyclohexyl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea;
- 1-[4-(1-benzoylpiperidin-4-yl)butyl]-3-imidazo[1,2-a]pyridin-6-ylurea;
- 2-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[2-oxo-4-(tetrahydrofuran-3-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide;
- 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)acetamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(2-oxo-5-phenyl-1,3-oxazolidin-3-yl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methyl-1,3-thiazol-5-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methyl-1,3-thiazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(3-methyl-1,2-oxazol-5-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- 2-{[3-(3-chloro-1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(3-methoxy-1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- 2-{[(3,5-dimethyl-1,2-oxazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- 2-{[3-(3,5-dimethyl-1,2-oxazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1-methyl-1H-pyrazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(4-methyl-1,3-thiazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-2-ylmethyl)(1H-tetrazol-5-ylacetyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(1,2-oxazol-3-ylacetyl)(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1,2-oxazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-2-ylmethyl) [3-(1,3-thiazol-2-yl)propanoyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methylbutanoyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydrofuran-3-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-3-ylmethyl)(tetrahydro-2H-pyran-4-ylcarbonyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydrofuran-3-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-3-ylcarbonyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydro-2H-pyran-4-ylcarbonyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(3-methoxypropanoyl)[(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-3-ylcarbonyl) [(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2R)-tetrahydrofuran-2-ylmethyl](tetrahydro-2H-pyran-4-ylcarbonyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(3-methoxypropanoyl) [(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-3-ylcarbonyl) [(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2S)-tetrahydrofuran-2-ylmethyl](tetrahydro-2H-pyran-4-ylcarbonyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydro-2H-pyran-4-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-({[2-(propan-2-yloxy)ethyl]carbamoyl}[(2R)-tetrahydrofuran-2-ylmethyl]amino)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl][(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-({[2-(propan-2-yloxy)ethyl]carbamoyl}[(2S)-tetrahydrofuran-2-ylmethyl]amino)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydrofuran-3-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- 2-[5-(4-chlorophenyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide;
- 4-[(1-acetylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 4-{[1-(cyclopropylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}benzamide;
- 4-{[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide;
- 4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)benzamide;
- 4-[(1-butanoylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(3-methoxy-2-methylpropanoyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}benzamide;
- 4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropanoyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(cyclohexylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(2R)-2-hydroxybutyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4R)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide;
- 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(1-methyl-1H-pyrazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- 2-{[(1,3-dimethyl-1H-pyrazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4S)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 2-{(4R)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- 2-{(4S)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1-methyl-1H-pyrrol-2-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- 2-{[(1,5-dimethyl-1H-pyrazol-3-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-2-ylmethyl)(1,3-thiazol-4-ylacetyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(1,2-oxazol-3-ylacetyl)[(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(5-methyl-1,2-oxazol-3-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1,2-oxazol-5-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1,2-oxazol-4-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(2R)-tetrahydrofuran-2-ylmethyl](1,3-thiazol-4-ylacetyl)amino}-1,3-thiazole-5-carboxamide;
- 2-{[(1,5-dimethyl-1H-pyrazol-3-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1-methyl-1H-pyrazol-4-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- 2-{[(3,5-dimethyl-1,2-oxazol-4-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(1-methyl-1H-pyrazol-4-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1-methyl-1H-pyrrol-2-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- 2-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- tert-butyl {4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydro-2H-pyran-4-ylacetyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-2-ylacetyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[3-(tetrahydrofuran-2-yl)propanoyl]amino}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(propan-2-yloxy)acetyl]amino}benzamide; 4-[(3-cyclopentylpropanoyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(4-methylpentanoyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide;
- 4-[(4-cyanobenzyl)(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate;
- 2-{5-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(morpholin-4-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(3-hydroxy-3-methylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea;
- 1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide;
- 4-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 5-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]thiophene-2-carboxamide;
- 1-(4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 2-[(2S)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4R)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide;
- 5-[1-(cyclopropylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[(4R)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]thiophene-2-carboxamide;
- 2-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(5S)-2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(5R)-2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methoxyacetyl)piperidin-4-yl]thiophene-2-carboxamide;
- 5-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- 5-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(1,2-oxazol-5-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 5-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[(4R)-4-hydroxy-2-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[(4S)-4-hydroxy-2-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 1-[4-(1-benzoylpiperidin-4-yl)butyl]-3-imidazo[1,2-a]pyridin-7-ylurea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methylsulfonyl)piperidin-4-yl]thiophene-2-carboxamide;
- 5-[1-(cyclohexylmethyl)-5-ethyl-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methoxy-3,3-dimethylcyclohexyl)methyl]-5-methyl-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-4-methylpentanamide;
- 3-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)propanamide;
- N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(propan-2-yloxy)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydrofuran-2-yl)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydro-2H-pyran-4-yl)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-3-phenylpropanamide;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-4-methylpentanamide;
- 3-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)propanamide;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(propan-2-yloxy)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydrofuran-2-yl)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydro-2H-pyran-4-yl)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3-phenylpropanamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3R)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}phenyl)urea;
- tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3,6-dihydropyridine-1(2H)-carboxylate;
- tert-butyl (3R)-3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)pyrrolidine-1-carboxylate;
- tert-butyl {2-fluoro-4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-propyl-1H-pyrazol-4-yl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(morpholin-4-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-(1-ethyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(1,1-dioxidotetrahydrothiophen-3-yl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 2-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- 4-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-phenylthiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(methylsulfonyl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}pyrrolidine-1-carboxylate;
- tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)pyrrolidine-1-carboxylate;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)biphenyl-2-sulfonamide;
- 5-{1-[(2R)-2-hydroxypropyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-[(cyclopentylacetyl)amino]-3-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 1-{2-fluoro-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3R)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide;
- 4-[1-(cyclopropylacetyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- tert-butyl 4-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide;
- 5-[1-(1,4-dioxan-2-ylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(propan-2-yloxy)phenyl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide;
- tert-butyl 4-[4-(imidazo[1,2-a]pyridin-7-ylcarbamoyl)phenyl]piperidine-1-carboxylate;
- tert-butyl 4-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoyl)phenyl]piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(2-methylpropanoyl)amino]oxetan-3-yl}thiophene-2-carboxamide;
- 5-[3-(benzoylamino)oxetan-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(tetrahydrofuran-3-ylacetyl)amino]oxetan-3-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(pentanoylamino)oxetan-3-yl]thiophene-2-carboxamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)phenyl]urea;
- 1-(4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}phenyl)urea;
- 1-(4-{[(3R)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)urea;
- 1-(4-{[(3R)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydrofuran-3-ylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}phenyl)urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3R)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}benzamide;
- 5-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- 4-{[(3S)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{[(3S)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(3-methoxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide;
- 4-{[(3S)-1-butanoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide;
- 4-{[(3S)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{[(3S)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{[(3S)-1-(3-hydroxy-3-methylbutanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 2-(4-benzoylpiperazin-1-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(propan-2-yl)piperazin-1-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(2-methoxyethyl)piperazin-1-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide;
- 1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-phenyl-1,3-thiazole-5-carboxamide;
- 1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxamide;
- tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)azetidine-1-carboxylate;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate;
- tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(1,4-dioxan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]benzamide;
- 1-[4-(1-acetylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}phenyl)urea;
- 1-{4-[1-(cyclopropylacetyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-[4-(1-benzoylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(propan-2-yloxy)acetyl]pyrrolidin-3-yl}phenyl)urea;
- 1-{4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]phenyl}urea;
- 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(morpholin-4-ylacetyl)pyrrolidin-3-yl]phenyl}urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 4-{[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoyl]amino}-N-(tetrahydro-2H-pyran-2-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- N-[(3-chloroimidazo[1,2-a]pyridin-6-yl)methyl]-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide;
- 5-(4-hydroxytetrahydro-2H-pyran-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[3-hydroxy-1-(2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-(1-benzoyl-3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}azetidine-1-carboxylate;
- tert-butyl 4-hydroxy-4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[5-(piperidin-1-ylcarbonyl)-1,3-thiazol-2-yl]urea;
- 5-{3-hydroxy-1-[(2S)-2-methylbutanoyl]azetidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[3-hydroxy-1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 2-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}-N-(3-methylbutyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(3-{[(2S)-2-methylbutanoyl]amino}oxetan-3-yl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1-[1-(3-methylbutanoyl)piperidin-4-yl]-1H-pyrazole-3-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 4-[(1-acetylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]piperidin-4-yl}oxy)benzamide;
- 4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[(1-benzoylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)benzamide;
- 4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}benzamide;
- 4-{[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(morpholin-4-ylacetyl)piperidin-4-yl]oxy}benzamide;
- 1-{4-[(1-acetylazetidin-3-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-2-methylbutanoyl]azetidin-3-yl}oxy)phenyl]urea;
- 1-(4-{[1-(cyclopropylacetyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[(1-benzoylazetidin-3-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(propan-2-yloxy)acetyl]azetidin-3-yl}oxy)phenyl]urea;
- 1-(4-{[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)azetidin-3-yl]oxy}phenyl)urea;
- 1-(4-{[1-(1,4-dioxan-2-ylcarbonyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]oxy}phenyl)urea;
- tert-butyl (3R)-3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}pyrrolidine-1-carboxylate;
- 4-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 1-[4-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 4-{1-[(3,3-difluorocyclobutyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-2-methylbutanoyl]piperidin-4-yl}oxy)phenyl]urea;
- 1-(4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[(1-benzoylpiperidin-4-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)phenyl]urea;
- 1-(4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)azetidin-3-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]azetidin-3-yl}phenyl)urea;
- 1-{4-[1-(cyclopropylacetyl)azetidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-[4-(1-benzoylazetidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(propan-2-yloxy)acetyl]azetidin-3-yl}phenyl)urea;
- 1-{4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)azetidin-3-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]phenyl}urea;
- 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[6-(morpholin-4-yl)pyridin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methyltetrahydro-2H-pyran-2-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropanoyl)amino]cyclobutyl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylbutanoyl)amino]cyclobutyl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-{[(2S)-2-methylbutanoyl]amino}cyclobutyl)thiophene-2-carboxamide;
- 5-[1-(benzoylamino)cyclobutyl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3,3,3-trifluoropropanoyl)amino]cyclobutyl}thiophene-2-carboxamide;
- N-(1-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}cyclobutyl)tetrahydro-2H-pyran-4-carboxamide;
- tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}azetidine-1-carboxylate;
- 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 4-[1-(furan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(piperidin-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-phenoxybenzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)azetidin-3-yl]benzamide;
- tert-butyl 4-{4-[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoyl]phenyl}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide;
- 4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-phenoxyphenyl)urea;
- 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(2,2-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclohexylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide;
- 4-(1-butanoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylpent-2-enoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyloxetan-3-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1-cyanocyclopropyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopentylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-oxobutanoyl)piperidin-4-yl]benzamide;
- 4-{1-[(2,5-dimethylfuran-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(3-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(4-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-propanoylpiperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(2,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide;
- 2-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- 4-[(cyclopentylacetyl)amino]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]azetidin-3-yl}benzamide;
- 4-[1-(cyclopropylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-benzoylazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)azetidin-3-yl]benzamide;
- 5-[4-hydroxy-1-(3-methylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[4-hydroxy-1-(2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3,3-dimethylbutanoyl)-4-hydroxypiperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-(1-benzoyl-4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]azetidin-3-yl}oxy)benzamide;
- 4-{[1-(cyclopropylacetyl)azetidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[(1-benzoylazetidin-3-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- tert-butyl 4-{4-[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate;
- 2-cyclopentyl-N-(4-{[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)acetamide;
- tert-butyl 4-(4-{[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-1-ylcarbonyl)benzamide;
- 4-[1-(ethylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopropylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)azetidin-3-yl]benzamide;
- propan-2-yl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate;
- 2-methylpropyl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]piperidin-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-[1-(2-cyano-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3R)-tetrahydrofuran-3-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(cyclopentylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(cyclohexylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(cyclohexylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(furan-3-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]pyrrolidin-3-yl}benzamide;
- 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(ethylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopropylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(cyclopentylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)azetidin-3-yl]benzamide;
- 4-[1-(cyclopentylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(2,2-dimethylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)azetidin-3-yl]benzamide;
- 4-[1-(2-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(furan-2-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,4-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(2-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)azetidin-3-yl]benzamide;
- 4-[1-(4-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,2-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)azetidin-3-yl]benzamide;
- 4-[1-(3,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyanobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(cyclohexylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)azetidin-3-yl]benzamide;
- 4-[1-(cyclohexylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)azetidin-3-yl]benzamide;
- 4-[1-(furan-3-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrimidin-4-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(2,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]azetidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]azetidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]azetidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)pyrrolidin-3-yl]benzamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]phenyl}urea;
- 5-[1-(1,4-dioxan-2-ylmethyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate;
- 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide;
- tert-butyl 4-(4-{[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate;
- 2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]amino}phenyl)acetamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)piperidin-4-yl]benzamide;
- 4-[1-(cyclopropylsulfonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 5-{(1R)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{(1R)-3-methyl-1-[(tetrahydrofuran-3-ylacetyl)amino]butyl}thiophene-2-carboxamide;
- 5-{(1S)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1-phenylpiperidin-4-yl)-1,3-thiazole-5-carboxamide;
- 1-(4-{[(3R)-1-(2-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(3-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(4-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[4-(trifluoromethyl)benzoyl]pyrrolidin-3-yl}oxy)phenyl]urea;
- 1-(4-{[(3R)-1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(2-chlorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(4-chlorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(pyridin-2-yl)piperidin-4-yl]-1,3-thiazole-5-carboxamide;
- 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-[1-(2-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylacetyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide;
- 1-[4-(1-butanoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methylcyclopropyl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(cyclopropylacetyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]phenyl}urea;
- 1-(4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(phenylacetyl)piperidin-4-yl]phenyl}urea;
- 5-[1-(cyclopropylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 1-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(3-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(4-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[1-(3-fluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[1-(2,4-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[1-(2,5-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[1-(3,4-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[1-(3,5-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylacetyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methyl-2-phenylpropanoyl)pyrrolidin-3-yl]benzamide;
- 4-{1-[difluoro(phenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]furan-2-carboxamide;
- 4-[1-(2-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- 2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}acetamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- 5-(1-benzyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide;
- 5-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[4-(2-methylpropyl)phenyl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-2-methylbutanoyl]-1,2,3,6-tetrahydropyridin-4-yl}furan-2-carboxamide;
- 5-[1-(3,3-dimethylbutanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 5-[1-(cyclopropylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{1-[(2-methylpropyl)sulfonyl]pyrrolidin-3-yl}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(phenylsulfonyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]-1,2,3,6-tetrahydropyridin-4-yl}furan-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidine-1-carboxylate;
- 5-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(4-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-{1-[(3-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(3,5-difluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(2-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(4-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- 5-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- 5-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-4-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrazol-4-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- 5-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2E)-2-methylpent-2-enoyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- 5-{1-[(2,5-dimethylfuran-3-yl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-propanoylpyrrolidin-3-yl)thiophene-2-carboxamide;
- 5-{1-[(1-cyanocyclopropyl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-(1-butanoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-[1-(2,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(thiophen-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methylpiperidin-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 5-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyrazin-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylthiophen-2-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-3-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrazol-5-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- 5-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(phenylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide;
- 2-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- 5-[1-(2-fluorobenzoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 2-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide;
- 2-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- tert-butyl 4-[2-(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)ethyl]piperazine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide;
- 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide;
- 4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(3-methylbutanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(propan-2-ylsulfonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-5-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutyl)-1H-pyrazol-5-yl]furan-2-carboxamide;
- 5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{[2-(2-methylpropyl)pyrrolidin-1-yl]carbonyl}thiophene-2-carboxamide;
- 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide;
- 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(3-methylbutanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide;
- 5-[1-(2-methylpropanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3-methylbutanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- 5-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(1-methylpiperidin-4-yl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-cyanobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-6-ylacetyl)amino]phenyl}acetamide;
- tert-butyl 4-{4-[(imidazo[1,2-b]pyridazin-6-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate;
- 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-b]pyridazin-6-ylmethyl)benzamide;
- 5-(1-benzyl-3-cyclopropyl-1H-pyrazol-5-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(propan-2-ylsulfonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(phenylsulfonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylacetyl)amino]phenyl}piperidine-1-carboxylate;
- N-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-6-yl)acetamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(phenylsulfonyl)piperidin-4-yl]benzamide;
- 2-(imidazo[1,2-a]pyridin-6-yl)-N-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}acetamide;
- N-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-6-yl)acetamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(2-methoxyphenyl)acetyl]amino}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(phenylacetyl)amino]benzamide;
- 4-(benzoylamino)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 2,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide;
- 3,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide;
- 3,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide;
- 2,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide;
- 2-fluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide;
- N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-3-methoxybenzamide;
- 4-{[(2-fluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[2-(2-methylpropyl)pyrrolidin-1-yl]carbonyl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-methyl-2-(piperazin-1-yl)propanoyl]piperidin-4-yl}thiophene-2-carboxamide;
- N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-2-methoxybenzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(phenylsulfonyl)benzamide;
- 4-(phenylsulfonyl)-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)benzamide;
- 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tricyclo[3.3.1.1˜3,7˜]dec-1-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 5-(1-benzyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-oxatricyclo[3.3.1.1˜3,7˜]dec-1-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- 4-{[(2,5-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{[(2,4-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 5-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[3-cyclopropyl-1-(2-methoxyethyl)-1H-pyrazol-5-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 4-{[difluoro(phenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(2-methyl-2-phenylpropanoyl)amino]benzamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(phenylsulfonyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-(phenylsulfonyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-5-yl]thiophene-2-carboxamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}piperidine-1-carboxylate;
- N-[(3-chloroimidazo[1,2-a]pyrazin-6-yl)methyl]-4-[(cyclopentylacetyl)amino]benzamide;
- N-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide;
- 2-(imidazo[1,2-a]pyridin-7-yl)-N-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}acetamide;
- 1-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea;
- N-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-methyl-3-(2-methylpropyl)-1H-pyrazol-5-yl]thiophene-2-carboxamide;
- 5-[1-benzyl-3-(2-methylpropyl)-1H-pyrazol-5-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide;
- N-(2,5-difluorobenzyl)-N′-(imidazo[1,2-a]pyridin-7-ylmethyl)benzene-1,4-dicarboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[2-(propan-2-yl)pyrrolidin-1-yl]carbonyl}benzamide;
- N-{4-[5-(2,2-dimethylpropyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide;
- tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate;
- 4-{1-[(2-chloropyridin-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbut-2-enoyl)piperidin-4-yl]benzamide;
- 4-[1-(3-fluoro-4-methoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopent-1-en-1-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-[1-(2-ethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(4-fluorophenoxy)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxyphenyl)acetyl]piperidin-4-yl}benzamide;
- 4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(2-acetylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(methoxymethyl)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenylpropanoyl)piperidin-4-yl]benzamide;
- 4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[(2-methylpropyl)sulfonyl]acetyl}piperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenoxypropanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-({[(1R,2S)-2-methylcyclohexyl]oxy}acetyl)piperidin-4-yl]benzamide;
- 4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methoxyphenyl)acetyl]piperidin-4-yl}benzamide;
- 4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylbut-2-enoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxy-5-methylphenyl)acetyl]piperidin-4-yl}benzamide;
- 4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 1-(4-{1-[(2-chloropyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3-methylbut-2-enoyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methylcyclopent-1-en-1-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(2-ethylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(4-fluorophenoxy)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,4-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,5-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3-methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-oxo-2,3-dihydro-1H-inden-4-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-2-methylbut-2-enoyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(1H-indol-3-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrrolidin-1-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)benzamide;
- 4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-2,1-benzoxazol-3-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(2-chloro-3-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(pyridin-2-yl)cyclopropyl]carbonyl}piperidin-4-yl)benzamide;
- 4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,4-dihydro-2H-chromen-6-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(cyclohexyloxy)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(2-chloropyridin-3-yl)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(5-cyclopropyl-1,2-oxazol-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2H-chromen-3-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3,5-difluoropyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxycyclohexyl)carbonyl]piperidin-4-yl}benzamide;
- 4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-4-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-1,3-benzoxazol-6-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thieno[3,2-b]pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinolin-7-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(5,6,7,8-tetrahydroquinolin-3-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-7-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinoxalin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-3-(2-methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-3-(pyridin-2-yl)prop-2-enoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(8-methylimidazo[1,2-a]pyridin-2-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methyl-4H-furo[3,2-b]pyrrol-5-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-8-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[3-methyl-1-(prop-2-en-1-yl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)benzamide;
- 4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)pyrimidin-4-yl]carbonyl}piperidin-4-yl)benzamide;
- 4-{1-[(5,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)tetrahydro-2H-pyran-4-yl]carbonyl}piperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxy-6-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)phenyl]urea;
- 1-(4-{1-[(2S)-2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-tetrahydro-2,1-benzoxazol-3-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(4-{-[(2-chloro-5-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{-[(2-chloro-3-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-(pyridin-2-yl)cyclopropyl]carbonyl}piperidin-4-yl)phenyl]urea;
- 1-(4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-[4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,3-dihydro-1-benzofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxycyclohexyl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-4-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-1,3-benzoxazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(cinnolin-4-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(quinolin-7-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(5,6,7,8-tetrahydroquinolin-3-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-7-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(quinoxalin-2-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-(2-methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-(pyridin-2-yl)prop-2-enoyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(4-chloro-2,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(8-methylimidazo[1,2-a]pyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methyl-4H-furo[3,2-b]pyrrol-5-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(4-chloro-1-ethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-8-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[3-methyl-1-(prop-2-en-1-yl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)phenyl]urea;
- 1-{4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(5,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 4-{1-[(2-chloro-5-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-methyl-5-(propan-2-yl)furan-3-yl]carbonyl}piperidin-4-yl)benzamide;
- 1-(4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3,5-difluoropyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- tert-butyl 4-{3-fluoro-4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(piperidin-1-ylcarbonyl)piperidin-4-yl]benzamide;
- 1-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(4-methylpentanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(2-fluoro-4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2-cyanobenzoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-N,N-dimethylpiperidine-1-carboxamide;
- 1-{2-fluoro-4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 4-[(cyclopentylacetyl)amino]-N-[(7-fluoroimidazo[1,2-a]pyridin-6-yl)methyl]benzamide;
- N-[(7-fluoroimidazo[1,2-a]pyridin-6-yl)methyl]-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-2-(imidazo[1,2-a]pyridin-7-yl)acetamide;
- 5-{1-[2,2-dimethyl-3-(piperazin-1-yl)propyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3-amino-2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-{1-[(2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-indazol-6-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(5-cyclopropylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]acetyl}piperidin-4-yl)benzamide;
- 4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-1-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxy-5-methylpyridin-2-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[4-(propan-2-yl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-5-propyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-yl)propanoyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2,3-dihydro-1-benzofuran-7-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)-1,3-thiazol-4-yl]carbonyl}piperidin-4-yl)benzamide;
- 4-(1-{[1-(difluoromethyl)-5-methyl-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(4-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazolo[1,5-a]pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)-1,3-oxazol-4-yl]carbonyl}piperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxy-5-methylpyridin-3-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(5,6-dimethoxypyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2H-indazol-4-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2H-indazol-6-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-indazol-4-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(trifluoromethyl)furan-3-yl]carbonyl}piperidin-4-yl)benzamide;
- 1-(4-{1-[(2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(thieno[3,2-b]furan-5-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(5-cyclopropylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-[4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4-yl]carbonyl}piperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxy-5-methylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[4-(propan-2-yl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-5-propyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-yl)propanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(pyrazolo[1,5-a]pyridin-2-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2-(propan-2-yl)-1,3-oxazol-4-yl]carbonyl}piperidin-4-yl)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-7-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methoxy-5-methylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(5,6-dimethoxypyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2H-indazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2H-indazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2-(trifluoromethyl)furan-3-yl]carbonyl}piperidin-4-yl)phenyl]urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrimidin-4-yl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpyrimidin-4-yl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[6-(trifluoromethyl)pyrimidin-4-yl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide;
- 5-[1-({3,5-dimethyl-7-[2-(methylamino)ethoxy]tricyclo[3.3.1.13,7]dec-1-yl}methyl)-5-methyl-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide;
- 4-(1-benzoylpiperidin-4-yl)-2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide;
- 2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide;
- 2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-({4-methyl-1-[2-(piperazin-1-yl)ethyl]piperidin-4-yl}methyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- S-(2-{4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidin-1-yl}-2-oxoethyl)-L-cysteine;
- 5-(1-{[1-(15-amino-4,7,10,13-tetraoxapentadecan-1-oyl)-4-methylpiperidin-4-yl]methyl}-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- S-{2-[(3-{4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidin-1-yl}-3-oxopropyl)amino]-2-oxoethyl}-L-cysteine; and pharmaceutically acceptable salts thereof.
- Still another embodiment pertains to compounds of Formula (IA), selected from the group consisting of
- 4-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluoro-4-methoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(2-acetylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(methoxymethyl)benzoyl]piperidin-4-yl}benzamide;
- 4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxy-6-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; and pharmaceutically acceptable salts thereof.
- Another embodiment pertains to a composition for treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic upus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia, said composition comprising an excipient and a therapeutically effective amount of a compound of Formula (IB), or pharmaceutically acceptable salts thereof.
- Another embodiment pertains to a method of treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia in a patient, said method comprising administering to the patient a therapeutically effective amount of a compound of Formula (IB), or pharmaceutically acceptable salts thereof.
- Another embodiment pertains to a method of treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia or spleen cancer in a patient, said method comprising administering to the patient therapeutically effective amount of the compound of Formula (IB), or pharmaceutically acceptable salts thereof; and a therapeutically effective amount of one additional therapeutic agent or more than one additional therapeutic agent.
- This detailed description is intended only to acquaint others skilled in the art with Applicants' invention, its principles, and its practical application so that others skilled in the art may adapt and apply the invention in its numerous forms, as they may be best suited to the requirements of a particular use. This description and its specific examples are intended for purposes of illustration only. This invention, therefore, is not limited to the embodiments described in this patent application, and may be variously modified.
- Unless otherwise defined herein, scientific and technical terms used in connection with the present invention shall have the meanings that are commonly understood by those of ordinary skill in the art. The meaning and scope of the terms should be clear, however, in the event of any latent ambiguity, definitions provided herein take precedent over any dictionary or extrinsic definition. In this application, the use of “or” means “and/or” unless stated otherwise. Furthermore, the use of the term “including”, as well as other forms, such as “includes” and “included”, is not limiting. With reference to the use of the words “comprise” or “comprises” or “comprising” in this patent application (including the claims), Applicants note that unless the context requires otherwise, those words are used on the basis and clear understanding that they are to be interpreted inclusively, rather than exclusively, and that Applicants intend each of those words to be so interpreted in construing this patent application, including the claims below. For a variable that occurs more than one time in any substituent or in the compound of the invention or any other formulae herein, its definition on each occurrence is independent of its definition at every other occurrence. Combinations of substituents are permissible only if such combinations result in stable compounds. Stable compounds are compounds which can be isolated in a useful degree of purity from a reaction mixture.
- It is meant to be understood that proper valences are maintained for all combinations herein, that monovalent moieties having more than one atom are attached through their left ends, and that divalent moieties are drawn from left to right.
- As used in the specification and the appended claims, unless specified to the contrary, the following terms have the meaning indicated:
- The term “alkyl” (alone or in combination with another term(s)) means a straight- or branched-chain saturated hydrocarbyl substituent typically containing from 1 to about 10 carbon atoms; or in another embodiment, from 1 to about 8 carbon atoms; in another embodiment, from 1 to about 6 carbon atoms; and in another embodiment, from 1 to about 4 carbon atoms. Examples of such substituents include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, and hexyl and the like.
- The term “alkenyl” (alone or in combination with another term(s)) means a straight- or branched-chain hydrocarbyl substituent containing one or more double bonds and typically from 2 to about 10 carbon atoms; or in another embodiment, from 2 to about 8 carbon atoms; in another embodiment, from 2 to about 6 carbon atoms; and in another embodiment, from 2 to about 4 carbon atoms. Examples of such substituents include ethenyl (vinyl), 2-propenyl, 3-propenyl, 1,4-pentadienyl, 1,4-butadienyl, 1-butenyl, 2-butenyl, and 3-butenyl and the like.
- The term “alkynyl” (alone or in combination with another term(s)) means a straight- or branched-chain hydrocarbyl substituent containing one or more triple bonds and typically from 2 to about 10 carbon atoms; or in another embodiment, from 2 to about 8 carbon atoms; in another embodiment, from 2 to about 6 carbon atoms; and in another embodiment, from 2 to about 4 carbon atoms. Examples of such substituents include ethynyl, 2-propynyl, 3-propynyl, 2-butynyl, and 3-butynyl and the like.
- The term “carbocyclyl” (alone or in combination with another term(s)) means a saturated cyclic (i.e., “cycloalkyl”), partially saturated cyclic (i.e., “cycloalkenyl”), or completely unsaturated (i.e., “aryl”) hydrocarbyl substituent containing from 3 to 14 carbon ring atoms (“ring atoms” are the atoms bound together to form the ring or rings of a cyclic substituent). A carbocyclyl may be a single-ring (monocyclic) or polycyclic ring structure.
- A carbocyclyl may be a single ring structure, which typically contains from 3 to 8 ring atoms, more typically from 3 to 6 ring atoms, and even more typically 5 to 6 ring atoms. Examples of such single-ring carbocyclyls include cyclopropyl (cyclopropanyl), cyclobutyl (cyclobutanyl), cyclopentyl (cyclopentanyl), cyclopentenyl, cyclopentadienyl, cyclohexyl (cyclohexanyl), cyclohexenyl, cyclohexadienyl, and phenyl. A carbocyclyl may alternatively be polycyclic (i.e., may contain more than one ring). Examples of polycyclic carbocyclyls include bridged, fused, and spirocyclic carbocyclyls. In a spirocyclic carbocyclyl, one atom is common to two different rings. An example of a spirocyclic carbocyclyl is spiropentanyl. In a bridged carbocyclyl, the rings share at least two common non-adjacent atoms. Examples of bridged carbocyclyls include bicyclo[2.2.1]heptanyl, bicyclo[2.2.1]hept-2-enyl, and adamantanyl. In a fused-ring carbocyclyl system, two or more rings may be fused together, such that two rings share one common bond. Examples of two- or three-fused ring carbocyclyls include naphthalenyl, tetrahydronaphthalenyl (tetralinyl), indenyl, indanyl (dihydroindenyl), anthracenyl, phenanthrenyl, and decalinyl.
- The term “cycloalkyl” (alone or in combination with another term(s)) means a saturated cyclic hydrocarbyl substituent containing from 3 to 14 carbon ring atoms. A cycloalkyl may be a single carbon ring, which typically contains from 3 to 8 carbon ring atoms and more typically from 3 to 6 ring atoms. Examples of single-ring cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. A cycloalkyl may alternatively be polycyclic or contain more than one ring. Examples of polycyclic cycloalkyls include bridged, fused, and spirocyclic carbocyclyls.
- The term “aryl” (alone or in combination with another term(s)) means an aromatic carbocyclyl containing from 6 to 14 carbon ring atoms. An aryl may be monocyclic or polycyclic (i.e., may contain more than one ring). In the case of polycyclic aromatic rings, only one ring the polycyclic system is required to be unsaturated while the remaining ring(s) may be saturated, partially saturated or unsaturated. Examples of aryls include phenyl, naphthalenyl, indenyl, indanyl, and tetrahydronapthyl.
- In some instances, the number of carbon atoms in a hydrocarbyl substituent (e.g., alkyl, alkenyl, alkynyl, or cycloalkyl) is indicated by the prefix “Cx-Cy-”, wherein x is the minimum and y is the maximum number of carbon atoms in the substituent. Thus, for example, “C1-C6-alkyl” refers to an alkyl substituent containing from 1 to 6 carbon atoms. Illustrating further, C3-C8-cycloalkyl means a saturated hydrocarbyl ring containing from 3 to 8 carbon ring atoms.
- The term “hydrogen” (alone or in combination with another term(s)) means a hydrogen radical, and may be depicted as —H.
- The term “hydroxy” (alone or in combination with another term(s)) means —OH.
- The term “carboxy” (alone or in combination with another term(s)) means —C(O)—OH.
- The term “amino” (alone or in combination with another term(s)) means —NH2.
- The term “halogen” or “halo” (alone or in combination with another term(s)) means a fluorine radical (which may be depicted as —F), chlorine radical (which may be depicted as —Cl), bromine radical (which may be depicted as —Br), or iodine radical (which may be depicted as —I).
- If a substituent is described as being “substituted”, a non-hydrogen radical is in the place of hydrogen radical on a carbon or nitrogen of the substituent. Thus, for example, a substituted alkyl substituent is an alkyl substituent in which at least one non-hydrogen radical is in the place of a hydrogen radical on the alkyl substituent. To illustrate, monofluoroalkyl is alkyl substituted with a fluoro radical, and difluoroalkyl is alkyl substituted with two fluoro radicals. It should be recognized that if there are more than one substitution on a substituent, each non-hydrogen radical may be identical or different (unless otherwise stated).
- If a substituent is described as being “optionally substituted”, the substituent may be either (1) not substituted or (2) substituted. If a substituent is described as being optionally substituted with up to a particular number of non-hydrogen radicals, that substituent may be either (1) not substituted; or (2) substituted by up to that particular number of non-hydrogen radicals or by up to the maximum number of substitutable positions on the substituent, whichever is less. Thus, for example, if a substituent is described as a heteroaryl optionally substituted with up to 3 non-hydrogen radicals, then any heteroaryl with less than 3 substitutable positions would be optionally substituted by up to only as many non-hydrogen radicals as the heteroaryl has substitutable positions. To illustrate, tetrazolyl (which has only one substitutable position) would be optionally substituted with up to one non-hydrogen radical. To illustrate further, if an amino nitrogen is described as being optionally substituted with up to 2 non-hydrogen radicals, then a primary amino nitrogen will be optionally substituted with up to 2 non-hydrogen radicals, whereas a secondary amino nitrogen will be optionally substituted with up to only 1 non-hydrogen radical.
- This patent application uses the terms “substituent” and “radical” interchangeably.
- The prefix “halo” indicates that the substituent to which the prefix is attached is substituted with one or more independently selected halogen radicals. For example, haloalkyl means an alkyl substituent in which at least one hydrogen radical is replaced with a halogen radical. Examples of haloalkyls include chloromethyl, 1-bromoethyl, fluoromethyl, difluoromethyl, trifluoromethyl, and 1,1,1-trifluoroethyl. It should be recognized that if a substituent is substituted by more than one halogen radical, those halogen radicals may be identical or different (unless otherwise stated).
- The prefix “perhalo” indicates that every hydrogen radical on the substituent to which the prefix is attached is replaced with independently selected halogen radicals, i.e., each hydrogen radical on the substituent is replaced with a halogen radical. If all the halogen radicals are identical, the prefix typically will identify the halogen radical. Thus, for example, the term “perfluoro” means that every hydrogen radical on the substituent to which the prefix is attached is substituted with a fluorine radical. To illustrate, the term “perfluoroalkyl” means an alkyl substituent wherein a fluorine radical is in the place of each hydrogen radical.
- The term “carbonyl” (alone or in combination with another term(s)) means —C(O)—.
- The term “aminocarbonyl” (alone or in combination with another term(s)) means —C(O)—NH2.
- The term “oxo” (alone or in combination with another term(s)) means (═O).
- The term “oxy” (alone or in combination with another term(s)) means an ether substituent, and may be depicted as —O—.
- The term “alkylhydroxy” (alone or in combination with another term(s)) means -alkyl-OH.
- The term “alkylamino” (alone or in combination with another term(s)) means -alkyl-NH2.
- The term “alkyloxy” (alone or in combination with another term(s)) means an alkylether substituent, i.e., —O-alkyl. Examples of such a substituent include methoxy (—O—CH3), ethoxy, n-propoxy, isopropoxy, n-butoxy, iso-butoxy, sec-butoxy, and tert-butoxy.
- The term “alkylcarbonyl” (alone or in combination with another term(s)) means —C(O)-alkyl.
- The term “aminoalkylcarbonyl” (alone or in combination with another term(s)) means —C(O)-alkyl-NH2.
- The term “alkyloxycarbonyl” (alone or in combination with another term(s)) means —C(O)—O-alkyl.
- The term “carbocyclylcarbonyl” (alone or in combination with another term(s)) means —C(O)-carbocyclyl.
- Similarly, the term “heterocyclylcarbonyl” (alone or in combination with another term(s)) means —C(O)-heterocyclyl.
- The term “carbocyclylalkylcarbonyl” (alone or in combination with another term(s)) means —C(O)-alkyl-carbocyclyl.
- Similarly, the term “heterocyclylalkylcarbonyl” (alone or in combination with another term(s)) means —C(O)-alkyl-heterocyclyl.
- The term “carbocyclyloxycarbonyl” (alone or in combination with another term(s)) means —C(O)—O-carbocyclyl.
- The term “carbocyclylalkyloxycarbonyl” (alone or in combination with another term(s)) means —C(O)—O-alkyl-carbocyclyl.
- The term “thio” or “thia” (alone or in combination with another term(s)) means a thiaether substituent, i.e., an ether substituent wherein a divalent sulfur atom is in the place of the ether oxygen atom. Such a substituent may be depicted as —S—. This, for example, “alkyl-thio-alkyl” means alkyl-S-alkyl (alkyl-sulfanyl-alkyl).
- The term “thiol” or “sulfhydryl” (alone or in combination with another term(s)) means a sulfhydryl substituent, and may be depicted as —SH.
- The term “(thiocarbonyl)” (alone or in combination with another term(s)) means a carbonyl wherein the oxygen atom has been replaced with a sulfur. Such a substituent may be depicted as —C(S)—.
- The term “sulfonyl” (alone or in combination with another term(s)) means —S(O)2—.
- The term “aminosulfonyl” (alone or in combination with another term(s)) means —S(O)2—NH2.
- The term “sulfinyl” or “sulfoxido” (alone or in combination with another term(s)) means —S(O)—.
- The term “heterocyclyl” (alone or in combination with another term(s)) means a saturated (i.e., “heterocycloalkyl”), partially saturated (i.e., “heterocycloalkenyl”), or completely unsaturated (i.e., “heteroaryl”) ring structure containing a total of 3 to 14 ring atoms. At least one of the ring atoms is a heteroatom (i.e., oxygen, nitrogen, or sulfur), with the remaining ring atoms being independently selected from the group consisting of carbon, oxygen, nitrogen, and sulfur. A heterocyclyl may be a single-ring (monocyclic) or polycyclic ring structure.
- A heterocyclyl may be a single ring, which typically contains from 3 to 7 ring atoms, more typically from 3 to 6 ring atoms, and even more typically 5 to 6 ring atoms. Examples of single-ring heterocyclyls include 1,2,3,6-tetrahydropyridine, thiomorpholinyl, tetrahydropyranyl, furanyl, dihydrofuranyl, tetrahydrofuranyl, thiophenyl (thiofuranyl), dihydrothiophenyl, tetrahydrothiophenyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, triazolyl, tetrazolyl, oxazolyl, oxazolidinyl, isoxazolidinyl, isoxazolyl, thiazolyl, isothiazolyl, thiazolinyl, isothiazolinyl, thiazolidinyl, isothiazolidinyl, thiodiazolyl, oxadiazolyl (including 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl (furazanyl), or 1,3,4-oxadiazolyl), oxatriazolyl (including 1,2,3,4-oxatriazolyl or 1,2,3,5-oxatriazolyl), dioxazolyl (including 1,2,3-dioxazolyl, 1,2,4-dioxazolyl, 1,3,2-dioxazolyl, or 1,3,4-dioxazolyl), oxathiazolyl, oxathiolyl, oxathiolanyl, pyranyl, dihydropyranyl, thiopyranyl, tetrahydrothiopyranyl, pyridinyl (azinyl), piperidinyl, diazinyl (including pyridazinyl (1,2-diazinyl), pyrimidinyl (1,3-diazinyl), or pyrazinyl (1,4-diazinyl)), piperazinyl, pyrrolidin-2-only, triazinyl (including 1,3,5-triazinyl, 1,2,4-triazinyl, and 1,2,3-triazinyl)), oxazinyl (including 1,2-oxazinyl, 1,3-oxazinyl, or 1,4-oxazinyl)), oxathiazinyl (including 1,2,3-oxathiazinyl, 1,2,4-oxathiazinyl, 1,2,5-oxathiazinyl, or 1,2,6-oxathiazinyl)), oxadiazinyl (including 1,2,3-oxadiazinyl, 1,2,4-oxadiazinyl, 1,4,2-oxadiazinyl, or 1,3,5-oxadiazinyl)), morpholinyl, azepinyl, oxepinyl, thiepinyl, and diazepinyl.
- A heterocyclyl may alternatively be polycyclic (i.e., may contain more than one ring). Examples of polycyclic heterocyclyls include bridged, fused, and spirocyclic heterocyclyls. In a spirocyclic heterocyclyl, one atom is common to two different rings. In a bridged heterocyclyl, the rings share at least two common non-adjacent atoms. In a fused-ring heterocyclyl, two or more rings may be fused together, such that two rings share one common bond. Examples of fused-ring heterocyclyls include hexahydro-furo[3,4-c]pyrrole, hexahydro-furo[3,4-b]pyrrole, octahydro-pyrrolo[3,4-b]pyridine, octahydro-pyrrolo[3,4-c]pyridine, (3aR,6aR)-5-methyl-octahydro-pyrrolo[3,4-b]pyrrole, (3aR,6aR)-octahydro-pyrrolo[3,4-b]pyrrole, 6-methyl-2,6-diaza-bicyclo[3.2.0]heptane, (3aS,6aR)-2-methyl-octahydro-pyrrolo[3,4-c]pyrrole, decahydro-[1,5]naphthyridine, 2,3-dihydrobenzofuranyl, 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indolyl, thieno[3,2-c]pyridinyl, furo[3,2-c]pyridinyl, phthalazin-1(2H)-onyl, isoquinolinyl, isoquinolin-1(2H)-onyl, 5,6,7,8-tetrahydrophthalazin-1(2H)-onyl, fluorophthalazin-1(2H)-onyl, (Z)-3H-benzo[d][1,2]diazepin-4(5H)-onyl, (trifluoromethyl)phthalazin-1(2H)-onyl, pyrrolo[1,2-d][1,2,4]triazin-1(2H)-onyl, 1,2,3,4-tetrahydroisoquinolinyl, 2,3-dihydrobenzo[b][1,4]dioxinyl, 5,6,7,8-tetrahydrophthalazin-1(2H)-onyl, 5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazinyl, 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazinyl, thieno[3,2-c]pyridinyl, furo[3,2-c]pyridinyl, indolizinyl, pyranopyrrolyl, 4H-quinolizinyl, purinyl, naphthyridinyl, pyridopyridinyl (including pyrido[3,4-b]-pyridinyl, pyrido[3,2-b]-pyridinyl, or pyrido[4,3-b]-pyridinyl), and pteridinyl. Other examples of fused-ring heterocyclyls include benzo-fused heterocyclyls, such as benzimidazolyl, benzo[d][1,3]dioxolyl, indolyl, isoindolyl (isobenzazolyl, pseudoisoindolyl), indoleninyl (pseudoindolyl), isoindazolyl (benzpyrazolyl), benzazinyl (including quinolinyl (1-benzazinyl) or isoquinolinyl (2-benzazinyl)), phthalazinyl, quinoxalinyl, quinazolinyl, benzodiazinyl (including cinnolinyl (1,2-benzodiazinyl) or quinazolinyl (1,3-benzodiazinyl)), benzopyranyl (including chromanyl or isochromanyl), benzoxazinyl (including 1,3,2-benzoxazinyl, 1,4,2-benzoxazinyl, 2,3,1-benzoxazinyl, or 3,1,4-benzoxazinyl), and benzisoxazinyl (including 1,2-benzisoxazinyl or 1,4-benzisoxazinyl). Examples of spirocyclic heterocyclyls include 1,4-dioxa-8-azaspiro[4.5]decanyl.
- The term “5-6 membered heteroaryl” (alone or in combination with another term(s)) means aromatic heterocyclyl containing a total of 5 to 6 ring atoms. At least one of the ring atoms is a heteroatom (i.e., oxygen, nitrogen, or sulfur), with the remaining ring atoms being independently selected from the group consisting of carbon, oxygen, nitrogen, and sulfur.
- The term “heterocycloalkyl” (alone or in combination with another term(s)) means a saturated heterocyclyl.
- The term “heteroaryl” (alone or in combination with another term(s)) means an aromatic heterocyclyl containing from 5 to 14 ring atoms. A heteroaryl may be a single ring or 2 or 3 fused rings. Examples of heteroaryl substituents include 6-membered ring substituents such as pyridyl, pyrazyl, pyrimidinyl, pyridazinyl, and 1,3,5-, 1,2,4- or 1,2,3-triazinyl; 5-membered ring substituents such as imidazyl, furanyl, thiophenyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, 1,2,3-, 1,2,4-, 1,2,5-, or 1,3,4-oxadiazolyl and isothiazolyl; 6/5-membered fused ring substituents such as benzothiofuranyl, benzisoxazolyl, benzoxazolyl, and purinyl; and 6/6-membered fused rings such as benzopyranyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, and benzoxazinyl.
- A prefix attached to a multi-component substituent only applies to the first component. To illustrate, the term “alkylcycloalkyl” contains two components: alkyl and cycloalkyl. Thus, the C1-C6-prefix on C1-C6-alkylcycloalkyl means that the alkyl component of the alkylcycloalkyl contains from 1 to 6 carbon atoms; the C1-C6-prefix does not describe the cycloalkyl component. To illustrate further, the prefix “halo” on haloalkyloxyalkyl indicates that only the alkyloxy component of the alkyloxyalkyl substituent is substituted with one or more halogen radicals. If halogen substitution may alternatively or additionally occur on the alkyl component, the substituent would instead be described as “halogen-substituted alkyloxyalkyl” rather than “haloalkyloxyalkyl.” And finally, if the halogen substitution may only occur on the alkyl component, the substituent would instead be described as “alkyloxyhaloalkyl.”
- The terms “treat”, “treating” and “treatment” refer to a method of alleviating or abrogating a disease and/or its attendant symptoms.
- The terms “prevent”, “preventing” and “prevention” refer to a method of preventing the onset of a disease and/or its attendant symptoms or barring a subject from acquiring a disease. As used herein, “prevent”, “preventing” and “prevention” also include delaying the onset of a disease and/or its attendant symptoms and reducing a subject's risk of acquiring a disease.
- The term “therapeutically effective amount” refers to that amount of the compound being administered sufficient to prevent development of or alleviate to some extent one or more of the symptoms of the condition or disorder being treated.
- The term “modulate” refers to the ability of a compound to increase or decrease the function, or activity, of a kinase. “Modulation”, as used herein in its various forms, is intended to encompass antagonism, agonism, partial antagonism and/or partial agonism of the activity associated with kinase. Kinase inhibitors are compounds that, e.g., bind to, partially or totally block stimulation, decrease, prevent, delay activation, inactivate, desensitize, or down regulate signal transduction. Kinase activators are compounds that, e.g., bind to, stimulate, increase, open, activate, facilitate, enhance activation, sensitize or up regulate signal transduction.
- The term “composition” as used herein is intended to encompass a product comprising the specified ingredients in the specified amounts, as well as any product which results, directly or indirectly, from combination of the specified ingredients in the specified amounts. By “pharmaceutically acceptable” it is meant the carrier, diluent or excipient must be compatible with the other ingredients of the formulation and not deleterious to the recipient thereof.
- The “subject” is defined herein to include animals such as mammals, including, but not limited to, primates (e.g., humans), cows, sheep, goats, horses, dogs, cats, rabbits, rats, mice and the like. In preferred embodiments, the subject is a human.
- Compounds of the invention can exist in isotope-labeled or -enriched form containing one or more atoms having an atomic mass or mass number different from the atomic mass or mass number most abundantly found in nature. Isotopes can be radioactive or non-radioactive isotopes. Isotopes of atoms such as hydrogen, carbon, phosphorous, sulfur, fluorine, chlorine, and iodine include, but are not limited to, 2H, 3H, 13C, 14C, 15N, 18O, 32P, 35S, 18F, 36Cl, and 125I. Compounds that contain other isotopes of these and/or other atoms are within the scope of this invention.
- In another embodiment, the isotope-labeled compounds contain deuterium (2H), tritium (3H) or 14C isotopes. Isotope-labeled compounds of this invention can be prepared by the general methods well known to persons having ordinary skill in the art. Such isotope-labeled compounds can be conveniently prepared by carrying out the procedures disclosed in the Examples disclosed herein and Schemes by substituting a readily available isotope-labeled reagent for a non-labeled reagent. In some instances, compounds may be treated with isotope-labeled reagents to exchange a normal atom with its isotope, for example, hydrogen for deuterium can be exchanged by the action of a deuteric acid such as D2SO4/D2O. In addition to the above, relevant procedures and intermediates are disclosed, for instance, in Lizondo, J et al., Drugs Fut, 21(11), 1116 (1996); Brickner, S J et al., J Med Chem, 39(3), 673 (1996); Mallesham, B et al., Org Lett, 5(7), 963 (2003); PCT publications WO1997010223, WO2005099353, WO1995007271, WO2006008754; U.S. Pat. Nos. 7,538,189; 7,534,814; 7,531,685; 7,528,131; 7,521,421; 7,514,068; 7,511,013; and US Patent Application Publication Nos. 20090137457; 20090131485; 20090131363; 20090118238; 20090111840; 20090105338; 20090105307; 20090105147; 20090093422; 20090088416; and 20090082471, the methods are hereby incorporated by reference.
- The isotope-labeled compounds of the invention may be used as standards to determine the effectiveness in binding assays. Isotope containing compounds have been used in pharmaceutical research to investigate the in vivo metabolic fate of the compounds by evaluation of the mechanism of action and metabolic pathway of the nonisotope-labeled parent compound (Blake et al. J. Pharm. Sci. 64, 3, 367-391 (1975)). Such metabolic studies are important in the design of safe, effective therapeutic drugs, either because the in vivo active compound administered to the patient or because the metabolites produced from the parent compound prove to be toxic or carcinogenic (Foster et al., Advances in Drug Research Vol. 14, pp. 2-36, Academic press, London, 1985; Kato et al., J. Labelled Comp. Radiopharmaceut., 36(10):927-932 (1995); Kushner et al., Can. J. Physiol. Pharmacol., 77, 79-88 (1999).
- In addition, non-radio active isotope containing drugs, such as deuterated drugs called “heavy drugs,” can be used for the treatment of diseases and conditions related to NAMPT activity. Increasing the amount of an isotope present in a compound above its natural abundance is called enrichment. Examples of the amount of enrichment include from about 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 12, 16, 21, 25, 29, 33, 37, 42, 46, 50, 54, 58, 63, 67, 71, 75, 79, 84, 88, 92, 96, to about 100 mol %. Replacement of up to about 15% of normal atom with a heavy isotope has been effected and maintained for a period of days to weeks in mammals, including rodents and dogs, with minimal observed adverse effects (Czajka D M and Finkel A J, Ann. N.Y. Acad. Sci. 196084: 770; Thomson J F, Ann. New York Acad. Sci 1960 84: 736; Czakja D M et al., Am. J. Physiol. 1961 201: 357). Acute replacement of as high as 15%-23% in human fluids with deuterium was found not to cause toxicity (Blagojevic N et al. in “Dosimetry & Treatment Planning for Neutron Capture Therapy”, Zamenhof R, Solares G and Harling O Eds. 1994. Advanced Medical Publishing, Madison Wis. pp. 125-134; Diabetes Metab. 23: 251 (1997)).
- Stable isotope labeling of a drug can alter its physico-chemical properties such as pKa and lipid solubility. These effects and alterations can affect the pharmacodynamic response of the drug molecule if the isotopic substitution affects a region involved in a ligand-receptor interaction. While some of the physical properties of a stable isotope-labeled molecule are different from those of the unlabeled one, the chemical and biological properties are the same, with one important exception: because of the increased mass of the heavy isotope, any bond involving the heavy isotope and another atom will be stronger than the same bond between the light isotope and that atom. Accordingly, the incorporation of an isotope at a site of metabolism or enzymatic transformation will slow said reactions potentially altering the pharmacokinetic profile or efficacy relative to the non-isotopic compound.
- Suitable groups for X, R1, and Z in all Formulas are independently selected. The described embodiments of the present invention may be combined. Such combination is contemplated and within the scope of the present invention. For example, it is contemplated that embodiments for any of X, R1, and Z can be combined with embodiments defined for any other of X, R1, and Z.
- One embodiment, therefore, pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (I)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R1 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3; and CH2NHC(O)R3; and
- Z is CH or N; or
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R1 is hydrogen;
- Z is CR2; and
- R2 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3; and CH2NHC(O)R3; and
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R3x phenyl and heterocyclyl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl;
- R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- m is 4, 5, or 6; and
- n is 1 or 2;
- with the provisos that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent;
- when X is CY1 and Y1 is hydrogen; R1 is NHC(O)R3; R2 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenyl;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is furanyl; the R3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is thienyl; the R3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is R3 phenyl; the phenyl is not substituted at the para position with SO2R4 or SO2NHR4.
- In one embodiment of Formula (I), X is N or CY1. In another embodiment of Formula (I), X is N. In another embodiment of Formula (I), X is CY1.
- In one embodiment of Formula (I), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (I), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (I), X is CY1; and Y1 is Cl. In another embodiment of Formula (I), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (I), Z is CH or N; R1 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R1 is NHC(O)NHR3; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R1 is NHC(O)NH(CH2)mR3x; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R1 is CH2NHC(O)NHR3; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R1 is NHC(O)R3; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R1 is NHC(O)(CH2)nR3; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R1 is C(O)NH(CH2)nR3; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R1 is NHC(O)(CH2)mR3x; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R1 is C(O)NH(CH2)mR3x; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R1 is CH2C(O)NHR3; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R1 is CH2NHC(O)R3; and R2 is hydrogen.
- In one embodiment of Formula (I), Z is CH; R1 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH; R1 is NHC(O)NHR3; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH; R1 is NHC(O)NH(CH2)mR3x; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH; R1 is CH2NHC(O)NHR3; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH; R1 is NHC(O)R3; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH; R1 is NHC(O)(CH2)nR3; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH; R1 is C(O)NH(CH2)nR3; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH; R1 is NHC(O)(CH2)mR3x; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH; R1 is C(O)NH(CH2)mR3x; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH; R1 is CH2C(O)NHR3; and R2 is hydrogen. In another embodiment of Formula (I), Z is CH; R1 is CH2NHC(O)R3; and R2 is hydrogen.
- In one embodiment of Formula (I), Z is N; R1 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3; and R2 is hydrogen. In another embodiment of Formula (I), Z is N; R1 is NHC(O)NHR3; and R2 is hydrogen. In another embodiment of Formula (I), Z is N; R1 is NHC(O)NH(CH2)mR3x; and R2 is hydrogen. In another embodiment of Formula (I), Z is N; R1 is CH2NHC(O)NHR3; and R2 is hydrogen. In another embodiment of Formula (I), Z is N; R1 is NHC(O)R3; and R2 is hydrogen. In another embodiment of Formula (I), Z is N; R1 is NHC(O)(CH2)nR3; and R2 is hydrogen. In another embodiment of Formula (I), Z is N; R1 is C(O)NH(CH2)nR3; and R2 is hydrogen. In another embodiment of Formula (I), Z is N; R1 is NHC(O)(CH2)mR3x; and R2 is hydrogen. In another embodiment of Formula (I), Z is N; R1 is C(O)NH(CH2)mR3x; and R2 is hydrogen. In another embodiment of Formula (I), Z is N; R1 is CH2C(O)NHR3; and R2 is hydrogen. In another embodiment of Formula (I), Z is N; R1 is CH2NHC(O)R3; and R2 is hydrogen.
- In one embodiment of Formula (I), R1 is hydrogen; Z is CR2; and R2 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3. In another embodiment of Formula (I), R1 is hydrogen; Z is CR2; and R2 is NHC(O)NHR3. In another embodiment of Formula (I), R1 is hydrogen; Z is CR2; and R2 is NHC(O)NH(CH2)mR3x. In another embodiment of Formula (I), R1 is hydrogen; Z is CR2; and R2 is CH2NHC(O)NHR3. In another embodiment of Formula (I), R1 is hydrogen; Z is CR2; and R2 is NHC(O)R3. In another embodiment of Formula (I), R1 is hydrogen; Z is CR2; and R2 is NHC(O)(CH2)nR3. In another embodiment of Formula (I), R1 is hydrogen; Z is CR2; and R2 is C(O)NH(CH2)nR3. In another embodiment of Formula (I), R1 is hydrogen; Z is CR2; and R2 is NHC(O)(CH2)mR3x. In another embodiment of Formula (I), R1 is hydrogen; Z is CR2; and R2 is C(O)NH(CH2)mR3x. In another embodiment of Formula (I), R1 is hydrogen; Z is CR2; and R2 is CH2C(O)NHR3. In another embodiment of Formula (I), R1 is hydrogen; Z is CR2; and R2 is CH2NHC(O)R3.
- In one embodiment of Formula (I), m is 4, 5, or 6. In another embodiment of Formula (I), m is 4. In another embodiment of Formula (I), m is 5. In another embodiment of Formula (I), m is 6.
- In one embodiment of Formula (I), n is 1 or 2. In another embodiment of Formula (I), n is 1. In another embodiment of Formula (I), n is 2.
- In one embodiment of Formula (I), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (I), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (I), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (I), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (I), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (I), R3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R3x phenyl and heterocycyl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (I), R3x is heterocyclyl; wherein each R3x heterocycyl is substituted with C(O)R4, or CO(O)R4.
- In one embodiment of Formula (I), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (I), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, and OH.
- In another embodiment of Formula (I), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (I), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (I), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (I), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (I), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (I), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (I), R8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (I), R8 at each occurrence, is independently alkyl.
- In one embodiment of Formula (I), R9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (I), R9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (I), R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (I), R10 at each occurrence, is independently haloalkyl or alkyl.
- In one embodiment of Formula (I), R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (I), R11 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (I)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R1 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3; and CH2NHC(O)R3; and
- Z is CH or N; or
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen F, Cl, Br, and I;
- R1 is hydrogen;
- Z is CR2; and
- R2 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, CH2C(O)NHR3; and CH2NHC(O)R3; and
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I;
- R3x is independently heterocyclyl; wherein each R3x heterocyclyl is substituted with one substituents independently selected from the group consisting of C(O)R4, CO(O)R4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R8, OR8, CNF, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R11, OR11, CO(O)R11, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl;
- R11 at each occurrence, is alkyl;
- m is 4, or 5; and
- n is 1;
- with the provisos that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent;
- when X is CY1 and Y1 is hydrogen; R1 is NHC(O)R3; R2 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenyl;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is furanyl; the R3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is thienyl; the R3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is R3 phenyl; the phenyl is not substituted at the para position with SO2R4 or SO2NHR4.
- Still another embodiment pertains to compounds having Formula (I), which includes Examples 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178, 179, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 236, 237, 238, 239, 240, 241, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 253, 254, 255, 256, 257, 258, 259, 260, 261, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, 288, 289, 290, 291, 292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 302, 303, 304, 305, 306, 307, 308, 309, 310, 311, 312, 313, 314, 315, 316, 317, 318, 319, 320, 321, 322, 323, 324, 325, 326, 327, 328, 329, 330, 331, 332, 333, 334, 335, 336, 337, 338, 339, 340, 341, 342, 343, 344, 345, 346, 347, 348, 349, 350, 351, 352, 353, 354, 355, 356, 357, 358, 359, 360, 361, 362, 363, 364, 365, 366, 367, 368, 369, 370, 371, 372, 373, 374, 375, 376, 377, 378, 379, 380, 381, 382, 383, 384, 385, 386, 387, 388, 389, 390, 391, 392, 393, 394, 395, 396, 397, 398, 399, 400, 401, 402, 403, 404, 405, 406, 407, 408, 409, 410, 411, 412, 413, 414, 415, 416, 417, 418, 419, 420, 421, 422, 423, 424, 425, 426, 427, 428, 429, 430, 431, 432, 433, 434, 435, 436, 437, 438, 439, 440, 441, 442, 443, 444, 445, 446, 447, 448, 449, 450, 451, 452, 453, 454, 455, 456, 457, 458, 459, 460, 461, 462, 463, 464, 465, 466, 467, 468, 469, 470, 471, 472, 473, 474, 475, 476, 477, 478, 479, 480, 481, 482, 483, 484, 485, 486, 487, 488, 489, 490, 491, 492, 493, 494, 495, 496, 497, 498, 499, 500, 501, 502, 503, 504, 505, 506, 507, 508, 509, 510, 511, 512, 513, 514, 515, 516, 517, 518, 519, 520, 521, 522, 523, 524, 525, 526, 527, 528, 529, 530, 531, 532, 533, 534, 535, 536, 537, 538, 539, 540, 541, 542, 543, 544, 545, 546, 547, 548, 549, 550, 551, 552, 553, 554, 555, 556, 557, 558, 559, 560, 561, 562, 563, 564, 565, 566, 567, 568, 569, 570, 571, 572, 573, 574, 575, 576, 577, 578, 579, 580, 580, 581, 582, 584, 585, 586, 587, 588, 589, 590, 591, 592, 593, 594, 595, 596, 597, 598, 599, 600, 601, 602, 603, 604, 605, 606, 607, 608, 609, 610, 611, 612, 613, 614, 615, 616, 617, 618, 619, 620, 621, 622, 623, 624, 625, 626, 627, 628, 629, 630, 631, 632, 633, 634, 635, 636, 637, 638, 639, 640, 641, 642, 643, 644, 645, 646, 647, 648, 649, 650, 651, 652, 653, 654, 655, 656, 657, 658, 659, 660, 661, 662, 663, 664, 665, 666, 667, 668, 669, 670, 671, 672, 673, 674, 675, 676, 677, 678, 679, 680, 681, 682, 683, 684, 685, 686, 687, 688, 689, 690, 691, 692, 693, 694, 695, 696, 697, 698, 699, 700, 701, 702, 703, 704, 705, 706, 707, 708, 709, 710, 711, 712, 713, 714, 715, 716, 717, 718, 719, 720, 721, 722, 723, 724, 725, 726, 727, 728, 729, 730, 731, 732, 733, 734, 735, 736, 737, 738, 739, 740, 741, 742, 743, 744, 745, 746, 747, 748, 749, 750, 751, 752, 753, 754, 755, 756, 757, 758, 759, 760, 761, 762, 763, 764, 765, 766, 767, 768, 769, 770, 771, 772, 773, 774, 775, 776, 777, 778, 779, 780, 781, 782, 783, 784, 785, 786, 787, 788, 789, 790, 791, 792, 793, 794, 795, 796, 797, 798, 799, 800, 801, 802, 803, 804, 805, 806, 807, 808, 809, 810, 811, 812, 813, 814, 815, 816, 817, 818, 819, 820, 821, 822, 823, 824, 825, 826, 827, 828, 829, 830, 831, 832, 833, 834, 835, 836, 837, 838, 839, 840, 841, 842, 843, 844, 845, 846, 847, 848, 849, 850, 851, 852, 853, 854, 855, 856, and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (II)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (I).
- One embodiment pertains to compounds of Formula (II) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl; and
- R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (II), X is N or CY1. In another embodiment of Formula (II), X is N. In another embodiment of Formula (II), X is CY1.
- In one embodiment of Formula (II), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (II), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (II), X is CY1; and Y1 is Cl. In another embodiment of Formula (II), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (II), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (II), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (II), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (II), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (II), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (II), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (II), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, and OH.
- In another embodiment of Formula (II), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (II), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (II), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (II), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (II), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (II), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (II), R8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (II), R8 at each occurrence, is independently alkyl.
- In one embodiment of Formula (II), R9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (II), R9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (II), R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (II), R10 at each occurrence, is independently haloalkyl or alkyl.
- In one embodiment of Formula (II), R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (II), R11 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (II)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R8, OR8, CNF, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R11, OR11, CO(O)R11, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
- R11 at each occurrence, is alkyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (II), which includes Example 2; and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (III)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described in Formula (I) herein.
- One embodiment pertains to compounds of Formula (III) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl; and
- R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (III), X is N or CY1. In another embodiment of Formula (III), X is N. In another embodiment of Formula (III), X is CY1.
- In one embodiment of Formula (III), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (III), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (III), X is CY1; and Y1 is Cl. In another embodiment of Formula (III), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (III), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (III), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (III), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (III), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (III), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (III), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (III), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, and OH.
- In another embodiment of Formula (III), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (III), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (III), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (III), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (III), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (III), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (III), R8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (III), R8 at each occurrence, is independently alkyl.
- In one embodiment of Formula (III), R9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (III), R9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (III), R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (III), R10 at each occurrence, is independently haloalkyl or alkyl.
- In one embodiment of Formula (III), R1 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (III), R1 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (III)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R8, OR8, CNF, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R11, OR11, CO(O)R11, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
- R11 at each occurrence, is alkyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (III), which includes Examples 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 89, 106, 109, 110, 111, 112, 113, 396, and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (IV)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (I).
- One embodiment pertains to compounds of Formula (IV) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl; and
- R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (IV), X is N or CY1. In another embodiment of Formula (IV), X is N. In another embodiment of Formula (IV), X is CY1.
- In one embodiment of Formula (IV), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IV), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IV), X is CY1; and Y1 is Cl. In another embodiment of Formula (IV), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (IV), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IV), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IV), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IV), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IV), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IV), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IV), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, and OH.
- In another embodiment of Formula (IV), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IV), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (IV), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IV), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (IV), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IV), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (IV), R8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IV), R8 at each occurrence, is independently alkyl.
- In one embodiment of Formula (IV), R9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (IV), R9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (IV), R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IV), R10 at each occurrence, is independently haloalkyl or alkyl.
- In one embodiment of Formula (IV), R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IV), R11 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IV)
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I; R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R8, OR8, CNF, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R11, OR11, CO(O)R11, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
- R11 at each occurrence, is alkyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (IV), which includes Examples 118, 216, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 243, 280, 281, 282, 283, 284, 285, 286, 287, 288, 289, 290, 291, 302, 303, 306, 307, 328, 329, 330, 331, 332, 333, 334, 335, 336, 337, 338, 364, 366, 379, 380, 381, 382, 383, 384, 385, 386, 387, 388, 389, 390, 391, 392, 404, 407, 424, 425, 426, 427, 428, 429, 430, 431, 432, 433, 434, 435, 438, 439, 442, 443, 444, 445, 446, 447, 448, 449, 450, 451, 452, 453, 454, 455, 456, 457, 458, 459, 460, 461, 486, 487, 496, 564, 565, 673, 674, 675, 689, 690, 691, 692, 693, 694, 695, 696, 709, 710, 711, 712, 713, 714, 715, 716, 719, 720, 721, 722, 723, 724, 725, 726, 727, 728, 729, 730, and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (V)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (I).
- One embodiment pertains to compounds of Formula (V) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl;
- R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (V), X is N or CY1. In another embodiment of Formula (V), X is N. In another embodiment of Formula (V), X is CY1.
- In one embodiment of Formula (V), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (V), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (V), X is CY1; and Y1 is Cl. In another embodiment of Formula (V), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (V), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (V), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (V), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (V), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (V), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (V), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (V), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, and OH.
- In another embodiment of Formula (V), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (V), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (V), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (V), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (V), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (V), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (V), R8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (V), R8 at each occurrence, is independently alkyl.
- In one embodiment of Formula (V), R9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (V), R9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (V), R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (V), R10 at each occurrence, is independently haloalkyl or alkyl.
- In one embodiment of Formula (V), R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (V), R11 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (V)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R8, OR8, CNF, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R11, OR11, CO(O)R11, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
- R11 at each occurrence, is alkyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (V), which include Examples 59, 60, 274, 275, 276, 277, 278, 279, 360, 362, and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (VI)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (I).
- One embodiment pertains to compounds of Formula (VI) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl; and
- R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (VI), X is N or CY1. In another embodiment of Formula (VI), X is N. In another embodiment of Formula (VI), X is CY1.
- In one embodiment of Formula (VI), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VI), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VI), X is CY1; and Y1 is Cl. In another embodiment of Formula (VI), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (VI), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VI), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VI), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VI), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (VI), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VI), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VI), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, and OH.
- In another embodiment of Formula (VI), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VI), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (VI), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VI), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (VI), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VI), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (VI), R8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VI), R8 at each occurrence, is independently alkyl.
- In one embodiment of Formula (VI), R9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (VI), R9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (VI), R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VI), R10 at each occurrence, is independently haloalkyl or alkyl.
- In one embodiment of Formula (VI), R10 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VI), R10 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VI)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R8, OR8, CNF, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R11, OR11, CO(O)R11, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
- R11 at each occurrence, is alkyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (VI), which includes Examples 57, 117, 121, 138, 174, 181, 182, 185, 187, 188, 192, 193, 194, 195, 196, 197, 198, 199, 202, 203, 204, 205, 207, 208, 209, 210, 211, 212, 213, 214, 217, 218, 230, 231, 232, 233, 234, 235, 236, 237, 238, 239, 241, 242, 244, 245, 246, 247, 248, 249, 250, 251, 252, 253, 254, 255, 256, 257, 258, 259, 260, 261, 262, 263, 264, 265, 266, 267, 268, 269, 271, 272, 273, 292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 304, 305, 308, 309, 310, 311, 312, 313, 315, 316, 317, 318, 319, 320, 321, 324, 325, 326, 327, 339, 340, 341, 342, 343, 344, 345, 346, 347, 348, 349, 350, 351, 352, 353, 354, 355, 356, 357, 361, 363, 365, 367, 368, 369, 370, 371, 372, 373, 374, 375, 376, 377, 378, 393, 394, 395, 397, 399, 400, 401, 402, 403, 405, 406, 408, 409, 410, 411, 412, 413, 414, 415, 416, 417, 418, 419, 420, 421, 422, 423, 436, 437, 440, 441, 463, 464, 465, 466, 467, 468, 469, 470, 471, 472, 473, 474, 475, 476, 477, 478, 479, 480, 481, 482, 483, 484, 485, 488, 489, 490, 492, 493, 494, 495, 497, 498, 499, 500, 501, 502, 503, 504, 505, 506, 507, 508, 509, 510, 511, 512, 513, 514, 515, 516, 517, 518, 519, 520, 521, 522, 523, 524, 525, 526, 527, 528, 529, 530, 531, 532, 533, 534, 535, 536, 537, 538, 539, 540, 541, 542, 543, 544, 545, 546, 547, 548, 549, 550, 551, 552, 553, 554, 555, 556, 557, 558, 559, 560, 561, 562, 563, 566, 567, 568, 569, 570, 571, 572, 573, 574, 575, 576, 577, 578, 579, 580, 581, 582, 583, 584, 585, 586, 587, 588, 589, 590, 591, 592, 593, 594, 595, 596, 597, 598, 599, 600, 601, 602, 603, 604, 605, 606, 607, 608, 609, 610, 611, 612, 613, 614, 615, 616, 617, 618, 619, 620, 623, 624, 625, 626, 627, 628, 629, 630, 631, 632, 633, 634, 635, 636, 637, 638, 639, 640, 641, 642, 643, 644, 645, 646, 647, 648, 649, 650, 651, 652, 653, 654, 655, 656, 657, 658, 659, 660, 661, 662, 663, 664, 665, 666, 667, 668, 669, 670, 671, 672, 677, 682, 683, 684, 685, 686, 687, 688, 697, 698, 699, 700, 701, 702, 703, 704, 705, 706, 707, 708, 717, 718, 731, 732, 733, 734, 735, 736, 737, 738, 740, 741, 742, 743, 744, 745, 746, 747, 748, 749, 750, 751, 752, 753, 755, 756, 757, 758, 759, 760, 761, 762, 763, 764, 765, 766, 767, 768, 769, 770, 771, 772, 773, 774, 775, 776, 777, 778, 779, 780, 781, 782, 783, 784, 785, 786, 787, 788, 789, 790, 791, 792, 793, 794, 795, 796, 797, 798, 799, 800, 801, 802, 803, 804, 805, 806, 807, 808, 809, 818, 821, 823, 824, 825, and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (VII)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (I).
- One embodiment pertains to compounds of Formula (VII) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl; and
- R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (VII), X is N or CY1. In another embodiment of Formula (VII), X is N. In another embodiment of Formula (VII), X is CY1.
- In one embodiment of Formula (VII), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VII), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VII), X is CY1; and Y1 is Cl. In another embodiment of Formula (VII), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (VII), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VII), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VII), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VII), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (VII), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VII), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VII), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, and OH.
- In another embodiment of Formula (VII), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VII), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (VII), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VII), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (VII), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VII), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (VII), R8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VII), R8 at each occurrence, is independently alkyl.
- In one embodiment of Formula (VII), R9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (VII), R9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (VII), R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VII), R10 at each occurrence, is independently haloalkyl or alkyl.
- In one embodiment of Formula (VII), R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VII), R11 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VII)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R8, OR8, CNF, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R11, OR11, CO(O)R11, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
- R11 at each occurrence, is alkyl;
- with the proviso that when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (VII), which includes Examples 52, 55, 56, 61, 75, 77, 78, 79, 80, 81, 82, 83, 85, 86, 87, 88, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 108, 114, 115, 116, 119, 120, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 175, 176, 177, 178, 179, 180, 183, 184, 186, 189, 190, 191, 200, 201, 206, 215, 219, 240, 358, 359, 398, 462, 621, 622, 676, 810, 820, 822, 831, 832, 833, 834, 835, 836, 842, 843, 844, 845, 846, 847, 848, 849, 850, 851, 852, 853, and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (VIII)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (I).
- One embodiment pertains to compounds of Formula (VIII) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl; and
- R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (VIII), X is N or CY1. In another embodiment of Formula (VIII), X is N. In another embodiment of Formula (VIII), X is CY1.
- In one embodiment of Formula (VIII), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VIII), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VIII), X is CY1; and Y1 is Cl. In another embodiment of Formula (VIII), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (VIII), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIII), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VIII), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VIII), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (VIII), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VIII), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIII), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, and OH.
- In another embodiment of Formula (VIII), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIII), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (VIII), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIII), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (VIII), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIII), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (VIII), R8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIII), R8 at each occurrence, is independently alkyl.
- In one embodiment of Formula (VIII), R9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (VIII), R9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (VIII), R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIII), R10 at each occurrence, is independently haloalkyl or alkyl.
- In one embodiment of Formula (VIII), R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIII), R11 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VIII)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R8, OR8, CNF, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R11, OR11, CO(O)R11, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
- R11 at each occurrence, is alkyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (VIII), which includes Example 322, and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (IX)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (I).
- One embodiment pertains to compounds of Formula (IX) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl; and
- R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- with the provisos that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent; and
- when X is CY1 and Y1 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenyl.
- In one embodiment of Formula (IX), X is N or CY1. In another embodiment of Formula (IX), X is N. In another embodiment of Formula (IX), X is CY1.
- In one embodiment of Formula (IX), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IX), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IX), X is CY1; and Y1 is Cl. In another embodiment of Formula (IX), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (IX), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IX), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IX), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IX), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IX), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IX), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IX), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, and OH.
- In another embodiment of Formula (IX), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IX), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (IX), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR11C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IX), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (IX), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IX), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (IX), R8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IX), R8 at each occurrence, is independently alkyl.
- In one embodiment of Formula (IX), R9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (IX), R9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (IX), R10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IX), R10 at each occurrence, is independently haloalkyl or alkyl.
- In one embodiment of Formula (IX), R11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IX), R11 at each occurrence, is independently alkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IX)
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R8, OR8, CNF, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R11, OR11, CO(O)R11, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
- R11 at each occurrence, is alkyl;
- with the provisos that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent; and
- when X is CY1 and Y1 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenyl.
- Still another embodiment pertains to compounds having Formula (IX), which includes Examples 53, 54, 76, 314, 323, 491, and pharmaceutically acceptable salts thereof.
- One embodiment, therefore, pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IA)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R1 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3; and
- Z is CH, C—F, C—Cl, C—Br, C—I or N; or
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R1 is hydrogen, F, Cl, Br, or I;
- Z is CR2; and
- R2 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3; and
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R3x phenyl and heterocyclyl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I;
- R11 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
- m is 4, 5, or 6; and
- n is 1 or 2;
- with the provisos that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent;
- when X is CY1 and Y1 is hydrogen; R1 is NHC(O)R3; R2 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenyl;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is furanyl; the R3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is thienyl; the R3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is R3 phenyl; the phenyl is not substituted at the para position with SO2R4 or SO2NHR4.
- In one embodiment of Formula (IA), X is N or CY1. In another embodiment of Formula (IA), X is N. In another embodiment of Formula (IA), X is CY1.
- In one embodiment of Formula (IA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IA), X is CY1; and Y1 is Cl. In another embodiment of Formula (IA), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (IA), Z is CH, C—F, C—Cl, C—Br, C—I or N; and R1 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3. In another embodiment of Formula (IA), Z is CH or N; and R1 is NHC(O)NHR3. In another embodiment of Formula (IA), Z is CH or N; and R1 is NHC(O)NH(CH2)mR3x. In another embodiment of Formula (IA), Z is CH or N; and R1 is CH2NHC(O)NHR3. In another embodiment of Formula (IA), Z is CH or N; and R1 is NHC(O)R3. In another embodiment of Formula (IA), Z is CH or N; and R1 is NHC(O)(CH2)nR3. In another embodiment of Formula (IA), Z is CH or N; and R1 is C(O)NH(CH2)nR3. In another embodiment of Formula (IA), Z is CH or N; and R1 is NHC(O)(CH2)mR3x. In another embodiment of Formula (IA), Z is CH or N; and R1 is C(O)NH(CH2)mR3x. In another embodiment of Formula (IA), Z is CH or N; and R1 is CH2C(O)NHR3. In another embodiment of Formula (IA), Z is CH or N; and R1 is CH2NHC(O)R3.
- In one embodiment of Formula (IA), Z is CH; and R1 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3. In another embodiment of Formula (IA), Z is CH; and R1 is NHC(O)NHR3. In another embodiment of Formula (IA), Z is CH; and R1 is NHC(O)NH(CH2)mR3x. In another embodiment of Formula (IA), Z is CH; and R1 is CH2NHC(O)NHR3. In another embodiment of Formula (IA), Z is CH; and R1 is NHC(O)R3.
- In another embodiment of Formula (IA), Z is CH; and R1 is NHC(O)(CH2)nR3. In another embodiment of Formula (IA), Z is CH; and R1 is C(O)NH(CH2)nR3. In another embodiment of Formula (IA), Z is CH; and R1 is NHC(O)(CH2)mR3x. In another embodiment of Formula (IA), Z is CH; and R1 is C(O)NH(CH2)mR3x. In another embodiment of Formula (IA), Z is CH; and R1 is CH2C(O)NHR3. In another embodiment of Formula (IA), Z is CH; and R1 is CH2NHC(O)R3.
- In one embodiment of Formula (IA), Z is N; and R1 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3. In another embodiment of Formula (IA), Z is N; and R1 is NHC(O)NHR3. In another embodiment of Formula (IA), Z is N; and R1 is NHC(O)NH(CH2)mR3x. In another embodiment of Formula (IA), Z is N; and R1 is CH2NHC(O)NHR3. In another embodiment of Formula (IA), Z is N; and R1 is NHC(O)R3.
- In another embodiment of Formula (IA), Z is N; and R1 is NHC(O)(CH2)nR3. In another embodiment of Formula (IA), Z is N; and R1 is C(O)NH(CH2)nR3. In another embodiment of Formula (IA), Z is N; and R1 is NHC(O)(CH2)mR3x. In another embodiment of Formula (IA), Z is N; and R1 is C(O)NH(CH2)mR3x. In another embodiment of Formula (IA), Z is N; and R1 is CH2C(O)NHR3. In another embodiment of Formula (IA), Z is N; and R1 is CH2NHC(O)R3.
- In one embodiment of Formula (IA), R1 is hydrogen; Z is CR2; and R2 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3. In another embodiment of Formula (IA), R1 is hydrogen; Z is CR2; and R2 is NHC(O)NHR3. In another embodiment of Formula (IA), R1 is hydrogen; Z is CR2; and R2 is NHC(O)NH(CH2)mR3x. In another embodiment of Formula (IA), R1 is hydrogen; Z is CR2; and R2 is CH2NHC(O)NHR3. In another embodiment of Formula (IA), R1 is hydrogen; Z is CR2; and R2 is NHC(O)R3. In another embodiment of Formula (IA), R1 is hydrogen; Z is CR2; and R2 is NHC(O)(CH2)nR3. In another embodiment of Formula (IA), R1 is hydrogen; Z is CR2; and R2 is C(O)NH(CH2)nR3.
- In another embodiment of Formula (IA), R1 is hydrogen; Z is CR2; and R2 is NHC(O)(CH2)mR3x. In another embodiment of Formula (IA), R1 is hydrogen; Z is CR2; and R2 is C(O)NH(CH2)mR3x. In another embodiment of Formula (IA), R1 is hydrogen; Z is CR2; and R2 is CH2C(O)NHR3. In another embodiment of Formula (IA), R1 is hydrogen; Z is CR2; and R2 is CH2NHC(O)R3.
- In one embodiment of Formula (IA), m is 4, 5, or 6. In another embodiment of Formula (IA), m is 4. In another embodiment of Formula (IA), m is 5. In another embodiment of Formula (IA), m is 6.
- In one embodiment of Formula (IA), n is 1 or 2. In another embodiment of Formula (IA), n is 1. In another embodiment of Formula (IA), n is 2.
- In one embodiment of Formula (IA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, SO2R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IA), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, SO2R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IA), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IA), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IA), R3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R3x phenyl and heterocycyl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IA), R3x is heterocyclyl; wherein each R3x heterocycyl is substituted with C(O)R4, or CO(O)R4.
- In one embodiment of Formula (IA), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IA), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (IA), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IA), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (IA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (IA), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IA), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (IA), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IA), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (IA), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (IA), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, CN, F, and Cl.
- In one embodiment of Formula (IA), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (IA), R10 at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (IA), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IA), R11, at each occurrence, is independently alkyl.
- In another embodiment of Formula (IA), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IA)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R1 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3; and
- Z is CH, C—F, or N; or
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, and Cl;
- R1 is hydrogen;
- Z is CR2; and
- R2 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, CH2C(O)NHR3, and CH2NHC(O)R3; and
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R3x is heterocyclyl; wherein the R3x heterocyclyl is substituted with one, two, three or four substituents independently selected from the group consisting of C(O)R4, CO(O)R4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, CN, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F;
- R11 at each occurrence, is independently cycloalkyl or alkyl;
- m is 4, or 5; and
- n is 1;
- with the provisos that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent;
- when X is CY1 and Y1 is hydrogen; R1 is NHC(O)R3; R2 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenyl;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is furanyl; the R3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is thienyl; the R3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is R3 phenyl; the phenyl is not substituted at the para position with SO2R4 or SO2NHR4.
- Still another embodiment pertains to compounds having Formula (IA), which includes Examples 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178, 179, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 236, 237, 238, 239, 240, 241, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 253, 254, 255, 256, 257, 258, 259, 260, 261, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, 288, 289, 290, 291, 292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 302, 303, 304, 305, 306, 307, 308, 309, 310, 311, 312, 313, 314, 315, 316, 317, 318, 319, 320, 321, 322, 323, 324, 325, 326, 327, 328, 329, 330, 331, 332, 333, 334, 335, 336, 337, 338, 339, 340, 341, 342, 343, 344, 345, 346, 347, 348, 349, 350, 351, 352, 353, 354, 355, 356, 357, 358, 359, 360, 361, 362, 363, 364, 365, 366, 367, 368, 369, 370, 371, 372, 373, 374, 375, 376, 377, 378, 379, 380, 381, 382, 383, 384, 385, 386, 387, 388, 389, 390, 391, 392, 393, 394, 395, 396, 397, 398, 399, 400, 401, 402, 403, 404, 405, 406, 407, 408, 409, 410, 411, 412, 413, 414, 415, 416, 417, 418, 419, 420, 421, 422, 423, 424, 425, 426, 427, 428, 429, 430, 431, 432, 433, 434, 435, 436, 437, 438, 439, 440, 441, 442, 443, 444, 445, 446, 447, 448, 449, 450, 451, 452, 453, 454, 455, 456, 457, 458, 459, 460, 461, 462, 463, 464, 465, 466, 467, 468, 469, 470, 471, 472, 473, 474, 475, 476, 477, 478, 479, 480, 481, 482, 483, 484, 485, 486, 487, 488, 489, 490, 491, 492, 493, 494, 495, 496, 497, 498, 499, 500, 501, 502, 503, 504, 505, 506, 507, 508, 509, 510, 511, 512, 513, 514, 515, 516, 517, 518, 519, 520, 521, 522, 523, 524, 525, 526, 527, 528, 529, 530, 531, 532, 533, 534, 535, 536, 537, 538, 539, 540, 541, 542, 543, 544, 545, 546, 547, 548, 549, 550, 551, 552, 553, 554, 555, 556, 557, 558, 559, 560, 561, 562, 563, 564, 565, 566, 567, 568, 569, 570, 571, 572, 573, 574, 575, 576, 577, 578, 579, 580, 581, 582, 583, 584, 585, 586, 587, 588, 589, 590, 591, 592, 593, 594, 595, 596, 597, 598, 599, 600, 601, 602, 603, 604, 605, 606, 607, 608, 609, 610, 611, 612, 613, 614, 615, 616, 617, 618, 619, 620, 621, 622, 623, 624, 625, 626, 627, 628, 629, 630, 631, 632, 633, 634, 635, 636, 637, 638, 639, 640, 641, 642, 643, 644, 645, 646, 647, 648, 649, 650, 651, 652, 653, 654, 655, 656, 657, 658, 659, 660, 661, 662, 663, 664, 665, 666, 667, 668, 669, 670, 671, 672, 673, 674, 675, 676, 677, 678, 679, 680, 681, 682, 683, 684, 685, 686, 687, 688, 689, 690, 691, 692, 693, 694, 695, 696, 697, 698, 699, 700, 701, 702, 703, 704, 705, 706, 707, 708, 709, 710, 711, 712, 713, 714, 715, 716, 717, 718, 719, 720, 721, 722, 723, 724, 725, 726, 727, 728, 729, 730, 731, 732, 733, 734, 735, 736, 737, 738, 739, 740, 741, 742, 743, 744, 745, 746, 747, 748, 749, 750, 751, 752, 753, 754, 755, 756, 757, 758, 759, 760, 761, 762, 763, 764, 765, 766, 767, 768, 769, 770, 771, 772, 773, 774, 775, 776, 777, 778, 779, 780, 781, 782, 783, 784, 785, 786, 787, 788, 789, 790, 791, 792, 793, 794, 795, 796, 797, 798, 799, 800, 801, 802, 803, 804, 805, 806, 807, 808, 809, 810, 811, 812, 813, 814, 815, 816, 817, 818, 819, 820, 821, 822, 823, 824, 825, 826, 827, 828, 829, 830, 831, 832, 833, 834, 835, 836, 837, 838, 839, 840, 841, 842, 843, 844, 845, 846, 847, 848, 849, 850, 851, 852, 853, 854, 855, 856, 857, 858, 859, 860, 861, 862, 863, 864, 865, 866, 867, 868, 869, 870, 871, 872, 873, 874, 875, 876, 877, 878, 879, 880, 881, 882, 883, 884, 885, 886, 887, 888, 889, 890, 891, 892, 893, 894, 895, 896, 897, 898, 899, 900, 901, 902, 903, 904, 905, 906, 907, 908, 909, 910, 911, 912, 913, 914, 915, 916, 917, 918, 919, 920, 921, 922, 923, 924, 925, 926, 927, 928, 929, 930, 931, 932, 933, 934, 935, 936, 937, 938, 939, 940, 941, 942, 943, 944, 945, 946, 947, 948, 949, 950, 951, 952, 953, 954, 955, 956, 957, 958, 959, 960, 961, 962, 963, 964, 965, 966, 967, 968, 969, 970, 971, 972, 973, 974, 975, 976, 977, 978, 979, 980, 981, 982, 983, 984, 985, 986, 987, 988, 989, 990, 991, 992, 993, 994, 995, 996, 997, 998, 999, 1000, 1001, 1002, 1003, 1004, 1005, 1006, 1007, 1008, 1009, 1010, 1011, 1012, 1013, 1014, 1015, 1016, 1017, 1018, 1019, 1020, 1021, 1022, 1023, 1024, 1025, 1026, 1027, 1028, 1029, 1030, 1031, 1032, 1033, 1034, 1035, 1036, 1037, 1038, 1039, 1040, 1041, 1042, 1043, 1044, 1045, 1046, 1047, 1048, 1049, 1050, 1051, 1052, 1053, 1054, 1055, 1056, 1057, 1058, 1059, 1060, 1061, 1062, 1063, 1064, 1065, 1066, 1067, 1068, 1069, 1070, 1071, 1072, 1073, 1074, 1075, 1076, 1077, 1078, 1079, 1080, 1081, 1082, 1083, 1084, 1085, 1086, 1087, 1088, 1089, 1090, 1091, 1092, 1093, 1094, 1095, 1096, 1097, 1098, 1099, 1100, 1101, 1102, 1103, 1104, 1105, 1106, 1107, 1108, 1109, 1110, 1111, 1112, 1113, 1114, 1115, 1116, 1117, 1118, 1119, 1120, 1121, 1122, 1123, 1124, 1125, 1126, 1127, 1128, 1129, 1130, 1131, 1132, 1133, 1134, 1135, 1136, 1137, 1138, 1139, 1140, 1141, 1142, 1143, 1144, 1145, 1146, 1147, 1148, 1149, 1150, 1151, 1152, 1153, 437, 508, 513, 516, 527, 529, 699, 915, 919, 923, 924, 925, 927, 934, 937, 985, 996, 999, 1009, 1095, and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (IIA)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (IA).
- One embodiment pertains to compounds of Formula (IIA) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (IIA), X is N or CY1. In another embodiment of Formula (IIA), X is N. In another embodiment of Formula (IIA), X is CY1.
- In one embodiment of Formula (IIA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IIA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IIA), X is CY1; and Y1 is Cl. In another embodiment of Formula (IIA), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (IIA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IIA), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IIA), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IIA), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IIA), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIA), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (IIA), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIA), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (IIA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (IIA), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIA), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (IIA), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IIA), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (IIA), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (IIA), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (IIA), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (IIA), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (IIA), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IIA), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (IIA), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IIA)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (IIA), which includes Example 2; and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (IIIA)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described in Formula (IA) herein.
- One embodiment pertains to compounds of Formula (IIIA) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (IIIA), X is N or CY1. In another embodiment of Formula (IIIA), X is N. In another embodiment of Formula (IIIA), X is CY1.
- In one embodiment of Formula (IIIA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IIIA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IIIA), X is CY1; and Y1 is Cl. In another embodiment of Formula (IIIA), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (IIIA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIIA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IIIA), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IIIA), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IIIA), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IIIA), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIIA), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (IIIA), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIIA), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (IIIA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIIA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (IIIA), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIIA), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (IIIA), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IIIA), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (IIIA), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (IIIA), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (IIIA), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (IIIA), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (IIIA), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IIIA), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (IIIA), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IIIA)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (IIIA), which includes 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 89, 106, 109, 110, 111, 112, 113, 396, and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (IVA)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (IA).
- One embodiment pertains to compounds of Formula (IVA) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (IVA), X is N or CY1. In another embodiment of Formula (IVA), X is N. In another embodiment of Formula (IVA), X is CY1.
- In one embodiment of Formula (IVA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IVA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IVA), X is CY1; and Y1 is Cl. In another embodiment of Formula (IVA), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (IVA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IVA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IVA), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IVA), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IVA), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IVA), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IVA), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (IVA), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IVA), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (IVA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IVA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (IVA), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IVA), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (IVA), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IVA), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (IVA), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (IVA), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (IVA), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (IVA), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (IVA), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IVA), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (IVA), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IVA)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (IVA), which includes Examples 118, 216, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 243, 280, 281, 282, 283, 284, 285, 286, 287, 288, 289, 290, 291, 302, 303, 306, 307, 328, 329, 330, 331, 332, 333, 334, 335, 336, 337, 338, 364, 366, 379, 380, 381, 382, 383, 384, 385, 386, 387, 388, 389, 390, 391, 392, 404, 407, 424, 425, 426, 427, 428, 429, 430, 431, 432, 433, 434, 435, 438, 439, 442, 443, 444, 445, 446, 447, 448, 449, 450, 451, 452, 453, 454, 455, 456, 457, 458, 459, 460, 461, 486, 487, 496, 564, 565, 673, 674, 675, 689, 690, 691, 692, 693, 694, 695, 696, 709, 710, 711, 712, 713, 714, 715, 716, 719, 720, 721, 722, 723, 724, 725, 726, 727, 728, 729, 730, 904, 912, 938, 939, 940, 941, 942, 943, 944, 945, 946, 947, 948, 949, 950, 951, 952, 953, 954, 955, 956, 957, 1011, 1012, 1013, 1014, 1015, 1016, 1017, 1018, 1019, 1020, 1021, 1022, 1023, 1024, 1025, 1026, 1027, 1028, 1029, 1030, 1031, 1032, 1033, 1034, 1035, 1036, 1037, 1038, 1039, 1040, 1041, 1042, 1043, 1044, 1045, 1046, 1047, 1048, 1049, 1050, 1051, 1052, 1053, 1054, 1055, 1056, 1057, 1058, 1059, 1060, 1065, 1066, 1069, 1070, 1071, 1072, 1073, 1074, 1075, 1076, 1078, 1121, 1122, 1123, 1124, 1125, 1126, 1127, 1128, 1129, 1130, 1131, 1132, 1133, 1134, 1135, 1136, 1137, 1138, 1139, 1140, 1141, 1142, 1143, 1144, 1145, 1146, 1147, 1148, 1149, 1150, 1151, 1152, 1153, and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (VA)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (IA).
- One embodiment pertains to compounds of Formula (VA) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R1, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (VA), X is N or CY1. In another embodiment of Formula (VA), X is N. In another embodiment of Formula (VA), X is CY1.
- In one embodiment of Formula (VA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VA), X is CY1; and Y1 is Cl. In another embodiment of Formula (VA), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (VA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VA), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VA), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (VA), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VA), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VA), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (VA), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VA), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (VA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (VA), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VA), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (VA), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VA), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (VA), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (VA), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (VA), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (VA), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (VA), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VA), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (VA), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VA)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (VA), which includes 59, 60, 274, 275, 276, 277, 278, 279, 360, 362, and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (VIA)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (IA).
- One embodiment pertains to compounds of Formula (VIA) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (VIA), X is N or CY1. In another embodiment of Formula (VIA), X is N. In another embodiment of Formula (VIA), X is CY1.
- In one embodiment of Formula (VIA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VIA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VIA), X is CY1; and Y1 is Cl. In another embodiment of Formula (VIA), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (VIA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VIA), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VIA), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (VIA), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VIA), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIA), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (VIA), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIA), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (VIA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (VIA), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIA), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (VIA), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIA), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (VIA), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (VIA), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (VIA), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (VIA), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (VIA), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIA), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (VIA), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VIA)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (VIA), which includes Examples 57, 117, 121, 138, 174, 181, 182, 185, 187, 188, 192, 193, 194, 195, 196, 197, 198, 199, 202, 203, 204, 205, 207, 208, 209, 210, 211, 212, 213, 214, 217, 218, 230, 231, 232, 233, 234, 235, 236, 237, 238, 239, 241, 242, 244, 245, 246, 247, 248, 249, 250, 251, 252, 253, 254, 255, 256, 257, 258, 259, 260, 261, 262, 263, 264, 265, 266, 267, 268, 269, 271, 272, 273, 292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 304, 305, 308, 309, 310, 311, 312, 313, 315, 316, 317, 318, 319, 320, 321, 324, 325, 326, 327, 339, 340, 341, 342, 343, 344, 345, 346, 347, 348, 349, 350, 351, 352, 353, 354, 355, 356, 357, 361, 363, 365, 367, 368, 369, 370, 371, 372, 373, 374, 375, 376, 377, 378, 393, 394, 395, 397, 399, 400, 401, 402, 403, 405, 406, 408, 409, 410, 411, 412, 413, 414, 415, 416, 417, 418, 419, 420, 421, 422, 423, 436, 437, 440, 441, 463, 464, 465, 466, 467, 468, 469, 470, 471, 472, 473, 474, 475, 476, 477, 478, 479, 480, 481, 482, 483, 484, 485, 488, 489, 490, 492, 493, 494, 495, 497, 498, 499, 500, 501, 502, 503, 504, 505, 506, 507, 508, 509, 510, 511, 512, 513, 514, 515, 516, 517, 518, 519, 520, 521, 522, 523, 524, 525, 526, 527, 528, 529, 530, 531, 532, 533, 534, 535, 536, 537, 538, 539, 540, 541, 542, 543, 544, 545, 546, 547, 548, 549, 550, 551, 552, 553, 554, 555, 556, 557, 558, 559, 560, 561, 562, 563, 566, 567, 568, 569, 570, 571, 572, 573, 574, 575, 576, 577, 578, 579, 580, 581, 582, 583, 584, 585, 586, 587, 588, 589, 590, 591, 592, 593, 594, 595, 596, 597, 598, 599, 600, 601, 602, 603, 604, 605, 606, 607, 608, 609, 610, 611, 612, 613, 614, 615, 616, 617, 618, 619, 620, 623, 624, 625, 626, 627, 628, 629, 630, 631, 632, 633, 634, 635, 636, 637, 638, 639, 640, 641, 642, 643, 644, 645, 646, 647, 648, 649, 650, 651, 652, 653, 654, 655, 656, 657, 658, 659, 660, 661, 662, 663, 664, 665, 666, 667, 668, 669, 670, 671, 672, 677, 682, 683, 684, 685, 686, 687, 688, 697, 698, 699, 700, 701, 702, 703, 704, 705, 706, 707, 708, 717, 718, 731, 732, 733, 734, 735, 736, 737, 738, 740, 741, 742, 743, 744, 745, 746, 747, 748, 749, 750, 751, 752, 753, 755, 756, 757, 758, 759, 760, 761, 762, 763, 764, 765, 766, 767, 768, 769, 770, 771, 772, 773, 774, 775, 776, 777, 778, 779, 780, 781, 782, 783, 784, 785, 786, 787, 788, 789, 790, 791, 792, 793, 794, 795, 796, 797, 798, 799, 800, 801, 802, 803, 804, 805, 806, 807, 808, 809, 818, 821, 823, 824, 825, 857, 867, 868, 869, 870, 871, 872, 873, 874, 875, 876, 877, 878, 879, 880, 881, 883, 884, 885, 886, 887, 888, 889, 890, 891, 892, 893, 895, 896, 899, 906, 907, 909, 910, 913, 914, 915, 916, 917, 918, 919, 920, 921, 922, 923, 924, 925, 926, 927, 928, 929, 930, 931, 932, 933, 934, 935, 936, 937, 958, 959, 960, 961, 962, 963, 964, 965, 966, 967, 968, 969, 970, 971, 972, 973, 974, 975, 976, 977, 978, 979, 980, 981, 982, 983, 984, 985, 986, 987, 988, 989, 990, 991, 992, 993, 994, 995, 996, 997, 998, 999, 1000, 1001, 1002, 1003, 1004, 1005, 1006, 1007, 1008, 1009, 1010, 1061, 1062, 1063, 1064, 1068, 1077, 1082, 1083, 1084, 1085, 1086, 1087, 1088, 1089, 1090, 1091, 1092, 1093, 1094, 1095, 1096, 1097, 1098, 1099, 1100, 1101, 1102, 1103, 1104, 1105, 1106, 1107, 1108, 1109, 1110, 1111, 1112, 1113, 1114, 1115, 1116, 1117, 1118, 1119, 1120, and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (VIIA)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (IA).
- One embodiment pertains to compounds of Formula (VIIA) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (VIIA), X is N or CY1. In another embodiment of Formula (VIIA), X is N. In another embodiment of Formula (VIIA), X is CY1.
- In one embodiment of Formula (VIIA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VIIA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VIIA), X is CY1; and Y1 is Cl. In another embodiment of Formula (VIIA), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (VIIA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VIIA), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VIIA), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (VIIA), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VIIA), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIA), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (VIIA), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIA), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (VIIA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (VIIA), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIA), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (VIIA), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIIA), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (VIIA), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIA), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (VIIA), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (VIIA), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (VIIA), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIIA), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (VIIA), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VIIA)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (VIIA), which includes Examples 52, 55, 56, 61, 75, 77, 78, 79, 80, 81, 82, 83, 85, 86, 87, 88, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 108, 114, 115, 116, 119, 120, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 175, 176, 177, 178, 179, 180, 183, 184, 186, 189, 190, 191, 200, 201, 206, 215, 219, 240, 358, 359, 398, 462, 621, 622, 676, 810, 820, 822, 831, 832, 833, 834, 835, 836, 842, 843, 844, 845, 846, 847, 848, 849, 850, 851, 852, 853, 859, 860, 882, 898, and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (VIIIA)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (I).
- One embodiment pertains to compounds of Formula (VIIIA) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (VIIIA), X is N or CY1. In another embodiment of Formula (VIIIA), X is N. In another embodiment of Formula (VIIIA), X is CY1.
- In one embodiment of Formula (VIIIA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VIIIA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VIIIA), X is CY1; and Y1 is Cl. In another embodiment of Formula (VIIIA), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (VIIIA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIIA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VIIIA), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VIIIA), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (VIIIA), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VIIIA), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIIA), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (VIIIA), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIIA), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (VIIIA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIIA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (VIIIA), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIIA), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (VIIIA), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIIIA), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (VIIIA), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIIA), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (VIIIA), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (VIIIA), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (VIIIA), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIIIA), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (VIIIA), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VIIIA)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (VIIIA), which includes Examples 322; and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (IXA)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (I).
- One embodiment pertains to compounds of Formula (IX) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR1C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
- with the provisos that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent; and
- when X is CY1 and Y1 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenyl.
- In one embodiment of Formula (IXA), X is N or CY1. In another embodiment of Formula (IXA), X is N. In another embodiment of Formula (IXA), X is CY1.
- In one embodiment of Formula (IXA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IXA), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IXA), X is CY1; and Y1 is Cl. In another embodiment of Formula (IXA), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (IXA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IXA), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IXA), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IXA), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IXA), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IXA), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IXA), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (IXA), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IXA), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (IXA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IXA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (IXA), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IXA), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (IXA), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IXA), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (IXA), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (IXA), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (IXA), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (IXA), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (IXA), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IXA), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (IXA), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IXA)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl;
- with the provisos that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent; and
- when X is CY1 and Y1 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenyl.
- Still another embodiment pertains to compounds having Formula (IXA), which includes Examples 53, 54, 76, 314, 323, 491, and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (XA)
- and pharmaceutically acceptable salts thereof; wherein R4 is as described herein for Formula (IA).
- One embodiment pertains to compounds of Formula (XA) or pharmaceutically acceptable salts thereof;
- wherein
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R1, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I; and
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl.
- In one embodiment of Formula (XA), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (XA), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (XA), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (XA), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (XA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (XA), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (XA), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (XA), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (XA), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (XA), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (XA), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (XA), R9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, and F.
- In one embodiment of Formula (XA), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (XA), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (XA), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (XA), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (XA), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (XA)
- wherein
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, CO(O)R11, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl.
- Still another embodiment pertains to compounds having Formula (XA), which includes Examples 217, 230, 231, 232, 233, 234, 235, 236, 237, 238, 239, 298, 301, 308, 309, 310, 311, 312, 313, 315, 367, 368, 369, 370, 371, 372, 373, 374, 375, 376, 377, 378, 402, 437, 440, 441, 484, 488, 490, 498, 499, 500, 501, 502, 503, 504, 505, 506, 507, 508, 509, 510, 511, 512, 513, 514, 515, 516, 517, 518, 519, 520, 521, 522, 523, 524, 525, 526, 527, 528, 529, 530, 531, 532, 533, 534, 535, 536, 537, 538, 539, 547, 548, 549, 550, 551, 552, 557, 562, 567, 568, 569, 580, 581, 582, 583, 584, 585, 586, 587, 588, 589, 590, 591, 592, 593, 594, 595, 596, 597, 598, 599, 600, 601, 602, 603, 604, 605, 606, 607, 608, 609, 610, 611, 612, 613, 614, 615, 616, 617, 618, 619, 620, 623, 624, 625, 626, 627, 628, 629, 630, 631, 632, 633, 634, 635, 636, 637, 638, 639, 640, 641, 642, 643, 644, 645, 646, 647, 648, 649, 650, 651, 652, 653, 654, 655, 656, 657, 658, 659, 660, 661, 662, 663, 664, 665, 666, 667, 668, 669, 670, 671, 672, 682, 683, 684, 699, 700, 701, 702, 703, 704, 705, 706, 707, 708, 731, 732, 733, 737, 913, 914, 915, 916, 917, 918, 919, 920, 921, 922, 923, 924, 925, 926, 927, 928, 929, 930, 931, 932, 933, 934, 935, 936, 937, 958, 959, 960, 961, 962, 963, 964, 965, 966, 967, 968, 969, 970, 971, 972, 973, 974, 975, 976, 977, 978, 979, 980, 981, 982, 983, 984, 985, 986, 987, 988, 989, 990, 991, 992, 993, 994, 995, 996, 997, 998, 999, 1000, 1001, 1002, 1003, 1004, 1005, 1006, 1007, 1008, 1009, 1010, 1061, 1062, 1063, 1064, 1068, 1077, 1084, 1085, 1086, 1087, 1088, 1089, 1090, 1091, 1092, 1093, 1094, 1095, 1096, 1097, 1098, 1099, 1100, 1101, 1102, 1103, 1104, 1105, 1106, 1107, 1108, 1109, 1110, 1111, 1112, 1113, 1114, 1115, 1116, 1117, 1118, 1119, 1120, and pharmaceutically acceptable salts thereof.
- One embodiment, therefore, pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IB)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R1 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3; and
- Z is CH, C—F, C—Cl, C—Br, C—I or N; or
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R1 is hydrogen, F, Cl, Br, or I;
- Z is CR2; and
- R2 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3; and
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R3x phenyl and heterocyclyl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I;
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2CHCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- m is 4, 5, or 6; and
- n is 1 or 2;
- with the provisos that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent;
-
- when X is CY1 and Y1 is hydrogen; R1 is NHC(O)R3; R2 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenyl;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is furanyl; the R3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is thienyl; the R3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is R3 phenyl; the phenyl is not substituted at the para position with SO2R4 or SO2NHR4.
- In one embodiment of Formula (IB), X is N or CY1. In another embodiment of Formula (IB), X is N. In another embodiment of Formula (IB), X is CY1.
- In one embodiment of Formula (IB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IB), X is CY1; and Y1 is Cl. In another embodiment of Formula (IB), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (IB), Z is CH, C—F, C—Cl, C—Br, C—I or N; and R is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3. In another embodiment of Formula (IB), Z is CH or N; and R1 is NHC(O)NHR3. In another embodiment of Formula (IB), Z is CH or N; and R1 is NHC(O)NH(CH2)mR3x. In another embodiment of Formula (IB), Z is CH or N; and R1 is CH2NHC(O)NHR3. In another embodiment of Formula (IB), Z is CH or N; and R1 is NHC(O)R3. In another embodiment of Formula (IB), Z is CH or N; and R1 is NHC(O)(CH2)nR3. In another embodiment of Formula (IB), Z is CH or N; and R1 is C(O)NH(CH2)nR3. In another embodiment of Formula (IB), Z is CH or N; and R1 is NHC(O)(CH2)mR3x. In another embodiment of Formula (IB), Z is CH or N; and R1 is C(O)NH(CH2)mR3x. In another embodiment of Formula (IB), Z is CH or N; and R1 is CH2C(O)NHR3. In another embodiment of Formula (IB), Z is CH or N; and R1 is CH2NHC(O)R3.
- In one embodiment of Formula (IB), Z is CH; and R1 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3. In another embodiment of Formula (IB), Z is CH; and R1 is NHC(O)NHR3. In another embodiment of Formula (IB), Z is CH; and R1 is NHC(O)NH(CH2)mR3x. In another embodiment of Formula (IB), Z is CH; and R1 is CH2NHC(O)NHR3. In another embodiment of Formula (IB), Z is CH; and R1 is NHC(O)R3.
- In another embodiment of Formula (IB), Z is CH; and R1 is NHC(O)(CH2)nR3. In another embodiment of Formula (IB), Z is CH; and R1 is C(O)NH(CH2)nR3. In another embodiment of Formula (IB), Z is CH; and R1 is NHC(O)(CH2)mR3x. In another embodiment of Formula (IB), Z is CH; and R1 is C(O)NH(CH2)mR3x. In another embodiment of Formula (IB), Z is CH; and R1 is CH2C(O)NHR3. In another embodiment of Formula (IB), Z is CH; and R1 is CH2NHC(O)R3.
- In one embodiment of Formula (IB), Z is N; and R1 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3. In another embodiment of Formula (IB), Z is N; and R1 is NHC(O)NHR3. In another embodiment of Formula (IB), Z is N; and R1 is NHC(O)NH(CH2)mR3x. In another embodiment of Formula (IB), Z is N; and R1 is CH2NHC(O)NHR3. In another embodiment of Formula (IB), Z is N; and R1 is NHC(O)R3.
- In another embodiment of Formula (IB), Z is N; and R1 is NHC(O)(CH2)nR3. In another embodiment of Formula (IB), Z is N; and R1 is C(O)NH(CH2)nR3. In another embodiment of Formula (IB), Z is N; and R1 is NHC(O)(CH2)mR3x. In another embodiment of Formula (IB), Z is N; and R1 is C(O)NH(CH2)mR3x. In another embodiment of Formula (IB), Z is N; and R1 is CH2C(O)NHR3. In another embodiment of Formula (IB), Z is N; and R1 is CH2NHC(O)R3.
- In one embodiment of Formula (IB), R1 is hydrogen; Z is CR2; and R2 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3. In another embodiment of Formula (IB), R1 is hydrogen; Z is CR2; and R2 is NHC(O)NHR3. In another embodiment of Formula (IB), R1 is hydrogen; Z is CR2; and R2 is NHC(O)NH(CH2)mR3x. In another embodiment of Formula (IB), R1 is hydrogen; Z is CR2; and R2 is CH2NHC(O)NHR3. In another embodiment of Formula (IB), R1 is hydrogen; Z is CR2; and R2 is NHC(O)R3. In another embodiment of Formula (IB), R1 is hydrogen; Z is CR2; and R2 is NHC(O)(CH2)nR3. In another embodiment of Formula (IB), R1 is hydrogen; Z is CR2; and R2 is C(O)NH(CH2)nR3.
- In another embodiment of Formula (IB), R1 is hydrogen; Z is CR2; and R2 is NHC(O)(CH2)mR3x. In another embodiment of Formula (IB), R1 is hydrogen; Z is CR2; and R2 is C(O)NH(CH2)mR3x. In another embodiment of Formula (IB), R1 is hydrogen; Z is CR2; and R2 is CH2C(O)NHR3. In another embodiment of Formula (IB), R1 is hydrogen; Z is CR2; and R2 is CH2NHC(O)R3.
- In one embodiment of Formula (IB), m is 4, 5, or 6. In another embodiment of Formula (IB), m is 4. In another embodiment of Formula (IB), m is 5. In another embodiment of Formula (IB), m is 6.
- In one embodiment of Formula (IB), n is 1 or 2. In another embodiment of Formula (IB), n is 1. In another embodiment of Formula (IB), n is 2.
- In one embodiment of Formula (IB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, SO2R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IB), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, SO2R4, OR4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IB), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IB), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IB), R3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R3x phenyl and heterocycyl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IB), R3x is heterocyclyl; wherein each R3x heterocycyl is substituted with C(O)R4, or CO(O)R4.
- In one embodiment of Formula (IB), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IB), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (IB), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IB), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (IB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (IB), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IB), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (IB), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IB), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (IB), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (IB), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, CN, F, and Cl.
- In one embodiment of Formula (IB), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (IB), R10 at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (IB), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH.
- In another embodiment of Formula (IB), R11, at each occurrence, is independently alkyl.
- In another embodiment of Formula (IB), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IB)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R1 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, NHC(O)(CH2)nR3, C(O)NH(CH2)nR3, NHC(O)(CH2)mR3x, C(O)NH(CH2)mR3x, CH2C(O)NHR3, and CH2NHC(O)R3; and
- Z is CH, C—F, or N; or
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, and Cl;
- R1 is hydrogen;
- Z is CR2; and R2 is independently selected from the group consisting of NHC(O)NHR3, NHC(O)NH(CH2)mR3x, CH2NHC(O)NHR3, NHC(O)R3, CH2C(O)NHR3, and CH2NHC(O)R3; and
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R3x is heterocyclyl; wherein the R3x heterocyclyl is substituted with one, two, three or four substituents independently selected from the group consisting of C(O)R4, CO(O)R4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, CN, F, Cl, Br and I;
- R10 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F;
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- m is 4, or 5; and
- n is 1;
- with the provisos that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent;
- when X is CY1 and Y1 is hydrogen; R1 is NHC(O)R3; R2 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenyl; when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is furanyl; the R3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is thienyl; the R3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
- when X is CY1 and Y1 is hydrogen; R1 is C(O)NH(CH2)nR3; n is 1; R2 is hydrogen; and R3 is R3 phenyl; the phenyl is not substituted at the para position with SO2R4 or SO2NHR4.
- Still another embodiment pertains to compounds having Formula (IB), which includes
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(3-methylbutyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-7-ylcarbamoyl)amino]-N-(3-methylbutyl)benzamide;
- 2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-phenylethyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(morpholin-4-yl)ethyl]benzamide;
- N-(1-hydroxy-2-methylpropan-2-yl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- N-benzyl-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- N-(cyclopentylmethyl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(piperidin-1-yl)propyl]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-phenoxyethyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(pyrrolidin-1-yl)ethyl]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(propan-2-yloxy)ethyl]benzamide;
- N-(2-hydroxy-2-methylpropyl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(2-oxopyrrolidin-1-yl)ethyl]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydrofuran-2-ylmethyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-propylbenzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(morpholin-4-yl)propyl]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-phenylbenzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-methylbutyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(2-oxopyrrolidin-1-yl)propyl]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydro-2H-pyran-4-ylmethyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydro-2H-pyran-2-ylmethyl)benzamide;
- N-[(1,1-dioxidotetrahydrothiophen-3-yl)methyl]-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-3,6-dihydropyridine-1 (2H)-carboxylate;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(tetrahydrofuran-3-yl)acetamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea;
- 1-{4-[1-(2-hydroxy-2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(morpholin-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea;
- 1-{4-[1-(ethoxyacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(2-methoxyethoxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea;
- 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(1-methylpiperidin-4-yl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)urea;
- 1-(4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea;
- 2-ethoxy-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(tetrahydro-2H-pyran-4-yl)acetamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(morpholin-4-yl)acetamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(2-methoxyethoxy)acetamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-3-methoxy-2-methylpropanamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}butanamide; 4,4,4-trifluoro-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}butanamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}tetrahydro-2H-pyran-4-carboxamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-4-methylpentanamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-1-methylpiperidine-4-carboxamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}tetrahydro-2H-thiopyran-4-carboxamide 1,1-dioxide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-1,4-dioxane-2-carboxamide;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea;
- 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 2-[(4-cyanobenzyl)(3-methylbutanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide;
- 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide;
- 2-[(4-cyanobenzyl)(3-methylbutanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]butyl}piperidine-1-carboxylate;
- 4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}-N-(3-methylbutyl)benzamide;
- 2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)acetamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(3-methylbutyl)amino]-1,3-thiazole-5-carboxamide;
- 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(propan-2-yloxy)acetyl]piperidin-4-yl}butyl)urea;
- 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]butyl}-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-{4-[1-(cyclopropylacetyl)piperidin-4-yl]butyl}-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]butyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]butyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]butyl}urea;
- 1-{4-[1-(cyclopentylcarbonyl)piperidin-4-yl]butyl}-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]butyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(2-methoxyethoxy)acetyl]piperidin-4-yl}butyl)urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(morpholin-4-ylacetyl)piperidin-4-yl]butyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]butyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)piperidin-4-yl]butyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]butyl}urea;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 2-cyclopentyl-N-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}acetamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydrofuran-2-ylacetyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydro-2H-pyran-4-ylacetyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(morpholin-4-ylacetyl)amino]benzamide;
- 4-[(3-cyclopentylpropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[(propan-2-yloxy)acetyl]amino}benzamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenyl}-3,6-dihydropyridine-1 (2H)-carboxylate;
- N-{4-[(cyclopentylacetyl)amino]benzyl}imidazo[1,2-a]pyridine-6-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(3-phenylpyrrolidin-1-yl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methylbutyl)amino]-1,3-thiazole-5-carboxamide;
- 2-(1,3-dihydro-2H-isoindol-2-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- 4-[1-(2-hydroxy-2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(morpholin-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-3-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-2-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[3-(tetrahydrofuran-2-yl)propanoyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide;
- 4-[1-(cyclopentylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-3-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- 4-[1-(1,4-dioxan-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[(2-methoxyethoxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide;
- 4-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 4-{1-[(4,4-difluorocyclohexyl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea;
- 1-[4-(1-benzoylpiperidin-4-yl)butyl]-3-imidazo[1,2-a]pyridin-6-ylurea;
- 2-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[2-oxo-4-(tetrahydrofuran-3-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide;
- 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)acetamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(2-oxo-5-phenyl-1,3-oxazolidin-3-yl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methyl-1,3-thiazol-5-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methyl-1,3-thiazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(3-methyl-1,2-oxazol-5-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- 2-{[3-(3-chloro-1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(3-methoxy-1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- 2-{[(3,5-dimethyl-1,2-oxazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- 2-{[3-(3,5-dimethyl-1,2-oxazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1-methyl-1H-pyrazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(4-methyl-1,3-thiazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-2-ylmethyl)(1H-tetrazol-5-ylacetyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(1,2-oxazol-3-ylacetyl)(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1,2-oxazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-2-ylmethyl) [3-(1,3-thiazol-2-yl)propanoyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methylbutanoyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydrofuran-3-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-3-ylmethyl)(tetrahydro-2H-pyran-4-ylcarbonyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydrofuran-3-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-3-ylcarbonyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydro-2H-pyran-4-ylcarbonyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(3-methoxypropanoyl)[(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-3-ylcarbonyl) [(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2R)-tetrahydrofuran-2-ylmethyl](tetrahydro-2H-pyran-4-ylcarbonyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(3-methoxypropanoyl) [(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-3-ylcarbonyl) [(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2S)-tetrahydrofuran-2-ylmethyl](tetrahydro-2H-pyran-4-ylcarbonyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydro-2H-pyran-4-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-({[2-(propan-2-yloxy)ethyl]carbamoyl}[(2R)-tetrahydrofuran-2-ylmethyl]amino)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl][(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-({[2-(propan-2-yloxy)ethyl]carbamoyl}[(2S)-tetrahydrofuran-2-ylmethyl]amino)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydrofuran-3-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- 2-[5-(4-chlorophenyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide;
- 4-[(1-acetylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 4-{[1-(cyclopropylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}benzamide;
- 4-{[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide; 4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)benzamide; 4-[(1-butanoylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(3-methoxy-2-methylpropanoyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}benzamide;
- 4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropanoyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(cyclohexylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(2R)-2-hydroxybutyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4R)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide;
- 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(1-methyl-1H-pyrazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- 2-{[(1,3-dimethyl-1H-pyrazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4S)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 2-{(4R)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- 2-{(4S)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1-methyl-1H-pyrrol-2-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- 2-{[(1,5-dimethyl-1H-pyrazol-3-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-2-ylmethyl)(1,3-thiazol-4-ylacetyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(1,2-oxazol-3-ylacetyl)[(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(5-methyl-1,2-oxazol-3-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1,2-oxazol-5-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1,2-oxazol-4-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(2R)-tetrahydrofuran-2-ylmethyl](1,3-thiazol-4-ylacetyl)amino}-1,3-thiazole-5-carboxamide;
- 2-{[(1,5-dimethyl-1H-pyrazol-3-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1-methyl-1H-pyrazol-4-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- 2-{[(3,5-dimethyl-1,2-oxazol-4-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(1-methyl-1H-pyrazol-4-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1-methyl-1H-pyrrol-2-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- 2-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- tert-butyl {4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydro-2H-pyran-4-ylacetyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-2-ylacetyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[3-(tetrahydrofuran-2-yl)propanoyl]amino}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(propan-2-yloxy)acetyl]amino}benzamide; 4-[(3-cyclopentylpropanoyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(4-methylpentanoyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide;
- 4-[(4-cyanobenzyl)(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate;
- 2-{5-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(morpholin-4-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(3-hydroxy-3-methylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea;
- 1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide;
- 4-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 5-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]thiophene-2-carboxamide;
- 1-(4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 2-[(2S)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4R)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide;
- 5-[1-(cyclopropylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[(4R)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]thiophene-2-carboxamide;
- 2-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(5S)-2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(5R)-2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methoxyacetyl)piperidin-4-yl]thiophene-2-carboxamide;
- 5-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- 5-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(1,2-oxazol-5-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 5-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[(4R)-4-hydroxy-2-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[(4S)-4-hydroxy-2-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 1-[4-(1-benzoylpiperidin-4-yl)butyl]-3-imidazo[1,2-a]pyridin-7-ylurea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methylsulfonyl)piperidin-4-yl]thiophene-2-carboxamide;
- 5-[1-(cyclohexylmethyl)-5-ethyl-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methoxy-3,3-dimethylcyclohexyl)methyl]-5-methyl-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-4-methylpentanamide;
- 3-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)propanamide;
- N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(propan-2-yloxy)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydrofuran-2-yl)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydro-2H-pyran-4-yl)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-3-phenylpropanamide;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-4-methylpentanamide;
- 3-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)propanamide;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(propan-2-yloxy)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydrofuran-2-yl)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydro-2H-pyran-4-yl)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3-phenylpropanamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3R)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}phenyl)urea;
- tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3,6-dihydropyridine-1(2H)-carboxylate;
- tert-butyl (3R)-3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)pyrrolidine-1-carboxylate;
- tert-butyl {2-fluoro-4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-propyl-1H-pyrazol-4-yl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(morpholin-4-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-(1-ethyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(1,1-dioxidotetrahydrothiophen-3-yl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 2-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- 4-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-phenylthiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(methylsulfonyl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}pyrrolidine-1-carboxylate;
- tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)pyrrolidine-1-carboxylate;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)biphenyl-2-sulfonamide;
- 5-{1-[(2R)-2-hydroxypropyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-[(cyclopentylacetyl)amino]-3-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 1-{2-fluoro-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3R)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide;
- 4-[1-(cyclopropylacetyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- tert-butyl 4-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}-3,6-dihydropyridine-1 (2H)-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide;
- 5-[1-(1,4-dioxan-2-ylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(propan-2-yloxy)phenyl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide;
- tert-butyl 4-[4-(imidazo[1,2-a]pyridin-7-ylcarbamoyl)phenyl]piperidine-1-carboxylate;
- tert-butyl 4-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoyl)phenyl]piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(2-methylpropanoyl)amino]oxetan-3-yl}thiophene-2-carboxamide;
- 5-[3-(benzoylamino)oxetan-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(tetrahydrofuran-3-ylacetyl)amino]oxetan-3-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(pentanoylamino)oxetan-3-yl]thiophene-2-carboxamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)phenyl]urea;
- 1-(4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}phenyl)urea;
- 1-(4-{[(3R)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)urea;
- 1-(4-{[(3R)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydrofuran-3-ylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}phenyl)urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3R)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}benzamide;
- 5-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- 4-{[(3S)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{[(3S)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(3-methoxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide;
- 4-{[(3S)-1-butanoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide;
- 4-{[(3S)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{[(3S)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{[(3S)-1-(3-hydroxy-3-methylbutanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 2-(4-benzoylpiperazin-1-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(propan-2-yl)piperazin-1-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(2-methoxyethyl)piperazin-1-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide;
- 1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-phenyl-1,3-thiazole-5-carboxamide;
- 1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxamide;
- tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)azetidine-1-carboxylate;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate;
- tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(1,4-dioxan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]benzamide;
- 1-[4-(1-acetylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}phenyl)urea;
- 1-{4-[1-(cyclopropylacetyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-[4-(1-benzoylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(propan-2-yloxy)acetyl]pyrrolidin-3-yl}phenyl)urea;
- 1-{4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]phenyl}urea;
- 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(morpholin-4-ylacetyl)pyrrolidin-3-yl]phenyl}urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 4-{[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoyl]amino}-N-(tetrahydro-2H-pyran-2-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- N-[(3-chloroimidazo[1,2-a]pyridin-6-yl)methyl]-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide;
- 5-(4-hydroxytetrahydro-2H-pyran-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[3-hydroxy-1-(2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-(1-benzoyl-3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}azetidine-1-carboxylate;
- tert-butyl 4-hydroxy-4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[5-(piperidin-1-ylcarbonyl)-1,3-thiazol-2-yl]urea;
- 5-{3-hydroxy-1-[(2S)-2-methylbutanoyl]azetidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[3-hydroxy-1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 2-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}-N-(3-methylbutyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(3-{[(2S)-2-methylbutanoyl]amino}oxetan-3-yl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1-[1-(3-methylbutanoyl)piperidin-4-yl]-1H-pyrazole-3-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 4-[(1-acetylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]piperidin-4-yl}oxy)benzamide;
- 4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[(1-benzoylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)benzamide;
- 4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}benzamide;
- 4-{[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(morpholin-4-ylacetyl)piperidin-4-yl]oxy}benzamide;
- 1-{4-[(1-acetylazetidin-3-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-2-methylbutanoyl]azetidin-3-yl}oxy)phenyl]urea;
- 1-(4-{[1-(cyclopropylacetyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[(1-benzoylazetidin-3-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(propan-2-yloxy)acetyl]azetidin-3-yl}oxy)phenyl]urea;
- 1-(4-{[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)azetidin-3-yl]oxy}phenyl)urea;
- 1-(4-{[1-(1,4-dioxan-2-ylcarbonyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]oxy}phenyl)urea;
- tert-butyl (3R)-3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}pyrrolidine-1-carboxylate;
- 4-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 1-[4-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 4-{1-[(3,3-difluorocyclobutyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-2-methylbutanoyl]piperidin-4-yl}oxy)phenyl]urea;
- 1-(4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[(1-benzoylpiperidin-4-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)phenyl]urea;
- 1-(4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)azetidin-3-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]azetidin-3-yl}phenyl)urea;
- 1-{4-[1-(cyclopropylacetyl)azetidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-[4-(1-benzoylazetidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(propan-2-yloxy)acetyl]azetidin-3-yl}phenyl)urea;
- 1-{4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)azetidin-3-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]phenyl}urea;
- 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[6-(morpholin-4-yl)pyridin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methyltetrahydro-2H-pyran-2-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropanoyl)amino]cyclobutyl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylbutanoyl)amino]cyclobutyl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-{[(2S)-2-methylbutanoyl]amino}cyclobutyl)thiophene-2-carboxamide;
- 5-[1-(benzoylamino)cyclobutyl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3,3,3-trifluoropropanoyl)amino]cyclobutyl}thiophene-2-carboxamide;
- N-(1-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}cyclobutyl)tetrahydro-2H-pyran-4-carboxamide;
- tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}azetidine-1-carboxylate;
- 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 4-[1-(furan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(piperidin-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-phenoxybenzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)azetidin-3-yl]benzamide;
- tert-butyl 4-{4-[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoyl]phenyl}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide;
- 4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-phenoxyphenyl)urea;
- 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(2,2-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclohexylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide;
- 4-(1-butanoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylpent-2-enoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyloxetan-3-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1-cyanocyclopropyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopentylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-oxobutanoyl)piperidin-4-yl]benzamide;
- 4-{1-[(2,5-dimethylfuran-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(3-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(4-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-propanoylpiperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(2,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide;
- 2-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- 4-[(cyclopentylacetyl)amino]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]azetidin-3-yl}benzamide;
- 4-[1-(cyclopropylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-benzoylazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)azetidin-3-yl]benzamide;
- 5-[4-hydroxy-1-(3-methylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[4-hydroxy-1-(2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3,3-dimethylbutanoyl)-4-hydroxypiperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-(1-benzoyl-4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]azetidin-3-yl}oxy)benzamide;
- 4-{[1-(cyclopropylacetyl)azetidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[(1-benzoylazetidin-3-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- tert-butyl 4-{4-[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate;
- 2-cyclopentyl-N-(4-{[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)acetamide;
- tert-butyl 4-(4-{[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-1-ylcarbonyl)benzamide;
- 4-[1-(ethylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopropylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)azetidin-3-yl]benzamide;
- propan-2-yl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate;
- 2-methylpropyl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]piperidin-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-[1-(2-cyano-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3R)-tetrahydrofuran-3-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(cyclopentylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(cyclohexylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(cyclohexylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(furan-3-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]pyrrolidin-3-yl}benzamide;
- 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(ethylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopropylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(cyclopentylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)azetidin-3-yl]benzamide;
- 4-[1-(cyclopentylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(2,2-dimethylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)azetidin-3-yl]benzamide;
- 4-[1-(2-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(furan-2-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,4-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(2-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)azetidin-3-yl]benzamide;
- 4-[1-(4-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,2-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)azetidin-3-yl]benzamide;
- 4-[1-(3,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyanobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(cyclohexylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)azetidin-3-yl]benzamide;
- 4-[1-(cyclohexylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)azetidin-3-yl]benzamide;
- 4-[1-(furan-3-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrimidin-4-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(2,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]azetidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]azetidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]azetidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)pyrrolidin-3-yl]benzamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]phenyl}urea;
- 5-[1-(1,4-dioxan-2-ylmethyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate;
- 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide;
- tert-butyl 4-(4-{[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate;
- 2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]amino}phenyl)acetamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)piperidin-4-yl]benzamide;
- 4-[1-(cyclopropylsulfonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 5-{(1R)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{(1R)-3-methyl-1-[(tetrahydrofuran-3-ylacetyl)amino]butyl}thiophene-2-carboxamide;
- 5-{(1S)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1-phenylpiperidin-4-yl)-1,3-thiazole-5-carboxamide;
- 1-(4-{[(3R)-1-(2-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(3-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(4-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[4-(trifluoromethyl)benzoyl]pyrrolidin-3-yl}oxy)phenyl]urea;
- 1-(4-{[(3R)-1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(2-chlorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(4-chlorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(pyridin-2-yl)piperidin-4-yl]-1,3-thiazole-5-carboxamide;
- 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-[1-(2-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylacetyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide;
- 1-[4-(1-butanoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methylcyclopropyl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(cyclopropylacetyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]phenyl}urea;
- 1-(4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(phenylacetyl)piperidin-4-yl]phenyl}urea;
- 5-[1-(cyclopropylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 1-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(3-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(4-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[1-(3-fluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[1-(2,4-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[1-(2,5-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[1-(3,4-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[1-(3,5-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylacetyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methyl-2-phenylpropanoyl)pyrrolidin-3-yl]benzamide;
- 4-{1-[difluoro(phenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]furan-2-carboxamide;
- 4-[1-(2-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- 2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}acetamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- 5-(1-benzyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide;
- 5-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[4-(2-methylpropyl)phenyl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-2-methylbutanoyl]-1,2,3,6-tetrahydropyridin-4-yl}furan-2-carboxamide;
- 5-[1-(3,3-dimethylbutanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 5-[1-(cyclopropylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{1-[(2-methylpropyl)sulfonyl]pyrrolidin-3-yl}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(phenylsulfonyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]-1,2,3,6-tetrahydropyridin-4-yl}furan-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidine-1-carboxylate;
- 5-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(4-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-{1-[(3-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(3,5-difluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(2-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(4-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- 5-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- 5-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-4-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrazol-4-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- 5-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2E)-2-methylpent-2-enoyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- 5-{1-[(2,5-dimethylfuran-3-yl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-propanoylpyrrolidin-3-yl)thiophene-2-carboxamide;
- 5-{1-[(1-cyanocyclopropyl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-(1-butanoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-[1-(2,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(thiophen-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methylpiperidin-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 5-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyrazin-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylthiophen-2-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-3-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrazol-5-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- 5-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(phenylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide;
- 2-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- 5-[1-(2-fluorobenzoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 2-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide;
- 2-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- tert-butyl 4-[2-(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)ethyl]piperazine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide;
- 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide;
- 4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(3-methylbutanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(propan-2-ylsulfonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-5-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutyl)-1H-pyrazol-5-yl]furan-2-carboxamide;
- 5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{[2-(2-methylpropyl)pyrrolidin-1-yl]carbonyl}thiophene-2-carboxamide;
- 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide;
- 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(3-methylbutanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide;
- 5-[1-(2-methylpropanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3-methylbutanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- 5-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(1-methylpiperidin-4-yl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-cyanobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-6-ylacetyl)amino]phenyl}acetamide;
- tert-butyl 4-{4-[(imidazo[1,2-b]pyridazin-6-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate;
- 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-b]pyridazin-6-ylmethyl)benzamide;
- 5-(1-benzyl-3-cyclopropyl-1H-pyrazol-5-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(propan-2-ylsulfonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(phenylsulfonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylacetyl)amino]phenyl}piperidine-1-carboxylate;
- N-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-6-yl)acetamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(phenylsulfonyl)piperidin-4-yl]benzamide;
- 2-(imidazo[1,2-a]pyridin-6-yl)-N-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}acetamide;
- N-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-6-yl)acetamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(2-methoxyphenyl)acetyl]amino}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(phenylacetyl)amino]benzamide;
- 4-(benzoylamino)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 2,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide;
- 3,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide;
- 3,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide;
- 2,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide;
- 2-fluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide;
- N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-3-methoxybenzamide;
- 4-{[(2-fluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[2-(2-methylpropyl)pyrrolidin-1-yl]carbonyl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-methyl-2-(piperazin-1-yl)propanoyl]piperidin-4-yl}thiophene-2-carboxamide;
- N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-2-methoxybenzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(phenylsulfonyl)benzamide;
- 4-(phenylsulfonyl)-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)benzamide;
- 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tricyclo[3.3.1.1˜3,7˜]dec-1-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 5-(1-benzyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-oxatricyclo[3.3.1.1˜3,7˜]dec-1-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- 4-{[(2,5-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{[(2,4-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 5-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[3-cyclopropyl-1-(2-methoxyethyl)-1H-pyrazol-5-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 4-{[difluoro(phenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(2-methyl-2-phenylpropanoyl)amino]benzamide;
- N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(phenylsulfonyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-(phenylsulfonyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-5-yl]thiophene-2-carboxamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}piperidine-1-carboxylate;
- N-[(3-chloroimidazo[1,2-a]pyrazin-6-yl)methyl]-4-[(cyclopentylacetyl)amino]benzamide;
- N-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide;
- 2-(imidazo[1,2-a]pyridin-7-yl)-N-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}acetamide;
- 1-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea;
- N-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-methyl-3-(2-methylpropyl)-1H-pyrazol-5-yl]thiophene-2-carboxamide;
- 5-[1-benzyl-3-(2-methylpropyl)-1H-pyrazol-5-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide;
- N-(2,5-difluorobenzyl)-N′-(imidazo[1,2-a]pyridin-7-ylmethyl)benzene-1,4-dicarboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[2-(propan-2-yl)pyrrolidin-1-yl]carbonyl}benzamide;
- N-{4-[5-(2,2-dimethylpropyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide;
- tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate;
- 4-{1-[(2-chloropyridin-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbut-2-enoyl)piperidin-4-yl]benzamide;
- 4-[1-(3-fluoro-4-methoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopent-1-en-1-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-[1-(2-ethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(4-fluorophenoxy)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxyphenyl)acetyl]piperidin-4-yl}benzamide;
- 4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(2-acetylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(methoxymethyl)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenylpropanoyl)piperidin-4-yl]benzamide;
- 4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[(2-methylpropyl)sulfonyl]acetyl}piperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenoxypropanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-({[(1R,2S)-2-methylcyclohexyl]oxy}acetyl)piperidin-4-yl]benzamide;
- 4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methoxyphenyl)acetyl]piperidin-4-yl}benzamide;
- 4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylbut-2-enoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxy-5-methylphenyl)acetyl]piperidin-4-yl}benzamide;
- 4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 1-(4-{1-[(2-chloropyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3-methylbut-2-enoyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methylcyclopent-1-en-1-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(2-ethylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(4-fluorophenoxy)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,4-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,5-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3-methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-oxo-2,3-dihydro-1H-inden-4-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-2-methylbut-2-enoyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(1H-indol-3-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrrolidin-1-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)benzamide;
- 4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-2,1-benzoxazol-3-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(2-chloro-3-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(pyridin-2-yl)cyclopropyl]carbonyl}piperidin-4-yl)benzamide;
- 4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,4-dihydro-2H-chromen-6-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(cyclohexyloxy)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(2-chloropyridin-3-yl)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(5-cyclopropyl-1,2-oxazol-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2H-chromen-3-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3,5-difluoropyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxycyclohexyl)carbonyl]piperidin-4-yl}benzamide;
- 4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-4-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-1,3-benzoxazol-6-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thieno[3,2-b]pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinolin-7-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(5,6,7,8-tetrahydroquinolin-3-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-7-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinoxalin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-3-(2-methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-3-(pyridin-2-yl)prop-2-enoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(8-methylimidazo[1,2-a]pyridin-2-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methyl-4H-furo[3,2-b]pyrrol-5-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-8-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[3-methyl-1-(prop-2-en-1-yl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)benzamide;
- 4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)pyrimidin-4-yl]carbonyl}piperidin-4-yl)benzamide;
- 4-{1-[(5,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)tetrahydro-2H-pyran-4-yl]carbonyl}piperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxy-6-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)phenyl]urea;
- 1-(4-{1-[(2S)-2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-tetrahydro-2,1-benzoxazol-3-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(4-{1-[(2-chloro-5-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(2-chloro-3-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-(pyridin-2-yl)cyclopropyl]carbonyl}piperidin-4-yl)phenyl]urea;
- 1-(4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-[4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,3-dihydro-1-benzofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxycyclohexyl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-4-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-1,3-benzoxazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(cinnolin-4-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(quinolin-7-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(5,6,7,8-tetrahydroquinolin-3-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-7-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(quinoxalin-2-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-(2-methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-(pyridin-2-yl)prop-2-enoyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(4-chloro-2,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(8-methylimidazo[1,2-a]pyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methyl-4H-furo[3,2-b]pyrrol-5-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(4-chloro-1-ethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-8-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[3-methyl-1-(prop-2-en-1-yl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)phenyl]urea;
- 1-{4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(5,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 4-{1-[(2-chloro-5-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-methyl-5-(propan-2-yl)furan-3-yl]carbonyl}piperidin-4-yl)benzamide;
- 1-(4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3,5-difluoropyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- tert-butyl 4-{3-fluoro-4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(piperidin-1-ylcarbonyl)piperidin-4-yl]benzamide;
- 1-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(4-methylpentanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(2-fluoro-4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2-cyanobenzoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-N,N-dimethylpiperidine-1-carboxamide;
- 1-{2-fluoro-4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 4-[(cyclopentylacetyl)amino]-N-[(7-fluoroimidazo[1,2-a]pyridin-6-yl)methyl]benzamide;
- N-[(7-fluoroimidazo[1,2-a]pyridin-6-yl)methyl]-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-2-(imidazo[1,2-a]pyridin-7-yl)acetamide;
- 5-{1-[2,2-dimethyl-3-(piperazin-1-yl)propyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3-amino-2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-{1-[(2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-indazol-6-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(5-cyclopropylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]acetyl}piperidin-4-yl)benzamide;
- 4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-1-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxy-5-methylpyridin-2-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[4-(propan-2-yl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-5-propyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-yl)propanoyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2,3-dihydro-1-benzofuran-7-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)-1,3-thiazol-4-yl]carbonyl}piperidin-4-yl)benzamide;
- 4-(1-{[1-(difluoromethyl)-5-methyl-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(4-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazolo[1,5-a]pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)-1,3-oxazol-4-yl]carbonyl}piperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxy-5-methylpyridin-3-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(5,6-dimethoxypyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2H-indazol-4-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2H-indazol-6-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-indazol-4-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(trifluoromethyl)furan-3-yl]carbonyl}piperidin-4-yl)benzamide;
- 1-(4-{1-[(2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(thieno[3,2-b]furan-5-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(5-cyclopropylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-[4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4-yl]carbonyl}piperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxy-5-methylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[4-(propan-2-yl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-5-propyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-yl)propanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(pyrazolo[1,5-a]pyridin-2-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2-(propan-2-yl)-1,3-oxazol-4-yl]carbonyl}piperidin-4-yl)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-7-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methoxy-5-methylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(5,6-dimethoxypyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2H-indazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2H-indazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2-(trifluoromethyl)furan-3-yl]carbonyl}piperidin-4-yl)phenyl]urea;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrimidin-4-yl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpyrimidin-4-yl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[6-(trifluoromethyl)pyrimidin-4-yl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide;
- 5-[1-({3,5-dimethyl-7-[2-(methylamino)ethoxy]tricyclo[3.3.1.13,7]dec-1-yl}methyl)-5-methyl-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide;
- 4-(1-benzoylpiperidin-4-yl)-2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide;
- 2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide;
- 2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-({4-methyl-1-[2-(piperazin-1-yl)ethyl]piperidin-4-yl}methyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- S-(2-{4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidin-1-yl}-2-oxoethyl)-L-cysteine;
- 5-(1-{[1-(15-amino-4,7,10,13-tetraoxapentadecan-1-oyl)-4-methylpiperidin-4-yl]methyl}-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- S-{2-[(3-{4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidin-1-yl}-3-oxopropyl)amino]-2-oxoethyl}-L-cysteine; and pharmaceutically acceptable salts thereof.
- Still another embodiment pertains to compounds of Formula (IB) selected from the group consisting of
- 4-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluoro-4-methoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(2-acetylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(methoxymethyl)benzoyl]piperidin-4-yl}benzamide;
- 4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxy-6-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (IIB)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (IB).
- One embodiment pertains to compounds of Formula (IIB) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (IIB), X is N or CY1. In another embodiment of Formula (IIB), X is N. In another embodiment of Formula (IIB), X is CY1.
- In one embodiment of Formula (IIB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IIB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IIB), X is CY1; and Y1 is Cl. In another embodiment of Formula (IIB), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (IIB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IIB), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IIB), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IIB), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IIB), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIB), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (IIB), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIB), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (IIB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (IIB), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIB), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (IIB), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IIB), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (IIB), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (IIB), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, and F.
- In one embodiment of Formula (IIB), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (IIB), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (IIB), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH.
- In another embodiment of Formula (IIB), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (IIB), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IIB)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (IIB), which include
- 4-[(imidazo[1,2-a]pyridin-7-ylcarbamoyl)amino]-N-(3-methylbutyl)benzamide; and
pharmaceutically acceptable salts thereof. - In another aspect, the present invention provides compounds of Formula (IIIB)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described in Formula (IB) herein.
- One embodiment pertains to compounds of Formula (IIIB) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (IIIB), X is N or CY1. In another embodiment of Formula (IIIB), X is N. In another embodiment of Formula (IIIB), X is CY1.
- In one embodiment of Formula (IIIB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IIIB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IIIB), X is CY1; and Y1 is Cl. In another embodiment of Formula (IIIB), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (IIIB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIIB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IIIB), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IIIB), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IIIB), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IIIB), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIIB), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (IIIB), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIIB), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (IIIB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIIB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (IIIB), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IIIB), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (IIIB), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IIIB), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (IIIB), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (IIIB), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, and F.
- In one embodiment of Formula (IIIB), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (IIIB), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (IIIB), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH.
- In another embodiment of Formula (IIIB), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (IIIB), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IIIB)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (IIIB), which include
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(3-methylbutyl)benzamide;
- 2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-phenylethyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(morpholin-4-yl)ethyl]benzamide;
- N-(1-hydroxy-2-methylpropan-2-yl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- N-benzyl-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- N-(cyclopentylmethyl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(piperidin-1-yl)propyl]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-phenoxyethyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(pyrrolidin-1-yl)ethyl]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(propan-2-yloxy)ethyl]benzamide;
- N-(2-hydroxy-2-methylpropyl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(2-oxopyrrolidin-1-yl)ethyl]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydrofuran-2-ylmethyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-propylbenzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(morpholin-4-yl)propyl]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-phenylbenzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-methylbutyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(2-oxopyrrolidin-1-yl)propyl]benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydro-2H-pyran-4-ylmethyl)benzamide;
- 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydro-2H-pyran-2-ylmethyl)benzamide;
- N-[(1,1-dioxidotetrahydrothiophen-3-yl)methyl]-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-3,6-dihydropyridine-1 (2H)-carboxylate;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(tetrahydrofuran-3-yl)acetamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea;
- 1-{4-[1-(2-hydroxy-2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(morpholin-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea;
- 1-{4-[1-(ethoxyacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(2-methoxyethoxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea;
- 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(1-methylpiperidin-4-yl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)urea;
- 1-(4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea;
- 2-ethoxy-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(tetrahydro-2H-pyran-4-yl)acetamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(morpholin-4-yl)acetamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(2-methoxyethoxy)acetamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-3-methoxy-2-methylpropanamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}butanamide;
- 4,4,4-trifluoro-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}butanamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}tetrahydro-2H-pyran-4-carboxamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-4-methylpentanamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-1-methylpiperidine-4-carboxamide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}tetrahydro-2H-thiopyran-4-carboxamide 1,1-dioxide;
- N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-1,4-dioxane-2-carboxamide;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}piperidine-1-carboxylate;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-imidazo[1,2-a]pyridin-6-ylurea;
- 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 4-{[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoyl]amino}-N-(tetrahydro-2H-pyran-2-ylmethyl)benzamide; and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (IVB)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (IB).
- One embodiment pertains to compounds of Formula (IVB) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (IVB), X is N or CY1. In another embodiment of Formula (IVB), X is N. In another embodiment of Formula (IVB), X is CY1.
- In one embodiment of Formula (IVB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IVB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IVB), X is CY1; and Y1 is Cl. In another embodiment of Formula (IVB), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (IVB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IVB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IVB), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IVB), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IVB), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IVB), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IVB), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (IVB), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IVB), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (IVB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IVB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (IVB), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IVB), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (IVB), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IVB), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (IVB), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (IVB), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, and F.
- In one embodiment of Formula (IVB), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (IVB), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (IVB), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2CHCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH.
- In another embodiment of Formula (IVB), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (IVB), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IVB)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl; wherein each R1 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (IVB), which include
- 2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)acetamide;
- tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(morpholin-4-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(3-hydroxy-3-methylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea;
- 1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-4-methylpentanamide;
- 3-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)propanamide;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(propan-2-yloxy)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydrofuran-2-yl)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydro-2H-pyran-4-yl)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3-phenylpropanamide;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3R)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}phenyl)urea;
- tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3,6-dihydropyridine-1(2H)-carboxylate;
- tert-butyl (3R)-3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)pyrrolidine-1-carboxylate;
- tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)pyrrolidine-1-carboxylate;
- N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)biphenyl-2-sulfonamide;
- 1-{2-fluoro-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)phenyl]urea;
- 1-(4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}phenyl)urea;
- 1-(4-{[(3R)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)urea;
- 1-(4-{[(3R)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydrofuran-3-ylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}phenyl)urea;
- tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)azetidine-1-carboxylate;
- tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)piperidine-1-carboxylate;
- 1-[4-(1-acetylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethylpropanoyl)pyrrolidin-3-{4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}phenyl)urea;
- 1-{4-[1-(cyclopropylacetyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-[4-(1-benzoylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(propan-2-yloxy)acetyl]pyrrolidin-3-yl}phenyl)urea;
- 1-{4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]phenyl}urea;
- 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(morpholin-4-ylacetyl)pyrrolidin-3-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[5-(piperidin-1-ylcarbonyl)-1,3-thiazol-2-yl]urea;
- 2-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}-N-(3-methylbutyl)-1,3-thiazole-5-carboxamide;
- 1-{4-[(1-acetylazetidin-3-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-2-methylbutanoyl]azetidin-3-yl}oxy)phenyl]urea;
- 1-(4-{[1-(cyclopropylacetyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[(1-benzoylazetidin-3-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(propan-2-yloxy)acetyl]azetidin-3-yl}oxy)phenyl]urea;
- 1-(4-{[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)azetidin-3-yl]oxy}phenyl)urea;
- 1-(4-{[1-(1,4-dioxan-2-ylcarbonyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]oxy}phenyl)urea;
- 1-[4-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-2-methylbutanoyl]piperidin-4-yl}oxy)phenyl]urea;
- 1-(4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[(1-benzoylpiperidin-4-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)phenyl]urea;
- 1-(4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)azetidin-3-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]azetidin-3-yl}phenyl)urea;
- 1-{4-[1-(cyclopropylacetyl)azetidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-[4-(1-benzoylazetidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(propan-2-yloxy)acetyl]azetidin-3-yl}phenyl)urea;
- 1-{4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)azetidin-3-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-phenoxyphenyl)urea;
- 2-cyclopentyl-N-(4-{[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)acetamide;
- tert-butyl 4-(4-{[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]phenyl}urea;
- 1-(4-{[(3R)-1-(2-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(3-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(4-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[4-(trifluoromethyl)benzoyl]pyrrolidin-3-yl}oxy)phenyl]urea;
- 1-(4-{[(3R)-1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(2-chlorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[(3R)-1-(4-chlorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-[4-(1-butanoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methylcyclopropyl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(cyclopropylacetyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]phenyl}urea;
- 1-(4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(phenylacetyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(3-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(4-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[1-(3-fluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[1-(2,4-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[1-(2,5-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[1-(3,4-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{[1-(3,5-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea;
- tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate;
- 1-(4-{1-[(2-chloropyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3-methylbut-2-enoyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methylcyclopent-1-en-1-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(2-ethylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(4-fluorophenoxy)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,4-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,5-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3-methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-oxo-2,3-dihydro-1H-inden-4-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-2-methylbut-2-enoyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(1H-indol-3-ylacetyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)phenyl]urea;
- 1-(4-{1-[(2S)-2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-tetrahydro-2,1-benzoxazol-3-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(4-{1-[(2-chloro-5-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(2-chloro-3-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-(pyridin-2-yl)cyclopropyl]carbonyl}piperidin-4-yl)phenyl]urea;
- 1-(4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-[4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,3-dihydro-1-benzofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxycyclohexyl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-4-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-1,3-benzoxazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(cinnolin-4-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(quinolin-7-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(5,6,7,8-tetrahydroquinolin-3-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-7-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(quinoxalin-2-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-(2-methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-(pyridin-2-yl)prop-2-enoyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(4-chloro-2,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(8-methylimidazo[1,2-a]pyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methyl-4H-furo[3,2-b]pyrrol-5-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(4-chloro-1-ethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-8-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-{4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[3-methyl-1-(prop-2-en-1-yl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)phenyl]urea;
- 1-{4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(5,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3,5-difluoropyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(4-methylpentanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(2-fluoro-4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(2-cyanobenzoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{2-fluoro-4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(thieno[3,2-b]furan-5-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(5-cyclopropylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-[4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4-yl]carbonyl}piperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-{4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxy-5-methylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[4-(propan-2-yl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-5-propyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-yl)propanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(pyrazolo[1,5-a]pyridin-2-ylcarbonyl)piperidin-4-yl]phenyl}urea;
- 1-{4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2-(propan-2-yl)-1,3-oxazol-4-yl]carbonyl}piperidin-4-yl)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-7-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methoxy-5-methylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(5,6-dimethoxypyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2H-indazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2H-indazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea;
- 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2-(trifluoromethyl)furan-3-yl]carbonyl}piperidin-4-yl)phenyl]urea; and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (VB)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (IB).
- One embodiment pertains to compounds of Formula (VB) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (VB), X is N or CY1. In another embodiment of Formula (VB), X is N. In another embodiment of Formula (VB), X is CY1.
- In one embodiment of Formula (VB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VB), X is CY1; and Y1 is Cl. In another embodiment of Formula (VB), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (VB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VB), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VB), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (VB), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VB), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VB), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (VB), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VB), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (VB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (VB), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VB), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (VB), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VB), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (VB), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (VB), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, and F.
- In one embodiment of Formula (VB), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (VB), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (VB), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH.
- In another embodiment of Formula (VB), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (VB), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VB)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (VB), which include
- 4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}-N-(3-methylbutyl)benzamide;
- 2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-4-methylpentanamide;
- 3-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)propanamide;
- N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(propan-2-yloxy)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydrofuran-2-yl)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydro-2H-pyran-4-yl)acetamide;
- N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-3-phenylpropanamide;
- 1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea;
- 1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea; and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (VIB)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (IB).
- One embodiment pertains to compounds of Formula (VIB) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (VIB), X is N or CY1. In another embodiment of Formula (VIB), X is N. In another embodiment of Formula (VIB), X is CY1.
- In one embodiment of Formula (VIB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VIB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VIB), X is CY1; and Y1 is Cl. In another embodiment of Formula (VIB), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (VIB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VIB), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VIB), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (VIB), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VIB), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIB), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (VIB), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIB), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (VIB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (VIB), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIB), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (VIB), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIB), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (VIB), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (VIB), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, and F.
- In one embodiment of Formula (VIB), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (VIB), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (VIB), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2CHCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH. In another embodiment of Formula (VIB), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (VIB), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VIB)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (VIB), which include
- 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4R)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide;
- 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4S)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide;
- 2-{(4R)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- 2-{(4S)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(1,2-oxazol-3-ylacetyl)[(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(5-methyl-1,2-oxazol-3-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1,2-oxazol-5-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1,2-oxazol-4-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(2R)-tetrahydrofuran-2-ylmethyl](1,3-thiazol-4-ylacetyl)amino}-1,3-thiazole-5-carboxamide;
- 2-{[(1,5-dimethyl-1H-pyrazol-3-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1-methyl-1H-pyrazol-4-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- 2-{[(3,5-dimethyl-1,2-oxazol-4-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(1-methyl-1H-pyrazol-4-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1-methyl-1H-pyrrol-2-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- 2-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-1,3-thiazole-5-carboxamide;
- tert-butyl {4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydro-2H-pyran-4-ylacetyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-2-ylacetyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[3-(tetrahydrofuran-2-yl)propanoyl]amino}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(propan-2-yloxy)acetyl]amino}benzamide;
- 4-[(3-cyclopentylpropanoyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(4-methylpentanoyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate;
- 2-{5-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- 4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide;
- 5-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]thiophene-2-carboxamide;
- 2-[(2S)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4R)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide;
- 5-[1-(cyclopropylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[(4R)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]thiophene-2-carboxamide;
- 2-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(5S)-2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(5R)-2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methoxyacetyl)piperidin-4-yl]thiophene-2-carboxamide;
- 5-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- 5-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(1,2-oxazol-5-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 5-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[(4R)-4-hydroxy-2-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[(4S)-4-hydroxy-2-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methylsulfonyl)piperidin-4-yl]thiophene-2-carboxamide;
- 5-[1-(cyclohexylmethyl)-5-ethyl-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methoxy-3,3-dimethylcyclohexyl)methyl]-5-methyl-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- tert-butyl {2-fluoro-4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-propyl-1H-pyrazol-4-yl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(morpholin-4-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-(1-ethyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(1,1-dioxidotetrahydrothiophen-3-yl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 2-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- 4-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-phenylthiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(methylsulfonyl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}pyrrolidine-1-carboxylate;
- 5-{1-[(2R)-2-hydroxypropyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-[(cyclopentylacetyl)amino]-3-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3R)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide;
- 4-[1-(cyclopropylacetyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide;
- 5-[1-(1,4-dioxan-2-ylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(propan-2-yloxy)phenyl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(2-methylpropanoyl)amino]oxetan-3-yl}thiophene-2-carboxamide;
- 5-[3-(benzoylamino)oxetan-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(tetrahydrofuran-3-ylacetyl)amino]oxetan-3-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(pentanoylamino)oxetan-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3R)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}benzamide;
- 5-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- 4-{[(3S)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{[(3S)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(3-methoxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide;
- 4-{[(3S)-1-butanoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide;
- 4-{[(3S)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{[(3S)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{[(3S)-1-(3-hydroxy-3-methylbutanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 2-(4-benzoylpiperazin-1-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(propan-2-yl)piperazin-1-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(2-methoxyethyl)piperazin-1-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-phenyl-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(1,4-dioxan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-(4-hydroxytetrahydro-2H-pyran-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[3-hydroxy-1-(2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-(1-benzoyl-3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}azetidine-1-carboxylate;
- tert-butyl 4-hydroxy-4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate;
- 5-{3-hydroxy-1-[(2S)-2-methylbutanoyl]azetidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[3-hydroxy-1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(3-{[(2S)-2-methylbutanoyl]amino}oxetan-3-yl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1-[1-(3-methylbutanoyl)piperidin-4-yl]-1H-pyrazole-3-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 4-[(1-acetylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]piperidin-4-yl}oxy)benzamide;
- 4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[(1-benzoylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)benzamide;
- 4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}benzamide;
- 4-{[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(morpholin-4-ylacetyl)piperidin-4-yl]oxy}benzamide;
- tert-butyl (3R)-3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}pyrrolidine-1-carboxylate;
- 4-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3,3-difluorocyclobutyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[6-(morpholin-4-yl)pyridin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methyltetrahydro-2H-pyran-2-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropanoyl)amino]cyclobutyl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylbutanoyl)amino]cyclobutyl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-{[(2S)-2-methylbutanoyl]amino}cyclobutyl)thiophene-2-carboxamide;
- 5-[1-(benzoylamino)cyclobutyl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3,3,3-trifluoropropanoyl)amino]cyclobutyl}thiophene-2-carboxamide;
- N-(1-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}cyclobutyl)tetrahydro-2H-pyran-4-carboxamide;
- tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}azetidine-1-carboxylate;
- 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 4-[1-(furan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(piperidin-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-phenoxybenzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide;
- 4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide;
- 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(2,2-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclohexylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide;
- 4-(1-butanoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylpent-2-enoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyloxetan-3-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1-cyanocyclopropyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopentylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-oxobutanoyl)piperidin-4-yl]benzamide;
- 4-{1-[(2,5-dimethylfuran-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(3-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(4-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-propanoylpiperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(2,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide;
- 2-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- 4-[(cyclopentylacetyl)amino]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]azetidin-3-yl}benzamide;
- 4-[1-(cyclopropylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-benzoylazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)azetidin-3-yl]benzamide;
- 5-[4-hydroxy-1-(3-methylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[4-hydroxy-1-(2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3,3-dimethylbutanoyl)-4-hydroxypiperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-(1-benzoyl-4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]azetidin-3-yl}oxy)benzamide;
- 4-{[1-(cyclopropylacetyl)azetidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[(1-benzoylazetidin-3-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- tert-butyl 4-{4-[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-1-ylcarbonyl)benzamide;
- 4-[1-(ethylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopropylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)azetidin-3-yl]benzamide;
- propan-2-yl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate;
- 2-methylpropyl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]piperidin-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-[1-(2-cyano-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3R)-tetrahydrofuran-3-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(cyclopentylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(cyclohexylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(cyclohexylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(furan-3-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(ethylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopropylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(cyclopentylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)azetidin-3-yl]benzamide;
- 4-[1-(cyclopentylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(2,2-dimethylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)azetidin-3-yl]benzamide;
- 4-[1-(2-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(furan-2-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,4-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(2-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)azetidin-3-yl]benzamide;
- 4-[1-(4-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,2-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)azetidin-3-yl]benzamide;
- 4-[1-(3,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyanobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(cyclohexylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)azetidin-3-yl]benzamide;
- 4-[1-(cyclohexylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)azetidin-3-yl]benzamide;
- 4-[1-(furan-3-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrimidin-4-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(2,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]azetidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]azetidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]azetidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)pyrrolidin-3-yl]benzamide;
- 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)piperidin-4-yl]benzamide;
- 4-[1-(cyclopropylsulfonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 5-{(1R)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{(1R)-3-methyl-1-[(tetrahydrofuran-3-ylacetyl)amino]butyl}thiophene-2-carboxamide;
- 5-{(1S)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1-phenylpiperidin-4-yl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(pyridin-2-yl)piperidin-4-yl]-1,3-thiazole-5-carboxamide;
- 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-[1-(2-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylacetyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide;
- 5-[1-(cyclopropylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylacetyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methyl-2-phenylpropanoyl)pyrrolidin-3-yl]benzamide;
- 4-{1-[difluoro(phenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]furan-2-carboxamide;
- 4-[1-(2-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- 5-(1-benzyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide;
- 5-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[4-(2-methylpropyl)phenyl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-2-methylbutanoyl]-1,2,3,6-tetrahydropyridin-4-yl}furan-2-carboxamide;
- 5-[1-(3,3-dimethylbutanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 5-[1-(cyclopropylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{1-[(2-methylpropyl)sulfonyl]pyrrolidin-3-yl}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(phenylsulfonyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]-1,2,3,6-tetrahydropyridin-4-yl}furan-2-carboxamide;
- tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidine-1-carboxylate;
- 5-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(4-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-{1-[(3-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(3,5-difluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(2-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(4-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- 5-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- 5-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-4-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrazol-4-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- 5-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2E)-2-methylpent-2-enoyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- 5-{1-[(2,5-dimethylfuran-3-yl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-propanoylpyrrolidin-3-yl)thiophene-2-carboxamide;
- 5-{1-[(1-cyanocyclopropyl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-(1-butanoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-[1-(2,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(thiophen-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methylpiperidin-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 5-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyrazin-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylthiophen-2-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-3-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrazol-5-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide;
- 5-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(phenylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide;
- 2-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- 5-[1-(2-fluorobenzoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 2-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide;
- 2-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- tert-butyl 4-[2-(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)ethyl]piperazine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-5-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutyl)-1H-pyrazol-5-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{[2-(2-methylpropyl)pyrrolidin-1-yl]carbonyl}thiophene-2-carboxamide;
- 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 5-(1-benzyl-3-cyclopropyl-1H-pyrazol-5-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(2-methoxyphenyl)acetyl]amino}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(phenylacetyl)amino]benzamide;
- 4-(benzoylamino)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 2,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide;
- 3,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide;
- 3,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide;
- 2,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide;
- 2-fluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide;
- N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-3-methoxybenzamide;
- 4-{[(2-fluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[2-(2-methylpropyl)pyrrolidin-1-yl]carbonyl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-methyl-2-(piperazin-1-yl)propanoyl]piperidin-4-yl}thiophene-2-carboxamide;
- N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-2-methoxybenzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(phenylsulfonyl)benzamide;
- 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tricyclo[3.3.1.1˜3,7˜]dec-1-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 5-(1-benzyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-oxatricyclo[3.3.1.1˜3,7˜]dec-1-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- 4-{[(2,5-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{[(2,4-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 5-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[3-cycloproopyl-1-(2-methoxyethyl)-1H-pyrazol-5-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-{[difluoro(phenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(2-methyl-2-phenylpropanoyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-5-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-methyl-3-(2-methylpropyl)-1H-pyrazol-5-yl]thiophene-2-carboxamide;
- 5-[1-benzyl-3-(2-methylpropyl)-1H-pyrazol-5-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(2,5-difluorobenzyl)-N′-(imidazo[1,2-a]pyridin-7-ylmethyl)benzene-1,4-dicarboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[2-(propan-2-yl)pyrrolidin-1-yl]carbonyl}benzamide;
- 4-{1-[(2-chloropyridin-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbut-2-enoyl)piperidin-4-yl]benzamide;
- 4-[1-(3-fluoro-4-methoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopent-1-en-1-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-[1-(2-ethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(4-fluorophenoxy)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxyphenyl)acetyl]piperidin-4-yl}benzamide;
- 4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(2-acetylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(methoxymethyl)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenylpropanoyl)piperidin-4-yl]benzamide;
- 4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[(2-methylpropyl)sulfonyl]acetyl}piperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenoxypropanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-({[(1R,2S)-2-methylcyclohexyl]oxy}acetyl)piperidin-4-yl]benzamide;
- 4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methoxyphenyl)acetyl]piperidin-4-yl}benzamide;
- 4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylbut-2-enoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxy-5-methylphenyl)acetyl]piperidin-4-yl}benzamide;
- 4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrrolidin-1-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)benzamide;
- 4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-2,1-benzoxazol-3-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(2-chloro-3-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(pyridin-2-yl)cyclopropyl]carbonyl}piperidin-4-yl)benzamide;
- 4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,4-dihydro-2H-chromen-6-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(cyclohexyloxy)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(2-chloropyridin-3-yl)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(5-cyclopropyl-1,2-oxazol-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2H-chromen-3-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3,5-difluoropyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxycyclohexyl)carbonyl]piperidin-4-yl}benzamide;
- 4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-4-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-1,3-benzoxazol-6-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thieno[3,2-b]pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinolin-7-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(5,6,7,8-tetrahydroquinolin-3-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-7-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinoxalin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-3-(2-methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-3-(pyridin-2-yl)prop-2-enoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(8-methylimidazo[1,2-a]pyridin-2-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methyl-4H-furo[3,2-b]pyrrol-5-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-8-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[3-methyl-1-(prop-2-en-1-yl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)benzamide;
- 4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)pyrimidin-4-yl]carbonyl}piperidin-4-yl)benzamide;
- 4-{1-[(5,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)tetrahydro-2H-pyran-4-yl]carbonyl}piperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxy-6-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(2-chloro-5-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-methyl-5-(propan-2-yl)furan-3-yl]carbonyl}piperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(piperidin-1-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-N,N-dimethylpiperidine-1-carboxamide;
- 5-{1-[2,2-dimethyl-3-(piperazin-1-yl)propyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3-amino-2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-{1-[(2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-indazol-6-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(5-cyclopropylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]acetyl}piperidin-4-yl)benzamide;
- 4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-1-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxy-5-methylpyridin-2-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[4-(propan-2-yl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-5-propyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-yl)propanoyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2,3-dihydro-1-benzofuran-7-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)-1,3-thiazol-4-yl]carbonyl}piperidin-4-yl)benzamide;
- 4-(1-{[1-(difluoromethyl)-5-methyl-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(4-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazolo[1,5-a]pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)-1,3-oxazol-4-yl]carbonyl}piperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxy-5-methylpyridin-3-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(5,6-dimethoxypyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2H-indazol-4-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2H-indazol-6-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-indazol-4-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(trifluoromethyl)furan-3-yl]carbonyl}piperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrimidin-4-yl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpyrimidin-4-yl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[6-(trifluoromethyl)pyrimidin-4-yl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide;
- 5-[1-({3,5-dimethyl-7-[2-(methylamino)ethoxy]tricyclo[3.3.1.13,7]dec-1-yl}methyl)-5-methyl-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-({4-methyl-1-[2-(piperazin-1-yl)ethyl]piperidin-4-yl}methyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- S-(2-{4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidin-1-yl}-2-oxoethyl)-L-cysteine;
- 5-(1-{[1-(15-amino-4,7,10,13-tetraoxapentadecan-1-oyl)-4-methylpiperidin-4-yl]methyl}-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- S-{2-[(3-{4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidin-1-yl}-3-oxopropyl)amino]-2-oxoethyl}-L-cysteine; and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (VIIB)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (IB).
- One embodiment pertains to compounds of Formula (VIIB) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR1, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2CHCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (VIIB), X is N or CY1. In another embodiment of Formula (VIIB), X is N. In another embodiment of Formula (VIIB), X is CY1.
- In one embodiment of Formula (VIIB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VIIB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VIIB), X is CY1; and Y1 is Cl. In another embodiment of Formula (VIIB), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (VIIB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VIIB), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VIIB), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (VIIB), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VIIB), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIB), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (VIIB), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIB), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (VIIB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (VIIB), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIB), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (VIIB), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIIB), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (VIIB), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIB), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, and F.
- In one embodiment of Formula (VIIB), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (VIIB), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (VIIB), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH.
- In another embodiment of Formula (VIIB), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (VIIB), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VIIB)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (VIIB), which include
- 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 2-[(4-cyanobenzyl)(3-methylbutanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(3-methylbutyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydrofuran-2-ylacetyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydro-2H-pyran-4-ylacetyl)amino]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(morpholin-4-ylacetyl)amino]benzamide;
- 4-[(3-cyclopentylpropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[(propan-2-yloxy)acetyl]amino}benzamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenyl}-3,6-dihydropyridine-1 (2H)-carboxylate;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(3-phenylpyrrolidin-1-yl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methylbutyl)amino]-1,3-thiazole-5-carboxamide;
- 2-(1,3-dihydro-2H-isoindol-2-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- 4-[1-(2-hydroxy-2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(morpholin-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-3-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-2-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[3-(tetrahydrofuran-2-yl)propanoyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide;
- 4-[1-(cyclopentylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-3-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- 4-[1-(1,4-dioxan-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[(2-methoxyethoxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide;
- 4-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 4-{1-[(4,4-difluorocyclohexyl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 2-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[2-oxo-4-(tetrahydrofuran-3-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(2-oxo-5-phenyl-1,3-oxazolidin-3-yl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methyl-1,3-thiazol-5-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methyl-1,3-thiazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(3-methyl-1,2-oxazol-5-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- 2-{[3-(3-chloro-1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(3-methoxy-1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- 2-{[(3,5-dimethyl-1,2-oxazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- 2-{[3-(3,5-dimethyl-1,2-oxazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1-methyl-1H-pyrazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(4-methyl-1,3-thiazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-2-ylmethyl)(1H-tetrazol-5-ylacetyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(1,2-oxazol-3-ylacetyl)(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1,2-oxazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-2-ylmethyl) [3-(1,3-thiazol-2-yl)propanoyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methylbutanoyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydrofuran-3-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-3-ylmethyl)(tetrahydro-2H-pyran-4-ylcarbonyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydrofuran-3-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-3-ylcarbonyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydro-2H-pyran-4-ylcarbonyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(3-methoxypropanoyl)[(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-3-ylcarbonyl) [(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2R)-tetrahydrofuran-2-ylmethyl](tetrahydro-2H-pyran-4-ylcarbonyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(3-methoxypropanoyl)[(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-3-ylcarbonyl) [(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2S)-tetrahydrofuran-2-ylmethyl](tetrahydro-2H-pyran-4-ylcarbonyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydro-2H-pyran-4-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-({[2-(propan-2-yloxy)ethyl]carbamoyl}[(2R)-tetrahydrofuran-2-ylmethyl]amino)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl][(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-({[2-(propan-2-yloxy)ethyl]carbamoyl}[(2S)-tetrahydrofuran-2-ylmethyl]amino)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydrofuran-3-ylmethyl)amino]-1,3-thiazole-5-carboxamide;
- 2-[5-(4-chlorophenyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide;
- 4-[(1-acetylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 4-{[1-(cyclopropylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}benzamide;
- 4-{[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide;
- 4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)benzamide;
- 4-[(1-butanoylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(3-methoxy-2-methylpropanoyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}benzamide;
- 4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropanoyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(cyclohexylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(2R)-2-hydroxybutyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(1-methyl-1H-pyrazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- 2-{[(1,3-dimethyl-1H-pyrazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1-methyl-1H-pyrrol-2-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide;
- 2-{[(1,5-dimethyl-1H-pyrazol-3-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-2-ylmethyl)(1,3-thiazol-4-ylacetyl)amino]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 4-[(4-cyanobenzyl)(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 4-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide;
- N-[(3-chloroimidazo[1,2-a]pyridin-6-yl)methyl]-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide;
- 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide;
- 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(1,4-dioxan-2-ylmethyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide;
- 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide;
- 5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide;
- 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-methylpropanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3-methylbutanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- 5-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-{1-[(1-methylpiperidin-4-yl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-cyanobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(propan-2-ylsulfonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(phenylsulfonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide;
- 4-(phenylsulfonyl)-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-(phenylsulfonyl)benzamide; and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (VIIIB)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (I).
- One embodiment pertains to compounds of Formula (VIIIB) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- In one embodiment of Formula (VIIIB), X is N or CY1. In another embodiment of Formula (VIIIB), X is N. In another embodiment of Formula (VIIIB), X is CY1.
- In one embodiment of Formula (VIIIB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VIIIB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VIIIB), X is CY1; and Y1 is Cl. In another embodiment of Formula (VIIIB), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (VIIIB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIIB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VIIIB), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VIIIB), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (VIIIB), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (VIIIB), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIIB), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (VIIIB), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIIB), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (VIIIB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIIB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (VIIIB), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIIB), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (VIIIB), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIIIB), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (VIIIB), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (VIIIB), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, and F.
- In one embodiment of Formula (VIIIB), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (VIIIB), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (VIIIB), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2CHCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH. In another embodiment of Formula (VIIIB), R11, at each occurrence, is independently alkyl. In another embodiment of Formula (VIIIB), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VIIIB)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- with the proviso that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent.
- Still another embodiment pertains to compounds having Formula (VIIIB), which include
- tert-butyl 4-[4-(imidazo[1,2-a]pyridin-7-ylcarbamoyl)phenyl]piperidine-1-carboxylate; and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (IXB)
- and pharmaceutically acceptable salts thereof; wherein X and R3 are as described herein for Formula (I).
- One embodiment pertains to compounds of Formula (IXB) or pharmaceutically acceptable salts thereof;
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- with the provisos that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent; and
- when X is CY1 and Y1 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenyl.
- In one embodiment of Formula (IXB), X is N or CY1. In another embodiment of Formula (IXB), X is N. In another embodiment of Formula (IXB), X is CY1.
- In one embodiment of Formula (IXB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IXB), X is CY1; and Y1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IXB), X is CY1; and Y1 is Cl. In another embodiment of Formula (IXB), X is CY1; and Y1 is hydrogen.
- In one embodiment of Formula (IXB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH2, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, OR4, SR4, S(O)R4, SO2R4, C(O)R4, CO(O)R4, OC(O)R4, OC(O)OR4, NH2, NHR4, N(R4)2, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NR4S(O)2R4, NHC(O)OR4, NR4C(O)OR4, NHC(O)NH2, NHC(O)NHR4, NHC(O)N(R4)2, NR4C(O)NHR4, NR4C(O)N(R4)2, C(O)NH2, C(O)NHR4, C(O)N(R4)2, C(O)NHOH, C(O)NHOR4, C(O)NHSO2R4, C(O)NR4SO2R4, SO2NH2, SO2NHR4, SO2N(R4)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR4, C(N)N(R4)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IXB), R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IXB), R3 is phenyl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, and C(O)NHR4; and wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IXB), R3 is 5-6 membered heteroaryl; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I. In another embodiment of Formula (IXB), R3 is thienyl; wherein each R3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)NHR4, C(O)NHR4, F, Cl, Br and I.
- In one embodiment of Formula (IXB), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IXB), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (IXB), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IXB), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (IXB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IXB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (IXB), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (IXB), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (IXB), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IXB), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (IXB), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (IXB), R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, and F.
- In one embodiment of Formula (IXB), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (IXB), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (IXB), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH.
- In another embodiment of Formula (IXB), R1, at each occurrence, is independently alkyl. In another embodiment of Formula (IXB), R11, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IXB)
- wherein
- X is N or CY1;
- Y1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
- R3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R4, OR4, SO2R4, C(O)R4, NHC(O)R4, NR4C(O)R4, NHS(O)2R4, NHC(O)OR4, C(O)NHR4, F, Cl, Br and I; wherein each R3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R4, C(O)R4, NHR4, NHC(O)R4, NR4C(O)R4, NHC(O)OR4, NR4C(O)OR4, C(O)NHR4, F, Cl, Br and I;
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6, aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH;
- with the provisos that
- when X is CY1 and Y1 is hydrogen; and R3 is thiazolyl; the R3 thiazolyl is substituted with one substituent; and when X is CY1 and Y1 is hydrogen; and R3 is phenyl; the R3 phenyl is not substituted at the para position with phenyl.
- Still another embodiment pertains to compounds having Formula (IXB), which include
- 2-[(4-cyanobenzyl)(3-methylbutanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide;
- 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide;
- 2-cyclopentyl-N-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}acetamide;
- tert-butyl 4-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}-3,6-dihydropyridine-1 (2H)-carboxylate;
- tert-butyl 4-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoyl)phenyl]piperidine-1-carboxylate;
- tert-butyl 4-{4-[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoyl]phenyl}piperidine-1-carboxylate; and pharmaceutically acceptable salts thereof.
- In another aspect, the present invention provides compounds of Formula (XB)
- and pharmaceutically acceptable salts thereof; wherein R4 is as described herein for Formula (IB).
- One embodiment pertains to compounds of Formula (XB) or pharmaceutically acceptable salts thereof;
- wherein
- R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R7, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I;
- R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I; and
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
- R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2CHCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH.
- In one embodiment of Formula (XB), R4, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, SR5, S(O)R5, SO2R5, C(O)R5, CO(O)R5, OC(O)R5, OC(O)OR5, NH2, NHR5, N(R5)2, NHC(O)R5, NR5C(O)R5, NHS(O)2R5, NR5S(O)2R5, NHC(O)OR5, NR5C(O)OR5, NHC(O)NH2, NHC(O)NHR5, NHC(O)N(R5)2, NR5C(O)NHR5, NR5C(O)N(R5)2, C(O)NH2, C(O)NHR5, C(O)N(R5)2, C(O)NHOH, C(O)NHOR5, C(O)NHSO2R5, C(O)NR5SO2R5, SO2NH2, SO2NHR5, SO2N(R5)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR5, C(N)N(R5)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SR6, S(O)R6, SO2R6, C(O)R6, CO(O)R6, OC(O)R6, OC(O)OR6, NH2, NHR6, N(R6)2, NHC(O)R6, NR6C(O)R6, NHS(O)2R6, NR6S(O)2R6, NHC(O)OR6, NR6C(O)OR6, NHC(O)NH2, NHC(O)NHR6, NHC(O)N(R6)2, NR6C(O)NHR6, NR6C(O)N(R6)2, C(O)NH2, C(O)NHR6, C(O)N(R6)2, C(O)NHOH, C(O)NHOR6, C(O)NHSO2R6, C(O)NR6SO2R6, SO2NH2, SO2NHR6, SO2N(R6)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR6, C(N)N(R6)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (XB), R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, C(O)N(R6)2, OH, and F.
- In another embodiment of Formula (XB), R5, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, SR7, S(O)R7, SO2R7, C(O)R7, CO(O)R7, OC(O)R7, OC(O)OR7, NH2, NHR7, N(R7)2, NHC(O)R7, NR7C(O)R7, NHS(O)2R, NR7S(O)2R7, NHC(O)OR7, NR7C(O)OR7, NHC(O)NH2, NHC(O)NHR7, NHC(O)N(R7)2, NR7C(O)NHR7, NR7C(O)N(R7)2, C(O)NH2, C(O)NHR7, C(O)N(R7)2, C(O)NHOH, C(O)NHOR7, C(O)NHSO2R7, C(O)NR7SO2R7, SO2NH2, SO2NHR7, SO2N(R7)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR7, C(N)N(R7)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, SR8, S(O)R8, SO2R8, C(O)R8, CO(O)R8, OC(O)R8, OC(O)OR8, NH2, NHR8, N(R8)2, NHC(O)R8, NR8C(O)R8, NHS(O)2R8, NR8S(O)2R8, NHC(O)OR8, NR8C(O)OR8, NHC(O)NH2, NHC(O)NHR8, NHC(O)N(R8)2, NR8C(O)NHR8, NR8C(O)N(R8)2, C(O)NH2, C(O)NHR8, C(O)N(R8)2, C(O)NHOH, C(O)NHOR8, C(O)NHSO2R8, C(O)NR8SO2R8, SO2NH2, SO2NHR8, SO2N(R8)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR8, C(N)N(R8)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (XB), R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, and OH; wherein each R5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I.
- In one embodiment of Formula (XB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SR9, S(O)R9, SO2R9, C(O)R9, CO(O)R9, OC(O)R9, OC(O)OR9, NH2, NHR9, N(R9)2, NHC(O)R9, NR9C(O)R9, NHS(O)2R9, NR9S(O)2R9, NHC(O)OR9, NR9C(O)OR9, NHC(O)NH2, NHC(O)NHR9, NHC(O)N(R9)2, NR9C(O)NHR9, NR9C(O)N(R9)2, C(O)NH2, C(O)NHR9, C(O)N(R9)2, C(O)NHOH, C(O)NHOR9, C(O)NHSO2R9, C(O)NR9SO2R9, SO2NH2, SO2NHR9, SO2N(R9)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR9, C(N)N(R9)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, SR10, S(O)R10, SO2R10, C(O)R10, CO(O)R10, OC(O)R10, OC(O)OR10, NH2, NHR10, N(R10)2, NHC(O)R10, NR10C(O)R10, NHS(O)2R10, NR10S(O)2R10, NHC(O)OR10, NR10C(O)OR10, NHC(O)NH2, NHC(O)NHR10, NHC(O)N(R10)2, NR10C(O)NHR10, NR10C(O)N(R10)2, C(O)NH2, C(O)NHR10, C(O)N(R10)2, C(O)NHOH, C(O)NHOR10, C(O)NHSO2R10, C(O)NR10SO2R10, SO2NH2, SO2NHR10, SO2N(R10)2, C(O)H, C(O)OH, C(N)NH2, C(N)NHR10, C(N)N(R10)2, CNOH, CNOCH3, OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (XB), R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, CN, F, Cl, Br and I.
- In one embodiment of Formula (XB), R7, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N3, NO2, F, Cl, Br and I; wherein each R7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N3, NO2, F, Cl, Br and I. In another embodiment of Formula (XB), R7, at each occurrence, is alkyl or heterocyclyl.
- In one embodiment of Formula (XB), R8, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (XB), R8, at each occurrence, is independently alkyl.
- In one embodiment of Formula (XB), R9, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO2, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, OC(O)R11, NH2, NHR11, N(R11)2, NHC(O)R11, NR11C(O)R11, C(O)NH2, C(O)NHR11, C(O)N(R11)2, C(O)H, C(O)OH, COH, CN, NO2, F, Cl, Br and I. In another embodiment of Formula (XB), R9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R11, and F.
- In one embodiment of Formula (XB), R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (XB), R10, at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
- In one embodiment of Formula (XB), R11, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH. In another embodiment of Formula (XB), R1, at each occurrence, is independently alkyl. In another embodiment of Formula (XB), R1, at each occurrence, is independently cycloalkyl.
- One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (XB)
- wherein
- R4, at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R5, OR5, C(O)R5, NHC(O)R5, OH, F, Cl, Br and I; wherein each R4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R6, OR6, SO2R6, C(O)R6, CO(O)R6, C(O)C(O)R6, NHC(O)R6, NHC(O)NHR6, C(O)N(R6)2, OH, F, Cl, Br and I;
- R5, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R7, OR7, OH, F, Cl, Br and I; wherein each R5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R8, OR8, CN, F, Cl, Br and I;
- R6, at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R9, OR9, SO2R9, NH2, N(R9)2, OH, F, Cl, Br and I; wherein each R6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R10, OR10, C(O)R10, CN, F, and Cl;
- R7, at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
- R8, at each occurrence, is independently alkyl;
- R9, at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R11, OR11, C(O)R11, CO(O)R, CN, F, Cl, Br and I;
- R10, at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
- R11, at each occurrence, is independently cycloalkyl or alkyl; wherein each R11 alkyl is optionally substituted with NH(CH3), heterocyclyl, SCH2CH(NH2)C(O)OH, OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2NH2, or NHC(O)CH2CH(NH2)C(O)OH.
- Still another embodiment pertains to compounds having Formula (XB), which include
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate;
- 4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide;
- 4-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-phenylthiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(methylsulfonyl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}pyrrolidine-1-carboxylate;
- 5-{1-[(2R)-2-hydroxypropyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-[(cyclopentylacetyl)amino]-3-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3R)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide;
- 4-[1-(cyclopropylacetyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide;
- 5-[1-(1,4-dioxan-2-ylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(propan-2-yloxy)phenyl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(2-methylpropanoyl)amino]oxetan-3-yl}thiophene-2-carboxamide;
- 5-[3-(benzoylamino)oxetan-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(tetrahydrofuran-3-ylacetyl)amino]oxetan-3-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(pentanoylamino)oxetan-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3R)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}benzamide;
- 5-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- 4-{[(3S)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{[(3S)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(3-methoxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide;
- 4-{[(3S)-1-butanoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide;
- 4-{[(3S)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{[(3S)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{[(3S)-1-(3-hydroxy-3-methylbutanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 2-(4-benzoylpiperazin-1-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(propan-2-yl)piperazin-1-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(2-methoxyethyl)piperazin-1-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-phenyl-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxamide;
- tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(1,4-dioxan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-(4-hydroxytetrahydro-2H-pyran-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[3-hydroxy-1-(2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-(1-benzoyl-3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}azetidine-1-carboxylate;
- tert-butyl 4-hydroxy-4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate;
- 5-{3-hydroxy-1-[(2S)-2-methylbutanoyl]azetidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[3-hydroxy-1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(3-{[(2S)-2-methylbutanoyl]amino}oxetan-3-yl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1-[1-(3-methylbutanoyl)piperidin-4-yl]-1H-pyrazole-3-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 4-[(1-acetylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]piperidin-4-yl}oxy)benzamide;
- 4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[(1-benzoylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)benzamide;
- 4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}benzamide;
- 4-{[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(morpholin-4-ylacetyl)piperidin-4-yl]oxy}benzamide;
- tert-butyl (3R)-3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}pyrrolidine-1-carboxylate;
- 4-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(3,3-difluorocyclobutyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[6-(morpholin-4-yl)pyridin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methyltetrahydro-2H-pyran-2-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropanoyl)amino]cyclobutyl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylbutanoyl)amino]cyclobutyl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-{[(2S)-2-methylbutanoyl]amino}cyclobutyl)thiophene-2-carboxamide;
- 5-[1-(benzoylamino)cyclobutyl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3,3,3-trifluoropropanoyl)amino]cyclobutyl}thiophene-2-carboxamide;
- N-(1-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}cyclobutyl)tetrahydro-2H-pyran-4-carboxamide;
- tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}azetidine-1-carboxylate;
- 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide;
- 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide;
- 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide;
- 4-[1-(furan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(piperidin-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-phenoxybenzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide;
- 4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide;
- 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(2,2-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclohexylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide;
- 4-(1-butanoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylpent-2-enoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyloxetan-3-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-{1-[(1-cyanocyclopropyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopentylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-oxobutanoyl)piperidin-4-yl]benzamide;
- 4-{1-[(2,5-dimethylfuran-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]piperidin-4-yl}benzamide;
- 4-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(3-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)piperidin-4-yl]benzamide;
- 4-[1-(4-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-propanoylpiperidin-4-yl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)piperidin-4-yl]benzamide;
- 4-[1-(2,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide;
- 5-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide;
- 2-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide;
- 4-[(cyclopentylacetyl)amino]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]azetidin-3-yl}benzamide;
- 4-[1-(cyclopropylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-(1-benzoylazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)azetidin-3-yl]benzamide;
- 5-[4-hydroxy-1-(3-methylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[4-hydroxy-1-(2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-[1-(3,3-dimethylbutanoyl)-4-hydroxypiperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 5-(1-benzoyl-4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]azetidin-3-yl}oxy)benzamide;
- 4-{[1-(cyclopropylacetyl)azetidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[(1-benzoylazetidin-3-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- tert-butyl 4-{4-[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-1-ylcarbonyl)benzamide;
- 4-[1-(ethylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopropylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)azetidin-3-yl]benzamide;
- propan-2-yl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate;
- 2-methylpropyl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]piperidin-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide;
- N-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- 5-[1-(2-cyano-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
- 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3R)-tetrahydrofuran-3-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(cyclopentylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(cyclohexylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(cyclohexylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(furan-3-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]pyrrolidin-3-yl}benzamide;
- 4-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]pyrrolidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)pyrrolidin-3-yl]benzamide;
- 4-[1-(ethylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(cyclopropylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)pyrrolidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(cyclopentylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)azetidin-3-yl]benzamide;
- 4-[1-(cyclopentylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(2,2-dimethylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)azetidin-3-yl]benzamide;
- 4-[1-(2-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(furan-2-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,4-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(2-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)azetidin-3-yl]benzamide;
- 4-[1-(4-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,2-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,5-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(4-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)azetidin-3-yl]benzamide;
- 4-[1-(3,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3-cyanobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(cyclohexylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)azetidin-3-yl]benzamide;
- 4-[1-(cyclohexylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)azetidin-3-yl]benzamide;
- 4-[1-(furan-3-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrimidin-4-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]azetidin-3-yl}benzamide;
- 4-[1-(2,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)azetidin-3-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]azetidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]azetidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]azetidin-3-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)pyrrolidin-3-yl]benzamide;
- 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)piperidin-4-yl]benzamide;
- 4-[1-(cyclopropylsulfonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 5-{(1R)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{(1R)-3-methyl-1-[(tetrahydrofuran-3-ylacetyl)amino]butyl}thiophene-2-carboxamide;
- 5-{(1S)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1-phenylpiperidin-4-yl)-1,3-thiazole-5-carboxamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(pyridin-2-yl)piperidin-4-yl]-1,3-thiazole-5-carboxamide;
- 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
- 4-[1-(2-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- 4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylacetyl)piperidin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrimidin-4-yl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpyrimidin-4-yl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide;
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[6-(trifluoromethyl)pyrimidin-4-yl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide; and pharmaceutically acceptable salts thereof.
- Another embodiment comprises pharmaceutical compositions comprising a compound having Formula (I) and an excipient.
- Still another embodiment comprises methods of treating cancer in a mammal comprising administering thereto a therapeutically acceptable amount of a compound having Formula (I).
- Still another embodiment pertains to compositions for treating diseases during which NAMPT is expressed, said compositions comprising an excipient and a therapeutically effective amount of the compound having Formula (I).
- Still another embodiment pertains to methods of treating disease in a patient during which NAMPT is expressed, said methods comprising administering to the patient a therapeutically effective amount of a compound having Formula (I).
- Still another embodiment pertains to compositions for treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia, said compositions comprising an excipient and a therapeutically effective amount of the compound having Formula (I).
- Still another embodiment pertains to methods of treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia in a patient, said methods comprising administering to the patient a therapeutically effective amount of a compound having Formula (I).
- Still another embodiment pertains to compositions for treating diseases during which NAMPT is expressed, said compositions comprising an excipient and a therapeutically effective amount of the compound having Formula (I) and a therapeutically effective amount of one additional therapeutic agent or more than one additional therapeutic agent.
- Still another embodiment pertains to methods of treating disease in a patient during which NAMPT is expressed, said methods comprising administering to the patient a therapeutically effective amount of a compound having Formula (I) and a therapeutically effective amount of one additional therapeutic agent or more than one additional therapeutic agent.
- Still another embodiment pertains to compositions for treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia, said compositions comprising an excipient and a therapeutically effective amount of the compound having Formula (I) and a therapeutically effective amount of one additional therapeutic agent or more than one additional therapeutic agent.
- Still another embodiment pertains to methods of treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia in a patient, said methods comprising administering to the patient a therapeutically effective amount of the compound having Formula (I) and a therapeutically effective amount of one additional therapeutic agent or more than one additional therapeutic agent.
- Metabolites of compounds having Formula (I), produced by in vitro or in vivo metabolic processes, may also have utility for treating diseases associated with NAMPT.
- Certain precursor compounds which may be metabolized in vitro or in vivo to form compounds having Formula (I) may also have utility for treating diseases associated with NAMPT.
- Compounds having Formula (I) may exist as acid addition salts, basic addition salts or zwitterions. Salts of the compounds are prepared during isolation or following purification of the compounds. Acid addition salts of the compounds are those derived from the reaction of the compounds with an acid. For example, the acetate, adipate, alginate, bicarbonate, citrate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, camphorate, camphorsufonate, digluconate, formate, fumarate, glycerophosphate, glutamate, hemisulfate, heptanoate, hexanoate, hydrochloride, hydrobromide, hydroiodide, lactobionate, lactate, maleate, mesitylenesulfonate, methanesulfonate, naphthylenesulfonate, nicotinate, oxalate, pamoate, pectinate, persulfate, phosphate, picrate, propionate, succinate, tartrate, thiocyanate, trichloroacetic, trifluoroacetic, para-toluenesulfonate, and undecanoate salts of the compounds are contemplated as being embraced by this invention. Basic addition salts of the compounds are those derived from the reaction of the compounds with the hydroxide, carbonate or bicarbonate of cations such as lithium, sodium, potassium, calcium, and magnesium.
- The compounds having Formula (I) may be administered, for example, bucally, ophthalmically, orally, osmotically, parenterally (intramuscularly, intraperitoneally intrasternally, intravenously, subcutaneously), rectally, topically, transdermally or vaginally.
- Therapeutically effective amounts of compounds having Formula (I) depend on the recipient of the treatment, the disorder being treated and the severity thereof, the composition containing the compound, the time of administration, the route of administration, the duration of treatment, the compound potency, its rate of clearance and whether or not another drug is co-administered. The amount of a compound of this invention having Formula (I) used to make a composition to be administered daily to a patient in a single dose or in divided doses is from about 0.03 to about 200 mg/kg body weight. Single dose compositions contain these amounts or a combination of submultiples thereof.
- Compounds having Formula (I) may be administered with or without an excipient. Excipients include, for example, encapsulating materials or additives such as absorption accelerators, antioxidants, binders, buffers, coating agents, coloring agents, diluents, disintegrating agents, emulsifiers, extenders, fillers, flavoring agents, humectants, lubricants, perfumes, preservatives, propellants, releasing agents, sterilizing agents, sweeteners, solubilizers, wetting agents and mixtures thereof.
- Excipients for preparation of compositions comprising a compound having Formula (I) to be administered orally in solid dosage form include, for example, agar, alginic acid, aluminum hydroxide, benzyl alcohol, benzyl benzoate, 1,3-butylene glycol, carbomers, castor oil, cellulose, cellulose acetate, cocoa butter, corn starch, corn oil, cottonseed oil, cross-povidone, diglycerides, ethanol, ethyl cellulose, ethyl laureate, ethyl oleate, fatty acid esters, gelatin, germ oil, glucose, glycerol, groundnut oil, hydroxypropylmethyl cellulose, isopropanol, isotonic saline, lactose, magnesium hydroxide, magnesium stearate, malt, mannitol, monoglycerides, olive oil, peanut oil, potassium phosphate salts, potato starch, povidone, propylene glycol, Ringer's solution, safflower oil, sesame oil, sodium carboxymethyl cellulose, sodium phosphate salts, sodium lauryl sulfate, sodium sorbitol, soybean oil, stearic acids, stearyl fumarate, sucrose, surfactants, talc, tragacanth, tetrahydrofurfuryl alcohol, triglycerides, water, and mixtures thereof. Excipients for preparation of compositions comprising a compound of this invention having Formula (I) to be administered ophthalmically or orally in liquid dosage forms include, for example, 1,3-butylene glycol, castor oil, corn oil, cottonseed oil, ethanol, fatty acid esters of sorbitan, germ oil, groundnut oil, glycerol, isopropanol, olive oil, polyethylene glycols, propylene glycol, sesame oil, water and mixtures thereof. Excipients for preparation of compositions comprising a compound of this invention having Formula (I) to be administered osmotically include, for example, chlorofluorohydrocarbons, ethanol, water and mixtures thereof. Excipients for preparation of compositions comprising a compound of this invention having Formula (I) to be administered parenterally include, for example, 1,3-butanediol, castor oil, corn oil, cottonseed oil, dextrose, germ oil, groundnut oil, liposomes, oleic acid, olive oil, peanut oil, Ringer's solution, safflower oil, sesame oil, soybean oil, U.S.P. or isotonic sodium chloride solution, water and mixtures thereof. Excipients for preparation of compositions comprising a compound of this invention having Formula (I) to be administered rectally or vaginally include, for example, cocoa butter, polyethylene glycol, wax and mixtures thereof.
- Compounds having Formula (I) are expected to be useful when used with alkylating agents, angiogenesis inhibitors, antibodies, antimetabolites, antimitotics, antiproliferatives, antivirals, aurora kinase inhibitors, apoptosis promoters (for example, Bcl-xL, Bcl-w and Bfl-1) inhibitors, activators of death receptor pathway, Bcr-Abl kinase inhibitors, BiTE (Bi-Specific T cell Engager) antibodies, antibody drug conjugates, biologic response modifiers, cyclin-dependent kinase inhibitors, cell cycle inhibitors, cyclooxygenase-2 inhibitors, DVDs, leukemia viral oncogene homolog (ErbB2) receptor inhibitors, growth factor inhibitors, heat shock protein (HSP)-90 inhibitors, histone deacetylase (HDAC) inhibitors, hormonal therapies, immunologicals, inhibitors of inhibitors of apoptosis proteins (IAPs), intercalating antibiotics, kinase inhibitors, kinesin inhibitors, Jak2 inhibitors, mammalian target of rapamycin inhibitors, microRNA's, mitogen-activated extracellular signal-regulated kinase inhibitors, multivalent binding proteins, non-steroidal anti-inflammatory drugs (NSAIDs), poly ADP (adenosine diphosphate)-ribose polymerase (PARP) inhibitors, platinum chemotherapeutics, polo-like kinase (Plk) inhibitors, phosphoinositide-3 kinase (PI3K) inhibitors, proteosome inhibitors, purine analogs, pyrimidine analogs, receptor tyrosine kinase inhibitors, retinoids/deltoids plant alkaloids, small inhibitory ribonucleic acids (siRNAs), topoisomerase inhibitors, ubiquitin ligase inhibitors, and the like, and in combination with one or more of these agents.
- BiTE antibodies are bi-specific antibodies that direct T-cells to attack cancer cells by simultaneously binding the two cells. The T-cell then attacks the target cancer cell. Examples of BiTE antibodies include adecatumumab (Micromet MT201), blinatumomab (Micromet MT103) and the like. Without being limited by theory, one of the mechanisms by which T-cells elicit apoptosis of the target cancer cell is by exocytosis of cytolytic granule components, which include perforin and granzyme B.
- SiRNAs are molecules having endogenous RNA bases or chemically modified nucleotides. The modifications do not abolish cellular activity, but rather impart increased stability and/or increased cellular potency. Examples of chemical modifications include phosphorothioate groups, 2′-deoxynucleotide, 2′-OCH3-containing ribonucleotides, 2′-F-ribonucleotides, 2′-methoxyethyl ribonucleotides, combinations thereof and the like. The siRNA can have varying lengths (e.g., 10-200 bps) and structures (e.g., hairpins, single/double strands, bulges, nicks/gaps, mismatches) and are processed in cells to provide active gene silencing. A double-stranded siRNA (dsRNA) can have the same number of nucleotides on each strand (blunt ends) or asymmetric ends (overhangs). The overhang of 1-2 nucleotides can be present on the sense and/or the antisense strand, as well as present on the 5′- and/or the 3′-ends of a given strand.
- Multivalent binding proteins are binding proteins comprising two or more antigen binding sites. Multivalent binding proteins are engineered to have the three or more antigen binding sites and are generally not naturally occurring antibodies. The term “multispecific binding protein” means a binding protein capable of binding two or more related or unrelated targets. Dual variable domain (DVD) binding proteins are tetravalent or multivalent binding proteins binding proteins comprising two or more antigen binding sites. Such DVDs may be monospecific (i.e., capable of binding one antigen) or multispecific (i.e., capable of binding two or more antigens). DVD binding proteins comprising two heavy chain DVD polypeptides and two light chain DVD polypeptides are referred to as DVD Ig's. Each half of a DVD Ig comprises a heavy chain DVD polypeptide, a light chain DVD polypeptide, and two antigen binding sites. Each binding site comprises a heavy chain variable domain and a light chain variable domain with a total of 6 CDRs involved in antigen binding per antigen binding site.
- Alkylating agents include altretamine, AMD-473, AP-5280, apaziquone, bendamustine, brostallicin, busulfan, carboquone, carmustine (BCNU), chlorambucil, CLORETAZINE® (laromustine, VNP 40101M), cyclophosphamide, decarbazine, estramustine, fotemustine, glufosfamide, ifosfamide, KW-2170, lomustine (CCNU), mafosfamide, melphalan, mitobronitol, mitolactol, nimustine, nitrogen mustard N-oxide, ranimustine, temozolomide, thiotepa, TREANDA® (bendamustine), treosulfan, trofosfamide and the like.
- Angiogenesis inhibitors include endothelial-specific receptor tyrosine kinase (Tie-2) inhibitors, epidermal growth factor receptor (EGFR) inhibitors, insulin growth factor-2 receptor (IGFR-2) inhibitors, matrix metalloproteinase-2 (MMP-2) inhibitors, matrix metalloproteinase-9 (MMP-9) inhibitors, platelet-derived growth factor receptor (PDGFR) inhibitors, thrombospondin analogs, vascular endothelial growth factor receptor tyrosine kinase (VEGFR) inhibitors and the like.
- Antimetabolites include ALIMTA® (pemetrexed disodium, LY231514, MTA), 5-azacitidine, XELODA® (capecitabine), carmofur, LEUSTAT® (cladribine), clofarabine, cytarabine, cytarabine ocfosfate, cytosine arabinoside, decitabine, deferoxamine, doxifluridine, eflornithine, EICAR (5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide), enocitabine, ethnylcytidine, fludarabine, 5-fluorouracil alone or in combination with leucovorin, GEMZAR® (gemcitabine), hydroxyurea, ALKERAN®(melphalan), mercaptopurine, 6-mercaptopurine riboside, methotrexate, mycophenolic acid, nelarabine, nolatrexed, ocfosfate, pelitrexol, pentostatin, raltitrexed, Ribavirin, triapine, trimetrexate, S-1, tiazofurin, tegafur, TS-1, vidarabine, UFT and the like.
- Antivirals include ritonavir, hydroxychloroquine and the like.
- Aurora kinase inhibitors include ABT-348, AZD-1152, MLN-8054, VX-680, Aurora A-specific kinase inhibitors, Aurora B-specific kinase inhibitors and pan-Aurora kinase inhibitors and the like.
- Bcl-2 protein inhibitors include AT-101 ((−)gossypol), GENASENSE® (G3139 or oblimersen (Bcl-2-targeting antisense oligonucleotide)), IPI-194, IPI-565, N-(4-(4-((4′-chloro(1,1′-biphenyl)-2-yl)methyl)piperazin-1-yl)benzoyl)-4-(((1R)-3-(dimethylamino)-1-((phenylsulfanyl)methyl)propyl)amino)-3-nitrobenzenesulfonamide) (ABT-737), N-(4-(4-((2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohex-1-en-1-yl)methyl)piperazin-1-yl)benzoyl)-4-(((1R)-3-(morpholin-4-yl)-1-((phenylsulfanyl)methyl)propyl)amino)-3-((trifluoromethyl)sulfonyl)benzenesulfonamide (ABT-263), GX-070 (obatoclax) and the like.
- Bcr-Abl kinase inhibitors include DASATINIB® (BMS-354825), GLEEVEC® (imatinib) and the like.
- CDK inhibitors include AZD-5438, BMI-1040, BMS-032, BMS-387, CVT-2584, flavopyridol, GPC-286199, MCS-5A, PD0332991, PHA-690509, seliciclib (CYC-202, R-roscovitine), ZK-304709 and the like.
- COX-2 inhibitors include ABT-963, ARCOXIA® (etoricoxib), BEXTRA® (valdecoxib), BMS347070, CELEBREX® (celecoxib), COX-189 (lumiracoxib), CT-3, DERAMAXX® (deracoxib), JTE-522, 4-methyl-2-(3,4-dimethylphenyl)-1-(4-sulfamoylphenyl-1H-pyrrole), MK-663 (etoricoxib), NS-398, parecoxib, RS-57067, SC-58125, SD-8381, SVT-2016, S-2474, T-614, VIOXX® (rofecoxib) and the like.
- EGFR inhibitors include ABX-EGF, anti-EGFR immunoliposomes, EGF-vaccine, EMD-7200, ERBITUX® (cetuximab), HR3, IgA antibodies, IRESSA® (gefitinib), TARCEVA® (erlotinib or OSI-774), TP-38, EGFR fusion protein, TYKERB® (lapatinib) and the like.
- ErbB2 receptor inhibitors include CP-724-714, CI-1033 (canertinib), HERCEPTIN® (trastuzumab), TYKERB® (lapatinib), OMNITARG® (2C4, petuzumab), TAK-165, GW-572016 (ionafarnib), GW-282974, EKB-569, PI-166, dHER2 (HER2 vaccine), APC-8024 (HER-2 vaccine), anti-HER/2neu bispecific antibody, B7.her2IgG3, AS HER2 trifunctional bispecfic antibodies, mAB AR-209, mAB 2B-1 and the like.
- Histone deacetylase inhibitors include depsipeptide, LAQ-824, MS-275, trapoxin, suberoylanilide hydroxamic acid (SAHA), TSA, valproic acid and the like.
- HSP-90 inhibitors include 17-AAG-nab, 17-AAG, CNF-101, CNF-1010, CNF-2024, 17-DMAG, geldanamycin, IPI-504, KOS-953, MYCOGRAB® (human recombinant antibody to HSP-90), NCS-683664, PU24FC1, PU-3, radicicol, SNX-2112, STA-9090 VER49009 and the like.
- Inhibitors of inhibitors of apoptosis proteins include HGS1029, GDC-0145, GDC-0152, LCL-161, LBW-242 and the like.
- Antibody drug conjugates include anti-CD22-MC-MMAF, anti-CD22-MC-MMAE, anti-CD22-MCC-DM1, CR-011-vcMMAE, PSMA-ADC, MEDI-547, SGN-19Am SGN-35, SGN-75 and the like
- Activators of death receptor pathway include TRAIL, antibodies or other agents that target TRAIL or death receptors (e.g., DR4 and DR5) such as Apomab, conatumumab, ETR2-ST01, GDC0145 (lexatumumab), HGS-1029, LBY-135, PRO-1762 and trastuzumab.
- Kinesin inhibitors include Eg5 inhibitors such as AZD4877, ARRY-520; CENPE inhibitors such as GSK923295A and the like.
- JAK-2 inhibitors include CEP-701 (lesaurtinib), XL019 and INCB018424 and the like.
- MEK inhibitors include ARRY-142886, ARRY-438162 PD-325901, PD-98059 and the like.
- mTOR inhibitors include AP-23573, CCI-779, everolimus, RAD-001, rapamycin, temsirolimus, ATP-competitive TORC1/TORC2 inhibitors, including PI-103, PP242, PP30, Torin 1 and the like.
- Non-steroidal anti-inflammatory drugs include AMIGESIC® (salsalate), DOLOBID® (diflunisal), MOTRIN® (ibuprofen), ORUDIS® (ketoprofen), RELAFEN® (nabumetone), FELDENE® (piroxicam), ibuprofen cream, ALEVE® (naproxen) and NAPROSYN® (naproxen), VOLTAREN® (diclofenac), INDOCIN® (indomethacin), CLINORIL® (sulindac), TOLECTIN® (tolmetin), LODINE® (etodolac), TORADOL® (ketorolac), DAYPRO® (oxaprozin) and the like.
- PDGFR inhibitors include C-451, CP-673, CP-868596 and the like.
- Platinum chemotherapeutics include cisplatin, ELOXATIN® (oxaliplatin) eptaplatin, lobaplatin, nedaplatin, PARAPLATIN® (carboplatin), satraplatin, picoplatin and the like.
- Polo-like kinase inhibitors include BI-2536 and the like.
- Phosphoinositide-3 kinase (PI3K) inhibitors include wortmannin, LY294002, XL-147, CAL-120, ONC-21, AEZS-127, ETP-45658, PX-866, GDC-0941, BGT226, BEZ235, XL765 and the like.
- Thrombospondin analogs include ABT-510, ABT-567, ABT-898, TSP-1 and the like.
- VEGFR inhibitors include AVASTIN® (bevacizumab), ABT-869, AEE-788, ANGIOZYME™ (a ribozyme that inhibits angiogenesis (Ribozyme Pharmaceuticals (Boulder, Colo.) and Chiron, (Emeryville, Calif.)), axitinib (AG-13736), AZD-2171, CP-547,632, IM-862, MACUGEN (pegaptamib), NEXAVAR® (sorafenib, BAY43-9006), pazopanib (GW-786034), vatalanib (PTK-787, ZK-222584), SUTENT® (sunitinib, SU-11248), VEGF trap, ZACTIMA™ (vandetanib, ZD-6474) and the like.
- Antibiotics include intercalating antibiotics aclarubicin, actinomycin D, amrubicin, annamycin, adriamycin, BLENOXANE® (bleomycin), daunorubicin, CAELYX® or MYOCET® (liposomal doxorubicin), elsamitrucin, epirbucin, glarbuicin, ZAVEDOS® (idarubicin), mitomycin C, nemorubicin, neocarzinostatin, peplomycin, pirarubicin, rebeccamycin, stimalamer, streptozocin, VALSTAR® (valrubicin), zinostatin and the like.
- Topoisomerase inhibitors include aclarubicin, 9-aminocamptothecin, amonafide, amsacrine, becatecarin, belotecan, BN-80915, CAMPTOSAR® (irinotecan hydrochloride), camptothecin, CARDIOXANE® (dexrazoxine), diflomotecan, edotecarin, ELLENCE® or PHARMORUBICIN® (epirubicin), etoposide, exatecan, 10-hydroxycamptothecin, gimatecan, lurtotecan, mitoxantrone, orathecin, pirarbucin, pixantrone, rubitecan, sobuzoxane, SN-38, tafluposide, topotecan and the like.
- Antibodies include AVASTIN® (bevacizumab), CD40-specific antibodies, chTNT-1/B, denosumab, ERBITUX® (cetuximab), HUMAX-CD4® (zanolimumab), IGF1R-specific antibodies, lintuzumab, PANOREX® (edrecolomab), RENCAREX® (WX G250), RITUXAN® (rituximab), ticilimumab, trastuzimab, CD20 antibodies types I and II and the like.
- Hormonal therapies include ARIMIDEX® (anastrozole), AROMASIN® (exemestane), arzoxifene, CASODEX® (bicalutamide), CETROTIDE® (cetrorelix), degarelix, deslorelin, DESOPAN® (trilostane), dexamethasone, DROGENIL® (flutamide), EVISTA® (raloxifene), AFEMA™ (fadrozole), FARESTON® (toremifene), FASLODEX® (fulvestrant), FEMARA® (letrozole), formestane, glucocorticoids, HECTOROL® (doxercalciferol), RENAGEL® (sevelamer carbonate), lasofoxifene, leuprolide acetate, MEGACE® (megesterol), MIFEPREX® (mifepristone), NILANDRON™ (nilutamide), NOLVADEX® (tamoxifen citrate), PLENAXIS™ (abarelix), prednisone, PROPECIA® (finasteride), rilostane, SUPREFACT® (buserelin), TRELSTAR® (luteinizing hormone releasing hormone (LHRH)), VANTAS® (Histrelin implant), VETORYL® (trilostane or modrastane), ZOLADEX® (fosrelin, goserelin) and the like.
- Deltoids and retinoids include seocalcitol (EB1089, CB1093), lexacalcitrol (KH1060), fenretinide, PANRETIN® (aliretinoin), ATRAGEN® (liposomal tretinoin), TARGRETIN® (bexarotene), LGD-1550 and the like.
- PARP inhibitors include ABT-888 (veliparib), olaparib, KU-59436, AZD-2281, AG-014699, BSI-201, BGP-15, INO-1001, ONO-2231 and the like.
- Plant alkaloids include, but are not limited to, vincristine, vinblastine, vindesine, vinorelbine and the like.
- Proteasome inhibitors include VELCADE® (bortezomib), MG132, NPI-0052, PR-171 and the like.
- Examples of immunologicals include interferons and other immune-enhancing agents. Interferons include interferon alpha, interferon alpha-2a, interferon alpha-2b, interferon beta, interferon gamma-1a, ACTIMMUNE® (interferon gamma-1b) or interferon gamma-n1, combinations thereof and the like. Other agents include ALFAFERONE®, (IFN-α), BAM-002 (oxidized glutathione), BEROMUN® (tasonermin), BEXXAR® (tositumomab), CAMPATH® (alemtuzumab), CTLA4 (cytotoxic lymphocyte antigen 4), decarbazine, denileukin, epratuzumab, GRANOCYTE® (lenograstim), lentinan, leukocyte alpha interferon, imiquimod, MDX-010 (anti-CTLA-4), melanoma vaccine, mitumomab, molgramostim, MYLOTARG™ (gemtuzumab ozogamicin), NEUPOGEN® (filgrastim), OncoVAC-CL, OVAREX® (oregovomab), pemtumomab (Y-muHMFG1), PROVENGE® (sipuleucel-T), sargaramostim, sizofilan, teceleukin, THERACYS® (Bacillus Calmette-Guerin), ubenimex, VIRULIZIN® (immunotherapeutic, Lorus Pharmaceuticals), Z-100 (Specific Substance of Maruyama (SSM)), WF-10 (Tetrachlorodecaoxide (TCDO)), PROLEUKIN® (aldesleukin), ZADAXIN® (thymalfasin), ZENAPAX® (daclizumab), ZEVALIN® (90Y-Ibritumomab tiuxetan) and the like.
- Biological response modifiers are agents that modify defense mechanisms of living organisms or biological responses, such as survival, growth or differentiation of tissue cells to direct them to have anti-tumor activity and include krestin, lentinan, sizofiran, picibanil PF-3512676 (CpG-8954), ubenimex and the like.
- Pyrimidine analogs include cytarabine (ara C or Arabinoside C), cytosine arabinoside, doxifluridine, FLUDARA® (fludarabine), 5-FU (5-fluorouracil), floxuridine, GEMZAR® (gemcitabine), TOMUDEX® (ratitrexed), TROXATYL™ (triacetyluridine troxacitabine) and the like.
- Purine analogs include LANVIS® (thioguanine) and PURI-NETHOL® (mercaptopurine).
- Antimitotic agents include batabulin, epothilone D (KOS-862), N-(2-((4-hydroxyphenyl)amino)pyridin-3-yl)-4-methoxybenzenesulfonamide, ixabepilone (BMS 247550), paclitaxel, TAXOTERE® (docetaxel), PNU100940 (109881), patupilone, XRP-9881 (larotaxel), vinflunine, ZK-EPO (synthetic epothilone) and the like.
- Ubiquitin ligase inhibitors include MDM2 inhibitors, such as nutlins, NEDD8 inhibitors such as MLN4924 and the like.
- Compounds of this invention can also be used as radiosensitizers that enhance the efficacy of radiotherapy. Examples of radiotherapy include external beam radiotherapy, teletherapy, brachytherapy and sealed, unsealed source radiotherapy and the like.
- Additionally, compounds having Formula (I) may be combined with other chemotherapeutic agents such as ABRAXANE™ (ABI-007), ABT-100 (farnesyl transferase inhibitor), ADVEXIN® (Ad5CMV-p53 vaccine), ALTOCOR® or MEVACOR® (lovastatin), AMPLIGEN® (poly I:poly C12U, a synthetic RNA), APTOSYN® (exisulind), AREDIA® (pamidronic acid), arglabin, L-asparaginase, atamestane (1-methyl-3,17-dione-androsta-1,4-diene), AVAGE® (tazarotene), AVE-8062 (combreastatin derivative) BEC2 (mitumomab), cachectin or cachexin (tumor necrosis factor), canvaxin (vaccine), CEAVAC® (cancer vaccine), CELEUK® (celmoleukin), CEPLENE® (histamine dihydrochloride), CERVARIX® (human papillomavirus vaccine), CHOP® (C: CYTOXAN® (cyclophosphamide); H: ADRIAMYCIN® (hydroxydoxorubicin); O: Vincristine (ONCOVIN®); P: prednisone), CYPAT™ (cyproterone acetate), combrestatin A4P, DAB(389)EGF (catalytic and translocation domains of diphtheria toxin fused via a His-Ala linker to human epidermal growth factor) or TransMID-107R™ (diphtheria toxins), dacarbazine, dactinomycin, 5,6-dimethylxanthenone-4-acetic acid (DMXAA), eniluracil, EVIZON™ (squalamine lactate), DIMERICINE® (T4N5 liposome lotion), discodermolide, DX-8951 f (exatecan mesylate), enzastaurin, EP0906 (epithilone B), GARDASIL® (quadrivalent human papillomavirus (Types 6, 11, 16, 18) recombinant vaccine), GASTRIMMUNE®, GENASENSE®, GMK (ganglioside conjugate vaccine), GVAX® (prostate cancer vaccine), halofuginone, histerelin, hydroxycarbamide, ibandronic acid, IGN-101, IL-13-PE38, IL-13-PE38QQR (cintredekin besudotox), IL-13-pseudomonas exotoxin, interferon-α, interferon-γ, JUNOVAN™ or MEPACT™ (mifamurtide), lonafarnib, 5,10-methylenetetrahydrofolate, miltefosine (hexadecylphosphocholine), NEOVASTAT®(AE-941), NEUTREXIN® (trimetrexate glucuronate), NIPENT® (pentostatin), ONCONASE® (a ribonuclease enzyme), ONCOPHAGE® (melanoma vaccine treatment), ONCOVAX® (IL-2 Vaccine), ORATHECIN™ (rubitecan), OSIDEM® (antibody-based cell drug), OVAREX® MAb (murine monoclonal antibody), paclitaxel, PANDIMEX™ (aglycone saponins from ginseng comprising 20(S)protopanaxadiol (aPPD) and 20(S)protopanaxatriol (aPPT)), panitumumab, PANVAC®-VF (investigational cancer vaccine), pegaspargase, PEG Interferon A, phenoxodiol, procarbazine, rebimastat, REMOVAB® (catumaxomab), REVLIMID® (lenalidomide), RSR13 (efaproxiral), SOMATULINE® LA (lanreotide), SORIATANE® (acitretin), staurosporine (Streptomyces staurospores), talabostat (PT100), TARGRETIN® (bexarotene), TAXOPREXIN® (DHA-paclitaxel), TELCYTA® (canfosfamide, TLK286), temilifene, TEMODAR® (temozolomide), tesmilifene, thalidomide, THERATOPE® (STn-KLH), thymitaq (2-amino-3,4-dihydro-6-methyl-4-oxo-5-(4-pyridylthio)quinazoline dihydrochloride), TNFERADE™ (adenovector: DNA carrier containing the gene for tumor necrosis factor-a), TRACLEER® or ZAVESCA® (bosentan), tretinoin (Retin-A), tetrandrine, TRISENOX® (arsenic trioxide), VIRULIZIN®, ukrain (derivative of alkaloids from the greater celandine plant), vitaxin (anti-alphavbeta3 antibody), XCYTRIN® (motexafin gadolinium), XINLAY™ (atrasentan), XYOTAX™ (paclitaxel poliglumex), YONDELIS® (trabectedin), ZD-6126, ZINECARD® (dexrazoxane), ZOMETA® (zolendronic acid), zorubicin and the like.
- Determination of the utility of compounds having Formula (I) as binders to and inhibitors of NAMPT was performed using Time-Resolved Fluorescence Resonance Energy Transfer (TR-FRET) binding assays.
- Test compounds were serially diluted (typically 11 half log dilutions) in neat DMSO to 50× final concentrations prior to dilution with assay buffer (50 mM HEPES (NaOH), pH 7.5, 100 mM NaCl, 10 mM MgCl2, 1 mM DTT, 1% Glycerol) to 3× and 6% DMSO. Six μL were transferred to 384-well low-volume plates (Owens Corning #3673). To this, 12 L of a 1.5× solution containing enzyme, probe and antibody were added. Final concentrations in the 18 μL reactions were 1× assay buffer, 2% DMSO, 6.8 nM NAMPT (human, recombinant, C-terminally His-tagged), 200 nM probe (a potent nicotinamide-competitive inhibitor conjugated to Oregon Green 488) and 1 nM Tb-anti-His antibody (Invitrogen #PV5895).
- Reactions were equilibrated at room temperature for 3 hours prior to reading on an Envision multi-label plate reader (Perkin Elmer; Ex=337 nm, Em=520 and 495 nm). Time-resolved FRET ratios (Em520/Em495) were normalized to controls, plotted as a function of compound concentration and fit with the four-parameter logistic equation to determine IC50s.
- Compound handling and data processing were identical to the assay in the absence of substrates (above). Final concentrations were 1× assay buffer, 2% DMSO, 2 nM NAMPT, 2 nM probe, 1 nM Tb-anti-His antibody (Invitrogen #PV5895), 200 M PRPP and 2.5 mM ATP. Reactions were equilibrated for 16 hours prior to measurement to allow for potential enzymatic modification of test compounds.
- Table 1 shows the utility of compounds having Formula I to functionally inhibit NAMPT.
-
TABLE 1 TR- FRET TR- Binding - FRET IC50 Binding - (with IC50 PRPP) Example (μM) (μM) 1 0.0921 0.00072 2 0.854 0.0398 3 0.0316 0.000282 4 0.413 0.000516 5 2.5 0.000684 6 2.91 0.000964 7 0.183 0.000516 8 0.114 0.000702 9 1.72 0.000459 10 0.197 0.000457 11 7.6 0.000271 12 0.486 0.000292 13 0.653 0.000663 14 0.741 0.00122 15 1.76 0.000841 16 0.409 0.000396 17 2.96 0.000401 18 2.73 0.000418 19 2.68 0.000921 20 0.404 0.000169 21 0.433 0.000887 22 0.399 0.000277 23 0.281 0.000409 24 0.167 0.000363 25 0.508 0.000714 26 0.211 0.0011 27 0.756 0.000658 28 0.152 0.00019 29 0.168 0.000236 30 1.18 0.000785 31 0.739 0.000311 32 0.906 0.000169 33 0.369 0.000553 34 0.208 0.000377 35 0.387 0.000801 36 0.356 0.000444 37 0.129 0.000309 38 0.243 0.000266 39 0.814 0.00026 40 0.0409 0.000217 41 0.294 0.00115 42 0.697 0.000381 43 4.35 0.000169 44 0.396 0.000496 45 0.879 0.00119 46 0.773 0.000318 47 0.0575 0.00062 48 >10 0.000169 49 0.442 0.000317 50 1.64 0.000817 51 0.264 0.000524 52 0.0186 0.00579 53 4.45 0.0144 54 0.363 0.00255 55 0.364 0.00137 56 0.158 0.00107 57 0.0058 58 0.523 0.00143 59 0.222 0.000695 60 0.00861 0.00149 61 0.0782 0.000549 62 0.25 0.000456 63 0.636 0.000283 64 0.518 0.000495 65 0.773 0.000685 66 0.558 0.000326 67 0.53 0.000326 68 0.386 0.000476 69 0.676 0.000268 70 0.71 0.000616 71 0.754 0.000348 72 0.851 0.000536 73 0.605 0.000426 74 0.356 0.000222 75 0.0122 0.000445 76 0.993 0.000739 77 0.0561 0.00288 78 0.0565 0.0024 79 0.121 0.00697 80 0.228 0.00571 81 0.0155 0.00268 82 0.357 0.00642 83 0.899 0.0023 84 1.67 0.0109 85 4.07 0.00141 86 2.04 0.0119 87 2.05 0.00135 88 2.85 0.00855 89 0.667 0.000383 90 0.204 0.00063 91 0.174 0.00126 92 0.183 0.000881 93 0.389 0.00139 94 0.29 0.000593 95 0.201 0.000991 96 0.192 0.00156 97 0.109 0.000333 98 0.12 0.000367 99 0.119 0.000411 100 0.102 0.000169 101 0.332 0.00173 102 0.385 0.00121 103 0.84 0.00144 104 0.135 0.002 105 0.106 0.000476 106 0.247 0.000201 107 0.0451 0.000492 108 1.77 0.00105 109 0.34 0.000209 110 0.423 0.000174 111 0.263 0.000209 112 0.0465 0.000169 113 0.356 0.000169 114 0.818 0.00111 115 0.243 0.000676 116 0.863 0.00069 117 0.392 0.000436 118 0.0352 0.000234 119 0.942 0.000783 120 0.0739 0.000367 121 0.486 0.000234 122 0.255 0.00476 123 0.133 0.00257 124 1.1 0.00212 125 0.547 0.00209 126 0.102 0.000963 127 0.0522 0.000522 128 0.0307 0.000873 129 0.0116 0.000634 130 0.0532 0.000981 131 0.0152 0.00167 132 0.155 0.0133 133 0.067 0.000709 134 0.303 0.00149 135 0.0738 0.00127 136 0.0727 0.000512 137 0.315 0.00721 138 0.0807 0.000424 139 0.582 0.000173 140 1.34 0.000927 141 2.11 0.000757 142 1.43 0.00305 143 8.71 0.00203 144 9.49 0.00292 145 0.191 0.00108 146 0.261 0.000403 147 0.251 0.00063 148 6.23 0.00135 149 >10 0.00486 150 6.11 0.00349 151 7.15 0.00554 152 3.6 0.00691 153 0.118 0.00188 154 0.194 0.0026 155 3.37 0.0023 156 3.27 0.00318 157 4.14 0.0011 158 0.341 0.00639 159 2.49 0.00216 160 3.22 0.00126 161 1.31 0.00289 162 2.57 0.00209 163 2.1 0.00629 164 2.46 0.00346 165 1.53 0.00161 166 1.43 0.00181 167 1.73 0.00252 168 1.11 0.000951 169 0.375 0.00425 170 3.36 0.00225 171 2.17 0.00251 172 2.21 0.00355 173 1.51 0.00124 174 0.0283 0.000169 175 0.697 0.0009 176 0.0606 0.000414 177 0.0201 0.000169 178 0.0143 0.000169 179 0.0581 0.000445 180 0.584 0.000266 181 0.349 0.000283 182 0.139 0.0004 183 1.05 0.0018 184 4.34 0.00254 185 >10 0.00186 186 0.0657 0.000347 187 0.549 0.000172 188 >10 0.00509 189 0.192 0.0111 190 0.4 0.00457 191 0.821 0.00609 192 0.238 0.000242 193 0.516 0.000266 194 0.0323 0.00024 195 0.0247 0.000251 196 0.358 0.000169 197 1.57 0.000505 198 0.0325 0.000225 199 0.00976 0.000311 200 0.063 0.000482 201 0.0466 0.000281 202 0.216 0.000355 203 0.0137 0.00021 204 4.83 0.000773 205 1.06 0.000358 206 0.0257 0.000263 207 1.51 0.000282 208 0.404 0.000169 209 0.811 0.000988 210 0.469 0.000363 211 1.66 0.000453 212 0.0448 0.00021 213 0.116 0.000271 214 0.641 0.00128 215 2.01 0.00304 216 0.118 0.00019 217 0.22 0.0002 218 0.123 0.000169 219 0.0794 0.000903 220 0.0742 0.000278 221 0.12 0.000352 222 0.112 0.000192 223 0.109 0.000354 224 0.233 0.000555 225 0.155 0.000673 226 0.113 0.000608 227 0.0162 0.000273 228 0.0494 0.000238 229 0.0136 0.000398 230 0.294 0.000169 231 0.817 0.000546 232 0.396 0.000277 233 0.495 0.000401 234 0.904 0.000736 235 0.494 0.000369 236 0.604 0.000243 237 0.451 0.000285 238 0.123 0.000187 239 0.308 0.000771 240 7.35 0.00875 241 0.0674 0.000169 242 0.0571 0.000169 243 0.169 0.000169 244 >10 0.00169 245 2.89 0.000502 246 0.0732 0.00022 247 0.0627 0.000275 248 0.0658 0.000169 249 0.817 0.00072 250 0.0205 0.00023 251 2.2 0.00063 252 0.0374 0.000274 253 0.0144 0.000229 254 0.0313 0.000306 255 8.19 0.00222 256 0.126 0.000266 257 0.101 0.000344 258 0.113 0.000558 259 0.0266 0.000169 260 0.0465 0.000351 261 0.0627 0.000231 262 0.00367 0.000221 263 0.0486 0.000247 264 0.0404 0.000412 265 0.0331 0.000266 266 0.12 0.000333 267 0.0543 0.000291 268 0.755 0.000169 269 0.0412 0.000169 270 0.0609 0.000991 271 0.0517 0.000169 272 0.0272 0.000417 273 0.0493 0.000555 274 0.0178 0.000196 275 0.0123 0.00043 276 0.107 0.000468 277 0.103 0.000667 278 0.102 0.000621 279 0.0688 0.000437 280 0.0113 0.000213 281 0.0055 0.000214 282 0.0765 0.000297 283 0.0632 0.000264 284 0.00796 0.000169 285 0.0826 0.000593 286 0.12 0.000412 287 0.0673 0.000351 288 0.0495 0.000568 289 0.155 0.000286 290 0.415 0.00096 291 0.159 0.000449 292 1.54 0.00115 293 0.0273 0.000169 294 0.0447 0.000169 295 0.0561 0.000292 296 0.067 0.000226 297 0.177 0.000286 298 3.41 0.000557 299 0.172 0.000283 300 0.0614 0.000169 301 0.288 0.000301 302 0.16 0.000435 303 0.00999 0.000169 304 0.0662 0.000169 305 0.494 0.000449 306 0.144 0.000169 307 0.0508 0.000169 308 0.306 0.000169 309 0.117 0.000169 310 0.564 0.000217 311 0.289 0.000274 312 0.165 0.000243 313 0.531 0.00036 314 1.98 0.000581 315 0.231 0.00032 316 0.0421 0.000169 317 0.317 0.000282 318 0.0416 0.000228 319 0.466 0.000192 320 0.0963 0.000208 321 3.16 0.000792 322 6.04 0.0341 323 1.4 0.000232 324 0.981 0.000752 325 0.18 0.000278 326 2.35 0.0013 327 1.32 0.000558 328 0.068 0.000169 329 0.0308 0.000169 330 0.32 0.000432 331 0.383 0.000416 332 0.18 0.000297 333 0.583 0.000346 334 0.0809 0.000345 335 0.632 0.000354 336 0.334 0.000264 337 0.497 0.000205 338 0.609 0.000394 339 >10 0.000797 340 >10 0.000817 341 >10 0.000719 342 >10 0.000454 343 >10 0.000456 344 0.036 0.000169 345 0.201 0.00027 346 3.11 0.000548 347 4.73 0.000667 348 >10 0.00152 349 4.11 0.000736 350 >10 0.000795 351 8.39 0.000792 352 >10 0.00106 353 3.17 0.00047 354 >10 0.000526 355 0.831 0.000169 356 >10 0.000169 357 >10 0.000291 358 1.84 0.00219 359 >10 0.0025 360 0.291 0.000717 361 5.03 0.00194 362 0.143 0.000256 363 0.588 0.000305 364 0.135 0.000172 365 1.34 0.000171 366 0.146 0.000435 367 0.65 0.00018 368 0.602 0.000317 369 0.429 0.000337 370 0.0476 0.000175 371 1.44 0.000298 372 2.44 0.00046 373 3.04 0.00036 374 1.67 0.000292 375 0.986 0.000241 376 1.05 0.000305 377 1.67 0.000275 378 0.897 0.000169 379 0.279 0.00029 380 0.179 0.000251 381 0.0841 0.000259 382 0.119 0.000204 383 0.0495 0.000225 384 0.406 0.000375 385 0.491 0.000539 386 0.283 0.000254 387 0.419 0.000467 388 0.388 0.000506 389 0.584 0.000617 390 0.133 0.000445 391 0.171 0.000227 392 0.814 0.000465 393 >10 0.00437 394 >10 0.00308 395 0.0125 0.000193 396 0.0226 0.00036 397 0.0177 0.000169 398 0.21 0.000792 399 9.5 0.00154 400 0.0812 0.000298 401 0.0126 0.000292 402 0.0548 0.000327 403 1.55 0.000847 404 2.55 0.00088 405 0.0784 0.000214 406 1.14 0.000505 407 0.22 0.000659 408 0.276 0.000725 409 >10 0.48 410 0.0207 0.000169 411 1.87 0.000556 412 1.25 0.000424 413 0.805 0.000279 414 2.63 0.000307 415 1.62 0.000246 416 2.5 0.000318 417 6.84 0.000264 418 4.75 0.000233 419 2.43 0.000197 420 2.71 0.000226 421 2.45 0.000271 422 1.72 0.000212 423 8.26 0.000338 424 0.988 0.000494 425 0.153 0.000227 426 0.0256 0.000169 427 0.15 0.00027 428 0.0871 0.000258 429 0.129 0.000396 430 0.292 0.000264 431 0.301 0.000276 432 0.304 0.00033 433 0.2 0.000248 434 0.102 0.000169 435 0.163 0.000191 436 1.59 0.000416 437 0.0291 0.000169 438 0.145 0.000427 439 0.453 0.000641 440 0.295 0.00049 441 0.338 0.000324 442 0.301 0.0002 443 0.138 0.000274 444 0.156 0.000244 445 0.11 0.000212 446 0.388 0.000253 447 0.261 0.000232 448 0.175 0.000176 449 0.256 0.000169 450 0.422 0.000244 451 0.4 0.000373 452 0.293 0.000285 453 0.152 0.000258 454 0.405 0.00034 455 0.0167 0.000194 456 0.389 0.000169 457 1.14 0.000487 458 0.94 0.000382 459 0.381 0.00041 460 0.569 0.000307 461 0.459 0.000169 462 0.0591 0.000266 463 0.314 0.000529 464 0.0634 0.000169 465 0.0138 0.000169 466 0.0749 0.000287 467 0.0911 0.000278 468 >10 0.000985 469 >10 0.000432 470 5.58 0.000456 471 3.44 0.000471 472 2.86 0.000334 473 >10 0.00101 474 1.98 0.000362 475 0.00976 0.000169 476 0.0708 0.000194 477 0.0729 0.000235 478 0.192 0.00024 479 0.063 0.000243 480 0.181 0.000342 481 0.0572 0.000176 482 0.0763 0.000259 483 0.13 0.000575 484 0.0795 0.00019 485 0.0956 0.000205 486 0.0917 0.000232 487 0.143 0.000334 488 0.138 0.000544 489 1.22 0.000263 490 0.753 0.000267 491 >10 0.0019 492 >10 0.000863 493 1.29 0.000455 494 7.56 0.000712 495 1.47 0.000399 496 0.199 0.00114 497 0.0242 0.00286 498 0.309 0.000169 499 0.113 0.00038 500 0.181 0.000169 501 0.104 0.000483 502 0.169 0.000385 503 0.0532 0.000277 504 0.185 0.000361 505 0.253 0.000355 506 0.245 0.000407 507 0.121 0.000359 508 0.257 0.000481 509 0.163 0.000384 510 0.142 0.000284 511 0.0653 0.000286 512 0.631 0.000209 513 0.0239 0.000188 514 0.368 0.000249 515 0.18 0.000268 516 0.117 0.000266 517 0.33 0.000264 518 0.234 0.000169 519 0.218 0.000338 520 0.565 0.000301 521 0.413 0.000292 522 0.0581 0.000199 523 0.343 0.000422 524 0.0247 0.000169 525 0.0864 0.000213 526 0.126 0.000275 527 0.141 0.000265 528 0.126 0.000276 529 0.248 0.000283 530 0.378 0.000791 531 0.333 0.000253 532 0.338 0.000178 533 0.101 0.000169 534 0.145 0.000251 535 0.297 0.000325 536 0.0776 0.000202 537 0.461 0.00023 538 0.275 0.000514 539 0.0985 0.00031 540 0.266 0.000305 541 0.175 0.000448 542 0.0351 0.000337 543 1.48 0.000383 544 0.871 0.000437 545 0.109 0.000403 546 0.237 0.0232 547 0.498 0.000423 548 0.397 0.000471 549 0.0812 0.000224 550 0.762 0.000427 551 0.713 0.000392 552 0.184 0.000543 553 0.478 0.000592 554 0.451 0.000837 555 0.427 0.000749 556 0.00543 0.000407 557 0.167 0.000359 558 1.41 0.000352 559 0.681 0.000223 560 0.969 0.000312 561 0.869 0.000335 562 0.218 0.000607 563 0.322 0.00419 564 0.0238 0.00343 565 0.215 0.00538 566 >10 0.216 567 0.403 0.00111 568 0.375 0.000723 569 0.217 0.000669 570 0.0704 0.000751 571 0.0417 0.000494 572 0.0516 0.000403 573 0.0242 0.000403 574 0.0975 0.000505 575 3.25 0.0108 576 0.016 0.000783 577 0.0189 0.000361 578 0.682 0.000775 579 0.488 0.000634 580 1.47 0.000798 581 0.945 0.00109 582 0.711 0.000911 583 1.12 0.000799 584 0.811 0.000756 585 0.641 0.000648 586 0.842 0.00109 587 0.236 0.000917 588 0.684 0.000623 589 0.0161 0.000887 590 0.666 0.000734 591 0.138 0.000761 592 0.0388 0.000603 593 0.767 0.000544 594 0.0227 0.000682 595 0.133 0.000746 596 0.691 0.000909 597 0.232 0.000862 598 0.457 0.000804 599 0.527 0.000786 600 0.51 0.000169 601 0.712 0.000682 602 0.786 0.000887 603 1.03 0.00101 604 0.151 0.000843 605 0.559 0.000886 606 0.281 0.000169 607 0.478 0.000796 608 0.481 0.00051 609 0.598 0.00062 610 0.751 0.000762 611 0.288 0.000621 612 0.706 0.000919 613 0.347 0.000916 614 0.216 0.00067 615 0.544 0.00079 616 0.174 0.00049 617 0.164 0.000645 618 0.5 0.000751 619 0.0793 0.000616 620 0.71 0.001 621 0.114 0.00542 622 0.0294 0.00236 623 1.01 0.0016 624 0.261 0.000627 625 0.795 0.00076 626 0.645 0.000793 627 0.211 0.00071 628 0.706 0.000978 629 0.23 0.000643 630 0.266 0.000563 631 0.616 0.00126 632 0.27 0.000698 633 0.335 0.000707 634 0.353 0.000648 635 0.462 0.000975 636 0.238 0.000915 637 0.36 0.000421 638 0.0166 0.000545 639 0.215 0.000713 640 0.17 0.000817 641 0.0748 0.000684 642 0.454 0.000532 643 0.028 0.000552 644 0.0817 0.00069 645 0.091 0.000474 646 0.195 0.00051 647 0.173 0.000672 648 0.661 0.00106 649 0.203 0.000749 650 0.153 0.00111 651 0.276 0.000715 652 0.535 0.00116 653 0.831 0.000893 654 0.213 0.000945 655 0.23 0.000998 656 0.218 0.000738 657 0.232 0.000589 658 0.137 0.00076 659 0.646 0.00071 660 0.282 0.000693 661 0.462 0.000641 662 0.318 0.000671 663 0.653 0.00107 664 0.214 0.000733 665 0.123 0.000357 666 0.193 0.000855 667 0.226 0.000798 668 0.263 0.0011 669 0.407 0.000807 670 0.062 0.000545 671 0.611 0.00106 672 0.313 0.000504 673 0.452 0.000697 674 0.297 0.000535 675 0.376 0.00207 676 0.126 0.00698 677 0.00177 0.000796 678 0.0412 0.00023 679 0.0228 0.00174 680 0.0371 0.00238 681 0.0276 0.002 682 0.607 0.00158 683 0.154 0.00119 684 0.481 0.00134 685 1.25 0.00136 686 0.959 0.0013 687 0.0973 0.00116 688 1.11 0.00266 689 0.016 0.00132 690 0.0643 0.00122 691 0.169 0.00067 692 0.0839 0.00119 693 0.781 0.00142 694 0.163 0.00112 695 0.0137 0.000621 696 0.272 0.000725 697 0.735 0.000802 698 0.0364 0.000629 699 0.0411 0.000721 700 0.0684 0.00103 701 0.367 0.000856 702 0.568 0.00129 703 0.559 0.000824 704 0.503 0.000777 705 0.876 0.00163 706 0.0841 0.000937 707 0.277 0.000624 708 0.06 0.0009 709 0.0194 0.000473 710 0.0491 0.00125 711 0.0885 0.00111 712 0.0911 0.000907 713 0.0443 0.000689 714 0.168 0.000991 715 0.0659 0.000771 716 0.0502 0.000607 717 0.186 0.000428 718 0.0236 0.000755 719 0.00632 0.000835 720 0.0367 0.000181 721 0.125 0.00121 722 0.0394 0.00101 723 0.154 0.000932 724 0.161 0.000992 725 0.0196 0.000747 726 0.251 0.000534 727 0.166 0.000783 728 0.14 0.000496 729 0.428 0.000765 730 0.489 0.000847 731 0.223 0.000391 732 0.0213 0.000471 733 0.119 0.000712 734 0.0142 0.000605 735 0.646 0.000864 736 3.09 0.00073 737 0.0704 0.000612 738 0.364 0.000705 739 0.0377 0.000672 740 0.0701 0.000403 741 0.068 0.000647 742 0.241 0.000526 743 0.0633 0.000691 744 1.08 0.000806 745 0.994 0.000783 746 0.795 0.000839 747 0.435 0.00175 748 0.558 0.000648 749 0.392 0.00079 750 1.53 0.00154 751 1.24 0.001 752 5.19 0.00077 753 0.403 0.000783 754 0.00492 0.00051 755 0.013 0.00057 756 0.123 0.000609 757 0.0156 0.000705 758 0.132 0.00061 759 0.0285 0.000799 760 0.0289 0.00071 761 0.0944 0.000394 762 0.0301 0.000506 763 0.0485 0.000478 764 0.135 0.000465 765 0.0365 0.000782 766 0.0615 0.000581 767 0.265 0.00064 768 0.0281 0.000672 769 0.0984 0.000705 770 0.0388 0.000735 771 0.0708 0.000573 772 0.0615 0.000828 773 0.0726 0.000773 774 0.103 0.00046 775 0.0519 0.000538 776 0.0215 0.000169 777 0.0394 0.00092 778 0.0276 0.000414 779 0.0142 0.000603 780 0.25 0.000382 781 0.0875 0.000839 782 0.134 0.000466 783 0.0644 0.000907 784 0.0226 0.000455 785 0.0236 0.000638 786 0.0444 0.000484 787 0.055 0.000474 788 0.082 0.000674 789 0.0217 0.000434 790 0.0795 0.000586 791 0.0471 0.00115 792 0.116 0.0005 793 0.0231 0.000398 794 0.029 0.000465 795 0.0896 0.000764 796 0.0917 0.00049 797 0.0972 0.000671 798 0.0957 0.00047 799 0.102 0.000406 800 0.0821 0.000925 801 0.866 0.001 802 0.0359 0.000533 803 0.314 0.00101 804 0.289 0.000445 805 3.92 0.00112 806 2.74 0.000543 807 0.628 0.000509 808 0.0944 0.000568 809 0.0953 0.00063 810 0.481 0.0126 811 0.0998 0.00286 812 0.08 0.00257 813 0.0112 0.00153 814 0.0687 0.00163 815 0.053 0.00193 816 0.0461 0.00158 817 0.0658 0.0016 818 1.52 0.000644 819 0.0199 0.000624 820 0.499 0.00928 821 0.663 0.000284 822 0.104 0.00346 823 0.189 0.000356 824 0.118 0.000566 825 0.0261 0.000538 826 0.00779 0.000897 - PC3 cells were seeded in 96-well black plates (Corning #3904) at 500 cells/well in 90 μl of RPMI media containing 10% heat-inactivated FBS and incubated overnight at 37° C. and 5% CO2 to allow cells to attach to wells. The following day, test compounds were serially diluted in neat DMSO to 1000× final concentrations prior to dilution with RPMI media to 10× and 1% DMSO. Ten μL of the 100× compounds were then transferred to wells containing cells to produce a dose response of 10-fold dilutions from 10 M to 1×10−5 M. Cells were incubated for 5 days at 37° C. and 5% CO2, then cell viability was measured using Cell Titer Glo reagent (Promega #G7571). Percent inhibition values were calculated and fitted to a sigmoidal dose response curves using Assay Explorer software to determine IC50s. To assess whether inhibition of cell viability was due to NAMPT inhibition, the proliferation assay was also performed in the presence of 0.3 mM nicotinamide mononucleotide.
- Table 2 shows the results of the cell proliferation assay.
-
TABLE 2 Cell Titer-Glo - IC50 Example (μM) 1 0.0609 2 >10 3 0.0367 4 0.935 5 0.74 6 6.65 7 0.527 8 0.0702 9 0.649 10 0.331 11 4.53 12 0.213 13 1.17 14 0.644 15 3.97 16 0.325 17 4.96 18 0.36 19 6.63 20 0.102 21 0.899 22 0.142 23 0.0415 24 0.691 25 0.146 26 0.261 27 7.54 28 0.0142 29 0.0439 30 0.0384 31 0.107 32 0.284 33 0.0673 34 0.0383 35 0.0586 36 0.0514 37 0.0347 38 0.0659 39 7.28 40 0.0708 41 0.138 42 1.59 43 7.45 44 1.58 45 2.07 46 6.28 47 0.0648 48 5.32 49 7.04 50 6.14 51 0.083 52 0.00407 53 3.3 54 0.303 55 0.0146 56 0.00886 57 0.00576 58 0.0526 59 0.143 60 0.00958 61 0.00601 62 0.0165 63 0.0168 64 0.0198 65 0.0656 66 0.0115 67 0.0119 68 0.0538 69 0.0166 70 0.0278 71 0.0667 72 0.0659 73 0.0595 74 0.014 75 0.00149 76 0.185 77 0.0142 78 0.0407 79 0.00745 80 0.0194 81 0.0071 82 0.0679 83 0.0243 84 0.762 85 2.61 86 5.72 87 6.58 88 8.11 89 0.113 90 0.0187 91 0.0139 92 0.00948 93 0.00713 94 0.0142 95 0.0106 96 0.00965 97 0.00455 98 0.0194 99 0.0264 100 0.0162 101 0.00244 102 0.013 103 0.0621 104 0.00846 105 0.00661 106 0.0787 107 0.0108 108 7.66 109 0.0522 110 0.202 111 0.0755 112 0.00696 113 0.0933 114 0.142 115 0.00638 116 0.0613 117 0.0639 118 0.0182 119 0.146 120 0.0908 121 0.00391 122 0.172 123 0.00743 124 0.0208 125 0.023 126 0.00396 127 0.00234 128 0.00221 129 0.00274 130 0.00655 131 0.00217 132 0.523 133 0.00216 134 0.00654 135 0.00636 136 0.00305 137 0.225 138 0.00383 139 0.0122 140 0.0655 141 0.0778 142 0.0182 143 0.0808 144 0.187 145 0.00601 146 0.00769 147 0.00669 148 0.0415 149 0.0266 150 0.0362 151 0.0761 152 0.0283 153 0.00373 154 0.00667 155 0.0176 156 0.028 157 0.0292 158 0.191 159 0.233 160 0.915 161 0.635 162 0.0436 163 0.0964 164 0.101 165 0.137 166 0.0971 167 0.104 168 0.208 169 0.0269 170 0.604 171 0.0447 172 0.223 173 0.0501 174 0.00112 175 0.313 176 0.00181 177 0.00169 178 0.00185 179 0.00218 180 0.00912 181 0.00775 182 0.00137 183 0.063 184 0.0651 185 5.05 186 0.00236 187 0.0341 188 6.29 189 0.0293 190 0.0149 191 0.0143 192 0.00185 193 0.0199 194 0.000773 195 0.000966 196 0.00675 197 0.0254 198 0.00184 199 0.000539 200 0.00572 201 0.00189 202 0.00488 203 0.00239 204 1.62 205 0.483 206 0.00131 207 0.739 208 0.0849 209 0.693 210 0.398 211 0.95 212 0.0341 213 0.0397 214 0.289 215 0.686 216 0.00659 217 0.00342 218 0.0711 219 0.00559 220 0.00573 221 0.00782 222 0.00408 223 0.00708 224 0.023 225 0.00927 226 0.00726 227 0.00628 228 0.00856 229 0.00106 230 0.0072 231 0.0351 232 0.00927 233 0.00937 234 0.105 235 0.0555 236 0.0138 237 0.0372 238 0.00257 239 0.0177 240 0.651 241 0.00848 242 0.00756 243 0.028 244 7.04 245 5.5 246 0.00243 247 0.00134 248 0.00242 249 0.0665 250 0.000675 251 1.84 252 0.00191 253 0.000702 254 0.000938 255 4.29 256 0.00984 257 0.0152 258 0.0325 259 0.00254 260 0.00806 261 0.0051 262 0.00187 263 0.00243 264 0.00669 265 0.00159 266 0.606 267 0.665 268 5.54 269 0.0151 270 0.973 271 0.00271 272 0.0156 273 0.00235 274 0.0104 275 0.0239 276 0.0381 277 0.0832 278 0.0517 279 0.869 280 0.013 281 0.0248 282 0.0447 283 0.145 284 0.107 285 0.301 286 0.0194 287 0.0241 288 0.00811 289 0.00933 290 0.0722 291 0.0261 292 7.22 293 0.00774 294 0.00188 295 0.0242 296 0.0115 297 0.0358 298 2.37 299 8.64 300 0.0287 301 0.0258 302 0.0193 303 0.00179 304 0.0188 305 1.17 306 0.0219 307 0.0136 308 0.0295 309 0.0548 310 0.0244 311 0.0191 312 0.065 313 0.82 314 0.395 315 0.72 316 0.00634 317 0.542 318 0.0421 319 0.0293 320 0.171 321 1.13 322 >10 323 0.175 324 0.0547 325 0.0329 326 0.457 327 0.638 328 0.0089 329 0.0124 330 0.0229 331 0.227 332 0.0643 333 0.116 334 0.0219 335 0.0976 336 0.139 337 0.533 338 0.081 339 9.18 340 >10 341 8.3 342 6.73 343 6.53 344 0.00746 345 0.281 346 7.02 347 8.08 348 >10 349 5.51 350 8.17 351 8.11 352 9.8 353 7.51 354 7.49 355 1.94 356 1.02 357 6.74 358 2.26 359 8.77 360 0.663 361 >10 362 0.106 363 7.66 364 0.031 365 0.332 366 0.0215 367 0.601 368 0.0484 369 0.738 370 0.00993 371 0.82 372 0.868 373 0.585 374 0.792 375 >10 376 >10 377 >10 378 >10 379 0.37 380 0.04 381 0.0173 382 0.0838 383 0.0133 384 0.0517 385 0.11 386 0.0424 387 0.0581 388 0.122 389 0.0783 390 0.0803 391 0.0784 392 0.666 393 >10 394 >10 395 0.00634 396 0.0324 397 0.00712 398 0.0736 399 7.68 400 0.712 401 0.0559 402 0.00671 403 0.0545 404 9.41 405 0.0221 406 0.347 407 1.31 408 0.0192 409 10 410 nd 411 4.72 412 0.978 413 0.19 414 0.853 415 0.234 416 0.659 417 0.867 418 0.866 419 0.365 420 0.147 421 0.317 422 0.109 423 0.187 424 0.521 425 0.069 426 0.0064 427 0.0622 428 0.0675 429 0.0186 430 0.0886 431 0.0719 432 0.0363 433 0.0644 434 0.00559 435 0.0204 436 0.762 437 0.00702 438 0.0425 439 0.0375 440 441 0.0072 442 0.0707 443 0.00896 444 0.0699 445 0.0229 446 0.0612 447 0.0125 448 0.0678 449 0.0236 450 0.0701 451 0.0173 452 0.0592 453 0.00921 454 0.0422 455 0.0035 456 0.0496 457 0.194 458 0.183 459 0.0777 460 0.0509 461 0.0314 462 0.00743 463 0.234 464 0.00679 465 0.000319 466 0.00431 467 0.00402 468 2.93 469 3.38 470 0.936 471 6.51 472 0.963 473 7.85 474 0.879 475 0.00692 476 0.00942 477 0.00321 478 0.0312 479 0.00808 480 0.00743 481 0.00579 482 0.00222 483 0.0124 484 0.00959 485 0.0345 486 0.0233 487 0.0833 488 0.0983 489 >10 490 0.0899 491 7.83 492 1.27 493 0.486 494 1.22 495 0.127 496 7.14 497 0.742 498 0.0179 499 0.00219 500 0.0217 501 0.00596 502 0.0165 503 0.00421 504 0.0154 505 0.0305 506 0.0180018 507 0.0032 508 0.0285902 509 0.00747 510 0.0121 511 0.00278 512 0.0179 513 0.0011805 514 0.0308 515 0.0158 516 0.021279 517 0.0722 518 0.0348 519 0.0609 520 0.101 521 0.0935 522 0.00673 523 0.0171 524 0.00246 525 0.00677 526 0.0603 527 0.0598 528 0.024 529 0.227 530 0.0821 531 0.0529 532 0.0927 533 0.0174 534 0.00508 535 0.0285 536 0.00304 537 0.0431 538 0.00333 539 0.00347 540 0.074 541 0.0645 542 0.00289 543 0.386 544 0.647 545 0.0287 546 2.45 547 0.0255558 548 0.0744613 549 0.009417 550 0.1741494 551 0.0550545 552 0.0425577 553 0.103 554 0.177 555 0.0332 556 0.00655 557 0.0374 558 1.17 559 0.0943 560 0.844 561 0.24 562 0.0709 563 5.14 564 0.211 565 0.891 566 >10 567 0.237 568 0.18 569 0.226 570 0.00735 571 0.0229 572 0.00666 573 0.00372 574 0.005201 575 >10 576 .000569 577 0.00215 578 4.6 579 0.758 580 0.212 581 0.0812 582 0.0332 583 0.189 584 0.0587 585 0.0346 586 0.301 587 0.00754 588 0.181 589 0.00131 590 0.189 591 0.0193 592 0.00375 593 0.677 594 0.00111 595 0.00693 596 0.257 597 0.0335 598 0.0166 599 0.0523 600 0.11 601 0.0567 602 0.0486107 603 0.695 604 0.0101 605 0.0661 606 0.0348 607 0.0744 608 0.148 609 0.142 610 0.0744 611 0.0709 612 0.695 613 0.14 614 0.00572 615 0.0188 616 0.0326 617 0.0826 618 0.125 619 0.0033 620 0.131 621 0.0253 622 0.00706 623 0.446 624 0.329 625 0.226 626 0.0807 627 0.0175 628 0.0436 629 0.0652 630 0.0404 631 0.0772 632 0.0323 633 0.012 634 0.0835 635 0.05 636 0.0184 637 0.0811 638 0.00261 639 0.0581 640 0.05 641 0.00999 642 0.0949 643 0.0069 644 0.00408 645 0.034 646 0.13 647 0.00699 648 0.203 649 0.0706 650 0.0583 651 0.0648 652 0.0346 653 0.715 654 0.0679 655 0.0688 656 0.0385 657 0.036 658 0.0608 659 0.223 660 0.0709 661 0.0672 662 0.0934 663 0.09 664 0.0715 665 0.00728 666 0.00518 667 0.0458 668 0.0803 669 0.686 670 0.00992 671 0.684 672 0.08 673 0.122 674 0.0324 675 0.0698 676 0.0787 677 6.13E−04 678 0.0151 679 0.0109 680 0.629 681 0.145 682 0.771 683 0.0361 684 0.32 685 0.074 686 0.0772 687 0.00219 688 5.48 689 0.00721 690 0.0138 691 0.0777 692 0.0198 693 0.652 694 0.0247 695 0.00582 696 0.667 697 0.633 698 0.000670 699 0.00527 700 0.00325 701 0.0761902 702 0.088 703 0.0903 704 0.0915 705 0.0958 706 0.00654 707 0.0741 708 0.00597 709 0.00336 710 0.00276 711 0.00325 712 0.0058 713 0.00286 714 0.0174 715 0.00349 716 0.021 717 0.0724 718 0.00125 719 0.00237 720 0.00582 721 0.0307 722 0.00388 723 0.0716 724 0.0632 725 0.006 726 0.0719 727 0.0582 728 0.021 729 0.0459 730 0.0295 731 0.05 732 0.0059 733 0.0202 734 0.000553 735 0.688 736 8.36 737 0.00405 738 0.0859 739 0.0676 740 0.00813 741 0.0749 742 0.0105 743 0.00681 744 0.505 745 0.632 746 0.116 747 0.942 748 0.0507 749 0.077 750 0.794 751 0.755 752 6.66 753 0.0746 754 0.00125 755 0.00249 756 0.0189 757 0.000435 758 0.0232 759 0.00165 760 0.00119 761 0.0277 762 0.00112 763 0.00231 764 0.0687 765 0.00291 766 0.00636 767 0.0672 768 0.000905 769 0.00526 770 0.006 771 0.00347 772 0.0024 773 0.00953 774 0.00707 775 0.0609 776 0.0021 777 0.00126 778 0.000896 779 0.000499 780 0.0817 781 0.00727 782 0.0247 783 0.0098 784 0.00238 785 0.000839 786 0.00751 787 0.00675 788 0.00544 789 0.0694 790 0.0026 791 0.000898 792 0.00957 793 0.00102 794 0.000883 795 0.0062 796 0.00465 797 0.00698 798 0.00963 799 0.00696 800 0.00621 801 0.0573 802 0.00583 803 0.0176 804 0.0497 805 7.82 806 1.4 807 0.1 808 0.0011 809 0.0332 810 0.327 811 0.0114 812 0.0388 813 0.00221 814 0.0045 815 0.00589 816 0.00482 817 0.00927 818 0.716 819 0.013 820 0.802 821 0.192 822 0.0711 823 0.00462 824 0.0124 825 0.00106 826 0.00679 827 0.000625 828 0.00644 829 0.00177 830 0.000269 831 0.000886 832 0.0101 833 0.07 834 0.0127 835 0.00395 836 0.0683 837 0.00277 838 0.0027 839 0.000607 840 0.00275 841 0.00613 842 0.0714 843 0.0172 844 0.0148172 845 0.00389 846 0.0744 847 0.0936 848 0.0292 849 0.0636 850 0.054 851 0.133 852 0.00832 853 0.00996 854 0.000414 855 0.111 856 0.657 857 0.00155 858 0.00059 859 0.0104 860 0.00824 861 0.000574 862 0.000780 863 0.000642 864 0.0672 865 0.000861 866 0.000525 867 0.0687 868 0.0869 869 6.87 870 0.994 871 7.3 872 >10 873 3.87 874 6.65 875 1.14 876 0.0477 877 >10 878 >10 879 0.0633 880 0.75 881 8.49 882 >10 883 0.000220 884 0.000968 885 0.005333 886 0.000194 887 0.000214 888 0.000494 889 0.651 890 0.0318 891 0.0872 892 0.00676 893 0.000662 894 0.202 895 0.73 896 1.58 897 0.716 898 0.223 899 0.181 900 0.0174 901 0.865 902 0.0108 903 0.0352 904 0.282 905 0.000994 906 0.00417 907 0.00709 908 0.0112 909 7.21 910 >10 911 0.0425 912 0.008725 913 0.0144 914 0.0772 915 0.174 916 0.00673 917 0.00679 918 0.233 919 0.101 920 0.00794 921 0.157 922 0.00995 923 0.00458 924 0.018 925 0.00206 926 0.00969 927 0.00713 928 0.106 929 0.0247 930 0.00209 931 0.00677 932 0.0303 933 0.0717 934 0.00638 935 0.0103 936 0.0325 937 0.0809 938 0.00627 939 >10 940 0.000691 941 0.000519 942 0.00102 943 0.0244 944 0.00336 945 0.00238 946 0.00594 947 0.00328 948 0.00539 949 0.0254 950 0.634 951 0.0639 952 0.0103 953 0.00235 954 0.00276 955 0.00256 956 0.00883 957 0.00351 958 0.0214 959 0.00976 960 0.00613 961 0.00894 962 0.0161 963 0.0195 964 0.00622 965 0.00831 966 0.00209 967 0.00396 968 0.00177 969 0.00636 970 0.0109 971 0.0226 972 0.0289 973 0.0218 974 0.0287 975 0.0503 976 0.0349 977 0.00265 978 0.00202 979 0.0757 980 0.0294 981 0.00654 982 0.1 983 0.724 984 0.0554 985 0.0283 986 0.0214 987 0.543 988 0.0601 989 0.0682 990 0.0179 991 0.0669 992 0.584 993 0.074 994 0.0121 995 0.0108 996 0.062 997 0.0194 998 0.123 999 0.684 1000 0.0818 1001 0.0953 1002 0.154 1003 0.00496 1004 0.0567 1005 0.0747 1006 0.0737 1007 0.0373 1008 0.00294 1009 0.0012 1010 0.0058 1011 0.00197 1012 0.00836 1013 0.00232 1014 0.00207 1015 0.00168 1016 0.00219 1017 0.00229 1018 0.00164 1019 0.00198 1020 0.000901 1021 0.00111 1022 0.00293 1023 0.00687 1024 0.00352 1025 0.000808 1026 0.00156 1027 0.00228 1028 0.00736 1029 0.000272 1030 0.002040 1031 0.00773 1032 0.00888 1033 0.00197 1034 0.00629 1035 0.00304 1036 0.016 1037 0.00776 1038 0.00784 1039 0.00687 1040 0.0134 1041 0.00241 1042 0.00359 1043 0.0104 1044 0.000892 1045 0.00669 1046 0.00461 1047 0.000205 1048 0.00827 1049 0.00239 1050 0.0234 1051 0.000313 1052 0.0271 1053 0.00341 1054 0.026 1055 0.00438 1056 0.0013 1057 0.0258 1058 0.00249 1059 0.0164 1060 0.00229 1061 0.00784 1062 0.017 1063 0.00189 1064 0.00412 1065 0.00143 1066 0.0057 1067 0.37 1068 0.00577 1069 0.00123 1070 0.000857 1071 0.000473 1072 0.00624 1073 0.00388 1074 0.0144 1075 0.00762 1076 0.0057 1077 0.0691 1078 0.00761 1079 0.0182 1080 0.00341 1081 0.195 1082 0.00218 1083 0.000920 1084 0.0148 1085 0.0256 1086 0.00993 1087 0.00168 1088 0.0344 1089 0.00827 1090 0.00542 1091 0.00419 1092 0.0177 1093 0.565 1094 0.0688 1095 0.00445 1096 0.00207 1097 0.0647 1098 0.00955 1099 0.0156 1100 0.0087 1101 0.00206 1102 0.00177 1103 0.00424 1104 0.00696 1105 0.0026 1106 0.0275 1107 0.00226 1108 0.0201 1109 0.00921 1110 0.111 1111 0.062 1112 0.0164 1113 0.0231 1114 0.0218 1115 0.0212 1116 0.00619 1117 0.0657 1118 0.00418 1119 0.00667 1120 0.00237 1121 0.00842 1122 0.00996 1123 0.00711 1124 0.000344 1125 0.00477 1126 0.00236 1127 0.00299 1128 0.00605 1129 0.00805 1130 0.00296 1131 0.0344 1132 0.00896 1133 0.001 1134 0.00551 1135 0.00423 1136 0.00302 1137 0.000277 1138 0.00385 1139 0.00141 1140 0.00584 1141 0.0022 1142 0.0029 1143 0.0174 1144 0.0096 1145 0.00704 1146 0.00188 1147 0.00283 1148 0.00272 1149 0.00262 1150 0.0641 1151 0.00778 1152 0.00308 1153 0.00172 1154 0.17043 1156 0.0354 1157 0.0531 1158 0.00204 1159 0.01740 1160 0.01630 1161 0.061 1162 0.0618 1163 0.0027 1164 0.158 1165 0.577 1166 0.0261 - Compounds which inhibit NAMPT are useful for treating diseases in which activation of NF-KB is implicated. Such methods are useful in the treatment of a variety of diseases including inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukaemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia.
- Involvement of NAMPT in the treatment of cancer is described in WO 97/48696. Involvement of NAMPT in immuno-supression is described in WO 97/48397. Involvement of NAMPT for the treatment of diseases involving angiogenesis is described in WO 2003/80054. Involvement of NAMPT for the treatment of rheumatoid arthritis and septic shock is described in WO 2008/025857. Involvement of NAMPT for the prophlaxis and treatment of ischaemia is described in WO 2009/109610.
- Cancers include, but are not limited to, hematologic and solid tumor types such as acoustic neuroma, acute leukemia, acute lymphoblastic leukemia, acute myelogenous leukemia (monocytic, myeloblastic, adenocarcinoma, angiosarcoma, astrocytoma, myelomonocytic and promyelocytic), acute t-cell leukemia, basal cell carcinoma, bile duct carcinoma, bladder cancer, brain cancer, breast cancer (including estrogen-receptor positive breast cancer), bronchogenic carcinoma, Burkitt's lymphoma, cervical cancer, chondrosarcoma, chordoma, choriocarcinoma, chronic leukemia, chronic lymphocytic leukemia, chronic myelocytic (granulocytic) leukemia, chronic myelogenous leukemia, colon cancer, colorectal cancer, craniopharyngioma, cystadenocarcinoma, dysproliferative changes (dysplasias and metaplasias), embryonal carcinoma, endometrial cancer, endotheliosarcoma, ependymoma, epithelial carcinoma, erythroleukemia, esophageal cancer, estrogen-receptor positive breast cancer, essential thrombocythemia, Ewing's tumor, fibrosarcoma, gastric carcinoma, germ cell testicular cancer, gestational trophobalstic disease, glioblastoma, head and neck cancer, heavy chain disease, hemangioblastoma, hepatoma, hepatocellular cancer, hormone insensitive prostate cancer, leiomyosarcoma, liposarcoma, lung cancer (including small cell lung cancer and non-small cell lung cancer), lymphangioendothelio-sarcoma, lymphangiosarcoma, lymphoblastic leukemia, lymphoma (lymphoma, including diffuse large B-cell lymphoma, follicular lymphoma, Hodgkin's lymphoma and non-Hodgkin's lymphoma), malignancies and hyperproliferative disorders of the bladder, breast, colon, lung, ovaries, pancreas, prostate, skin and uterus, lymphoid malignancies of T-cell or B-cell origin, leukemia, medullary carcinoma, medulloblastoma, melanoma, meningioma, mesothelioma, multiple myeloma, myelogenous leukemia, myeloma, myxosarcoma, neuroblastoma, oligodendroglioma, oral cancer, osteogenic sarcoma, ovarian cancer, pancreatic cancer, papillary adenocarcinomas, papillary carcinoma, peripheral T-cell lymphoma, pinealoma, polycythemia vera, prostate cancer (including hormone-insensitive (refractory) prostate cancer), rectal cancer, renal cell carcinoma, retinoblastoma, rhabdomyosarcoma, sarcoma, sebaceous gland carcinoma, seminoma, skin cancer, small cell lung carcinoma, solid tumors (carcinomas and sarcomas), stomach cancer, squamous cell carcinoma, synovioma, sweat gland carcinoma, testicular cancer (including germ cell testicular cancer), thyroid cancer, Waldenström's macroglobulinemia, testicular tumors, uterine cancer, Wilms' tumor and the like.
- The following abbreviations have the meanings indicated. ADDP means 1,1′-(azodicarbonyl)dipiperidine; AD-mix-3 means a mixture of (DHQD)2PHAL, K3Fe(CN)6, K2CO3, and K2SO4; 9-BBN means 9-borabicyclo(3.3.1)nonane; Boc means tert-butoxycarbonyl; (DHQD)2PHAL means hydroquinidine 1,4-phthalazinediyl diethyl ether; DBU means 1,8-diazabicyclo[5.4.0]undec-7-ene; DIBAL means diisobutylaluminum hydride; DIEA means diisopropylethylamine; DMAP means N,N-dimethylaminopyridine; DMF means N,N-dimethylformamide; dmpe means 1,2-bis(dimethylphosphino)ethane; DMSO means dimethylsulfoxide; dppb means 1,4-bis(diphenylphosphino)-butane; dppe means 1,2-bis(diphenylphosphino)ethane; dppf means 1,1′-bis(diphenylphosphino)ferrocene; dppm means 1,1-bis(diphenylphosphino)methane; EDAC-HCl means 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; Fmoc means fluorenylmethoxycarbonyl; HATU means O-(7-azabenzotriazol-1-yl)-N,N′N′N′-tetramethyluronium hexafluorophosphate; HMPA means hexamethylphosphoramide; IPA means isopropyl alcohol; MP-BH3 means macroporous triethylammonium methylpolystyrene cyanoborohydride; TEA means triethylamine; TFA means trifluoroacetic acid; THF means tetrahydrofuran; NCS means N-chlorosuccinimide; NMM means N-methylmorpholine; NMP means N-methylpyrrolidine; PPh3 means triphenylphosphine.
- The following schemes are presented to provide what is believed to be the most useful and readily understood description of procedures and conceptual aspects of this invention. Compounds of this invention may be made by synthetic chemical processes, examples of which are shown herein. It is meant to be understood that the order of the steps in the processes may be varied, that reagents, solvents and reaction conditions may be substituted for those specifically mentioned, and that vulnerable moieties may be protected and deprotected, as necessary.
-
- As shown in Scheme 1, compounds of formula (1), wherein R4 is as described herein, can be reacted with 4-nitrobenzoic acid in the presence of a base such as but not limited to N-methylmorpholine, an ester activating agent such as but not limited to 1-hydroxybenzotriazole hydrate, and a carboxyl activating agent such as but not limited to N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, to provide compounds of formula (2). The reaction is typically performed at ambient temperature in a solvent such as but not limited to dimethylformamide. Compounds of formula (3) can be prepared by reacting compounds of formula (2) with hydrogen in the presence of palladium on carbon.
- The reaction is typically performed at ambient temperature in a solvent such as but not limited to methanol. Compounds of formula (3) can be reacted with compounds of formula (4) wherein X and Z are as described herein, to provide compounds of formula (5). The reaction is typically performed in the presence of bis(2,5-dioxopyrrolidin-1-yl) carbonate and a base such as but not limited to pyridine. The reaction is typically performed at ambient temperature in a solvent such as but not limited to N-methyl-2-pyrrolidinone.
- Alternatively, Compounds of formula (3) can be reacted with compounds of formula (6) wherein X is as described herein, to provide compounds of formula (7). The reaction is typically performed in the presence of bis(2,5-dioxopyrrolidin-1-yl) carbonate and a base such as but not limited to pyridine. The reaction is typically performed at ambient temperature in a solvent such as but not limited to N-methyl-2-pyrrolidinone.
- Compounds of formula (8), wherein Rx is as described herein for substituents on the R3 phenyl, can be reacted with compounds of formula (9), wherein X and Z are as described herein, to provide compounds of formula (10). The reaction is typically performed in the presence of a base such as but not limited to N-methylmorpholine, an ester activating agent such as but not limited to 1-hydroxybenzotriazole hydrate, and a carboxyl activating agent such as but not limited to N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride. The reaction is typically performed at ambient temperature in a solvent such as but not limited to dimethylformamide.
- Similarly, compounds of formula (8), wherein Rx is as described herein for substituents on the R3 phenyl, can be reacted with compounds of formula (11), wherein X is as described herein, to provide compounds of formula (12). The reaction is typically performed in the presence of a base such as but not limited to N-methylmorpholine, an ester activating agent such as but not limited to 1-hydroxybenzotriazole hydrate, and a carboxyl activating agent such as but not limited to N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride. The reaction is typically performed at ambient temperature in a solvent such as but not limited to dimethylformamide.
- As shown in Scheme 3, compounds of formula (13), wherein R3 is as described herein, can be reacted with compounds of formula (11), wherein X is as described herein, in the presence of bis(2,5-dioxopyrrolidin-1-yl) carbonate and a base such as but not limited to pyridine to provide compounds of formula (14). The reaction is typically performed at ambient temperature in a solvent such as but not limited to N-methyl-2-pyrrolidinone.
- Alternatively, compounds of formula (13), wherein R3 is as described herein, can be reacted with compounds of formula (9), wherein X and Z are as described herein, in the presence of bis(2,5-dioxopyrrolidin-1-yl) carbonate and a base such as but not limited to pyridine to provide compounds of formula (14). The reaction is typically performed at ambient temperature in a solvent such as but not limited to N-methyl-2-pyrrolidinone.
- 2-Bromo-5-thiazolecarboxylic acid can be reacted with compounds of formula (9), N-methylmorpholine, an ester activating agent such as but not limited to 1-hydroxybenzotriazole hydrate, and a carboxyl activating agent such as but not limited to N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, to provide compounds of formula (16). The reaction is typically performed at ambient temperature in a solvent such as but not limited to dimethylformamide. Compounds of formula (16) can be reacted with amines of formula (1) wherein R4 is as described herein, to provide compounds of formula (17). The reaction is typically performed at an elevated temperature in a solvent such as but not limited to acetonitrile and may be performed in a microwave oven. Compounds of formula (19), which are representative of the compounds of this invention, can be prepared by reacting compounds of formula (17) with compounds of formula (18), wherein R4 is as described herein, in the presence of a base such as but not limited to diisopropylethylamine. The reaction is typically performed at ambient temperature in a solvent such as but not limited to tetrahydrofuran. Alternatively, compounds of formula (17) can be reacted with amines of formula (4), wherein R4 is as described herein, to provide compounds of formula (20), which are representative of the compounds of Formula (I). The reaction is typically performed in the presence of bis(2,5-dioxopyrrolidin-1-yl) carbonate and a base such as but not limited to pyridine. The reaction is typically performed at ambient temperature in a solvent such as but not limited to N-methyl-2-pyrrolidinone.
- As shown in Scheme 5, compounds of formula (16), which can be prepared as described in Scheme 4 and wherein X and Z are as described herein, can be reacted with suitable boronic acids (or the equivalent boronic ester) of formula (21) wherein R4 is as described herein, under Suzuki coupling conditions known to those skilled in the art and widely available in the literature, to provide compounds of formula (22), which are representative of the compounds of Formula (I).
- The following examples are presented to provide what is believed to be the most useful and readily understood description of procedures and conceptual aspects of this invention. Each exemplified compound and intermediate was named using ACD/ChemSketch Version 12.5 (20 Apr. 2011) or (3 Sep. 2012), Advanced Chemistry Development Inc., Toronto, Ontario), or ChemDraw Ver. 9.0.7 (CambridgeSoft, Cambridge, Mass.).
- 4-Nitrobenzoic acid (0.8 g, 4.79 mmol) and 1-hydroxybenzotriazole hydrate (1.1 g, 7.18 mmol) in dimethylformamide (20 mL) was treated with N-methylmorpholine (1.8 mL, 16.75 mmol) and 3-methylbutan-1-amine (0.724 mL, 6.22 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.38 g, 7.18 mmol). The reaction mixture was stirred at room temperature for 17 hours. Water was added and the resulting suspension was stirred for 2 hours. The suspension was filtered and the solid collected was washed with water and dried to provide the title compound.
- N-Isopentyl-4-nitrobenzamide (1 g, 4.23 mmol) and methanol (40 ml) were added to palladium on carbon (0.200 g, 1.879 mmol) in a 250 mL SS pressure bottle and the mixture was stirred for 6 hours with hydrogen at 30 psi and room temperature. The mixture was filtered through a nylon membrane and concentrated to provide the title compound.
- A solution of 4-amino-N-isopentylbenzamide (0.05 g, 0.242 mmol),bis(2,5-dioxopyrrolidin-1-yl) carbonate (0.078 g, 0.303 mmol) and pyridine (0.020 ml, 0.242 mmol) in N-methyl-2-pyrrolidinone (0.6 mL) was stirred at room temperature for 1 hour. Diisopropylethylamine (0.127 ml, 0.727 mmol) was added followed by addition of a solution of imidazo[1,2-a]pyridin-6-amine (0.041 g, 0.279 mmol) in N-methyl-2-pyrrolidinone (0.6 mL) dropwise by syringe over 5 minutes. The reaction mixture was stirred for 16 hours at room temperature and the mixture was treated with water. The resulting suspension was stirred for 5 minutes and filtered with water washes. Vacuum drying and reverse phase chromatography provided the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.04-8.93 (m, 2H), 8.76 (bs, 1H), 8.24 (t, J=5.5 Hz, 1H), 7.96 (s, 1H), 7.79 (d, J=8.7 Hz, 2H), 7.58-7.45 (m, 4H), 7.09 (dd, J=9.6, 2.0 Hz, 1H), 3.33-3.20 (m, 2H), 1.68-1.52 (m, 1H), 1.46-1.35 (m, 2H), 0.90 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 366 (M+H)+.
- The title compound was prepared as described in Example 1C, substituting imidazo[1,2-a]pyridin-7-amine for imidazo[1,2-a]pyridin-6-amine. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.04 (m, 2H), 8.42 (dd, J=7.5, 0.6 Hz, 1H), 8.25 (t, J=5.5 Hz, 1H), 7.78 (m, 4H), 7.53 (d, J=8.7 Hz, 2H), 7.42 (d, J=1.2 Hz, 1H), 6.90 (dd, J=7.3, 2.1 Hz, 1H), 3.30-3.21 (m, 2H), 1.69-1.54 (m, 1H), 1.47-2.36 (m, 2H), 0.91 (d, J=6.5 Hz, 6H); MS (ESI(+)) m/e 366 (M+H)+.
- A 0° C. solution of imidazo[1,2-a]pyridin-6-amine (1 g, 7.21 mmol), N-ethyl-N-isopropylpropan-2-amine (2.51 ml, 14.42 mmol) and dimethylformamide (21.85 ml) was treated with a solution of 1-isocyanato-4-nitrobenzene (1.313 g, 8.00 mmol) in tetrahydrofuran (10.92 ml) which was added dropwise via syringe over 5 minutes. The reaction mixture was allowed to stir at room temperature for 6 hours, and water was added. The suspension was filtered with water washes to give the title compound after vacuum drying.
- The title compound was prepared as described in Example 1B, substituting 1-(imidazo[1,2-a]pyridin-6-yl)-3-(4-nitrophenyl)urea for N-isopentyl-4-nitrobenzamide.
- The title compound was prepared as described in Example 1A, substituting 1-(4-aminophenyl)-3-(imidazo[1,2-a]pyridin-6-yl)urea for 3-methylbutan-1-amine and 2-cyclopentylacetic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6, Temp=90° C.) δ ppm 9.73 (bs, 1H), 8.96 (m, 1H), 8.66 (s, 1H), 8.62 (s, 1H), 7.95 (s, 1H), 7.57-7.44 (m, 4H), 7.37 (d, J=8.9 Hz, 2H), 7.07 (dd, J=9.6, 2.0 Hz, 1H), 2.29-2.15 (m, 3H), 1.82-1.68 (m, 2H), 1.68-1.45 (m, 4H), 1.29-1.07 (m, 2H); MS (ESI(+)) m/e 378 (M+H)+.
-
TABLE 1 The following Examples were prepared essentially as described in Example 3, substituting the appropriate carboxylic acid in Example 1C. Some products were purified by flash chromatography while others were purified by reverse-phase HPLC. Accordingly, some Examples were isolated as trifluoroacetic acid salts. Ex Name 1H NMR MS 26 N-{4-[(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6, (ESI(+)) a]pyridin-6- Temp = 90° C.) δ ppm 9.49 (bs, 1H), m/e 380 ylcarbamoyl)amino]phenyl}- 8.84 (m, 1H), 8.44 (m, 2H), 7.85 (s, (M + H)+ 2-(tetrahydrofuran-3- 1H), 7.52-7.44 (m, 4H), 7.39-7.29 yl)acetamide (m, 2H), 7.09 (dd, J = 9.6, 2.1 Hz, 1H), 3.83-3.72 (m, 2H), 3.68-3.62 (m, 1H), 3.38-3.33 (m, 1H), 2.57 (m, 1H), 2.40-2.33 (m, 2H), 2.08- 1.95 (m, 1H), 1.62-1.52 (m, 1H) 27 N-{4-[(imidazo[1,2- 1H NMR (300 MHz, DMSO-d6) δ (ESI(+)) a]pyridin-6- ppm δ 9.81 (s, 1H), 8.98-8.93 (m, m/e 310 ylcarbamoyl)amino]phenyl} 1H), 8.70-8.62 (m, 2H), 7.96-7.93 (M + H)+ acetamide (m, 1H), 7.53-7.45 (m, 4H), 7.41- 7.33 (m, 2H), 7.07 (dd, J = 9.5, 2.0 Hz, 1H), 2.01 (s, 3H) 39 2-ethoxy-N-{4- 1H NMR (400 MHz, DMSO-d6, (ESI(+)) [(imidazo[1,2-a]pyridin-6- Temp = 90° C.) δ ppm 9.57 (s, 1H), 8.96 m/e 354 ylcarbamoyl)amino]phenyl} (m, 1H), 8.69 (s, 1H), 8.64 (s, 1H), (M + H)+ acetamide 7.95 (s, 1H), 7.60-7.48 (m, 4H), 7.42-7.37 (m, 2H), 7.07 (dd, J = 9.6, 2.0 Hz, 1H), 4.00 (s, 2H), 3.56 (q, J = 7.0 Hz, 2H), 1.19 (t, J = 7.0 Hz, 3H) 40 N-{4-[(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6,) δ (ESI(+)) a]pyridin-6- ppm 9.79 (s, 1H), 8.98-8.93 (m, m/e 394 ylcarbamoyl)amino]phenyl}- 1H), 8.67 (s, 1H), 8.63 (s, 1H), 7.97- (M + H)+ 2-(tetrahydro-2H-pyran-4- 7.93 (m, 1H), 7.54-7.46 (m, 4H), yl)acetamide 7.40-7.34 (m, 2H), 7.07 (dd, J = 9.5, 2.0 Hz, 1H), 3.87-3.79 (m, 2H), 3.34-3.26 (m, 2H), 2.25-2.19 (m, 2H), 2.07-1.91 (m, 1H), 1.63-1.54 (m, 2H), 1.31-1.17 (m, 2H) 41 N-{4-[(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6, (ESI(+)) a]pyridin-6- Temp = 90° C.) δ ppm 9.35 (bs, 1H), m/e 395 ylcarbamoyl)amino]phenyl}- 8.85 (m, 1H), 8.50-8.30 (M, 2H), (M + H)+ 2-(morpholin-4- 7.86 (s, 1H), 7.55-7.43 (m, 4H), yl)acetamide 7.41-7.34 (m, 2H), 7.09 (dd, J = 9.5, 2.0 Hz, 1H), 3.68-3.60 (m, 4H), 3.09 (s, 2H), 2.56-2.51 (m, 4H) 42 N-{4-[(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 384 ylcarbamoyl)amino]phenyl}- (M + H)+ 2-(2-methoxyethoxy)acetamide 43 N-{4-[(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 368 ylcarbamoyl)amino]phenyl}- (M + H)+ 3-methoxy-2- methylpropanamide 44 N-{4-[(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 338 ylcarbamoyl)amino]phenyl} (M + H)+ butanamide 45 4,4,4-trifluoro-N-{4- (ESI(+)) [(imidazo[1,2-a]pyridin-6- m/e 392 ylcarbamoyl)amino]phenyl} (M + H)+ butanamide 46 -{4-[(imidazo[1,2-a]pyridin- (ESI(+)) 6-ylcarbamoyl)amino]phenyl} m/e 380 tetrahydro-2H-pyran-4- (M + H)+ carboxamide 47 N-{4-[(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 366 ylcarbamoyl)amino]phenyl}- (M + H)+ 4-methylpentanamide 48 N-{4-[(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 393 ylcarbamoyl)amino]phenyl}- (M + H)+ 1-methylpiperidine-4- carboxamide 49 N-{4-[(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 428 ylcarbamoyl)amino]phenyl} (M + H)+ tetrahydro-2H-thiopyran-4- carboxamide 1,1-dioxide 50 N-{4-[(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 382 ylcarbamoyl)amino]phenyl}- (M + H)+ 1,4-dioxane-2-carboxamide - The title compound was prepared as described in Example 3A, substituting methyl 4-isocyanatobenzoate for 1-isocyanato-4-nitrobenzene.
- A solution of methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate (2.1 g, 6.77 mmol) in tetrahydrofuran (18.05 ml) and methanol (9.02 ml) was treated with 2N lithium hydroxide (13.53 ml, 27.1 mmol) and the reaction was allowed to stir at room temperature for 16 hours. The mixture was concentrated, redissolved in 225 mL water and acidified to -pH 4 with 3N hydrochloric acid. The suspension was filtered with water washes to give the title compound after vacuum drying.
- The title compound was prepared as described in Example 1A, substituting 2-phenylethanamine for 3-methylbutan-1-amine and 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6/D2O, Temp=90° C.) δ ppm 9.33 (dd, J=1.9, 0.8 Hz, 1H), 8.32 (d, J=1.8 Hz, 1H), 8.05 (d, J=2.0 Hz, 1H), 7.90 (d, J=9.7 Hz, 1H), 7.85-7.74 (m, 3H), 7.61-7.51 (m, 2H), 7.35-7.20 (m, 5H), 3.49 (dd, J=8.1, 6.9 Hz, 2H), 2.94-2.79 (m, 2H); MS (ESI(+)) m/e 400 (M+H)+.
-
TABLE 2 The following Examples were prepared essentially as described in Example 4, substituting the appropriate amine in Example 4C. Some products were purified by flash chromatography while others were purified by reverse-phase HPLC. Accordingly, some Examples were isolated as trifluoroacetic acid salts. Ex Name 1H NMR MS 5 4-[(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6- Temp = 90° C.) δ ppm 9.37 (dd, J = 2.0, 0.9 Hz, m/e 409 ylcarbamoyl)amino]- 1H), 8.36 (d, J = 2.1 Hz, 1H), 8.10 (d, J = 2.1 (M + H)+ N-[2- Hz, 1H), 7.94 (d, J = 9.6 Hz, 1H), 7.88-7.78 (morpholin-4- (m, 3H), 7.71-7.57 (m, 2H), 4.02 (d, J = 11.3 yl)ethyl]benzamide Hz, 2H), 3.66 (dd, J = 16.1, 10.0 Hz, 4H), 3.56 (d, J = 11.3 Hz, 2H), 3.33 (t, J = 6.1 Hz, 2H), 3.17 (d, J = 13.5 Hz, 2H), 2.70 (s, 2H) 6 N-(1-hydroxy-2- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) methylpropan-2- Temp = 90° C.) δ ppm 9.36 (t, J = 6.6 Hz, 1H), m/e 368 yl)-4- 8.34 (d, J = 1.9 Hz, 1H), 8.09 (dd, J = 10.9, 5.4 (M + H)+ [(imidazo[1,2- Hz, 1H), 7.90 (t, J = 10.7 Hz, 1H), 7.85-7.73 a]pyridin-6- (m, 3H), 7.56 (dd, J = 12.5, 5.6 Hz, 2H), 3.51 (s, ylcarbamoyl)ami- 2H), 1.49-1.23 (m, 6H) no]benzamide 7 N-benzyl-4- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) [(imidazo[1,2- Temp = 90° C.) δ ppm 9.38-9.29 (m, 1H), 8.33 m/e 386 a]pyridin-6- (d, J = 2.0 Hz, 1H), 8.07 (d, J = 2.0 Hz, 1H), (M + H)+ ylcarbamoyl)ami- 7.96-7.85 (m, 3H), 7.77 (td, J = 9.4, 1.5 Hz, no]benzamide 1H), 7.66-7.51 (m, 2H), 7.38-7.31 (m, 4H), 7.32-7.19 (m, 1H), 4.48 (s, 2H) 8 N-(cyclopentylmethyl)- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) 4-[(imidazo[1,2- Temp = 90° C.) δ ppm 9.41-9.31 (m, 1H), 8.34 m/e 378 a]pyridin-6- (d, J = 2.0 Hz, 1H), 8.07 (d, J = 2.0 Hz, 1H), (M + H)+ ylcarbamoyl)ami- 7.91 (d, J = 8.9 Hz, 1H), 7.86-7.73 (m, 3H), no]benzamide 7.63-7.51 (m, 2H), 3.19 (d, J = 7.4 Hz, 2H), 2.24-2.01 (m, 1H), 1.68 (dt, J = 11.6, 7.2 Hz, 2H), 1.64-1.57 (m, 2H), 1.57-1.42 (m, 2H), 1.37-1.14 (m, 2H) 9 4-[(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6- Temp = 90° C.) δ ppm 9.36 (d, J = 1.4 Hz, 1H), m/e 421 ylcarbamoyl)amino]- 8.35 (d, J = 2.0 Hz, 1H), 8.10 (d, J = 2.1 Hz, (M + H)+ N-[3-(piperidin-1- 1H), 7.94 (d, J = 9.7 Hz, 1H), 7.88-7.80 (m, yl)propyl]benzamide 3H), 7.66-7.53 (m, 2H), 3.44 (d, J = 12.2 Hz, 2H), 3.34 (t, J = 6.6 Hz, 2H), 3.12-3.02 (m, 2H), 2.97-2.85 (m, 2H), 2.02-1.81 (m, 4H), 1.81-1.58 (m, 4H), 1.51-1.31 (m, 1H) 10 4-[(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6- Temp = 90° C.) δ ppm 9.36 (dd, J = 6.3, 5.4 Hz, m/e 411 ylcarbamoyl)amino]- 1H), 8.35 (d, J = 2.1 Hz, 1H), 8.09 (d, J = 2.0 (M + H)+ N-(2- Hz, 1H), 7.92 (d, J = 9.8 Hz, 1H), 7.89-7.80 phenoxyethyl)benz- (m, 3H), 7.63-7.55 (m, 2H), 7.30 (dd, J = 8.4, amide 7.4 Hz, 2H), 6.95 (dd, J = 11.9, 7.8 Hz, 3H), 4.12 (t, J = 5.8 Hz, 2H), 3.64 (t, J = 5.8 Hz, 2H) 11 4-[(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6- Temp = 90° C.) δ ppm 9.34 (s, 1H), 8.34 (d, J = m/e 393 ylcarbamoyl)amino]- 2.0 Hz, 1H), 8.09 (d, J = 2.0 Hz, 1H), 7.92 (d, J = (M + H)+ N-[2- 9.1 Hz, 1H), 7.88-7.78 (m, 3H), 7.59 (dd, J = (pyrrolidin-1- 16.4, 8.7 Hz, 2H), 3.59 (dd, J = 15.8, 9.8 Hz, yl)ethyl]benzamide 4H), 3.33 (t, J = 6.0 Hz, 2H), 3.07 (d, J = 11.0 Hz, 2H), 2.05 (s, 2H), 1.97-1.74 (m, 2H) 12 -[(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6- Temp = 90° C.) δ ppm 9.35 (d, J = 1.3 Hz, 1H), m/e 382 ylcarbamoyl)amino]- 8.34 (d, J = 2.0 Hz, 1H), 8.08 (d, J = 2.0 Hz, (M + H)+ N-[2-(propan-2- 1H), 7.92 (d, J = 9.7 Hz, 1H), 7.88-7.77 (m, yloxy)ethyl]benz- 3H), 7.63-7.52 (m, 2H), 3.64-3.55 (m, 1H), amide 3.51 (dd, J = 20.1, 13.7 Hz, 2H), 3.39 (t, J = 6.2 Hz, 2H), 1.09 (d, J = 6.1 Hz, 6H) 13 N-(2-hydroxy-2- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) methylpropyl)-4- Temp = 90° C.) δ ppm 9.37-9.31 (m, 1H), 8.33 m/e 368 [(imidazo[1,2- (d, J = 1.9 Hz, 1H), 8.06 (d, J = 2.0 Hz, 1H), (M + H)+ a]pyridin-6- 7.96-7.88 (m, 1H), 7.88-7.81 (m, 2H), 7.76 ylcarbamoyl)ami- (dd, J = 9.6, 1.9 Hz, 1H), 7.65-7.53 (m, 2H), no]benzamide 3.27 (s, 2H), 1.15 (d, J = 27.1 Hz, 6H) 14 N-[2-hydroxy-1-(4- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) methoxyphenyl)eth- Temp = 90° C.) δ ppm 9.40-9.32 (m, 1H), 8.34 m/e 446 yl]-4- (d, J = 2.0 Hz, 1H), 8.08 (d, J = 2.1 Hz, 1H), (M + H)+ [(imidazo[1,2- 7.95-7.86 (m, 3H), 7.81-7.75 (m, 1H), 7.61- a]pyridin-6- 7.55 (m, 2H), 7.39-7.26 (m, 2H), 6.92-6.86 ylcarbamoyl)ami- (m, 2H), 5.09-4.96 (m, 1H), 3.72-3.67 (m, no]benzamide 5H), 3.66-3.60 (m, 1H) 15 4-[(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6- Temp = 90° C.) δ ppm 9.41-9.33 (m, 1H), 8.35 m/e 407 ylcarbamoyl)amino]- (d, J = 2.0 Hz, 1H), 8.09 (d, J = 2.1 Hz, 1H), (M + H)+ N-[2-(2- 7.92 (d, J = 9.7 Hz, 1H), 7.82-7.72 (m, 3H), oxopyrrolidin-1- 7.63-7.51 (m, 2H), 3.50-3.30 (m, 6H), 2.20 yl)ethyl]benzamide (t, J = 8.1 Hz, 2H), 1.96-1.86 (m, 2H) 16 4-[(imidazo[1,2- NMR (500 MHz, DMSO-d6/D2O, Temp = 90° C.) (ESI(+)) a]pyridin-6- δ ppm 9.39-9.29 (m, 1H), 8.34 (d, J = 2.0 Hz, m/e 380 ylcarbamoyl)amino]- 1H), 8.08 (d, J = 2.0 Hz, 1H), 7.92 (d, J = 9.5 (M + H)+ N-(tetrahydrofuran- Hz, 1H), 7.86-7.77 (m, 3H), 7.63-7.53 (m, 2-ylmethyl)benzamide 2H), 3.99 (p, J = 6.3 Hz, 1H), 3.64 (dd, J = 14.3, 7.5 Hz, 2H), 3.42-3.24 (m, 2H), 2.03-1.87 (m, 1H), 1.89-1.75 (m, 2H), 1.66-1.52 (m, 1H) 17 4-[(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6- Temp = 90° C.) δ ppm 9.34 (d, J = 1.3 Hz, 1H), m/e 338 ylcarbamoyl)amino]- 8.34 (d, J = 2.0 Hz, 1H), 8.07 (d, J = 2.0 Hz, (M + H)+ N-propylbenzamide 1H), 7.91 (d, J = 9.6 Hz, 1H), 7.87-7.73 (m, 3H), 7.64-7.50 (m, 2H), 3.22 (t, J = 7.1 Hz, 2H), 1.61-1.45 (m, 2H), 0.89 (t, J = 7.4 Hz, 3H) 18 4-[(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6- Temp = 90° C.) δ ppm 9.35 (d, J = 1.2 Hz, 1H), m/e 423 ylcarbamoyl)amino]- 8.35 (d, J = 2.1 Hz, 1H), 8.10 (d, J = 2.1 Hz, (M + H)+ N-[3- 1H), 7.93 (d, J = 9.7 Hz, 1H), 7.85-7.78 (m, (morpholin-4- 3H), 7.65-7.56 (m, 2H), 4.07-3.96 (m, 2H), yl)propyl]benzamide 3.66 (t, J = 12.1 Hz, 2H), 3.44 (d, J = 12.4 Hz, 2H), 3.35 (t, J = 6.6 Hz, 2H), 3.21-3.12 (m, 2H), 3.07 (d, J = 9.4 Hz, 2H), 2.03-1.83 (m, 2H) 19 4-[(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6- Temp = 90° C.) δ ppm 9.30 (s, 1H), 8.29 (d, J = m/e 372 ylcarbamoyl)amino]- 1.6 Hz, 1H), 8.02-7.92 (m, 3H), 7.87 (d, J = (M + H)+ N-phenylbenzamide 9.6 Hz, 1H), 7.79-7.66 (m, 3H), 7.65-7.58 (m, 2H), 7.42-7.33 (m, 2H), 7.20-7.05 (m, 1H) 20 4-[(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6- Temp = 90° C.) δ ppm 9.39-9.29 (m, 1H), 8.43- m/e 366 ylcarbamoyl)amino]- 8.29 (m, 1H), 8.09-8.03 (m, 1H), 7.96-7.89 (M + H)+ N-(2- (m, 1H), 7.87-7.75 (m, 3H), 7.66-7.50 (m, methylbutyl)benz- 2H), 3.25-3.16 (m, 1H), 3.14-3.03 (m, 1H), amide 1.70-1.58 (m, 1H), 1.48-1.36 (m, 1H), 1.23- 1.05 (m, 1H), 0.97-0.79 (m, 6H) 21 4-[(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6- Temp = 90° C.) δ ppm 9.44-9.30 (m, 1H), 8.34 m/e 421 ylcarbamoyl)amino]- (t, J = 5.8 Hz, 1H), 8.13-8.05 (m, 1H), 7.92 (d, (M + H)+ N-[3-(2- J = 9.7 Hz, 1H), 7.87-7.76 (m, 3H), 7.68- oxopyrrolidin-1- 7.51 (m, 2H), 3.45-3.32 (m, 2H), 3.31-3.14 yl)propyl]benzamide (m, 4H), 2.33-2.19 (m, 2H), 2.02-1.87 (m, 2H), 1.80-1.63 (m, 2H) 22 4-[(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6- Temp = 90° C.) δ ppm 9.34 (d, J = 1.2 Hz, 1H), m/e 394 ylcarbamoyl)amino]- 8.33 (d, J = 2.0 Hz, 1H), 8.07 (d, J = 2.0 Hz, (M + H)+ N-(tetrahydro- 1H), 7.91 (d, J = 9.6 Hz, 1H), 7.85-7.75 (m, 2H-pyran-4- 3H), 7.62-7.53 (m, 2H), 3.85 (dd, J = 11.4, 2.5 ylmethyl)benzamide Hz, 2H), 3.27 (td, J = 11.7, 1.9 Hz, 2H), 3.16 (d, J = 6.9 Hz, 2H), 1.80 (tt, J = 11.3, 3.9 Hz, 1H), 1.59 (d, J = 11.0 Hz, 2H), 1.20 (qd, J = 12.0, 4.5 Hz, 2H) 23 4-[(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6- Temp = 90° C.) δ ppm 9.43-9.28 (m, 1H), 8.34 m/e 394 ylcarbamoyl)amino]- (d, J = 2.0 Hz, 1H), 8.08 (d, J = 2.0 Hz, 1H), (M + H)+ N-(tetrahydro- 7.92 (d, J = 9.7 Hz, 1H), 7.87-7.74 (m, 3H), 2H-pyran-2- 7.65-7.51 (m, 2H), 3.87 (dd, J = 10.6, 2.6 Hz, ylmethyl)benzamide 1H), 3.48-3.41 (m, 1H), 3.33 (td, J = 11.1, 3.3 Hz, 1H), 3.29-3.21 (m, 2H), 1.78 (d, J = 5.1 Hz, 1H), 1.61 (d, J = 12.8 Hz, 1H), 1.54-1.38 (m, 3H), 1.18 (qd, J = 12.1, 3.7 Hz, 1H) 24 N-[(1,1- (ESI(+)) dioxidotetrahydro- m/e 428 thiophen-3- (M + H)+ yl)methyl]-4- [(imidazo[1,2- a]pyridin-6- ylcarbamoyl)ami- no]benzamide - The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-aminophenyl)-5,6-dihydropyridine-1 (2H)-carboxylate for 4-amino-N-isopentylbenzamide. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.96 (m, 1H), 8.82-8.75 (m, 1H), 8.65 (m, 1H), 7.96 (s, 1H), 7.52-7.36 (m, 6H), 7.12-7.04 (m, 1H), 6.12-6.05 (m, 1H), 4.07-3.92 (m, 2H), 3.59-3.49 (m, 2H), 2.44 (m, 2H), 1.43 (s, 9H); MS (ESI(+)) m/e 434 (M+H)+.
- A solution of tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (0.57 g, 1.315 mmol) in dichloromethane (5 ml) was treated with trifluoroacetic acid (0.608 ml, 7.88 mmol) and the reaction mixture was stirred at room temperature for 4 hours. Concentration provided the title compound.
- The title compound was prepared as described in Example 1A, substituting 1-(imidazo[1,2-a]pyridin-6-yl)-3-(4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)urea for 3-methylbutan-1-amine and 2-(tetrahydrofuran-3-yl)acetic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.96 (m, 1H), 8.82 (bs, 1H), 8.70 (bs, 1H), 7.96 (s, 1H), 7.55-7.35 (m, 6H), 7.08 (dd, J=9.6, 2.0 Hz, 1H), 6.11 (m, 1H), 4.18-4.05 (m, 2H), 3.90-3.79 (m, 1H), 3.76-3.57 (m, 4H), 3.35-3.23 (m, 2H), 2.55-2.39 (m, 4H), 2.05-1.95 (m, 1H), 1.60-1.42 (m, 1H); MS (ESI(+)) m/e 446 (M+H)+.
-
TABLE 3 The following Examples were prepared essentially as described in Example 28, substituting the appropriate carboxylic acid in Example 28B. Some products were purified by flash chromatography while others were purified by reverse-phase HPLC. Accordingly, some Examples were isolated as trifluoroacetic acid salts. Ex Name 1H NMR MS 29 1-{4-[1-(2-hydroxy- 1H NMR (300 MHz, DMSO-d6,) δ ppm 9.01- (ESI(+)) 2-methylpropanoyl)- 8.93 (m, 1H), 8.84 (bs, 1H), 8.71 (bs, 1H), m/e 420 1,2,3,6- 7.95 (s, 1H), 7.53-7.35 (m, 6H), 7.12-7.04 (M + H)+ tetrahydropyridin-4- (m, 1H), 6.13 (m, 1H), 5.43 (bs, 1H), 4.20- yl]phenyl}-3- 3.95 (m, 2H), 3.31 (m, 2H), 2.58-2.45 (m, imidazo[1,2- 2H), 1.34 (s, 6H) a]pyridin-6-ylurea 30 1-imidazo[1,2- 1H NMR (300 MHz, methanol-d4) δ ppm 9.01- (ESI(+)) a]pyridin-6-yl-3-{4- 8.81 (m, 1H), 7.82 (bs, 1H), 7.54-7.49 (m, m/e 461 [1-(morpholin-4- 2H), 7.48-7.32 (m, 4H), 7.18 (dd, J = 9.6, (M + H)+ ylacetyl)-1,2,3,6- 2.0 Hz, 1H), 6.09 (m, 1H), 4.31 (d, J = 2.8 Hz, tetrahydropyridin-4- 1H), 4.18 (d, J = 2.9 Hz, 1H), 3.89-3.76 (m, yl]phenyl}urea 2H), 3.71 (m, 4H), 3.38-3.25 (m, 2H), 2.65 (m, 1H), 2.61-2.49 (m, 5H) 31 1-{4-[1- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.85 (ESI(+)) (ethoxyacetyl)- (d, J = 1.9 Hz, 1H), 8.56 (s, 1H), 8.43 (s, 1H), m/e 420 1,2,3,6- 7.87 (s, 1H), 7.50-7.40 (m, 4H), 7.38-7.32 (M + H)+ tetrahydropyridin-4- (m, 2H), 7.10 (dd, J = 9.4, 2.0 Hz, 1H), 6.09- yl]phenyl}-3- 6.04 (m, 1H), 4.13 (s, 2H), 4.13-4.08 (m, imidazo[1,2- 2H), 3.66 (t, J = 5.7 Hz, 2H), 3.51 (q, J = 6.9 a]pyridin-6-ylurea Hz, 2H), 2.50-2.45 (m, 2H), 1.14 (t, J = 6.9 Hz, 3H) 32 1-imidazo[1,2- 1H NMR (300 MHz, DMSO-d6) δ ppm 8.96 (ESI(+)) a]pyridin-6-yl-3-(4- (d, J = 1.9 Hz, 1H), 8.83 (s, 1H), 8.70 (s, 1H), m/e 450 {1-[(2- 7.96 (s, 1H), 7.55-7.42 (m, 4H), 7.42-7.34 (M + H)+ methoxyethoxy)acetyl]- (m, 2H), 7.08 (dd, J = 9.6, 2.0 Hz, 1H), 6.15- 1,2,3,6- 6.05 (m, 1H), 4.24-4.17 (m, 2H), 4.12-4.05 tetrahydropyridin-4- (m, 2H), 3.70-3.54 (m, 4H), 3.51-3.43 (m, yl}phenyl)urea 2H), 3.25 (s, 3H), 2.57-2.41 (m, 2H) 33 1-imidazo[1,2- 1H NMR (400 MHz, DMSO-d6, Temp = 90° C.) (ESI(+)) a]pyridin-6-yl-3-{4- δ ppm 8.89-8.84 (m, 1H), 8.59 (s, 1H), 8.47 m/e 432 [1-(tetrahydrofuran- (s, 1H), 7.86 (s, 1H), 7.51-7.40 (m, 4H), (M + H)+ 2-ylcarbonyl)- 7.39-7.31 (m, 2H), 7.12-7.08 (m, 1H), 6.10- 1,2,3,6- 6.04 (m, 1H), 4.71-4.64 (m, 1H), 4.15 (m, tetrahydropyridin-4- 2H), 3.84-3.68 (m, 4H), 2.54-2.44 (m, 2H), yl]phenyl}urea 2.15-1.96 (m, 2H), 1.92-1.81 (m, 2H) 34 1-imidazo[1,2- 1H NMR (300 MHz, methanol-d4) δ ppm 8.93 (ESI(+)) a]pyridin-6-yl-3-{4- (dd, J = 2.0, 1.0 Hz, 1H), 7.82 (s, 1H), 7.56- m/e 446 [1-(tetrahydro-2H- 7.47 (m, 2H), 7.47-7.35 (m, 4H), 7.22-7.14 (M + H)+ pyran-4- (m, 1H), 6.13-6.07 (m, 1H), 4.32-4.16 (m, ylcarbonyl)-1,2,3,6- 2H), 4.03-3.92 (m, 2H), 3.86-3.77 (m, 2H), tetrahydropyridin-4- 3.61-3.46 (m, 2H), 3.12-2.92 (m, 1H), 2.66- yl]phenyl}urea 2.49 (m, 2H), 1.92-1.71 (m, 2H), 1.72- 1.59 (m, 2H) 35 1-{4-[1-(1,4-dioxan- 1H NMR (400 MHz, DMSO-d6, Temp = 90° C.) (ESI(+)) 2-ylcarbonyl)- δ ppm 8.86 (d, J = 1.2 Hz, 1H), 8.61 (bs, 1H), m/e 448 1,2,3,6- 8.49 (bs, 1H), 7.87 (s, 1H), 7.52-7.40 (m, (M + H)+ tetrahydropyridin-4- 4H), 7.38-7.32 (m, 2H), 7.11 (dd, J = 9.6, yl]phenyl}-3- 2.0 Hz, 1H), 6.10-6.04 (m, 1H), 4.37 (dd, J = imidazo[1,2- 9.2, 2.9 Hz, 1H), 4.15 (m, 2H), 3.81-3.63 a]pyridin-6-ylurea (m, 7H), 3.58-3.45 (m, 1H), 2.56-2.47 (m, 2H) 36 1-imidazo[1,2- 1H NMR (400 MHz, DMSO-d6, Temp = 90° C.) (ESI(+)) a]pyridin-6-yl-3-(4- δ ppm 8.91-8.87 (m 1H), 8.68 (s, 1H), 8.56 m/e 459 {1-[(1- (s, 1H), 7.90 (s, 1H), 7.53-7.44 (m, 4H), (M + H)+ methylpiperidin-4- 7.41-7.35 (m, 2H), 7.14 (dd, J = 9.6, 2.1 Hz, yl)carbonyl]- 1H), 6.14-6.08 (m, 1H), 4.19-4.13 (m, 2H), 1,2,3,6- 3.72 (t, J = 5.7 Hz, 2H), 3.17 (m, 1H), 2.85- tetrahydropyridin-4- 2.77 (m, 2H), 2.64-2.48 (m, 2H), 2.20 (s, yl}phenyl)urea 3H), 2.06-1.94 (m, 2H), 1.76-1.60 (m, 4H) 37 1-(4-{1-[(1,1- 1H NMR (300 MHz, DMSO-d6) δ 8.98-8.94 (ESI(+)) dioxidotetrahydro- (m, 1H), 8.83 (bs, 1H), 8.70 (s, 1H), 7.97- m/e 494 2H-thiopyran-4- 7.94 (m, 1H), 7.55-7.35 (m, 6H), 7.09 (dd, J = (M + H)+ yl)carbonyl]- 9.6, 2.0 Hz, 1H), 6.15-6.09 (m, 1H), 4.27- 1,2,3,6- 4.20 (m, 1H), 4.13-4.06 (m, 1H), 3.79- tetrahydropyridin-4- 3.62 (m, 2H), 3.28-3.02 (m, 5H), 2.40-2.60 yl}phenyl)-3- (m, 2H), 2.08-1.94 (m, 4H) imidazo[1,2- a]pyridin-6-ylurea 38 1-imidazo[1,2- 1H NMR (400 MHz, DMSO-d6, Temp = 90° C.) (ESI(+)) a]pyridin-6-yl-3-{4- δ ppm 8.88-8.83 (m, 1H), 8.59 (bs, 1H), m/e 404 [1-(2- 8.47 (bs, 1H), 7.87 (s, 1H), 7.50-7.41 (m, (M + H)+ methylpropanoyl)- 4H), 7.39-7.33 (m, 2H), 7.11 (dd, J = 9.5, 1,2,3,6- 2.0 Hz, 1H), 6.12-6.06 (m, 1H), 4.17-4.11 tetrahydropyridin-4- (m, 2H), 3.69 (t, J = 5.7 Hz, 2H), 2.95-2.86 yl]phenyl}urea (m, 1H), 2.50 (m, 2H), 1.05 (d, J = 6.7 Hz, 6H) - A suspension of 4-bromoaniline (406 mg, 2.362 mmol), 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (650 mg, 2.60 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (57.9 mg, 0.071 mmol) and sodium carbonate (526 mg, 4.96 mmol) in a 6:2:1 mixture of tetrahydrofuran/water/methanol (12 ml) in a microwave vial was subjected to three vacuum/nitrogen purge cycles. The vial was sealed and heated in an oil bath at 85° C. overnight. The mixture was dissolved in a mixture of ethyl acetate (45 ml) and water (20 ml), and the separated aqueous layer was extracted with ethyl acetate (20 ml). The combined organic layers were washed with brine (20 ml), dried with magnesium sulfate, filtered and concentrated. Normal phase chromatography provided the title compound.
- The title compound was prepared as described in Example 1C, substituting 4-(1-isobutyl-1H-pyrazol-4-yl)aniline for 4-amino-N-isopentylbenzamide. 1H NMR (400 MHz, CDCl3) δ 9.18 (s, 2H), 8.49 (s, 1H), 7.73 (s, 1H), 7.64 (d, J=10.3 Hz, 2H), 7.56 (s, 1H), 7.42-7.31 (m, 4H), 7.36 (d, J=9.5 Hz, 1H), 6.62 (dd, J=9.6, 1.7 Hz, 1H), 3.92 (d, J=7.3 Hz, 2H), 2.23 (hept, J=6.8 Hz, 1H), 0.93 (d, J=6.7 Hz, 6H). MS (ESI)(+)) m/e 375 (M+H)+.
- A solution of methyl 4-aminobenzoate (0.25 g, 1.654 mmol) in tetrahydrofuran (8.27 ml) was treated with diisopropylethylamine (0.433 ml, 2.481 mmol) and 2-cyclopentylacetyl chloride (0.279 g, 1.902 mmol) and the reaction mixture was stirred at ambient temperature for 2 hours. Concentration and normal phase chromatography provided the title compound.
- The title compound was prepared as described in Example 4B, substituting methyl 4-(2-cyclopentylacetamido)benzoate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.08 (s, 1H), 8.93 (t, J=5.8 Hz, 1H), 8.47 (s, 1H), 7.96 (s, 1H), 7.87-7.81 (m, 2H), 7.70-7.64 (m, 2H), 7.57-7.50 (m, 2H), 7.24 (dd, J=9.2, 1.7 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 2.36-2.30 (m, 2H), 2.29-2.15 (m, 1H), 1.81-1.65 (m, 2H), 1.67-1.38 (m, 4H), 1.39-0.95 (m, 2H); MS (ESI(+)) m/e 377 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-A]pyridin-6-amine (0.768 g, 5.77 mmol) for 3-methylbutan-1-amine and 2-bromo-5-thiazolecarboxylic acid (1 g, 4.81 mmol) for 4-nitrobenzoic acid.
- To a solution of 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide (165 mg, 0.511 mmol) in acetonitrile (2553 μl) was added 4-cyanobenzylamine (67.5 mg, 0.511 mmol). The mixture was heated in a microwave (Biotage Initiator) at 180° C. for 30 minutes. The heating was repeated again after another equivalent of 4-cyanobenzylamine was added. The reaction mixture was purified by normal phase chromatography to provide the title compound.
- The title compound was prepared as described in Example 52A, substituting 3-methylbutanoyl chloride for 2-cyclopentylacetyl chloride and 2-(4-cyanobenzylamino)-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ 10.75 (s, 1H), 9.62 (s, 1H), 8.43 (d, J=1.6 Hz, 1H), 8.32 (s, 1H), 8.11 (s, 1H), 7.99-7.89 (m, 2H), 7.82 (dd, J=18.8, 8.3 Hz, 2H), 7.38 (d, J=8.3 Hz, 2H), 5.63 (s, 2H), 2.14 (dt, J=13.4, 6.7 Hz, 1H), 0.88 (d, J=6.7 Hz, 6H); (APCI(+)) m/e 459 (M+H)+.
-
TABLE 4 The following Examples were prepared essentially as described in Example 53, substituting the appropriate amine in Example 53A, the appropriate amine in 53B and the appropriate acid chloride in Example 53C. Some products were purified by flash chromatography while others were purified by reverse-phase HPLC. Accordingly, some Examples were isolated as trifluoroacetic acid salts. Ex Name 1H NMR MS 54 2-[(4- 1H NMR (400 MHz, DMSO-d6) δ 10.75 (s, (APCI(+)) cyanobenzyl)(3- 1H), 9.61 (s, 1H), 8.42 (s, 1H), 8.33 (s, 1H), m/e 461 methoxypropanoyl) 8.10 (s, 1H), 7.94 (s, 2H), 7.84 (d, J = 8.3 (M + H)+ amino]-N- Hz, 3H), 7.40 (d, J = 8.3 Hz, 2H), 5.64 (s, (imidazo[1,2- 2H), 3.64 (t, J = 6.0 Hz, 2H), 3.20 (s, 3H), a]pyridin-6-yl)-1,3- 2.89 (t, J = 6.1 Hz, 2H). thiazole-5- carboxamide 55 2-[(4- 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), (APCI(+)) cyanobenzyl)(3- 8.16 (d, J = 9.5 Hz, 1H), 7.96 (s, 1H), 7.86 m/e 473 methylbutanoyl)ami- (d, J = 1.8 Hz, 1H), 7.81 (d, J = 9.6 Hz, (M + H)+ no]-N-(imidazo[1,2- 1H), 7.75 (s, 1H), 7.63 (d, J = 8.3 Hz, 2H), a]pyridin-6- 7.24 (d, J = 8.3 Hz, 2H), 5.54 (s, 2H), 4.69 ylmethyl)-1,3- (d, J = 6.1 Hz, 2H), 2.39 (d, J = 6.7 Hz, thiazole-5- 2H), 2.30-2.24 (m, 1H), 0.94 (d, J = 6.6 carboxamide Hz, 6H) 56 2-[(4- 1H NMR (400 MHz, methanol-d4) δ 8.78 (s, (APCI(+)) cyanobenzyl)(3- 1H), 8.20 (d, J = 2.1 Hz, 1H), 8.02 (d, J = m/e 475 methoxypropanoyl) 2.1 Hz, 1H), 8.01 (s, 1H), 8.00-7.96 (m, (M + H)+ amino]-N- 1H), 7.90 (d, J = 9.3 Hz, 1H), 7.70 (d, J = (imidazo[1,2- 8.2 Hz, 2H), 7.38 (d, J = 8.2 Hz, 2H), 5.65 a]pyridin-6- (s, 2H), 4.66 (s, 2H), 3.73 (t, J = 5.9 Hz, ylmethyl)-1,3- 2H), 2.87 (t, J = 5.9 Hz, 2H) thiazole-5- carboxamide 57 2-[(4- 1H NMR (400 MHz, methanol-d4) δ 9.22 (APCI(+)) cyanobenzyl)(3- (td, J = 6.4, 1.2 Hz, 1H), 8.75 (d, J = 7.0 m/e 475 methoxypropanoyl) Hz, 1H), 8.18 (d, J = 2.0 Hz, 1H), 8.08- (M + H)+ amino]-N- 7.95 (m, 2H), 7.80 (s, 1H), 7.77-7.66 (m, (imidazo[1,2- 2H), 7.47 (dd, J = 7.1, 1.1 Hz, 1H), 7.39 (d, a]pyridin-7- J = 8.2 Hz, 2H), 5.66 (s, 2H), 4.73 (d, J = ylmethyl)-1,3- 4.5 Hz, 2H), 3.74 (t, J = 5.9 Hz, 2H), 2.88 thiazole-5- (t, J = 5.8 Hz, 2H) carboxamide 61 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ 8.79 (s, (APCI(+)) a]pyridin-6- 1H), 8.22 (d, J = 2.1 Hz, 1H), 8.08 (s, 1H), m/e 430 ylmethyl)-2-[(3- 8.05-7.96 (m, 2H), 7.90 (d, J = 9.3 Hz, (M + H)+ methoxypropanoyl)(3- 1H), 4.67 (d, J = 3.8 Hz, 2H), 4.27 (dd, J = methylbutyl)amino]- 9.3, 7.0 Hz, 2H), 3.79 (t, J = 5.9 Hz, 2H), 1,3-thiazole-5- 3.36 (s, 3H), 2.98 (t, J = 5.9 Hz, 2H), 1.80- carboxamide 1.67 (m, 1H), 1.67-1.57 (m, 2H), 1.01 (d, J = 6.5 Hz, 6H) 121 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ 9.11 (t, J = (APCI(+)) a]pyridin-7- 5.9 Hz, 1H), 8.50 (d, J = 7.0 Hz, 1H), m/e 444 ylmethyl)-2-[(3- 8.17 (s, 1H), 7.90 (s, 1H), 7.53 (s, 1H), 7.41 (M + H)+ methoxypropanoyl)(tet- (s, 1H), 6.85 (dd, J = 7.1, 1.5 Hz, 1H), 4.48 rahydrofuran-2- (d, J = 5.8 Hz, 2H), 4.39 (d, J = 12.5 Hz, ylmethyl)amino]- 1H), 4.25-4.08 (m, 2H), 3.78 (dd, J = 14.8, 1,3-thiazole-5- 6.8 Hz, 1H), 3.66 (t, J = 6.4 Hz, 2H), 3.65- carboxamide 3.55 (m, 1H), 3.26 (s, 3H), 3.06 (ddd, J = 17.2, 13.9, 6.4 Hz, 2H), 1.99 (dd, J = 12.7, 7.4 Hz, 1H), 1.94-1.86 (m, 1H), 1.86- 1.74 (m, 1H), 1.66-1.53 (m, 1H) 123 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6/D2O) δ ppm (ESI(+)) a]pyridin-6- 8.76 (s, 1 H) 8.24 (d, J = 2.14 Hz, 1 H) 8.10 m/e 496 ylmethyl)-2-{[(2- (s, 1 H) 8.02 (d, J = 2.14 Hz, 1 H) 7.89 (d, (M + H)+ methyl-1,3-thiazol-5- J = 1.22 Hz, 2 H) 7.45 (s, 1 H) 4.57 (s, 2 H) yl)acetyl](tetrahydro- 4.50 (d, J = 12.21 Hz, 1 H) 4.42 (d, J = 5.80 furan-2- Hz, 1 H) 4.19-4.31 (m, 2 H) 3.78-3.85 ylmethyl)amino}- (m, 1 H) 3.63-3.69 (m, 1 H) 3.28-3.29 1,3-thiazole-5- (m, 2 H) 2.62 (s, 3 H) 2.01 (s, 1 H) 1.81- carboxamide 1.95 (m, 2 H) 1.60-1.68 (m, 1 H) 124 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6/D2O) δ ppm (ESI(+)) a]pyridin-6- 8.78 (s, 1 H) 8.26 (d, J = 1.83 Hz, 1 H) 8.10 m/e 496 ylmethyl)-2-{[(2- (s, 1 H) 8.05 (d, J = 2.14 Hz, 1 H) 7.90-7.96 (M + H)+ methyl-1,3-thiazol-4- (m, 2 H) 7.24 (s, 1 H) 4.58 (s, 2 H) 4.47 (dd, yl)acetyl](tetrahydro- 1 H) 4.18-4.37 (m, 4 H) 3.79-3.86 (m, 1 furan-2- H) 3.62-3.69 (m, 1 H) 2.62 (s, 3 H) 1.97- ylmethyl)amino}- 2.06 (m, 1 H) 1.80-1.94 (m, 2 H) 1.56- 1,3-thiazole-5- 1.69 (m, 1H) carboxamide 125 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6/D2O) δ ppm (ESI(+)) a]pyridin-6- 8.70 (s, 1 H) 8.17 (d, J = 1.83 Hz, 1 H) 8.10 m/e 480 ylmethyl)-2-{[(3- (s, 1 H) 7.92 (d, J = 1.83 Hz, 1 H) 7.79-7.84 (M + H)+ methyl-1,2-oxazol-5- (m, 1 H) 7.73-7.85 (m, 1 H) 6.27 (s, 1 H) yl)acetyl](tetrahydro- 4.55 (s, 2 H) 4.35-4.52 (m, 3 H) 4.19- furan-2- 4.27 (m, 2 H) 3.77-3.85 (m, 1 H) 3.62- ylmethyl)amino}- 3.69 (m, 1 H) 2.23 (s, 3 H) 2.01 (d, J = 2.75 1,3-thiazole-5- Hz, 1 H) 1.80-1.95 (m, 2 H) 1.56-1.67 carboxamide (m, 1 H) 126 2-{[3-(3-chloro-1,2- (ESI(+)) oxazol-5- m/e 515 yl)propanoyl](tetra- (M + H)+ hydrofuran-2- ylmethyl)amino}-N- (imidazo[1,2- a]pyridin-6- ylmethyl)-1,3- thiazole-5- carboxamide 127 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 510 ylmethyl)-2-{[3-(3- (M + H)+ methoxy-1,2- oxazol-5- yl)propanoyl](tetra- hydrofuran-2- ylmethyl)amino}- 1,3-thiazole-5- carboxamide 128 2-{[(3,5-dimethyl- (ESI(+)) 1,2-oxazol-4- m/e 495 yl)acetyl](tetrahydro- (M + H)+ furan-2- ylmethyl)amino}-N- (imidazo[1,2- a]pyridin-6- ylmethyl)-1,3- thiazole-5- carboxamide 129 2-{[3-(3,5-dimethyl- (ESI(+)) 1,2-oxazol-4- m/e 509 yl)propanoyl](tetra- (M + H)+ hydrofuran-2- ylmethyl)amino}-N- (imidazo[1,2- a]pyridin-6- ylmethyl)-1,3- thiazole-5- carboxamide 130 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 494 ylmethyl)-2-{[3-(1- (M + H)+ methyl-1H-pyrazol-4- yl)propanoyl](tetra- hydrofuran-2- ylmethyl)amino}- 1,3-thiazole-5- carboxamide 131 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 511 ylmethyl)-2-{[3-(4- (M + H)+ methyl-1,3-thiazol-5- yl)propanoyl](tetra- hydrofuran-2- ylmethyl)amino}- 1,3-thiazole-5- carboxamide 132 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 468 ylmethyl)-2- (M + H)+ [(tetrahydrofuran-2- ylmethyl)(1H- tetrazol-5- ylacetyl)amino]-1,3- thiazole-5- carboxamide 133 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 481 ylmethyl)-2-{[3- (M + H)+ (1,2-oxazol-5- yl)propanoyl](tetra- hydrofuran-2- ylmethyl)amino}- 1,3-thiazole-5- carboxamide 134 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 467 ylmethyl)-2-[(1,2- (M + H)+ oxazol-3- ylacetyl)(tetrahydro- furan-2- ylmethyl)amino]- 1,3-thiazole-5- carboxamide 135 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 481 ylmethyl)-2-{[3- (M + H)+ (1,2-oxazol-4- yl)propanoyl](tetra- hydrofuran-2- ylmethyl)amino}- 1,3-thiazole-5- carboxamide 136 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 497 ylmethyl)-2- (M + H)+ {(tetrahydrofuran-2- ylmethyl)[3-(1,3- thiazol-2- yl)propanoyl]amino}- 1,3-thiazole-5- carboxamide 139 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ 8.79 (s, (APCI(+)) a]pyridin-6- 1H), 8.22 (d, J = 2.1 Hz, 1H), 8.08 (s, 1H), m/e 444 ylmethyl)-2-[(3- 8.03 (d, J = 2.2 Hz, 1H), 7.98 (d, J = 1.4 Hz, (M + H)+ methoxypropanoyl)(tet- 1H), 7.91 (d, J = 9.3 Hz, 1H), 4.66 (s, 2H), rahydrofuran-3- 4.31 (qd, J = 14.8, 7.7 Hz, 2H), 3.96 (td, J = ylmethyl)amino]- 8.2, 5.7 Hz, 1H), 3.87-3.71 (m, 3H), 3.65 1,3-thiazole-5- (qd, J = 8.9, 5.6 Hz, 2H), 3.36 (s, 3H), 3.02 carboxamide (dd, J = 10.4, 5.6 Hz, 2H), 2.94-2.81 (m, 1H), 2.05 (dtd, J = 13.5, 8.0, 5.7 Hz, 1H), 1.75 (ddd, J = 12.6, 7.9, 6.5 Hz, 1H) 140 N-(imidazo[1,2- 1H NMR (500 MHz, methanol-d4) δ 8.79 (s, (APCI(+)) a]pyridin-6- 1H), 8.21 (d, J = 1.9 Hz, 1H), 8.09 (s, 1H), m/e 470 ylmethyl)-2- 8.03 (d, J = 2.0 Hz, 1H), 8.00 (d, J = 9.3 Hz, (M + H)+ [(tetrahydrofuran-3- 1H), 7.91 (d, J = 9.2 Hz, 1H), 4.66 (s, 2H), ylmethyl)(tetrahydro- 4.40 (dd, J = 14.8, 7.0 Hz, 1H), 4.28 (dd, J = 2H-pyran-4- 14.7, 8.5 Hz, 1H), 4.06-3.94 (m, 3H), ylcarbonyl)amino]- 3.77 (dd, J = 15.0, 8.1 Hz, 1H), 3.68 (dd, J = 1,3-thiazole-5- 8.9, 6.3 Hz, 1H), 3.60 (dd, J = 8.9, 4.7 Hz, carboxamide 1H), 3.55 (t, J = 11.7 Hz, 2H), 3.24 (tt, J = 11.1, 3.7 Hz, 1H), 2.85 (dt, J = 12.1, 3.5 Hz, 1H), 2.11-2.01 (m, 1H), 1.93 (ddd, J = 16.1, 12.7, 4.3 Hz, 1H), 1.89-1.82 (m, 1H), 1.75 (dt, J = 13.0, 9.9 Hz, 3H) 142 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ 8.79 (s, (APCI(+)) a]pyridin-6- 1H), 8.22 (d, J = 2.1 Hz, 1H), 8.08 (s, 1H), m/e 458 ylmethyl)-2-[(3- 8.03 (d, J = 2.1 Hz, 1H), 8.00 (dd, J = 9.4, (M + H)+ methoxypropanoyl)(tet- 1.4 Hz, 1H), 7.91 (d, J = 9.4 Hz, 1H), 4.66 rahydro-2H- (s, 2H), 4.23 (d, J = 7.3 Hz, 2H), 4.00- pyran-4- 3.85 (m, 2H), 3.79 (t, J = 5.9 Hz, 2H), 3.36 ylmethyl)amino]- (s, 3H), 3.02 (t, J = 5.9 Hz, 2H), 2.26-2.13 1,3-thiazole-5- (m, 1H), 1.58-1.50 (m, 2H), 1.49-1.36 carboxamide (m, 2H) 143 N-(imidazo[1,2- 1H NMR (500 MHz, methanol-d4) δ 8.79 (s, (APCI(+)) a]pyridin-6- 1H), 8.21 (d, J = 2.1 Hz, 1H), 8.09 (s, 1H), m/e 470 ylmethyl)-2- 8.03 (d, J = 2.0 Hz, 1H), 8.00 (d, J = 9.3 Hz, (M + H)+ [(tetrahydrofuran-3- 1H), 7.91 (d, J = 9.3 Hz, 1H), 4.67 (s, 2H), ylcarbonyl)(tetra- 4.32-4.23 (m, 2H), 4.08 (t, J = 8.1 Hz, hydro-2H-pyran-4- 1H), 3.94 (qd, J = 9.9, 3.8 Hz, 4H), 3.87 ylmethyl)amino]- (dd, J = 14.8, 7.3 Hz, 1H), 3.83-3.74 (m, 1,3-thiazole-5- 1H), 3.35 (dd, J = 11.7, 1.9 Hz, 2H), 2.31 carboxamide (dt, J = 15.4, 7.1 Hz, 1H), 2.18 (td, J = 12.9, 6.6 Hz, 2H), 1.53 (t, J = 10.9 Hz, 2H), 1.50- 1.41 (m, 2H) 144 N-(imidazo[1,2- 1H NMR (500 MHz, methanol-d4) δ 8.79 (s, (APCI(+)) a]pyridin-6- 1H), 8.21 (d, J = 2.0 Hz, 1H), 8.09 (s, 1H), m/e 484 ylmethyl)-2- 8.03 (d, J = 2.1 Hz, 1H), 8.00 (dd, J = 9.3, (M + H)+ [(tetrahydro-2H- 1.4 Hz, 1H), 7.91 (d, J = 9.3 Hz, 1H), 4.66 pyran-4- (s, 2H), 4.27 (d, J = 7.3 Hz, 2H), 4.03- ylcarbonyl)(tetra- 3.97 (m, 2H), 3.93 (dd, J = 11.4, 2.7 Hz, hydro-2H-pyran-4- 2H), 3.62-3.52 (m, 2H), 3.35 (dd, J = 11.6, ylmethyl)amino]- 2.2 Hz, 2H), 3.26 (dd, J = 9.3, 5.6 Hz, 1H), 1,3-thiazole-5- 2.21-2.10 (m, 1H), 1.89 (ddd, J = 16.0, carboxamide 12.6, 4.4 Hz, 2H), 1.76 (dd, J = 13.0, 1.5 Hz, 2H), 1.54 (dt, J = 7.1, 3.0 Hz, 2H), 1.51- 1.42 (m, 2H) 145 N-(imidazo[1,2- 1H NMR (500 MHz, methanol-d4) δ 8.78 (s, (APCI(+)) a]pyridin-6- 1H), 8.21 (s, 1H), 8.07 (s, 1H), 8.02 (s, 1H), m/e 444 ylmethyl)-2-{(3- 8.00 (d, J = 9.4 Hz, 1H), 7.91 (d, J = 9.4 Hz, (M + H)+ methoxy- 1H), 4.66 (s, 2H), 4.52 (d, J = 14.9 Hz, 1H), propanoyl)[(2R)- 4.29 (d, J = 6.8 Hz, 1H), 4.17 (dd, J = 14.9, tetrahydrofuran-2- 8.9 Hz, 1H), 3.88 (dd, J = 14.5, 7.2 Hz, 1H), ylmethyl]amino}- 3.76 (dd, J = 14.0, 7.9 Hz, 2H), 3.74-3.69 1,3-thiazole-5- (m, 1H), 3.36 (s, 3H), 3.13 (q, J = 6.1 Hz, carboxamide 2H), 2.10 (td, J = 12.4, 7.4 Hz, 1H), 2.04- 1.94 (m, 1H), 1.94-1.85 (m, 1H), 1.67 (dq, J = 15.3, 7.8 Hz, 1H) 146 N-(imidazo[1,2- 1H NMR (500 MHz, methanol-d4) δ 8.79 (s, (APCI(+)) a]pyridin-6- 1H), 8.21 (s, 1H), 8.08 (s, 1H), 8.02 (d, J = m/e 456 ylmethyl)-2- 1.8 Hz, 1H), 8.00 (d, J = 9.4 Hz, 1H), 7.91 (M + H)+ {(tetrahydrofuran-3- (d, J = 9.3 Hz, 1H), 4.66 (s, 2H), 4.61 (t, J = ylcarbonyl)[(2R)- 13.7 Hz, 1H), 4.30-4.17 (m, 2H), 4.06 tetrahydrofuran-2- (ddd, J = 15.8, 14.9, 7.9 Hz, 1H), 3.99- ylmethyl]amino}- 3.91 (m, 2H), 3.90-3.79 (m, 3H), 3.76- 1,3-thiazole-5- 3.68 (m, 1H), 2.32 (qd, J = 12.8, 6.7 Hz, carboxamide 1H), 2.25-2.04 (m, 2H), 2.03-1.86 (m, 2H), 1.72-1.61 (m, 1H) 147 N-(imidazo[1,2- 1H NMR (500 MHz, methanol-d4) δ 8.79 (s, (APCI(+)) a]pyridin-6- 1H), 8.21 (d, J = 2.1 Hz, 1H), 8.07 (s, 1H), m/e 470 ylmethyl)-2-{[(2R)- 8.02 (d, J = 2.1 Hz, 1H), 8.00 (dd, J = 9.3, (M + H)+ tetrahydrofuran-2- 1.2 Hz, 1H), 7.91 (d, J = 9.3 Hz, 1H), 4.66 ylmethyl](tetrahydro- (s, 2H), 4.61 (d, J = 12.8 Hz, 1H), 4.29- 2H-pyran-4- 4.19 (m, 2H), 4.06-3.96 (m, 2H), 3.85 (dd, ylcarbonyl)amino}- J = 14.9, 6.9 Hz, 1H), 3.73 (dd, J = 13.9, 7.7 1,3-thiazole-5- Hz, 1H), 3.57-3.47 (m, 2H), 3.43 (ddd, J = carboxamide 14.8, 8.4, 3.9 Hz, 1H), 2.11 (dt, J = 12.1, 5.4 Hz, 1H), 2.05-1.87 (m, 3H), 1.83- 1.73 (m, 3H), 1.73-1.64 (m, 1H) 148 N-(imidazo[1,2- 1H NMR (500 MHz, methanol-d4) δ 8.78 (s, (APCI(+)) a]pyridin-6- 1H), 8.21 (d, J = 1.8 Hz, 1H), 8.06 (s, 1H), m/e 444 ylmethyl)-2-{(3- 8.02 (d, J = 2.2 Hz, 1H), 8.00 (dd, J = 9.4, (M + H)+ methoxypropanoyl)[(2S)- 1.5 Hz, 1H), 7.90 (d, J = 9.3 Hz, 1H), 4.66 tetrahydrofuran-2- (s, 2H), 4.52 (dd, J = 14.9, 2.5 Hz, 1H), ylmethyl]amino}- 4.32-4.25 (m, 1H), 4.17 (dd, J = 14.8, 8.9 1,3-thiazole-5- Hz, 1H), 3.92-3.83 (m, 1H), 3.81-3.74 carboxamide (m, 2H), 3.71 (td, J = 7.7, 6.3 Hz, 1H), 3.36 (s, 3H), 3.21-3.05 (m, 2H), 2.15-2.05 (m, 1H), 2.04-1.95 (m, 1H), 1.91 (ddt, J = 7.5, 5.0, 1.9 Hz, 1H), 1.73-1.60 (m, 1H) 149 N-(imidazo[1,2- 1H NMR (500 MHz, methanol-d4) δ 8.79 (s, (APCI(+)) a]pyridin-6- 1H), 8.21 (d, J = 2.2 Hz, 1H), 8.08 (d, J = m/e 456 ylmethyl)-2- 0.7 Hz, 1H), 8.02 (d, J = 2.1 Hz, 1H), 8.00 (M + H)+ {(tetrahydrofuran-3- (dd, J = 9.3, 1.3 Hz, 1H), 7.91 (d, J = 9.3 ylcarbonyl)[(2S)- Hz, 1H), 4.66 (s, 2H), 4.61 (t, J = 13.2 Hz, tetrahydrofuran-2- 1H), 4.31-4.17 (m, 2H), 4.06 (ddd, J = ylmethyl]amino}- 14.8, 14.3, 7.3 Hz, 1H), 4.00-3.92 (m, 1,3-thiazole-5- 2H), 3.90-3.79 (m, 3H), 3.71 (ddd, J = carboxamide 10.8, 8.3, 3.1 Hz, 1H), 2.39-2.27 (m, 1H), 2.25-2.04 (m, 2H), 2.03-1.87 (m, 2H), 1.73-1.60 (m, 1H) 150 N-(imidazo[1,2- 1H NMR (500 MHz, methanol-d4) δ 8.79 (s, (APCI(+)) a]pyridin-6- 1H), 8.21 (d, J = 1.9 Hz, 1H), 8.07 (d, J = m/e 470 ylmethyl)-2-{[(2S)- 3.1 Hz, 1H), 8.02 (d, J = 2.2 Hz, 1H), 8.00 (M + H)+ tetrahydrofuran-2- (dd, J = 9.4, 1.5 Hz, 1H), 7.91 (d, J = 9.3 ylmethyl](tetrahydro- Hz, 1H), 4.66 (s, 2H), 4.61 (d, J = 12.7 Hz, 2H-pyran-4- 1H), 4.31-4.19 (m, 2H), 4.07-3.95 (m, ylcarbonyl)amino}- 2H), 3.89-3.81 (m, 1H), 3.73 (td, J = 7.8, 1,3-thiazole-5- 6.1 Hz, 1H), 3.58-3.47 (m, 2H), 3.47- carboxamide 3.39 (m, 1H), 2.16-2.05 (m, 1H), 2.05- 1.86 (m, 3H), 1.77 (ddd, J = 14.6, 6.0, 2.5 Hz, 3H), 1.73-1.65 (m, 1H) 183 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 480 ylmethyl)-2-{[(1- (M + H)+ methyl-1H-pyrazol-4- yl)acetyl](tetrahydro- furan-2- ylmethyl)amino}- 1,3-thiazole-5- carboxamide 184 2-{[(1,3-dimethyl- (ESI(+)) 1H-pyrazol-4- m/e 494 yl)acetyl](tetrahydro- (M + H)+ furan-2- ylmethyl)amino}-N- (imidazo[1,2- a]pyridin-6- ylmethyl)-1,3- thiazole-5- carboxamide 189 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 493 ylmethyl)-2-{[3-(1- (M + H)+ methyl-1H-pyrrol-2- yl)propanoyl](tetra- hydrofuran-2- ylmethyl)amino}- 1,3-thiazole-5- carboxamide 190 2-{[(1,5-dimethyl- (ESI(+)) 1H-pyrazol-3- m/e 494 yl)acetyl](tetrahydro- (M + H)+ furan-2- ylmethyl)amino}-N- (imidazo[1,2- a]pyridin-6- ylmethyl)-1,3- thiazole-5- carboxamide 191 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 483 ylmethyl)-2- (M + H)+ [(tetrahydrofuran-2- ylmethyl)(1,3- thiazol-4- ylacetyl)amino]-1,3- thiazole-5- carboxamide 192 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ 8.73 (d, (APCI(+)) a]pyridin-7- J = 7.0 Hz, 1H), 8.64 (d, J = 1.5 Hz, 1H), m/e 467 ylmethyl)-2-{(1,2- 8.16 (d, J = 2.1 Hz, 1H), 8.12 (s, 1H), 7.98 (M + H)+ oxazol-3- (d, J = 2.2 Hz, 1H), 7.80 (s, 1H), 7.46 (dd, J = ylacetyl)[(2R)- 7.0, 1.4 Hz, 1H), 6.52 (d, J = 1.6 Hz, 1H), tetrahydrofuran-2- 4.72 (s, 2H), 4.65 (dd, J = 14.9, 1.9 Hz, ylmethyl]amino}- 1H), 4.42 (d, J = 1.4 Hz, 2H), 4.32 (dd, J = 1,3-thiazole-5- 11.6, 4.4 Hz, 1H), 4.23 (dd, J = 14.8, 9.0 carboxamide Hz, 1H), 3.94 (dd, J = 14.9, 6.8 Hz, 1H), 3.76 (dd, J = 14.2, 7.7 Hz, 1H), 2.21-2.07 (m, 1H), 2.08-1.87 (m, 2H), 1.69 (ddd, J = 15.8, 12.3, 7.6 Hz, 1H) 193 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ 8.74 (d, (APCI(+)) a]pyridin-7- J = 7.0 Hz, 1H), 8.17 (d, J = 1.9 Hz, 1H), m/e 481 ylmethyl)-2-{[(5- 8.11 (s, 1H), 7.99 (d, J = 2.1 Hz, 1H), 7.79 (M + H)+ methyl-1,2-oxazol- (s, 1H), 7.47 (d, J = 6.8 Hz, 1H), 6.16 (s, 3-yl)acetyl][(2R)- 1H), 4.72 (s, 2H), 4.63 (d, J = 12.8 Hz, 1H), tetrahydrofuran-2- 4.36-4.27 (m, 3H), 4.21 (dd, J = 14.6, 9.4 ylmethyl]amino}- Hz, 1H), 3.94 (dd, J = 15.1, 6.8 Hz, 1H), 1,3-thiazole-5- 3.75 (dd, J = 14.3, 7.5 Hz, 1H), 2.43 (s, carboxamide 3H), 2.13 (d, J = 8.1 Hz, 1H), 2.05-1.89 (m, 2H), 1.75-1.62 (m, 1H) 194 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ 8.74 (d, (APCI(+)) a]pyridin-7- J = 7.0 Hz, 1H), 8.27 (d, J = 1.6 Hz, 1H), m/e 481 ylmethyl)-2-{[3- 8.17 (d, J = 2.1 Hz, 1H), 8.10 (s, 1H), 7.99 (M + H)+ (1,2-oxazol-5- (d, J = 2.1 Hz, 1H), 7.79 (s, 1H), 7.47 (d, J = yl)propanoyl][(2R)- 6.8 Hz, 1H), 6.23 (s, 1H), 4.72 (s, 2H), tetrahydrofuran-2- 4.55 (d, J = 12.6 Hz, 1H), 4.35-4.23 (m, ylmethyl]amino}- 1H), 4.15 (dd, J = 14.8, 9.0 Hz, 1H), 3.87 1,3-thiazole-5- (dd, J = 14.8, 6.9 Hz, 1H), 3.72 (dd, J = carboxamide 14.0, 7.8 Hz, 1H), 3.46 (dd, J = 12.2, 6.1 Hz, 1H), 3.28-3.18 (m, 3H), 2.10 (dd, J = 12.6, 7.2 Hz, 1H), 1.94 (dd, J = 15.7, 8.4 Hz, 2H), 1.74-1.60 (m, 1H) 195 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ 8.71 (d, (APCI(+)) a]pyridin-7- J = 7.0 Hz, 1H), 8.51 (s, 1H), 8.36 (s, 1H), m/e 481 ylmethyl)-2-{[3- 8.11 (d, J = 17.0 Hz, 2H), 7.94 (d, J = 2.0 (M + H)+ (1,2-oxazol-4- Hz, 1H), 7.76 (s, 1H), 7.42 (d, J = 6.8 Hz, yl)propanoyl][(2R)- 1H), 4.71 (s, 2H), 4.53 (d, J = 12.5 Hz, 1H), tetrahydrofuran-2- 4.27 (t, J = 6.7 Hz, 1H), 4.14 (dd, J = 14.9, ylmethyl]amino}- 9.1 Hz, 1H), 3.83 (dd, J = 14.9, 6.8 Hz, 1H), 1,3-thiazole-5- 3.69 (dd, J = 13.8, 7.5 Hz, 1H), 3.26 (d, J = carboxamide 7.1 Hz, 1H), 3.09 (dd, J = 17.6, 6.4 Hz, 1H), 2.91 (dd, J = 12.3, 6.4 Hz, 2H), 2.10 (dt, J = 12.3, 5.9 Hz, 1H), 2.03-1.84 (m, 2H), 1.74- 1.58 (m, 1H) 196 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ 9.00 (s, (APCI(+)) a]pyridin-7- 1H), 8.74 (d, J = 7.0 Hz, 1H), 8.17 (d, J = m/e 483 ylmethyl)-2-{[(2R)- 1.9 Hz, 1H), 8.11 (s, 1H), 7.98 (d, J = 2.2 (M + H)+ tetrahydrofuran-2- Hz, 1H), 7.79 (s, 1H), 7.51 (s, 1H), 7.47 (d, ylmethyl](1,3- J = 7.0 Hz, 1H), 4.72 (s, 2H), 4.63 (d, J = thiazol-4- 12.8 Hz, 1H), 4.49 (q, J = 16.9 Hz, 2H), ylacetyl)amino}- 4.38-4.25 (m, 2H), 3.96 (dd, J = 14.9, 6.7 1,3-thiazole-5- Hz, 1H), 3.76 (dd, J = 14.2, 7.6 Hz, 1H), carboxamide 2.19-2.08 (m, 1H), 2.06-1.98 (m, 1H), 1.98-1.89 (m, 1H), 1.70 (td, J = 15.6, 7.6 Hz, 1H) 197 2-{[(1,5-dimethyl- 1H NMR (400 MHz, methanol-d4) δ 8.74 (d, (APCI(+)) 1H-pyrazol-3- J = 7.0 Hz, 1H), 8.17 (d, J = 2.1 Hz, 1H), m/e 494 yl)acetyl][(2R)- 8.10 (s, 1H), 7.99 (d, J = 2.1 Hz, 1H), 7.79 (M + H)+ tetrahydrofuran-2- (s, 1H), 7.47 (d, J = 7.0 Hz, 1H), 6.01 (s, ylmethyl]amino}-N- 1H), 4.72 (s, 2H), 4.55 (d, J = 12.9 Hz, 1H), (imidazo[1,2- 4.30 (t, J = 7.9 Hz, 1H), 4.27-4.18 (m, a]pyridin-7- 2H), 4.10 (t, J = 15.1 Hz, 1H), 3.94 (dd, J = ylmethyl)-1,3- 14.8, 6.8 Hz, 1H), 3.82-3.68 (m, 4H), 2.27 thiazole-5- (s, 3H), 2.20-2.06 (m, 1H), 2.00 (dd, J = carboxamide 13.5, 5.8 Hz, 1H), 1.97-1.87 (m, 1H), 1.76- 1.58 (m, 1H) 198 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ 8.75 (d, (APCI(+)) a]pyridin-7- J = 7.0 Hz, 1H), 8.17 (d, J = 2.1 Hz, 1H), m/e 494 ylmethyl)-2-{[3-(1- 8.09 (s, 1H), 7.99 (d, J = 2.1 Hz, 1H), 7.80 (M + H)+ methyl-1H-pyrazol-4- (s, 1H), 7.47 (d, J = 8.2 Hz, 1H), 7.45 (s, yl)propanoyl][(2R)- 1H), 7.36 (s, 1H), 4.72 (s, 2H), 4.50 (dd, J = tetrahydrofuran-2- 14.9, 2.3 Hz, 1H), 4.27 (t, J = 6.9 Hz, 1H), ylmethyl]amino}- 4.13 (dd, J = 14.9, 9.0 Hz, 1H), 3.89-3.76 1,3-thiazole-5- (m, 4H), 3.70 (dd, J = 14.1, 7.6 Hz, 1H), carboxamide 3.21 (dt, J = 17.0, 7.2 Hz, 1H), 3.05 (dt, J = 16.9, 6.9 Hz, 1H), 2.88 (t, J = 7.1 Hz, 2H), 2.09 (dt, J = 12.1, 7.6 Hz, 1H), 1.92 (ddd, J = 19.6, 13.4, 7.1 Hz, 2H), 1.65 (dt, J = 19.6, 7.6 Hz, 1H) 199 2-{[(3,5-dimethyl- 1H NMR (400 MHz, methanol-d4) δ 8.74 (d, (APCI(+)) 1,2-oxazol-4- J = 7.0 Hz, 1H), 8.17 (d, J = 2.0 Hz, 1H), m/e 495 yl)acetyl][(2R)- 8.11 (s, 1H), 7.99 (d, J = 2.2 Hz, 1H), 7.79 (M + H)+ tetrahydrofuran-2- (s, 1H), 7.47 (d, J = 7.1 Hz, 1H), 4.72 (s, ylmethyl]amino}-N- 2H), 4.68 (d, J = 13.1 Hz, 1H), 4.39-4.19 (imidazo[1,2- (m, 3H), 4.03-3.88 (m, 2H), 3.77 (dd, J = a]pyridin-7- 13.8, 7.6 Hz, 1H), 2.32 (s, 3H), 2.23-2.11 ylmethyl)-1,3- (m, 4H), 2.09-1.91 (m, 2H), 1.77-1.63 thiazole-5- (m, 1H) carboxamide 202 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ 9.20 (s, (APCI(+)) a]pyridin-7- 1H), 8.74 (d, J = 7.2 Hz, 1H), 8.17 (d, J = m/e 480 ylmethyl)-2-{[(1- 2.0 Hz, 1H), 8.10 (s, 1H), 7.99 (d, J = 2.1 (M + H)+ methyl-1H-pyrazol- Hz, 1H), 7.79 (s, 1H), 7.57 (s, 1H), 7.47 (d, 4-yl)acetyl][(2R)- J = 5.9 Hz, 1H), 7.42 (s, 1H), 4.72 (s, 2H), tetrahydrofuran-2- 4.59 (d, J = 13.1 Hz, 1H), 4.31 (t, J = 7.1 ylmethyl]amino}- Hz, 1H), 4.22 (dd, J = 14.7, 9.1 Hz, 1H), 1,3-thiazole-5- 4.11 (s, 2H), 3.92 (dd, J = 14.9, 6.9 Hz, carboxamide 1H), 3.87 (s, 3H), 3.76 (dd, J = 14.2, 7.7 Hz, 1H), 2.19-2.06 (m, 1H), 2.00 (d, J = 7.3 Hz, 1H), 1.94 (dd, J = 13.4, 6.2 Hz, 1H), 1.69 (dt, J = 15.5, 7.5 Hz, 1H) 203 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ 8.74 (d, (APCI(+)) a]pyridin-7- J = 7.0 Hz, 1H), 8.17 (d, J = 2.0 Hz, 1H), m/e 493 ylmethyl)-2-{[3-(1- 8.10 (s, 1H), 7.99 (d, J = 2.1 Hz, 1H), 7.80 (M + H)+ methyl-1H-pyrrol-2- (s, 1H), 7.47 (d, J = 7.0 Hz, 1H), 6.54 (d, J = yl)propanoyl][(2R)- 2.5 Hz, 1H), 5.91 (t, J = 3.1 Hz, 1H), 5.83 tetrahydrofuran-2- (s, 1H), 4.72 (s, 2H), 4.50 (dd, J = 14.9, 2.3 ylmethyl]amino}- Hz, 1H), 4.28 (t, J = 6.8 Hz, 1H), 4.12 (dd, 1,3-thiazole-5- J = 14.8, 8.9 Hz, 1H), 3.85 (dd, J = 14.9, 6.8 carboxamide Hz, 1H), 3.77-3.65 (m, 1H), 3.58 (s, 3H), 3.25 (t, J = 8.4 Hz, 1H), 3.16-3.02 (m, 1H), 2.96 (t, J = 7.4 Hz, 2H), 2.10 (dt, J = 12.0, 7.3 Hz, 1H), 2.04-1.81 (m, 2H), 1.66 (dt, J = 15.7, 7.4 Hz, 1H) - The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-aminobutyl)piperidine-1-carboxylate for 4-amino-N-isopentylbenzamide. 1H NMR (500 MHz, DMSO-d6, Temp=90° C.) δ ppm 8.79-8.76 (m, 1H), 8.10 (bs, 1H), 7.81-7.78 (m, 1H), 7.45-7.37 (m, 2H), 7.02 (dd, J=9.5, 2.1 Hz, 1H), 6.04-5.96 (m, 1H), 3.93-3.85 (m, 2H), 3.14-3.06 (m, 2H), 2.75-2.63 (m, 2H), 1.67-1.57 (m, 2H), 1.50-1.19 (m, 16H), 1.07-0.91 (m, 2H); MS (ESI(+)) m/e 416 (M+H)+.
- The title compound was prepared as described in Example 1, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for imidazo[1,2-a]pyridin-6-amine in Example 1C. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.87 (s, 1H), 8.46-8.41 (m, 1H), 8.23-8.15 (m, 1H), 7.97-7.93 (m, 1H), 7.76-7.70 (m, 2H), 7.57-7.51 (m, 2H), 7.49-7.43 (m, 2H), 7.21 (dd, J=9.2, 1.7 Hz, 1H), 6.77 (t, J=5.9 Hz, 1H), 4.30 (d, J=5.8 Hz, 2H), 3.29-3.19 (m, 2H), 1.67-1.53 (m, 1H), 1.45-1.35 (m, 2H), 0.93-0.87 (m, 6H); MS (ESI(+)) m/e 380 (M+H)+.
- The title compound was prepared as described in Example 3, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for imidazo[1,2-a]pyridin-6-amine in Example 3A. 1H NMR (400 MHz, DMSO-d6, Temp=90° C.) δ 9.34 (bs, 1H), 8.71 (s, 1H), 8.38-8.33 (m, 1H), 8.23 (d, J=1.9 Hz, 1H), 7.97 (d, J=1.9 Hz, 1H), 7.86-7.75 (m, 2H), 7.44-7.38 (m, 2H), 7.32-7.26 (m, 2H), 6.69-6.62 (m, 1H), 4.43-4.38 (m, 2H), 2.29-2.18 (m, 3H), 1.81-1.68 (m, 2H), 1.67-1.45 (m, 4H), 1.29-1.15 (m, 2H); MS (ESI(+)) m/e 392 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]butyl}piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]butyl}piperidine for 3-methylbutan-1-amine and 2-isopropoxyacetic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6/D2O) δ ppm 9.18 (dd, J=1.9, 0.8 Hz, 1H), 8.30-8.19 (m, 1H), 7.98 (d, J=2.1 Hz, 1H), 7.84 (d, J=9.7 Hz, 1H), 7.76-7.72 (m, 1H), 4.03 (s, 4H), 3.72-3.52 (m, 1H), 3.14 (t, J=6.9 Hz, 2H), 2.77 (s, 2H), 1.69 (dd, J=12.9, 2.3 Hz, 2H), 1.58-1.40 (m, 4H), 1.41-1.31 (m, 2H), 1.31-1.21 (m, 2H), 1.11 (t, J=5.2 Hz, 6H), 1.03 (d, J=10.2 Hz, 2H); MS (ESI(+)) m/e 416 (M+H)+.
-
TABLE 5 The following Examples were prepared essentially as described in Example 62, substituting the appropriate carboxylic acid in Example 62B. Some products were purified by flash chromatography while others were purified by reverse-phase HPLC. Accordingly, some Examples were isolated as trifluoroacetic acid salts. Ex Name 1H NMR MS 63 1-{4-[1-(1,4- 1H NMR (400 MHz, DMSO-d6/D2O, (ESI(+)) dioxan-2- Temp = 90° C.) δ ppm 9.17 (dd, J = 2.0, 0.8 Hz, m/e 430 ylcarbonyl)piper- 1H), 8.23 (d, J = 1.7 Hz, 1H), 7.97 (d, J = 2.1 (M + H)+ idin-4-yl]butyl}-3- Hz, 1H), 7.83 (d, J = 9.7 Hz, 1H), 7.74 (dd, J = imidazo[1,2- 9.7, 1.9 Hz, 1H), 4.27 (dt, J = 16.5, 8.3 Hz, a]pyridin-6-ylurea 1H), 3.80-3.70 (m, 2H), 3.70-3.58 (m, 3H), 3.58-3.43 (m, 1H), 3.13 (q, J = 7.1 Hz, 2H), 1.69 (d, J = 11.6 Hz, 2H), 1.56-1.43 (m, 4H), 1.42-1.21 (m, 6H), 1.03 (s, 2H) 64 1-{4-[1- 1H NMR (400 MHz, DMSO-d6/D2O, (ESI(+)) (cyclopropylace- Temp = 90° C.) δ ppm 9.25-9.11 (m, 1H), 8.24 m/e 398 tyl)-piperidin-4- (d, J = 1.8 Hz, 1H), 7.98 (d, J = 2.0 Hz, 1H), (M + H)+ yl]butyl}-3- 7.84 (d, J = 9.7 Hz, 1H), 7.81-7.71 (m, 1H), imidazo[1,2- 3.98 (s, 1H), 3.24-3.06 (m, 3H), 2.23 (d, J = a]pyridin-6-ylurea 6.7 Hz, 2H), 1.68 (d, J = 12.9 Hz, 2H), 1.61- 1.41 (m, 4H), 1.39-1.20 (m, 4H), 1.09-0.85 (m, 4H), 0.49-0.35 (m, 2H), 0.22-0.05 (m, 2H) 65 1-imidazo[1,2- 1H NMR (400 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6-yl-3- Temp = 90° C.) δ ppm 9.24-9.11 (m, 1H), 8.23 m/e 440 {4-[1-(4,4,4- (d, J = 2.1 Hz, 1H), 7.97 (d, J = 2.0 Hz, 1H), (M + H)+ trifluorobutanoyl)pi- 7.83 (d, J = 9.7 Hz, 1H), 7.77-7.69 (m, 1H), peridin-4- 3.14 (t, J = 6.9 Hz, 2H), 2.56 (dd, J = 10.8, 4.4 yl]butyl}urea Hz, 3H), 2.51-2.40 (m, 2H), 1.69 (d, J = 12.0 Hz, 2H), 1.63-1.43 (m, 4H), 1.41-1.22 (m, 4H), 0.98 (dd, J = 36.1, 8.5 Hz, 2H) 66 1-imidazo[1,2- 1H NMR (400 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6-yl-3- Temp = 90° C.) δ ppm 9.17 (dd, J = 1.9, 0.8 Hz, m/e 402 {4-[1-(tetrahydro- 1H); 8.23 (d, J = 2.0 Hz, 1H), 7.97 (d, J = 2.1 (M + H)+ 2H-pyran-4- Hz, 1H), 7.82 (d, J = 9.3 Hz, 1H), 7.73 (dd, J = ylacetyl)piperidin- 9.7, 1.9 Hz, 1H), 7.55 (dd, J = 8.4, 4.5 Hz, 2H), 4-yl]butyl}urea 4.46 (d, J = 12.6 Hz, 2H), 3.16 (dd, J = 18.1, 11.2 Hz, 2H), 2.78 (t, J = 12.3 Hz, 3H), 1.68 (d, J = 9.8 Hz, 2H), 1.54-1.42 (m, 4H), 1.33 (s, 8H), 1.26 (t, J = 7.0 Hz, 3H), 1.11-0.99 (m, 2H) 67 1-imidazo[1,2- 1H NMR (400 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6-yl-3- Temp = 90° C.) δ ppm 9.17 (dd, J = 1.9, 0.8 Hz, m/e 442 {4-[1- 1H), 8.30-8.19 (m, 1H), 7.98 (d, J = 2.1 Hz, (M + H)+ (tetrahydrofuran-2- 1H), 7.83 (d, J = 9.6 Hz, 1H), 7.75 (dd, J = 9.6, ylacetyl)piperidin- 1.9 Hz, 1H), 3.88-3.71 (m, 2H), 3.14 (t, J = 4-yl]butyl}urea 6.9 Hz, 2H), 2.23 (t, J = 6.9 Hz, 2H), 1.91 (ttd, J = 10.7, 6.9, 3.5 Hz, 1H), 1.68 (d, J = 12.1 Hz, 2H), 1.56 (t, J = 12.5 Hz, 2H), 1.53-1.42 (m, 4H), 1.42-1.28 (m, 2H), 1.22 (m, 4H), 0.99 (d, J = 10.1 Hz, 2H) 68 1-{4-[1- 1H NMR (400 MHz, DMSO-d6/D2O, (ESI(+)) (cyclopentylcarbon- Temp = 90° C.) δ ppm 9.23-9.13 (m, 1H), 8.23 m/e 412 yl)piperidin-4- (d, J = 2.1 Hz, 1H), 7.97 (d, J = 2.0 Hz, 1H), (M + H)+ yl]butyl}-3- 7.83 (d, J = 9.7 Hz, 1H), 7.82-7.71 (m, 1H), imidazo[1,2- 4.12 (s, 2H), 3.98 (s, 1H), 3.14 (t, J = 6.9 Hz, a]pyridin-6-ylurea 2H), 3.04-2.89 (m, 2H), 2.77 (s, 2H), 1.87- 1.59 (m, 8H), 1.51-1.33 (m, 6H), 1.40-1.10 (m, 4H), 1.08-0.91 (m, 2H) 69 1-imidazo[1,2- 1H NMR (400 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6-yl-3- Temp = 90° C.) δ 9 ppm. 23-9.14 (m, 1H), 8.24 m/e 428 {4-[1-(tetrahydro- (d, J = 1.9 Hz, 1H), 7.98 (d, J = 2.1 Hz, 1H), (M + H)+ 2H-pyran-4- 7.84 (d, J = 9.7 Hz, 1H), 7.79-7.68 (m, 1H), ylcarbonyl)piperi- 4.11 (s, 2H), 3.88-3.77 (m, 2H), 3.51-3.36 din-4-yl]butyl}urea (m, 2H), 3.21-3.09 (m, 2H), 2.92-2.73 (m, 2H), 1.76-1.56 (m, 4H), 1.56-1.42 (m, 6H), 1.45-1.18 (m, 4H), 1.04-0.87 (m, 2H) 70 1-imidazo[1,2- 1H NMR (400 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6-yl-3- Temp = 90° C.) δ ppm 9.17 (dd, J = 1.9, 0.8 Hz, m/e 432 (4-{1-[(2- 1H), 8.24 (d, J = 1.9 Hz, 1H), 7.98 (d, J = 2.1 (M + H)+ methoxyethoxy)ace- Hz, 1H), 7.84 (d, J = 9.7 Hz, 1H), 7.75 (dd, J = tyl]piperidin-4- 9.7, 1.9 Hz, 1H), 4.09 (d, J = 7.6 Hz, 2H), 3.56 yl}butyl)urea (dd, J = 6.0, 3.8 Hz, 2H), 3.47 (dd, J = 5.7, 3.7 Hz, 2H), 3.26 (s, 2H), 3.19-3.07 (m, 2H), 1.68 (dd, J = 13.0, 2.2 Hz, 2H), 1.48 (dt, J = 14.1, 7.0 Hz, 4H), 1.40-1.22 (m, 6H), 1.04 (d, J = 9.3 Hz, 2H) 71 1-imidazo[1,2- 1H NMR (400 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6-yl-3- Temp = 90° C.) δ ppm 9.26-9.11 (m, 1H), 8.23 m/e 443 {4-[1-(morpholin-4- (d, J = 1.8 Hz, 1H), 7.98 (d, J = 2.1 Hz, 1H), (M + H)+ ylacetyl)piperidin- 7.83 (t, J = 8.1 Hz, 1H), 7.80-7.71 (m, 1H), 4-yl]butyl}urea 4.22 (s, 2H), 3.98 (s, 1H), 3.93-3.84 (m, 4H), 3.62 (s, 1H), 3.18-3.07 (m, 2H), 2.71 (s, 2H), 1.80-1.67 (m, 2H), 1.51 (dq, J = 21.7, 7.0 Hz, 4H), 1.42-1.20 (m, 6H), 1.07 (s, 2H) 72 1-imidazo[1,2- 1H NMR (400 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6-yl-3- Temp = 90° C.) δ ppm 9.25-9.14 (m, 1H), 8.24 m/e 414 {4-[1- (d, J = 1.9 Hz, 1H), 7.98 (d, J = 2.0 Hz, 1H), (M + H)+ (tetrahydrofuran-3- 7.84 (d, J = 9.7 Hz, 1H), 7.79-7.69 (m, 1H), ylcarbonyl)piperi- 3.85 (t, J = 8.1 Hz, 2H), 3.70 (h, J = 7.8 Hz, din-4-yl]butyl}urea 4H), 3.20-3.08 (m, 2H), 2.09-1.91 (m, 2H), 1.70 (d, J = 12.1 Hz, 2H), 1.61-1.43 (m, 4H), 1.37-1.24 (m, 4H), 1.08-0.88 (m, 2H) 73 1-imidazo[1,2- 1H NMR (400 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6-yl-3- Temp = 90° C.) δ ppm 9.22-9.12 (m, 1H), 8.24 m/e 428 {4-[1- (d, J = 2.1 Hz, 1H), 7.98 (d, J = 2.0 Hz, 1H), (M + H)+ (tetrahydrofuran-3- 7.84 (d, J = 9.7 Hz, 1H), 7.79-7.69 (m, 1H), ylacetyl)piperidin- 3.98 (s, 1H), 3.86-3.76 (m, 1H), 3.75-3.68 4-yl]butyl}urea (m, 1H), 3.68-3.57 (m, 1H), 3.28-3.23 (m, 1H), 3.14 (t, J = 6.9 Hz, 2H), 2.50-2.43 (m, 1H), 2.43-2.30 (m, 2H), 2.09-1.92 (m, 1H), 1.68 (d, J = 13.3 Hz, 2H), 1.56-1.41 (m, 6H), 1.38-1.29 (m, 2H), 1.25 (dd, J = 14.2, 6.0 Hz, 2H), 1.00 (d, J = 10.2 Hz, 2H) 74 1-imidazo[1,2- 1H NMR (400 MHz, DMSO-d6/D2O, (ESI(+)) a]pyridin-6-yl-3- Temp = 90° C.) δ ppm 9.18 (d, J = 1.1 Hz, 1H), m/e 414 {4-[1- 8.24 (d, J = 2.0 Hz, 1H), 7.98 (d, J = 2.0 Hz, (M + H)+ (tetrahydrofuran-2- 1H), 7.84 (d, J = 9.6 Hz, 1H), 7.79-7.65 (m, ylcarbonyl)piperi- 1H), 4.59 (t, J = 6.7 Hz, 1H), 4.12 (s, 2H), 3.88- din-4-yl]butyl}urea 3.62 (m, 2H), 3.16 (dd, J = 18.1, 11.3 Hz, 2H), 2.02-1.93 (m, 2H), 1.93-1.72 (m, 2H), 1.69 (d, J = 12.7 Hz, 2H), 1.58-1.43 (m, 4H), 1.42-1.19 (m, 5H), 1.17-0.87 (m, 2H) 107 1-[4-(1- 1H NMR (400 MHz, methanol-d4) δ ppm 8.82- (ESI(+)) benzoylpiperidin- 8.77 (m, 1H), 7.76 (s, 1H), 7.50 (s, 1H), 7.48- m/e 420 4-yl)butyl]-3- 7.40 (m, 4H), 7.42-7.33 (m, 2H), 7.09 (dd, J = (M + H)+ imidazo[1,2- 9.5, 2.0 Hz, 1H), 4.65-4.57 (m, 1H), 3.74- a]pyridin-6-ylurea 3.65 (m, 1H), 3.21 (t, J = 6.9 Hz, 2H), 3.13- 3.03 (m, 1H), 2.88-2.78 (m, 1H), 1.90-1.82 (m, 1H), 1.74-1.46 (m, 4H), 1.48-1.26 (m, 4H), 1.28-1.04 (m, 2H) 270 1-[4-(1- (ESI(+)) benzoylpiperidin- m/e 420 4-yl)butyl]-3- (M + H)+ imidazo[1,2- a]pyridin-7-ylurea - The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 5-bromothiophene-2-carboxylic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 51A, substituting 5-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.99 (t, J=5.8 Hz, 1H), 8.46 (s, 1H), 8.14 (s, 1H), 7.95 (s, 1H), 7.79 (s, 1H), 7.69 (d, J=3.9 Hz, 1H), 7.49-7.58 (m, 2H), 7.20 (d, J=4.0 Hz, 2H), 4.43 (d, J=5.7 Hz, 2H), 3.91 (d, J=7.2 Hz, 2H), 2.11 (dq, J=13.6, 6.8 Hz, 1H), 0.84 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 380 (M+H)+.
-
TABLE 6 The following Examples were prepared essentially as described in Example 75, substituting the appropriate carboxylic acid and amine in Example 75A and the appropriate boronate in Example 75B. Some boronates were Boc-protected and required deprotection as in Example 28A. Ex Name 1H NMR MS 120 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.87 (ESI(+)) a]pyridin-6- (t, J = 6.0 Hz, 1 H), 8.46 (s, 1 H), 8.14 (s, 1 H), m/e 364 ylmethyl)-5-[1-(2- 7.96 (s, 1 H), 7.87 (s, 1 H), 7.53 (d, J = 6.8 Hz, (M + H)+ methylpropyl)-1H- 2 H), 7.21 (dd, J = 9.3, 1.4 Hz, 1 H), 7.14 (d, pyrazol-4-yl]furan- J = 3.6 Hz, 1 H), 6.64 (d, J = 3.5 Hz, 1 H), 4.44 2-carboxamide (d, J = 6.0 Hz, 2 H), 3.94 (d, J = 7.2 Hz, 2 H), 2.11 (dq, J = 13.6, 6.8 Hz, 1 H), 0.83 (d, J = 6.7 Hz, 6 H) 174 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.04 (ESI(+)) a]pyridin-7- (t, J = 6.0 Hz, 1 H), 8.48 (d, J = 7.0 Hz, 1 H), m/e 380 ylmethyl)-5-[1-(2- 8.14 (s, 1 H), 7.88 (s, 1 H), 7.80 (s, 1 H), 7.73 (M + H)+ methylpropyl)-1H- (d, J = 3.8 Hz, 1 H), 7.51 (s, 1 H), 7.38 (s, 1 H), pyrazol-4- 7.21 (d, J = 3.9 Hz, 1 H), 6.84 (dd, J = 7.0, 1.5 yl]thiophene-2- Hz, 1 H), 4.46 (d, J = 5.9 Hz, 2 H), 3.91 (d, carboxamide J = 7.3 Hz, 2 H), 2.11 (dq, J = 13.6, 6.7, 6.6 Hz, 1 H), 0.84 (d, J = 6.7 Hz, 6 H) 175 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.09 a]pyridin-6- (t, J = 5.9 Hz, 1 H), 8.81 (s, 1 H), 8.47 (s, 1 H), ylmethyl)-5-[1-(2- 8.31 (s, 1 H), 7.95 (s, 1 H), 7.76 (d, J = 3.9 Hz, methylpropanoyl)- 1 H), 7.54 (t, J = 4.6 Hz, 2 H), 7.50 (d, J = 3.9 1H-pyrazol-4- Hz, 1 H), 7.20 (dd, J = 9.2, 1.5 Hz, 1 H), 4.44 yl]thiophene-2- (d, J = 5.9 Hz, 2 H), 3.77 (dq, J = 6.9 Hz, 1 H), carboxamide 1.21 (d, J = 6.9 Hz, 6 H) 176 5-[1-(2-hydroxy-2- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.00 (ESI(+)) methylpropyl)-1H- (t, J = 5.9 Hz, 1 H), 8.46 (s, 1 H), 8.03 (s, 1 H), m/e 396 pyrazol-4-yl]-N- 7.95 (s, 1 H), 7.78 (s, 1 H), 7.69 (d, J = 3.8 Hz, (M + H)+ (imidazo[1,2- 1 H), 7.49-7.58 (m, 2 H), 7.16-7.25 (m, 2 a]pyridin-6- H), 4.76 (s, 1 H), 4.42 (d, J = 5.7 Hz, 2 H), 4.01 ylmethyl)thiophene- (s, 2 H), 1.06 (s, 6 H) 2-carboxamide 177 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.00 a]pyridin-6- (t, J = 5.9 Hz, 1 H), 8.46 (s, 1 H), 8.19 (s, 1 H), ylmethyl)-5-{1-[(3- 7.95 (s, 1 H), 7.83 (s, 1 H), 7.70 (d, J = 3.9 Hz, methyloxetan-3- 1 H), 7.48-7.58 (m, 2 H), 7.15-7.24 (m, 2 yl)methyl]-1H- H), 4.59 (d, J = 6.0 Hz, 2 H), 4.42 (d, J = 5.9 Hz, pyrazol-4- 2 H), 4.33 (s, 2 H), 4.22 (d, J = 6.0 Hz, 2 H), yl}thiophene-2- 1.13 (s, 3 H) carboxamide 178 5-[1- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.99 (cyclobutylmethyl)- (t, J = 5.9 Hz, 1 H), 8.46 (s, 1 H), 8.13 (s, 1 H), 1H-pyrazol-4-yl]- 7.95 (s, 1 H), 7.77 (s, 1 H), 7.69 (d, J = 3.9 Hz, N-(imidazo[1,2- 1 H), 7.48-7.57 (m, 2 H), 7.16-7.23 (m, 2 a]pyridin-6- H), 4.42 (d, J = 5.7 Hz, 2 H), 4.12 (d, J = 7.3 Hz, ylmethyl)thiophene- 2 H), 2.74 (dq, J = 7.5, 7.4 Hz, 1 H), 1.90-2.02 2-carboxamide (m, 2 H), 1.67-1.90 (m, 4 H) 179 5-[1- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.99 (ESI(+)) (cyclohexylmethyl)- (t, J = 5.9 Hz, 1 H), 8.46 (s, 1 H), 8.12 (s, 1 H), m/e 420 1H-pyrazol-4-yl]- 7.95 (s, 1 H), 7.78 (s, 1 H), 7.69 (d, J = 3.9 Hz, (M + H)+ N-(imidazo[1,2- 1 H), 7.48-7.57 (m, 2 H), 7.14-7.26 (m, 2 a]pyridin-6- H), 4.42 (d, J = 5.9 Hz, 2 H), 3.93 (d, J = 7.2 Hz, ylmethyl)thiophene- 2 H), 1.72-1.88 (m, 1 H), 1.54-1.70 (m, 3 2-carboxamide H), 1.50 (d, J = 12.1 Hz, 2 H), 1.03-1.28 (m, 3 H), 0.85-1.01 (m, 2 H) 180 5-{1-[(2R)-2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.99 hydroxybutyl]-1H- (t, J = 5.8 Hz, 1 H), 8.46 (s, 1 H), 8.08 (s, 1 H), pyrazol-4-yl}-N- 7.95 (s, 1 H), 7.78 (s, 1 H), 7.69 (d, J = 3.9 Hz, (imidazo[1,2- 1 H), 7.50-7.58 (m, 2 H), 7.17-7.23 (m, 2 a]pyridin-6- H), 4.92 (d, J = 5.4 Hz, 1 H), 4.42 (d, J = 5.7 Hz, ylmethyl)thiophene- 2 H), 4.03-4.12 (m, 1 H), 3.93-4.02 (m, 1 2-carboxamide H), 3.66-3.76 (m, 1 H), 1.20-1.44 (m, 2 H), 0.88 (t, J = 7.4 Hz, 3 H) 182 5-[1-(2-hydroxy-2- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.04 methylpropyl)-1H- (t, J = 5.9 Hz, 1 H), 8.48 (d, J = 7.0 Hz, 1 H), pyrazol-4-yl]-N- 8.04 (s, 1 H), 7.88 (s, 1 H), 7.79 (s, 1 H), 7.73 (imidazo[1,2- (d, J = 3.8 Hz, 1 H), 7.51 (s, 1 H), 7.38 (s, 1 H), a]pyridin-7- 7.23 (d, J = 3.8 Hz, 1 H), 6.84 (dd, J = 7.0, 1.3 ylmethyl)thiophene- Hz, 1 H), 4.75 (s, 1 H), 4.46 (d, J = 5.9 Hz, 2 2-carboxamide H), 4.01 (s, 2 H), 1.07 (s, 6 H) 186 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.00 (ESI(+)) a]pyridin-6- (t, J = 5.8 Hz, 1 H), 8.46 (s, 1 H), 8.07 (s, 1 H), m/e 422 ylmethyl)-5-[1- 7.95 (s, 1 H), 7.78 (s, 1 H), 7.69 (d, J = 3.8 Hz, (M + H)+ (tetrahydro-2H- 1 H), 7.48-7.57 (m, 2 H), 7.14-7.27 (m, 2 pyran-2-ylmethyl)- H), 4.42 (d, J = 5.9 Hz, 2 H), 4.05-4.15 (m, 2 1H-pyrazol-4- H), 3.83 (d, J = 11.1 Hz, 1 H), 3.55-3.71 (m, 1 yl]thiophene-2- H), 3.19-3.37 (m, 2 H), 1.68-1.85 (m, 1 H), carboxamide 1.48-1.63 (m, 1 H), 1.32-1.50 (m, 2 H), 1.06-1.29 (m, 1 H) 200 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.00 a]pyridin-6- (t, J = 5.8 Hz, 1 H), 8.46 (s, 1 H), 8.20 (s, 1 H), ylmethyl)-5-[1- 7.95 (s, 1 H), 7.81 (s, 1 H), 7.69 (d, J = 3.9 Hz, (tetrahydrofuran-3- 1 H), 7.49-7.57 (m, 2 H), 7.15-7.24 (m, 2 ylmethyl)-1H- H), 4.42 (d, J = 5.7 Hz, 2 H), 4.10 (d, J = 7.5 Hz, pyrazol-4- 2 H), 3.69-3.79 (m, 1 H), 3.56-3.70 (m, 2 yl]thiophene-2- H), 3.46 (dd, J = 8.7, 5.4 Hz, 2 H), 1.81-1.98 carboxamide (m, 1 H), 1.52-1.65 (m, 1 H) 201 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.99 a]pyridin-6- (t, J = 5.8 Hz, 1 H), 8.46 (s, 1 H), 8.14 (s, 1 H), ylmethyl)-5-[1- 7.95 (s, 1 H), 7.80 (s, 1 H), 7.69 (d, J = 3.9 Hz, (tetrahydro-2H- 1 H), 7.48-7.58 (m, 2 H), 7.12-7.25 (m, 2 pyran-4-ylmethyl)- H), 4.43 (d, J = 5.7 Hz, 2 H), 4.00 (d, J = 7.2 Hz, 1H-pyrazol-4- 2 H), 3.81 (dd, J = 11.3, 2.9 Hz, 2 H), 3.24 (td, yl]thiophene-2- J = 11.6, 1.7 Hz, 2 H), 1.91-2.18 (m, 1 H), carboxamide 1.39 (dd, J = 12.7, 1.4 Hz, 2 H), 1.14-1.30 (m, 2 H) 206 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.99 a]pyridin-6- (t, J = 5.8 Hz, 1 H), 8.46 (s, 1 H), 8.15 (s, 1 H), ylmethyl)-5-[1- 7.95 (s, 1 H), 7.80 (s, 1 H), 7.69 (d, J = 3.9 Hz, (tetrahydro-2H- 1 H), 7.53 (t, J = 4.6 Hz, 2 H), 7.15-7.26 (m, 2 pyran-3-ylmethyl)- H), 4.43 (d, J = 5.9 Hz, 2 H), 4.02 (dd, J = 7.2, 1H-pyrazol-4- 3.2 Hz, 2 H), 3.64-3.72 (m, 1 H), 3.61 (dd, yl]thiophene-2- J = 11.1, 3.3 Hz, 1 H), 3.15 (dd, J = 11.2, 8.8 Hz, carboxamide 1 H), 1.96-2.18 (m, 1 H), 1.52-1.70 (m, 2 H), 1.34-1.51 (m, 1 H), 1.10-1.31 (m, 2 H) 219 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.99 a]pyridin-6- (t, J = 5.9 Hz, 1 H), 8.46 (s, 1 H), 8.10 (s, 1 H), ylmethyl)-5-[1- 7.95 (s, 1 H), 7.79 (s, 1 H), 7.70 (d, J = 3.9 Hz, (tetrahydrofuran-2- 1 H), 7.46-7.60 (m, 2 H), 7.11-7.26 (m, 2 ylmethyl)-1H- H), 4.43 (d, J = 5.9 Hz, 2 H), 4.04-4.25 (m, 3 pyrazol-4- H), 3.69-3.80 (m, 1 H), 3.62 (q, J = 7.4 Hz, 1 yl]thiophene-2- H), 1.86-2.01 (m, 1 H), 1.68-1.84 (m, 2 H), carboxamide 1.52-1.67 (m, 1 H) 247 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 422 ylmethyl)-5-[1- (M + H)+ (tetrahydro-2H- pyran-2-ylmethyl)- 1H-pyrazol-4- yl]thiophene-2- carboxamide 248 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 408 ylmethyl)-5-[1- (M + H)+ (tetrahydrofuran-2- ylmethyl)-1H- pyrazol-4- yl]thiophene-2- carboxamide 252 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 408 ylmethyl)-5-[1- (M + H)+ (tetrahydrofuran-3- ylmethyl)-1H- pyrazol-4- yl]thiophene-2- carboxamide 253 N-(imidazo[1,2- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.04 (ESI(+)) a]pyridin-7- (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 7.2, 1.1 Hz, m/e 422 ylmethyl)-5-[1- 1H), 8.16 (s, 1H), 7.89 (t, J = 1.0 Hz, 1H), (M + H)+ (tetrahydro-2H- 7.82 (s, 1H), 7.74 (d, J = 3.9 Hz, 1H), 7.52 (d, pyran-3-ylmethyl)- J = 1.4 Hz, 1H), 7.40 (s, 1H), 7.22 (d, J = 3.8 1H-pyrazol-4- Hz, 1H), 6.85 (dd, J = 7.0, 1.7 Hz, 1H), 4.48 yl]thiophene-2- (d, J = 5.7 Hz, 2H), 4.03 (dd, J = 7.3, 2.1 Hz, carboxamide 2H), 3.76-3.57 (m, 2H), 3.42-3.32 (m, 1H), 3.17 (dd, J = 11.2, 8.7 Hz, 1H), 2.15-1.98 (m, 1H), 1.77-1.54 (m, 2H), 1.54-1.35 (m, 1H), 1.32-1.14 (m, 1H) 254 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 408 ylmethyl)-5-{1-[(3- (M + H)+ methyloxetan-3- yl)methyl]-1H- pyrazol-4- yl}thiophene-2- carboxamide 265 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 422 ylmethyl)-5-[1- (M + H)+ (tetrahydro-2H- pyran-4-ylmethyl)- 1H-pyrazol-4- yl]thiophene-2- carboxamide 269 N-(imidazo[1,2- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (ESI(+)) a]pyridin-7- (t, J = 5.9 Hz, 1H), 8.53-8.45 (m, 1H), 8.13 m/e 382 ylmethyl)-5-[1-(2- (s, 1H), 7.89 (s, 1H), 7.81 (s, 1H), 7.74 (d, J = (M + H)+ methoxyethyl)-1H- 3.9 Hz, 1H), 7.52 (d, J = 1.1 Hz, 1H), 7.40 (s, pyrazol-4- 1H), 7.22 (d, J = 3.8 Hz, 1H), 6.85 (dd, J = yl]thiophene-2- 7.0, 1.6 Hz, 1H), 4.48 (d, J = 5.9 Hz, 2H), carboxamide 4.27 (t, J = 5.3 Hz, 2H), 3.70 (t, J = 5.3 Hz, 2H), 3.24 (s, 3H) 272 5-[1- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.04 (ESI(+)) (cyclohexylmethyl)- (t, J = 6.1 Hz, 1H), 8.49 (d, J = 7.8 Hz, 1H), m/e 448 5-ethyl-1H- 7.89 (s, 1H), 7.78 (d, J = 4.1 Hz, 1H), 7.72 (s, (M + H)+ pyrazol-4-yl]-N- 1H), 7.52 (d, J = 1.0 Hz, 1H), 7.40 (s, 1H), (imidazo[1,2- 7.17 (d, J = 4.1 Hz, 1H), 6.85 (dd, J = 7.1, 1.7 a]pyridin-7- Hz, 1H), 4.48 (d, J = 5.8 Hz, 2H), 3.90 (d, J = ylmethyl)thiophene- 7.5 Hz, 2H), 2.87 (q, J = 7.2 Hz, 2H), 1.79- 2-carboxamide 1.95 (m, 1H), 1.59-1.73 (m, J = 3.4 Hz, 3H), 1.54 (d, J = 12.5 Hz, 2H), 1.09-1.25 (m, 6H), 0.93-1.08 (m, J = 11.9 Hz, 2H) 273 N-(imidazo[1,2- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (ESI(+)) a]pyridin-7- (t, J = 5.9 Hz, 1H), 8.49 (d, J = 7.1 Hz, 1H), m/e 492 ylmethyl)-5-{1-[(1- 7.89 (s, 1H), 7.79 (d, J = 3.7 Hz, 1H), 7.74 (s, (M + H)+ methoxy-3,3- 1H), 7.52 (d, J = 1.0 Hz, 1H), 7.40 (s, 1H), dimethylcyclohex- 7.18 (d, J = 4.1 Hz, 1H), 6.85 (dd, J = 7.1, 1.7 yl)methyl]-5-methyl- Hz, 1H), 4.48 (d, J = 5.8 Hz, 2H), 3.97-4.16 1H-pyrazol-4- (m, 2H), 3.20 (s, 3H), 2.45 (s, 3H), 1.64-1.78 yl}thiophene-2- (m, 1H), 1.27-1.59 (m, 4H), 0.99-1.24 (m, carboxamide 3H), 0.96 (s, 3H), 0.85 (s, 3H) 293 N-(imidazo[1,2- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (ESI(+)) a]pyridin-7- (s, 1H), 8.47 (t, J = 9.6 Hz, 1H), 8.17 (s, 1H), m/e 366 ylmethyl)-5-(1- 7.89 (s, 1H), 7.80 (s, 1H), 7.74 (d, J = 3.9 Hz, (M + H)+ propyl-1H-pyrazol- 1H), 7.52 (d, J = 1.1 Hz, 1H), 7.40 (s, 1H), 4-yl)thiophene-2- 7.22 (d, J = 3.8 Hz, 1H), 6.83 (dt, J = 14.9, 7.4 carboxamide Hz, 1H), 4.48 (d, J = 5.9 Hz, 2H), 4.07 (t, J = 7.0 Hz, 2H), 1.81 (dd, J = 14.4, 7.2 Hz, 2H), 0.84 (t, J = 7.4 Hz, 3H) 294 N-(imidazo[1,2- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (ESI(+)) a]pyridin-7- (t, J = 5.9 Hz, 1H), 8.49 (d, J = 7.0 Hz, 1H), m/e 437 ylmethyl)-5-{1-[2- 8.17 (s, 1H), 7.89 (s, 1H), 7.80 (s, 1H), 7.74 (M + H)+ (morpholin-4- (d, J = 3.9 Hz, 1H), 7.52 (d, J = 1.2 Hz, 1H), yl)ethyl]-1H- 7.40 (s, 1H), 7.22 (d, J = 3.8 Hz, 1H), 6.85 pyrazol-4- (dd, J = 7.0, 1.5 Hz, 1H), 4.48 (d, J = 5.9 Hz, yl}thiophene-2- 2H), 4.24 (t, J = 6.5 Hz, 2H), 3.59-3.49 (m, carboxamide 4H), 2.72 (t, J = 6.5 Hz, 2H), 2.45-2.35 (m, 4H) 295 5-(1-ethyl-1H- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.02 (ESI(+)) pyrazol-4-yl)-N- (t, J = 5.9 Hz, 1H), 8.49 (d, J = 7.0 Hz, 1H), m/e 352 (imidazo[1,2- 8.17 (s, 1H), 7.89 (s, 1H), 7.79 (s, 1H), 7.74 (M + H)+ a]pyridin-7- (d, J = 3.8 Hz, 1H), 7.52 (d, J = 1.2 Hz, 1H), ylmethyl)thiophene- 7.40 (s, 1H), 7.21 (d, J = 3.8 Hz, 1H), 6.85 2-carboxamide (dd, J = 7.0, 1.6 Hz, 1H), 4.48 (d, J = 5.9 Hz, 2H), 4.15 (q, J = 7.3 Hz, 2H), 1.39 (t, J = 7.3 Hz, 3H) 296 5-[1-(1,1- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.05 (ESI(+)) dioxidotetrahydro- (t, J = 6.0 Hz, 1H), 8.49 (d, J = 6.9 Hz, 1H), m/e 442 thiophen-3-yl)-1H- 8.32 (s, 1H), 7.94 (s, 1H), 7.89 (s, 1H), 7.76 (M + H)+ pyrazol-4-yl]-N- (d, J = 3.8 Hz, 1H), 7.52 (d, J = 1.1 Hz, 1H), (imidazo[1,2- 7.40 (s, 1H), 7.26 (d, J = 3.8 Hz, 1H), 6.85 a]pyridin-7- (dd, J = 7.0, 1.6 Hz, 1H), 5.35-5.18 (m, 1H), ylmethyl)thiophene- 4.48 (d, J = 5.9 Hz, 2H), 3.75 (dd, J = 13.6, 2-carboxamide 8.2 Hz, 1H), 3.48 (m, 2H), 3.35-3.20 (m, 1H), 2.78-2.53 (m, 2H) 300 N-(imidazo[1,2- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.04 (ESI(+)) a]pyridin-7- (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 7.0, 0.8 Hz, m/e 430 ylmethyl)-5-{1-[2- 1H), 8.25 (s, 1H), 7.89 (d, J = 1.4 Hz, 2H), (M + H)+ (methylsulfonyl)eth- 7.75 (d, J = 3.9 Hz, 1H), 7.52 (d, J = 1.2 Hz, yl]-1H-pyrazol-4- 1H), 7.40 (s, 1H), 7.24 (d, J = 3.8 Hz, 1H), yl}thiophene-2- 6.85 (dd, J = 7.0, 1.7 Hz, 1H), 4.57 (t, J = 6.9 carboxamide Hz, 2H), 4.48 (d, J = 5.9 Hz, 2H), 3.73 (t, J = 6.9 Hz, 2H), 2.93 (s, 3H) 304 5-{1-[(2R)-2- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.02 (ESI(+)) hydroxypropyl]- (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 7.0, 0.7 Hz, m/e 382 1H-pyrazol-4-yl}- 1H), 8.09 (s, 1H), 7.89 (s, 1H), 7.80 (d, J = 0.5 (M + H)+ N-(imidazo[1,2- Hz, 1H), 7.74 (d, J = 3.9 Hz, 1H), 7.52 (d, J = a]pyridin-7- 1.2 Hz, 1H), 7.40 (s, 1H), 7.22 (d, J = 3.8 Hz, ylmethyl)thiophene- 1H), 6.85 (dd, J = 7.0, 1.6 Hz, 1H), 4.93 (d, J = 2-carboxamide 4.7 Hz, 1H), 4.48 (d, J = 5.9 Hz, 2H), 4.11- 3.93 (m, 3H), 1.12-0.98 (m, 3H) 316 5-[1-(1,4-dioxan-2- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (ESI(+)) ylmethyl)-1H- (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 7.0, 0.7 Hz, m/e 424 pyrazol-4-yl]-N- 1H), 8.12 (s, 1H), 7.89 (s, 1H), 7.82 (s, 1H), (M + H)+ (imidazo[1,2- 7.74 (d, J = 3.8 Hz, 1H), 7.52 (d, J = 1.2 Hz, a]pyridin-7- 1H), 7.40 (s, 1H), 7.23 (d, J = 3.8 Hz, 1H), ylmethyl)thiophene- 6.85 (dd, J = 7.0, 1.6 Hz, 1H), 4.48 (d, J = 5.9 2-carboxamide Hz, 2H), 4.20-4.14 (m, 2H), 3.96-3.83 (m, 1H), 3.79-3.70 (m, 2H), 3.68-3.39 (m, 3H), 3.29-3.21 (m, 1H) 317 5-[1-(2- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.02 (ESI(+)) hydroxyethyl)-1H- (t, J = 5.9 Hz, 1H), 8.49 (dd, J = 7.0, 0.7 Hz, m/e 368 pyrazol-4-yl]-N- 1H), 8.12 (s, 1H), 7.89 (d, J = 0.8 Hz, 1H), (M + H)+ (imidazo[1,2- 7.80 (d, J = 0.6 Hz, 1H), 7.74 (d, J = 3.8 Hz, a]pyridin-7- 1H), 7.52 (d, J = 1.2 Hz, 1H), 7.40 (s, 1H), ylmethyl)thiophene- 7.22 (d, J = 3.9 Hz, 1H), 6.85 (dd, J = 7.0, 1.6 2-carboxamide Hz, 1H), 4.92 (t, J = 5.3 Hz, 1H), 4.48 (d, J = 5.9 Hz, 2H), 4.15 (t, J = 5.6 Hz, 2H), 3.75 (q, J = 5.5 Hz, 2H) 344 5-{1-[(1,1- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.04 (ESI(+)) dioxidotetrahydro- (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 7.0, 0.8 Hz, m/e 470 2H-thiopyran-3- 1H), 8.19 (d, J = 0.4 Hz, 1H), 7.89 (d, J = 0.8 (M + H)+ yl)methyl]-1H- Hz, 1H), 7.86 (d, J = 0.5 Hz, 1H), 7.75 (d, J = pyrazol-4-yl}-N- 3.9 Hz, 1H), 7.52 (d, J = 1.2 Hz, 1H), 7.40 (s, (imidazo[1,2- 1H), 7.24 (d, J = 3.9 Hz, 1H), 6.85 (dd, J = a]pyridin-7- 7.0, 1.7 Hz, 1H), 4.48 (d, J = 5.8 Hz, 2H), ylmethyl)thiophene- 4.13 (d, J = 6.6 Hz, 2H), 3.09-2.83 (m, 4H), 2-carboxamide 2.47-2.40 (m, 1H), 2.14-1.96 (m, 1H), 1.88- 1.69 (m, 1H), 1.69-1.54 (m, 1H), 1.37- 1.14 (m, 1H) 345 N-(imidazo[1,2- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (ESI(+)) a]pyridin-7- (t, J = 6.0 Hz, 1H), 8.49 (d, J = 7.0 Hz, 1H), m/e 338 ylmethyl)-5-(1- 8.12 (s, 1H), 7.89 (s, 1H), 7.79 (s, 1H), 7.74 (M + H)+ methyl-1H-pyrazol- (d, J = 3.8 Hz, 1H), 7.52 (d, J = 1.1 Hz, 1H), 4-yl)thiophene-2- 7.40 (s, 1H), 7.21 (d, J = 3.8 Hz, 1H), 6.84 carboxamide (dd, J = 7.0, 1.6 Hz, 1H), 4.48 (d, J = 5.9 Hz, 2H), 3.86 (s, 3H) 363 N-(imidazo[1,2- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.22 (ESI(+)) a]pyridin-7- (t, J = 5.9 Hz, 1H), 8.50 (dd, J = 6.9, 0.8 Hz, m/e 338 ylmethyl)-5-(1- 1H), 7.92-7.86 (m, 2H), 7.53 (d, J = 1.2 Hz, (M + H)+ methyl-1H-pyrazol- 1H), 7.48 (d, J = 2.0 Hz, 1H), 7.45 (d, J = 3.9 5-yl)thiophene-2- Hz, 1H), 7.41 (s, 1H), 6.86 (dd, J = 7.0, 1.7 carboxamide Hz, 1H), 6.59 (d, J = 1.9 Hz, 1H), 4.51 (d, J = 5.9 Hz, 2H), 3.98 (s, 3H) 395 N-(imidazo[1,2- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (ESI(+)) a]pyridin-7- (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 6.9, 1.0 Hz, m/e 408 ylmethyl)-5-{1- 1H), 8.12 (s, 1H), 7.89 (t, J = 1.0 Hz, 1H), (M + H)+ [(2R)- 7.81 (s, 1H), 7.74 (d, J = 4.0 Hz, 1H), 7.52 (d, tetrahydrofuran-2- J = 1.5 Hz, 1H), 7.40 (s, 1H), 7.23 (d, J = 4.0 ylmethyl]-1H- Hz, 1H), 6.85 (dd, J = 7.0, 1.7 Hz, 1H), 4.48 pyrazol-4- (d, J = 5.9 Hz, 2H), 4.26-4.04 (m, 3H), 3.82- yl}thiophene-2- 3.69 (m, 1H), 3.69-3.57 (m, 1H), 2.00-1.85 carboxamide (m, 1H), 1.85-1.70 (m, 2H), 1.70-1.52 (m, 1H) 397 N-(imidazo[1,2- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.02 (ESI(+)) a]pyridin-7- (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 6.9, 1.0 Hz, m/e 408 ylmethyl)-5-{1- 1H), 8.11 (d, J = 0.9 Hz, 1H), 7.89 (d, J = 0.9 (M + H)+ [(2S)- Hz, 1H), 7.80 (d, J = 0.9 Hz, 1H), 7.74 (d, J = tetrahydrofuran-2- 3.9 Hz, 1H), 7.52 (d, J = 1.2 Hz, 1H), 7.43- ylmethyl]-1H- 7.37 (m, 1H), 7.23 (d, J = 3.9 Hz, 1H), 6.85 pyrazol-4- (dd, J = 7.1, 1.7 Hz, 1H), 4.48 (d, J = 5.7 Hz, yl}thiophene-2- 2H), 4.27-4.06 (m, 3H), 3.82-3.69 (m, 1H), carboxamide 3.69-3.58 (m, 1H), 2.01-1.86 (m, 1H), 1.86- 1.69 (m, 2H), 1.69-1.52 (m, 1H) 410 N-(imidazo[1,2- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (ESI(+)) a]pyridin-7- (t, J = 6.0 Hz, 1H), 8.49 (d, J = 6.7 Hz, 1H), m/e 408 ylmethyl)-5-[1- 8.24 (s, 1H), 7.89 (s, 1H), 7.82 (s, 1H), 7.75 (M + H)+ (tetrahydro-2H- (d, J = 3.9 Hz, 1H), 7.52 (d, J = 1.1 Hz, 1H), pyran-4-yl)-1H- 7.40 (s, 1H), 7.23 (d, J = 3.9 Hz, 1H), 6.85 pyrazol-4- (dd, J = 7.0, 1.7 Hz, 1H), 4.54-4.34 (m, 3H), yl]thiophene-2- 4.04-3.88 (m, 2H), 3.47 (td, J = 11.3, 3.9 Hz, carboxamide 2H), 2.06-1.86 (m, 4H) 465 N-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 9.05 (ESI(+)) a]pyridin-7- (t, J = 6.0 Hz, 1H), 8.50 (d, J = 7.0 Hz, 1H), m/e 436 ylmethyl)-5-{1-[(2- 8.03 (s, 1H), 7.90 (s, 1H), 7.80 (s, 1H), 7.75 (M + H)+ methyltetrahydro- (d, J = 3.8 Hz, 1H), 7.54 (d, J = 1.1 Hz, 1H), 2H-pyran-2- 7.41 (s, 1H), 7.25 (d, J = 3.9 Hz, 1H), 6.86 yl)methyl]-1H- (dd, J = 7.0, 1.6 Hz, 1H), 4.49 (d, J = 5.9 Hz, pyrazol-4- 2H), 4.24 (d, J = 14.1 Hz, 1H), 4.10 (d, J = yl}thiophene-2- 14.0 Hz, 1H), 3.81-3.67 (m, 1H), 3.65-3.52 carboxamide (m, 1H), 1.71-1.55 (m, 2H), 1.52-1.31 (m, 4H), 1.07 (s, 3H) 466 tert-butyl 4-[(4-{5- 1H NMR (300 MHz, DMSO-d6) δ ppm 9.02 (ESI(+)) [(imidazo[1,2- (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 7.1, 1.0 Hz, m/e 521 a]pyridin-7- 1H), 8.14 (d, J = 0.8 Hz, 1H), 7.89 (s, 1H), (M + H)+ ylmethyl)car- 7.81 (d, J = 0.9 Hz, 1H), 7.74 (d, J = 3.8 Hz, bamoyl]thiophen-2-yl}- 1H), 7.52 (d, J = 1.3 Hz, 1H), 7.40 (s, 1H), 1H-pyrazol-1- 7.22 (d, J = 3.9 Hz, 1H), 6.84 (dd, J = 7.1, 1.7 yl)methyl]piperidine- Hz, 1H), 4.48 (d, J = 5.7 Hz, 2H), 4.02 (d, J = 1-carboxylate 7.0 Hz, 2H), 3.92 (d, J = 13.2 Hz, 2H), 2.81- 2.57 (m, 2H), 2.16-1.90 (m, 1H), 1.56-1.42 (m, 2H), 1.38 (s, 9H), 1.22-0.94 (m, 2H) 475 5-[1- (ESI(+)) (cyclobutylmethyl)- m/e 392 1H-pyrazol-4-yl]- (M + H)+ N-(imidazo[1,2- a]pyridin-7- ylmethyl)thiophene- 2-carboxamide 476 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 392 ylmethyl)-5-[1- (M + H)+ (tetrahydrofuran-2- ylmethyl)-1H- pyrazol-4-yl]furan- 2-carboxamide 477 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 406 ylmethyl)-5-[1- (M + H)+ (tetrahydro-2H- pyran-2-ylmethyl)- 1H-pyrazol-4- yl]furan-2- carboxamide 478 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 392 ylmethyl)-5-[1- (M + H)+ (tetrahydrofuran-3- ylmethyl)-1H- pyrazol-4-yl]furan- 2-carboxamide 479 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 406 ylmethyl)-5-[1- (M + H)+ (tetrahydro-2H- pyran-3-ylmethyl)- 1H-pyrazol-4- yl]furan-2- carboxamide 480 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 406 ylmethyl)-5-[1- (M + H)+ (tetrahydro-2H- pyran-4-ylmethyl)- 1H-pyrazol-4- yl]furan-2- carboxamide 481 5-[1- (ESI(+)) (cyclobutylmethyl)- m/e 376 1H-pyrazol-4-yl]- (M + H)+ N-(imidazo[1,2- a]pyridin-7- ylmethyl)furan-2- carboxamide 482 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 392 ylmethyl)-5-{1-[(3- (M + H)+ methyloxetan-3- yl)methyl]-1H- pyrazol-4-yl}furan- 2-carboxamide 483 5-[1-(2-hydroxy-2- (ESI(+)) methylpropyl)-1H- m/e 380 pyrazol-4-yl]-N- (M + H)+ (imidazo[1,2- a]pyridin-7- ylmethyl)furan-2- carboxamide 883 5-[1-(2,2- (ESI(+)) dimethylpropyl)- m/e 394 1H-pyrazol-4-yl]- (M + H)+ N-(imidazo[1,2- a]pyridin-7- ylmethyl)thiophene- 2-carboxamide 884 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 472 ylmethyl)-5-[1- (M + H)+ (tricyclo[3.3.1.1~3, 7~]dec-1- ylmethyl)-1H- pyrazol-4- yl]thiophene-2- carboxamide 885 5-(1-benzyl-1H- (ESI(+)) pyrazol-4-yl)-N- m/e 414 (imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)thiophene- 2-carboxamide 886 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 474 ylmethyl)-5-[1-(2- (M + H)+ oxatricyclo[3.3.1.1~ 3,7~]dec-1- ylmethyl)-1H- pyrazol-4- yl]thiophene-2- carboxamide 1082 5-{1-[2,2-dimethyl- (ESI(+)) 3-(piperazin-1- m/e 478 yl)propyl]-1H- (M + H)+ pyrazol-4-yl}-N- (imidazo[1,2- a]pyridin-7- ylmethyl)thiophene- 2-carboxamide 1083 5-[1-(3-amino-2,2- (ESI(+)) dimethylpropyl)- m/e 409 1H-pyrazol-4-yl]- (M + H)+ N-(imidazo[1,2- a]pyridin-7- ylmethyl)thiophene- 2-carboxamide - The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-amine for 3-methylbutan-1-amine and 2-(4-nitrophenyl)acetic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 1B, substituting N-(imidazo[1,2-a]pyridin-6-yl)-2-(4-nitrophenyl)acetamide for N-isopentyl-4-nitrobenzamide.
- The title compound was prepared as described in Example 52A, substituting 2-(4-aminophenyl)-N-(imidazo[1,2-a]pyridin-6-yl)acetamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.71 (s, 1H), 9.83 (s, 1H), 9.55 (m, 1H), 8.38 (d, J=2.0 Hz, 1H), 8.08 (d, J=2.0 Hz, 1H), 7.96-7.88 (m, 1H), 7.80-7.73 (m, 1H), 7.58-7.51 (m, 2H), 7.29-7.23 (m, 2H), 3.67 (bs, 2H), 2.34-2.15 (m, 3H), 1.82-1.65 (m, 2H), 1.67-1.41 (m, 4H), 1.26-1.10 (m, 2H); MS (ESI(+)) m/e 377 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(tert-butoxycarbonylamino)benzoic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)phenylcarbamate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 4-amino-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide for 3-methylbutan-1-amine and 2-(tetrahydrofuran-2-yl)acetic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.14 (s, 1H), 8.93 (t, J=5.8 Hz, 1H), 8.48-8.45 (m, 1H), 7.95 (s, 1H), 7.88-7.82 (m, 2H), 7.71-7.64 (m, 2H), 7.53 (m, 7.55-7.48, 2H), 7.22 (dd, J=9.2, 1.7 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 4.23-4.12 (m, 1H), 3.82-3.72 (m, 1H), 3.66-3.56 (m, 1H), 2.59-2.44 (m, 2H), 2.07-1.95 (m, 1H), 1.92-1.77 (m, 2H), 1.60-1.47 (m, 1H); MS (ESI(+)) m/e 379 (M+H)+.
- The title compound was prepared as described in Example 77, substituting 2-(tetrahydrofuran-3-yl)acetic acid for 2-(tetrahydrofuran-2-yl)acetic acid in Example 77C. 1H NMR (500 MHz, DMSO-d6, Temp=90° C.) δ ppm 9.87 (bs, 1H), 8.65-8.59 (m, 1H), 8.42 (s, 1H), 7.87 (s, 1H), 7.84-7.79 (m, 2H), 7.66-7.61 (m, 2H), 7.52-7.45 (m, 2H), 7.21 (dd, J=9.2, 1.7 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 3.85-3.78 (m, 1H), 3.77-3.69 (m, 1H), 3.68-3.60 (m, 1H), 3.38-3.31 (m, 1H), 2.64-2.54 (m, 1H), 2.45-2.40 (m, 2H), 2.09-1.98 (m, 1H), 1.63-1.51 (m, 1H); MS (ESI(+)) m/e 379 (M+H)+.
- The title compound was prepared as described in Example 77, substituting 2-(tetrahydro-2H-pyran-4-yl)acetic acid for 2-(tetrahydrofuran-2-yl)acetic acid in Example 77C. 1H NMR (500 MHz, DMSO-d6, Temp=90° C.) δ ppm 9.84 (bs, 1H), 8.67-8.60 (m, 1H), 8.42 (s, 1H), 7.87 (s, 1H), 7.85-7.79 (m, 2H), 7.67-7.61 (m, 2H), 7.52-7.45 (m, 2H), 7.21 (dd, J=9.2, 1.7 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 3.85-3.77 (m, 2H), 3.35-3.26 (m, 2H), 2.28 (d, J=7.0 Hz, 2H), 2.07-1.96 (m, 1H), 1.65-1.57 (m, 2H), 1.31-1.22 (m, 2H); MS (ESI(+)) m/e 393 (M+H)+.
- The title compound was prepared as described in Example 77, substituting 2-morpholinoacetic acid for 2-(tetrahydrofuran-2-yl)acetic acid in Example 77C. 1H NMR (500 MHz, DMSO-d6, Temp=90° C.) δ ppm 9.70 (bs, 1H), 8.69-8.63 (m, 1H), 8.42 (s, 1H), 7.90-7.81 (m, 3H), 7.70-7.65 (m, 2H), 7.53-7.45 (m, 2H), 7.21 (dd, J=9.3, 1.7 Hz, 1H), 4.46 (d, J=5.8 Hz, 2H), 3.67-3.61 (m, 4H), 3.14 (s, 2H), 2.56-2.52 (m, 4H); MS (ESI(+)) m/e 394 (M+H)+.
- The title compound was prepared as described in Example 77, substituting 4-cyclopentylbutanoic acid for 2-(tetrahydrofuran-2-yl)acetic acid in Example 77C. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.10 (s, 1H), 8.92 (t, J=5.8 Hz, 1H), 8.46 (dd, J=1.9, 0.9 Hz, 1H), 7.95 (dd, J=1.2, 0.6 Hz, 1H), 7.87-7.81 (m, 2H), 7.70-7.64 (m, 2H), 7.55-7.49 (m, 2H), 7.22 (dd, J=9.2, 1.7 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 2.37-2.30 (m, 2H), 1.81-1.68 (m, 3H), 1.64-1.41 (m, 6H), 1.19-1.02 (m, 2H); MS (ESI(+)) m/e 391 (M+H)+.
- The title compound was prepared as described in Example 77, substituting 2-isopropoxyacetic acid for 2-(tetrahydrofuran-2-yl)acetic acid in Example 77C. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.78 (s, 1H), 8.95 (t, J=5.8 Hz, 1H), 8.49-8.44 (m, 1H), 7.97-7.93 (m, 1H), 7.89-7.83 (m, 2H), 7.78-7.72 (m, 2H), 7.56-7.50 (m, 2H), 7.22 (dd, J=9.2, 1.7 Hz, 1H), 4.46 (d, J=5.8 Hz, 2H), 4.04 (s, 2H), 3.75-3.64 (m, 1H), 1.17 (d, J=6.1 Hz, 6H); MS (ESI(+)) m/e 367 391 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-bromobenzoic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 4-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (t, J=5.9 Hz, 1H), 8.49-8.45 (m, 1H), 7.97-7.93 (m, 1H), 7.91-7.84 (m, 2H), 7.61-7.48 (m, 4H), 7.22 (dd, J=9.3, 1.7 Hz, 1H), 6.32-6.25 (m, 1H), 4.47 (d, J=5.8 Hz, 2H), 4.05-3.99 (m, 2H), 3.58-3.50 (m, 2H), 2.55-2.44 (m, 2H), 1.43 (s, 9H); MS (ESI(+)) m/e 433 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting (4-nitrophenyl)methanamine for 3-methylbutan-1-amine and imidazo[1,2-a]pyridine-6-carboxylic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 1B, substituting N-(4-nitrobenzyl)imidazo[1,2-a]pyridine-6-carboxamide for N-isopentyl-4-nitrobenzamide.
- The title compound was prepared as described in Example 1A, substituting N-(4-aminobenzyl)imidazo[1,2-a]pyridine-6-carboxamide for 3-methylbutan-1-amine and 2-cyclopentylacetic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.80 (s, 1H), 9.16-9.11 (m, 1H), 9.04 (t, J=5.9 Hz, 1H), 8.08-8.03 (m, 1H), 7.76-7.57 (m, 3H), 7.58-7.50 (m, 2H), 7.29-7.22 (m, 2H), 4.44 (d, J=5.8 Hz, 2H), 2.33-2.14 (m, 3H), 1.81-1.67 (m, 2H), 1.66-1.42 (m, 4H), 1.27-1.09 (m, 2H); MS (ESI(+)) m/e 377 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 2-bromothiazole-5-carboxamide for 4-nitrobenzoic acid.
- The title compound was prepared as in Example 53B, substituting 2,3,4,5-tetrahydro-1H-benzo[d]azepine for 4-cyanobenzylamine and 2-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiazole-5-carboxamide for 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.78 (t, J=5.8 Hz, 1H), 8.44 (s, 1H), 7.95 (s, 1H), 7.86 (s, 1H), 7.48-7.56 (m, 2H), 7.08-7.22 (m, 5H), 4.38 (d, J=5.9 Hz, 2H), 3.67-3.78 (m, 4H), 2.89-3.01 (m, 4H); MS (ESI(+)) m/e 402 (M+H)+.
- The title compound was prepared as in Example 85, substituting 3-phenylpyrrolidine for 2,3,4,5-tetrahydro-1H-benzo[d]azepine in Example 85B. 1H NMR (400 MHz, DMSO-d6) δ 8.75 (dd, J=5.8, 5.6 Hz, 1H), 8.44 (s, 1H), 7.95 (s, 1H), 7.86 (s, 1H), 7.56-7.50 (m, 2H), 7.35-7.31 (m, 2H), 7.29-7.21 (m, 2H), 7.18 (dd, J=8.4, 4.7 Hz, 1H), 4.45 (s, 1H), 4.38 (d, J=5.8 Hz, 2H), 3.92-3.83 (m, 2H), 3.62-3.45 (m, 2H), 2.68-2.62 (m, 1H), 2.42-2.30 (m, 1H), 2.20-2.07 (m, 1H). MS (ESI)(+)) m/e 404 (M+H)+.
- The title compound was prepared as in Example 85, substituting 3-methylbutan-1-amine for 2,3,4,5-tetrahydro-1H-benzo[d]azepine in Example 85B. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.67 (t, J=5.9 Hz, 1H), 8.42 (s, 1H), 8.08 (t, J=5.4 Hz, 1H), 7.94 (s, 1H), 7.71 (s, 1H), 7.49-7.55 (m, 2H), 7.16 (dd, J=9.3, 1.6 Hz, 1H), 4.36 (d, J=5.9 Hz, 2H), 3.17-3.26 (m, 2H), 1.61 (dq, J=6.7 Hz, 1H), 1.41 (q, J=7.0 Hz, 2H), 0.87 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 344 (M+H)+.
- The title compound was prepared as in Example 85, substituting isoindoline for 2,3,4,5-tetrahydro-1H-benzo[d]azepine in Example 85B. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.81 (t, J=5.9 Hz, 1H), 8.45 (s, 1H), 7.89-7.99 (m, 2H), 7.49-7.56 (m, 2H), 7.37-7.45 (m, 2H), 7.30-7.37 (m, 2H), 7.19 (dd, J=9.3, 1.5 Hz, 1H), 4.76 (s, 4H), 4.40 (d, J=5.7 Hz, 2H); MS (ESI(+)) m/e 376 (M+H)+.
- The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate for 4-amino-N-isopentylbenzamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.98-8.94 (m, 1H), 8.67 (s, 1H), 8.64 (s, 1H), 7.97-7.93 (m, 1H), 7.54-7.48 (m, 2H), 7.42-7.36 (m, 2H), 7.19-7.12 (m, 2H), 7.08 (dd, J=9.5, 2.1 Hz, 1H), 4.14-3.99 (m, 2H), 2.89-2.56 (m, 3H), 1.77-1.69 (m, 2H), 1.52-1.36 (m, 11H); MS (ESI(+)) m/e 436 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-(1,2,3,6-tetrahydropyridin-4-yl)benzamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6, Temp=90° C.) δ ppm 8.75-8.67 (m, 1H), 8.43 (s, 1H), 7.89-7.83 (m, 3H), 7.54-7.43 (m, 4H), 7.21 (dd, J=9.2, 1.7 Hz, 1H), 6.29-6.23 (m, 1H), 4.47 (d, J=5.8 Hz, 2H), 4.19-4.13 (m, 2H), 3.70 (t, J=5.7 Hz, 2H), 2.95-2.84 (m, 1H), 2.57-2.49 (m, 2H), 1.04 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 403 (M+H)+.
-
TABLE 7 The following Examples were prepared essentially as described in Example 90, substituting the appropriate carboxylic acid for isobutyric acid in Example 90B. Ex Name 1H NMR MS 91 4-[1-(2-hydroxy-2- (ESI(+)) methylpropanoyl)- m/e 419 1,2,3,6- (M + H)+ tetrahydropyridin-4- yl]-N-(imidazo[1,2- a]pyridin-6- ylmethyl)benzamide 92 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 460 ylmethyl)-4-[1- (M + H)+ (morpholin-4- ylacetyl)-1,2,3,6- tetrahydropyridin-4- yl]benzamide 93 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 459 ylmethyl)-4-[1- (M + H)+ (tetrahydro-2H- pyran-4-ylacetyl)- 1,2,3,6- tetrahydropyridin-4- yl]benzamide 94 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 445 ylmethyl)-4-[1- (M + H)+ (tetrahydrofuran-3- ylacetyl)-1,2,3,6- tetrahydropyridin-4- yl]benzamide 95 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 445 ylmethyl)-4-[1- (M + H)+ (tetrahydrofuran-2- ylacetyl)-1,2,3,6- tetrahydropyridin-4- yl]benzamide 96 N-(imidazo[1,2- (ESI(+)) a]pyridin-6- m/e 459 ylmethyl)-4-{1-[3- (M + H)+ (tetrahydrofuran-2- yl)propanoyl]- 1,2,3,6- tetrahydropyridin-4- yl}benzamide 97 4-[1- 1H NMR (300 MHz, methanol-d4) δ ppm 8.81- (ESI(+)) (cyclopentylacetyl)- 8.76 (m, 1H), 8.21 (m, 1H), 8.05-7.98 (m, m/e 443 1,2,3,6- 2H), 7.97-7.79 (m, 3H), 7.59-7.53 (m, 2H), (M + H)+ tetrahydropyridin-4- 6.31-6.23 (m, 1H), 4.74-4.65 (m, 2H), 4.29- yl]-N-(imidazo[1,2- 4.19 (m, 2H), 3.85-3.75 (m, 2H), 2.71- a]pyridin-6- 2.41 (m, 4H), 2.33-2.14 (m, 1H), 1.92-1.74 ylmethyl)benzamide (m, 2H), 1.76-1.49 (m, 4H), 1.32-1.13 (m, 2H) 98 N-(imidazo[1,2- 1H NMR (300 MHz, methanol-d4) δ ppm 8.81- (ESI(+)) a]pyridin-6- 8.76 (m, 1H), 8.21 (m, 1H), 8.05-7.98 (m, m/e 443 ylmethyl)-4-{1- 2H), 7.95-7.83 (m, 3H), 7.61-7.51 (m, 2H), (M + H)+ [(propan-2- 6.31-6.22 (m, 1H), 4.74-4.68 (m, 2H), 4.32- yloxy)acetyl]- 4.17 (m, 4H), 3.90-3.64 (m, 3H), 2.73- 1,2,3,6- 2.53 (m, 2H), 1.25-1.16 (m, 6H) tetrahydropyridin-4- yl}benzamide 99 N-(imidazo[1,2- 1H NMR (300 MHz, methanol-d4) δ ppm 8.81- (ESI(+)) a]pyridin-6- 8.77 (m, 1H), 8.22-8.20 (m, 1H), 8.02- m/e 431 ylmethyl)-4-[1- 7.99 (m, 2H), 7.97-7.82 (m, 3H), 7.59-7.53 (M + H)+ (tetrahydrofuran-2- (m, 2H), 6.31-6.23 (m, 1H), 4.82-4.74 (m, ylcarbonyl)-1,2,3,6- 1H), 4.70 (s, 2H), 4.40-4.11 (m, 2H), 4.01- tetrahydropyridin-4- 3.71 (m, 4H), 2.74-2.52 (m, 2H), 2.30-2.17 yl]benzamide (m, 1H), 2.17-1.84 (m, 3H) 100 N-(imidazo[1,2- 1H NMR (300 MHz, methanol-d4) δ ppm 8.81- (ESI(+)) a]pyridin-6- 8.77 (m, 1H), 8.24-8.17 (m, 1H), 8.05- m/e 431 ylmethyl)-4-[1- 7.97 (m, 2H), 7.97-7.82 (m, 3H), 7.59-7.53 (M + H)+ (tetrahydrofuran-3- (m, 2H), 6.31-6.25 (m, 1H), 4.72 (s, 2H), ylcarbonyl)-1,2,3,6- 4.35-4.21 (m, 2H), 4.06-3.93 (m, 1H), 3.95- tetrahydropyridin-4- 3.76 (m, 5H), 3.60-3.42 (m, 1H), 2.71- yl]benzamide 2.52 (m, 2H), 2.27-2.02 (m, 2H) 101 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm 8.81- (ESI(+)) a]pyridin-6- 8.78 (m, 1H), 8.23-8.19 (m, 1H), 8.05- m/e 828 ylmethyl)-4-[1- 7.98 (m, 2H), 7.93-7.84 (m, 3H), 7.59-7.53 (M + H)+ (tetrahydro-2H- (m, 2H), 6.31-6.25 (m, 1H), 4.70 (s, 2H), pyran-4- 4.36-4.30 (m, 1H), 4.25-4.19 (m, 1H), 4.02- ylcarbonyl)-1,2,3,6- 3.93 (m, 2H), 3.87-3.78 (m, 2H), 3.59- tetrahydropyridin-4- 3.46 (m, 2H), 3.10-2.92 (m, 1H), 2.70-2.53 yl]benzamide (m, 2H), 1.91-1.72 (m, 2H), 1.73-1.57 (m, 2H) 102 4-[1-(1,4-dioxan-2- 1H NMR (400 MHz, methanol-d4) δ ppm 8.79 (ESI(+)) ylcarbonyl)-1,2,3,6- (s, 1H), 8.23-8.20 (m, 1H), 8.04-7.99 (m, m/e 447 tetrahydropyridin-4- 2H), 7.93-7.84 (m, 3H), 7.59-7.53 (m, 2H), (M + H)+ yl]-N-(imidazo[1,2- 6.29-6.23 (m, 1H), 4.73-4.67 (m, 2H), 4.53- a]pyridin-6- 4.06 (m, 3H), 3.96-3.59 (m, 8H), 2.76- ylmethyl)benzamide 2.53 (m, 2H) 103 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm 8.79 (ESI(+)) a]pyridin-6- (s, 1H), 8.24-8.19 (m, 1H), 8.01 (m, 2H), m/e 449 ylmethyl)-4-{1-[(2- 7.97-7.82 (m, 3H), 7.59-7.53 (m, 2H), 6.31- (M + H)+ methoxyethoxy)acetyl]- 6.23 (m, 1H), 4.76-4.69 (m, 2H), 4.35- 1,2,3,6- 4.26 (m, 2H), 4.25-4.19 (m, 2H), 3.86-3.62 tetrahydropyridin-4- (m, 4H), 3.61-3.54 (m, 2H), 3.35 (s, 3H), yl}benzamide 2.72-2.54 (m, 2H) 104 4-(1-benzoyl- 1H NMR (400 MHz, DMSO-d6, Temp = 90° C.) (ESI(+)) 1,2,3,6- δ ppm 8.89-8.82 (m, 1H), 8.73 (s, 1H), 8.22 m/e 437 tetrahydropyridin-4- (d, J = 1.9 Hz, 1H), 7.96 (d, J = 1.9 Hz, 1H), (M + H)+ yl)-N-(imidazo[1,2- 7.90-7.75 (m, 4H), 7.56-7.49 (m, 2H), 7.49- a]pyridin-6- 7.37 (m, 5H), 6.27 (bs, 1H), 4.58 (d, J = 5.8 ylmethyl)benzamide Hz, 2H), 4.23-4.17 (m, 2H), 3.72-3.65 (m, 2H), 2.61-2.53 (m, 2H) 105 4-{1-[(4,4- 1H NMR (400 MHz, DMSO-d6, Temp = 90° C.) (ESI(+)) difluorocyclohexyl) δ ppm 8.90-8.83 (m, 1H), 8.74 (s, 1H), 8.22 m/e 479 carbonyl]-1,2,3,6- (d, J = 1.9 Hz, 1H), 7.97 (d, J = 1.9 Hz, 1H), (M + H)+ tetrahydropyridin-4- 7.90-7.75 (m, 4H), 7.54-7.48 (m, 2H), 6.30- yl}-N-(imidazo[1,2- 6.24 (m, 1H), 4.58 (d, J = 5.8 Hz, 2H), 4.21- a]pyridin-6- 4.15 (m, 2H), 3.77-3.69 (m, 2H), 2.91- ylmethyl)benzamide 2.79 (m, 1H), 2.58-2.51 (m, 2H), 2.12-2.00 (m, 2H), 2.00-1.59 (m, 6H) - The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 1-(imidazo[1,2-a]pyridin-6-yl)-3-(4-(piperidin-4-yl)phenyl)urea for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6, Temp=90° C.) δ ppm 8.86-8.81 (m, 1H), 8.41 (s, 1H), 8.38 (s, 1H), 7.86 (s, 1H), 7.50-7.42 (m, 2H), 7.40-7.34 (m, 2H), 7.18-7.12 (m, 2H), 7.12-7.06 (m, 1H), 4.41-4.18 (m, 2H), 2.95-2.64 (m, 4H), 1.87-1.78 (m, 2H), 1.56-1.38 (m, 2H), 1.03 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 406 (M+H)+.
- The title compound was prepared as in Example 85, substituting 1,2,3,4-tetrahydroisoquinoline for 2,3,4,5-tetrahydro-1H-benzo[d]azepine in Example 85B. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.81 (t, J=5.8 Hz, 1H), 8.47 (s, 1H), 7.98 (s, 1H), 7.89 (s, 1H), 7.48-7.63 (m, 2H), 7.13-7.32 (m, 5H), 4.65 (s, 2H), 4.39 (d, J=5.9 Hz, 2H), 3.73 (t, J=6.0 Hz, 2H), 2.94 (t, J=6.0 Hz, 2H); MS (ESI(+)) m/e 390 (M+H)+.
- The title compound was prepared as described in Example 106, substituting tetrahydro-2H-pyran-4-carboxylic acid for isobutyric acid in Example 106B. 1H NMR (400 MHz, methanol-d4) δ ppm 9.37-9.33 (m, 1H), 8.22-8.17 (m, 1H), 7.97 (d, J=2.1 Hz, 1H), 7.89-7.77 (m, 2H), 7.44-7.38 (m, 2H), 7.24-7.18 (m, 2H), 4.73-4.64 (m, 1H), 4.25-4.15 (m, 1H), 4.01-3.93 (m, 2H), 3.57-3.46 (m, 2H), 3.27-3.17 (m, 1H), 3.06-2.95 (m, 1H), 2.87-2.66 (m, 2H), 2.00-1.70 (m, 4H), 1.70-1.48 (m, 4H); MS (ESI(+)) m/e 448 (M+H)+.
- The title compound was prepared as described in Example 106, substituting 2-(tetrahydrofuran-3-yl)acetic acid for isobutyric acid in Example 106B. 1H NMR (400 MHz, methanol-d4) δ ppm 9.37-9.32 (m, 1H), 8.21-8.17 (m, 1H), 7.97 (d, J=2.1 Hz, 1H), 7.88-7.76 (m, 2H), 7.44-7.38 (m, 2H), 7.23-7.18 (m, 2H), 4.71-4.62 (m, 1H), 4.14-4.05 (m, 1H), 3.95-3.82 (m, 2H), 3.81-3.70 (m, 1H), 3.47-3.35 (m, 1H), 3.25-3.12 (m, 1H), 2.86-2.48 (m, 5H), 2.22-2.07 (m, 1H), 1.95-1.83 (m, 2H), 1.74-1.46 (m, 3H); MS (ESI(+)) m/e 448 (M+H)+.
- The title compound was prepared as described in Example 106, substituting 2-(tetrahydrofuran-2-yl)acetic acid for isobutyric acid in Example 106B. 1H NMR (400 MHz, methanol-d4) δ ppm 9.37-9.32 (m, 1H), 8.21-8.17 (m, 1H), 7.99-7.95 (m, 1H), 7.88-7.77 (m, 2H), 7.44-7.38 (m, 2H), 7.23-7.17 (m, 2H), 4.73-4.63 (m, 1H), 4.33-4.20 (m, 1H), 4.19-4.10 (m, 1H), 3.92-3.83 (m, 1H), 3.79-3.69 (m, 1H), 3.26-3.14 (m, 1H), 2.87-2.65 (m, 3H), 2.63-2.47 (m, 1H), 2.19-2.06 (m, 1H), 2.01-1.81 (m, 4H), 1.77-1.50 (m, 3H); MS (ESI(+)) m/e 448 (M+H)+.
- The title compound was prepared as described in Example 106, substituting benzoic acid for isobutyric acid in Example 106B. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.87-8.81 (m, 1H), 8.38 (bs, 1H), 8.38 (bs, 1H), 7.86 (s, 1H), 7.51-7.34 (m, 9H), 7.21-7.14 (m, 2H), 7.09 (dd, J=9.5, 2.0 Hz, 1H), 4.34-3.97 (m, 2H), 3.08-2.95 (m, 2H), 2.83-2.71 (m, 1H), 1.85-1.77 (m, 2H), 1.66-1.50 (m, 2H); MS (ESI(+)) m/e 440 (M+H)+.
- The title compound was prepared as described in Example 106, substituting tetrahydrofuran-2-carboxylic acid for isobutyric acid in Example 106B. 1H NMR (400 MHz, methanol-d4) δ ppm 9.38-9.33 (m, 1H), 8.21-8.16 (m, 1H), 8.00-7.95 (m, 1H), 7.88-7.77 (m, 2H), 7.44-7.38 (m, 2H), 7.23-7.17 (m, 2H), 4.83-4.73 (m, 1H), 4.69-4.60 (m, 1H), 4.22-4.11 (m, 1H), 4.01-3.90 (m, 1H), 3.91-3.82 (m, 1H), 3.26-3.12 (m, 1H), 2.87-2.68 (m, 2H), 2.31-2.14 (m, 1H), 2.12-1.75 (m, 5H), 1.77-1.50 (m, 2H); MS (ESI(+)) m/e 434 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.40 (s, 1H), 7.86-7.79 (m, 3H), 7.52 (t, J=5.4 Hz, 2H), 7.34 (dd, J=9.3, 1.7 Hz, 1H), 7.06-6.99 (m, 2H), 4.72-4.60 (m, 1H), 4.56 (s, 2H), 3.77-3.65 (m, 2H), 3.41-3.30 (m, 2H), 2.03-1.90 (m, 2H), 1.76-1.59 (m, 2H), 1.46 (s, 9H); MS (ESI(+)) m/e 451 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 2-bromothiazole-5-carboxylic acid for 4-nitrobenzoic acid.
- The title compound was prepared as in Example 53B, substituting (tetrahydrofuran-2-yl)methanamine for 4-cyanobenzylamine and 2-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiazole-5-carboxamide for 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide.
- The title compound was prepared as described in Example 1C, substituting 2-isopropoxyethanamine for 4-amino-N-isopentylbenzamide and N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-((tetrahydrofuran-2-yl)methylamino)thiazole-5-carboxamide for imidazo[1,2-a]pyridin-6-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.52 (s, 1H), 8.21 (d, J=9.0 Hz, 1H), 7.96 (s, 1H), 7.89 (d, J=1.5 Hz, 1H), 7.86-7.80 (m, 1H), 7.78 (d, J=9.5 Hz, 1H), 7.73 (s, 1H), 6.96-6.86 (m, 1H), 4.74-4.60 (m, 2H), 4.50-4.38 (m, 1H), 4.26 (ddd, J=4.4, 2.2, 0.6 Hz, 1H), 4.07-3.90 (m, 2H), 3.85-3.74 (m, 1H), 3.63 (dd, J=12.2, 6.1 Hz, 1H), 3.60-3.53 (m, 2H), 3.53-3.41 (m, 2H), 1.95 (dd, J=7.8, 6.9 Hz, 3H), 1.63-1.56 (m, 1H), 1.18 (dd, J=6.1, 1.2 Hz, 6H); (APCI(+)) m/e 487 (M+H)+.
-
TABLE 8 The following Examples were prepared essentially as described in Example 115, substituting the appropriate amine in Example 115B and the appropriate amine for 2-isopropoxyethanamine in Example 115C. Ex Name 1H NMR MS 138 N-(imidazo[1,2- 1H NMR (400 MHz, CDCl3) δ ppm 8.09 (d, (APCI(+)) a]pyridin-7- J = 7.0 Hz, 1H), 7.86 (d, J = 14.0 Hz, 2H), m/e 459 ylmethyl)-2-{[(2- 7.62 (d, J = 0.8 Hz, 1H), 7.54 (d, J = 9.1 Hz, (M + H)+ methoxyethyl)carbam- 2H), 6.84 (dd, J = 7.0, 1.4 Hz, 1H), 6.27 (t, oyl](tetrahydrofuran- J = 5.8 Hz, 1H), 4.63 (d, J = 6.0 Hz, 2H), 2-ylmethyl)amino}- 4.44 (d, J = 14.3 Hz, 1H), 4.29 (q, J = 7.3 1,3-thiazole-5- Hz, 1H), 4.05 (dd, J = 15.4, 7.2 Hz, 1H), carboxamide 3.92 (dd, J = 15.2, 7.2 Hz, 1H), 3.86-3.72 (m, 1H), 3.58-3.51 (m, 2H), 3.48 (dd, J = 9.2, 3.8 Hz, 3H), 3.39 (s, 3H), 2.14 (dt, J = 12.4, 6.3 Hz, 1H), 2.05-1.86 (m, 2H) 141 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm (APCI(+)) a]pyridin-6- 8.78 (s, 1H), 8.22 (d, J = 2.1 Hz, 1H), 8.03 m/e 459 ylmethyl)-2-{[(2- (d, J = 2.1 Hz, 1H), 7.99 (d, J = 9.8 Hz, (M + H)+ methoxyethyl)carbam- 2H), 7.91 (d, J = 9.3 Hz, 1H), 4.65 (s, 2H), oyl](tetrahydrofuran- 4.24 (dd, J = 15.2, 7.6 Hz, 1H), 4.12 (dd, J = 3-ylmethyl)amino}- 15.2, 7.9 Hz, 1H), 3.93 (td, J = 8.1, 5.8 1,3-thiazole-5- Hz, 1H), 3.79-3.67 (m, 2H), 3.60 (dd, J = carboxamide 8.7, 5.2 Hz, 1H), 3.55-3.45 (m, 4H), 3.36 (s, 3H), 2.85-2.75 (m, 1H), 2.00 (td, J = 13.4, 7.8 Hz, 1H), 1.72 (dt, J = 20.1, 6.3 Hz, 1H) 151 N-(imidazo[1,2- 1H NMR (500 MHz, methanol-d4) δ ppm (APCI(+)) a]pyridin-6- 8.77 (s, 1H), 8.21 (d, J = 2.0 Hz, 1H), 8.02 m/e 473 ylmethyl)-2-{[(2- (d, J = 2.1 Hz, 1H), 7.99 (dd, J = 9.3, 1.4 (M + H)+ methoxyethyl)carbam- Hz, 1H), 7.97 (s, 1H), 7.90 (d, J = 9.3 Hz, oyl](tetrahydro- 1H), 4.65 (s, 2H), 4.07 (d, J = 7.6 Hz, 2H), 2H-pyran-4- 3.92 (dd, J = 11.5, 3.0 Hz, 2H), 3.52 (dd, J = ylmethyl)amino}- 8.3, 3.1 Hz, 2H), 3.47 (dd, J = 8.1, 3.0 Hz, 1,3-thiazole-5- 2H), 3.36 (s, 3H), 3.36-3.32 (m, 2H), 2.14 carboxamide (ddd, J = 15.4, 7.7, 3.8 Hz, 1H), 1.54 (d, J = 11.2 Hz, 2H), 1.42 (qd, J = 12.1, 4.4 Hz, 2H) 152 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm (APCI(+)) a]pyridin-6- 8.78 (s, 1H), 8.22 (d, J = 2.1 Hz, 1H), 8.03 m/e 501 ylmethyl)-2-[{[2- (d, J = 2.1 Hz, 1H), 8.01-7.97 (m, 2H), (M + H)+ (propan-2- 7.91 (d, J = 9.3 Hz, 1H), 4.65 (s, 2H), 4.06 yloxy)ethyl]carbam- (d, J = 7.6 Hz, 2H), 3.92 (dd, J = 11.4, 3.0 oyl}(tetrahydro-2H- Hz, 2H), 3.63 (dt, J = 12.2, 6.1 Hz, 1H), pyran-4- 3.57 (dd, J = 10.1, 4.5 Hz, 2H), 3.45 (t, J = ylmethyl)amino]- 5.5 Hz, 2H), 3.35 (dd, J = 11.6, 1.7 Hz, 2H), 1,3-thiazole-5- 2.16 (ddd, J = 11.4, 7.6, 3.8 Hz, 1H), 1.55 carboxamide (dd, J = 12.6, 1.5 Hz, 2H), 1.42 (qd, J = 12.1, 4.4 Hz, 2H), 1.16 (d, J = 6.1 Hz, 6H) 153 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm (APCI(+)) a]pyridin-6- 8.70 (s, 1H), 8.14 (d, J = 2.1 Hz, 1H), 7.95 m/e 459 ylmethyl)-2-{[(2- (d, J = 2.2 Hz, 1H), 7.91 (dd, J = 9.4, 1.5 (M + H)+ methoxyethyl)carbam- Hz, 1H), 7.88 (s, 1H), 7.82 (d, J = 9.3 Hz, oyl][(2R)- 1H), 4.57 (s, 2H), 4.33 (dd, J = 15.4, 1.8 tetrahydrofuran-2- Hz, 1H), 4.17 (dd, J = 11.3, 4.9 Hz, 1H), ylmethyl]amino}- 4.00 (dd, J = 15.4, 7.7 Hz, 1H), 3.86 (dd, J = 1,3-thiazole-5- 15.2, 7.0 Hz, 1H), 3.71 (td, J = 7.8, 5.8 carboxamide Hz, 1H), 3.52-3.39 (m, 2H), 3.38-3.32 (m, 2H), 3.30 (s, 3H), 2.11-1.95 (m, 1H), 1.95-1.77 (m, 2H), 1.66-1.48 (m, 1H), 0.99-0.87 (m, 1H) 154 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm (APCI(+)) a]pyridin-6- 8.77 (s, 1H), 8.21 (d, J = 2.1 Hz, 1H), 8.02 m/e 487 ylmethyl)-2-({[2- (d, J = 2.1 Hz, 1H), 7.98 (dd, J = 9.4, 1.2 (M + H)+ (propan-2- Hz, 1H), 7.96 (s, 1H), 7.90 (d, J = 9.3 Hz, yloxy)ethyl]carbam- 1H), 4.64 (s, 2H), 4.41 (dd, J = 15.4, 1.6 oyl}[(2R)- Hz, 1H), 4.29-4.21 (m, 1H), 4.07 (dd, J = tetrahydrofuran-2- 15.4, 7.6 Hz, 1H), 3.96 (dd, J = 15.0, 7.1 ylmethyl]amino)- Hz, 1H), 3.77 (dd, J = 14.0, 7.7 Hz, 1H), 1,3-thiazole-5- 3.64 (dt, J = 12.2, 6.1 Hz, 1H), 3.57 (t, J = carboxamide 5.0 Hz, 2H), 3.41 (t, J = 5.3 Hz, 2H), 2.15- 2.03 (m, 1H), 2.00-1.87 (m, 2H), 1.64 (dq, J = 12.4, 8.2 Hz, 1H), 1.16 (d, J = 6.1 Hz, 6H) 155 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm (APCI(+)) a]pyridin-6- 8.78 (s, 1H), 8.21 (d, J = 2.1 Hz, 1H), 8.03 m/e 459 ylmethyl)-2-{[(2- (d, J = 2.1 Hz, 1H), 8.01-7.97 (m, 1H), (M + H)+ methoxyethyl)carbam- 7.96 (s, 1H), 7.90 (d, J = 9.3 Hz, 1H), 4.64 oyl][(2S)- (s, 2H), 4.41 (d, J = 15.4 Hz, 1H), 4.26 (q, J = tetrahydrofuran-2- 6.4 Hz, 1H), 4.08 (dd, J = 15.4, 7.7 Hz, ylmethyl]amino}- 1H), 3.94 (dd, J = 15.1, 7.1 Hz, 1H), 3.79 1,3-thiazole-5- (dd, J = 13.7, 7.7 Hz, 1H), 3.53 (dt, J = 7.4, carboxamide 4.5 Hz, 2H), 3.43 (t, J = 5.2 Hz, 2H), 3.38 (s, 3H), 2.11 (td, J = 12.3, 7.2 Hz, 1H), 2.01- 1.85 (m, 2H), 1.65 (dq, J = 12.2, 8.2 Hz, 1H) 156 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm (APCI(+)) a]pyridin-6- 8.78 (s, 1H), 8.22 (d, J = 2.1 Hz, 1H), 8.03 m/e 487 ylmethyl)-2-({[2- (d, J = 2.1 Hz, 1H), 7.99 (dd, J = 9.3, 1.4 (M + H)+ (propan-2- Hz, 1H), 7.96 (s, 1H), 7.91 (d, J = 9.3 Hz, yloxy)ethyl]carbam- 1H), 4.65 (s, 2H), 4.41 (dd, J = 15.4, 1.8 oyl}[(2S)- Hz, 1H), 4.31-4.22 (m, 1H), 4.08 (dd, J = tetrahydrofuran-2- 15.4, 7.6 Hz, 1H), 3.96 (dd, J = 15.1, 7.0 ylmethyl]amino)- Hz, 1H), 3.78 (dd, J = 14.0, 7.7 Hz, 1H), 1,3-thiazole-5- 3.65 (dt, J = 12.1, 6.1 Hz, 1H), 3.57 (t, J = carboxamide 4.9 Hz, 2H), 3.41 (t, J = 5.3 Hz, 2H), 2.11 (td, J = 12.2, 7.1 Hz, 1H), 2.01-1.85 (m, 2H), 1.65 (dq, J = 12.3, 8.2 Hz, 1H), 1.17 (d, J = 6.1 Hz, 6H) 157 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm (APCI(+)) a]pyridin-6- 8.78 (s, 1H), 8.21 (d, J = 2.0 Hz, 1H), 8.03 m/e 487 ylmethyl)-2-[{[2- (d, J = 2.1 Hz, 1H), 7.99 (d, J = 11.6 Hz, (M + H)+ (propan-2- 2H), 7.90 (d, J = 9.4 Hz, 1H), 4.65 (d, J = yloxy)ethyl]carbam- 3.9 Hz, 2H), 4.24 (dd, J = 15.2, 7.6 Hz, 1H), oyl}(tetrahydrofuran- 4.12 (dd, J = 15.1, 8.0 Hz, 1H), 3.94 (td, J = 3-ylmethyl)amino]- 8.1, 5.7 Hz, 1H), 3.79-3.67 (m, 2H), 3.63 1,3-thiazole-5- (dt, J = 8.2, 4.7 Hz, 2H), 3.57 (t, J = 5.8 Hz, carboxamide 2H), 3.51-3.41 (m, 2H), 2.89-2.76 (m, 1H), 2.00 (td, J = 13.3, 7.9 Hz, 1H), 1.73 (dt, J = 20.3, 6.4 Hz, 1H), 1.15 (d, J = 6.1 Hz, 6H) - The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 2-bromothiazole-5-carboxylic acid for 4-nitrobenzoic acid.
- The title compound was prepared as in Example 53B, substituting 4-(tetrahydrofuran-3-yl)oxazolidin-2-one for 4-cyanobenzylamine and 2-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiazole-5-carboxamide for 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide. 1H NMR (400 MHz, methanol-d4) δ 8.79 (s, 1H), 8.22 (d, J=1.9 Hz, 1H), 8.03 (s, 2H), 8.01-7.97 (m, 1H), 7.91 (d, J=9.5 Hz, 1H), 4.98-4.92 (m, 1H), 4.64 (dt, J=8.6, 4.5 Hz, 3H), 4.57-4.49 (m, 1H), 3.97 (td, J=8.5, 3.9 Hz, 1H), 3.81-3.71 (m, 1H), 3.71-3.59 (m, 2H), 2.26-2.02 (m, 1H), 1.96-1.85 (m, 1H), 1.78-1.65 (m, 1H); (APCI(+)) m/e 414 (M+H)+.
-
TABLE 9 The following Examples were prepared essentially as described in Example 116, substituting the appropriate amine in Example 116A and the appropriate amine in Example 116B. Ex Name 1H NMR MS 122 N-(imidazo[1,2- (ESI(+)) a]pyridin-6-ylmethyl)-2- m/e 420 (2-oxo-5-phenyl-1,3- (M + H)+ oxazolidin-3-yl)-1,3- thiazole-5-carboxamide 158 2-[5-(4-chlorophenyl)- (ESI(+)) 2-oxo-1,3-oxazolidin-3- m/e 454 yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-6-ylmethyl)- 1,3-thiazole-5- carboxamide 181 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ (APCI(+)) a]pyridin-7-ylmethyl)-2- ppm 8.39 (d, J = 7.0 Hz, 1H), 8.04 (s, m/e 386 [(4R)-2-oxo-4-(propan- 1H), 7.80 (s, 1H), 7.53 (s, 1H), 7.45 (s, (M + H)+ 2-yl)-1,3-oxazolidin-3- 1H), 6.97-6.87 (m, 1H), 4.75 (dt, J = yl]-1,3-thiazole-5- 7.7, 3.8 Hz, 1H), 4.52 (dd, J = 9.5, 6.3 carboxamide Hz, 2H), 2.85-2.65 (m, 1H), 0.99 (d, J = 7.1 Hz, 3H), 0.84 (d, J = 6.9 Hz, 3H) 185 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ (APCI(+)) a]pyridin-7-ylmethyl)-2- ppm 9.26 (t, J = 5.5 Hz, 1H), 8.75 (d, J = m/e 386 [(4S)-2-oxo-4-(propan- 7.0 Hz, 1H), 8.18 (d, J = 2.1 Hz, 1H), (M + H)+ 2-yl)-1,3-oxazolidin-3- 8.07 (s, 1H), 8.00 (d, J = 2.1 Hz, 1H), yl]-1,3-thiazole-5- 7.81 (s, 1H), 7.48 (d, J = 7.0 Hz, 1H), carboxamide 4.77 (dd, J = 7.7, 3.9 Hz, 1H), 4.55 (dd, J = 10.7, 6.3 Hz, 2H), 2.76 (qd, J = 10.6, 7.1 Hz, 1H), 1.00 (d, J = 7.1 Hz, 3H), 0.84 (d, J = 6.9 Hz, 3H) 187 2-{(4R)-4- 1H NMR (400 MHz, methanol-d4) δ (APCI(+)) [(benzyloxy)methyl]-2- ppm 8.40 (d, J = 7.0 Hz, 1H), 7.91 (s, m/e 464 oxo-1,3-oxazolidin-3- 1H), 7.80 (s, 1H), 7.53 (s, 1H), 7.46 (s, (M + H)+ yl}-N-(imidazo[1,2- 1H), 7.20 (ddd, J = 15.4, 11.1, 5.1 Hz, a]pyridin-7-ylmethyl)- 5H), 6.93 (dd, J = 7.0, 1.3 Hz, 1H), 4.85 1,3-thiazole-5- (dd, J = 6.1, 2.6 Hz, 1H), 4.67-4.52 carboxamide (m, 5H), 4.41 (d, J = 12.2 Hz, 1H), 4.12 (dd, J = 10.2, 3.2 Hz, 1H), 3.63 (dd, J = 10.2, 1.6 Hz, 1H) 188 2-{(4S)-4- 1H NMR (400 MHz, methanol-d4) δ (APCI(+)) [(benzyloxy)methyl]-2- ppm 8.35 (d, J = 7.0 Hz, 1H), 7.87 (s, m/e 464 oxo-1,3-oxazolidin-3- 1H), 7.75 (s, 1H), 7.48 (s, 1H), 7.42 (s, (M + H)+ yl}-N-(imidazo[1,2- 1H), 7.16 (ddd, J = 19.3, 11.3, 5.0 Hz, a]pyridin-7-ylmethyl)- 5H), 6.88 (dd, J = 7.0, 1.3 Hz, 1H), 4.83- 1,3-thiazole-5- 4.75 (m, 1H), 4.62-4.47 (m, 5H), carboxamide 4.36 (d, J = 12.2 Hz, 1H), 4.07 (dd, J = 10.2, 3.2 Hz, 1H), 3.59 (dd, J = 10.2, 1.6 Hz, 1H) 218 2-{5- 1H NMR (400 MHz, methanol-d4) δ (APCI(+)) [(benzyloxy)methyl]-2- ppm 8.39 (d, J = 7.0 Hz, 1H), 8.03 (s, m/e 464 oxo-1,3-oxazolidin-3- 1H), 7.79 (s, 1H), 7.53 (s, 1H), 7.45 (s, (M + H)+ yl}-N-(imidazo[1,2- 1H), 7.36-7.18 (m, 5H), 6.92 (d, J = a]pyridin-7-ylmethyl)- 5.6 Hz, 1H), 5.02-4.99 (m, 2H), 4.59 1,3-thiazole-5- (d, J = 2.3 Hz, 6H), 3.76 (ddd, J = 14.8, carboxamide 11.2, 3.2 Hz, 1H) 244 2-[(2S)-2- 1H NMR (400 MHz, methanol-d4) δ (APCI(+)) (hydroxymethyl)-5- ppm 9.25 (t, J = 5.7 Hz, 1H), 8.75 (d, J = m/e 372 oxopyrrolidin-1-yl]-N- 7.0 Hz, 1H), 8.18 (d, J = 1.9 Hz, 1H), (M + H)+ (imidazo[1,2-a]pyridin- 8.10 (s, 1H), 8.00 (d, J= 2.1 Hz, 1H), 7-ylmethyl)-1,3- 7.81 (s, 1H), 7.48 (dd, J = 7.1, 1.3 Hz, thiazole-5-carboxamide 1H), 4.75-4.69 (m, 3H), 4.17 (dd, J = 11.7, 3.4 Hz, 1H), 3.75 (dd, J = 11.7, 2.2 Hz, 1H), 2.88 (dt, J = 17.8, 10.1 Hz, 1H), 2.57 (ddd, J = 17.7, 10.1, 2.3 Hz, 1H), 2.48-2.33 (m, 1H), 2.33-2.18 (m, 1H) 245 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ (APCI(+)) a]pyridin-7-ylmethyl)-2- ppm 8.75 (d, J = 7.0 Hz, 1H), 8.18 (d, J = m/e 358 [(4R)-4-methyl-2-oxo- 2.0 Hz, 1H), 8.07 (s, 1H), 8.00 (t, J = (M + H)+ 1,3-oxazolidin-3-yl]- 2.4 Hz, 1H), 7.81 (s, 1H), 7.48 (dd, J = 1,3-thiazole-5- 7.0, 1.4 Hz, 1H), 4.87-4.78 (m, 1H), carboxamide 4.73 (s, 2H), 4.69 (t, J = 8.5 Hz, 1H), 4.25 (dd, J = 8.7, 3.9 Hz, 1H), 1.57 (d, J = 6.3 Hz, 3H) 249 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ (APCI(+)) a]pyridin-7-ylmethyl)-2- ppm 9.26 (t, J = 5.9 Hz, 1H), 8.75 (d, J = m/e 416 {2-oxo-5-[(propan-2- 7.0 Hz, 1H), 8.18 (d, J = 2.0 Hz, 1H), (M + H)+ yloxy)methyl]-1,3- 8.06 (s, 1H), 8.00 (d, J = 2.1 Hz, 1H), oxazolidin-3-yl}-1,3- 7.81 (s, 1H), 7.48 (d, J = 7.0 Hz, 1H), thiazole-5-carboxamide 4.98 (ddd, J = 9.1, 5.8, 2.9 Hz, 1H), 4.73 (s, 2H), 4.31 (t, J = 9.5 Hz, 1H), 4.14 (dd, J = 9.9, 5.6 Hz, 1H), 3.78 (dd, J = 11.2, 2.9 Hz, 1H), 3.73-3.60 (m, 2H), 1.13 (d, J = 6.1 Hz, 6H) 251 2-[5-(hydroxymethyl)- 1H NMR (400 MHz, DMSO-d6) δ ppm (APCI(+)) 2-oxo-1,3-oxazolidin-3- 9.17 (t, J = 6.2 Hz, 1H), 8.50 (d, J = 6.9 m/e 374 yl]-N-(imidazo[1,2- Hz, 1H), 8.14 (s, 1H), 7.90 (s, 1H), 7.53 (M + H)+ a]pyridin-7-ylmethyl)- (s, 1H), 7.41 (s, 1H), 6.85 (d, J = 6.9 1,3-thiazole-5- Hz, 1H), 5.29 (t, J = 5.6 Hz, 1H), 4.93- carboxamide 4.84 (m, 1H), 4.47 (d, J = 5.8 Hz, 2H), 4.24 (t, J = 9.4 Hz, 1H), 4.00 (dd, J = 9.8, 5.8 Hz, 1H), 3.76-3.66 (m, 1H), 3.66-3.56 (m, 1H) 255 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ (APCI(+)) a]pyridin-7-ylmethyl)-2- 8.40 (d, J = 7.0 Hz, 1H), 8.04 (s, 1H), m/e 416 {(5S)-2-oxo-5-[(propan- 7.80 (s, 1H), 7.53 (s, 1H), 7.45 (s, 1H), (M + H)+ 2-yloxy)methyl]-1,3- 6.92 (d, J = 6.3 Hz, 1H), 5.01-4.94 (m, oxazolidin-3-yl}-1,3- 1H), 4.59 (s, 2H), 4.31 (t, J = 9.5 Hz, thiazole-5-carboxamide 1H), 4.13 (dd, J = 9.9, 5.6 Hz, 1H), 3.77 (dd, J = 11.2, 3.0 Hz, 1H), 3.72-3.58 (m, 2H), 1.13 (d, J = 6.1 Hz, 6H) 256 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ (APCI(+)) a]pyridin-7-ylmethyl)-2- ppm 8.40 (d, J = 7.0 Hz, 1H), 8.04 (s, m/e 416 {(5R)-2-oxo-5-[(propan- 1H), 7.80 (s, 1H), 7.53 (s, 1H), 7.45 (s, (M + H)+ 2-yloxy)methyl]-1,3- 1H), 6.92 (d, J = 7.0 Hz, 1H), 5.03- oxazolidin-3-yl}-1,3- 4.95 (m, 1H), 4.59 (s, 2H), 4.31 (t, J = thiazole-5-carboxamide 9.5 Hz, 1H), 4.13 (dd, J = 9.9, 5.7 Hz, 1H), 3.77 (dd, J = 11.2, 3.0 Hz, 1H), 3.71-3.58 (m, 2H), 1.13 (d, J = 6.1 Hz, 6H) - The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.09 (s, 1H), 9.00-8.93 (m, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90-7.82 (m, 3H), 7.71-7.65 (m, 2H), 7.51 (d, J=1.2 Hz, 1H), 7.40-7.35 (m, 1H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 2.37-2.31 (m, 2H), 2.31-2.16 (m, 1H), 1.81-1.68 (m, 2H), 1.67-1.44 (m, 4H), 1.26-1.10 (m, 2H); MS (ESI(+)) m/e 377 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 4-nitroaniline for 3-methylbutan-1-amine and 2-cyclopentylacetic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 1B, substituting 2-cyclopentyl-N-(4-nitrophenyl)acetamide for N-isopentyl-4-nitrobenzamide.
- The title compound was prepared as described in Example 1C, substituting N-(4-aminophenyl)-2-cyclopentylacetamide for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1H NMR (400 MHz, methanol-d4) δ ppm 8.76-8.69 (m, 1H), 8.16 (dd, J=2.2, 0.8 Hz, 1H), 7.98 (d, J=2.2 Hz, 1H), 7.81-7.77 (m, 1H), 7.49-7.41 (m, 3H), 7.36-7.30 (m, 2H), 4.59 (s, 2H), 2.37-2.24 (m, 3H), 1.90-1.77 (m, 2H), 1.75-1.52 (m, 4H), 1.32-1.18 (m, 2H); MS (ESI(+)) m/e 392 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 4-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide for 4-bromoaniline. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.18 (t, J=5.7 Hz, 1H), 8.75 (s, 1H), 8.28 (s, 2H), 8.02 (d, J=1.5 Hz, 1H), 7.97 (s, 1H), 7.89 (d, J=8.5 Hz, 2H), 7.83-7.88 (m, 1H), 7.74-7.80 (m, 1H), 7.69 (d, J=8.3 Hz, 2H), 4.56 (d, J=5.7 Hz, 2H), 3.92 (d, J=7.2 Hz, 2H), 2.13 (dq, J=13.6, 6.8 Hz, 1H), 0.85 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 374 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting 3-methylbutanoyl chloride for 2-cyclopentylacetyl chloride and methyl 2-aminothiazole-5-carboxylate for methyl 4-aminobenzoate.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 2-(3-methylbutanamido)thiazole-5-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.31 (s, 1H), 9.05 (t, J=5.7 Hz, 1H), 8.54 (s, 1H), 7.97-8.11 (m, 2H), 7.56-7.71 (m, 2H), 7.34 (d, J=9.2 Hz, 1H), 4.44 (d, J=5.7 Hz, 2H), 2.33 (d, J=7.2 Hz, 2H), 2.07 (dq, J=13.6, 6.7, 6.6 Hz, 1H), 0.90 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 358 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)benzoic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)phenoxy)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-(piperidin-4-yloxy)benzamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.79-8.74 (m, 1H), 8.23-8.19 (m, 1H), 8.04-7.97 (m, 2H), 7.94-7.81 (m, 3H), 7.09-7.03 (m, 2H), 4.81-4.72 (m, 1H), 4.69 (s, 2H), 3.91-3.77 (m, 2H), 3.62-3.48 (m, 2H), 3.04-2.92 (m, 1H), 2.12-1.86 (m, 2H), 1.87-1.61 (m, 2H), 1.11 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 421 (M+H)+.
-
TABLE 10 The following Examples were prepared essentially as described in Example 159, substituting the appropriate amine in Example 159A and the appropriate carboxylic acid in Example 159C. Ex Name 1H NMR MS 160 4-[(1- 1H NMR (400 MHz, methanol-d4) δ ppm 8.80- (ESI(+)) acetylpiperidin-4- 8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7 Hz, 1H), m/e 393 yl)oxy]-N- 8.04-7.97 (m, 2H), 7.94-7.79 (m, 3H), 7.09- (M + H)+ (imidazo[1,2- 7.03 (m, 2H), 4.78-4.70 (m, 1H), 4.69 (s, 2H), a]pyridin-6- 3.88-3.69 (m, 2H), 3.59-3.45 (m, 2H), 2.12 ylmethyl)benzamide (s, 3H), 2.09-1.91 (m, 2H), 1.86-1.63 (m, 2H) 161 4-{[1- 1H NMR (400 MHz, methanol-d4) δ ppm 8.79- (ESI(+)) (cyclopropylcar- 8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7 Hz, 1H), m/e 419 bonyl)piperidin-4- 8.04-7.97 (m, 2H), 7.93-7.82 (m, 3H), 7.10- (M + H)+ yl]oxy}-N- 7.04 (m, 2H), 4.81-4.73 (m, 1H), 4.69 (s, 2H), (imidazo[1,2- 4.07-3.97 (m, 1H), 3.92-3.81 (m, 1H), 3.78- a]pyridin-6- 3.67 (m, 1H), 3.57-3.48 (m, 1H), 2.13-1.92 ylmethyl)benzamide (m, 3H), 1.88-1.65 (m, 2H), 0.91-0.78 (m, 4H) 162 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm 8.77 (ESI(+)) a]pyridin-6- (m, 1H), 8.23-8.19 (m, 1H), 8.04-7.97 (m, m/e 463 ylmethyl)-4-{[1- 2H), 7.94-7.82 (m, 3H), 7.09-7.03 (m, 2H), (M + H)+ (tetrahydro-2H- 4.75 (m, 1H), 4.69 (s, 2H), 4.00-3.88 (m, 2H), pyran-4- 3.89-3.80 (m, 2H), 3.63-3.45 (m, 4H), 3.04- ylcarbonyl)piperidin-4- 2.93 (m, 1H), 2.11-1.92 (m, 2H), 1.86-1.65 yl]oxy}benzamide (m, 4H), 1.66-1.58 (m, 2H) 163 4-{[1-(1,4-dioxan- 1H NMR (400 MHz, methanol-d4) δ ppm 8.79- (ESI(+)) 2- 8.75 (m, 1H), 8.23-8.19 (m, 1H), 8.04-7.97 m/e 465 ylcarbonyl)piperidin- (m, 2H), 7.93-7.82 (m, 3H), 7.09-7.02 (m, (M + H)+ 4-yl]oxy}-N- 2H), 4.79-4.71 (m, 1H), 4.69 (s, 2H), 4.47- (imidazo[1,2- 4.39 (m, 1H), 3.99-3.57 (m, 9H), 3.56-3.37 a]pyridin-6- (m, 1H), 2.11-1.88 (m, 2H), 1.90-1.62 (m, ylmethyl)benzamide 2H) 164 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm 8.79- (ESI(+)) a]pyridin-6- 8.76 (m, 1H), 8.23-8.19 (m, 1H), 8.04-7.97 m/e 449 ylmethyl)-4-({1- (m, 2H), 7.94-7.82 (m, 3H), 7.09-7.03 (m, (M + H)+ [(2S)- 2H), 4.79-4.71 (m, 2H), 4.69 (s, 2H), 3.98- tetrahydrofuran-2- 3.72 (m, 4H), 3.66-3.43 (m, 2H), 2.26-2.13 ylcarbonyl]piperidin-4- (m, 1H), 2.13-1.86 (m, 5H), 1.88-1.65 (m, yl}oxy)benzamide 2H) 165 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm 8.79- (ESI(+)) a]pyridin-6- 8.75 (m, 1H), 8.23-8.19 (m, 1H), 8.04-7.97 m/e 449 ylmethyl)-4-({1- (m, 2H), 7.93-7.82 (m, 3H), 7.09-7.03 (m, (M + H)+ [(2R)- 2H), 4.79-4.71 (m, 1H), 4.69 (s, 1H), 4.00- tetrahydrofuran-2- 3.71 (m, 4H), 3.67-3.43 (m, 1H), 2.26-2.13 ylcarbonyl]piperidin-4- (m, 1H), 2.13-1.86 (m, 5H), 1.88-1.65 (m, yl}oxy)benzamide 2H) 166 4-{[1-(2-hydroxy- 1H NMR (400 MHz, methanol-d4) δ ppm 8.79- (ESI(+)) 2-methylpropanoyl)pi- 8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7 Hz, 1H), m/e 437 peridin-4- 8.04-7.97 (m, 2H), 7.93-7.81 (m, 3H), 7.08- (M + H)+ yl]oxy}-N- 7.02 (m, 2H), 4.78-4.70 (m, 1H), 4.69 (s, 2H), (imidazo[1,2- 4.41-3.50 (m, 4H), 2.10-1.95 (m, 2H), 1.82- a]pyridin-6- 1.69 (m, 2H), 1.44 (s, 6H) ylmethyl)benzamide 167 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm 8.79- (ESI(+)) a]pyridin-6- 8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7 Hz, 1H), m/e 451 ylmethyl)-4-({1- 8.04-7.97 (m, 2H), 7.93-7.82 (m, 3H), 7.09- (M + H)+ [(propan-2- 7.03 (m, 2H), 4.80-4.72 (m, 1H), 4.69 (s, 2H), yloxy)acetyl]piper- 4.19 (s, 2H), 3.87-3.73 (m, 2H), 3.73-3.62 idin-4- (m, 1H), 3.59-3.45 (m, 2H), 2.11-1.93 (m, yl}oxy)benzamide 2H), 1.87-1.68 (m, 2H), 1.19 (d, J = 6.1 Hz, 6H) 168 4-[(1- 1H NMR (400 MHz, methanol-d4) δ ppm 8.79- (ESI(+)) butanoylpiperidin- 8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7 Hz, 1H), m/e 421 4-yl)oxy]-N- 8.04-7.97 (m, 2H), 7.96-7.81 (m, 3H), 7.08- (M + H)+ (imidazo[1,2- 7.02 (m, 2H), 4.78-4.70 (m, 1H), 4.69 (s, 2H), a]pyridin-6- 3.90-3.73 (m, 2H), 3.59-3.46 (m, 2H), 2.40 ylmethyl)benzamide (t, J = 7.5 Hz, 2H), 2.10-1.90 (m, 2H), 1.84- 1.57 (m, 4H), 0.98 (t, J = 7.4 Hz, 3H) 169 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm 8.80- (ESI(+)) a]pyridin-6- 8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7 Hz, 1H), m/e 451 ylmethyl)-4-{[1- 8.04-7.97 (m, 2H), 7.94-7.82 (m, 3H), 7.09- (M + H)+ (3-methoxy-2- 7.03 (m, 2H), 4.80-4.71 (m, 1H), 4.69 (s, 2H), methylpropanoyl) 4.01-3.71 (m, 2H), 3.71-3.41 (m, 3H), 3.38- piperidin-4- 3.31 (m, 1H), 3.30 (s, 3H), 3.26-3.16 (m, 1H), yl]oxy}benzamide 2.12-1.88 (m, 2H), 1.87-1.61 (m, 2H), 1.06 (d, J = 6.8 Hz, 3H) 170 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm 8.79- (ESI(+)) a]pyridin-6- 8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7 Hz, 1H), m/e 461 ylmethyl)-4-{[1- 8.04-7.97 (m, 2H), 7.94-7.81 (m, 3H), 7.09- (M + H)+ (3,3,3- 7.03 (m, 2H), 4.80-4.73 (m, 1H), 4.69 (s, 2H), trifluoropropanoyl)pi- 3.90-3.72 (m, 2H), 3.66-3.47 (m, 4H), 2.11- peridin-4- 1.90 (m, 2H), 1.91-1.68 (m, 2H) yl]oxy}benzamide 171 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm 8.79- (ESI(+)) a]pyridin-6- 8.76 (m, 1H), 8.21 (dd, J = 2.1, 0.7 Hz, 1H), m/e 477 ylmethyl)-4-{[1- 8.04-7.97 (m, 2H), 7.93-7.82 (m, 3H), 7.09- (M + H)+ (tetrahydro-2H- 7.03 (m, 2H), 4.78-4.71 (m, 1H), 4.68 (s, 2H), pyran-4- 3.97-3.74 (m, 4H), 3.59-3.48 (m, 2H), 3.48- ylacetyl)piperidin- 3.38 (m, 2H), 2.37 (d, J = 7.0 Hz, 2H), 2.10- 4- 1.90 (m, 3H), 1.85-1.60 (m, 4H), 1.41-1.26 yl]oxy}benzamide (m, 2H) 172 4-{[1- 1H NMR (400 MHz, methanol-d4) δ ppm 8.79- (ESI(+)) (cyclopropylace- 8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7 Hz, 1H), m/e 433 tyl)piperidin-4- 8.04-7.97 (m, 2H), 7.93-7.82 (m, 3H), 7.09- (M + H)+ yl]oxy}-N- 7.03 (m, 2H), 4.79-4.71 (m, 1H), 4.69 (s, 2H), (imidazo[1,2- 3.92-3.73 (m, 2H), 3.60-3.47 (m, 2H), 2.36 a]pyridin-6- (d, J = 6.8 Hz, 2H), 2.10-1.91 (m, 2H), 1.86- ylmethyl)benzamide 1.65 (m, 2H), 1.08-0.94 (m, 1H), 0.58-0.47 (m, 2H), 0.23-0.16 (m, 2H) 173 N-(imidazo[1,2- 1H NMR (400 MHz, methanol-d4) δ ppm 8.80- (ESI(+)) a]pyridin-6- 8.75 (m, 1H), 8.22-8.19 (m, 1H), 8.04-7.97 m/e 463 ylmethyl)-4-{[1- (m, 2H), 7.92-7.81 (m, 3H), 7.09-7.03 (m, (M + H)+ (tetrahydrofuran- 2H), 4.79-4.70 (m, 1H), 4.69 (s, 2H), 4.29- 2- 4.18 (m, 1H), 3.94-3.66 (m, 4H), 3.65-3.45 ylacetyl)piperidin- (m, 2H), 2.76 (dd, J = 14.8, 7.6 Hz, 1H), 2.52 4- (dd, J = 14.8, 5.2 Hz, 1H), 2.18-1.67 (m, 7H), yl]oxy}benzamide 1.69-1.53 (m, 1H) 411 4-[(1- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.96 (t, J = (ESI(+)) acetylpiperidin-4- 5.9 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (m, m/e 393 yl)oxy]-N- 3H), 7.51 (s, 1H), 7.37 (s, 1H), 7.07 (m, 2H), (M + H)+ (imidazo[1,2- 6.85 (dd, J = 6.9, 1.6 Hz, 1H), 4.72 (m, 1H), a]pyridin-7- 4.49 (d, J = 5.9 Hz, 2H), 3.85 (m, 1H), 3.68 (m, ylmethyl)benzamide 1H), 3.50-3.15 (m, 2H), 2.02 (s, 3H), 2.03- 1.85 (m 2H), 1.62 (m, 1H), 1.51 (m, 1H) 412 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.96 (t, J = (ESI(+)) a]pyridin-7- 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz, 1H), m/e 421 ylmethyl)-4-{[1- 7.88 (m, 3H), 7.51 (d, J = 1.2 Hz, 1H), 7.37 (s, (M + H)+ (2- 1H), 7.07 (m, 2H), 6.85 (dd, J = 6.9, 1.7 Hz, methylpropanoyl) 1H), 4.73 (m, 1H), 4.49 (d, J = 5.9 Hz, 2H), piperidin-4- 3.96-3.70 (m, 2H), 3.45-3.20 (m, 2H), 2.89 yl]oxy}benzamide (m, 1H), 1.93 (m, 2H), 1.58 (m, 2H), 1.00 (d, J = 6.7 Hz, 6H) 413 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.96 (t, J = (ESI(+)) a]pyridin-7- 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz, 1H), m/e 435 ylmethyl)-4-({1- 7.88 (m, 3H), 7.51 (s, 1H), 7.37 (s, 1H), 7.07 (M + H)+ [(2S)-2- (m, 2H), 6.85 (dd, J = 6.9, 1.6 Hz, 1H), 4.74 (m, methylbutanoyl]pi- 1H), 4.49 (d, J = 5.9 Hz, 2H), 4.00-3.74 (m, peridin-4- 2H), 3.50-3.15 (m, 2H), 2.72 (m, 1H), 1.95 yl}oxy)benzamide (m, 2H), 1.54 (m, 3H), 1.27 (m, 1H), 0.98 (d, J = 6.7 Hz, 3H), 0.81 (t, J = 7.4 Hz, 3H) 414 4-{[1- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.95 (t, J = (ESI(+)) (cyclopropylace- 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz, 1H), m/e 433 tyl)piperidin-4- 7.88 (m, 3H), 7.51 (d, J = 1.2 Hz, 1H), 7.37 (s, (M + H)+ yl]oxy}-N- 1H), 7.07 (m, 2H), 6.85 (dd, J = 7.0, 1.7 Hz, (imidazo[1,2- 1H), 4.73 (m, 1H), 4.49 (d, J = 5.9 Hz, 2H), a]pyridin-7- 3.89 (m, 1H), 3.69 (m, 1H), 3.40-3.15 (m, ylmethyl)benzamide 2H), 2.28 (d, J = 6.7 Hz, 2H), 1.93 (m, 2H), 1.85-1.41 (m, 2H), 0.95 (m, 1H), 0.45 (m, 2H), 0.12 (m, 2H) 415 4-[(1- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.96 (t, J = (ESI(+)) benzoylpiperidin- 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz, 1H), m/e 455 4-yl)oxy]-N- 7.90 (m, 3H), 7.51 (m, 1H), 7.47-7.37 (m, (M + H)+ (imidazo[1,2- 5H), 7.36 (m, 1H), 7.07 (m, 2H), 6.84 (dd, J = a]pyridin-7- 7.0, 1.7 Hz, 1H), 4.78 (m, 1H), 4.49 (d, J = 5.9 ylmethyl)benzamide Hz, 2H), 4.00 (m, 1H), 3.55 (m, 1H), 3.45- 3.15 (m, 2H), 2.00 (m, 2H), 164 (m, 2H) 416 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.96 (t, J = (ESI(+)) a]pyridin-7- 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz, 1H), m/e 451 ylmethyl)-4-({1- 7.88 (m, 3H), 7.51 (d, J = 1.2 Hz, 1H), 7.37 (s, (M + H)+ [(propan-2- 1H), 7.07 (m, 2H), 6.85 (dd, J = 7.0, 1.7 Hz, yloxy)acetyl]piper- 1H), 4.74 (m, 1H), 4.49 (d, J = 5.9 Hz, 2H), idin-4- 4.10 (d, J = 1.1 Hz, 2H), 3.85 (m, 1H), 3.70 (m, yl}oxy)benzamide 1H), 3.60 (m, 1H), 3.40-3.15 (m, 2H), 1.97 (m, 2H), 1.69-1.45 (m, 2H), 1.11 (d, J = 6.1 Hz, 6H) 417 4-{[1-(2-hydroxy- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.96 (t, J = (ESI(+)) 2- 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz, 1H), m/e 437 methylpropanoyl)pi- 7.88 (m, 3H), 7.51 (d, J = 1.2 Hz, 1H), 7.37 (s, (M + H)+ peridin-4- 1H), 7.07 (m, 2H), 6.85 (dd, J = 7.0, 1.7 Hz, yl]oxy}-N- 1H), 5.42 (m, 1H), 4.73 (m, 1H), 4.49 (d, J = (imidazo[1,2- 5.9 Hz, 2H), 4.42-3.78 (m, 2H), 3.70-3.20 a]pyridin-7- (m, 2H), 1.95 (m, 2H), 1.57 (m, 2H), 1.32 (s, ylmethyl)benzamide 6H) 418 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.96 (t, J = (ESI(+)) a]pyridin-7- 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz, 1H), m/e 449 ylmethyl)-4-({1- 7.88 (m, 3H), 7.51 (d, J = 1.2 Hz, 1H), 7.37 (s, (M + H)+ [(2R)- 1H), 7.07 (m, 2H), 6.85 (dd, J = 7.0, 1.7 Hz, tetrahydrofuran-2- 1H), 4.79-4.64 (m, 2H), 4.49 (d, J = 5.9 Hz, ylcarbonyl]piper- 2H), 3.95-3.70 (m, 4H), 3.50-3.15 (m, 2H), idin-4- 2.10-1.90 (m, 4H), 1.90-1.75 (m, 2H), 1.70- yl}oxy)benzamide 1.43 (m, 2H) 419 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.96 (t, J = (ESI(+)) a]pyridin-7- 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz, 1H), m/e 449 ylmethyl)-4-({1- 7.88 (m, 3H), 7.51 (d, J = 1.2 Hz, 1H), 7.37 (s, (M + H)+ [(2S)- 1H), 7.07 (m, 2H), 6.85 (dd, J = 6.9, 1.7 Hz, tetrahydrofuran-2- 1H), 4.79-4.64 (m, 2H), 4.49 (d, J = 5.9 Hz, ylcarbonyl]piper- 2H), 3.94-3.67 (m, 4H), 3.50-3.15 (m, 2H), idin-4- 2.10-1.90 (m, 4H), 1.90-1.75 (m, 2H), 1.70- yl}oxy)benzamide 1.43 (m, 2H) 420 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.96 (t, J = (ESI(+)) a]pyridin-7- 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz, 1H), m/e 463 ylmethyl)-4-{[1- 7.88 (m, 3H), 7.51 (d, J = 1.2 Hz, 1H), 7.37 (s, (M + H)+ (tetrahydro-2H- 1H), 7.07 (m, 2H), 6.85 (dd, J = 7.0, 1.7 Hz, pyran-4- 1H), 4.73 (m, 1H), 4.49 (d, J = 5.9 Hz, 2H), ylcarbonyl)piper- 3.84 (m, 4H), 3.45-3.15 (m, 4H), 2.90 (m, idin-4- 1H), 1.96 (m, 2H), 1.65-1.45 (m, 6H) yl]oxy}benzamide 421 4-{[1-(1,4-dioxan- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.96 (t, J = (ESI(+)) 2- 6.0 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz, 1H), m/e 465 ylcarbonyl)piper- 7.89 (m, 3H), 7.51 (d, J = 1.2 Hz, 1H), 7.37 (d, (M + H)+ idin-4-yl]oxy}-N- J = 1.5 Hz, 1H), 7.07 (m, 2H), 6.85 (dd, J = 7.0, (imidazo[1,2- 1.7 Hz, 1H), 4.74 (m, 1H), 4.49 (d, J = 5.9 Hz, a]pyridin-7- 2H), 4.35 (dd, J = 9.4, 2.8 Hz, 1H), 3.90-3.55 ylmethyl)benzamide (m, 7H), 3.55-3.15 (m, 3H), 1.98 (m, 2H), 1.75-1.40 (m, 2H) 422 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.95 (t, J = (ESI(+)) a]pyridin-7- 5.9 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.89 (m, m/e 477 ylmethyl)-4-{[1- 3H), 7.51 (s, 1H), 7.37 (bs, 1H), 7.07 (m, 2H), (M + H)+ (tetrahydro-2H- 6.85 (dd, J = 6.9, 1.7 Hz, 1H), 4.72 (m, 1H), pyran-4- 4.49 (d, J = 5.9 Hz, 2H), 3.95-3.67 (m, 4H), ylacetyl)piperidin- 3.45-3.15 (m, 5H), 2.28 (m, 2H), 1.93 (m, 4- 2H), 1.67-1.42 (m, 4H), 1.26-1.12 (m, 2H) yl]oxy}benzamide 423 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.96 (t, J = (ESI(+)) a]pyridin-7- 5.9 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.89 (m, m/e 478 ylmethyl)-4-{[1- 3H), 7.51 (s, 1H), 7.37 (s, 1H), 7.07 (m, 2H), (M + H)+ (morpholin-4- 6.85 (dd, J = 7.0, 1.6 Hz, 1H), 4.73 (m, 1H), ylacetyl)piperidin- 4.49 (d, J = 5.8 Hz, 2H), 3.86 (m, 2H), 3.57 (m, 4- 4H), 3.50-3.20 (m, 2H), 3.20-3.05 (m, 2H), yl]oxy}benzamide 2.40 (m, 4H), 2.08-1.89 (m, 2H), 1.70-1.41 (m, 2H) - The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 2-bromothiazole-5-carboxylic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 51A, substituting 2-methyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrol-1-yl)propan-2-ol for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 4-bromoaniline. 1H NMR (400 MHz, methanol-d4) δ ppm 8.41 (d, J=7.05 Hz, 1H) 8.27 (d, J=7.92 Hz, 2H) 8.00 (s, 1H) 7.80 (s, 1H) 7.53 (s, 1H) 7.47 (s, 1H) 6.93 (dd, J=6.99, 1.36 Hz, 1H) 4.61 (s, 2H) 4.16 (s, 2H) 1.20 (s, 6H); MS (ESI)(+)) m/e 397 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 4-bromoaniline. 1H NMR (400 MHz, methanol-d4) δ ppm 8.40 (d, J=6.94 Hz, 1H) 8.27 (d, J=7.48 Hz, 2H) 8.00 (s, 1H) 7.80 (s, 1H) 7.53 (s, 1H) 7.47 (s, 1H) 6.93 (d, J=6.83 Hz, 1H) 4.61 (s, 2H) 4.01 (d, J=7.26 Hz, 2H) 2.12-2.30 (m, 1H) 0.93 (d, J=6.61 Hz, 6H); MS (ESI)(+)) m/e 381 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(tert-butoxycarbonylamino)benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.62 (s, 1H), 8.92 (t, J=6.0 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90-7.79 (m, 3H), 7.57-7.49 (m, 3H), 7.39-7.35 (m, 1H), 6.85 (dd, J=7.0, 1.6 Hz, 1H), 4.48 (d, J=5.8 Hz, 2H), 1.49 (s, 9H); MS (ESI(+)) m/e 367 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(tert-butoxycarbonylamino)benzoic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 28A, substituting tert-butyl {4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 4-amino-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 3-methylbutan-1-amine and 2-(tetrahydro-2H-pyran-4-yl)acetic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.74 (dd, J=7.0, 0.9 Hz, 1H), 8.17 (dd, J=2.2, 0.7 Hz, 1H), 7.98 (d, J=2.2 Hz, 1H), 7.91-7.84 (m, 2H), 7.81-7.78 (m, 1H), 7.75-7.68 (m, 2H), 7.49 (dd, J=7.0, 1.6 Hz, 1H), 4.79-4.74 (m, 2H), 3.98-3.89 (m, 2H), 3.50-3.38 (m, 2H), 2.38-2.32 (m, 2H), 2.20-2.02 (m, 1H), 1.74-1.61 (m, 2H), 1.47-1.28 (m, 2H); MS (ESI(+)) m/e 393 (M+H)+.
-
TABLE 11 The following Examples were prepared essentially as described in Example 208, substituting the appropriate carboxylic acid in Example 208A and the appropriate carboxylic acid in Example 208C. Ex Name MS 209 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-2- (ESI(+)) ylacetyl)amino]benzamide m/e 379 (M + H)+ 210 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[3-(tetrahydrofuran-2- (ESI(+)) yl)propanoyl]amino}benzamide m/e 393 (M + H)+ 211 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(propan-2- (ESI(+)) yloxy)acetyl]amino}benzamide m/e 367 (M + H)+ 212 4-[(3-cyclopentylpropanoyl)amino]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 391 (M + H)+ 213 N-(imidazo [1,2-a]pyridin-7-ylmethyl)-4-[(4- (ESI(+)) methylpentanoyl)amino]benzamide m/e 365 (M + H)+ 214 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-3- (ESI(+)) ylacetyl)amino]benzamide m/e 379 (M + H)+ 305 4-[(cyclopentylacetyl)amino]-3-fluoro-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 395 (M + H)+ 463 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 395 (M + H)+ 867 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(2- (ESI(+)) methoxyphenyl)acetyl]amino}benzamide m/e 415 (M + H)+ 868 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4- (ESI(+)) [(phenylacetyl)amino]benzamide m/e 385 (M + H)+ 869 4-(benzoylamino)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide (ESI(+)) m/e 371 (M + H)+ 870 2,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)carbamoyl]phenyl}benzamide m/e 407 (M + H)+ 871 3,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)carbamoyl]phenyl}benzamide m/e 407 (M + H)+ 872 3,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)carbamoyl]phenyl}benzamide m/e 407 (M + H)+ 873 2,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)carbamoyl]phenyl}benzamide m/e 407 (M + H)+ 874 2-fluoro-N-{4-[(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)carbamoyl]phenyl}benzamide m/e 389 (M + H)+ 875 N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-3- (ESI(+)) methoxybenzamide m/e 401 (M + H)+ 876 4-{[(2-fluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 403 (M + H)+ 880 N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-2- (ESI(+)) methoxybenzamide m/e 401 (M + H)+ 890 4-{[(2,5-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 421 (M + H)+ 891 4-{[(2,4-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 421 (M + H)+ 895 4-{[difluoro(phenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 421 (M + H)+ 896 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(2-methyl-2- (ESI(+)) phenylpropanoyl)amino]benzamide m/e 413 (M + H)+ - A solution of methyl 4-aminobenzoate (0.2 g, 1.323 mmol) and 4-formylbenzonitrile (0.177 g, 1.350 mmol) in methanol (2 ml) and dichloromethane (4 ml) was treated with acetic acid (0.379 ml, 6.62 mmol) followed by MP-cyanoborohydride (1.151 g, 2.65 mmol) and the reaction was slowly stirred at room temperature. After 16 hours, the mixture was filtered and concentrated and the concentrate was partitioned between 2 N sodium hydroxide and dichloromethane. The organic phase was concentrated to give the title compound with 30% of remaining 4-formylbenzonitrile.
- The title compound was prepared as described in Example 52A, substituting methyl 4-(4-cyanobenzylamino)benzoate for methyl 4-aminobenzoate.
- The title compound was prepared as described in Example 4B, substituting methyl 4-(N-(4-cyanobenzyl)-2-cyclopentylacetamido)benzoate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(N-(4-cyanobenzyl)-2-cyclopentylacetamido)benzoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.08 (t, J=5.8 Hz, 1H), 8.47 (s, 1H), 7.94 (s, 1H), 7.90-7.85 (m, 2H), 7.79-7.74 (m, 2H), 7.56-7.49 (m, 2H), 7.43-7.37 (m, 2H), 7.36-7.30 (m, 2H), 7.21 (dd, J=9.3, 1.7 Hz, 1H), 4.98 (bs, 2H), 4.45 (d, J=5.8 Hz, 2H), 2.19-2.13 (m, 3H), 1.74-1.66 (m, 2H), 1.51-1.38 (m, 4H), 1.01-0.92 (m, 2H); MS (ESI(+)) m/e 492 (M+H)+.
- The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.56 (s, 1H), 8.51-8.45 (m, 1H), 7.88 (s, 1H), 7.52-7.49 (m, 1H), 7.39-7.36 (m, 1H), 7.35-7.30 (m, 2H), 7.12-7.07 (m, 2H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.67 (t, J=6.0 Hz, 1H), 4.32 (d, J=6.0 Hz, 2H), 4.10-4.00 (m, 2H), 2.89-2.65 (m, 2H), 2.62-2.54 (m, 1H), 1.75-1.66 (m, 2H), 1.49-1.37 (m, 11H); MS (ESI(+)) m/e 450 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.02 (t, J=6.0 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90-7.81 (m, 3H), 7.51 (d, J=1.2 Hz, 1H), 7.40-7.32 (m, 3H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.13-4.03 (m, 2H), 2.91-2.69 (m, 3H), 1.82-1.72 (m, 2H), 1.60-1.44 (m, 2H), 1.42 (s, 9H); MS (ESI(+)) m/e 435 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-(piperidin-4-yl)phenyl)urea for 3-methylbutan-1-amine and tetrahydrofuran-2-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.72 (d, J=7.0 Hz, 1H), 8.17-8.12 (m, 1H), 7.98-7.93 (m, 1H), 7.78 (bs, 1H), 7.48-7.41 (m, 1H), 7.35-7.28 (m, 2H), 7.18-7.12 (m, 2H), 4.81-4.72 (m, 1H), 4.67-4.55 (m, 3H), 4.19-4.08 (m, 1H), 4.01-3.91 (m, 1H), 3.90-3.81 (m, 1H), 3.24-3.09 (m, 1H), 2.85-2.67 (m, 2H), 2.30-2.14 (m, 1H), 2.09-1.79 (m, 5H), 1.73-1.46 (m, 2H); MS (ESI(+)) m/e 448 (M+H)+.
-
TABLE 12 The following Examples were prepared essentially as described in Example 220, substituting the appropriate carboxylic acid in Example 220B. Ex Name MS 221 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran- (ESI(+)) 4-ylcarbonyl)piperidin-4-yl]phenyl}urea m/e 462 (M + H)+ 222 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]phenyl}-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 464 (M + H)+ 223 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran- (ESI(+)) 4-ylacetyl)piperidin-4-yl]phenyl}urea m/e 476 (M + H)+ 224 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(morpholin-4- (ESI(+)) ylacetyl)piperidin-4-yl]phenyl}urea m/e 477 (M + H)+ 225 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2- (ESI(+)) ylacetyl)piperidin-4-yl]phenyl}urea m/e 462 (M + H)+ 226 1-{4-[1-(3-hydroxy-3-methylbutanoyl)piperidin-4-yl]phenyl}-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 450 (M + H)+ 227 1-{4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]phenyl}-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 436 (M + H)+ 228 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2- (ESI(+)) methylpropanoyl)piperidin-4-yl]phenyl}urea m/e 420 (M + H)+ 229 1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)urea m/e 454 (M + H)+ 243 1-(4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4- (ESI(+)) yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7- m/e 510 ylmethyl)urea (M + H)+ 286 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3S)-tetrahydrofuran- (ESI(+)) 3-ylcarbonyl]piperidin-4-yl}phenyl)urea m/e 448 (M + H)+ 287 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3R)- (ESI(+)) tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}phenyl)urea m/e 448 (M + H)+ 288 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran- (ESI(+)) 2-ylcarbonyl]piperidin-4-yl}phenyl)urea m/e 448 (M + H)+ 289 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)- (ESI(+)) tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}phenyl)urea m/e 448 (M + H)+ 709 1-[4-(1-butanoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)urea m/e 420 (M + H)+ 710 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2- (ESI(+)) methylbutanoyl]piperidin-4-yl}phenyl)urea m/e 434 (M + H)+ 711 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2- (ESI(+)) methylcyclopropyl)carbonyl]piperidin-4-yl}phenyl)urea m/e 432 (M + H)+ 712 1-{4-[1-(cyclopropylacetyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)urea m/e 432 (M + H)+ 713 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3,3,3- (ESI(+)) trifluoropropanoyl)piperidin-4-yl]phenyl}urea m/e 460 (M + H)+ 714 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,4,4- (ESI(+)) trifluorobutanoyl)piperidin-4-yl]phenyl}urea m/e 474 (M + H)+ 715 1-(4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}phenyl)-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 496 (M + H)+ 716 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1- (ESI(+)) (phenylacetyl)piperidin-4-yl]phenyl}urea m/e 468 (M + H)+ 719 1-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)urea m/e 472 (M + H)+ 720 1-{4-[1-(3-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)urea m/e 472 (M + H)+ 721 1-{4-[1-(4-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)urea m/e 472 (M + H)+ 722 1-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 490 (M + H)+ 723 1-{4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 490 (M + H)+ 724 1-{4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 490 (M + H)+ 725 1-{4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 490 (M + H)+ 938 1-(4-{1-[(2-chloropyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 489 (M + H)+ 939 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3-methylbut-2- ESI(+)) enoyl)piperidin-4-yl]phenyl}urea m/e 432 (M + H)+ 940 1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 448 (M + H)+ 941 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methylcyclopent- ESI(+)) 1-en-1-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 458 (M + H)+ 942 1-{4-[1-(2-ethylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)urea m/e 448 (M + H)+ 943 1-(4-{1-[(4-fluorophenoxy)acetyl]piperidin-4-yl}phenyl)-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 502 (M + H)+ 944 1-{4-[1-(2,4-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 514 (M + H)+ 945 1-{4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 458 (M + H)+ 946 1-{4-[1-(2,5-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 514 (M + H)+ 947 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2- ESI(+)) methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea m/e 498 (M + H)+ 948 1-{4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 498 (M + H)+ 949 1-{4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 514 (M + H)+ 950 1-{4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 477 (M + H)+ 951 1-(4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 503 (M + H)+ 952 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3- ESI(+)) methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea m/e 498 (M + H)+ 953 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-oxo-2,3-dihydro- ESI(+)) 1H-inden-4-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 508 (M + H)+ 954 1-{4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 513 (M + H)+ 955 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-2-methylbut-2- ESI(+)) enoyl]piperidin-4-yl}phenyl)urea m/e 432 (M + H)+ 956 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(1H-indol-3- ESI(+)) ylacetyl)piperidin-4-yl]phenyl}urea m/e 507 (M + H)+ 957 1-{4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 484 (M + H)+ 1011 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-(propan-2-yl)-1H- ESI(+)) pyrazol-3-yl]carbonyl}piperidin-4-yl)phenyl]urea m/e 486 (M + H)+ 1012 1-(4-{1-[(2S)-2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl]piperidin- ESI(+)) 4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 512 (M + H)+ 1013 1-(4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5- ESI(+)) yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7- m/e 497 ylmethyl)urea (M + H)+ 1014 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-4,5,6,7- ESI(+)) tetrahydro-2H-indazol-3-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 512 (M + H)+ 1015 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-tetrahydro- ESI(+)) 2,1-benzoxazol-3-ylcarbonyl)piperidin-4-yl]phenyl}urea m/e 499 (M + H)+ 1016 1-(4-{1-[(2-chloro-5-fluoropyridin-4-yl)carbonyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 507 (M + H)+ 1017 1-(4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 487 (M + H)+ 1018 1-(4-{1-[(2-chloro-3-fluoropyridin-4-yl)carbonyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 507 (M + H)+ 1019 1-(4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 489 (M + H)+ 1020 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-(pyridin-2- ESI(+)) yl)cyclopropyl]carbonyl}piperidin-4-yl)phenyl]urea m/e 495 (M + H)+ 1021 1-(4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 512 (M + H)+ 1022 1-[4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-yl]carbonyl}piperidin-4- ESI(+)) yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 494 (M + H)+ 1023 1-{4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperidin-4- ESI(+)) yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 512 (M + H)+ 1024 1-{4-[1-(2,3-dihydro-1-benzofuran-2-ylcarbonyl)piperidin-4- ESI(+)) yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 496 (M + H)+ 1025 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4- ESI(+)) methoxycyclohexyl)carbonyl]piperidin-4-yl}phenyl)urea m/e 490 (M + H)+ 1026 1-{4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)piperidin-4- ESI(+)) yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 512 (M + H)+ 1027 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-4- ESI(+)) ylcarbonyl)piperidin-4-yl]phenyl}urea m/e 505 (M + H)+ 1028 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-1,3- ESI(+)) benzoxazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 509 (M + H)+ 1029 1-(4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)carbonyl]piperidin- ESI(+)) 4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 514 (M + H)+ 1030 1-(4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-4-yl}phenyl)-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 471 (M + H)+ 1031 1-{4-[1-(cinnolin-4-ylcarbonyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 506 (M + H)+ 1032 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(quinolin-7- ESI(+)) ylcarbonyl)piperidin-4-yl]phenyl}urea m/e 505 (M + H)+ 1033 1-{4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 497 (M + H)+ 1034 1-(4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 485 (M + H)+ 1035 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(5,6,7,8- ESI(+)) tetrahydroquinolin-3-ylcarbonyl)piperidin-4-yl]phenyl}urea m/e 509 (M + H)+ 1036 1-{4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6- ESI(+)) ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7- m/e 511 ylmethyl)urea (M + H)+ 1037 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-7- ESI(+)) ylcarbonyl)piperidin-4-yl]phenyl}urea m/e 505 (M + H)+ 1038 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(quinoxalin-2- ESI(+)) ylcarbonyl)piperidin-4-yl]phenyl}urea m/e 506 (M + H)+ 1039 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-(2- ESI(+)) methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl}phenyl)urea m/e 511 (M + H)+ 1040 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-(pyridin-2- ESI(+)) yl)prop-2-enoyl]piperidin-4-yl}phenyl)urea m/e 481 (M + H)+ 1041 1-(4-{1-[(4-chloro-2,6-dimethylpyridin-3-yl)carbonyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e XXX (M + H)+ 1042 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(8- ESI(+)) methylimidazo[1,2-a]pyridin-2-yl)carbonyl]piperidin-4- m/e 517 yl}phenyl)urea (M + H)+ 1043 1-(4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 499 (M + H)+ 4044 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-4,5,6,7- ESI(+)) tetrahydro-1H-indazol-3-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 512 (M + H)+ 1045 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methyl-4H- ESI(+)) furo[3,2-b]pyrrol-5-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 497 (M + H)+ 1046 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2,3- ESI(+)) dihydro-1-benzofuran-5-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 510 (M + H)+ 1047 1-(4-{1-[(4-chloro-1-ethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 506 (M + H)+ 1048 1-{4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 497 (M + H)+ 1049 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-8- ESI(+)) ylcarbonyl)piperidin-4-yl]phenyl}urea m/e 505 (M + H)+ 1050 1-(4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}phenyl)-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 493 (M + H)+ 1051 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3-methoxythiophen- ESI(+)) 2-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 490 (M + H)+ 1052 1-{4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 497 (M + H)+ 1053 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-tetrahydro- ESI(+)) 1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]phenyl}urea m/e 515 (M + H)+ 1054 1-{4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 511 (M + H)+ 1055 1-(4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}phenyl)- ESI(+)) 3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 473 (M + H)+ 1056 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[3-methyl-1-(prop-2- ESI(+)) en-1-yl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)phenyl]urea m/e 498 (M + H)+ 1057 1-{4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]phenyl}- ESI(+)) 3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 512 (M + H)+ 1058 1-(4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}phenyl)- ESI(+)) 3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 489 (M + H)+ 1059 1-(4-{1-[(5,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)- ESI(+)) 3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 483 (M + H)+ 1060 1-{4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 511 (M + H)+ 1065 1-(4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl}phenyl)-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 517 (M + H)+ 1066 1-(4-{1-[(3,5-difluoropyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)- ESI(+)) 3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 492 (M + H)+ 1121 1-(4-{1-[(2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 501 (M + H)+ 1122 1-{4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 511 (M + H)+ 1123 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H- ESI(+)) indazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 508 (M + H)+ 1124 1-(4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5- ESI(+)) yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7- m/e 506 ylmethyl)urea (M + H)+ 1125 1-(4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 483 (M + H)+ 1126 1-(4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 514 (M + H)+ 1127 1-(4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 471 (M + H)+ 1128 1-(4-{1-[(1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 501 (M + H)+ 1129 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(thieno[3,2-b]furan-5- ESI(+)) ylcarbonyl)piperidin-4-yl]phenyl}urea m/e 500 (M + H)+ 1130 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxythiophen- ESI(+)) 2-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 490 (M + H)+ 1131 1-(4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 485 (M + H)+ 1132 1-(4-{1-[(5-cyclopropylpyridin-2-yl)carbonyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 495 (M + H)+ 1133 1-{4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 515 (M + H)+ 1134 1-[4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4- ESI(+)) yl]carbonyl}piperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7- m/e 514 ylmethyl)urea (M + H)+ 1135 1-{4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 494 (M + H)+ 1136 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxy-5- ESI(+)) methylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 499 (M + H)+ 1137 1-(4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 512 (M + H)+ 1138 1-(4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}phenyl)- ESI(+)) 3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 495 (M + H)+ 1139 1-(4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 485 (M + H)+ 1140 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[4-(propan-2- ESI(+)) yl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)phenyl]urea m/e 498 (M + H)+ 1141 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-5-propyl- ESI(+)) 1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 500 (M + H)+ 1142 1-(4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-yl)propanoyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 512 (M + H)+ 1143 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(pyrazolo[1,5- ESI(+)) a]pyridin-2-ylcarbonyl)piperidin-4-yl]phenyl}urea m/e 494 (M + H)+ 1144 1-{4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-4-yl]phenyl}-3- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 494 (M + H)+ 1145 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2-(propan-2-yl)-1,3- ESI(+)) oxazol-4-yl]carbonyl}piperidin-4-yl)phenyl]urea m/e 487 (M + H)+ 1146 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H- ESI(+)) indazol-7-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 508 (M + H)+ 1147 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methoxy-5- ESI(+)) methylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 499 (M + H)+ 1148 1-(4-{1-[(5,6-dimethoxypyridin-2-yl)carbonyl]piperidin-4- ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 515 (M + H)+ 1149 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2H- ESI(+)) indazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 508 (M + H)+ 1150 1-(4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]piperidin-4-yl}phenyl)- ESI(+)) 3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 517 (M + H)+ 1151 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2H- ESI(+)) indazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 508 (M + H)+ 1152 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H- ESI(+)) indazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea m/e 508 (M + H)+ 1153 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2- ESI(+)) (trifluoromethyl)furan-3-yl]carbonyl}piperidin-4-yl)phenyl]urea m/e 512 (M + H)+ - The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 2-hydroxy-2-methylpropanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6/D2O, Temp=90° C.) δ ppm 8.77 (dd, J=6.9, 0.9 Hz, 1H), 8.22-8.18 (m, 1H), 8.02-7.98 (m, 1H), 7.88-7.81 (m, 2H), 7.77 (s, 1H), 7.44 (dd, J=6.9, 1.6 Hz, 1H), 7.40-7.34 (m, 2H), 4.76-4.64 (m, 4H), 2.98-2.82 (m, 3H), 1.89-1.81 (m, 2H), 1.65-1.48 (m, 2H), 1.38 (s, 6H); MS (ESI(+)) m/e 421 (M+H)+.
-
TABLE 13 The following Examples were prepared essentially as described in Example 230, substituting the appropriate carboxylic acid in Example 230B. Ex Name MS 231 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-3- (ESI(+)) ylcarbonyl)piperidin-4-yl]benzamide m/e 443 (M + H)+ 232 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4- (ESI(+)) ylcarbonyl)piperidin-4-yl]benzamide m/e 447 (M + H)+ 233 4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 445 (M + H)+ 234 4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]piperidin- (ESI(+)) 4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 495 (M + H)+ 235 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-2- (ESI(+)) ylacetyl)piperidin-4-yl]benzamide m/e 447 (M + H)+ 236 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4- (ESI(+)) ylacetyl)piperidin-4-yl]benzamide m/e 461 (M + H)+ 237 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2- (ESI(+)) yloxy)acetyl]piperidin-4-yl}benzamide m/e 435 (M + H)+ 238 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2- (ESI(+)) methylbutanoyl]piperidin-4-yl}benzamide m/e 419 (M + H)+ 239 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2- (ESI(+)) methylpropanoyl)piperidin-4-yl]benzamide m/e 405 (M + H)+ 308 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3- (ESI(+)) ylcarbonyl]piperidin-4-yl}benzamide m/e 433 (M + H)+ 309 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3R)-tetrahydrofuran-3- (ESI(+)) ylcarbonyl]piperidin-4-yl}benzamide m/e 433 (M + H)+ 310 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2- (ESI(+)) ylcarbonyl]piperidin-4-yl}benzamide m/e 433 (M + H)+ 311 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2- (ESI(+)) ylcarbonyl]piperidin-4-yl}benzamide m/e 433 (M + H)+ 312 4-[1-(cyclopropylacetyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 417 (M + H)+ 313 4-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 377 (M + H)+ 437 4-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 439 (M + H)+ 44 4-{1-[(3,3-difluorocyclobutyl)carbonyl]piperidin-4-yl}-N- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 453 (M + H)+ 441 4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 481 (M + H)+ 484 4-[1-(furan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)benzamide m/e 429 (M + H)+ 498 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2- (ESI(+)) ylcarbonyl)piperidin-4-yl]benzamide m/e 440 (M + H)+ 499 4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 433 (M + H)+ 500 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4- (ESI(+)) methylbenzoyl)piperidin-4-yl]benzamide m/e 453 (M + H)+ 501 4-[1-(2,2-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 433 (M + H)+ 502 4-[1-(cyclohexylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)benzamide m/e 445 (M + H)+ 503 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2- (ESI(+)) ylcarbonyl)piperidin-4-yl]benzamide m/e 445 (M + H)+ 504 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3,3,3- (ESI(+)) trifluoropropanoyl)piperidin-4-yl]benzamide m/e 445 (M + H)+ 505 4-(1-butanoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 405 (M + H)+ 506 4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)benzamide m/e 475 (M + H)+ 507 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2- (ESI(+)) methylbenzoyl)piperidin-4-yl]benzamide m/e 453 (M + H)+ 508 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 457 (M + H)+ 509 4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 419 (M + H)+ 510 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylpent-2- (ESI(+)) enoyl]piperidin-4-yl}benzamide m/e 431 (M + H)+ 511 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol- (ESI(+)) 5-yl)carbonyl]piperidin-4-yl}benzamide m/e 443 (M + H)+ 512 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyloxetan-3- (ESI(+)) yl)carbonyl]piperidin-4-yl}benzamide m/e 433 (M + H)+ 513 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 457 (M + H)+ 514 4-{1-[(1-cyanocyclopropyl)carbonyl]piperidin-4-yl}-N- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 428 (M + H)+ 515 4-[1-(cyclopentylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)benzamide m/e 431 (M + H)+ 516 4-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 457 (M + H)+ 517 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol- (ESI(+)) 4-yl)carbonyl]piperidin-4-yl}benzamide m/e 443 (M + H)+ 518 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2- (ESI(+)) oxobutanoyl)piperidin-4-yl]benzamide m/e 419 (M + H)+ 519 4-{1-[(2,5-dimethylfuran-3-yl)carbonyl]piperidin-4-yl}-N- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 457 (M + H)+ 520 4-[1-(4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 464 (M + H)+ 521 4-[1-(3-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 464 (M + H)+ 522 4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)benzamide m/e 475 (M + H)+ 523 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2- (ESI(+)) ylcarbonyl)piperidin-4-yl]benzamide m/e 441 (M + H)+ 524 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2- (ESI(+)) yl)carbonyl]piperidin-4-yl}benzamide m/e 459 (M + H)+ 525 4-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]piperidin-4-yl}-N- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 458 (M + H)+ 526 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3- (ESI(+)) methoxybenzoyl)piperidin-4-yl]benzamide m/e 469 (M + H)+ 527 4-[1-(3-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 473 (M + H)+ 528 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4- (ESI(+)) methoxybenzoyl)piperidin-4-yl]benzamide m/e 469 (M + H)+ 529 4-[1-(4-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 473 (M + H)+ 530 4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)benzamide m/e 475 (M + H)+ 531 4-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 403 (M + H)+ 532 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-propanoylpiperidin-4- (ESI(+)) yl)benzamide m/e 391 (M + H)+ 533 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2- (ESI(+)) yl)carbonyl]piperidin-4-yl}benzamide m/e 442 (M + H)+ 534 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3- (ESI(+)) methylbutanoyl)piperidin-4-yl]benzamide m/e 419 (M + H)+ 535 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4- (ESI(+)) ylcarbonyl)piperidin-4-yl]benzamide m/e 440 (M + H)+ 536 4-[1-(2,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 433 (M + H)+ 537 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3- (ESI(+)) ylcarbonyl)piperidin-4-yl]benzamide m/e 440 (M + H)+ 538 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1- (ESI(+)) methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide m/e 417 (M + H)+ 539 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2- (ESI(+)) methoxybenzoyl)piperidin-4-yl]benzamide m/e 469 (M + H)+ 699 4-[1-(2-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 473 (M + H)+ 700 4-[1-(2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)benzamide m/e 475 (M + H)+ 701 4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)benzamide m/e 475 (M + H)+ 702 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3- (ESI(+)) (trifluoromethyl)benzoyl]piperidin-4-yl}benzamide m/e 507 (M + H)+ 703 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3- (ESI(+)) (trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide m/e 523 (M + H)+ 704 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4- (ESI(+)) (trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide m/e 523 (M + H)+ 705 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4- (ESI(+)) (trifluoromethyl)benzoyl]piperidin-4-yl}benzamide m/e 507 (M + H)+ 706 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2- (ESI(+)) (trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide m/e 523 (M + H)+ 707 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylacetyl)piperidin- (ESI(+)) 4-yl]benzamide m/e 453 (M + H)+ 708 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2- (ESI(+)) (trifluoromethyl)benzoyl]piperidin-4-yl}benzamide m/e 507 (M + H)+ 737 4-[1-(2-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 464 (M + H)+ 913 4-{1-[(2-chloropyridin-3-yl)carbonyl]piperidin-4-yl}-N- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 474 (M + H)+ 914 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbut-2- ESI(+)) enoyl)piperidin-4-yl]benzamide m/e 417 (M + H)+ 915 4-[1-(3-fluoro-4-methoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 487 (M + H)+ 916 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopent-1- ESI(+)) en-1-yl)carbonyl]piperidin-4-yl}benzamide m/e 443 (M + H)+ 917 4-[1-(2-ethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7- ESI(+)) ylmethyl)benzamide m/e 433 (M + H)+ 918 4-{1-[(4-fluorophenoxy)acetyl]piperidin-4-yl}-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 487 (M + H)+ 919 4-[1-(3,5-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 499 (M + H)+ 920 4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 443 (M + H)+ 921 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2- ESI(+)) methoxyphenyl)acetyl]piperidin-4-yl}benzamide m/e 483 (M + H)+ 922 4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 483 (M + H)+ 923 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3- ESI(+)) methylbenzoyl)piperidin-4-yl]benzamide m/e 453 (M + H)+ 924 4-[1-(2-acetylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7- ESI(+)) ylmethyl)benzamide m/e 481 (M + H)+ 925 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2- ESI(+)) (methoxymethyl)benzoyl]piperidin-4-yl}benzamide m/e 483 (M + H)+ 926 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2- ESI(+)) phenylpropanoyl)piperidin-4-yl]benzamide m/e 467 (M + H)+ 927 4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 499 (M + H)+ 928 4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 462 (M + H)+ 929 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[(2- ESI(+)) methylpropyl)sulfonyl]acetyl}piperidin-4-yl)benzamide m/e 497 (M + H)+ 930 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2- ESI(+)) phenoxypropanoyl)piperidin-4-yl]benzamide m/e 483 (M + H)+ 931 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-({[(1R,2S)-2- ESI(+)) methylcyclohexyl]oxy}acetyl)piperidin-4-yl]benzamide m/e 489 (M + H)+ 932 4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 488 (M + H)+ 933 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3- ESI(+)) methoxyphenyl)acetyl]piperidin-4-yl}benzamide m/e 483 (M + H)+ 934 4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 498 (M + H)+ 935 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylbut-2- ESI(+)) enoyl]piperidin-4-yl}benzamide m/e 417 (M + H)+ 936 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxy-5- ESI(+)) methylphenyl)acetyl]piperidin-4-yl}benzamide m/e 497 (M + H)+ 937 4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 469 (M + H)+ 959 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(propan-2-yl)-1H- ESI(+)) pyrazol-3-yl]carbonyl}piperidin-4-yl)benzamide m/e 471 (M + H)+ 960 4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin- ESI(+)) 4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 483 (M + H)+ 961 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-4,5,6,7- ESI(+)) tetrahydro-2H-indazol-3-yl)carbonyl]piperidin-4-yl}benzamide m/e 497 (M + H)+ 962 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-2,1- ESI(+)) benzoxazol-3-ylcarbonyl)piperidin-4-yl]benzamide m/e 484 (M + H)+ 963 4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 472 (M + H)+ 964 4-{1-[(2-chloro-3-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 492 (M + H)+ 965 4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 474 (M + H)+ 966 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(pyridin-2- ESI(+)) yl)cyclopropyl]carbonyl}piperidin-4-yl)benzamide m/e 480 (M + H)+ 967 4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 497 (M + H)+ 968 4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 501 (M + H)+ 969 4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-yl]carbonyl}piperidin-4- ESI(+)) yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 479 (M + H)+ 970 4-[1-(3,4-dihydro-2H-chromen-6-ylcarbonyl)piperidin-4-yl]-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 495 (M + H)+ 971 4-{1-[(cyclohexyloxy)acetyl]piperidin-4-yl}-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 475 (M + H)+ 972 4-{1-[(2-chloropyridin-3-yl)acetyl]piperidin-4-yl}-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 488 (M + H)+ 973 4-{1-[(5-cyclopropyl-1,2-oxazol-3-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 470 (M + H)+ 974 4-[1-(2H-chromen-3-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 493 (M + H)+ 975 4-{1-[(3,5-difluoropyridin-2-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 476 (M + H)+ 976 4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperidin-4-yl]-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 497 (M + H)+ 977 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4- ESI(+)) methoxycyclohexyl)carbonyl]piperidin-4-yl}benzamide m/e 475 (M + H)+ 978 4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)piperidin-4-yl]-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 497 (M + H)+ 979 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-4- ESI(+)) ylcarbonyl)piperidin-4-yl]benzamide m/e 490 (M + H)+ 980 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-1,3- ESI(+)) benzoxazol-6-yl)carbonyl]piperidin-4-yl}benzamide m/e 494 (M + H)+ 981 4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4- ESI(+)) yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 499 (M + H)+ 982 4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 456 (M + H)+ 983 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thieno[3,2-b]pyridin-2- ESI(+)) ylcarbonyl)piperidin-4-yl]benzamide m/e 496 (M + H)+ 984 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinolin-7- ESI(+)) ylcarbonyl)piperidin-4-yl]benzamide m/e 490 (M + H)+ 985 4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 482 (M + H)+ 986 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(5,6,7,8- ESI(+)) tetrahydroquinolin-3-ylcarbonyl)piperidin-4-yl]benzamide m/e 494 (M + H)+ 987 4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-ylcarbonyl)piperidin- ESI(+)) 4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 496 (M + H)+ 988 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-7- ESI(+)) ylcarbonyl)piperidin-4-yl]benzamide m/e 490 (M + H)+ 989 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinoxalin-2- ESI(+)) ylcarbonyl)piperidin-4-yl]benzamide m/e 491 (M + H)+ 990 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-3-(2- ESI(+)) methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl}benzamide m/e 496 (M + H)+ 991 -(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-3-(pyridin-2- ESI(+)) yl)prop-2-enoyl]piperidin-4-yl}benzamide m/e 466 (M + H)+ 992 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(8-methylimidazo[1,2- ESI(+)) a]pyridin-2-yl)carbonyl]piperidin-4-yl}benzamide m/e 493 (M + H)+ 993 4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 484 (M + H)+ 994 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-4,5,6,7- ESI(+)) tetrahydro-1H-indazol-3-yl)carbonyl]piperidin-4-yl}benzamide m/e 497 (M + H)+ 995 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methyl-4H-furo[3,2- ESI(+)) b]pyrrol-5-yl)carbonyl]piperidin-4-yl}benzamide m/e 482 (M + H)+ 996 4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 482 (M + H)+ 997 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-8- ESI(+)) ylcarbonyl)piperidin-4-yl]benzamide m/e 490 (M + H)+ 998 4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 478 (M + H)+ 999 4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 482 (M + H)+ 1000 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-1,3- ESI(+)) benzothiazol-2-ylcarbonyl)piperidin-4-yl]benzamide m/e 500 (M + H)+ 1001 4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 496 (M + H)+ 1002 4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 458 (M + H)+ 1003 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[3-methyl-1-(prop-2- ESI(+)) en-1-yl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)benzamide m/e 483 (M + H)+ 1004 4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 497 (M + H)+ 1005 4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 474 (M + H)+ 1006 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2- ESI(+)) yl)pyrimidin-4-yl]carbonyl}piperidin-4-yl)benzamide m/e 483 (M + H)+ 1007 4-{1-[(5,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 468 (M + H)+ 1008 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2- ESI(+)) yl)tetrahydro-2H-pyran-4-yl]carbonyl}piperidin-4-yl)benzamide m/e 489 (M + H)+ 1009 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxy-6- ESI(+)) methylbenzoyl)piperidin-4-yl]benzamide m/e 483 (M + H)+ 1010 4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 496 (M + H)+ 1061 4-{1-[(2-chloro-5-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 493 (M + H)+ 1062 4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 471 (M + H)+ 1063 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{l-[(3-methoxythiophen-2- ESI(+)) yl)carbonyl]piperidin-4-yl}benzamide m/e 476 (M + H)+ 1064 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-methyl-5-(propan-2- ESI(+)) yl)furan-3-yl]carbonyl}piperidin-4-yl)benzamide m/e 486 (M + H)+ 1084 4-{1-[(2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 486 (M + H)+ 1085 4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 496 (M + H)+ 1086 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-indazol- ESI(+)) 6-yl)carbonyl]piperidin-4-yl}benzamide m/e 493 (M + H)+ 1087 4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4- ESI(+)) yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 491 (M + H)+ 1088 4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 468 (M + H)+ 1089 4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 499 (M + H)+ 1090 4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 456 (M + H)+ 1091 4-{1-[(1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 486 (M + H)+ 1092 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxythiophen-2- ESI(+)) yl)carbonyl]piperidin-4-yl}benzamide m/e 475 (M + H)+ 1093 4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 470 (M + H)+ 1094 4-{1-[(5-cyclopropylpyridin-2-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 480 (M + H)+ 1095 4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 500 (M + H)+ 1096 4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4-yl]carbonyl}piperidin- ESI(+)) 4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 499 (M + H)+ 1097 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(propan-2-yl)-1H- ESI(+)) pyrazol-3-yl]acetyl}piperidin-4-yl)benzamide m/e 485 (M + H)+ 1098 4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 479 (M + H)+ 1099 Example 1099 ESI(+)) N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyl-5,6,7,8- m/e 497 tetrahydroimidazo[1,5-a]pyridin-1-yl)carbonyl]piperidin-4- (M + H)+ yl}benzamide 1100 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxy-5- ESI(+)) methylpyridin-2-yl)carbonyl]piperidin-4-yl}benzamide m/e 484 (M + H)+ 1101 4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 497 (M + H)+ 1102 4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 480 (M + H)+ 1103 4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 470 (M + H)+ 1104 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[4-(propan-2- ESI(+)) yl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)benzamide m/e 483 (M + H)+ 1105 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-5-propyl- ESI(+)) 1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}benzamide m/e 485 (M + H)+ 1106 4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-yl)propanoyl]piperidin-4-yl}- ESI(+)) N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 497 (M + H)+ 1107 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2,3-dihydro- ESI(+)) 1-benzofuran-7-yl)carbonyl]piperidin-4-yl}benzamide m/e 495 (M + H)+ 1108 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)-1,3- ESI(+)) thiazol-4-yl]carbonyl}piperidin-4-yl)benzamide m/e 488 (M + H)+ 1109 4-(1-{[1-(difluoromethyl)-5-methyl-1H-pyrazol-3- ESI(+)) yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7- m/e 493 ylmethyl)benzamide (M + H)+ 1110 4-{1-[(4-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 470 (M + H)+ 1111 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazolo[1,5-a]pyridin- ESI(+)) 2-ylcarbonyl)piperidin-4-yl]benzamide m/e 479 (M + H)+ 1112 4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2- ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 479 (M + H)+ 1113 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)-1,3- ESI(+)) oxazol-4-yl]carbonyl}piperidin-4-yl)benzamide m/e 472 (M + H)+ 1114 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxy-5- ESI(+)) methylpyridin-3-yl)carbonyl]piperidin-4-yl}benzamide m/e 484 (M + H)+ 1115 4-{1-[(5,6-dimethoxypyridin-2-yl)carbonyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 500 (M + H)+ 1116 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2H-indazol- ESI(+)) 4-yl)carbonyl]piperidin-4-yl}benzamide m/e 493 (M + H)+ 1117 4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]piperidin-4-yl}-N- ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 502 (M + H)+ 1118 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2H-indazol- ESI(+)) 6-yl)carbonyl]piperidin-4-yl}benzamide m/e 493 (M + H)+ 1119 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-indazol- ESI(+)) 4-yl)carbonyl]piperidin-4-yl}benzamide m/e 493 (M + H)+ 1120 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2- ESI(+)) (trifluoromethyl)furan-3-yl]carbonyl}piperidin-4-yl)benzamide m/e 497 (M + H)+ - The title compound was prepared as described in Example 215, substituting 3-methoxypropanoyl chloride for 2-cyclopentylacetyl chloride in Example 215B. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.08 (t, J=5.8 Hz, 1H), 8.46 (dd, J=1.9, 0.9 Hz, 1H), 7.94 (dd, J=1.2, 0.6 Hz, 1H), 7.91-7.85 (m, 2H), 7.79-7.73 (m, 2H), 7.56-7.49 (m, 2H), 7.43-7.39 (m, 2H), 7.38-7.33 (m, 2H), 7.20 (dd, J=9.2, 1.7 Hz, 1H), 5.00 (bs, 2H), 4.45 (d, J=5.8 Hz, 2H), 3.54 (t, J=6.2 Hz, 2H), 3.17 (s, 3H), 2.43-2.35 (m, 2H); MS (ESI(+)) m/e 468 (M+H)+.
- A solution of 5-bromothiophene-2-carboxylic acid (1.279 g, 6.18 mmol), imidazo[1,2-a]pyridin-7-ylmethanamine (1 g, 6.79 mmol), 1-hydroxybenzotriazole hydrate (1.041 g, 6.79 mmol) and N-methylmorpholine (1.698 ml, 15.44 mmol) in dimethylformamide (20 ml) at room temperature was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.131 g, 11.12 mmol). The mixture was stirred overnight and poured into a gently stirred round-bottom flask containing water (100 ml) and ethyl acetate (30 ml). The resulting bilayer suspension was stirred for several minutes, filtered and washed with water then minimal ethyl acetate to give the title compound after drying.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate.
- The title compound was prepared as described in Example 52A, substituting acetyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.13-9.06 (m, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.88 (s, 1H), 7.72 (d, J=3.9 Hz, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.38 (s, 1H), 7.15 (t, J=4.2 Hz, 1H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.28-6.21 (m, 1H), 4.46 (d, J=5.9 Hz, 2H), 4.15-4.04 (m, 2H), 3.61 (dt, J=11.3, 5.6 Hz, 2H), 2.63-2.35 (m, 2H), 2.07-1.99 (m, 3H); MS (ESI)(+)) m/e 381 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting methanesulfonyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.15-9.07 (m, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.88 (s, 1H), 7.73 (d, J=3.9 Hz, 1H), 7.51 (s, 1H), 7.38 (bs, 1H), 7.17 (d, J=3.9 Hz, 1H), 6.83 (d, J=7.0 Hz, 1H), 6.28 (bs, 1H), 4.49-4.43 (m, 2H), 3.88-3.82 (m, 2H), 3.29-3.07 (m, 2H), 2.93 (s, 3H), 2.65-2.41 (m, 2H); MS (ESI)(+)) m/e 417 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting cyclopropyl sulfonyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.10 (t, J=6.0 Hz, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.88 (s, 1H), 7.73 (d, J=3.9 Hz, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.38 (s, 1H), 7.17 (d, J=3.9 Hz, 1H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.28 (bs, 1H), 4.46 (d, J=5.9 Hz, 2H), 3.95-3.89 (m, 2H), 3.43 (t, J=5.7 Hz, 2H), 2.73-2.56 (m, 3H), 1.26-0.89 (m, 4H); MS (ESI)(+)) m/e 443 (M+H)+.
- A solution of 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide (84 mg, 0.25 mmol), (R)-4-isopropyloxazolidin-2-one (32 mg, 0.25 mmol), N,N-dimethylethane-1,2-diamine (2 mg, 0.025 mmol), copper(I) iodide (5 mg, 0.025 mmol) and potassium carbonate (121 mg, 0.88 mmol) in dioxane (1 ml) was stirred at 110° C. overnight. Concentration and reverse phase chromatography provided the title compound. 1H NMR (400 MHz, methanol-d4) δ ppm 9.13 (t, J=5.3 Hz, 1H), 8.74 (d, J=5.5 Hz, 1H), 8.17 (s, 1H), 7.99 (s, 1H), 7.79 (s, 1H), 7.62 (d, J=4.1 Hz, 1H), 7.47 (d, J=7.0 Hz, 1H), 6.77 (d, J=4.2 Hz, 1H), 4.72 (s, 2H), 4.61-4.42 (m, 3H), 2.46 (ddd, J=10.2, 6.9, 3.5 Hz, 1H), 1.00 (d, J=7.0 Hz, 3H), 0.85 (d, J=6.8 Hz, 3H); (APCI(+)) m/e 385 (M+H)+.
- The title compound was prepared as described in Example 1B, substituting tert-butyl 4-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for N-isopentyl-4-nitrobenzamide.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and methoxyacetic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.39 (d, J=7.0 Hz, 1H), 7.79 (s, 1H), 7.60 (d, J=3.8 Hz, 1H), 7.53 (d, J=1.3 Hz, 1H), 7.44 (s, 1H), 6.96 (d, J=3.8 Hz, 1H), 6.92 (dd, J=7.1, 1.2 Hz, 1H), 4.58 (bs, 2H), 3.85-3.76 (m, 2H), 3.03 (tt, J=11.8, 3.8 Hz, 1H), 2.97-2.82 (m, 5H), 2.18-2.09 (m, 2H), 1.96 (s, 1H), 1.86-1.71 (m, 2H); MS (ESI(+)) m/e 413 (M+H)+.
-
TABLE 14 The following Examples were prepared essentially as described in Example 257, substituting the appropriate carboxylic acid in Example 257C. Ex Name MS 258 5-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)thiophene-2-carboxamide m/e 383 (M + H)+ 259 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2- (ESI(+)) methylpropanoyl)piperidin-4-yl]thiophene-2-carboxamide m/e 411 (M + H)+ 260 5-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)thiophene-2-carboxamide m/e 409 (M + H)+ 261 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3- (ESI(+)) ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide m/e 439 (M + H)+ 262 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4- (ESI(+)) ylacetyl)piperidin-4-yl]thiophene-2-carboxamide m/e 467 (M + H)+ 263 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3- (ESI(+)) methylbutanoyl)piperidin-4-yl]thiophene-2-carboxamide m/e 425 (M + H)+ 264 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(1,2-oxazol-5- (ESI(+)) ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide m/e 436 (M + H)+ 879 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-methyl-2-(piperazin- (ESI(+)) 1-yl)propanoyl]piperidin-4-yl}thiophene-2-carboxamide m/e 495 (M + H)+ 887 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)thiophene-2-carboxamide m/e 481 (M + H)+ 888 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)thiophene-2-carboxamide m/e 481 (M + H)+ - The title compound was prepared as described in Example 250, substituting 5-(hydroxymethyl)oxazolidin-2-one for (R)-4-isopropyloxazolidin-2-one. 1H NMR (400 MHz, methanol-d4) δ ppm 9.10 (s, 1H), 8.74 (d, J=7.0 Hz, 1H), 8.17 (d, J=2.0 Hz, 1H), 7.98 (d, J=2.1 Hz, 1H), 7.78 (s, 1H), 7.60 (d, J=4.2 Hz, 1H), 7.52-7.41 (m, 1H), 6.60 (d, J=4.2 Hz, 1H), 4.84 (s, 1H), 4.71 (d, J=4.2 Hz, 2H), 4.16 (t, J=9.1 Hz, 1H), 3.98 (dd, J=8.9, 6.2 Hz, 1H), 3.88 (dd, J=12.7, 3.0 Hz, 1H), 3.69 (dd, J=12.7, 3.6 Hz, 1H); (APCI(+)) m/e 373 (M+H)+.
- The title compound was prepared as described in Example 250, substituting (R)-5-hydroxyoxazolidin-2-one for (R)-4-isopropyloxazolidin-2-one. 1H NMR (400 MHz, methanol-d4) δ ppm 9.10 (t, J=6.1 Hz, 1H), 8.73 (d, J=6.9 Hz, 1H), 8.16 (d, J=1.8 Hz, 1H), 7.98 (d, J=2.0 Hz, 1H), 7.78 (s, 1H), 7.61 (d, J=4.2 Hz, 1H), 7.46 (d, J=7.7 Hz, 1H), 6.68 (d, J=4.2 Hz, 1H), 4.71 (s, 2H), 4.62 (t, J=5.7 Hz, 1H), 4.15 (dd, J=10.9, 5.3 Hz, 1H), 3.83 (d, J=10.9 Hz, 1H), 2.97 (dd, J=17.7, 6.2 Hz, 1H), 2.50 (d, J=18.2 Hz, 1H); (APCI(+)) m/e 357 (M+H)+.
- The title compound was prepared as described in Example 250, substituting (S)-5-hydroxyoxazolidin-2-one for (R)-4-isopropyloxazolidin-2-one. 1H NMR (400 MHz, methanol-d4) δ ppm 9.10 (t, J=5.7 Hz, 1H), 8.74 (d, J=7.0 Hz, 1H), 8.17 (d, J=2.0 Hz, 1H), 7.98 (d, J=2.1 Hz, 1H), 7.78 (s, 1H), 7.61 (d, J=4.2 Hz, 1H), 7.46 (d, J=7.0 Hz, 1H), 6.68 (d, J=4.2 Hz, 1H), 4.71 (s, 2H), 4.62 (t, J=5.7 Hz, 1H), 4.15 (dd, J=10.9, 5.3 Hz, 1H), 3.83 (d, J=11.0 Hz, 1H), 2.97 (dd, J=17.6, 6.2 Hz, 1H), 2.50 (d, J=16.8 Hz, 1H); (APCI(+)) m/e 357 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting methanesulfonyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, methanol-d4) δ ppm 8.39 (d, J=7.0 Hz, 1H), 7.79 (s, 1H), 7.60 (d, J=3.8 Hz, 1H), 7.53 (d, J=1.3 Hz, 1H), 7.44 (s, 1H), 6.96 (d, J=3.8 Hz, 1H), 6.92 (dd, J=7.1, 1.2 Hz, 1H), 4.58 (bs, 2H), 3.85-3.76 (m, 2H), 3.03 (tt, J=11.8, 3.8 Hz, 1H), 2.97-2.82 (m, 5H), 2.18-2.09 (m, 2H), 1.96 (s, 1H), 1.86-1.71 (m, 2H); MS (ESI(+)) m/e 419 (M+H)+.
- The title compound was prepared as described in Example 1C, substituting tert-butyl 4-aminophenylcarbamate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-6-ylmethanamine for imidazo[1,2-a]pyridin-6-amine.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(3-(imidazo[1,2-a]pyridin-6-ylmethyl)ureido)phenylcarbamate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 1-(4-aminophenyl)-3-(imidazo[1,2-a]pyridin-6-ylmethyl)urea for 3-methylbutan-1-amine and 4-methylpentanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.70 (s, 1H), 8.50 (s, 1H), 8.43 (s, 1H), 7.94 (s, 1H), 7.53 (m, 2H), 7.43 (m, 2H), 7.30 (m, 2H), 7.21 (dd, J=9.2, 1.7 Hz, 1H), 6.61 (t, J=5.9 Hz, 1H), 4.28 (d, J=5.8 Hz, 2H), 2.26 (t, J=7.6 Hz, 2H), 1.60-1.40 (m, 3H), 0.89 (d, J=6.4 Hz, 6H); MS (ESI(+)) m/e 380 (M+H)+.
-
TABLE 15 The following Examples were prepared essentially as described in Example 274, substituting the appropriate carboxylic acid in Example 274C. Ex Name 1H NMR MS 275 3-cyclopentyl-N- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.69 (s, (ESI(+)) (4-{[(imidazo[1,2- 1H), 8.48 (s, 1H), 8.43 (s, 1H), 7.94 (s, 1H), m/e 406 a]pyridin-6- 7.53 (m, 2H), 7.43 (m, 2H), 7.30 (m, 2H), 7.20 (M + H)+ ylmethyl)carba- (dd, J = 9.2, 1.7 Hz, 1H), 6.60 (t, J = 5.9 Hz, moyl]amino}phenyl) 1H), 4.28 (d, J = 5.8 Hz, 2H), 2.26 (t, J = 7.6 propanamide Hz, 2H), 1.75 (m, 3H), 1.66-1.39 (m, 6H), 1.08 (m, 2H) 276 N-(4- 1H NMR (500 MHz, DMSO-d6) δ ppm 9.36 (s, (ESI(+)) {[(imidazo[1,2- 1H), 8.53 (s, 1H), 8.43 (s, 1H), 7.94 (s, 1H), m/e 382 a]pyridin-6- 7.53 (m, 2H), 7.49 (m, 2H), 7.33 (m, 2H), 7.21 (M + H)+ ylmethyl)carba- (dd, J = 9.2, 1.7 Hz, 1H), 6.62 (t, J = 5.9 Hz, moyl]amino}phenyl)- 1H), 4.28 (d, J = 5.9 Hz, 2H), 3.97 (s, 2H), 3.67 2-(propan-2- (m, 1H), 1.16 (d, J = 6.1 Hz, 6H) yloxy)acetamide 277 N-(4- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.74 (s, (ESI(+)) {[(imidazo[1,2- 1H), 8.50 (s, 1H), 8.44 (d, J = 1.5 Hz, 1H), 7.96 m/e 394 a]pyridin-6- (s, 1H), 7.54 (m, 2H), 7.44 (m, 2H), 7.31 (m, (M + H)+ ylmethyl)carba- 2H), 7.22 (dd, J = 9.2, 1.7 Hz, 1H), 6.61 (t, J = moyl]amino}phenyl)- 5.9 Hz, 1H), 4.28 (d, J = 5.9 Hz, 2H), 4.12 (m, 2-(tetrahydrofuran- 1H), 3.74 (m, 1H), 3.60 (m, 1H), 2.47 (m, 1H), 2-yl)acetamide 2.39 (m, 1H), 1.98 (m, 1H), 1.81 (m, 2H), 1.49 (m, 1H) 278 N-(4- 1H NMR (500 MHz, DMSO-d6) δ ppm 9.72 (s, (ESI(+)) {[(imidazo[1,2- 1H), 8.50 (s, 1H), 8.43 (s, 1H), 7.94 (s, 1H), m/e 408 a]pyridin-6- 7.53 (m, 2H), 7.43 (m, 2H), 7.31 (m, 2H), 7.21 (M + H)+ ylmethyl)carba- (dd, J = 9.2, 1.7 Hz, 1H), 6.60 (t, J = 5.9 Hz, moyl]amino}phenyl)- 1H), 4.28 (d, J = 5.9 Hz, 2H), 3.82 (m, 2H), 2-(tetrahydro- 3.29 (m, 2H), 2.20 (d, J = 7.1 Hz, 2H), 2.01 (m, 2H-pyran-4- 1H), 1.57 (m, 2H), 1.25 (m, 2H) yl)acetamide 279 N-(4- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.73 (s, (ESI(+)) {[(imidazo[1,2- 1H), 8.49 (s, 1H), 8.42 (s, 1H), 7.94 (s, 1H), m/e 414 a]pyridin-6- 7.53 (m, 2H), 7.42 (m, 2H), 7.35-7.15 (m, 8H), (M + H)+ ylmethyl)carba- 6.60 (t, J = 5.9 Hz, 1H), 4.28 (d, J = 5.8 Hz, moyl]amino}phenyl)- 2H), 2.89 (t, J = 7.3 Hz, 2H), 2.57 (t, J = 5.7 Hz, 3-phenylpropanamide 2H) 280 N-(4- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.69 (s, (ESI(+)) {[(imidazo[1,2- 1H), 8.52 (s, 1H), 8.47 (d, J = 7.0 Hz, 1H), 7.87 m/e 380 a]pyridin-7- (s, 1H), 7.50 (bs, 1H), 7.42 (m, 2H), 7.37 (s, (M + H)+ ylmethyl)carba- 1H), 7.30 (m, 2H), 6.82 (dd, J = 7.0, 1.5 Hz, moyl]amino}phenyl)- 1H), 6.63 (t, J = 6.0 Hz, 1H), 4.31 (d, J = 5.9 4-methylpentanamide Hz, 2H), 2.25 (t, J = 7.6 Hz, 2H), 1.60-1.41 (m, 3H), 0.88 (d, J = 6.4 Hz, 6H) 281 3-cyclopentyl-N- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.69 (s, (ESI(+)) (4-{[(imidazo[1,2- 1H), 8.53 (s, 1H), 8.48 (d, J = 6.9 Hz, 1H), 7.88 m/e 406 a]pyridin-7- (bs, 1H), 7.52 (bs, 1H), 7.44 (m, 2H), 7.37 (s, (M + H)+ ylmethyl)carba- 1H), 7.31 (m, 2H), 6.83 (dd, J = 6.9, 1.4 Hz, moyl]amino}phenyl) 1H), 6.64 (t, J = 6.0 Hz, 1H), 4.32 (d, J = 5.9 propanamide Hz, 2H), 2.27 (t, J = 7.6 Hz, 2H), 1.74 (m, 3H), 1.65-1.40 (m, 6H), 1.09 (m, 2H) 282 N-(4- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.37 (s, (ESI(+)) {[(imidazo[1,2- 1H), 8.59 (s, 1H), 8.49 (m, 1H), 7.89 (s, 1H), m/e 382 a]pyridin-7- 7.50 (m, 3H), 7.39 (s, 1H), 7.34 (m, 2H), 6.84 (M + H)+ ylmethyl)carba- (dd, J = 6.9, 1.6 Hz, 1H), 6.68 (t, J = 6.0 Hz, moyl]amino}phenyl)- 1H), 4.33 (d, J = 6.0 Hz, 2H), 3.98 (s, 2H), 3.67 2-(propan-2- (m, 1H), 1.16 (d, J = 6.1 Hz, 6H) yloxy)acetamide 283 N-(4- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.73 (s, (ESI(+)) {[(imidazo[1,2- 1H), 8.54 (s, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 m/e 394 a]pyridin-7- (s, 1H), 7.51 (s, 1H), 7.44 (m, 2H), 7.38 (bs, (M + H)+ ylmethyl)carba- 1H), 7.32 (m, 2H), 6.83 (dd, J = 6.9, 1.6 Hz, moyl]amino}phenyl)- 1H), 6.65 (t, J = 6.0 Hz, 1H), 4.32 (d, J = 5.9 2-(tetrahydrofuran- Hz, 2H), 4.16 (m, 1H), 3.76 (m, 1H), 3.60 (m, 2-yl)acetamide 1H), 2.50 (m, 1H), 2.39 (m, 1H), 1.99 (m, 1H), 1.83 (m, 2H), 1.53 (m, 1H) 284 N-(4- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.72 (s, (ESI(+)) {[(imidazo[1,2- 1H), 8.53 (s, 1H), 8.48 (d, J = 6.9 Hz, 1H), 7.88 m/e 408 a]pyridin-7- (bs, 1H), 7.51 (bs, 1H), 7.44 (m, 2H), 7.38 (bs, (M + H)+ ylmethyl)carba- 1H), 7.32 (m, 2H), 6.83 (m, 1H), 6.65 (m, 1H), moyl]amino}phenyl)- 4.32 (m, 2H), 3.82 (m, 2H), 3.33 (m, 2H), 2.20 2-(tetrahydro- (d, J = 7.1 Hz, 2H), 1.97 (m, 1H), 1.58 (m, 2H), 2H-pyran-4- 1.23 (m, 2H) yl)acetamide 285 N-(4- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.74 (s, (ESI(+)) {[(imidazo[1,2- 1H), 8.54 (s, 1H), 8.49 (d, J = 6.9 Hz, 1H), 7.89 m/e 414 a]pyridin-7- (bs, 1H), 7.52 (bs, 1H), 7.42 (m, 3H), 7.35- (M + H)+ ylmethyl)carba- 7.22 (m, 6H), 7.17 (m, 1H), 6.84 (d, J = 7.6 Hz, moyl]amino}phenyl)- 1H), 6.65 (t, J = 6.0 Hz, 1H), 4.32 (d, J = 5.9 3-phenylpropanamide Hz, 2H), 2.90 (t, J = 7.7 Hz, 2H), 2.58 (t, J = 7.7 Hz, 2H) - The title compound was prepared as described in Example 1C, substituting 4-bromo-2-fluoroaniline for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromo-2-fluorophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.53-8.46 (m, 2H), 8.09 (t, J=8.7 Hz, 1H), 7.91-7.88 (m, 1H), 7.54-7.50 (m, 1H), 7.42-7.37 (m, 1H), 7.33-7.24 (m, 1H), 7.21-7.08 (m, 2H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 6.17-6.10 (m, 1H), 4.35 (d, J=5.8 Hz, 2H), 4.01-3.94 (m, 2H), 3.55-3.47 (m, 2H), 2.46-2.36 (m, 2H), 1.42 (s, 9H); MS (ESI(+)) m/e 466 (M+H)+.
- (S)-Tert-butyl 3-hydroxypyrrolidine-1-carboxylate (10 g, 53.4 mmol) was dissolved in 1-fluoro-4-nitrobenzene (13.94 g, 99 mmol). An aqueous solution of 5.9N potassium hydroxide (77 ml, 452 mmol) was added followed by addition of tetrabutylammonium bromide (2.238 g, 6.94 mmol). The reaction mixture was stirred at 40° C. for 24 hours and then cooled, diluted with water and extracted with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered and concentrated to give the title compound.
- The title compound was prepared as described in Example 1B, substituting (S)-tert-butyl 3-(4-nitrophenoxy)pyrrolidine-1-carboxylate for N-isopentyl-4-nitrobenzamide.
- The title compound was prepared as described in Example 1C, substituting (S)-tert-butyl 3-(4-aminophenoxy)pyrrolidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.51-8.44 (m, 2H), 7.88-7.86 (m, 1H), 7.53-7.49 (m, 1H), 7.40-7.27 (m, 3H), 6.86-6.80 (m, 3H), 6.63 (t, J=6.0 Hz, 1H), 4.93-4.84 (m, 1H), 4.32 (d, J=6.0 Hz, 2H), 3.55-3.28 (m, 4H), 2.16-1.94 (m, 2H), 1.42-1.36 (m, 9H); MS (ESI(+)) m/e 452 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(tert-butoxycarbonylamino)-3-fluorobenzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.26 (s, 1H), 9.08 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.91-7.78 (m, 2H), 7.76-7.68 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (bs, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.49 (d, J=5.8 Hz, 2H), 1.48 (s, 9H); MS (ESI(+)) m/e 385 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 4-bromoaniline.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiazol-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1,2,3,6-tetrahydropyridin-4-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.27 (t, J=5.9 Hz, 1H), 8.50 (d, J=7.1 Hz, 1H), 8.41 (s, 1H), 7.89 (s, 1H), 7.38-7.56 (m, 7H), 6.85 (dd, J=6.8, 1.7 Hz, 1H), 6.56-6.89 (m, 1H), 4.49 (d, J=5.8 Hz, 2H), 4.08-4.40 (m, 2H), 3.74-3.92 (m, 1H), 3.44-3.66 (m, 1H), 2.66 (s, 2H); MS (ESI(+)) m/e 444 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-bromobenzoic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 51A, substituting 1-(2-hydroxy-2-methylpropyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 4-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.05 (t, J=5.9 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.19 (d, J=0.8 Hz, 1H), 7.97 (d, J=0.7 Hz, 1H), 7.95-7.86 (m, 3H), 7.73-7.66 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.42-7.37 (m, 1H), 6.87 (dd, J=7.0, 1.7 Hz, 1H), 4.73 (s, 1H), 4.51 (d, J=5.8 Hz, 2H), 4.04 (s, 2H), 1.10 (s, 6H); MS (ESI(+)) m/e 390 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.14 (t, J=6.0 Hz, 1H), 8.50 (dd, J=7.1, 0.7 Hz, 1H), 7.91-7.88 (m, 1H), 7.84 (d, J=3.9 Hz, 1H), 7.72 (dt, J=8.3, 2.4 Hz, 2H), 7.57 (d, J=3.9 Hz, 1H), 7.53 (d, J=1.2 Hz, 1H), 7.49-7.33 (m, 4H), 6.86 (dd, J=7.0, 1.7 Hz, 1H), 4.50 (d, J=5.8 Hz, 2H); MS (ESI(+)) m/e 334 (M+H).
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.06 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.87 (m, 3H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (m, 3H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.50 (d, J=5.9 Hz, 2H), 3.72 (dd, J=10.3, 7.5 Hz, 1H), 3.47 (m, 2H), 3.20 (m, 2H), 2.21 (m, 1H), 1.97 (m, 1H), 1.41 (m, 9H); (ESI(+)) m/e 421 (M+H)+.
- The title compound was prepared as described in Example 1C, substituting tert-butyl 3-(4-aminophenyl)pyrrolidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.61 (s, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.88 (d, J=1.1 Hz, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.36 (m, 3H), 7.14 (m, 2H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 6.69 (t, J=6.0 Hz, 1H), 4.33 (d, J=6.0 Hz, 2H), 3.65 (dd, J=10.2, 7.5 Hz, 1H), 3.46 (m, 1H), 3.21 (m, 2H), 3.09 (m, 1H), 2.12 (m, 1H), 1.89 (m, 1H), 1.41 (m, 9H); (ESI(+)) m/e 436 (M+H)+.
- The title compound was prepared as described in Example 1C, substituting tert-butyl 4-aminophenylcarbamate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)phenylcarbamate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- In a 4 mL vial was mixed 1-(4-aminophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea (50 mg, 0.178 mmol) in anhydrous tetrahydrofuran (2 mL). To this mixture at room temperature was added 60% sodium hydride (24.88 mg, 0.622 mmol). The reaction was stirred about 30 minutes and biphenyl-2-sulfonyl chloride (53.9 mg, 0.213 mmol) was added. The reaction mixture stirred overnight at room temperature and was quenched with saturated ammonium chloride and water. The aqueous solution was extracted with dichloromethane and 10% methanol/dichloromethane. The organic layers were combined, concentrated and purified by normal phase chromatography to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.74 (bs, 1H), 8.56 (s, 1H), 8.47 (dd, J=6.9, 0.9 Hz, 1H), 7.95 (dd, J=7.8, 1.4 Hz, 1H), 7.87 (dd, J=1.2, 0.6 Hz, 1H), 7.62 (m, 1H), 7.54 (m, 1H), 7.51 (m, 1H), 7.38 (m, 4H), 7.30-7.20 (m, 5H), 6.82 (m, 3H), 6.66 (t, J=6.0 Hz, 1H), 4.30 (d, J=6.0 Hz, 2H); (ESI(+)) m/e 498 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3,6-dihydropyridine-1(2H)-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 1-(2-fluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, methanol-d4) δ ppm 8.74 (d, J=7.0 Hz, 1H), 8.19-8.15 (m, 1H), 8.00-7.96 (m, 1H), 7.92 (t, J=8.5 Hz, 1H), 7.81-7.77 (m, 1H), 7.50-7.44 (m, 1H), 7.28-7.16 (m, 2H), 6.17-6.11 (m, 1H), 4.61 (bs, 2H), 4.30-4.15 (m, 2H), 3.79 (t, J=5.7 Hz, 2H), 3.08-2.90 (m, 1H), 2.62-2.45 (m, 2H), 1.17-1.08 (m, 6H); MS (ESI(+)) m/e 436 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 1-(2-fluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 3-methylbutan-1-amine and tetrahydrofuran-2-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, methanol-d4) δ ppm 8.74 (d, J=7.0 Hz, 1H), 8.17 (d, J=2.2 Hz, 1H), 7.98 (d, J=2.2 Hz, 1H), 7.92 (t, J=8.5 Hz, 1H), 7.80 (bs, 1H), 7.47 (dd, J=7.0, 1.5 Hz, 1H), 7.28-7.16 (m, 2H), 6.17-6.09 (m, 1H), 4.84-4.70 (m, 1H), 4.61 (bs, 2H), 4.34-4.12 (m, 2H), 4.01-3.68 (m, 4H), 2.67-2.47 (m, 2H), 2.29-1.88 (m, 4H); MS (ESI(+)) m/e 464 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-amine for 3-methylbutan-1-amine and 2-(4-bromophenyl)acetic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 2-(4-bromophenyl)-N-(imidazo[1,2-a]pyridin-6-yl)acetamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.25 (s, 1H), 9.20-9.16 (m, 1H), 7.98-7.94 (m, 1H), 7.58-7.48 (m, 2H), 7.44-7.36 (m, 2H), 7.35-7.28 (m, 2H), 7.16 (dd, J=9.6, 2.0 Hz, 1H), 6.16-6.09 (m, 1H), 4.05-3.94 (m, 2H), 3.66 (s, 2H), 3.53 (t, J=5.7 Hz, 2H), 2.49-2.40 (m, 2H), 1.42 (s, 9H); MS (ESI(+)) m/e 433 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 4-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.04 (t, J=5.9 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 8.27 (s, 1H), 8.00-7.86 (m, 4H), 7.69 (d, J=8.4 Hz, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (d, J=1.5 Hz, 1H), 6.87 (dd, J=7.0, 1.7 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 3.94 (d, J=7.1 Hz, 2H), 2.15 (dp, J=13.6, 6.8 Hz, 1H), 0.87 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 374 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 2-(3-isopropoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.04 (t, J=6.0 Hz, 1H), 8.49 (dd, J=7.0, 0.8 Hz, 1H), 8.19 (d, J=0.4 Hz, 1H), 7.89 (d, J=0.8 Hz, 1H), 7.86 (d, J=0.5 Hz, 1H), 7.75 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.24 (d, J=3.9 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.48 (d, J=5.8 Hz, 2H), 4.13 (d, J=6.6 Hz, 2H), 3.09-2.83 (m, 4H), 2.47-2.40 (m, 1H), 2.14-1.96 (m, 1H), 1.88-1.69 (m, 1H), 1.69-1.54 (m, 1H), 1.37-1.14 (m, 1H).
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1,2,3,6-tetrahydropyridin-4-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and tetrahydro-2H-pyran-4-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.26 (t, J=5.9 Hz, 1H), 8.50 (d, J=6.8 Hz, 1H), 8.40 (s, 1H), 7.89 (s, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.42 (s, 1H), 6.84 (dd, J=7.1, 1.7 Hz, 1H), 6.72-6.79 (m, 1H), 4.49 (d, J=5.8 Hz, 2H), 4.32 (s, 1H), 4.16 (s, 1H), 3.81-3.89 (m, 2H), 3.73 (s, 2H), 3.36-3.47 (m, 1H), 2.83-3.05 (m, 1H), 2.65 (s, 1H), 2.38-2.54 (m, 2H), 1.50-1.69 (m, 4H); MS (ESI(+)) m/e 452 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1,2,3,6-tetrahydropyridin-4-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.26 (t, J=5.9 Hz, 1H), 8.50 (d, J=7.1 Hz, 1H), 8.40 (s, 1H), 7.89 (s, 1H), 7.53 (s, 1H), 7.42 (s, 1H), 6.84 (dd, J=7.1, 1.7 Hz, 1H), 6.76 (s, 1H), 4.49 (d, J=5.8 Hz, 2H), 4.29 (s, 1H), 4.16 (s, 1H), 3.62-3.74 (m, 2H), 2.81-3.03 (m, 1H), 2.60-2.69 (m, 1H), 2.50-2.58 (m, 1H), 1.02 (d, J=6.4 Hz, 6H); MS (ESI(+)) m/e 410 (M+H)+.
- To a stirred solution of (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (1 g, 5.34 mmol) in tetrahydrofuran (38.1 ml) was added benzyl 4-hydroxybenzoate (1.341 g, 5.87 mmol) and triphenylphosphine polymer bound (4.45 g, 8.01 mmol). The reaction mixture was cooled to 0° C. and a solution of (E)-diisopropyl diazene-1,2-dicarboxylate (1.367 ml, 6.94 mmol) in tetrahydrofuran (5 mL) was added dropwise over 15 minutes. The reaction was allowed to stir at room temperature for 16 hours and the mixture was filtered. The solids were washed with dichloromethane, and the combined filtrates were concentrated and purified by normal phase chromatography to give the title compound.
- The title compound was prepared as described in Example 1B, substituting (R)-tert-butyl 3-(4-(benzyloxycarbonyl)phenoxy)pyrrolidine-1-carboxylate for N-isopentyl-4-nitrobenzamide.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and (S)-4-(1-(tert-butoxycarbonyl)pyrrolidin-3-yloxy)benzoic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 28A, substituting (S)-tert-butyl 3-(4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenoxy)pyrrolidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting (S)—N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yloxy)benzamide for 3-methylbutan-1-amine and (S)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6, Temp=90° C.) δ ppm 8.67-8.59 (m, 1H), 8.41 (d, J=6.9 Hz, 1H), 7.90-7.84 (m, 2H), 7.81 (s, 1H), 7.50-7.46 (m, 1H), 7.38 (s, 1H), 7.03-6.97 (m, 2H), 6.83 (dd, J=6.9, 1.7 Hz, 1H), 5.17-5.04 (m, 1H), 4.49 (d, J=5.9 Hz, 2H), 3.91-3.36 (m, 5H), 2.31-1.98 (m, 2H), 1.63-1.49 (m, 1H), 1.38-1.23 (m, 1H), 1.00 (d, J=6.7 Hz, 3H), 0.89-0.74 (m, 3H); MS (ESI(+)) m/e 421 (M+H)+.
-
TABLE 16 The following Examples were prepared essentially as described in Example 321, substituting the appropriate carboxylic acid in Example 321E. Ex Name MS 339 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3R)- (ESI(+)) tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide m/e 435 (M + H)+ 340 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2R)- (ESI(+)) tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide m/e 435 (M + H)+ 341 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)- (ESI(+)) tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide m/e 435 (M + H)+ 342 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H- (ESI(+)) pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}benzamide m/e 449 (M + H)+ 343 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H- (ESI(+)) pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}benzamide m/e 463 (M + H)+ 346 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3S)- (ESI(+)) tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide m/e 435 (M + H)+ 347 4-{[(3S)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}-N- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 419 (M + H)+ 348 4-{[(3S)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}- (ESI(+)) N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 423 (M + H)+ 349 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(3-methoxy-2- (ESI(+)) methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide m/e 437 (M + H)+ 350 4-{[(3S)-1-butanoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 407 (M + H)+ 351 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(2- (ESI(+)) methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide m/e 407 (M + H)+ 352 4-{[(3S)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}-N- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 405 (M + H)+ 353 4-{[(3S)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)benzamide m/e 441 (M + H)+ 354 4-{[(3S)-1-(3-hydroxy-3-methylbutanoyl)pyrrolidin-3-yl]oxy}-N- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)benzamide m/e 437 (M + H)+ - The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-amine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.36 (s, 1H), 8.47 (d, J=7.3 Hz, 1H), 8.15-8.10 (m, 1H), 7.94-7.87 (m, 2H), 7.83 (s, 1H), 7.50-7.40 (m, 3H), 7.24 (dd, J=7.3, 2.1 Hz, 1H), 4.16-4.05 (m, 2H), 2.94-2.66 (m, 3H), 1.84-1.73 (m, 2H), 1.65-1.41 (m, 11H); MS (ESI(+)) m/e 421 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-amine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.27 (s, 1H), 9.36-9.31 (m, 1H), 8.03 (s, 1H), 7.95-7.88 (m, 2H), 7.60-7.52 (m, 2H), 7.47-7.35 (m, 3H), 4.15-4.04 (m, 2H), 2.95-2.66 (m, 3H), 1.83-1.73 (m, 2H), 1.65-1.45 (m, 2H), 1.42 (s, 9H); MS (ESI(+)) m/e 421 (M+H)+.
- Butyllithium (6.16 ml, 15.41 mmol) was added dropwise to a stirred solution of diisopropylamine (1.919 ml, 13.69 mmol) in tetrahydrofuran (10 ml) at −78° C. The solution was allowed to warm to room temperature and then added dropwise by syringe to a stirred −78° C. solution of thiophene-2-carboxylic acid (0.877 g, 6.85 mmol) in tetrahydrofuran (30 ml). The resulting suspension was stirred for 40 minutes at −78° C. when a solution of 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide (1 g, 5.71 mmol) in tetrahydrofuran (10 ml) was added dropwise. After the addition was complete, the reaction mixture was allowed to warm to room temperature, quenched with saturated ammonium chloride and diluted with a water to dissolve the remaining solids. The aqueous solution was extracted with ethyl acetate, adjusted to pH 2 by addition of 1N aqueous hydrochloric acid and re-extracted with ethyl acetate and methylene chloride. The organic extracts were dried with magnesium sulfate, filtered, concentrated and purified by normal phase chromatography to give the title compound.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(3-(1,1-dimethylethylsulfinamido)oxetan-3-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid.
- 5-(3-(1,1-Dimethylethylsulfinamido)oxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide (432 mg, 1 mmol) in 10 ml methanol was treated with 4N aqueous HCl in dioxane (0.75 ml, 3 mmol) and the mixture was stirred for 2 hours. Concentration provided the title compound.
- The title compound was prepared as described in Example 1A, substituting 5-(3-aminooxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03-9.10 (m, 2H), 8.48 (d, J=7.1 Hz, 1H), 7.89 (s, 1H), 7.71 (d, J=4.0 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.38 (s, 1H), 7.22 (d, J=4.0 Hz, 1H), 6.83 (dd, J=6.9, 1.8 Hz, 1H), 4.80 (d, J=6.7 Hz, 2H), 4.71 (d, J=6.7 Hz, 2H), 4.46 (d, J=6.0 Hz, 2H), 2.40-2.48 (m, 1H), 1.05 (d, J=7.1 Hz, 6H); MS (ESI(+)) m/e 399 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 5-(3-aminooxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.70 (s, 1H), 9.05 (t, J=5.9 Hz, 1H), 8.47 (d, J=6.8 Hz, 1H), 7.87-7.93 (m, 3H), 7.72 (d, J=3.7 Hz, 1H), 7.56-7.62 (m, 1H), 7.48-7.55 (m, 3H), 7.37 (s, 1H), 7.29 (d, J=3.7 Hz, 1H), 6.82 (dd, J=7.1, 1.7 Hz, 1H), 5.01 (d, J=6.8 Hz, 2H), 4.80 (d, J=7.1 Hz, 2H), 4.45 (d, J=5.8 Hz, 2H); MS (ESI(+)) m/e 433 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 5-(3-aminooxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 2-(tetrahydrofuran-3-yl)acetic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.22 (s, 1H), 9.07 (t, J=6.0 Hz, 1H), 8.48 (d, J=7.1 Hz, 1H), 7.89 (s, 1H), 7.71 (d, J=3.6 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.38 (s, 1H), 7.22 (d, J=4.0 Hz, 1H), 6.83 (dd, J=7.1, 1.6 Hz, 1H), 4.81 (d, J=6.7 Hz, 2H), 4.72 (d, J=6.7 Hz, 2H), 4.46 (d, J=6.0 Hz, 2H), 3.56-3.80 (m, 3H), 2.23-2.30 (m, 2H), 1.89-2.04 (m, 1H), 1.45-1.58 (m, 1H); MS (ESI(+)) m/e 441 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 5-(3-aminooxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and pentanoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.11 (s, 1H), 9.05 (t, J=5.9 Hz, 1H), 8.48 (dd, J=7.0, 0.8 Hz, 1H), 7.88 (s, 1H), 7.70 (d, J=4.1 Hz, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.38 (s, 1H), 7.21 (d, J=3.7 Hz, 1H), 6.83 (dd, J=7.1, 1.7 Hz, 1H), 4.80 (d, J=6.8 Hz, 2H), 4.71 (d, J=6.8 Hz, 2H), 4.46 (d, J=5.8 Hz, 2H), 2.17 (t, J=7.5 Hz, 2H), 1.44-1.57 (m, 2H), 1.22-1.37 (m, 2H), 0.84-0.92 (m, 3H); MS (ESI(+)) m/e 413 (M+H)+.
- (R)-Tert-butyl 3-hydroxypyrrolidine-1-carboxylate (10 g, 53.4 mmol) was dissolved in 1-fluoro-4-nitrobenzene (13.94 g, 99 mmol). An aqueous solution of 5.9N potassium hydroxide (77 ml, 452 mmol) was added followed by addition of tetrabutylammonium bromide (2.238 g, 6.94 mmol). The reaction mixture was stirred at 40° C. for 24 hours, cooled, diluted with water and extracted with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered and concentrated to give the title compound.
- The title compound was prepared as described in Example 1B, substituting (R)-tert-butyl 3-(4-nitrophenoxy)pyrrolidine-1-carboxylate for N-isopentyl-4-nitrobenzamide.
- The title compound was prepared as described in Example 1C, substituting (R)-tert-butyl 3-(4-aminophenoxy)pyrrolidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine.
- The title compound was prepared as described in Example 28A, substituting tert-butyl (3S)-3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)pyrrolidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting (R)-1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-(pyrrolidin-3-yloxy)phenyl)urea for 3-methylbutan-1-amine and (S)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.76-8.70 (m, 1H), 8.19-8.12 (m, 1H), 8.00-7.94 (m, 1H), 7.81-7.75 (m, 1H), 7.46 (d, J=7.0 Hz, 1H), 7.34-7.25 (m, 2H), 6.92-6.82 (m, 2H), 5.07-4.95 (m, 1H), 4.58 (bs, 2H), 3.84-3.61 (m, 3H), 3.60-3.45 (m, 1H), 2.67-2.45 (m, 1H), 2.31-2.06 (m, 2H), 1.72-1.57 (m, 1H), 1.50-1.35 (m, 1H), 1.12-1.00 (m, 3H), 0.94-0.85 (m, 3H); MS (ESI(+)) m/e 436 (M+H)+.
-
TABLE 17 The following Examples were prepared essentially as described in Example 328, substituting the appropriate alcohol in Example 328A and the appropriate carboxylic acid in Example 328E. Ex Name MS 329 1-(4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)urea m/e 456 (M + H)+ 330 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(2- (ESI(+)) methylpropanoyl)pyrrolidin-3-yl]oxy}phenyl)urea m/e 422 (M + H)+ 331 1-(4-{[(3R)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 420 (M + H)+ 332 1-(4-{[(3R)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}phenyl)-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 434 (M + H)+ 333 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydro-2H- (ESI(+)) pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)urea m/e 464 (M + H)+ 334 1-(4-{[(3R)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3- (ESI(+)) yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 438 (M + H)+ 335 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2R)- (ESI(+)) tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)phenyl]urea m/e 450 (M + H)+ 336 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2S)- (ESI(+)) tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)phenyl]urea m/e 450 (M + H)+ 337 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1- (ESI(+)) (tetrahydrofuran-3-ylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)urea m/e 450 (M + H)+ 338 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydro-2H- (ESI(+)) pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}phenyl)urea m/e 478 (M + H)+ 689 1-(4-{[(3R)-1-(2-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 474 (M + H)+ 690 1-(4-{[(3R)-1-(3-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 474 (M + H)+ 691 1-(4-{[(3R)-1-(4-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 474 (M + H)+ 692 1-(4-{[(3R)-1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 492 (M + H)+ 693 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[4- (ESI(+)) (trifluoromethyl)benzoyl]pyrrolidin-3-yl}oxy)phenyl]urea m/e 524 (M + H)+ 694 1-(4-{[(3R)-1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 492 (M + H)+ 695 1-(4-{[(3R)-1-(2-chlorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 490 (M + H)+ 696 1-(4-{[(3R)-1-(4-chlorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)urea m/e 490 (M + H)+ - The title compound was prepared as in Example 53B, substituting phenyl(piperazin-1-yl)methanone for 4-cyanobenzylamine and 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.86 (t, J=6.0 Hz, 1H), 8.48 (d, J=6.7 Hz, 1H), 7.90 (s, 1H), 7.89 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.41-7.50 (m, 5H), 7.37 (s, 1H), 6.82 (dd, J=7.1, 1.6 Hz, 1H), 4.43 (d, J=5.6 Hz, 2H), 3.41-3.82 (m, 8H); MS (ESI(+)) m/e 447 (M+H)+.
- The title compound was prepared as in Example 53B, substituting 1-isopropylpiperazine for 4-cyanobenzylamine and 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.80 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.1 Hz, 1H), 7.88 (s, 1H), 7.87 (s, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.37 (s, 1H), 6.81 (dd, J=7.1, 1.7 Hz, 1H), 4.42 (d, J=6.1 Hz, 2H), 3.41-3.48 (m, 4H), 2.64-2.79 (m, 1H), 2.51-2.57 (m, 4H), 0.98 (d, J=6.4 Hz, 6H); MS (ESI(+)) m/e 385 (M+H)+.
- The title compound was prepared as in Example 53B, substituting 1-(2-methoxyethyl)piperazine for 4-cyanobenzylamine and 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.82 (t, J=6.0 Hz, 1H), 8.48 (d, J=6.7 Hz, 1H), 7.88 (s, 1H), 7.88 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 6.81 (dd, J=7.1, 1.6 Hz, 1H), 4.43 (d, J=6.0 Hz, 2H), 3.42-3.48 (m, 6H), 3.24 (s, 3H), 2.51-2.56 (m, 6H); MS (ESI(+)) m/e 401 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(methoxycarbonyl)benzoic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 4B, substituting methyl 4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)benzoate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
- The title compound was prepared as described in Example 1A, substituting 3-methylbutan-1-amine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.15 (t, J=5.8 Hz, 1H), 8.55-8.47 (m, 2H), 8.00-7.84 (m, 5H), 7.54 (dd, J=5.1, 4.1 Hz, 2H), 7.23 (dd, J=9.3, 1.7 Hz, 1H), 4.48 (d, J=5.8 Hz, 2H), 3.30-3.21 (m, 2H), 1.62 (dp, J=13.3, 6.6 Hz, 1H), 1.49-1.37 (m, 2H), 0.91 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 365 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting (S)-(tetrahydrofuran-3-yl)methanamine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.15 (t, J=5.8 Hz, 1H), 8.68 (t, J=5.7 Hz, 1H), 8.49 (bs, 1H), 8.03-7.85 (m, 5H), 7.58-7.50 (m, 2H), 7.23 (dd, J=9.1, 1.7 Hz, 1H), 4.49 (d, J=5.8 Hz, 2H), 3.80-3.56 (m, 4H), 3.48 (dd, J=8.5, 5.2 Hz, 1H), 3.28-3.17 (m, 1H), 2.03-1.87 (m, 1H), 1.68-1.46 (m, 1H), 1.37-1.09 (m, 1H); MS (ESI(+)) m/e 379 (M+H)+.
- The title compound was prepared as described in Example 3A, substituting 1-isocyanato-4-bromobenzene for 1-isocyanato-4-nitrobenzene and imidazo[1,2-a]pyridin-6-ylmethanamine for imidazo[1,2-a]pyridin-6-amine.
- The title compound was prepared as described in Example 51A, substituting 1-propyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-6-ylmethyl)urea for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.59 (s, 1H), 8.44 (s, 1H), 8.04 (s, 1H), 7.95 (s, 1H), 7.76 (s, 1H), 7.57-7.50 (m, 2H), 7.48-7.32 (m, 4H), 7.21 (dd, J=9.2, 1.7 Hz, 1H), 6.65 (t, J=5.9 Hz, 1H), 4.30 (d, J=5.8 Hz, 2H), 4.04 (t, J=6.9 Hz, 2H), 1.87-1.73 (m, 2H), 0.84 (t, J=7.3 Hz, 3H); MS (ESI(+)) m/e 375 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting phenyl boronic acid for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.34 (t, J=5.8 Hz, 1H), 8.56-8.48 (m, 2H), 8.05-7.95 (m, 2H), 7.90 (d, J=0.8 Hz, 1H), 7.60-7.49 (m, 4H), 7.45 (s, 1H), 6.87 (dd, J=7.0, 1.6 Hz, 1H), 4.52 (d, J=5.7 Hz, 2H); MS (ESI(+)) m/e 335 (M+H).
- The title compound was prepared as described in Example 51A, substituting 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-6-ylmethyl)urea for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.59 (s, 1H), 8.44 (d, J=1.6 Hz, 1H), 8.03 (d, J=0.8 Hz, 1H), 7.97-7.93 (m, 1H), 7.77 (d, J=0.8 Hz, 1H), 7.57-7.50 (m, 2H), 7.44-7.35 (m, 4H), 7.21 (dd, J=9.2, 1.7 Hz, 1H), 6.65 (t, J=5.9 Hz, 1H), 4.30 (d, J=5.8 Hz, 2H), 3.90 (d, J=7.2 Hz, 2H), 2.19-2.06 (m, 1H), 0.85 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 389 (M+H)+.
- The title compound was prepared as described in Example 1C, substituting tert-butyl 3-(4-aminophenyl)azetidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.66 (s, 1H), 8.48 (m, 1H), 7.88 (s, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.39 (m, 3H), 7.19 (m, 2H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.70 (t, J=6.0 Hz, 1H), 4.33 (d, J=6.0 Hz, 2H), 4.20 (m, 2H), 3.78 (m, 2H), 3.71 (m, 1H), 1.40 (s, 9H); (ESI(+)) m/e 422 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)benzoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.95 (t, J=6.0 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.88 (m, 3H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 7.06 (m, 2H), 6.85 (dd, J=7.0, 1.6 Hz, 1H), 4.67 (m, 1H), 4.49 (d, J=5.9 Hz, 2H), 3.67 (m, 2H), 3.18 (m, 2H), 1.92 (m, 2H), 1.52 (m, 2H), 1.41 (s, 9H); (ESI(+)) m/e 451 (M+H)+.
- The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-aminophenoxy)piperidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.47 (m, 2H), 7.88 (d, J=1.1 Hz, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 7.30 (m, 2H), 6.85 (m, 3H), 6.62 (t, J=6.0 Hz, 1H), 4.42 (m, 1H), 4.32 (d, J=6.0 Hz, 2H), 3.64 (m, 2H), 3.15 (m, 2H), 1.86 (m, 2H), 1.51 (m, 2H), 1.40 (s, 9H); (ESI(+)) m/e 466 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}pyrrolidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yl)benzamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.07 (m, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.88 (m, 3H), 7.51 (d, J=1.2 Hz, 1H), 7.42 (m, 3H), 6.85 (dd, J=7.0, 1.6 Hz, 1H), 4.50 (d, J=5.9 Hz, 2H), 3.90-3.66 (m, 1H), 3.63-3.20 (m, 4H), 2.70 (m, 1H), 2.38-2.18 (m, 1H), 2.10-1.90 (m, 1H), 1.01 (m, 6H); (ESI(+)) m/e 391 (M+H)+.
-
TABLE 18 The following Examples were prepared essentially as described in Example 367, substituting the appropriate carboxylic acid in Example 367B. Ex Name 1H NMR MS 368 N-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 9.07 (ESI(+)) a]pyridin-7- (m, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.87 (m, m/e 405 ylmethyl)-4-{1- 3H), 7.52 (d, J = 1.2 Hz, 1H), 7.41 (m, 3H), (M + H)+ [(2S)-2- 6.85 (dd, J = 7.0, 1.6 Hz, 1H), 4.50 (d, J = 5.9 methylbutanoyl]pyrrolidin- Hz, 2H), 3.90-3.66 (m, 1H), 3.63-3.20 (m, 3-yl}benzamide 4H), 2.51 (m, 1H), 2.38-2.18 (m, 1H), 2.10- 1.90 (m, 1H), 1.57 (m, 1H), 1.34 (m, 1H), 1.01 (m, 3H), 0.86 (m, 3H) 369 4-[1- 1H NMR (500 MHz, DMSO-d6) δ ppm 9.07 (ESI(+)) (cyclopropylacetyl) (m, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (m, m/e 403 pyrrolidin-3-yl]-N- 3H), 7.52 (d, J = 1.2 Hz, 1H), 7.42 (m, 3H), (M + H)+ (imidazo[1,2- 6.85 (dd, J = 7.0, 1.6 Hz, 1H), 4.50 (d, J = 5.9 a]pyridin-7- Hz, 2H), 3.88 (m, 1H), 3.61 (m, 1H), 3.60- ylmethyl)benzamide 3.20 (m, 3H), 2.35-2.15 (m, 3H), 2.10-1.88 (m, 1H), 1.99 (m, 1H), 0.44 (m, 2H), 0.12 (m, 2H) 370 4-(1- 1H NMR (500 MHz, DMSO-d6) δ ppm 9.07 (ESI(+)) benzoylpyrrolidin- (m, 1H), 8.48 (t, J = 6.2 Hz, 1H), 7.88 (m, m/e 425 3-yl)-N- 3H), 7.55 (m, 2H), 7.54-7.34 (m, 7H), 6.85 (M + H)+ (imidazo[1,2- (m, 1H), 4.50 (m, 2H), 4.00 (m, 1H), 3.73 (m, a]pyridin-7- 1H), 3.65-3.40 (m, 3H), 2.38-2.22 (m, 1H), ylmethyl)benzamide 2.15-1.94 (m, 1H) 371 N-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 9.07 (ESI(+)) a]pyridin-7- (m, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.89 (m, m/e 421 ylmethyl)-4-{1- 3H), 7.52 (d, J = 1.2 Hz, 1H), 7.41 (m, 3H), (M + H)+ [(propan-2- 6.85 (dd, J = 7.0, 1.6 Hz, 1H), 4.51 (d, J = 5.9 yloxy)acetyl]pyrrolidin- Hz, 2H), 4.05 (d, J = 4.5 Hz, 2H), 3.95-3.81 3-yl}benzamide (m, 1H), 3.70-3.55 (m, 2H), 3.55-3.20 (m, 3H), 2.38-2.18 (m, 1H), 2.08-1.88 (m, 1H), 1.11 (m, 6H) 372 4-[1-(2-hydroxy-2- 1H NMR (500 MHz, DMSO-d6) δ ppm 9.07 (ESI(+)) methylpropanoyl)pyrrolidin- (t, J = 6.0 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H), m/e 407 3-yl]-N- 7.88 (m, 3H), 7.52 (d, J = 1.2 Hz, 1H), 7.42 (M + H)+ (imidazo[1,2- (m, 2H), 7.38 (m, 1H), 6.85 (dd, J = 7.0, 1.6 a]pyridin-7- Hz, 1H), 5.15 (m, 1H), 4.50 (d, J = 5.9 Hz, ylmethyl)benzamide 2H), 4.34 (m, 1H), 3.85-3.65 (m, 1H), 3.59 (m, 3H), 2.35-2.10 (m, 1H), 2.05-1.86 (m, 1H), 1.30 (m, 6H);) 373 N-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 9.07 (ESI(+)) a]pyridin-7- (m, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (m, m/e 419 ylmethyl)-4-{1- 3H), 7.52 (s, 1H), 7.45-7.35 (m, 3H), 6.85 (M + H)+ [(2R)- (d, J = 7.1 Hz, 1H), 4.55 (m, 1H), 4.50 (m, tetrahydrofuran-2- 2H), 4.10-3.93 (m, 1H), 3.90-3.65 (m, 3H), ylcarbonyl]pyrrolidin- 3.65-3.20 (m, 3H) 2.37-2.19 (m, 1H), 2.10- 3-yl}benzamide 1.76 (m, 5H) 374 N-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 9.08 (ESI(+)) a]pyridin-7- (m, 1H), 8.48 (m, 1H), 7.88 (m, 3H), 7.52 (s, m/e 419 ylmethyl)-4-{1- 1H), 7.45-7.37 (m, 3H), 6.85 (dd, J = 7.0, (M + H)+ [(2S)- 1.6 Hz, 1H), 4.55 (m, 1H), 4.50 (m, 2H), 4.10- tetrahydrofuran-2- 3.93 (m, 1H), 3.90-3.65 (m, 3H), 3.65- ylcarbonyl]pyrrolidin- 3.20 (m, 3H) 2.37-2.19 (m, 1H), 2.10-1.75 3-yl}benzamide (m, 5H) 375 N-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 9.08 (ESI(+)) a]pyridin-7- (m, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.89 (m, m/e 419 ylmethyl)-4-{1- 3H), 7.52 (s, 1H), 7.46 (m, 1H), 7.41 (m, 1H), (M + H)+ [(3S)- 7.38 (m, 1H), 6.85 (d, J = 7.1 Hz, 1H), 4.51 tetrahydrofuran-3- (m, 2H), 4.10-3.93 (m, 1H), 3.95-3.80 (m, ylcarbonyl]pyrrolidin- 2H), 3.65-3.20 (m, 6H), 2.36-2.20 (m, 1H), 3-yl}benzamide 2.14-1.85 (m, 4H) 376 N-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 9.07 (ESI(+)) a]pyridin-7- (m, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (m, m/e 433 ylmethyl)-4-[1- 3H), 7.51 (s, 1H), 7.45 (d, J = 8.0 Hz, 1H), (M + H)+ (tetrahydro-2H- 7.41 (m, 2H), 6.85 (m, 1H), 4.51 (d, J = 3.0 pyran-4- Hz, 2H), 3.88 (m, 3H), 3.75 (m, .55 (m, 2H), ylcarbonyl)pyrrolidin- 3.55-3.20 (m, 3H), 2.71 (m, 1H), 2.39-2.19 3-yl]benzamide (m, 1H), 2.10-1.85 (m, 1H), 1.59 (m, 4H) 377 4-[1-(1,4-dioxan-2- 1H NMR (500 MHz, DMSO-d6) δ ppm 9.07 (ESI(+)) ylcarbonyl)pyrrolidin- (m, 1H), 8.48 (d, J = 7.1 Hz, 1H), 7.89 (m, m/e 435 3-yl]-N- 3H), 7.52 (s, 1H), 7.43 (m, 2H), 7.38 (s, 1H), (M + H)+ (imidazo[1,2- 6.85 (d, J = 7.1 Hz, 1H), 4.51 (dd, J = 5.8, 2.9 a]pyridin-7- Hz, 2H), 4.27 (m, 2H), 4.15-4.00 (m, 1H), ylmethyl)benzamide 3.90-3.70 (m, 4H), 3.70-3.20 (m, 5H); 2.39- 2.19 (m, 1H), 2.15-1.88 (m, 1H) 378 N-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 9.07 (ESI(+)) a]pyridin-7- (m, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (m, m/e 447 ylmethyl)-4-[1- 3H), 7.52 (s, 1H), 7.42 (m, 2H), 7.38 (s, 1H), (M + H)+ (tetrahydro-2H- 6.85 (d, J = 7.1 Hz, 1H), 4.51 (m, 2H), 3.95 pyran-4- (m, 1H), 3.83 (m, 3H), 3.63 (m, 1H), 3.47 (m, ylacetyl)pyrrolidin- 2H), 3.45-3.20 (m, 2H), 2.38-2.15 (m, 3H), 3-yl]benzamide 2.10-1.90 (m, 2H), 1.56 (m, 2H), 1.21 (m, 2H) 488 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 431 ylmethyl)-4-[1- (M + H)+ (thiophen-2- ylcarbonyl)pyrrolidin- 3-yl]benzamide 562 4-[1-(4- (ESI(+)) fluorobenzo- m/e 443 yl)pyrrolidin-3-yl]- (M + H)+ N-(imidazo[1,2- a]pyridin-7- ylmethyl)benzamide 580 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 403 ylmethyl)-4-{1-[(2- (M + H)+ methylcyclopropyl) carbonyl]pyrrolidin- 3-yl}benzamide 581 4-[1- (ESI(+)) (cyclopentylacetyl)pyrrolidin- m/e 431 3-yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)benzamide 582 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 419 ylmethyl)-4-[1-(3- (M + H)+ methylpentanoyl)pyrrolidin- 3-yl]benzamide 583 4-[1- (ESI(+)) (cyclopentylcarbon- m/e 417 yl)pyrrolidin- (M + H)+ 3-yl]-N-(imidazo[1,2- a]pyridin-7- ylmethyl)benzamide 584 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 403 ylmethyl)-4-{1-[(1- (M + H)+ methylcyclopropyl) carbonyl]pyrrolidin- 3-yl}benzamide 585 4-[1-(2,2- (ESI(+)) dimethylpropanoyl) m/e 405 pyrrolidin-3-yl]-N- (M + H)+ (imidazo[1,2- a]pyridin-7- ylmethyl)benzamide 586 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 432 ylmethyl)-4-[1-(1,3- (M + H)+ thiazol-5- ylcarbonyl)pyrrolidin- 3-yl]benzamide 587 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 455 ylmethyl)-4-[1-(2- (M + H)+ methoxybenzoyl)pyrrolidin- 3-yl]benzamide 588 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 432 ylmethyl)-4-[1-(1,3- (M + H)+ thiazol-4- ylcarbonyl)pyrrolidin- 3-yl]benzamide 589 4-[1-(2- (ESI(+)) fluorobenzoyl)pyrrolidin- m/e 443 3-yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)benzamide 590 4-[1-(furan-2- (ESI(+)) ylcarbonyl)pyrrolidin- m/e 415 3-yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)benzamide 591 4-[1-(3- (ESI(+)) fluorobenzoyl)pyrrolidin- m/e 443 3-yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)benzamide 592 4-[1-(2,4- (ESI(+)) difluorobenzoyl)pyrrolidin- m/e 461 3-yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)benzamide 593 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 429 ylmethyl)-4-{1-[(1- (M + H)+ methyl-1H-pyrazol-3- yl)carbonyl]pyrrolidin- 3-yl}benzamide 594 4-[1-(2- (ESI(+)) chlorobenzoyl)pyrrolidin- m/e 459 3-yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)benzamide 595 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 439 ylmethyl)-4-[1-(2- (M + H)+ methylbenzoyl)pyrrolidin- 3-yl]benzamide 596 4-[1-(4- (ESI(+)) chlorobenzoyl)pyrrolidin- m/e 459 3-yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)benzamide 597 4-[1-(3- (ESI(+)) chlorobenzoyl)pyrrolidin- m/e 459 3-yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)benzamide 598 4-[1-(2,2- (ESI(+)) dimethylbutanoyl)pyrrolidin- m/e 419 3-yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)benzamide 599 4-[1-(3,5- (ESI(+)) difluorobenzoyl)pyrrolidin- m/e 461 3-yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)benzamide 600 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 439 ylmethyl)-4-[1-(4- (M + H)+ methylbenzoyl)pyrrolidin- 3-yl]benzamide 601 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 405 ylmethyl)-4-[1-(3- (M + H)+ methylbutanoyl)pyrrolidin- 3-yl]benzamide 602 4-[1-(3,3- (ESI(+)) dimethylbutanoyl)pyrrolidin- m/e 419 3-yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)benzamide 603 4-[1-(3- (ESI(+)) cyanobenzoyl)pyrrolidin- m/e 450 3-yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)benzamide 604 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 455 ylmethyl)-4-[1-(3- (M + H)+ methoxybenzoyl)pyrrolidin- 3-yl]benzamide 605 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 455 ylmethyl)-4-[1-(4- (M + H)+ methoxybenzoyl)pyrrolidin- 3-yl]benzamide 606 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 428 ylmethyl)-4-{1-[(1- (M + H)+ methyl-1H-pyrrol-2- yl)carbonyl]pyrrolidin- 3-yl}benzamide 607 4-[1- (ESI(+)) (cyclohexylacetyl)pyrrolidin- m/e 445 3-yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)benzamide 608 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 426 ylmethyl)-4-[1- (M + H)+ (pyridin-4- ylcarbonyl)pyrrolidin- 3-yl]benzamide 609 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 426 ylmethyl)-4-[1- (M + H)+ (pyridin-3- ylcarbonyl)pyrrolidin- 3-yl]benzamide 610 4-[1- (ESI(+)) (cyclohexylcarbon- m/e 431 yl)pyrrolidin-3-yl]-N- (M + H)+ (imidazo[1,2- a]pyridin-7- ylmethyl)benzamide 611 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 426 ylmethyl)-4-[1- (M + H)+ (pyridin-2- ylcarbonyl)pyrrolidin- 3-yl]benzamide 612 4-[1-(furan-3- (ESI(+)) ylcarbonyl)pyrrolidin- m/e 415 3-yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)benzamide 613 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 432 ylmethyl)-4-[1-(1,3- (M + H)+ thiazol-2- ylcarbonyl)pyrrolidin- 3-yl]benzamide 614 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 445 ylmethyl)-4-{1-[(1- (M + H)+ methylcyclohexyl)car- bonyl]pyrrolidin- 3-yl}benzamide 615 4-[1-(2,3- (ESI(+)) dimethylbutanoyl)pyrrolidin- m/e 419 3-yl]-N-(imidazo[1,2- (M + H)+ a]pyridin-7- ylmethyl)benzamide 616 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 439 ylmethyl)-4-[1-(3- (M + H)+ methylbenzoyl)pyrrolidin- 3-yl]benzamide 617 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 431 ylmethyl)-4-[1- (M + H)+ (thiophen-3- ylcarbonyl)pyrrolidin- 3-yl]benzamide 618 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 509 ylmethyl)-4-{1-[3- (M + H)+ (trifluorome- thoxy)benzoyl]pyrrolidin- 3-yl}benzamide 619 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 445 ylmethyl)-4-{1-[(3- (M + H)+ methylthiophen-2- yl)carbonyl]pyrrolidin- 3-yl}benzamide 620 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 493 ylmethyl)-4-{1-[3- (M + H)+ (trifluorometh- yl)benzoyl]pyrrolidin- 3-yl}benzamide 731 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 439 ylmethyl)-4-[1- (M + H)+ (phenylacetyl)pyrrolidin- 3-yl]benzamide 732 N-(imidazo[1,2- (ESI(+)) a]pyridin-7- m/e 467 ylmethyl)-4-[1-(2- (M + H)+ methyl-2- phenylpropanoyl)pyrrolidin- 3-yl]benzamide 733 4-{1- (ESI(+)) [difluoro(phenyl)ace- m/e 475 tyl]pyrrolidin-3-yl}- (M + H)+ N-(imidazo[1,2- a]pyridin-7- ylmethyl)benzamide - The title compound was prepared as described in Example 28A, substituting tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)pyrrolidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-(pyrrolidin-3-yl)phenyl)urea for 3-methylbutan-1-amine and acetic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.62 (d, J=6.4 Hz, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.88 (s, 1H), 7.51 (s, 1H), 7.37 (m, 3H), 7.16 (m, 2H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.69 (m, 1H), 4.33 (d, J=6.0 Hz, 2H), 3.89-3.73 (m, 1H), 3.65-3.45 (m, 3H), 3.10 (m, 1H), 2.29-2.11 (m, 1H), 2.00-1.80 (m, 1H), 1.91 (s, 3H); (ESI(+)) m/e 378 (M+H)+.
- The following Examples were prepared essentially as described in Example 379, substituting the appropriate carboxylic acid in Example 379B.
-
Ex Name 1H NMR MS 380 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.62 (d, (ESI(+)) a]pyridin-7- J = 6.5 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 m/e 406 ylmethyl)-3-{4- (s, 1H), 7.51 (s, 1H), 7.36 (m, 3H), 7.16 (m, (M + H)+ [1-(2- 2H), 6.83 (d, J = 7.1 Hz, 1H), 6.70 (m, 1H), methylpropanoyl) 4.33 (d, J = 6.0 Hz, 2H), 3.80-3.65 (m, 1H), pyrrolidin-3- 3.60-3.48 (m, 1H), 3.45-3.20 (m, 2H), 3.13 yl]phenyl}urea (m, 1H), 2.68 (m, 1H), 2.30-2.10 (m, 1H), 2.05-1.80 (m, 1H), 1.00 (m, 6H) 381 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.62 (d, (ESI(+)) a]pyridin-7- J = 6.5 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 m/e 420 ylmethyl)-3-(4- (s, 1H), 7.52 (s, 1H), 7.37 (m, 3H), 7.17 (m, (M + H)+ {1-[(2S)-2- 2H), 6.83 (dd, J = 7.0, 1.6 Hz, 1H), 6.69 (t, J = methylbutanoyl]pyrro- 6.0 Hz, 1H), 4.33 (d, J = 6.0 Hz, 2H), 3.95- lidin-3- 3.75 (m, 1H), 3.70-3.45 (m, 2H), 3.45-3.20 yl}phenyl)urea (m, 1H), 3.20 (m, 1H), 2.30-2.11 (m, 1H), 2.05-1.80 (m, 1H), 1.55 (m, 1H), 1.25 (m, 2H), 0.96 (m, 3H), 0.87 (m, 3H) 382 1-{4-[1- - 1H NMR (500 MHz, DMSO-d6) δ ppm 8.62 (ESI(+)) (cyclopropyl- (d, J = 4.1 Hz, 1H), 8.49 (d, J = 7.0 Hz, 1H), m/e 418 acetyl)pyrrolidin-3- 7.89 (s, 1H), 7.52 (s, 1H), 7.37 (m, 3H), 7.16 (M + H)+ yl]phenyl}-3- (m, 2H), 6.84 (d, J = 7.1 Hz, 1H), 6.69 (t, J = (imidazo[1,2- 6.0 Hz, 1H), 4.33 (d, J = 6.0 Hz, 2H), 3.80 (m, a]pyridin-7- 1H), 3.58 (m, 1H), 3.45 (m, 1H), 3.40-3.20 ylmethyl)urea (m, 1H), 3.12 (m, 1H), 2.27-2.11 (m, 3H), 1.99-1.81 (m, 1H), 0.98 (m, 1H), 0.44 (m, 2H), 0.11 (m, 2H) 383 1-[4-(1- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.62 (m, (ESI(+)) benzoylpyrrolidin- 1H), 8.48 (d, J = 6.1 Hz, 1H), 7.88 (d, J = 3.0 m/e 440 3-yl)phenyl]-3- Hz, 1H), 7.53 (m, 3H), 7.50-7.35 (m, 5H), (M + H)+ (imidazo[1,2- 7.34 (d, 1H), 7.20 (d, J = 8.2 Hz, 1H), 7.13 (d, J = a]pyridin-7- 8.2 Hz, 1H), 6.83 (m, 1H), 6.68 (m, 1H), 4.33 ylmethyl)urea (d, J = 14.1 Hz, 2H), 3.68 (m, 1H), 3.60-3.45 (m, 2H), 3.40-3.20 (m, 2H), 2.29-2.13 (m, 1H) 2.07-1.90 (m, 1H) 384 1-(imidazo[1,2- - 1H NMR (500 MHz, DMSO-d6) δ ppm 8.63 (ESI(+)) a]pyridin-7- (d, J = 6.0 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H), m/e 436 ylmethyl)-3-(4- 7.88 (s, 1H), 7.51 (s, 1H), 7.37 (m, 3H), 7.16 (M + H)+ {1-[(propan-2- (m, 2H), 6.83 (dd, J = 7.0, 1.6 Hz, 1H), 6.70 (m, yloxy)acetyl]pyrro- 1H), 4.33 (d, J = 6.0 Hz, 2H), 4.03 (d, J = 5.4 lidin-3- Hz, 2H), 3.90-3.74 (m, 1H), 3.68-3.52 (m, yl}phenyl)urea 2H), 3.47 (m, 1H), 3.40-3.20 (m, 1H), 3.16 (m, 1H), 2.29-2.11 (m, 1H), 2.00-1.73 (m, 1H), 1.10 (m, 6H) 385 1-{4-[1-(2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.65 (d, (ESI(+)) hydroxy-2- J = 6.0 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 m/e 422 methylpropanoyl) (s, 1H), 7.51 (s, 1H), 7.37 (m, 3H), 7.16 (m, (M + H)+ pyrrolidin-3- 2H), 6.83 (dd, J = 7.0, 1.6 Hz, 1H), 6.73 (m, yl]phenyl}-3- 1H), 5.18 (bs, 1H), 4.33 (d, J = 6.0 Hz, 2H), (imidazo[1,2- 4.28 (m, 1H), 3.80-3.60 (m, 1H), 3.60-3.10 a]pyridin-7- (m, 3H), 2.25-2.08 (m, 1H), 1.97-1.73 (m, ylmethyl)urea 1H), 1.30 (m, 6H) 386 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.62 (d, (ESI(+)) a]pyridin-7- J = 5.7 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 m/e 434 ylmethyl)-3-(4- (s, 1H), 7.51 (s, 1H), 7.37 (m, 3H), 7.16 (m, (M + H)+ {1-[(2R)- 2H), 6.83 (d, J = 6.2 Hz, 1H), 6.69 (t, J = 6.0 tetrahydrofuran-2- Hz, 1H), 4.53 (m, 1H), 4.33 (d, J = 6.0 Hz, 2H), ylcarbonyl]pyrro- 3.85-3.64 (m, 3H), 3.63-3.45 (m, 1H), 3.45- lidin-3- 3.20 (m, 2H), 3.16 (m, 1H), 2.29-2.10 (m, yl}phenyl)urea 1H), 2.08-1.92 (m, 2H), 1.91-1.73 (m, 3H) 387 1-(imidazo[1,2- - 1H NMR (500 MHz, DMSO-d6) δ ppm 8.62 (ESI(+)) a]pyridin-7- (d, J = 5.6 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H), m/e 434 ylmethyl)-3-(4- 7.88 (s, 1H), 7.51 (s, 1H), 7.36 (m, 3H), 7.16 (M + H)+ {1-[(2S)- (m, 2H), 6.83 (dd, J = 7.0, 1.6 Hz, 1H), 6.69 (t, tetrahydrofuran-2- J = 6.0 Hz, 1H), 4.53 (m, 1H), 4.33 (d, J = 6.0 ylcarbonyl]pyrro- Hz, 2H), 3.84-3.64 (m, 3H), 3.63-3.45 (m, lidin-3- 1H), 3.45-3.20 (m, 2H), 3.16 (m, 1H), 2.29- yl}phenyl)urea 2.10 (m, 1H), 2.05-1.85 (m, 5H) 388 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.63 (d, (ESI(+)) a]pyridin-7- J = 6.7 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 m/e 434 ylmethyl)-3-(4- (s, 1H), 7.52 (s, 1H), 7.37 (m, 3H), 7.17 (m, (M + H)+ {1-[(3S)- 2H), 6.83 (dd, J = 7.0, 1.6 Hz, 1H), 6.70 (m, tetrahydrofuran-3- 1H), 4.33 (d, J = 6.0 Hz, 2H), 3.97-3.84 (m, ylcarbonyl]pyrro- 2H), 3.80-3.63 (m, 4H), 3.62-3.46 (m, 1H), lidin-3- 3.45-3.10 (m, 3H), 2.29-2.10 (m, 1H), 2.09- yl}phenyl)urea 1.83 (m, 3H) 389 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.62 (d, (ESI(+)) a]pyridin-7- J = 7.5 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 m/e 448 ylmethyl)-3-{4- (s, 1H), 7.51 (s, 1H), 7.36 (m, 3H), 7.16 (m, (M + H)+ [1-(tetrahydro- 2H), 6.83 (d, J = 7.1 Hz, 1H), 6.69 (t, J = 6.0 2H-pyran-4- Hz, 1H), 4.33 (d, J = 6.0 Hz, 2H), 3.90-3.70 ylcarbonyl)pyrro- (m, 3H), 3.55 (m, 1H), 3.45-3.20 (m, 3H), lidin-3- 3.15 (m, 1H), 2.70 (m, 1H), 2.28-2.11 (m, yl]phenyl}urea 1H), 2.00-1.82 (m, 1H), 1.57 (m, 4H) 390 1-{4-[1-(1,4- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.62 (d, (ESI(+)) dioxan-2- J = 7.5 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 m/e 450 ylcarbonyl)pyrro- (s, 1H), 7.51 (s, 1H), 7.37 (m, 3H), 7.16 (m, (M + H)+ lidin-3-yl]phenyl}- 2H), 6.83 (d, J = 7.1 Hz, 1H), 6.70 (t, J = 6.0 3-(imidazo[1,2- Hz, 1H), 4.33 (d, J = 6.0 Hz, 2H), 4.25 (m, 1H), a]pyridin-7- 3.85-3.70 (m, 3H), 3.70-3.60 (m, 2H), 3.60- ylmethyl)urea 3.45 (m, 3H), 3.45-3.15 (m, 3H), 2.28-2.11 (m, 1H), 2.00-1.80 (m, 1H) 391 1-(imidazo[1,2- - 1H NMR (400 MHz, DMSO-d6) δ ppm 8.62 (ESI(+)) a]pyridin-7- (d, J = 5.5 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H), m/e 462 ylmethyl)-3-{4- 7.88 (s, 1H), 7.51 (s, 1H), 7.36 (m, 3H), 7.16 (M + H)+ [1-(tetrahydro- (m, 2H), 6.83 (dd, J = 7.0, 1.6 Hz, 1H), 6.69 (t, 2H-pyran-4- J = 6.0 Hz, 1H), 4.33 (d, J = 5.9 Hz, 2H), 3.90- ylacetyl)pyrro- 3.72 (m, 3H), 3.67-3.40 (m, 2H), 3.27-3.08 lidin-3- (m, 2H), 3.14 (m, 1H), 2.28-2.10 (m, 3H), yl]phenyl}urea 2.00-1.80 (m, 3H), 1.59 (m, 2H), 1.17 (m, 2H) 392 1-(imidazo[1,2- - 1H NMR (400 MHz, DMSO-d6) δ ppm 8.65 (ESI(+)) a]pyridin-7- (d, J = 6.1 Hz, 1H), 8.48 (d, J = 6.9 Hz, 1H), m/e 463 ylmethyl)-3-{4- 7.88 (s, 1H), 7.51 (d, J = 1.2 Hz, 1H), 736 (m, (M + H)+ [1-(morpholin-4- 3H), 7.16 (m, 2H), 6.83 (dd, J = 6.9, 1.7 Hz, ylacetyl)pyrro- 1H), 6.72 (td, J = 6.0, 2.3 Hz, 1H), 4.33 (d, J = lidin-3- 5.9 Hz, 2H), 3.74 (m, 1H), 3.55 (m, 4H), 3.45- yl]phenyl}urea 3.20 (m, 2H), 3.17 (s, 2H), 3.13-3.03 (m, 2H), 2.44 (m, 4H), 2.30-2.10 (m, 1H), 2.00-1.80 (m, 1H) - The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(methoxycarbonyl)benzoic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 4B, substituting methyl 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
- The title compound was prepared as described in Example 1A, substituting 3-methylbutan-1-amine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.25-9.11 (m, 1H), 8.57-8.37 (m, 2H), 8.04-7.81 (m, 5H), 7.51 (t, J=2.6 Hz, 1H), 7.41 (t, J=2.9 Hz, 1H), 6.87 (dd, J=7.0, 1.7 Hz, 1H), 4.58-4.38 (m, 2H), 3.29-3.25 (m, 2H), 1.71-1.56 (m, 1H), 1.53-1.31 (m, 2H), 0.91 (d, J=6.5 Hz, 6H); MS (ESI(+)) m/e 365 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting (S)-(tetrahydrofuran-3-yl)methanamine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.21 (t, J=5.9 Hz, 1H), 8.69 (t, J=5.7 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.07-7.71 (m, 5H), 7.52 (d, J=1.2 Hz, 1H), 7.41 (s, 1H), 6.87 (dd, J=7.0, 1.7 Hz, 1H), 4.52 (d, J=5.9 Hz, 2H), 3.80-3.56 (m, 4H), 3.48 (dd, J=8.5, 5.2 Hz, 1H), 2.02-1.87 (m, 1H), 1.68-1.53 (m, 1H), 1.32-1.00 (m, 2H); MS (ESI(+)) m/e 379 (M+H)+.
- A solution of 4-(3-imidazo[1,2-a]pyridin-6-ylureido)-N-((tetrahydro-2H-pyran-2-yl)methyl)benzamide (0.016 g, 0.041 mmol) in chloroform (0.813 ml) was treated with N-chlorosuccinimide (5.70 mg, 0.043 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under a stream of nitrogen and purified using normal phase chromatography to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.11 (s, 1H), 9.02 (s, 1H), 8.89-8.85 (m, 1H), 8.35 (t, J=5.8 Hz, 1H), 7.85-7.79 (m, 2H), 7.69-7.60 (m, 2H), 7.58-7.52 (m, 2H), 7.19 (dd, J=9.5, 2.0 Hz, 1H), 3.91-3.83 (m, 1H), 3.46-3.19 (m, 4H), 1.80-1.73 (m, 1H), 1.66-1.57 (m, 1H), 1.49-1.36 (m, 3H), 1.26-1.09 (m, 1H); MS (ESI(+)) m/e 428 (M+H)+.
- The title compound was prepared as described in Example 396, substituting N-[(3-imidazo[1,2-a]pyridin-6-yl)methyl]-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide for 4-(3-imidazo[1,2-a]pyridin-6-ylureido)-N-((tetrahydro-2H-pyran-2-yl)methyl)benzamide. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.15 (s, 1H), 8.95 (t, J=5.8 Hz, 1H), 8.30-8.25 (m, 1H), 7.87-7.80 (m, 2H), 7.71-7.59 (m, 4H), 7.35 (dd, J=9.3, 1.7 Hz, 1H), 4.54 (d, J=5.8 Hz, 2H), 3.86-3.58 (m, 3H), 3.38-3.30 (m, 1H), 2.62-2.52 (m, 1H), 2.47-2.39 (m, 2H), 2.10-1.95 (m, 1H), 1.62-1.46 (m, 1H); MS (ESI(+)) m/e 413 (M+H)+.
- The title compound was prepared as described in Example 324A, substituting dihydro-2H-pyran-4(3H)-one for N-(oxetan-3-ylidene)propane-2-sulfinamide.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(4-hydroxytetrahydro-2H-pyran-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.99 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.1 Hz, 1H), 7.88 (s, 1H), 7.66 (d, J=3.7 Hz, 1H), 7.52 (s, 1H), 7.37 (s, 1H), 7.02 (d, J=3.7 Hz, 1H), 6.83 (dd, J=7.0, 1.5 Hz, 1H), 5.67 (s, 1H), 4.46 (d, J=6.1 Hz, 2H), 3.63-3.77 (m, 4H), 1.89-2.04 (m, 2H), 1.69 (d, J=11.9 Hz, 2H); MS (ESI(+)) m/e 358 (M+H)+.
- The title compound was prepared as described in Example 324A, substituting tert-butyl 3-oxoazetidine-1-carboxylate for N-(oxetan-3-ylidene)propane-2-sulfinamide.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(1-(tert-butoxycarbonyl)-3-hydroxyazetidin-3-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 3-hydroxy-3-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)azetidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 5-(3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.06 (t, J=6.0 Hz, 1H), 8.49 (d, J=7.1 Hz, 1H), 7.89 (s, 1H), 7.72 (d, J=3.6 Hz, 1H), 7.52 (s, 1H), 7.38 (s, 1H), 7.18 (d, J=3.6 Hz, 1H), 6.90 (s, 1H), 6.83 (dd, J=6.9, 1.4 Hz, 1H), 4.47 (d, J=6.0 Hz, 2H), 4.41 (d, J=9.1 Hz, 1H), 4.32 (d, J=9.1 Hz, 1H), 4.05 (dd, J=17.5, 9.9 Hz, 2H), 2.46-2.57 (m, 1H), 1.00 (d, J=7.1 Hz, 6H); MS (ESI(+)) m/e 399 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 5-(3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.05 (t, J=5.8 Hz, 1H), 8.48 (d, J=6.1 Hz, 1H), 7.88 (s, 1H), 7.73 (d, J=3.7 Hz, 1H), 7.66-7.71 (m, 2H), 7.43-7.54 (m, 4H), 7.38 (d, J=1.0 Hz, 1H), 7.26 (d, J=3.7 Hz, 1H), 6.93 (s, 1H), 6.83 (dd, J=7.1, 1.7 Hz, 1H), 4.46 (d, J=6.1 Hz, 2H), 4.23-4.63 (br. m, 4H); MS (ESI(+)) m/e 433 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)azetidin-3-yl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.09 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.91 (m, 3H), 7.52 (d, J=1.2 Hz, 1H), 7.45 (m, 2H), 7.38 (s, 1H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 4.26 (m, 2H), 3.87 (m, 3H), 1.41 (s, 9H); (ESI(+)) m/e 407 (M+H)+.
- The title compound was prepared as described in Example 324A, substituting tert-butyl 3-oxopiperidine-1-carboxylate for N-(oxetan-3-ylidene)propane-2-sulfinamide.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(1-(tert-butoxycarbonyl)-4-hydroxypiperidin-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.98 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.1 Hz, 1H), 7.88 (s, 1H), 7.65 (d, J=4.1 Hz, 1H), 7.51 (d, J=1.0 Hz, 1H), 7.37 (s, 1H), 7.01 (d, J=3.7 Hz, 1H), 6.83 (dd, J=7.0, 1.5 Hz, 1H), 5.72 (s, 1H), 4.46 (d, J=5.8 Hz, 2H), 3.75-3.86 (m, 2H), 1.71-1.86 (m, 2H), 1.41 (s, 9H), 1.21-1.30 (m, 2H), 0.94 (d, J=5.8 Hz, 2H); MS (ESI(+)) m/e 457 (M+H)+.
- The title compound was prepared as described in Example 1C, substituting ethyl 2-aminothiazole-5-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine.
- The title compound was prepared as described in Example 4B, substituting ethyl 2-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)thiazole-5-carboxylate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
- The title compound was prepared as described in Example 1A, substituting piperidine for 3-methylbutan-1-amine and 2-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)thiazole-5-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.91 (s, 1H), 8.49 (d, J=7.1 Hz, 1H), 7.89 (s, 1H), 7.62 (s, 1H), 7.52 (d, J=0.8 Hz, 1H), 7.39 (s, 1H), 7.11-7.18 (m, 1H), 6.83 (dd, J=6.9, 1.4 Hz, 1H), 4.39 (d, J=6.0 Hz, 2H), 3.54-3.61 (m, 4H), 1.47-1.67 (m, 6H); MS (ESI(+)) m/e 385 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 5-(3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (S)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) ppm 9.06 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.1 Hz, 1H), 7.88 (s, 1H), 7.72 (d, J=4.1 Hz, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.38 (s, 1H), 7.16 (dd, J=7.0, 3.9 Hz, 1H), 6.89 (s, 1H), 6.83 (dd, J=7.0, 1.5 Hz, 1H), 4.46 (d, J=6.1 Hz, 2H), 4.35-4.42 (m, 1H), 4.32 (d, J=8.8 Hz, 1H), 4.09 (dd, J=10.5, 4.4 Hz, 1H), 4.03 (d, J=10.2 Hz, 1H), 2.25-2.38 (m, 1H), 1.49 (s, 1H), 1.23-1.38 (m, 1H), 0.99 (d, J=6.8 Hz, 3H), 0.80-0.88 (m, 3H); MS (ESI(+)) m/e 413 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 5-(3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 2-(tetrahydro-2H-pyran-4-yl)acetic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.07 (t, J=6.0 Hz, 1H), 8.49 (d, J=7.0 Hz, 1H), 7.89 (s, 1H), 7.72 (d, J=4.0 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.38 (s, 1H), 7.18 (d, J=4.0 Hz, 1H), 6.89 (s, 1H), 6.83 (dd, J=7.0, 1.5 Hz, 1H), 4.47 (d, J=5.8 Hz, 2H), 4.37 (d, J=9.2 Hz, 1H), 4.26-4.40 (m, 2H), 4.05-4.11 (m, 1H), 4.00-4.10 (m, 2H), 3.78-3.84 (m, 2H), 2.04-2.07 (m, 2H), 1.85-1.97 (m, 1H), 1.53-1.62 (m, 2H), 1.15-1.28 (m, 2H); MS (ESI(+)) m/e 455 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 3-methylbutan-1-amine for 3-methylbutan-1-amine and 2-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)thiazole-5-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.49 (d, J=7.8 Hz, 1H), 8.21 (t, J=5.9 Hz, 1H), 7.88-7.89 (m, J=1.4 Hz, 1H), 7.87 (s, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.39 (s, 1H), 7.18 (t, J=5.8 Hz, 1H), 6.83 (dd, J=6.8, 1.7 Hz, 1H), 4.38 (d, J=6.1 Hz, 2H), 3.16-3.25 (m, 2H), 1.52-1.67 (m, 1H), 1.38 (q, J=6.9 Hz, 2H), 0.83-0.91 (m, 7H); MS (ESI(+)) m/e 387 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 5-(3-aminooxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (S)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.11 (s, 1H), 9.05 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.8 Hz, 1H), 7.88 (s, 1H), 7.71 (d, J=3.7 Hz, 1H), 7.52 (s, 1H), 7.38 (s, 1H), 7.22 (d, J=3.7 Hz, 1H), 6.83 (dd, J=7.1, 1.7 Hz, 1H), 4.77-4.83 (m, 2H), 4.72 (dd, J=6.4, 4.4 Hz, 2H), 4.46 (d, J=5.8 Hz, 2H), 2.19-2.29 (m, 1H), 1.46-1.66 (m, 1H), 1.26-1.43 (m, 1H), 1.03 (d, J=6.8 Hz, 3H), 0.85 (t, J=7.3 Hz, 3H); MS (ESI(+)) m/e 413 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting 3-methylbutanoyl chloride for 2-cyclopentylacetyl chloride and piperidin-4-ol for methyl 4-aminobenzoate.
- A solution of 1-(hydroxypiperidin-1-yl)-3-methylbutan-1-one (793 mg, 4.28 mmol), ethyl 1H-pyrazole-4-carboxylate (500 mg, 3.57 mmol) and cyanomethylenetributylphosphorane (1.03 g, 4.28 mmol) in toluene (20 ml) was stirred overnight at 85° C. The solvent was removed and the crude mixture was purified by normal phase chromatography to give the title compound.
- The title compound was prepared as described in Example 4B, substituting ethyl 1-(1-(3-methylbutanoyl)piperidin-4-yl)-1H-pyrazole-3-carboxylate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 1-(1-(3-methylbutanoyl)piperidin-4-yl)-1H-pyrazole-3-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.10 (t, J=6.0 Hz, 1H), 8.50 (dd, J=7.0, 0.9 Hz, 1H), 7.93-7.86 (m, 1H), 7.57-7.47 (m, 2H), 7.41 (s, 1H), 6.92 (d, J=2.0 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 5.45-5.28 (m, 1H), 4.57-4.43 (m, 3H), 3.99 (d, J=14.0 Hz, 1H), 3.20-3.03 (m, 1H), 2.70-2.53 (m, 1H), 2.32-2.11 (m, 3H), 2.09-1.68 (m, 4H), 0.91 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 408 (M+H).
- The title compound was prepared as described in Example 1C, substituting tert-butyl 3-(4-aminophenoxy)azetidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 3-(4-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)phenoxy)azetidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 1-(4-(azetidin-3-yloxy)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 3-methylbutan-1-amine and acetic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.50 (m, 2H), 7.88 (s, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (m, 1H), 7.33 (m, 2H), 6.83 (dd, J=6.9, 1.6 Hz, 1H), 6.74 (m, 2H), 6.63 (t, J=6.0 Hz, 1H), 4.93 (m, 1H), 4.51 (m, 1H), 4.32 (d, J=6.0 Hz, 2H), 4.24 (m, 1H), 4.04 (dd, J=9.6, 4.1 Hz, 1H), 3.72 (dd, J=10.5, 4.0 Hz, 1H), 1.78 (s, 3H); (ESI(+)) m/e 380 (M+H)+.
-
TABLE 20 The following Examples were prepared essentially as described in Example 424, substituting the appropriate carboxylic acid in Example 424C. Ex Name 1H NMR MS 425 1-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.49 (m, (ESI(+)) a]pyridin-7- 2H), 7.88 (s, 1H), 7.51 (d, J = 1.2 Hz, 1H), 7.37 m/e 408 ylmethyl)-3-(4- (m, 1H), 7.33 (m, 2H), 6.83 (dd, J = 6.9, 1.7 Hz, (M + H)+ {[1-(2- 1H), 6.75 (m, 2H), 6.63 (t, J = 6.0 Hz, 1H), 4.95 methylpropanoyl)azetidin- (m, 1H), 4.57 (dd, J = 9.4, 6.4 Hz, 1H), 4.32 (d, J = 3- 6.0 Hz, 2H), 4.25 (dd, J = 10.5, 6.5 Hz, 1H), yl]oxy}phenyl)urea 4.08 (dd, J = 9.4, 3.9 Hz, 1H), 3.73 (dd, J = 10.5, 4.0 Hz, 1H), 2.47 (m, 1H), 0.97 (m, 6H) 426 1-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.49 (m, (ESI(+)) a]pyridin-7- 2H), 7.88 (d, J = 1.1 Hz, 1H), 7.51 (d, J = 1.2 Hz, m/e 422 ylmethyl)-3-[4- 1H), 7.37 (m, 1H), 7.33 (m, 2H), 6.83 (dd, J = 6.9, (M + H)+ ({1-[(2S)-2- 1.6 Hz, 1H), 6.75 (m, 2H), 6.64 (t, J = 6.0 Hz, methylbutanoyl]azetidin- 1H), 4.95 (m, 1H), 4.56 (dd, J = 9.4, 6.5 Hz, 1H), 3- 4.32 (d, J = 6.0 Hz, 2H), 4.26 (m, 1H), 4.08 (m, yl}oxy)phenyl]urea 1H), 3.74 (m, 1H), 2.28 (m, 1H), 1.47 (m, 1H), 1.28 (m, 1H), 0.95 (m, 3H), 0.81 (m, 3H) 427 1-(4-{[1- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.49 (m, (ESI(+)) (cyclopro- 2H), 7.90 (s, 1H), 7.54 (d, J = 1.2 Hz, 1H), 7.39 m/e 420 pylacetyl)azetidin-3- (s, 1H), 7.33 (m, 2H), 6.86 (dd, J = 7.0, 1.6 Hz, (M + H)+ yl]oxy}phenyl)- 1H), 6.74 (m, 2H), 6.64 (t, J = 6.0 Hz, 1H), 4.94 3-(imidazo[1,2- (m, 1H), 4.50 (dd, J = 9.6, 6.6 Hz, 1H), 4.33 (d, J = a]pyridin-7- 6.0 Hz, 2H), 4.26 (dd, J = 10.5, 6.5 Hz, 1H), ylmethyl)urea 4.03 (dd, J = 9.4, 3.9 Hz, 1H), 3.74 (dd, J = 10.5, 3.9 Hz, 1H), 2.02 (d, J = 6.8 Hz, 2H), 0.92 (m, 1H), 0.43 (m, 2H), 0.10 (m, 2H) 428 1-{4-[(1- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.49 (m, (ESI(+)) benzoylazetidin- 2H), 7.88 (s, 1H), 7.65 (m, 2H), 7.52 (m, 2H), m/e 442 3- 7.45 (m, 2H), 7.37 (m, 1H), 7.33 (m, 2H), 6.83 (M + H)+ yl)oxy]phenyl}- (dd, J = 6.9, 1.6 Hz, 1H), 6.75 (m, 2H), 6.63 (t, J = 3-(imidazo[1,2- 6.0 Hz, 1H), 5.00 (m, 1H), 4.67 (m, 1H), 4.51 a]pyridin-7- (m, 1H), 4.32 (d, J = 6.0 Hz, 2H), 4.26 (m, 1H), ylmethyl)urea 3.97 (m, 1H) 429 1-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.49 (m, (ESI(+)) a]pyridin-7- 2H), 7.88 (s, 1H), 7.51 (d, J = 1.2 Hz, 1H), 7.37 m/e 438 ylmethyl)-3-[4- (s, 1H), 7.33 (m, 2H), 6.83 (dd, J = 6.9, 1.6 Hz, (M + H)+ ({1-[(propan-2- 1H), 6.74 (m, 2H), 6.64 (t, J = 6.0 Hz, 1H), 4.96 yloxy)acetyl]azetidin- (m, 1H), 4.60 (dd, J = 10.1, 6.4 Hz, 1H), 4.30 (m, 3- 3H), 4.11 (dd, J = 10.1, 3.9 Hz, 1H), 3.94 (s, 2H), yl}oxy)phenyl]urea 3.77 (dd, J = 10.7, 3.8 Hz, 1H), 3.58 (m, 1H), 1.09 (d, J = 6.1 Hz, 6H) 430 1-(4-{[1-(2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.48 (m, (ESI(+)) hydroxy-2- 2H), 7.88 (s, 1H), 7.51 (s, 1H), 7.38 (s, 1H), 7.33 m/e 424 methylpropanoyl)azetidin- (m, 2H), 6.83 (dd, J = 6.9, 1.6 Hz, 1H), 6.74 (m, (M + H)+ 3- 2H), 6.63 (t, J = 6.0 Hz, 1H), 5.13 (s, 1H), 4.91 yl]oxy}phenyl)- (m, 1H), 4.78 (m, 1H), 4.32 (d, J = 6.0 Hz, 3H), 3-(imidazo[1,2- 4.26 (m, 1H), 3.73 (m, 1H), 1.25 (s, 6H) a]pyridin-7- ylmethyl)urea 431 1-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.49 (m, (ESI(+)) a]pyridin-7- 2H), 7.88 (s, 1H), 7.51 (d, J = 1.2 Hz, 1H), 7.37 m/e 436 ylmethyl)-3-[4- (s, 1H), 7.33 (m, 2H), 6.83 (dd, J = 6.9, 1.6 Hz, (M + H)+ ({1-[(2R)- 1H), 6.74 (m, 2H), 6.63 (t, J = 6.0 Hz, 1H), 4.95 tetrahydrofuran- (m, 1H), 4.66 (m, 1H), 4.31 (m, 4H), 4.13 (m, 2- 1H), 3.75 (m, 3H), 2.03 (m, 1H), 1.93 (m, 1H), ylcarbonyl]azetidin- 1.81 (m, 2H) 3- yl}oxy)phenyl]urea 432 1-(imidazo[1,2- - 1H NMR (400 MHz, DMSO-d6) δ ppm 8.49 (m, (ESI(+)) a]pyridin-7- 2H), 7.88 (s, 1H), 7.51 (d, J = 1.2 Hz, 1H), 7.37 m/e 436 ylmethyl)-3-[4- (s, 1H), 7.33 (m, 2H), 6.83 (dd, J = 6.9, 1.6 Hz, (M + H)+ ({1-[(2S)- 1H), 6.74 (m, 2H), 6.64 (t, J = 6.0 Hz, 1H), 4.95 tetrahydrofuran- (m, 1H), 4.66 (m, 1H), 4.3123 (m, 4H), 4.13 (m, 2- 1H), 3.75 (m, 3H), 2.03 (m, 1H), 1.93 (m, 1H), ylcarbonyl]azetidin- 1.81 (m, 2H) 3- yl}oxy)phenyl]urea 433 1-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.48 (m, (ESI(+)) a]pyridin-7- 2H), 7.88 (d, J = 1.1 Hz, 1H), 7.51 (d, J = 1.2 Hz, m/e 450 ylmethyl)-3-(4- 1H), 7.37 (s, 1H), 7.33 (m, 2H), 6.83 (dd, J = 6.9, (M + H)+ {[1-(tetrahydro- 1.7 Hz, 1H), 6.74 (m, 2H), 6.64 (t, J = 6.0 Hz, 2H-pyran-4- 1H), 4.95 (m, 1H), 4.60 (dd, J = 9.4, 6.5 Hz, 1H), ylcarbonyl)azetidin- 4.32 (d, J = 6.0 Hz, 3H), 4.26 (m, 1H), 4.11 (dd, J = 3- 9.5, 3.8 Hz, 1H), 3.84 (m, 2H), 3.74 (dd, J = yl]oxy}phenyl)urea 10.6, 3.9 Hz, 1H), 3.36-3.26 (m, 2H), 1.57 (m, 4H) 434 1-(4-{[1-(1,4- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.48 (d, (ESI(+)) dioxan-2- 2H), 7.88 (s, 1H), 7.51 (s, 1H), 7.37 (s, 1H), 7.33 m/e 452 ylcarbonyl)azetidin- (m, 2H), 6.83 (dd, J = 6.9, 1.6 Hz, 1H), 6.74 (m, (M + H)+ 3- 2H), 6.64 (t, J = 6.0 Hz, 1H), 4.96 (m, 1H), 4.69 yl]oxy}phenyl)- (m, 1H), 4.30 (m, 3H), 4.18 (m, 2H), 3.76 (m, 3-(imidazo[1,2- 3H), 3.65-3.45 (m, 4H) a]pyridin-7- ylmethyl)urea 435 1-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.51 (s, (ESI(+)) a]pyridin-7- 1H), 8.48 (dd, J = 6.9, 0.9 Hz, 1H), 7.88 (d, J = m/e 464 ylmethyl)-3-(4- 1.1 Hz, 1H), 7.51 (d, J = 1.2 Hz, 1H), 7.37 (s, (M + H)+ {[1-(tetrahydro- 1H), 7.33 (m, 2H), 6.83 (dd, J = 6.9, 1.7 Hz, 1H), 2H-pyran-4- 6.74 (m, 2H), 6.64 (t, J = 6.0 Hz, 1H), 4.94 (m, ylacetyl)azetidin- 1H), 4.52 (m, 1H), 4.32 (d, J = 6.0 Hz, 2H), 4.25 3- (m, 1H), 4.04 (dd, J = 9.5, 3.9 Hz, 1H), 3.76 (m, yl]oxy}phenyl)urea 3H), 3.27 (m, 2H), 2.02 (d, J = 1.9 Hz, 2H), 1.87 (m, 1H), 1.54 (m, 2H), 1.19 (m, 2H) - The title compound was prepared as described in Example 321A-C, substituting (S)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate for (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate in Example 321A. 1H NMR (400 MHz, methanol-d4) δ ppm 8.41-8.35 (m, 1H), 7.91-7.83 (m, 2H), 7.81-7.76 (m, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.47-7.43 (m, 1H), 7.06-6.98 (m, 2H), 6.93 (dd, J=7.1, 1.5 Hz, 1H), 5.12-5.05 (m, 1H), 4.62 (bs, 2H), 3.68-3.39 (m, 4H), 2.25-2.13 (m, 2H), 1.49-1.43 (m, 9H).; MS (ESI(+)) m/e 437 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3,6-dihydropyridine-1(2H)-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 1-(2-fluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.77-8.70 (m, 1H), 8.19-8.15 (m, 1H), 8.00-7.96 (m, 1H), 7.95-7.88 (m, 1H), 7.80 (s, 1H), 7.53-7.41 (m, 6H), 7.30-7.15 (m, 2H), 6.26-5.95 (m, 1H), 4.61 (bs, 2H), 4.41-4.31 (m, 1H), 4.17-4.08 (m, 1H), 4.02-3.93 (m, 1H), 3.69-3.59 (m, 1H), 2.67-2.52 (m, 2H); MS (ESI(+)) m/e 470 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 1-(2-fluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 3-methylbutan-1-amine and 2-(tetrahydro-2H-pyran-4-yl)acetic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.74 (dd, J=7.0, 0.9 Hz, 1H), 8.18-8.15 (m, 1H), 7.98 (d, J=2.2 Hz, 1H), 7.92 (t, J=8.5 Hz, 1H), 7.82-7.78 (m, 1H), 7.47 (dd, J=7.0, 1.6 Hz, 1H), 7.28-7.15 (m, 2H), 6.16-6.10 (m, 1H), 4.61 (bs, 2H), 4.25-4.16 (m, 2H), 3.96-3.87 (m, 2H), 3.83-3.72 (m, 2H), 3.48-3.37 (m, 2H), 2.61-2.54 (m, 1H), 2.53-2.46 (m, 1H), 2.45-2.34 (m, 2H), 2.11-1.97 (m, 1H), 1.73-1.62 (m, 2H), 1.42-1.27 (m, 2H); MS (ESI(+)) m/e 492 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-(piperidin-4-yloxy)phenyl)urea for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.48 (m, 2H), 7.88 (s, 1H), 7.51 (s, 1H), 7.37 (s, 1H), 7.31 (m, 2H), 6.87 (m, 2H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.62 (t, J=6.0 Hz, 1H), 4.48 (m, 1H), 4.32 (d, J=6.0 Hz, 2H), 3.85 (m, 1H), 3.74 (m, 1H), 3.35 (m, 1H), 3.22 (m, 1H), 2.88 (m, 1H), 1.88 (m, 2H), 1.49 (m, 2H), 0.99 (d, J=6.7 Hz, 6H); (ESI(+)) m/e 436 (M+H).
-
TABLE 21 The following Examples were prepared essentially as described in Example 442, substituting the appropriate carboxylic acid in Example 442B. Ex Name 1H NMR MS 443 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.48 (ESI(+)) a]pyridin-7- (m, 2H), 7.88 (s, 1H), 7.51 (s, 1H), 7.37 (s, m/e 450 ylmethyl)-3-[4-({1- 1H), 7.31 (m, 2H), 6.87 (m, 2H), 6.83 (dd, J = (M + H)+ [(2S)-2- 7.0, 1.6 Hz, 1H), 6.65 (t, J = 6.0 Hz, 1H), 4.49 methylbutanoyl]piper- (m, 1H), 4.32 (d, J = 6.0 Hz, 2H), 3.84 (m, idin-4- 2H), 3.26 (m, 2H), 2.72 (m, 1H), 1.90 (m, yl}oxy)phenyl]urea 2H), 1.51 (m, 3H), 1.29 (m, 1H), 0.97 (d, J = 6.7 Hz, 3H), 0.81 (t, J = 7.4 Hz, 3H) 444 1-(4-{[1- - 1H NMR (500 MHz, DMSO-d6) δ ppm 8.48 (ESI(+)) (cyclopropylacetyl) (m, 2H), 7.88 (s, 1H), 7.51 (s, 1H), 7.37 (s, m/e 448 piperidin-4- 1H), 7.31 (m, 2H), 6.87 (m, 2H), 6.83 (dd, J = (M + H)+ yl]oxy}phenyl)-3- 7.0, 1.6 Hz, 1H), 6.62 (t, J = 6.0 Hz, 1H), 4.47 (imidazo[1,2- (m, 1H), 4.32 (d, J = 6.0 Hz, 2H), 3.85 (m, a]pyridin-7- 1H), 3.66 (m, 1H), 3.30 (m, 1H), 3.22 (m, ylmethyl)urea 1H), 2.26 (d, J = 6.8 Hz, 2H), 1.91 (m, 2H), 1.50 (m, 2H), 0.95 (m, 1H), 0.44 (m, 2H), 0.11 (m, 2H) 445 1-{4-[(1- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.48 (ESI(+)) benzoylpiperidin-4- (m, 2H), 7.88 (s, 1H), 7.51 (s, 1H), 7.44 (m, m/e 470 yl)oxy]phenyl}-3- 3H), 7.40 (m, 2H), 7.37 (m, 1H), 7.31 (m, (M + H)+ (imidazo[1,2- 2H), 6.87 (m, 2H), 6.83 (dd, J = 7.0, 1.6 Hz, a]pyridin-7- 1H), 6.63 (t, J = 6.0 Hz, 1H), 4.52 (m, 1H), ylmethyl)urea 4.31 (d, J = 6.0 Hz, 2H), 3.96 (m, 1H), 3.52 (m, 1H), 3.45-3.20 (m, 2H), 1.91 (m, 2H), 1.59 (m, 2H) 446 1-(imidazo[1,2- 1H NMR (400 MHz, DMSO-d6) δ ppm 8.48 (ESI(+)) a]pyridin-7- (m, 2H), 7.88 (m, 1H), 7.51 (d, J = 1.2 Hz, m/e 466 ylmethyl)-3-[4-({1- 1H), 7.37 (m, 1H), 7.31 (m, 2H), 6.87 (m, (M + H)+ [(propan-2- 2H), 6.83 (dd, J = 7.0, 1.6 Hz, 1H), 6.64 (m, yloxy)acetyl]piper- 1H), 4.49 (m, 1H), 4.32 (d, J = 6.0 Hz, 2H), idin-4- 4.08 (s, 2H), 3.82 (m, 1H), 3.67 (m, 1H), yl}oxy)phenyl]urea 3.59(m, 1H), 3.40-3.15 (m, 2H), 1.90 (m, 2H), 1.52 (m, 2H), 1.10 (d, J = 6.1 Hz, 6H) 447 1-(4-{[1-(2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.48 (ESI(+)) hydroxy-2- (m, 2H), 7.88 (s, 1H), 7.52 (d, J = 1.2 Hz, m/e 452 methylpropanoyl)piper- 1H), 7.38 (s, 1H), 7.30 (m, 2H), 6.87 (m, 2H), (M + H)+ idin-4- 6.83 (dd, J = 7.0, 1.6 Hz, 1H), 6.62 (t, J = 6.0 yl]oxy}phenyl)-3- Hz, 1H), 5.39 (s, 1H), 4.48 (m, 1H), 4.32 (d, J = (imidazo[1,2- 6.0 Hz, 2H), 4.10-3.40 (m, 2H), 3.40- a]pyridin-7- 3.15 (m, 2H), 1.90 (m, 2H), 1.54 (m, 2H), ylmethyl)urea 1.31 (s, 6H) 448 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.49 (ESI(+)) a]pyridin-7- (m, 2H), 7.90 (s, 1H), 7.54 (d, J = 1.2 Hz, m/e 464 ylmethyl)-3-[4-({1- 1H), 7.39 (s, 1H), 7.31 (m, 2H), 6.86 (m, 3H), (M + H)+ [(2R)- 6.62 (t, J = 6.0 Hz, 1H), 4.67 (m, 1H), 4.48 tetrahydrofuran-2- (m, 1H), 4.32 (d, J = 6.0 Hz, 2H), 3.78 (m, ylcarbonyl]piper- 4H), 3.45-3.15 (m, 2H), 2.10-1.75 (m, 6H), idin-4- 1.53 (m, 2H) yl}oxy)phenyl]urea 449 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.48 (ESI(+)) a]pyridin-7- (m, 2H), 7.89 (s, 1H), 7.52 (d, J = 1.2 Hz, m/e 464 ylmethyl)-3-[4-({1- 1H), 7.38 (s, 1H), 7.31 (m, 2H), 6.87 (m, 2H), (M + H)+ [(2S)- 6.83 (dd, J = 7.0, 1.6 Hz, 1H), 6.62 (t, J = 6.0 tetrahydrofuran-2- Hz, 1H), 4.67 (m, 1H), 4.48 (m, 1H), 4.32 (d, ylcarbonyl]piper- J = 6.0 Hz, 2H), 3.78 (m, 4H), 3.45-3.16 (m, idin-4- 2H), 2.09-1.92 (m, 2H), 2.09-1.92 (m, 4H), yl}oxy)phenyl]urea 1.53 (m, 2H) 450 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.48 (ESI(+)) a]pyridin-7- (m, 2H), 7.88 (s, 1H), 7.51 (d, J = 1.2 Hz, m/e 478 ylmethyl)-3-(4-{[1- 1H), 7.38 (s, 1H), 7.31 (m, 2H), 6.87 (m, 2H), (M + H)+ (tetrahydro-2H- 6.83 (dd, J = 7.0, 1.6 Hz, 1H), 6.62 (t, J = 6.0 pyran-4- Hz, 1H), 4.48 (m, 1H), 4.32 (d, J = 6.0 Hz, ylcarbonyl)piper- 2H), 3.88-3.71 (m, 4H), 3.38 (m, 2H), 3.34- idin-4- 3.16 (m, 1H), 3.22 (m, 1H), 2.89 (m, 1H), yl]oxy}phenyl)urea 1.91 (m, 2H), 1.67-1.40 (m, 6H) 451 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.48 (ESI(+)) a]pyridin-7- (m, 2H), 7.88 (s, 1H), 7.52 (bs, 1H), 7.38 (bs, m/e 492 ylmethyl)-3-(4-{[1- 1H), 7.31 (m, 2H), 6.87 (m, 2H), 6.83 (dd, J = (M + H)+ (tetrahydro-2H- 7.0, 1.5 Hz, 1H), 6.62 (t, J = 6.0 Hz, 1H), 4.47 pyran-4- (m, 1H), 4.32 (d, J = 6.0 Hz, 2H), 3.89-3.75 ylacetyl)piper- (m, 3H), 3.70 (m, 1H), 3.40-3.17 (m, 4H), idin-4- 2.26 (m, 2H), 1.89 (m, 3H), 1.60-1.40 (m, yl]oxy}phenyl)urea 4H), 1.19 (m, 2H) 726 1-(4-{[1-(3- (ESI(+)) fluorobenzoyl)piper- m/e 488 idin-4- (M + H)+ yl]oxy}phenyl)-3- (imidazo[1,2- a]pyridin-7- ylmethyl)urea 727 1-(4-{[1-(2,4- (ESI(+)) difluorobenzoyl)piper- m/e 506 idin-4- (M + H)+ yl]oxy}phenyl)-3- (imidazo[1,2- a]pyridin-7- ylmethyl)urea 728 1-(4-{[1-(2,5- (ESI(+)) difluorobenzoyl)piper- m/e 506 idin-4- (M + H)+ yl]oxy}phenyl)-3- (imidazo[1,2- a]pyridin-7- ylmethyl)urea 729 1-(4-{[1-(3,4- (ESI(+)) difluorobenzoyl)piper- m/e 506 idin-4- (M + H)+ yl]oxy}phenyl)-3- (imidazo[1,2- a]pyridin-7- ylmethyl)urea 730 1-(4-{[1-(3,5- difluorobenzoyl)piper- (ESI(+)) idin-4- m/e 506 yl]oxy}phenyl)-3- (M + H)+ (imidazo[1,2- a]pyridin-7- ylmethyl)urea - The title compound was prepared as described in Example 28A, substituting tert-butyl 3-(4-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)phenyl)azetidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 1-(4-(azetidin-3-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.66 (s, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.88 (s, 1H), 7.51 (s, 1H), 7.39 (m, 3H), 7.22 (m, 2H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.70 (t, J=6.0 Hz, 1H), 4.52 (m, 1H), 4.33 (d, J=6.0 Hz, 2H), 4.20 (m, 1H), 4.08 (dd, J=8.5, 5.3 Hz, 1H), 3.76 (m, 2H), 2.49 (m, 1H), 0.99 (d, J=6.8 Hz, 6H); (ESI(+)) m/e 392 (M+H)+.
-
TABLE 22 The following Examples were prepared essentially as described in Example 452, substituting the appropriate carboxylic acid in Example 452B. Ex Name 1H NMR MS 453 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.66 (s, (ESI(+)) a]pyridin-7- 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (s, 1H), 7.52 m/e 406 ylmethyl)-3-(4- (s, 1H), 7.40 (m, 3H), 7.22 (m, 2H), 6.84 (dd, J = (M + H)+ {1-[(2S)-2- 7.0, 1.6 Hz, 1H), 6.70 (m, 1H), 4.52 (m, 1H), methylbutan- 4.33 (d, J = 6.0 Hz, 2H), 4.21 (m, 1H), 4.06 (m, oyl]azetidin-3- 1H), 3.76 (m, 2H), 2.27 (m, 1H), 1.50 (m, 1H), yl}phenyl)urea 1.30 (m, 1H), 0.98 (d, J = 6.8 Hz, 3H), 0.84 (t, J = 7.4 Hz, 3H) 454 1-{4-[1- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.66 (s, (ESI(+)) (cyclopropylace- 1H), 8.49 (d, J = 7.0 Hz, 1H), 7.89 (s, 1H), 7.53 m/e 404 tyl)azetidin-3- (d, J = 1.2 Hz, 1H), 7.40 (m, 3H), 7.22 (m, 2H), (M + H)+ yl]phenyl}-3- 6.85 (dd, J = 7.0, 1.6 Hz, 1H), 6.70 (t, J = 6.0 (imidazo[1,2- Hz, 1H), 4.45 (m, 1H), 4.33 (d, J = 6.0 Hz, 2H), a]pyridin-7- 4.20 (m, 1H), 4.04 (m, 1H), 3.75 (m, 2H), 2.02 ylmethyl)urea (d, J = 6.8 Hz, 2H), 0.94 (m, 1H), 0.44 (m, 2H), 0.11 (m, 2H) 455 1-[4-(1- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.68 (s, (ESI(+)) benzoylazetidin- 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (s, 1H), 7.68 m/e 426 3-yl)phenyl]-3- (m, 2H), 7.52 (m, 2H), 7.46 (m, 2H), 7.40 (m, (M + H)+ (imidazo[1,2- 3H), 7.26 (m, 2H), 6.83 (dd, J = 7.0, 1.6 Hz, a]pyridin-7- 1H), 6.72 (t, J = 6.0 Hz, 1H), 464 (m, 1H), 4.44 ylmethyl)urea (m, 1H), 4.33 (d, J = 6.0 Hz, 2H), 4.27 (m, 1H), 3.98 (m, 1H), 3.85 (m, 1H) 456 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.67 (s, (ESI(+)) a]pyridin-7- 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (s, 1H), 7.51 m/e 422 ylmethyl)-3-(4- (d, J = 1.2 Hz, 1H), 7.40 (m, 3H), 7.22 (m, 2H), (M + H)+ {1-[(propan-2- 6.83 (dd, J = 7.0, 1.6 Hz, 1H), 6.71 (t, J = 6.0 yloxy)ace- Hz, 1H), 4.56 (m, 1H), 4.33 (d, J = 6.0 Hz, 2H), tyl]azetidin-3- 4.24 (m, 1H), 4.13 (m, 1H), 3.95 (s, 2H), 3.79 yl}phenyl)urea (m, 2H), 3.59 (m, 1H), 1.10 (d, J = 6.1 Hz, 6H) 457 1-{4-[1-(2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.66 (s, (ESI(+)) hydroxy-2- 1H), 8.50 (d, J = 7.0 Hz, 1H), 7.90 (s, 1H), 7.54 m/e 408 methylpropanoyl) (d, J = 1.2 Hz, 1H), 7.40 (m, 3H), 7.21 (m, 2H), (M + H)+ azetidin-3- 6.86 (dd, J = 7.0, 1.6 Hz, 1H), 6.70 (t, J = 6.0 yl]phenyl}-3- Hz, 1H), 5.09 (s, 1H), 4.75 (m, 1H), 4.32 (m, (imidazo[1,2- 3H), 4.22 (m, 1H), 3.74 (m, 2H), 1.27 (s, 6H) a]pyridin-7- ylmethyl)urea 458 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.73 (s, (ESI(+)) a]pyridin-7- 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (s, 1H), 7.51 m/e 420 ylmethyl)-3-(4- (s, 1H), 7.40 (m, 3H), 7.22 (m, 2H), 6.83 (dd, J = (M + H)+ (1-[(2R)- 7.0, 1.6 Hz, 1H), 6.78 (t, J = 6.0 Hz, 1H), 4.60 tetrahydrofuran-2- (m, 1H), 4.37 (m, 1H), 4.33 (d, J = 6.0 Hz, 2H), ylcarbon- 4.24 (m, 1H), 4.16 (m, 1H), 3.86-3.69 (m, yl]azetidin-3- 4H), 2.04 (m, 1H), 1.96 (m, 1H), 1.82 (m, 2H) yl}phenyl)urea 459 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.66 (s, (ESI(+)) a]pyridin-7- 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (s, 1H), 7.51 m/e 420 ylmethyl)-3-(4- (s, 1H), 7.40 (m, 3H), 7.22 (m, 2H), 6.83 (dd, J = (M + H)+ {1-[(2S)- 7.0, 1.6 Hz, 1H), 6.74-6.67 (m, 1H), 4.60 tetrahydrofuran-2- (m, 1H), 4.37 (m, 1H), 4.33 (d, J = 6.0 Hz, 2H), ylcarbon- 4.23 (m, 1H), 4.15 (m, 1H), 3.85-3.69 (m, yl]azetidin-3- 4H), 2.04 (m, 1H), 1.96 (m, 1H), 1.81 (m, 2H) yl}phenyl)urea 460 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.67 (s, (ESI(+)) a]pyridin-7- 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (s, 1H), 7.51 m/e 434 ylmethyl)-3-{4- (d, J = 1.1 Hz, 1H), 7.40 (m, 3H), 7.22 (m, 2H), (M + H)+ [1-(tetrahydro- 6.83 (dd, J = 7.0, 1.6 Hz, 1H), 6.71 (t, J = 6.0 2H-pyran-4- Hz, 1H), 4.54 (m, 1H), 4.33 (d, J = 6.0 Hz, 2H), ylcarbon- 4.21 (m, 1H), 4.13 (m, 1H), 3.85 (m, 2H), 3.77 yl)azetidin-3- (m, 2H), 3.40-3.25 (m, 2H), 2.50 (m, 1H), yl]phenyl}urea 1.58 (m, 4H) 461 1-(imidazo[1,2- 1H NMR (500 MHz, DMSO-d6) δ ppm 8.70 (s, (ESI(+)) a]pyridin-7- 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (s, 1H), 7.51 m/e 448 ylmethyl)-3-{4- (s, 1H), 7.40 (m, 3H), 7.21 (m, 2H), 6.83 (dd, J = (M + H)+ [1-(tetrahydro- 7.0, 1.6 Hz, 1H), 6.75 (t, J = 6.0 Hz, 1H), 4.47 2H-pyran-4- (m, 1H), 4.33 (d, J = 6.0 Hz, 2H), 4.19 (m, 1H), ylacetyl)azetidin- 4.05 (m, 1H), 3.85-3.69 (m, 4H), 3.28 (m, 3-yl]phenyl}urea 2H), 2.03 (d, J = 1.8 Hz, 2H), 1.90 (m, 1H), 1.57 (m, 2H), 1.21 (m, 2H) - The title compound was prepared as described in Example 52A, substituting 2-cyclopentylacetyl chloride for 2-cyclopentylacetyl chloride and methyl 4-amino-2-fluorobenzoate for methyl 4-aminobenzoate.
- The title compound was prepared as described in Example 4B, substituting methyl 4-(2-cyclopentylacetamido)-2-fluorobenzoate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)-2-fluorobenzoic acid for 4-nitrobenzoic acid. 1H NMR (501 MHz, DMSO-d6) δ ppm 10.24 (s, 1H), 8.70-8.63 (m, 1H), 8.46 (s, 1H), 7.95 (s, 1H), 7.74-7.62 (m, 2H), 7.58-7.50 (m, 2H), 7.32 (dd, J=8.5, 1.9 Hz, 1H), 7.24 (dd, J=9.2, 1.7 Hz, 1H), 4.45 (d, J=5.9 Hz, 2H), 2.37-2.31 (m, 2H), 2.31-2.15 (m, 1H), 1.81-1.69 (m, 2H), 1.67-1.45 (m, 4H), 1.25-1.12 (m, 2H); MS (ESI(+)) m/e 395 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.34 (t, J=6.0 Hz, 1H), 8.87 (d, J=7.0 Hz, 1H), 8.51 (d, J=2.5 Hz, 1H), 8.33 (d, J=2.2 Hz, 1H), 8.15 (d, J=2.1 Hz, 1H), 7.90 (dd, J=8.9, 2.6 Hz, 1H), 7.85 (d, J=3.9 Hz, 1H), 7.81 (s, 1H), 7.50-7.44 (m, 2H), 6.94 (d, J=9.0 Hz, 1H), 4.67 (d, J=5.9 Hz, 2H), 3.75-3.66 (m, 4H), 3.57-3.49 (m, 4H); MS (ESI(+)) m/e 420 (M+H).
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 3-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)pyrrolidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(pyrrolidin-3-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.02 (t, J=5.4 Hz, 1H), 8.48 (d, J=6.8 Hz, 1H), 7.88 (s, 1H), 7.68 (dd, J=3.9, 2.2 Hz, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.37 (s, 1H), 7.02 (dd, J=8.1, 3.7 Hz, 1H), 6.82 (dd, J=7.0, 1.5 Hz, 1H), 4.46 (d, J=5.8 Hz, 2H), 3.22-3.94 (m, 5H), 2.21-2.42 (m, 1H), 2.10-2.17 (m, 2H), 1.86-2.09 (m, 2H), 0.86-0.95 (m, 6H); MS (ESI(+)) m/e 411 (M+H)+.
-
TABLE 23 The following Examples were prepared essentially as described in Example 467, using an appropriate carboxylic acid in Example 467C. Ex Name MS 540 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3- (ESI(+)) trifluoropropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide m/e 437 (M + H)+ 541 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2- (ESI(+)) methylpropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide m/e 397 (M + H)+ 542 5-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)thiophene-2-carboxamide m/e 431 (M + H)+ 717 5-[1-(cyclopropylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)thiophene-2-carboxamide m/e 395 (M + H)+ 718 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4- (ESI(+)) methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide m/e 445 (M + H)+ 756 5-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)thiophene-2-carboxamide m/e 409 (M + H)+ 757 5-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)thiophene-2-carboxamide m/e 465 (M + H)+ 758 5-{1-[(4-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)thiophene-2-carboxamide m/e 463 (M + H)+ 759 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3- (ESI(+)) methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide m/e 461 (M + H)+ 760 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2- (ESI(+)) methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide m/e 461 (M + H)+ 761 5-{1-[(3-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)thiophene-2-carboxamide m/e 463 (M + H)+ 762 5-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)thiophene-2-carboxamide m/e 449 (M + H)+ 763 5-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)thiophene-2-carboxamide m/e 449 (M + H)+ 764 5-{1-[(3,5-difluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)thiophene-2-carboxamide m/e 481 (M + H)+ 765 5-{1-[(2-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)thiophene-2-carboxamide m/e 463 (M + H)+ 766 5-[1-(4-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)thiophene-2-carboxamide m/e 456 (M + H)+ 767 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3- (ESI(+)) yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide m/e 425 (M + H)+ 768 5-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)thiophene-2-carboxamide m/e 467 (M + H)+ 769 5-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)thiophene-2-carboxamide m/e 421 (M + H)+ 770 5-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)thiophene-2-carboxamide m/e 465 (M + H)+ 771 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrro1-2- (ESI(+)) yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide m/e 434 (M + H)+ 772 5-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)thiophene-2-carboxamide m/e 467 (M + H)+ 773 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-4- (ESI(+)) ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide m/e 432 (M + H)+ 774 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-2- (ESI(+)) ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide m/e 432 (M + H)+ 775 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrazol- (ESI(+)) 4-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide m/e 435 (M + H)+ 776 5-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)thiophene-2-carboxamide m/e 449 (M + H)+ 777 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2E)-2-methylpent-2- (ESI(+)) enoyl]pyrrolidin-3-yl}thiophene-2-carboxamide m/e 423 (M + H)+ 778 5-{1-[(2,5-dimethylfuran-3-yl)carbonyl]pyrrolidin-3-yl}-N- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide m/e 449 (M + H)+ 779 5-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)thiophene-2-carboxamide m/e 465 (M + H)+ 780 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-propanoylpyrrolidin-3- (ESI(+)) yl)thiophene-2-carboxamide m/e 383 (M + H)+ 781 5-{1-[(1-cyanocyclopropyl)carbonyl]pyrrolidin-3-yl}-N- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide m/e 420 (M + H)+ 782 5-(1-butanoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)thiophene-2-carboxamide m/e 397 (M + H)+ 783 5-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)thiophene-2-carboxamide m/e 421 (M + H)+ 784 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4- (ESI(+)) methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide m/e 461 (M + H)+ 785 5-[1-(2,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)thiophene-2-carboxamide m/e 467 (M + H)+ 786 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(thiophen-2- (ESI(+)) ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide m/e 437 (M + H)+ 787 5-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)thiophene-2-carboxamide m/e 411 (M + H)+ 788 5-[1-(3, 3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)thiophene-2-carboxamide m/e 425 (M + H)+ 791 5-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)thiophene-2-carboxamide m/e 425 (M + H)+ 792 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyrazin-2- (ESI(+)) ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide m/e 433 (M + H)+ 793 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylthiophen-2- (ESI(+)) yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide m/e 451 (M + H)+ 794 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2- (ESI(+)) methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide m/e 445 (M + H)+ 795 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1- (ESI(+)) methylcyclopropyl)carbonyl]pyrrolidin-3-yl}thiophene-2- m/e 409 carboxamide (M + H)+ 796 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4- (ESI(+)) trifluorobutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide m/e 451 (M + H)+ 797 5-{1-[(3,5-dimethyl-1,2-oxazo1-4-yl)carbonyl]pyrrolidin-3-yl}-N- (ESI(+)) (imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide m/e 450 (M + H)+ 798 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-3- (ESI(+)) ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide m/e 432 (M + H)+ 799 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrazol- (ESI(+)) 5-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide m/e 435 (M + H)+ 800 5-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)thiophene-2-carboxamide m/e 425 (M + H)+ - The title compound was prepared as described in Example 324A, substituting N-cyclobutylidene-2-methylpropane-2-sulfinamide for N-(oxetan-3-ylidene)propane-2-sulfinamide.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(1-(1,1-dimethylethylsulfinamido)cyclobutyl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid.
- The title compound was prepared in Example 324C, substituting 5-(1-(1,1-dimethylethylsulfinamido)cyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 5-(3-(1,1-dimethylethylsulfinamido)oxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide.
- The title compound was prepared as described in Example 1A, substituting 5-(1-aminocyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.97 (t, J=5.9 Hz, 1H), 8.53 (s, 1H), 8.48 (d, J=7.1 Hz, 1H), 7.88 (s, 1H), 7.63 (d, J=3.7 Hz, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.38 (s, 1H), 7.04 (d, J=3.7 Hz, 1H), 6.82 (dd, J=6.8, 1.7 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 2.36-2.48 (m, 5H), 1.86-2.01 (m, 2H), 0.99 (d, J=6.8 Hz, 6H); MS (ESI(+)) m/e 397 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 5-(1-aminocyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.97 (t, J=5.9 Hz, 1H), 8.59 (s, 1H), 8.48 (d, J=7.8 Hz, 1H), 7.88 (s, 1H), 7.63 (d, J=4.1 Hz, 1H), 7.51 (d, J=1.0 Hz, 1H), 7.37 (s, 1H), 7.05 (d, J=3.7 Hz, 1H), 6.82 (dd, J=7.1, 1.7 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 2.39-2.47 (m, 4H), 1.83-2.03 (m, 5H), 0.87 (d, J=6.4 Hz, 6H); MS (ESI(+)) m/e 411 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 5-(1-aminocyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (S)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.97 (t, J=6.1 Hz, 1H), 8.57 (s, 1H), 8.47 (d, J=7.1 Hz, 1H), 7.88 (s, 1H), 7.63 (d, J=4.1 Hz, 1H), 7.51 (d, J=1.4 Hz, 1H), 7.37 (s, 1H), 7.04 (d, J=3.7 Hz, 1H), 6.82 (dd, J=7.0, 1.5 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 2.37-2.49 (m, 4H), 2.13-2.26 (m, 1H), 1.84-2.01 (m, 2H), 1.40-1.59 (m, 1H), 1.20-1.36 (m, 1H), 0.97 (d, J=6.8 Hz, 3H), 0.82 (t, J=7.3 Hz, 3H); MS (ESI(+)) m/e 411 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 5-(1-aminocyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.17 (s, 1H), 8.98 (t, J=5.9 Hz, 1H), 8.46 (d, J=6.1 Hz, 1H), 7.84-7.90 (m, 3H), 7.65 (d, J=4.1 Hz, 1H), 7.43-7.57 (m, 4H), 7.37 (s, 1H), 7.14 (d, J=4.1 Hz, 1H), 6.81 (dd, J=6.8, 1.7 Hz, 1H), 4.44 (d, J=6.1 Hz, 2H), 2.61-2.73 (m, 2H), 2.50-2.60 (m, 2H), 1.91-2.07 (m, 2H); MS (ESI(+)) m/e 431 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 5-(1-aminocyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 3,3,3-trifluoropropanoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.08 (s, 1H), 9.00 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.8 Hz, 1H), 7.88 (s, 1H), 7.65 (d, J=3.7 Hz, 1H), 7.52 (s, 1H), 7.38 (s, 1H), 7.07 (d, J=3.7 Hz, 1H), 6.83 (dd, J=6.8, 1.7 Hz, 1H), 4.46 (d, J=5.8 Hz, 2H), 3.19-3.36 (m, 2H), 2.43-2.53 (m, 4H), 1.86-2.03 (m, 2H); MS (ESI(+)) m/e 437 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 5-(1-aminocyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and tetrahydro-2H-pyran-4-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.97 (t, J=6.1 Hz, 1H), 8.60 (s, 1H), 8.48 (d, J=7.1 Hz, 1H), 7.88 (s, 1H), 7.63 (d, J=3.7 Hz, 1H), 7.51 (d, J=1.0 Hz, 1H), 7.37 (s, 1H), 7.04 (d, J=3.7 Hz, 1H), 6.82 (dd, J=7.0, 1.5 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 3.81-3.89 (m, 2H), 3.24-3.36 (m, 2H), 2.33-2.48 (m, 5H), 1.84-2.00 (m, 2H), 1.47-1.65 (m, 4H); MS (ESI(+)) m/e 439 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)azetidin-3-yloxy)benzoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.98 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.89 (m, 3H), 7.51 (d, J=1.1 Hz, 1H), 7.37 (s, 1H), 6.92 (m, 2H), 6.84 (dd, J=7.0, 1.6 Hz, 1H), 5.06 (m, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.33 (m, 2H), 3.80 (m, 2H), 1.39 (s, 9H); MS (ESI(+)) m/e 423 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)piperidine-1-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-((4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)thiophen-2-yl)-1H-pyrazol-1-yl)methyl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate. 1H NMR (300 MHz, methanol-d4) δ 8.76 (dd, J=7.1, 0.9 Hz, 1H), 8.19 (dd, J=2.2, 0.7 Hz, 1H), 8.07 (s, 1H), 8.00 (d, J=2.2 Hz, 1H), 7.83 (d, J=0.6 Hz, 2H), 7.72 (d, J=3.8 Hz, 1H), 7.49 (dd, J=7.0, 1.6 Hz, 1H), 7.22 (d, J=3.9 Hz, 1H), 4.75 (s, 2H), 4.15 (d, J=7.0 Hz, 2H), 3.48-3.36 (m, 2H), 3.08-2.91 (m, 2H), 2.37-2.15 (m, 1H), 1.85 (d, J=14.0 Hz, 2H), 1.63-1.43 (m, 2H); MS (ESI(+)) m/e 421 (M+H)+.
- To a solution of imidazo[1,2-a]pyridin-7-ylmethanamine (500 mg, 3.40 mmol) in dichloromethane (17 ml) at room temperature was added 1-bromo-4-isocyanatobenzene (680 mg, 3.40 mmol) as a single portion. The resulting suspension was stirred overnight and then filtered with dichloromethane washes to give the title compound.
- The title compound was prepared as described in Example 51A, substituting substituting 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-propyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.62 (s, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 8.02 (d, J=0.8 Hz, 1H), 7.88 (dd, J=1.2, 0.7 Hz, 1H), 7.77 (d, J=0.8 Hz, 1H), 7.54-7.34 (m, 6H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.69 (t, J=6.0 Hz, 1H), 4.34 (d, J=5.9 Hz, 2H), 3.90 (d, J=7.1 Hz, 2H), 2.21-2.04 (m, 1H), 0.86 (d, J=6.7 Hz, 6H). MS (ESI(+)) m/e 389 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-propyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ 8.62 (s, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 8.04 (d, J=0.8 Hz, 1H), 7.90-7.86 (m, 1H), 7.76 (d, J=0.8 Hz, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.46-7.35 (m, 5H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.69 (t, J=6.0 Hz, 1H), 4.34 (d, J=5.9 Hz, 2H), 4.04 (t, J=6.9 Hz, 2H), 1.91-1.73 (m, 2H), 1.26-1.05 (m, 1H), 0.85 (t, J=7.4 Hz, 3H); MS (ESI(+)) m/e 375 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-phenoxybenzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.05 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.95 (m, 2H), 7.89 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.44 (m, 2H), 7.38 (s, 1H), 7.22 (m, 1H), 7.14-6.98 (m, 4H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.50 (d, J=5.9 Hz, 2H); MS (ESI(+)) m/e 344 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}azetidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting -(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 3-methylbutan-1-amine and 2-methylpropanoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.10 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.91 (m, 3H), 7.52 (d, J=1.0 Hz, 1H), 7.48 (m, 2H), 7.38 (s, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.58 (t, J=8.6 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 4.26 (t, J=9.0 Hz, 1H), 4.18 (dd, J=8.4, 6.0 Hz, 1H), 3.92 (m, 1H), 3.84 (m, 1H), 3.17 (d, J=5.0 Hz, 1H), 1.00 (dd, J=6.8, 1.6 Hz, 6H); MS (ESI(+)) m/e 377 (M+H)+.
-
TABLE 24 The following Examples were prepared essentially as described in Example 490, using an appropriate carboxylic acid in Example 490B. Ex Name MS 547 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2- (ESI(+)) methylbutanoyl]azetidin-3-yl}benzamide m/e 391 (M + H)+ 548 4-[1-(cyclopropylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 389 (M + H)+ 549 4-(1-benzoylazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 411 (M + H)+ 550 4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 393 (M + H)+ 551 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4- (ESI(+)) ylacetyl)azetidin-3-yl]benzamide m/e 433 (M + H)+ 552 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2- (ESI(+)) ylcarbonyl)azetidin-3-yl]benzamide m/e 417 (M + H)+ 628 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2- (ESI(+)) methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide m/e 389 (M + H)+ 629 4-[1-(cyclopentylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 417 (M + H)+ 630 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3- (ESI(+)) methylpentanoyl)azetidin-3-yl]benzamide m/e 405 (M + H)+ 631 4-[1-(cyclopentylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)benzamide m/e 403 (M + H)+ 632 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1- (ESI(+)) methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide m/e 389 (M + H)+ 633 4-[1-(2,2-dimethylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2- (ESI(+)) a]pyridin-7-ylmethyl)benzamide m/e 391 (M + H)+ 634 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazo1-5- (ESI(+)) ylcarbonyl)azetidin-3-yl]benzamide m/e 418 (M + H)+ 635 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2- (ESI(+)) ylcarbonyl)azetidin-3-yl]benzamide m/e 413 (M + H)+ 636 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2- (ESI(+)) methoxybenzoyl)azetidin-3-yl]benzamide m/e 441 (M + H)+ 637 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazo1-4- (ESI(+)) ylcarbonyl)azetidin-3-yl]benzamide m/e 418 (M + H)+ 638 4-[1-(2-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 429 (M + H)+ 639 4-[1-(furan-2-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 401 (M + H)+ 640 4-[1-(3-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 429 (M + H)+ 641 4-[1-(2,4-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 447 (M + H)+ 642 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol- (ESI(+)) 3-yl)carbonyl]azetidin-3-yl}benzamide m/e 415 (M + H)+ 643 4-[1-(2-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 445 (M + H)+ 644 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2- (ESI(+)) methylbenzoyl)azetidin-3-yl]benzamide m/e 425 (M + H)+ 645 4-[1-(4-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 445 (M + H)+ 646 4-[1-(3-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 445 (M + H)+ 647 4-[1-(2,2-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)benzamide m/e 405 (M + H)+ 648 4-[1-(3,5-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 447 (M + H)+ 649 4-[1-(4-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 429 (M + H)+ 650 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4- (ESI(+)) methylbenzoyl)azetidin-3-yl]benzamide m/e 425 (M + H)+ 651 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3- (ESI(+)) methylbutanoyl)azetidin-3-yl]benzamide m/e 391 (M + H)+ 652 4-[1-(3,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)benzamide m/e 405 (M + H)+ 653 4-[1-(3-cyanobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 436 (M + H)+ 654 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3- (ESI(+)) methoxybenzoyl)azetidin-3-yl]benzamide m/e 441 (M + H)+ 655 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4- (ESI(+)) methoxybenzoyl)azetidin-3-yl]benzamide m/e 441 (M + H)+ 565 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2- (ESI(+)) yl)carbonyl]azetidin-3-yl}benzamide m/e 414 (M + H)+ 657 4-[1-(cyclohexylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 431 (M + H)+ 658 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4- (ESI(+)) ylcarbonyl)azetidin-3-yl]benzamide m/e 412 (M + H)+ 659 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3- (ESI(+)) ylcarbonyl)azetidin-3-yl]benzamide m/e 412 (M + H)+ 660 4-[1-(cyclohexylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 417 (M + H)+ 661 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2- (ESI(+)) ylcarbonyl)azetidin-3-yl]benzamide m/e 412 (M + H)+ 662 4-[1-(furan-3-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7- (ESI(+)) ylmethyl)benzamide m/e 401 (M + H)+ 663 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrimidin-4- (ESI(+)) ylcarbonyl)azetidin-3-yl]benzamide m/e 413 (M + H)+ 664 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2- (ESI(+)) ylcarbonyl)azetidin-3-yl]benzamide m/e 418 (M + H)+ 665 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1- (ESI(+)) methylcyclohexyl)carbonyl]azetidin-3-yl} benzamide m/e 431 (M + H)+ 666 4-[1-(2,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin- (ESI(+)) 7-ylmethyl)benzamide m/e 405 (M + H)+ 667 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3- (ESI(+)) methylbenzoyl)azetidin-3-yl]benzamide m/e 425 (M + H)+ 668 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3- (ESI(+)) ylcarbonyl)azetidin-3-yl]benzamide m/e 417 (M + H)+ 669 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3- (ESI(+)) (trifluoromethoxy)benzoyl]azetidin-3-yl}benzamide m/e 495 (M + H)+ 670 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2- (ESI(+)) yl)carbonyl]azetidin-3-yl}benzamide m/e 431 (M + H)+ 671 N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3- (ESI(+)) (trifluoromethyl)benzoyl]azetidin-3-yl}benzamide m/e 479 (M + H)+ - A solution of tert-butyl 4-(4-(imidazo[1,2-a]pyridin-6-ylcarbamoyl)phenyl)piperidine-1-carboxylate (0.015 g, 0.036 mmol) in chloroform (0.618 ml) and methanol (0.095 ml) was treated with N-chlorosuccinimide (5.24 mg, 0.039 mmol) and the reaction was stirred at ambient temperature for 16 hours. The reaction mixture was concentrated under a stream of warm nitrogen. The residue was purified by normal phase flash chromatography to provide the title compound. 1H NMR (500 MHz, methanol-d4) δ ppm 9.23 (s, 1H), 7.93 (d, J=8.3 Hz, 2H), 7.62-7.51 (m, 3H), 7.42 (d, J=8.3 Hz, 2H), 4.27-4.19 (m, 2H), 2.96-2.76 (m, 3H), 1.90-1.82 (m, 2H), 1.70-1.57 (m, 2H), 1.48 (s, 9H); MS (ESI(+)) m/e 455 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl (3R)-3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}pyrrolidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting (R)—N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yloxy)benzamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, methanol-d4) δ ppm 8.75 (d, J=7.0 Hz, 1H), 8.17 (d, J=2.2 Hz, 1H), 7.99 (d, J=2.2 Hz, 1H), 7.94-7.86 (m, 2H), 7.80 (bs, 1H), 7.48 (dd, J=7.0, 1.6 Hz, 1H), 7.11-7.01 (m, 2H), 5.23-5.11 (m, 1H), 4.76 (s, 2H), 3.92-3.47 (m, 4H), 2.87-2.64 (m, 1H), 2.36-2.16 (m, 2H), 1.16-1.01 (m, 6H); MS (ESI(+)) m/e 407 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting (R)—N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yloxy)benzamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, methanol-d4) δ ppm 8.74 (t, J=6.6 Hz, 1H), 8.20-8.14 (m, 1H), 8.01-7.96 (m, 1H), 7.92 (d, J=8.7 Hz, 1H), 7.85 (d, J=8.6 Hz, 1H), 7.82-7.76 (m, 1H), 7.59-7.39 (m, 6H), 7.10 (d, J=8.6 Hz, 1H), 7.00 (d, J=8.6 Hz, 1H), 5.24-5.07 (m, 1H), 4.75 (d, J=12.3 Hz, 2H), 3.99-3.70 (m, 3H), 3.66-3.56 (m, 1H), 2.39-2.19 (m, 2H); MS (ESI(+)) m/e 441 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting (R)—N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yloxy)benzamide for 3-methylbutan-1-amine and (S)-tetrahydrofuran-3-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, methanol-d4) δ ppm 8.75 (d, J=7.0 Hz, 1H), 8.19-8.15 (m, 1H), 8.01-7.97 (m, 1H), 7.93-7.86 (m, 2H), 7.82-7.77 (m, 1H), 7.51-7.45 (m, 1H), 7.10-7.01 (m, 2H), 5.23-5.12 (m, 1H), 4.75 (s, 2H), 4.05-3.92 (m, 1H), 3.94-3.63 (m, 7H), 3.57-3.34 (m, 1H), 2.40-2.29 (m, 1H), 2.27-1.97 (m, 3H); MS (ESI(+)) m/e 435 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting (R)—N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yloxy)benzamide for 3-methylbutan-1-amine and (S)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, methanol-d4) δ ppm 8.75 (d, J=7.0 Hz, 1H), 8.17 (d, J=2.2 Hz, 1H), 7.99 (d, J=2.2 Hz, 1H), 7.94-7.86 (m, 2H), 7.82-7.77 (m, 1H), 7.48 (d, J=7.1 Hz, 1H), 7.10-7.00 (m, 2H), 5.22-5.11 (m, 1H), 4.76 (s, 2H), 3.91-3.49 (m, 4H), 2.70-2.49 (m, 1H), 2.35-2.17 (m, 2H), 1.73-1.59 (m, 1H), 1.50-1.36 (m, 1H), 1.14-1.03 (m, 3H), 0.93-0.86 (m, 3H); MS (ESI(+)) m/e 421 (M+H)+.
- The title compound was prepared as described in Example 1C, substituting 4-phenoxyaniline for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.68 (s, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 7.88 (t, J=0.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.44 (m, 2H), 7.39 (m, 1H), 7.34 (m, 2H), 7.07 (m, 1H), 6.93 (m, 4H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.70 (t, J=6.0 Hz, 1H), 4.34 (d, J=6.0 Hz, 2H); MS (ESI(+)) m/e 359 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 5-bromothiophene-2-carboxylic acid for 4-bromoaniline.
- The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(1-isobutyl-1H-pyrazol-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.11 (t, J=6.0 Hz, 1H), 8.90 (dd, J=7.1, 1.0 Hz, 1H), 8.46 (s, 1H), 8.15 (d, J=0.9 Hz, 1H), 7.81 (s, 1H), 7.75 (d, J=3.9 Hz, 1H), 7.71-7.64 (m, 1H), 7.23 (d, J=3.8 Hz, 1H), 7.16 (dd, J=7.1, 1.8 Hz, 1H), 4.58 (d, J=5.8 Hz, 2H), 3.93 (d, J=7.1 Hz, 2H), 2.20-2.04 (m, 1H), 0.86 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 381 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 2-bromothiazole-5-carboxylic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 4-bromoaniline.
- The title compound was prepared as described in Example 1B, substituting tert-butyl 4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)thiazol-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for N-isopentyl-4-nitrobenzamide.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)thiazol-2-yl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(piperidin-4-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.23 (t, J=6.0 Hz, 1H), 8.49 (d, J=7.0 Hz, 1H), 8.33 (s, 1H), 7.89 (bs, 1H), 7.52 (d, J=1.0 Hz, 1H), 7.40 (bs, 1H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 4.48 (d, J=6.1 Hz, 2H), 4.44 (d, J=13.4 Hz, 1H), 4.02 (d, J=13.1 Hz, 1H), 3.34-3.27 (m, 1H), 3.19 (t, J=11.9 Hz, 1H), 2.95-2.84 (m, 1H), 2.72 (t, J=12.1 Hz, 1H), 2.13-2.02 (m, 2H), 1.68-1.43 (m, 2H), 1.04-0.96 (m, 6H); MS (ESI(+)) m/e 412 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(piperidin-4-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ππμ9.23 (t, J=5.9 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.33 (s, 1H), 7.92-7.87 (m, 1H), 7.53 (d, J=1.2 Hz, 1H), 7.40 (d, J=1.6 Hz, 1H), 6.84 (dd, J=6.9, 1.7 Hz, 1H), 4.51-4.41 (m, 3H), 3.96 (d, J=13.8 Hz, 1H), 3.34-3.24 (m, 1H), 3.16 (t, J=11.7 Hz, 1H), 2.71 (t, J=12.2 Hz, 1H), 2.21 (dd, J=7.0, 2.3 Hz, 2H), 2.10-2.00 (m, 2H), 1.61 (qd, J=12.7, 4.3 Hz, 1H), 1.49 (qd, J=12.5, 4.4 Hz, 1H), 0.90 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 426 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(piperidin-4-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.24 (t, J=5.9 Hz, 1H), 8.49 (d, J=7.0 Hz, 1H), 8.34 (s, 1H), 7.89 (s, 1H), 7.53 (d, J=1.1 Hz, 1H), 7.43 (ddd, J=9.6, 6.8, 3.7 Hz, 6H), 6.84 (dd, J=7.0, 1.6 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 4.48 (d, J=5.9 Hz, 1H), 3.72-3.58 (m, 1H), 3.26-3.13 (m, 1H), 3.06-2.91 (m, 1H), 2.17-1.95 (m, 2H), 1.72-1.62 (m, 2H); MS (ESI(+)) m/e 446 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)benzoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, methanol-d4) δ ppm 8.78-8.72 (m, 1H), 8.40 (s, 1H), 7.90-7.83 (m, 2H), 7.75-7.67 (m, 3H), 7.25 (dd, J=7.0, 1.8 Hz, 1H), 4.75-4.69 (m, 2H), 2.44-2.25 (m, 3H), 1.95-1.76 (m, 2H), 1.78-1.50 (m, 4H), 1.35-1.17 (m, 2H); MS (ESI(+)) m/e 378 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-hydroxy-4-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 5-(4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 2-methylpropanoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.98 (t, J=6.0 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90-7.87 (m, 1H), 7.65 (d, J=3.8 Hz, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 7.00 (d, J=3.8 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 5.76 (s, 1H), 4.46 (d, J=5.9 Hz, 2H), 4.33-4.23 (m, 1H), 3.81-3.71 (m, 1H), 2.99-2.85 (m, 1H), 2.21 (d, J=7.0 Hz, 2H), 2.07-1.91 (m, 1H), 1.86-1.71 (m, 4H), 0.94-0.87 (m, 6H); MS (ESI(+)) m/e 441 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 5-(4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.98 (s, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.88 (s, 1H), 7.65 (d, J=3.8 Hz, 1H), 7.51 (d, J=1.1 Hz, 1H), 7.37 (s, 1H), 7.01 (d, J=3.8 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 5.77 (s, 1H), 4.46 (d, J=5.6 Hz, 2H), 4.33-4.22 (m, 1H), 3.88-3.74 (m, 1H), 2.98-2.82 (m, 2H), 1.82 (s, 4H), 1.05-0.96 (m, 6H); MS (ESI(+)) m/e 427 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 5-(4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 3,3-dimethylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.98 (t, J=5.8 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.91-7.86 (m, 1H), 7.65 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 7.00 (d, J=3.8 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 5.76 (s, 1H), 4.46 (d, J=6.0 Hz, 2H), 4.38-4.28 (m, 1H), 3.89-3.78 (m, 1H), 2.97-2.85 (m, 1H), 2.38-2.13 (m, 3H), 1.86-1.71 (m, 4H), 0.99 (s, 9H); MS (ESI(+)) m/e 455 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 5-(4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.98 (s, 1H), 8.48 (d, J=6.2 Hz, 1H), 7.88 (s, 1H), 7.66 (d, J=3.8 Hz, 1H), 7.53-7.35 (m, 7H), 7.06 (d, J=3.8 Hz, 1H), 6.83 (d, J=7.0 Hz, 1H), 5.83 (s, 1H), 4.46 (d, J=5.9 Hz, 3H), 4.52-4.26 (m, 1H), 1.93 (s, 5H); MS (ESI(+)) m/e 461 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)azetidin-3-yl)benzoic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 3-(4-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)phenyl)azetidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- In a 4 mL vial was mixed 4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide bis(2,2,2-trifluoroacetate) (60 mg, 0.112 mmol) in anhydrous tetrahydrofuran (2 mL) at room temperature. To this mixture was added in portions 60% sodium hydride in mineral oil (22.45 mg, 0.561 mmol). This heterogeneous mixture was stirred 1 hour. To this was added propane-2-sulfonyl chloride (0.015 mL, 0.135 mmol) at and reaction mixture was stirred for 3 hours. The mixture was quenched with water, and product was extracted with 10% methanol/dichloromethane. The organic layers were combined, concentrated and purified by normal phase chromatography to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.07 (m, 1H), 8.47 (d, J=7.0 Hz, 1H), 7.90 (m, 3H), 7.48 (m, 3H), 7.37 (s, 1H), 6.84 (m, 1H), 4.50 (d, J=5.9 Hz, 2H), 4.22 (m, 2H), 3.93 (m, 3H), 3.48 (m, 1H), 1.25 (d, J=5.9 Hz, 6H); MS (ESI(+)) m/e 413 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}azetidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 4-(azetidin-3-yloxy)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.99 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90 (m, 3H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (m, 1H), 6.95 (m, 2H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 5.11 (m, 1H), 4.64 (dd, J=9.5, 6.4 Hz, 1H), 4.49 (d, J=5.8 Hz, 2H), 4.32 (dd, J=10.4, 6.3 Hz, 1H), 4.09 (m, 1H), 3.78 (dd, J=10.6, 3.9 Hz, 1H), 2.48 (m, 1H), 0.98 (t, J=6.7 Hz, 6H); MS (ESI(+)) m/e 393 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 4-(azetidin-3-yloxy)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 3-methylbutan-1-amine and (2S)-2-methylbutyric acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.99 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90 (m, 3H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 6.95 (m, 2H), 6.85 (dd, J=6.9, 1.6 Hz, 1H), 5.11 (dd, J=6.4, 3.5 Hz, 1H), 4.63 (dd, J=9.5, 6.5 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.33 (m, 1H), 4.11 (m, 1H), 3.79 (m, 1H), 2.29 (m, 1H), 1.50 (m, 1H), 1.28 (m, 1H), 0.97 (t, J=6.0 Hz, 3H), 0.82 (m, 3H); MS (ESI(+)) m/e 407 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 4-(azetidin-3-yloxy)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 3-methylbutan-1-amine and cyclopropylacetic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.99 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90 (m, 3H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 6.94 (m, 2H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 5.10 (m, 1H), 4.57 (dd, J=9.5, 6.5 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.33 (dd, J=10.6, 6.5 Hz, 1H), 4.08 (dd, J=9.6, 3.8 Hz, 1H), 3.78 (dd, J=10.6, 3.9 Hz, 1H), 2.03 (d, J=6.8 Hz, 2H), 0.91 (m, 1H), 0.44 (m, 2H), 0.10 (m, 2H); MS (ESI(+)) m/e 405 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 4-(azetidin-3-yloxy)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.99 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90 (m, 3H), 7.66 (m, 2H), 7.59-7.42 (m, 4H), 7.37 (s, 1H), 6.95 (m, 2H), 6.84 (dd, J=6.9, 1.7 Hz, 1H), 5.17 (m, 1H), 4.71 (m, 1H), 4.57 (m, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.33 (m, 1H), 4.02 (m, 1H); MS (ESI(+)) m/e 427 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.11 (t, J=5.9 Hz, 1H), 8.89 (dd, J=7.0, 0.9 Hz, 1H), 8.44 (s, 1H), 7.89-7.83 (m, 2H), 7.67-7.65 (m, 1H), 7.40-7.34 (m, 2H), 7.15 (dd, J=7.0, 1.8 Hz, 1H), 4.62-4.57 (m, 2H), 4.14-4.03 (m, 2H), 2.91-2.67 (m, 3H), 1.82-1.71 (m, 2H), 1.60-1.37 (m, 11H); MS (ESI(+)) m/e 436 (M+H)+.
- The title compound was prepared as described in Example 1C, substituting N-(4-aminophenyl)-2-cyclopentylacetamide for 4-amino-N-isopentylbenzamide and [1,2,4]triazolo[1,5-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.68 (s, 1H), 8.89 (d, J=7.0 Hz, 1H), 8.64 (s, 1H), 8.45 (s, 1H), 7.65 (s, 1H), 7.47-7.41 (m, 2H), 7.34-7.28 (m, 2H), 7.14 (dd, J=7.0, 1.8 Hz, 1H), 6.78 (t, J=6.0 Hz, 1H), 4.42 (d, J=6.0 Hz, 2H), 2.29-2.15 (m, 3H), 1.79-1.68 (m, 2H), 1.66-1.43 (m, 4H), 1.24-1.11 (m, 2H); MS (ESI(+)) m/e 393 (M+H)+.
- The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate for 4-amino-N-isopentylbenzamide and [1,2,4]triazolo[1,5-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.89 (d, J=7.0 Hz, 1H), 8.66 (s, 1H), 8.45 (s, 1H), 7.64 (s, 1H), 7.36-7.30 (m, 2H), 7.14 (dd, J=7.0, 1.8 Hz, 1H), 7.12-7.07 (m, 2H), 6.80 (t, J=6.0 Hz, 1H), 4.43 (d, J=6.0 Hz, 2H), 4.10-4.00 (m, 2H), 2.90-2.63 (m, 2H), 2.66-2.54 (m, 1H), 1.75-1.67 (m, 2H), 1.49-1.35 (s, 11H); MS (ESI(+)) m/e 451 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting piperidine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.18 (t, J=5.9 Hz, 1H), 8.49 (d, J=7.0 Hz, 1H), 7.96 (m, 2H), 7.89 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.47 (m, 2H), 7.40 (s, 1H), 6.86 (dd, J=7.0, 1.7 Hz, 1H), 4.52 (d, J=5.9 Hz, 2H), 3.59 (m, 2H), 3.24 (m, 2H), 1.66-1.38 (m, 6H); MS (ESI(+)) m/e 363 (M+H)+.
- The title compound was prepared as described in Example 557C, substituting ethane sulfonyl chloride for propane-2-sulfonyl chloride. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.10 (t, J=6.0 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 7.93 (m, 2H), 7.88 (m, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.49 (m, 2H), 7.39 (s, 1H), 6.86 (dd, J=7.0, 1.6 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 4.23 (m, 2H), 3.95 (m, 3H), 3.19 (q, J=7.3 Hz, 2H), 1.25 (t, J=7.3 Hz, 3H); MS (ESI(+)) m/e 399 (M+H)+.
- The title compound was prepared as described in Example 557C, substituting cyclopropane sulfonyl chloride for propane-2-sulfonyl chloride. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.10 (t, J=6.0 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 7.93 (m, 2H), 7.88 (m, 1H), 7.52 (d, J=1.1 Hz, 1H), 7.50 (m, 2H), 7.39 (s, 1H), 6.86 (dd, J=7.0, 1.6 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 4.26 (t, J=7.7 Hz, 2H), 3.99 (m, 3H), 2.85 (m, 1H), 1.06 (m, 2H), 0.97 (m, 2H); MS (ESI(+)) m/e 411 (M+H)+.
- The title compound was prepared as described in Example 557C, substituting benzene sulfonyl chloride for propane-2-sulfonyl chloride. —1H NMR (500 MHz, DMSO-d6) δ ppm 9.04 (t, J=5.9 Hz, 1H), 8.47 (m, 1H), 7.92-7.82 (m, 4H), 7.75 (m, 4H), 7.51 (d, J=1.2 Hz, 1H), 7.36 (s, 1H), 7.97 (m, 2H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 4.47 (d, J=5.9 Hz, 2H), 4.16 (m, 2H), 3.79 (m, 1H), 3.67 (m, 2H); MS (ESI(+)) m/e 447 (M+H)+.
- To a suspension N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide (0.103 g, 0.249 mmol) in dichloromethane (2 ml) was added N-methylmorpholine (0.110 ml, 0.997 mmol) followed by isopropylchloroformate (0.374 ml, 0.374 mmol). A second portion of isopropylchloroformate (0.4 ml) was added and after 1 hour the mixture was directly purified by normal phase chromatography to give the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.05 (t, J=6.0 Hz, 1H), 8.51 (d, J=7.0 Hz, 1H), 7.92 (s, 1H), 7.68 (d, J=3.8 Hz, 1H), 7.56 (d, J=1.2 Hz, 1H), 7.40 (d, J=1.4 Hz, 1H), 6.96 (d, J=3.8 Hz, 1H), 6.88 (dd, J=7.0, 1.7 Hz, 1H), 4.78 (hept, J=6.2 Hz, 1H), 4.47 (d, J=5.9 Hz, 2H), 4.05 (d, J=12.9 Hz, 2H), 3.10-2.97 (m, 1H), 2.98-2.81 (m, 2H), 2.01-1.88 (m, 2H), 1.57-1.38 (m, 2H), 1.19 (d, J=6.2 Hz, 6H); MS (ESI(+)) m/e 427 (M+H)+.
- The title compound was prepared as described in Example 570, substituting isobutyl carbonochloridate for isopropyl carbonochloridate. 1H NMR (300 MHz, DMSO-d6) δ 8.99 (t, J=6.0 Hz, 1H), 8.48 (dd, J=7.0, 0.9 Hz, 1H), 7.88 (t, J=1.0 Hz, 1H), 7.67 (d, J=3.9 Hz, 1H), 7.51 (d, J=1.1 Hz, 1H), 7.37 (s, 1H), 6.96 (d, J=3.1 Hz, 1H), 6.82 (dd, J=7.0, 1.8 Hz, 1H), 4.46 (d, J=5.8 Hz, 2H), 4.06 (d, J=13.3 Hz, 2H), 3.79 (d, J=6.6 Hz, 2H), 3.13-2.97 (m, 1H), 2.97-2.80 (m, 2H), 2.03-1.77 (m, 3H), 1.48 (qd, J=12.5, 4.2 Hz, 2H), 0.89 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 441 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting 3,3,3-trifluoropropanoyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.00 (t, J=6.0 Hz, 1H), 8.48 (dd, J=6.9, 1.0 Hz, 1H), 7.88 (t, J=1.0 Hz, 1H), 7.67 (d, J=3.8 Hz, 1H), 7.51 (d, J=1.3 Hz, 1H), 7.40-7.33 (m, 1H), 6.96 (dd, J=3.7, 0.8 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.46 (d, J=6.3 Hz, 2H), 3.90 (d, J=13.8 Hz, 1H), 3.66 (q, J=11.0 Hz, 2H), 3.23-3.04 (m, 2H), 2.71 (td, J=12.8, 2.6 Hz, 1H), 2.07-1.88 (m, 2H), 1.71-1.31 (m, 2H); MS (ESI(+)) m/e 451 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting 2-methylpropane-1-sulfonyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.01 (t, J=6.0 Hz, 1H), 8.48 (d, J=6.9 Hz, 1H), 7.89 (s, 1H), 7.68 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.1 Hz, 1H), 7.38 (s, 1H), 6.98 (d, J=3.8 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.46 (d, J=6.0 Hz, 2H), 3.71-3.59 (m, 2H), 2.99 (tt, J=11.6, 3.6 Hz, 1H), 2.94-2.82 (m, 4H), 2.20-2.08 (m, 1H), 2.08-1.97 (m, 2H), 1.62 (qd, J=12.6, 4.1 Hz, 2H), 1.04 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 461 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 4,4,4-trifluorobutanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.00 (t, J=6.0 Hz, 1H), 8.48 (d, J=6.8 Hz, 1H), 7.89 (s, 1H), 7.68 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.41-7.34 (m, 1H), 6.96 (d, J=3.8 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.54-4.38 (m, 3H), 4.02-3.88 (m, 1H), 3.12 (tdt, J=11.3, 7.9, 3.1 Hz, 2H), 2.76-2.41 (m, 5H), 2.06-1.88 (m, 2H), 1.58 (qd, J=12.3, 4.0 Hz, 1H), 1.42 (qd, J=12.5, 4.2 Hz, 1H); MS (ESI(+)) m/e 465 (M+H)+.
- A solution of N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-isobutyrylpiperidin-4-yl)benzamide (0.025 g, 0.062 mmol) in chloroform (1.030 ml) was treated with N-chlorosuccinimide (9.49 mg, 0.071 mmol) and the reaction was stirred at ambient temperature for 16 hours. The reaction was concentrated under a stream of warm nitrogen. The residue was purified by normal phase chromatography to give the title compound. 1H NMR (500 MHz, methanol-d4) δ ppm 8.67 (d, J=7.0 Hz, 1H), 8.11 (s, 1H), 7.89-7.83 (m, 2H), 7.81 (s, 1H), 7.57 (dd, J=7.1, 1.5 Hz, 1H), 7.43-7.37 (m, 2H), 4.80-4.75 (m, 2H), 4.75-4.67 (m, 1H), 4.25-4.16 (m, 1H), 3.28-3.18 (m, 1H), 3.07-2.88 (m, 2H), 2.79-2.66 (m, 1H), 2.02-1.85 (m, 2H), 1.75-1.53 (m, 2H), 1.17-1.08 (m, 6H); MS (ESI(+)) m/e 439 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-((4-methyltetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.02 (t, J=6.0 Hz, 1H), 8.49 (dd, J=7.1, 1.0 Hz, 1H), 8.13 (s, 1H), 7.89 (t, J=1.0 Hz, 1H), 7.81 (s, 1H), 7.74 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.3 Hz, 1H), 7.43-7.36 (m, 1H), 7.23 (d, J=3.8 Hz, 1H), 6.85 (dd, J=7.1, 1.7 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 4.04 (s, 2H), 3.68 (dt, J=11.8, 4.6 Hz, 2H), 3.52 (ddd, J=11.9, 9.1, 3.0 Hz, 2H), 1.51 (ddd, J=13.4, 9.2, 4.2 Hz, 2H), 1.24 (dt, J=13.4, 4.0 Hz, 2H), 0.96 (s, 3H); MS (ESI(+)) m/e 436 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 2,2-dimethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ 9.05 (t, J=6.0 Hz, 1H), 8.49 (dd, J=6.8, 1.0 Hz, 1H), 8.19 (d, J=0.7 Hz, 1H), 7.92 (s, 1H), 7.90-7.88 (m, 1H), 7.76 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.1 Hz, 1H), 7.43-7.36 (m, 1H), 7.27 (d, J=3.8 Hz, 1H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 4.48 (d, J=5.7 Hz, 2H), 4.35 (s, 2H), 1.35 (s, 6H); MS (ESI(+)) m/e 405 (M+H)+.
- 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide
- 2-Bromo-3-chlorothiophene (10.7 g, 51.5 mmol) was dissolved in dichloromethane (73.5 ml). The flask was equipped with a desiccant filled drying tube and the solution was chilled in an ice bath. Acetyl chloride (6.06 g, 77 mmol) was added followed by addition of aluminum trichloride (8.24 g, 61.8 mmol) over about 2 minutes (reaction bubbled vigorously as aluminum trichloride was added). The reaction mixture was stirred overnight, allowing to warm to room temperature, and then added cautiously and with stirring to a 1-L beaker containing ˜200 mL sat sodium bicarbonate. The mixture was stirred for 30 minutes and diluted with dichloromethane (A100 mL). The layers were separated and the organic layer was washed with aqueous saturated sodium bicarbonate, water, and brine. The combined organic layers were dried with sodium sulfate, filtered, and concentrated to give a crude solid. This material was recrystallized from hot hexanes to give the title compound.
- Sodium hydroxide (50% in water) (5.82 ml, 110 mmol) was added to water (15 ml), and the mixture was chilled to 0° C. Bromine solution (1.669 ml, 32.6 mmol) was added, followed by dropwise addition of a solution of 1-(5-bromo-4-chlorothiophen-2-yl)ethanone (2.4 g, 10.02 mmol) in dioxane (18 ml). The mixture was stirred for 1.5 hours at room temperature, washed with dichloromethane, and then the aqueous phase was adjusted to pH 1 using 4N aqueous HCl. The precipitated solid was collected by filtration to give the title compound.
- The title compound was prepared as described in Example 51A, substituting 5-bromo-4-chlorothiophene-2-carboxylic acid for 4-bromoaniline.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-chloro-5-(1-isobutyl-1H-pyrazol-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.17 (t, J=5.9 Hz, 1H), 8.50 (d, J=7.0 Hz, 1H), 8.31 (s, 1H), 7.93-7.88 (m, 2H), 7.83 (s, 1H), 7.53 (d, J=1.1 Hz, 1H), 7.42 (s, 1H), 6.85 (dd, J=7.0, 1.6 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 3.98 (d, J=7.2 Hz, 2H), 2.20-2.08 (m, 1H), 0.86 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 414 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and (R)-4-chloro-5-(1-((tetrahydrofuran-3-yl)methyl)-1H-pyrazol-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.17 (t, J=6.0 Hz, 1H), 8.50 (d, J=7.0 Hz, 1H), 8.28 (s, 1H), 7.93-7.88 (m, 2H), 7.83 (s, 1H), 7.53 (d, J=1.2 Hz, 1H), 7.42 (s, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.28-4.15 (m, 3H), 3.78-3.72 (m, 1H), 3.67-3.61 (m, 1H), 1.98-1.90 (m, 1H), 1.84-1.70 (m, 2H), 1.65-1.57 (m, 1H); MS (ESI(+)) m/e 442 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 5-bromothiophene-2-carboxylic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 51A, substituting 2-methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-ol for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-bromothiophene-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (t, J=5.9 Hz, 1H), 8.88 (s, 1H), 8.48 (s, 1H), 8.04 (d, J=0.5 Hz, 1H), 7.84 (dd, J=9.2, 0.7 Hz, 1H), 7.79 (d, J=0.5 Hz, 1H), 7.71 (d, J=3.9 Hz, 1H), 7.66 (dd, J=9.2, 1.7 Hz, 1H), 7.22 (d, J=3.9 Hz, 1H), 4.72 (s, 1H), 4.54 (d, J=5.8 Hz, 2H), 4.03 (s, 2H), 1.08 (s, 6H); MS (ESI(+)) m/e 397 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-((4-methyltetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-bromothiophene-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (t, J=5.9 Hz, 1H), 8.88 (s, 1H), 8.48 (s, 1H), 8.04 (d, J=0.5 Hz, 1H), 7.84 (dd, J=9.2, 0.7 Hz, 1H), 7.79 (d, J=0.5 Hz, 1H), 7.71 (d, J=3.9 Hz, 1H), 7.66 (dd, J=9.2, 1.7 Hz, 1H), 7.22 (d, J=3.9 Hz, 1H), 4.72 (s, 1H), 4.54 (d, J=5.8 Hz, 2H), 4.03 (s, 2H), 1.08 (s, 6H); MS (ESI(+)) m/e 437 (M+H)+.
- The title compound was prepared as described in Example 557C, substituting methane sulfonyl chloride for propane-2-sulfonyl chloride. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.11 (t, J=6.0 Hz, 1H), 8.49 (m, 1H), 7.91 (m, 2H), 7.88 (m, 1H), 7.52 (m, 2H), 7.49 (m, 1H), 7.39 (s, 1H), 6.86 (dd, J=7.0, 1.7 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 4.23 (m, 2H), 3.95 (m, 3H), 3.08 (s, 3H); MS (ESI(+)) m/e 385 (M+H)+.
- The title compound was prepared as described in Example 557C, substituting methane sulfonyl chloride for propane-2-sulfonyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yl)benzamide for 4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide. H NMR (400 MHz, DMSO-d6) δ ppm 9.07 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.88 (m, 3H), 7.52 (d, J=1.2 Hz, 1H), 7.45 (m, 2H), 7.38 (m, 1H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 3.73 (dd, J=9.6, 7.5 Hz, 1H), 3.47 (m, 2H), 3.35 (m, 1H), 3.19 (t, J=9.6 Hz, 1H), 2.97 (s, 3H), 2.31 (m, 1H), 2.02 (m, 1H); MS (ESI(+)) m/e 399 (M+H)+.
- The title compound was prepared as described in Example 557C, substituting ethane sulfonyl chloride for propane-2-sulfonyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yl)benzamide for 4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide. H NMR (400 MHz, DMSO-d6) δ ppm 9.07 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.88 (m, 3H), 7.52 (d, J=1.2 Hz, 1H), 7.45 (m, 2H), 7.38 (s, 1H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 4.50 (d, J=5.9 Hz, 2H), 3.75 (dd, J=9.5, 7.5 Hz, 1H), 3.50 (m, 2H), 3.38 (m, 1H), 3.26-3.12 (m, 3H), 2.32 (m, 1H), 2.03 (m, 1H), 1.24 (t, J=7.3 Hz, 3H); MS (ESI(+)) m/e 413 (M+H)+.
- The title compound was prepared as described in Example 557C, substituting cyclopropane sulfonyl chloride for propane-2-sulfonyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yl)benzamide for 4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.07 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.88 (m, 3H), 7.51 (d, J=1.2 Hz, 1H), 7.45 (m, 2H), 7.38 (m, 1H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 4.50 (d, J=5.9 Hz, 2H), 3.79 (dd, J=9.7, 7.5 Hz, 1H), 3.53 (m, 2H), 3.43 (m, 1H), 3.23 (m, 1H), 2.78 (m, 1H), 2.34 (m, 1H), 2.01 (m, 1H), 0.98 (m, 4H); MS (ESI(+)) m/e 425 (M+H)+.
- The title compound was prepared as described in Example 557C, substituting benzene sulfonyl chloride for propane-2-sulfonyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yl)benzamide for 4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.04 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.87 (m, 3H), 7.81 (m, 2H), 7.74 (m, 1H), 7.66 (m, 2H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (m, 1H), 7.25 (m, 2H), 6.84 (dd, J=6.9, 1.7 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 3.72 (dd, J=9.8, 7.5 Hz, 1H), 3.46 (m, 1H), 3.26 (m, 2H), 3.11 (m, 1H), 2.17 (m, 1H), 1.78 (m, 1H); MS (ESI(+)) m/e 461 (M+H)+.
- The title compound was prepared as described in Example 557C, substituting propane-2-sulfonyl chloride for propane-2-sulfonyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yl)benzamide for 4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide. 1H NMR (501 MHz, DMSO-d6) δ ppm 9.04 (t, J=6.0 Hz, 1H), 8.47 (d, J=6.9 Hz, 1H), 7.87 (m, 3H), 7.50 (d, J=1.2 Hz, 1H), 7.43 (m, 2H), 7.37 (s, 1H), 6.84 (dd, J=7.0, 1.6 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 3.77 (m, 1H), 3.52 (m, 2H), 3.42 (m, 2H), 3.25 (m, 1H), 2.30 (m, 1H), 2.04 (m, 1H), 1.25 (dd, J=6.8, 1.4 Hz, 6H); MS (ESI(+)) m/e 427 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-(2-methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 4-bromoaniline. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.66 (s, 1H), 8.50 (d, J=7.0 Hz, 1H), 8.01 (s, 1H), 7.90 (s, 1H), 7.77 (s, 1H), 7.54 (s, 1H), 7.40 (m, 5H), 6.87 (dd, J=7.0, 1.6 Hz, 1H), 6.71 (t, J=6.0 Hz, 1H), 4.34 (d, J=6.0 Hz, 2H), 4.23 (t, J=5.3 Hz, 2H), 3.69 (t, J=5.3 Hz, 2H), 3.23 (s, 3H); MS (ESI(+)) m/e 391 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-(tetrahydrofuran-2-ylmethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 4-bromoaniline. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.64 (s, 1H), 8.47 (d, J=7.0 Hz, 1H), 8.00 (s, 1H), 7.87 (s, 1H), 7.77 (s, 1H), 7.50 (d, J=1.2 Hz, 1H), 7.40 (m, 5H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.70 (t, J=6.0 Hz, 1H), 4.33 (d, J=6.0 Hz, 2H), 4.13 (m, 3H), 3.74 (m, 1H), 3.62 (m, 1H), 1.91 (m, 1H), 1.76 (m, 2H), 1.60 (m, 1H); MS (ESI(+)) m/e 417 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-(tetrahydro-2H-pyran-4-ylmethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 4-bromoaniline. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.64 (s, 1H), 8.47 (d, J=7.0 Hz, 1H), 8.02 (s, 1H), 7.87 (s, 1H), 7.77 (d, J=0.8 Hz, 1H), 7.50 (d, J=1.2 Hz, 1H), 7.40 (m, 5H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.70 (t, J=6.0 Hz, 1H), 4.32 (d, J=5.9 Hz, 2H), 3.98 (d, J=7.1 Hz, 2H), 3.81 (m, 2H), 3.23 (m, 2H), 2.05 (m, 1H), 1.40 (m, 2H), 1.23 (m, 2H); MS (ESI(+)) m/e 431 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-((1,4-dioxan-2-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-bromothiophene-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (t, J=5.9 Hz, 1H), 8.90-8.85 (m, 1H), 8.48 (s, 1H), 8.12 (s, 1H), 7.84 (dd, J=9.2, 0.8 Hz, 1H), 7.82 (d, J=0.6 Hz, 1H), 7.71 (d, J=3.9 Hz, 1H), 7.66 (dd, J=9.2, 1.7 Hz, 1H), 7.22 (d, J=3.9 Hz, 1H), 4.54 (d, J=5.8 Hz, 2H), 4.20-4.12 (m, 2H), 3.95-3.83 (m, 1H), 3.74 (dd, J=11.4, 2.5 Hz, 2H), 3.68-3.60 (m, 1H), 3.59-3.39 (m, 2H), 3.29-3.21 (m, 1H); MS (ESI(+)) m/e 425 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting 2-fluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.00 (t, J=6.0 Hz, 1H), 8.48 (dd, J=7.0, 0.8 Hz, 1H), 7.91-7.85 (m, 1H), 7.67 (d, J=3.8 Hz, 1H), 7.55-7.35 (m, 4H), 7.34-7.25 (m, 2H), 6.98 (dd, J=3.8, 0.5 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.60 (d, J=13.2 Hz, 1H), 4.46 (d, J=5.9 Hz, 2H), 3.45 (d, J=12.7 Hz, 1H), 3.28-3.08 (m, 2H), 2.93 (td, J=12.8, 2.5 Hz, 1H), 2.00 (dd, J=43.2, 12.5 Hz, 2H), 1.68-1.39 (m, 2H); MS (ESI(+)) m/e 463 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, methanol-d4) δ ppm 9.00-8.96 (m, 1H), 8.51-8.46 (m, 1H), 8.04-8.00 (m, 1H), 7.89-7.81 (m, 2H), 7.81-7.77 (m, 1H), 7.39-7.32 (m, 2H), 4.68 (s, 2H), 4.27-4.16 (m, 2H), 2.97-2.70 (m, 3H), 1.92-1.78 (m, 2H), 1.71-1.50 (m, 2H), 1.48 (s, 9H); MS (ESI(+)) m/e 436 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)benzoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, methanol-d4) δ ppm 9.19 (d, J=0.9 Hz, 1H), 8.65 (d, J=1.2 Hz, 1H), 8.20 (d, J=1.1 Hz, 1H), 8.03 (d, J=1.5 Hz, 1H), 7.90-7.83 (m, 2H), 7.73-7.66 (m, 2H), 4.74 (s, 2H), 2.44-2.22 (m, 3H), 1.92-1.76 (m, 2H), 1.76-1.49 (m, 4H), 1.35-1.14 (m, 2H); MS (ESI(+)) m/e 378 (M+H)+.
- The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyrazin-6-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1H NMR (500 MHz, methanol-d4) δ ppm 8.99-8.95 (m, 1H), 8.48-8.44 (m, 1H), 8.02 (s, 1H), 7.81-7.77 (m, 1H), 7.33-7.26 (m, 2H), 7.15-7.09 (m, 2H), 4.49 (s, 2H), 4.22-4.14 (m, 2H), 2.92-2.73 (m, 2H), 2.74-2.58 (m, 1H), 1.82-1.74 (m, 2H), 1.61-1.41 (m, 11H); MS (ESI(+)) m/e 451 (M+H)+.
- The title compound was prepared as described in Example 1C, substituting N-(4-aminophenyl)-2-cyclopentylacetamide for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyrazin-6-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1H NMR (500 MHz, methanol-d4) δ ppm 9.17-9.13 (m, 1H), 8.60 (s, 1H), 8.18 (s, 1H), 7.99 (d, J=1.5 Hz, 1H), 7.46-7.40 (m, 2H), 7.35-7.29 (m, 2H), 4.56 (bs, 2H), 2.37-2.23 (m, 3H), 1.90-1.77 (m, 2H), 1.77-1.49 (m, 4H), 1.34-1.17 (m, 2H); MS (ESI(+)) m/e 393 (M+H)+.
- A solution of N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide (0.05 g, 0.150 mmol) in tetrahydrofuran (1.246 ml) was treated with sodium hydride (0.018 g, 0.449 mmol) in 3 portions. The reaction was stirred at ambient temperature for 45 minutes and became a partially homogeneous solution. Benzenesulfonyl chloride (0.021 ml, 0.164 mmol) was added and the mixture was stirred for 16 hours. The reaction was treated with 0.1 mL water and was concentrated under a stream of nitrogen. Reverse-phase chromatography provided the title compound. 1H NMR (500 MHz, methanol-d4) δ ppm 8.73 (dd, J=7.0, 0.9 Hz, 1H), 8.15 (dd, J=2.2, 0.8 Hz, 1H), 7.97 (d, J=2.2 Hz, 1H), 7.89-7.75 (m, 5H), 7.73-7.59 (m, 3H), 7.46 (dd, J=7.0, 1.6 Hz, 1H), 7.37-7.31 (m, 2H), 4.75 (s, 2H), 3.96-3.88 (m, 2H), 2.67-2.52 (m, 1H), 2.48-2.37 (m, 2H), 1.95-1.72 (m, 4H); MS (ESI(+)) m/e 475 (M+H)+.
- The title compound was prepared as described in Example 682, substituting propane-2-sulfonyl chloride for benzenesulfonyl chloride. 1H NMR (500 MHz, methanol-d4) δ ppm 8.75 (d, J=7.0 Hz, 1H), 8.17 (d, J=2.2 Hz, 1H), 7.99 (d, J=2.2 Hz, 1H), 7.89-7.83 (m, 2H), 7.80 (s, 1H), 7.49 (dd, J=7.0, 1.6 Hz, 1H), 7.43-7.37 (m, 2H), 4.77 (s, 2H), 3.95-3.87 (m, 2H), 3.38-3.29 (m, 1H), 3.12-3.00 (m, 2H), 2.89-2.75 (m, 1H), 1.95-1.86 (m, 2H), 1.82-1.68 (m, 2H), 1.34 (d, J=6.8 Hz, 6H); MS (ESI(+)) m/e 417 (M+H)+.
- The title compound was prepared as described in Example 682, substituting cyclopropanesulfonyl chloride for benzenesulfonyl chloride. 1H NMR (500 MHz, methanol-d4) δ ppm 8.75 (dd, J=7.0, 0.9 Hz, 1H), 8.19-8.15 (m, 1H), 7.98 (d, J=2.2 Hz, 1H), 7.90-7.84 (m, 2H), 7.80 (s, 1H), 7.48 (dd, J=7.0, 1.6 Hz, 1H), 7.45-7.38 (m, 2H), 4.77 (s, 2H), 3.92-3.84 (m, 2H), 3.07-2.96 (m, 2H), 2.86-2.73 (m, 1H), 2.57-2.46 (m, 1H), 2.00-1.91 (m, 2H), 1.88-1.73 (m, 2H), 1.13-0.99 (m, 4H); MS (ESI(+)) m/e 439 (M+H)+.
- 5-Formylthiophene-2-carboxylic acid (5.3 g, 33.9 mmol) was taken up in tetrahydrofuran (100 ml) and boc-anhydride (16.30 g, 74.7 mmol) was added, followed by N,N-dimethylaminopyridine (0.829 g, 6.79 mmol). The mixture was stirred overnight at room temperature, during which time the reaction became a dark, purplish color. It was diluted with sat sodium bicarbonate and extracted with ether. The organic layers were dried sodium sulfate, concentrated then purified by normal phase chromatography to give the title compound.
- tert-Butyl 5-formylthiophene-2-carboxylate (2 g, 9.42 mmol) and (S)-2-methylpropane-2-sulfinamide (1.370 g, 11.31 mmol) were dissolved in dichloromethane (100 ml). The mixture was chilled in an ice bath to which was added tetraethoxytitanium (8.7 ml, 41.5 mmol). The mixture was allowed to warm to room temperature overnight with stirring.
- The mixture was poured into a large Erlenmeyer flask with 200 mL dichloromethane and was diluted with 18 mL H2O. After vigorous stirring for 30 minutes the suspension was filtered through diatomaceous earth and the filtrate was concentrated. Purification using normal phase chromatography provided the title compound.
- (S,E)-tert-Butyl 5-((tert-butylsulfinylimino)methyl)thiophene-2-carboxylate (1 g, 3.17 mmol) was dissolved in dichloromethane (15.85 ml) and chilled to −45° C. in an acetone bath to which dry ice had been added to achieve the desired temperature. Isobutylmagnesium bromide (2.0M in diethyl ether; 3.17 ml, 6.34 mmol) was added dropwise over −5 minutes. The mixture was stirred for 4 hours keeping the temperature between −40° C. and −50° C. by periodic addition of dry ice and then warmed to room temperature overnight. The mixture was quenched with saturated ammonium chloride (exothermic, bubbling) and extracted with dichloromethane (three times; considerable emulsion formed). The organic extracts were dried with sodium sulfate, filtered, concentrated and chromatographed to provide both tert-butyl 5-((R)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate and tert-butyl 5-((S)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate as separate compounds.
- The title compound was prepared as described in Example 324C, substituting tert-butyl 5-((R)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate for tert-butyl 5-((R)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate.
- The title compound was prepared as described in Example 1A, substituting (R)-tert-butyl 5-(1-amino-3-methylbutyl)thiophene-2-carboxylate for 3-methylbutan-1-amine and cyclopropanecarboxylic acid for 4-nitrobenzoic acid followed by acidic deprotection as described in Example 28A, substituting (R)-tert-butyl 5-(1-(cyclopropanecarboxamido)-3-methylbutyl)thiophene-2-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and (R)-5-(1-(cyclopropanecarboxamido)-3-methylbutyl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.00 (t, J=6.0 Hz, 1H), 8.55 (d, J=8.4 Hz, 1H), 8.48 (d, J=7.4 Hz, 1H), 7.88 (d, J=1.1 Hz, 1H), 7.64 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 6.98 (d, J=3.8 Hz, 1H), 6.82 (dd, J=7.0, 1.7 Hz, 1H), 5.11 (td, J=8.8, 5.0 Hz, 1H), 4.46 (d, J=5.9 Hz, 2H), 1.80-1.52 (m, 4H), 0.95-0.83 (m, 6H), 0.75-0.59 (m, 4H); MS (ESI(+)) m/e 411 (M+H)+.
- The title compound was described as in Example 685, substituting 2-(tetrahydrofuran-3-yl)acetic acid for cyclopropanecarboxylic acid in Example 685E. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.00 (t, J=6.0 Hz, 1H), 8.48 (d, J=7.0 Hz, 1H), 8.39 (d, J=8.5 Hz, 1H), 7.88 (s, 1H), 7.64 (d, J=3.7 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 6.97 (d, J=3.8 Hz, 1H), 6.82 (dd, J=7.0, 1.7 Hz, 1H), 5.16-5.05 (m, 1H), 4.45 (d, J=5.9 Hz, 2H), 3.76-3.51 (m, 3H), 3.29-3.21 (m, 1H), 2.29-2.16 (m, 3H), 2.02-1.86 (m, 1H), 1.78-1.40 (m, 4H), 0.99-0.77 (m, 6H); MS (ESI(+)) m/e 455 (M+H)+.
- The title compound was described as in Example 685, substituting butyl 5-((S)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate for tert-butyl 5-((R)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate in Example 685D. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.04-8.96 (m, 1H), 8.55 (d, J=8.4 Hz, 1H), 8.48 (dd, J=7.0, 0.9 Hz, 1H), 7.88 (s, 1H), 7.64 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.1 Hz, 1H), 7.37 (s, 1H), 6.98 (d, J=3.8 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 5.17-5.05 (m, 1H), 4.46 (d, J=5.9 Hz, 2H), 1.77-1.44 (m, 4H), 1.01-0.77 (m, 6H), 0.66 (d, J=7.2 Hz, 4H); MS (ESI(+)) m/e 411 (M+H)+.
- Ethyl 3-ethoxyacrylate (1.50 g, 10.38 mml) was dissolved in dioxane/water and chilled to −10° C. N-Bromosuccinimide (2.03 g, 11.42 mmol) was added and the mixture was stirred 1 hour at room temperature. tert-Butyl 4-carbamothioylpiperidine-1-carboxylate (2.54 g, 10.38 mmol) was added and the mixture was heated at 100° C. for 1 hour. The reaction mixture was poured into 25 mL saturated ammonium hydroxide and extracted with dichloromethane. The combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated. Normal phase chromatography provided the title compound.
- Ethyl 2-(piperidin-4-yl)thiazole-5-carboxylate (100 mg, 0.416 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (21 mg, 0.033 mmol), bis(dibenzylideneacetone)palladium(0) (15 mg, 0.017 mmol) and cesium carbonate (678 mg, 2.081 mmol) were placed in a pressure tube capped with a septum and degassed with nitrogen by passing a stream through the vessel for 30 minutes. Separately, bromobenzene (68.6 mg, 0.437 mmol) was dissolved in toluene (2 ml) and the solution was degassed by bubbling nitrogen for 30 minutes. The bromobenzene solution was added to the solid mixture and the sealed tube was heated to 100° C. overnight. The mixture was partitioned between dichloromathane and water and the combined organic layers were concentrated and purified by normal phase chromatography to give the title compound.
- A solution of ethyl 2-(1-phenylpiperidin-4-yl)thiazole-5-carboxylate (31 mg, 0.098 mmol) in 1 ml of 1:1 tetrahydrofuran/methanol was treated with 1M aqueous LiOH (0.11 ml, 0.11 mol) and stirred at 65° C. for 3 hours. The mixture was taken to dryness and used directly in the next step.
- Lithium 2-(1-phenylpiperidin-4-yl)thiazole-5-carboxylate (28.8 mg, 0.098 mmol), imidazo[1,2-a]pyridin-7-ylmethanamine (17.31 mg, 0.118 mmol), 4-methylmorpholine (49.6 mg, 0.490 mmol) and 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (55.9 mg, 0.147 mmol) were combined in a vial with dichloromethane (2.5 ml) and the reaction was stirred overnight. The mixture was partitioned between dichloromethane and saturated sodium bicarbonate. The organic layers were dried with sodium sulfate, filtered, and concentrated. Trituration of the crude material with dichloromethane provided the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.21 (t, J=5.9 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 8.34 (s, 1H), 7.91-7.88 (m, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.43-7.38 (m, 1H), 7.26-7.16 (m, 2H), 7.01-6.93 (m, 2H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.81-6.72 (m, 1H), 4.48 (d, J=5.9 Hz, 2H), 3.81-3.73 (m, 2H), 3.24-3.01 (m, 1H), 2.90-2.78 (m, 2H), 2.19-2.09 (m, 2H), 1.90-1.73 (m, 2H); MS (ESI(+)) m/e 418 (M+H)+.
- The title compound was prepared as described in Example 688, substituting 2-bromopyridine for bromobenzene in Example 688B. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.21 (t, J=5.9 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.33 (s, 1H), 8.13-8.09 (m, 1H), 7.89 (s, 1H), 7.55-7.48 (m, 2H), 7.40 (s, 1H), 6.86 (d, J=8.7 Hz, 1H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.61 (dd, J=6.9, 5.1 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 4.40-4.32 (m, 2H), 3.03-2.92 (m, 2H), 2.14-2.05 (m, 2H), 1.68 (qd, J=12.5, 3.9 Hz, 2H); MS (ESI(+)) m/e 419 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-((4-fluorotetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (t, J=6.0 Hz, 1H), 8.49 (d, J=7.1 Hz, 1H), 8.11 (s, 1H), 7.89 (s, 1H), 7.85 (s, 1H), 7.75 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.26 (d, J=3.9 Hz, 1H), 6.85 (dd, J=7.0, 1.6 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 4.42 (d, J=21.4 Hz, 2H), 3.74 (ddd, J=11.4, 4.6, 2.9 Hz, 2H), 3.51 (td, J=11.3, 2.0 Hz, 2H), 1.92-1.64 (m, 2H), 1.55 (t, J=11.8 Hz, 2H); MS (ESI(+)) m/e 440 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-bromofuran-2-carboxylic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 51A, substituting 1-((4-methyltetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and bromide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.89 (t, J=6.1 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 8.13 (d, J=0.5 Hz, 1H), 7.91-7.86 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.17 (d, J=3.6 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.67 (d, J=3.5 Hz, 1H), 4.49 (d, J=6.0 Hz, 2H), 4.07 (s, 2H), 3.68 (dt, J=11.5, 4.5 Hz, 2H), 3.51 (ddd, J=11.9, 9.3, 3.0 Hz, 2H), 1.51 (ddd, J=13.4, 9.2, 4.2 Hz, 2H), 1.33-1.15 (m, 2H), 0.96 (s, 3H); MS (ESI(+)) m/e 420 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline.
- The title compound was prepared as described in Example 1B, substituting tert-butyl 4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)furan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for N-isopentyl-4-nitrobenzamide.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)furan-2-yl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and 2-fluorobenzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.85 (t, J=6.1 Hz, 1H), 8.47 (dd, J=7.0, 0.8 Hz, 1H), 7.92-7.83 (m, 1H), 7.55-7.45 (m, 2H), 7.41 (td, J=7.5, 1.5 Hz, 1H), 7.37 (s, 1H), 7.34-7.25 (m, 2H), 7.06 (d, J=3.4 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 6.33 (dd, J=3.5, 0.7 Hz, 1H), 4.53 (d, J=13.4 Hz, 1H), 4.44 (d, J=6.0 Hz, 2H), 3.44 (d, J=13.0 Hz, 1H), 3.19 (t, J=12.8 Hz, 1H), 3.11-2.90 (m, 2H), 2.09 (d, J=11.0 Hz, 1H), 1.94 (d, J=11.9 Hz, 1H), 1.73-1.42 (m, 2H); MS (ESI(+)) m/e 447 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.84 (t, J=6.1 Hz, 1H), 8.47 (dd, J=7.0, 0.8 Hz, 1H), 7.94-7.82 (m, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.42-7.33 (m, 1H), 7.05 (d, J=3.4 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 6.31 (dd, J=3.4, 0.6 Hz, 1H), 4.44 (d, J=6.0 Hz, 3H), 4.06-3.90 (m, 1H), 3.21-3.07 (m, 1H), 3.07-2.77 (m, 2H), 2.77-2.59 (m, 1H), 2.06-1.90 (m, 2H), 1.61-1.37 (m, 2H), 0.99 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 395 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.21 (t, J=5.9 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.33 (s, 1H), 8.13-8.09 (m, 1H), 7.89 (s, 1H), 7.55-7.48 (m, 2H), 7.40 (s, 1H), 6.86 (d, J=8.7 Hz, 1H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.61 (dd, J=6.9, 5.1 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 4.40-4.32 (m, 2H), 3.03-2.92 (m, 2H), 2.14-2.05 (m, 2H), 1.68 (qd, J=12.5, 3.9 Hz, 2H); MS (ESI(+)) m/e 390 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(4-aminophenyl)-2-cyclopentylacetamide for 3-methylbutan-1-amine and 2-(imidazo[1,2-a]pyridin-7-yl)acetic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, methanol-d4) δ ppm 8.75 (dd, J=6.9, 1.0 Hz, 1H), 8.21-8.16 (m, 1H), 8.01 (d, J=2.1 Hz, 1H), 7.89 (s, 1H), 7.55-7.45 (m, 5H), 3.99 (s, 2H), 2.39-2.24 (m, 3H), 1.91-1.76 (m, 2H), 1.78-1.46 (m, 4H), 1.39-1.15 (m, 2H); MS (ESI(+)) m/e 377 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.88 (t, J=6.1 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 8.15 (s, 1H), 7.90-7.86 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.17 (d, J=3.5 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.65 (d, J=3.5 Hz, 1H), 4.49 (d, J=6.1 Hz, 2H), 3.95 (d, J=7.2 Hz, 2H), 2.21-2.05 (m, 1H), 0.85 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 364 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.92 (t, J=6.1 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.27 (d, J=0.7 Hz, 1H), 7.93 (d, J=0.7 Hz, 1H), 7.89 (t, J=0.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.41-7.23 (m, 6H), 7.17 (d, J=3.5 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.68 (d, J=3.5 Hz, 1H), 5.39 (s, 2H), 4.49 (d, J=6.1 Hz, 2H); MS (ESI(+)) m/e 398 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting (S)-1-((tetrahydrofuran-2-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.94 (t, J=6.1 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.15 (s, 1H), 7.89 (s, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.17 (d, J=3.5 Hz, 1H), 6.86 (dd, J=7.0, 1.7 Hz, 1H), 6.68 (d, J=3.5 Hz, 1H), 4.49 (d, J=6.1 Hz, 2H), 4.28-4.09 (m, 3H), 3.78-3.69 (m, 1H), 3.68-3.55 (m, 1H), 2.01-1.88 (m, 1H), 1.85-1.66 (m, 2H), 1.66-1.54 (m, 1H); MS (ESI(+)) m/e 392 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting (R)-1-((tetrahydrofuran-2-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.94 (t, J=6.1 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.15 (s, 1H), 7.89 (s, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.17 (d, J=3.5 Hz, 1H), 6.86 (dd, J=7.0, 1.7 Hz, 1H), 6.68 (d, J=3.5 Hz, 1H), 4.49 (d, J=6.1 Hz, 2H), 4.28-4.07 (m, 3H), 3.78-3.69 (m, 1H), 3.68-3.59 (m, 1H), 2.01-1.88 (m, 1H), 1.85-1.66 (m, 2H), 1.66-1.54 (m, 1H); MS (ESI(+)) m/e 392 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)furan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.00 (t, J=5.3 Hz, 1H), 8.49 (dd, J=7.0, 0.7 Hz, 1H), 7.89 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (s, 1H), 7.13 (d, J=3.5 Hz, 1H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.58 (d, J=3.0 Hz, 1H), 6.53 (s, 1H), 4.47 (d, J=6.1 Hz, 2H), 4.25 (s, 1H), 4.13 (s, 1H), 3.66 (dd, J=12.2, 6.1 Hz, 2H), 3.01-2.82 (m, 1H), 2.47 (bs, 1H), 2.36 (bs, 1H), 1.09-0.86 (m, 6H); MS (ESI(+)) m/e 393 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.00 (dd, J=8.8, 5.7 Hz, 1H), 8.49 (dd, J=7.0, 0.5 Hz, 1H), 7.89 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (s, 1H), 7.13 (dd, J=3.4, 2.1 Hz, 1H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.58 (dd, J=6.2, 3.5 Hz, 1H), 6.52 (d, J=15.2 Hz, 1H), 4.47 (d, J=6.1 Hz, 2H), 4.17 (dd, J=21.3, 2.5 Hz, 2H), 3.74-3.53 (m, 2H), 2.45 (bs, 1H), 2.37 (bs, 1H), 2.27 (d, J=7.0 Hz, 1H), 2.22 (d, J=6.9 Hz, 1H), 2.06-1.94 (m, 1H), 0.91 (dd, J=6.5, 5.3 Hz, 6H); MS (ESI(+)) m/e 407 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.62 (t, J=5.4 Hz, 1H), 8.44-8.39 (m, 1H), 7.81 (s, 1H), 7.51-7.35 (m, 7H), 7.08 (d, J=3.5 Hz, 1H), 6.82 (dd, J=7.0, 1.6 Hz, 1H), 6.53 (d, J=3.5 Hz, 1H), 6.50-6.43 (m, 1H), 4.47 (d, J=6.1 Hz, 2H), 4.20 (d, J=2.1 Hz, 2H), 3.64 (t, J=5.3 Hz, 2H), 2.52-2.46 (m, 2H); MS (ESI(+)) m/e 427 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 4-isobutylphenylboronic acid for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.08 (t, J=6.1 Hz, 1H), 8.49 (dd, J=6.9, 0.8 Hz, 1H), 7.92-7.87 (m, 1H), 7.87-7.79 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.45-7.38 (m, 1H), 7.25 (d, J=8.3 Hz, 2H), 7.21 (d, J=3.6 Hz, 1H), 7.04 (d, J=3.6 Hz, 1H), 6.87 (dd, J=7.0, 1.7 Hz, 1H), 4.51 (d, J=6.0 Hz, 2H), 2.49-2.46 (m, 2H), 1.86 (dp, J=13.4, 6.8 Hz, 1H), 0.87 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 374 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and (2S)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.00 (t, J=5.0 Hz, 1H), 8.49 (dd, J=7.0, 0.6 Hz, 1H), 7.89 (s, 1H), 7.52 (d, J=1.1 Hz, 1H), 7.39 (s, 1H), 7.13 (d, J=3.5 Hz, 1H), 6.84 (dd, J=7.0, 1.6 Hz, 1H), 6.61-6.56 (m, 1H), 6.53 (d, J=9.8 Hz, 1H), 4.47 (d, J=6.1 Hz, 2H), 4.35-4.07 (m, 2H), 3.75-3.58 (m, 2H), 2.90-2.62 (m, 1H), 2.48-2.30 (m, 2H), 1.57 (dt, J=24.3, 8.8 Hz, 1H), 1.32 (dt, J=13.1, 6.8 Hz, 1H), 0.99 (dd, J=9.6, 6.8 Hz, 3H), 0.81 (q, J=7.1 Hz, 3H); MS (ESI(+)) m/e 407 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and 3,3-dimethylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.00 (t, J=6.1 Hz, 1H), 8.49 (dd, J=7.0, 0.7 Hz, 1H), 7.89 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (s, 1H), 7.13 (t, J=3.4 Hz, 1H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.57 (dd, J=6.1, 3.6 Hz, 1H), 6.51 (d, J=23.1 Hz, 1H), 4.47 (d, J=6.0 Hz, 2H), 4.19 (dd, J=31.4, 2.4 Hz, 2H), 3.73-3.62 (m, 2H), 2.41 (d, J=31.8 Hz, 2H), 2.28 (d, J=17.4 Hz, 2H), 0.99 (d, J=7.2 Hz, 9H); MS (ESI(+)) m/e 421 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and cyclopropylacetic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.05-8.93 (m, 1H), 8.49 (dd, J=7.0, 0.8 Hz, 1H), 7.90-7.87 (m, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (bs, 1H), 7.13 (d, J=3.5 Hz, 1H), 6.84 (dd, J=7.0, 1.6 Hz, 1H), 6.58 (dd, J=6.9, 3.5 Hz, 1H), 6.55-6.48 (m, 1H), 4.47 (d, J=6.1 Hz, 2H), 4.15 (d, J=8.4 Hz, 2H), 3.63 (dt, J=18.3, 5.7 Hz, 2H), 2.48-2.35 (m, 2H), 2.35-2.27 (m, 2H), 1.03-0.91 (m, 1H), 0.49-0.41 (m, 2H), 0.12 (dq, J=10.2, 5.0 Hz, 2H); MS (ESI(+)) m/e 405 (M+H)+.
- tert-Butyl 3-carbamothioylpyrrolidine-1-carboxylate (5 g, 21.71 mmol), 2-chloromalonaldehyde (3.70 g, 34.7 mmol) and magnesium carbonate (1.830 g, 21.71 mmol) were combined in dioxane (100 ml). The mixture was heated to 60° C. for 3 hours, stirred overnight at room temperature and then filtered through a pad of diatomaceous earth, rinsing with dichloromethane. The filtrate was concentrated in vacuo and then purified by normal phase chromatography to provide the title compound.
- tert-Butyl 3-(5-formylthiazol-2-yl)pyrrolidine-1-carboxylate (3.65 g, 12.93 mmol) was suspended in water (35 ml) and t-butanol (60 ml). Sodium dihydrogenphosphate (2.094 g, 17.45 mmol) was added, followed by 2-methylbut-2-ene (5.34 ml, 50.4 mmol). After 5 minutes, sodium chlorite (2.92 g, 32.3 mmol) was added in portions over about 5 minutes (mildly exothermic). The reaction was stirred for 1 hour at room temperature, then additional 2-methyl-2-butene (2 mL) was added. After stirring for 2 hours at room temperature, the reaction was concentrated and water (100 mL) was added. The mixture was adjusted to pH 2 by addition of 1N hydrochloric acid, then extracted dichloromethane. The organic extracts were dried over sodium sulfate, filtered and concentrated to provide the title compound.
- The title compound was prepared as described in Example 688D, substituting 2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)thiazole-5-carboxylic acid for lithium 2-(1-phenylpiperidin-4-yl)thiazole-5-carboxylate.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 3-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiazol-2-yl)pyrrolidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate.
- N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(pyrrolidin-3-yl)thiazole-5-carboxamide, 2.7-trifluoroacetic acid (150 mg, 0.236 mmol) was dissolved in N,N-dimethylformamide (0.7 mL). Triethylamine (0.3 mL, 2.152 mmol) was added, followed by 2-methylpropane-1-sulfonyl chloride (74.0 mg, 0.472 mmol) and the reaction was stirred overnight at room temperature. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extracts were dried with sodium sulfate, filtered, and concentrated and purified by normal phase chromatography to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.24 (t, J=5.9 Hz, 1H), 8.49 (d, J=7.0 Hz, 1H), 8.35 (s, 1H), 7.89 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.41 (s, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 3.91 (p, J=7.2 Hz, 1H), 3.74 (dd, J=9.8, 7.3 Hz, 1H), 3.51-3.35 (m, 3H), 2.99 (d, J=6.6 Hz, 2H), 2.46-2.33 (m, 1H), 2.24-2.03 (m, 2H), 1.03 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 448 (M+H)+.
- The title compound was prepared as described in Example 682, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(pyrrolidin-3-yl)thiazole-5-carboxamide for N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.20 (t, J=5.9 Hz, 1H), 8.50 (dd, J=7.0, 0.9 Hz, 1H), 8.21 (s, 1H), 7.89 (t, J=0.9 Hz, 1H), 7.84-7.77 (m, 2H), 7.74-7.65 (m, 1H), 7.65-7.57 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (bs, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.47 (d, J=5.9 Hz, 2H), 3.80-3.59 (m, 2H), 3.44-3.31 (m, 3H), 2.32-2.17 (m, 1H), 2.06-1.93 (m, 1H); MS (ESI(+)) m/e 468 (M+H)+.
- The title compound was prepared as described in Example 682, substituting 2-methylpropane sulfonyl chloride for benzenesulfonyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.04-8.96 (m, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.89-7.87 (m, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (s, 1H), 7.13 (d, J=3.5 Hz, 1H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.62-6.57 (m, 1H), 6.56-6.51 (m, 1H), 4.47 (d, J=6.1 Hz, 2H), 3.97-3.91 (m, 2H), 3.40 (t, J=5.7 Hz, 2H), 2.97 (d, J=6.5 Hz, 2H), 2.54-2.48 (m, 2H), 2.19-2.05 (m, 1H), 1.07-1.01 (m, 6H); MS (ESI(+)) m/e 443 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 5-(1-isobutyl-1H-pyrazol-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.10-9.01 (m, 2H), 8.53 (d, J=1.3 Hz, 1H), 8.18-8.16 (m, 1H), 8.14 (d, J=0.5 Hz, 1H), 7.83-7.79 (m, 2H), 7.76 (d, J=3.9 Hz, 1H), 7.22 (d, J=3.9 Hz, 1H), 4.54 (d, J=5.7 Hz, 2H), 3.92 (d, J=7.2 Hz, 2H), 2.13 (dp, J=13.6, 6.7 Hz, 1H), 0.85 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 381 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-methyl-4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)piperidine-1-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.02 (t, J=6.0 Hz, 1H), 8.49 (dd, J=7.0, 0.8 Hz, 1H), 8.13 (s, 1H), 7.91-7.86 (m, 1H), 7.81 (d, J=0.4 Hz, 1H), 7.74 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.23 (d, J=3.8 Hz, 1H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 4.48 (d, J=5.8 Hz, 2H), 4.02 (s, 2H), 3.65-3.50 (m, 2H), 3.19-3.02 (m, 2H), 1.47-1.34 (m, 11H), 1.30-1.15 (m, 2H), 0.93 (s, 3H); MS (ESI(+)) m/e 535 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate. 1H NMR (500 MHz, DMSO-d6) δ ppm 14.80 (s, 1H), 9.65 (t, J=6.0 Hz, 1H), 9.20 (s, 1H), 8.99 (s, 1H), 8.91 (d, J=7.0 Hz, 1H), 8.36 (d, J=2.0 Hz, 1H), 8.21 (s, 1H), 8.17 (d, J=2.1 Hz, 1H), 7.96 (d, J=3.9 Hz, 1H), 7.86 (s, 1H), 7.84 (s, 1H), 7.51 (dd, J=7.0, 1.4 Hz, 1H), 7.28 (d, J=3.8 Hz, 1H), 4.64 (d, J=5.8 Hz, 2H), 4.10 (s, 2H), 3.19-3.12 (m, 2H), 3.04-2.96 (m, 2H), 1.74-1.59 (m, 2H), 1.57-1.46 (m, 2H), 0.96 (s, 3H); MS (ESI(+)) m/e 435 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-((4-fluorotetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.97 (t, J=6.1 Hz, 1H), 8.50 (dd, J=13.4, 3.5 Hz, 1H), 8.16 (s, 1H), 7.94 (s, 1H), 7.92 (s, 1H), 7.56 (d, J=1.1 Hz, 1H), 7.43 (s, 1H), 7.18 (d, J=3.5 Hz, 1H), 6.89 (dd, J=7.0, 1.5 Hz, 1H), 6.71 (d, J=6.4 Hz, 1H), 4.51 (d, J=6.1 Hz, 2H), 4.46 (d, J=21.9 Hz, 2H), 3.81-3.70 (m, 2H), 3.56-3.45 (m, 2H), 1.89-1.68 (m, 2H), 1.53 (t, J=11.7 Hz, 2H); MS (ESI(+)) m/e 424 (M+H)+.
- The title compound was prepared as described in Example 682, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.97 (t, J=6.1 Hz, 1H), 8.47 (d, J=6.5 Hz, 1H), 7.88 (s, 1H), 7.85-7.78 (m, 2H), 7.75-7.68 (m, 1H), 7.69-7.60 (m, 2H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 7.10 (d, J=3.5 Hz, 1H), 6.82 (dd, J=7.0, 1.7 Hz, 1H), 6.54 (d, J=3.5 Hz, 1H), 6.46-6.43 (m, 1H), 4.46 (d, J=6.1 Hz, 2H), 3.79-3.74 (m, 2H), 3.28-3.21 (m, 2H), 2.45 (s, 2H); MS (ESI(+)) m/e 463 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting 2-fluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(piperidin-4-yl)thiazole-5-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.23 (t, J=5.9 Hz, 1H), 8.49 (d, J=6.9 Hz, 1H), 8.34 (s, 1H), 7.89 (s, 1H), 7.56-7.36 (m, 4H), 7.35-7.25 (m, 2H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 4.61-4.52 (m, 1H), 4.48 (d, J=5.9 Hz, 2H), 3.51-3.39 (m, 1H), 3.42-3.34 (m, 1H), 3.23 (t, J=12.1 Hz, 1H), 3.01 (td, J=12.7, 2.9 Hz, 1H), 2.21-2.13 (m, 1H), 2.08-1.97 (m, 1H), 1.77-1.54 (m, 2H); MS (ESI(+)) m/e 464 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and 2-fluorobenzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.66-8.58 (m, 1H), 8.45-8.39 (m, 1H), 7.81 (s, 1H), 7.54-7.44 (m, 2H), 7.43-7.36 (m, 2H), 7.31-7.21 (m, 2H), 7.08 (d, J=3.5 Hz, 1H), 6.82 (dd, J=6.9, 1.7 Hz, 1H), 6.53 (d, J=3.4 Hz, 1H), 6.48 (bs, 1H), 4.47 (d, J=6.1 Hz, 2H), 4.41-3.34 (m, 4H), 2.52-2.37 (m, 2H); MS (ESI(+)) m/e 445 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(pyrrolidin-3-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and 2-fluorobenzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.95-8.88 (m, 1H), 8.43 (d, J=7.0 Hz, 1H), 8.32-8.17 (m, 1H), 7.82 (s, 1H), 7.53-7.35 (m, 4H), 7.30-7.19 (m, 2H), 6.85-6.78 (m, 1H), 4.50-4.44 (m, 2H), 4.05-3.23 (m, 5H), 2.45-2.11 (m, 2H); MS (ESI(+)) m/e 450 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(pyrrolidin-3-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.28-9.19 (m, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.34 (d, J=2.4 Hz, 1H), 7.91-7.87 (m, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.41 (s, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 4.11-3.33 (m, 5H), 3.17 (d, J=5.2 Hz, 1H), 2.74-2.59 (m, 1H), 2.46-2.00 (m, 6H), 1.03-0.97 (m, 1H); MS (ESI(+)) m/e 398 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(pyrrolidin-3-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.28-9.19 (m, 1H), 8.49 (d, J=7.0 Hz, 1H), 8.34 (d, J=2.4 Hz, 1H), 7.91-7.87 (m, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.43-7.38 (m, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 3.97-3.72 (m, 2H), 3.70-3.46 (m, 2H), 3.17 (d, J=5.1 Hz, 1H), 2.45-1.91 (m, 5H), 0.94-0.86 (m, 6H); MS (ESI(+)) m/e 412 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(pyrrolidin-3-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.94-8.87 (m, 1H), 8.43 (d, J=6.9 Hz, 1H), 8.27 (s, 1H), 8.23-8.16 (m, 1H), 7.82 (s, 1H), 7.52-7.38 (m, 6H), 6.81 (dd, J=6.9, 1.7 Hz, 1H), 4.47 (d, J=5.8 Hz, 2H), 3.94-3.84 (m, 2H), 3.76-3.53 (m, 3H), 2.44-2.34 (m, 1H), 2.24-2.14 (m, 1H); MS (ESI(+)) m/e 432 (M+H)+.
- 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.500 g, 2.58 mmol), tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate (0.593 g, 2.58 mmol) and 2-(tributylphosphoranylidene)acetonitrile (0.746 g, 3.09 mmol) were stirred together in toluene (10 ml) at 85° C. overnight. The reaction was concentrated and purified by normal phase chromatography to give the title compound.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethyl)piperazine-1-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.02 (t, J=6.0 Hz, 1H), 8.53-8.45 (m, 1H), 8.16 (s, 1H), 7.89 (d, J=0.7 Hz, 1H), 7.79 (d, J=0.5 Hz, 1H), 7.74 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (s, 1H), 7.22 (d, J=3.9 Hz, 1H), 6.84 (dd, J=7.0, 1.6 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 4.23 (t, J=6.5 Hz, 2H), 3.29-3.25 (m, 2H), 2.74 (t, J=6.6 Hz, 2H), 2.42-2.33 (m, 4H), 1.38 (s, 9H); MS (ESI(+)) m/e 536 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-[2-(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)ethyl]piperazine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.34 (t, J=5.9 Hz, 1H), 8.94 (s, 2H), 8.87 (d, J=7.0 Hz, 1H), 8.33 (dd, J=2.1, 0.7 Hz, 1H), 8.22 (d, J=0.8 Hz, 1H), 8.15 (d, J=2.1 Hz, 1H), 7.87 (d, J=0.8 Hz, 1H), 7.82 (d, J=3.9 Hz, 1H), 7.79 (s, 1H), 7.47 (dd, J=7.0, 1.5 Hz, 1H), 7.27 (d, J=3.8 Hz, 1H), 4.65 (d, J=5.9 Hz, 2H), 4.43-4.34 (m, 2H), 3.22-3.16 (m, 6H), 2.98-2.89 (m, 4H); MS (ESI(+)) m/e 436 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 5-bromofuran-2-carboxylic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 51A, substituting 1-((4-fluorotetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-bromofuran-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.93 (t, J=6.0 Hz, 1H), 8.90-8.85 (m, 1H), 8.48 (s, 1H), 8.13 (s, 1H), 7.92 (d, J=0.5 Hz, 1H), 7.84 (dd, J=9.2, 0.7 Hz, 1H), 7.66 (dd, J=9.2, 1.7 Hz, 1H), 7.16 (d, J=3.6 Hz, 1H), 6.70 (d, J=3.5 Hz, 1H), 4.56 (d, J=6.0 Hz, 2H), 4.45 (d, J=21.8 Hz, 2H), 3.82-3.66 (m, 2H), 3.51 (td, J=11.2, 2.0 Hz, 2H), 1.92-1.63 (m, 2H), 1.60-1.42 (m, 2H); MS (ESI(+)) m/e 425 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-{4-[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, methanol-d4) δ ppm 9.24 (s, 1H), 8.72-8.68 (m, 1H), 8.27-8.23 (m, 1H), 8.11-8.07 (m, 1H), 7.88-7.82 (m, 2H), 7.41-7.35 (m, 2H), 4.76 (s, 2H), 4.75-4.66 (m, 1H), 4.24-4.15 (m, 1H), 3.29-3.18 (m, 1H), 3.06-2.85 (m, 2H), 2.78-2.64 (m, 1H), 2.02-1.84 (m, 2H), 1.74-1.52 (m, 2H), 1.17-1.07 (m, 6H); MS (ESI(+)) m/e 406 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 4-fluorobenzoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, methanol-d4) δ ppm 9.29-9.25 (m, 1H), 8.72 (d, J=1.4 Hz, 1H), 8.27 (d, J=1.7 Hz, 1H), 8.12 (d, J=1.7 Hz, 1H), 7.89-7.83 (m, 2H), 7.55-7.45 (m, 2H), 7.44-7.38 (m, 2H), 7.25-7.16 (m, 2H), 4.87-4.84 (m, 1H), 4.77 (s, 2H), 3.90-3.79 (m, 1H), 3.33-3.19 (m, 1H), 3.03-2.89 (m, 2H), 2.07-1.61 (m, 4H); MS (ESI(+)) m/e 458 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 2,5-difluorobenzoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, methanol-d4) δ ppm 9.23 (s, 1H), 8.69 (s, 1H), 8.24 (d, J=1.6 Hz, 1H), 8.07 (d, J=1.6 Hz, 1H), 7.89-7.83 (m, 2H), 7.43-7.36 (m, 2H), 7.31-7.15 (m, 3H), 4.84-4.73 (m, 3H), 3.71-3.62 (m, 1H), 3.36-3.24 (m, 1H), 3.04-2.90 (m, 2H), 2.04-1.95 (m, 1H), 1.92-1.61 (m, 3H); MS (ESI(+)) m/e 476 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 1-methylcyclopropanecarboxylic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, methanol-d4) δ ppm 9.28 (s, 1H), 8.73 (s, 1H), 8.28 (d, J=1.7 Hz, 1H), 8.13 (d, J=1.7 Hz, 1H), 7.89-7.83 (m, 2H), 7.42-7.36 (m, 2H), 4.78 (s, 2H), 4.62-4.53 (m, 2H), 3.20-2.70 (m, 3H), 1.97-1.89 (m, 2H), 1.72-1.57 (m, 2H), 1.33 (s, 3H), 0.96-0.89 (m, 2H), 0.71-0.58 (m, 2H); MS (ESI(+)) m/e 418 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 3,3,3-trifluoropropanoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, methanol-d4) δ ppm 9.22 (d, J=1.4 Hz, 1H), 8.68 (d, J=1.4 Hz, 1H), 8.23 (d, J=1.9 Hz, 1H), 8.06 (d, J=1.6 Hz, 1H), 7.89-7.82 (m, 2H), 7.42-7.34 (m, 2H), 4.81-4.65 (m, 3H), 4.11-3.99 (m, 1H), 3.62-3.44 (m, 2H), 3.37-3.21 (m, 1H), 3.01-2.86 (m, 1H), 2.85-2.71 (m, 1H), 1.99-1.85 (m, 2H), 1.85-1.54 (m, 2H); MS (ESI(+)) m/e 446 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, methanol-d4) δ ppm 99.24 (d, J=1.4 Hz, 1H), 8.70 (d, J=1.4 Hz, 1H), 8.25 (d, J=1.7 Hz, 1H), 8.09 (d, J=1.7 Hz, 1H), 7.89-7.82 (m, 2H), 7.41-7.34 (m, 2H), 4.79-4.66 (m, 3H), 4.19-4.07 (m, 1H), 3.30-3.16 (m, 1H), 3.00-2.85 (m, 1H), 2.80-2.63 (m, 1H), 2.36-2.29 (m, 2H), 2.17-2.00 (m, 1H), 2.01-1.84 (m, 2H), 1.75-1.50 (m, 2H), 0.99 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 420 (M+H)+.
- The title compound was prepared as described in Example 682, substituting propane-2-sulfonyl chloride for benzenesulfonyl chloride and N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide. 1H NMR (500 MHz, methanol-d4) δ ppm 9.21 (d, J=1.4 Hz, 1H), 8.67 (d, J=1.4 Hz, 1H), 8.22 (d, J=1.6 Hz, 1H), 8.05 (d, J=1.6 Hz, 1H), 7.89-7.82 (m, 2H), 7.40-7.35 (m, 2H), 4.85-4.79 (m, 1H), 4.75 (s, 2H), 3.96-3.85 (m, 2H), 3.12-3.00 (m, 2H), 2.88-2.74 (m, 1H), 1.95-1.85 (m, 2H), 1.84-1.65 (m, 2H), 1.33 (d, J=6.8 Hz, 6H); MS (ESI(+)) m/e 442 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-isobutyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (t, J=6.1 Hz, 1H), 8.49 (dd, J=7.0, 0.7 Hz, 1H), 7.89 (s, 1H), 7.54-7.51 (m, 2H), 7.41 (s, 1H), 7.30 (d, J=3.6 Hz, 1H), 6.96 (d, J=3.6 Hz, 1H), 6.85 (dd, J=7.0, 1.6 Hz, 1H), 6.76 (d, J=1.9 Hz, 1H), 4.50 (d, J=6.0 Hz, 2H), 4.22 (d, J=7.3 Hz, 2H), 2.04 (dp, J=13.8, 6.8 Hz, 1H), 0.81 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 364 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 5-bromofuran-2-carboxylic acid for 4-bromoaniline.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 5-(1-isobutyl-1H-pyrazol-4-yl)furan-2-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.05-9.02 (m, 1H), 8.90 (t, J=6.0 Hz, 1H), 8.52 (d, J=1.4 Hz, 1H), 8.19-8.14 (m, 2H), 7.90-7.88 (m, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.17 (d, J=3.5 Hz, 1H), 6.65 (d, J=3.5 Hz, 1H), 4.56 (d, J=5.9 Hz, 2H), 3.96 (d, J=7.1 Hz, 2H), 2.20-2.07 (m, 1H), 0.85 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 365 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 5-(1-isobutyl-1H-pyrazol-4-yl)furan-2-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.94-8.85 (m, 2H), 8.48 (s, 1H), 8.14 (s, 1H), 7.87 (s, 1H), 7.84 (d, J=9.1 Hz, 1H), 7.66 (dd, J=9.1, 1.7 Hz, 1H), 7.16 (d, J=3.5 Hz, 1H), 6.64 (d, J=3.5 Hz, 1H), 4.56 (d, J=6.0 Hz, 2H), 3.95 (d, J=7.1 Hz, 2H), 2.21-1.97 (m, 1H), 0.90-0.76 (m, 6H); MS (ESI(+)) m/e 365 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-isopentyl-1H-pyrazol-5-ylboronic acid for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (t, J=6.1 Hz, 1H), 8.49 (dd, J=7.0, 0.8 Hz, 1H), 7.89 (s, 1H), 7.58-7.43 (m, 2H), 7.43-7.37 (m, 1H), 7.30 (d, J=3.5 Hz, 1H), 6.95 (d, J=3.6 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.73 (d, J=1.9 Hz, 1H), 4.50 (d, J=6.0 Hz, 2H), 4.44-4.36 (m, 2H), 1.68-1.38 (m, 3H), 0.84 (d, J=6.4 Hz, 6H); MS (ESI(+)) m/e 378 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-((4-methyltetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-bromofuran-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.95-8.83 (m, 2H), 8.48 (s, 1H), 8.15-8.09 (m, 1H), 7.88 (d, J=0.4 Hz, 1H), 7.83 (dd, J=9.2, 0.7 Hz, 1H), 7.66 (dd, J=9.2, 1.7 Hz, 1H), 7.16 (d, J=3.5 Hz, 1H), 6.66 (d, J=3.5 Hz, 1H), 4.56 (d, J=6.0 Hz, 2H), 4.06 (s, 2H), 3.68 (dt, J=11.4, 4.5 Hz, 2H), 3.51 (ddd, J=11.9, 9.3, 2.9 Hz, 2H), 1.50 (ddd, J=13.4, 9.2, 4.2 Hz, 2H), 1.31-1.17 (m, 2H), 0.96 (s, 3H); MS (ESI(+)) m/e 421 (M+H)+.
- The title compound was prepared as described in Example 688D, substituting 5-(methoxycarbonyl)thiophene-2-carboxylic acid for lithium 2-(1-phenylpiperidin-4-yl)thiazole-5-carboxylate.
- The title compound was prepared as described in Example 688C, substituting methyl 5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophene-2-carboxylate for ethyl 2-(1-phenylpiperidin-4-yl)thiazole-5-carboxylate.
- The title compound was prepared as described in Example 1A, substituting), (R)-2-(methoxymethyl)pyrrolidine for 3-methylbutan-1-amine and lithium 5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophene-2-carboxylate for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.23 (t, J=6.0 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 7.90-7.88 (m, 1H), 7.79 (d, J=4.0 Hz, 1H), 7.60 (d, J=4.0 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.42-7.39 (m, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.35-4.23 (m, 1H), 3.78-3.65 (m, 2H), 3.26 (s, 3H), 2.02-1.81 (m, 4H); MS (ESI(+)) m/e 399 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting), 2-isobutylpyrrolidine for 3-methylbutan-1-amine and lithium 5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophene-2-carboxylate for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.23 (t, J=6.0 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 7.90-7.88 (m, 1H), 7.79 (d, J=4.0 Hz, 1H), 7.60 (d, J=4.0 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.42-7.39 (m, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.35-4.23 (m, 1H), 3.78-3.65 (m, 2H), 3.26 (s, 3H), 2.02-1.81 (m, 4H); MS (ESI(+)) m/e 411 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-neopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.89 (t, J=6.1 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 8.11 (d, J=0.5 Hz, 1H), 7.95-7.83 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.46-7.34 (m, 1H), 7.17 (d, J=3.4 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.66 (d, J=3.5 Hz, 1H), 4.49 (d, J=6.0 Hz, 2H), 3.95 (s, 2H), 0.92 (s, 9H); MS (ESI(+)) m/e 378 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 2-fluorobenzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.08-9.00 (m, 2H), 8.49 (d, J=1.4 Hz, 1H), 8.16-8.13 (m, 1H), 7.92-7.85 (m, 2H), 7.79 (d, J=1.0 Hz, 1H), 7.57-7.23 (m, 6H), 4.74-4.61 (m, 1H), 4.57 (d, J=5.7 Hz, 2H), 3.54-3.43 (m, 1H), 3.24-3.14 (m, 1H), 3.00-2.79 (m, 2H), 1.97-1.84 (m, 1H), 1.82-1.47 (m, 3H); MS (ESI(+)) m/e 458 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and ethyl 5-bromothiophene-2-carboxylate for 4-bromoaniline.
- The title compound was prepared as described in Example 1B, substituting tert-butyl 4-(5-(ethoxycarbonyl)thiophen-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate for N-isopentyl-4-nitrobenzamide.
- In a 250 mL round bottom flask was mixed tert-butyl 4-(5-(ethoxycarbonyl)thiophen-2-yl)piperidine-1-carboxylate (5.00 g, 14.73 mmol) in tetrahydrofuran (50 ml). Aqueous 4N NaOH (38.41 ml, 73.6 mmol) solution was added along with some methanol (10 ml) to get a single phase solution. The mixture was stirred overnight at room temperature. The solvents were removed to give a white slurry that was diluted with water and adjusted to pH of 5 with 1N aqueous hydrochloric acid. Filtration provided the title compound.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 5-(1-(tert-butoxycarbonyl)piperidin-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-((imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl)thiophen-2-yl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 52A, substituting 2-fluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.05 (m, 2H), 8.50 (d, J=1.5 Hz, 1H), 8.16 (s, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.69 (d, J=3.7 Hz, 1H), 7.50 (m, 1H), 7.43 (m, 1H), 7.31 (m, 2H), 6.98 (d, J=3.8 Hz, 1H), 4.60 (m, 1H), 4.52 (d, J=5.8 Hz, 2H), 3.45 (m, 1H), 3.18 (m, 2H), 2.93 (m, 1H), 2.12-1.85 (m, 2H), 1.52 (m, 2H); MS (ESI(+)) m/e 464 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting 4-fluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.05 (m, 2H), 8.51 (d, J=1.4 Hz, 1H), 8.16 (t, J=0.8 Hz, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.70 (d, J=3.8 Hz, 1H), 7.49 (m, 2H), 7.28 (m, 2H), 6.99 (dd, J=3.7, 0.8 Hz, 1H), 4.54 (m, 1H), 4.52 (d, J=5.8 Hz, 2H), 3.65 (m, 1H), 3.15 (m, 2H), 2.93 (m, 1H), 1.97 (m, 2H), 1.59 (m, 2H); MS (ESI(+)) m/e 464 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting 2,4-difluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.05 (m, 2H), 8.50 (d, J=1.4 Hz, 1H), 8.16 (s, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.69 (d, J=3.8 Hz, 1H), 7.52 (m, 1H), 7.37 (td, J=9.7, 2.4 Hz, 1H), 7.19 (td, J=8.5, 2.5 Hz, 1H), 6.98 (d, J=3.8 Hz, 1H), 4.58 (m, 1H), 4.52 (d, J=5.8 Hz, 2H), 3.43 (m, 1H), 3.17 (m, 2H), 2.92 (m, 1H), 2.00 (m, 2H), 1.52 (m, 2H); MS (ESI(+)) m/e 482 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting 2,5-difluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.04 (m, 2H), 8.51 (d, J=1.5 Hz, 1H), 8.16 (s, 1H), 7.80 (d, J=1.1 Hz, 1H), 7.70 (d, J=3.8 Hz, 1H), 7.56 (m, 1H), 7.36 (m, 2H), 6.98 (d, J=3.8 Hz, 1H), 4.57 (m, 1H), 4.52 (d, J=5.8 Hz, 2H), 3.46 (m, 1H), 3.17 (m, 2H), 2.93 (m, 1H), 2.02 (m, 2H), 1.55 (m, 2H); MS (ESI(+)) m/e 482 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 5-(1-(tert-butoxycarbonyl)piperidin-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-(([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)carbamoyl)thiophen-2-yl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate.
- The title compound was prepared as described in Example 52A, substituting 2-fluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.03 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 7.50 (m, 1H), 7.42 (m, 1H), 7.31 (m, 2H), 6.97 (dd, J=3.7, 0.8 Hz, 1H), 4.60 (m, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.45 (m, 1H), 3.17 (m, 2H), 2.93 (m, 1H), 2.07 (m, 1H), 1.93 (m, 1H), 1.54 (m, 2H); MS (ESI(+)) m/e 464 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting 3-fluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.02 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.66 (m, 2H), 7.50 (m, 1H), 7.34-7.22 (m, 3H), 6.98 (d, J=3.8 Hz, 1H), 4.55 (m, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.56 (m, 1H), 3.13 (m, 2H), 2.91 (m, 1H), 1.97 (m, 2H), 1.60 (m, 2H); MS (ESI(+)) m/e 464 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting 4-fluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.02 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 7.47 (m, 2H), 7.27 (m, 2H), 6.98 (dd, J=3.7, 0.8 Hz, 1H), 4.55 (m, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.62 (m, 1H), 3.14 (m, 2H), 2.91 (m, 1H), 1.97 (m, 2H), 1.58 (m, 2H); MS (ESI(+)) m/e 464 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting 2,4-difluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.02 (t, J=5.9 Hz, 1H), 8.86 (m, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 7.52 (m, 1H), 7.36 (td, J=9.7, 2.4 Hz, 1H), 7.19 (m, 1H), 6.97 (dd, J=3.8, 0.8 Hz, 1H), 4.57 (m, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.46 (m, 1H), 3.18 (m, 2H), 2.92 (m, 1H), 2.07 (m, 1H), 1.93 (m, 1H), 1.52 (m, 2H); MS (ESI(+)) m/e 482 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting 2,5-difluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.02 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 7.37 (m, 3H), 6.97 (dd, J=3.7, 0.8 Hz, 1H), 4.57 (m, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.46 (m, 1H), 3.19 (m, 2H), 2.93 (m, 1H), 2.13 (m, 1H), 1.92 (m, 1H), 1.54 (m, 2H); MS (ESI(+)) m/e 482 (M+H)+.
- The title compound was prepared as described in Example 52A, substituting 3,5-difluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.02 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 7.34 (tt, J=9.4, 2.4 Hz, 1H), 7.19 (m, 2H), 6.98 (dd, J=3.8, 0.8 Hz, 1H), 4.55 (m, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.55 (m, 1H), 3.15 (m, 2H), 2.90 (m, 1H), 2.03 (m, 1H), 1.90 (m, 1H), 1.61 (m, 2H); MS (ESI(+)) m/e 482 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.03 (m, 2H), 8.50 (d, J=1.4 Hz, 1H), 8.16 (m, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.69 (d, J=3.8 Hz, 1H), 6.96 (dd, J=3.7, 0.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.49 (m, 1H), 4.02 (m, 1H), 3.13 (m, 2H), 2.90 (m, 1H), 2.64 (m, 1H), 1.99 (m, 2H), 1.43 (m, 2H), 1.00 (m, 6H); MS (ESI(+)) m/e 412 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.03 (m, 2H), 8.50 (d, J=1.4 Hz, 1H), 8.16 (s, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.69 (d, J=3.8 Hz, 1H), 6.96 (dd, J=3.7, 0.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.49 (m, 1H), 3.96 (m, 1H), 3.10 (m, 2H), 2.64 (m, 1H), 2.21 (d, J=7.0 Hz, 2H), 1.99 (m, 3H), 1.43 (m, 2H), 0.90 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 426 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (1-methylcyclopropyl)carboxylic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.03 (m, 2H), 8.50 (d, J=1.4 Hz, 1H), 8.16 (d, J=0.9 Hz, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.69 (d, J=3.8 Hz, 1H), 6.97 (dd, J=3.7, 0.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.33 (m, 2H), 3.11 (m, 1H), 2.93 (m, 2H), 1.99 (m, 2H), 1.47 (m, 2H), 1.23 (s, 3H), 0.80 (m, 2H), 0.54 (m, 2H); MS (ESI(+)) m/e 424 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 4,4,4-trifluorobutanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.03 (m, 2H), 8.50 (d, J=1.4 Hz, 1H), 8.16 (s, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.69 (d, J=3.8 Hz, 1H), 6.96 (dd, J=3.7, 0.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.47 (m, 1H), 3.94 (m, 1H), 3.13 (m, 2H), 2.66 (m, 3H), 2.50 (m, 2H), 1.97 (m, 2H), 1.57 (m, 1H), 1.41 (m, 1H); MS (ESI(+)) m/e 466 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and tetrahydro-2H-pyran-4-ylcarboxylic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.03 (m, 2H), 8.50 (d, J=1.4 Hz, 1H), 8.16 (s, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.69 (d, J=3.8 Hz, 1H), 6.96 (dd, J=3.7, 0.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.47 (m, 1H), 4.07 (m, 1H), 3.84 (m, 2H), 3.40 (m, 2H), 3.13 (m, 2H), 2.89 (m, 1H), 2.64 (m, 1H), 1.98 (m, 2H), 1.77-1.30 (m, 6H); MS (ESI(+)) m/e 454 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.01 (t, J=5.9 Hz, 1H), 8.86 (s, 1H), 8.47 (s, 1H), 7.83 (d, J=9.1 Hz, 1H), 7.64 (m, 2H), 6.96 (d, J=3.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.47 (m, 1H), 4.02 (m, 1H), 3.12 (m, 2H), 2.88 (m, 1H), 2.63 (m, 1H), 1.99 (m, 2H), 1.43 (m, 2H), 1.00 (m, 6H); MS (ESI(+)) m/e 412 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.01 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.47 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.95 (dd, J=3.7, 0.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.48 (m, 1H), 3.96 (m, 1H), 3.10 (m, 2H), 2.63 (m, 1H), 2.21 (m, 2H), 1.98 (m, 3H), 1.43 (m, 2H), 0.90 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 426 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (2S)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.01 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.47 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.95 (d, J=3.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.49 (m, 1H), 4.05 (m, 1H), 3.13 (m, 2H), 2.69 (m, 2H), 1.99 (m, 2H), 1.61-1.18 (m, 4H), 0.98 (m, 3H), 0.82 (m, 3H); MS (ESI(+)) m/e 426 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (1-methylcyclopropyl)carboxylic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.01 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.47 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.96 (dd, J=3.7, 0.9 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H), 4.33 (m, 2H), 3.10 (m, 1H), 2.92 (m, 2H), 1.98 (m, 2H), 1.47 (m, 2H), 1.23 (s, 3H), 0.80 (m, 2H), 0.53 (m, 2H); MS (ESI(+)) m/e 424 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 3,3,3-trifluoropropanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.02 (t, J=5.9 Hz, 1H), 8.86 (m, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.65 (m, 2H), 6.95 (dd, J=3.7, 0.9 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H), 4.45 (m, 1H), 3.90 (m, 1H), 3.66 (m, 2H), 3.13 (m, 2H), 2.70 (m, 1H), 1.97 (m, 2H), 1.57 (m, 1H), 1.42 (m, 1H); MS (ESI(+)) m/e 452 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 4,4,4-trifluorobutanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.01 (t, J=5.8 Hz, 1H), 8.86 (m, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.95 (dd, J=3.7, 0.8 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H), 4.47 (m, 1H), 3.94 (m, 1H), 3.12 (m, 2H), 2.65 (m, 3H), 2.50 (m, 2H), 1.96 (m, 2H), 1.57 (m, 1H), 1.41 (m, 1H); MS (ESI(+)) m/e 466 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (4,4-difluorocyclohexyl)carboxylic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.01 (t, J=5.8 Hz, 1H), 8.86 (m, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.96 (dd, J=3.7, 0.8 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H), 4.48 (m, 1H), 4.06 (m, 1H), 3.13 (m, 2H), 2.82 (m, 1H), 2.65 (m, 1H), 2.10-1.80 (m, 6H), 1.80-1.30 (m, 6H); MS (ESI(+)) m/e 488 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and tetrahydro-2H-pyran-4-ylcarboxylic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.01 (t, J=5.9 Hz, 1H), 8.86 (m, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.95 (dd, J=3.7, 0.8 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H), 4.48 (m, 1H), 4.06 (m, 1H), 3.84 (m, 2H), 3.38 (m, 2H), 3.12 (m, 2H), 2.89 (m, 1H), 2.64 (m, 1H), 1.98 (m, 2H), 1.65-1.30 (m, 6H); MS (ESI(+)) m/e 454 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 2-hydroxy-2-methylpropanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.01 (t, J=5.8 Hz, 1H), 8.86 (m, 1H), 8.47 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.95 (dd, J=3.7, 0.8 Hz, 1H), 5.39 (s, 1H), 5.00-4.30 (m, 2H), 4.53 (d, J=5.8 Hz, 2H), 3.10 (m, 1H), 3.10-2.60 (m, 2H), 1.96 (m, 2H), 1.50 (m, 2H), 1.32 (s, 6H); MS (ESI(+)) m/e 428 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (1-methylpiperidin-4-yl)carboxylic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.02 (t, J=5.8 Hz, 1H), 8.85 (s, 1H), 8.47 (s, 1H), 7.83 (d, J=9.1 Hz, 1H), 7.64 (m, 2H), 6.95 (d, J=3.8 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H), 4.48 (m, 1H), 4.00 (m, 1H), 3.04 (m, 4H), 2.80-2.57 (m, 4H), 2.13 (s, 3H), 2.07-1.80 (m, 4H), 1.81-0.93 (m, 4H); MS (ESI(+)) m/e 467 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 2-cyanobenzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.02 (t, J=5.8 Hz, 1H), 8.86 (m, 1H), 8.47 (s, 1H), 7.95 (m, 1H), 7.82 (m, 2H), 7.70-7.57 (m, 4H), 6.96 (dd, J=3.7, 0.8 Hz, 1H), 4.61 (m, 1H), 4.52 (d, J=5.8 Hz, 2H), 3.35 (m, 1H), 3.14 (m, 2H), 2.97 (m, 1H), 2.09 (m, 1H), 1.89 (m, 1H), 1.60 (m, 2H); MS (ESI(+)) m/e 471 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and pyridin-2-ylcarboxylic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.03 (t, J=5.8 Hz, 1H), 8.86 (m, 1H), 8.59 (m, 1H), 8.48 (s, 1H), 7.92 (td, J=7.7, 1.7 Hz, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 7.57 (dt, J=7.7, 1.1 Hz, 1H), 7.47 (m, 1H), 6.97 (dd, J=3.7, 0.8 Hz, 1H), 4.58 (m, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.72 (m, 1H), 3.17 (m, 2H), 2.93 (m, 1H), 2.08 (m, 1H), 1.91 (m, 1H), 1.58 (m, 2H); MS (ESI(+)) m/e 447 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting N-(4-aminophenyl)-2-cyclopentylacetamide for 3-methylbutan-1-amine and 2-(imidazo[1,2-a]pyridin-6-yl)acetic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.12 (bs, 1H), 9.77 (bs, 1H), 8.47-8.44 (m, 1H), 7.94 (s, 1H), 7.58-7.43 (m, 6H), 7.19 (dd, J=9.2, 1.7 Hz, 1H), 3.64 (bs, 2H), 2.30-2.19 (m, 3H), 1.82-1.65 (m, 2H), 1.66-1.43 (m, 4H), 1.26-1.08 (m, 2H); MS (ESI(+)) m/e 377 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-b]pyridazin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.15 (t, J=5.9 Hz, 1H), 8.24 (s, 1H), 8.07 (d, J=9.3 Hz, 1H), 7.88-7.82 (m, 2H), 7.75 (d, J=1.2 Hz, 1H), 7.41-7.34 (m, 2H), 7.20 (d, J=9.3 Hz, 1H), 4.63 (d, J=5.8 Hz, 2H), 4.13-4.03 (m, 2H), 2.91-2.67 (m, 3H), 1.80-1.72 (m, 2H), 1.61-1.44 (m, 2H), 1.42 (s, 9H); MS (ESI(+)) m/e 436 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-b]pyridazin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.38 (d, J=1.9 Hz, 1H), 8.28 (dd, J=9.4, 0.7 Hz, 1H), 8.07 (d, J=1.9 Hz, 1H), 7.90-7.84 (m, 2H), 7.79-7.66 (m, 3H), 4.91-4.79 (m, 2H), 2.43-2.25 (m, 3H), 1.92-1.78 (m, 2H), 1.79-1.50 (m, 4H), 1.33-1.18 (m, 2H); MS (ESI(+)) m/e 378 (M+H)+.
- Methyl 5-(chlorocarbonyl)thiophene-2-carboxylate (500 mg, 2.443 mmol) was dissolved in triethylamine (5 mL) and the suspension was degassed with nitrogen. Copper(I) iodide (40 mg, 0.210 mmol) and bistriphenylphosphine palladium chloride (40 mg, 0.057 mmol) were added followed by ethynylcyclopropane (162 mg, 2.443 mmol). The mixture was stirred overnight, diluted with methanol and concentrated to dryness. The crude material was partitioned between dichloromethane and water. The organic extracts were dried with sodium sulfate, filtered, concentrated and purified by normal phase chromatography to afford the title compound.
- Methyl 5-(3-cyclopropylpropioloyl)thiophene-2-carboxylate (100 mg, 0.427 mmol) was dissolved in N,N-dimethylformamide (2 mL), and the solution was cooled to 0° C. Benzylhydrazine hydrochloride (74.5 mg, 0.470 mmol) was added followed by potassium carbonate (77 mg, 0.555 mmol). The mixture was stirred at 0° C. until the ice bath melted and was stirred overnight at room temperature. The solution was partitioned between water and ethyl acetate. The organic extract was dried with sodium sulfate, filtered, concentrated and purified by normal phase chromatography to afford the title compound.
- The title compound was prepared as described in Example 4B, substituting methyl 5-(1-benzyl-3-cyclopropyl-1H-pyrazol-5-yl)thiophene-2-carboxylate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(1-benzyl-3-cyclopropyl-1H-pyrazol-5-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.04 (t, J=5.9 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 7.91-7.87 (m, 1H), 7.74 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.42-7.24 (m, 5H), 7.23-7.15 (m, 2H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.38 (s, 1H), 5.44 (bs, 2H), 4.47 (d, J=5.9 Hz, 2H), 1.94-1.81 (m, 1H), 0.97-0.86 (m, 2H), 0.72-0.59 (m, 2H); MS (ESI(+)) m/e 454 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 5-bromothiophene-2-carboxylic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 51A, substituting 1-neopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.10-8.99 (m, 2H), 8.53 (d, J=1.3 Hz, 1H), 8.17 (d, J=0.9 Hz, 1H), 8.10 (d, J=0.5 Hz, 1H), 7.82-7.78 (m, 2H), 7.76 (d, J=3.8 Hz, 1H), 7.23 (d, J=3.9 Hz, 1H), 4.54 (d, J=5.7 Hz, 2H), 3.92 (s, 2H), 0.92 (s, 9H); MS (ESI(+)) m/e 395 (M+H)+.
- The title compound was prepared as described in Example 682, substituting propane-2-sulfonyl chloride for benzenesulfonyl chloride and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.03 (t, J=5.8 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.97 (dd, J=3.7, 0.9 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.71 (m, 2H), 3.25 (m, 1H), 3.02 (m, 3H), 2.00 (m, 2H), 1.56 (m, 2H), 1.22 (d, J=6.8 Hz, 6H); MS (ESI(+)) m/e 448 (M+H)+.
- The title compound was prepared as described in Example 682, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.01 (t, J=5.9 Hz, 1H), 8.85 (s, 1H), 8.47 (s, 1H), 7.83 (d, J=9.1 Hz, 1H), 7.81-7.69 (m, 3H), 7.71-7.55 (m, 4H), 6.90 (d, J=3.8 Hz, 1H), 4.51 (d, J=5.8 Hz, 2H), 3.73 (m, 2H), 2.84 (m, 1H), 2.37 (m, 2H), 1.99 (m, 2H), 1.61 (m, 2H); MS (ESI(+)) m/e 482 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-((4-methyltetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.09-9.01 (m, 2H), 8.53 (d, J=1.4 Hz, 1H), 8.18-8.15 (m, 1H), 8.13 (d, J=0.5 Hz, 1H), 7.83-7.79 (m, 2H), 7.76 (d, J=3.9 Hz, 1H), 7.23 (d, J=3.9 Hz, 1H), 4.54 (d, J=5.7 Hz, 2H), 4.04 (s, 2H), 3.68 (dt, J=11.4, 4.5 Hz, 2H), 3.51 (ddd, J=11.8, 9.2, 2.9 Hz, 2H), 1.50 (ddd, J=13.4, 9.1, 4.1 Hz, 2H), 1.33-1.18 (m, 2H), 0.96 (s, 3H); MS (ESI(+)) m/e 437 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate for 3-methylbutan-1-amine and 2-(imidazo[1,2-a]pyridin-6-yl)acetic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.14 (s, 1H), 8.52 (s, 1H), 8.01 (d, J=1.3 Hz, 1H), 7.65-7.58 (m, 2H), 7.54-7.47 (m, 2H), 7.31 (dd, J=9.2, 1.7 Hz, 1H), 7.20-7.13 (m, 2H), 4.11-3.99 (m, 2H), 3.68 (s, 2H), 2.89-2.54 (m, 3H), 1.76-1.66 (m, 2H), 1.53-1.32 (m, 11H); MS (ESI(+)) m/e 435 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylacetyl)amino]phenyl}piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 2-(imidazo[1,2-a]pyridin-6-yl)-N-(4-(piperidin-4-yl)phenyl)acetamide for 3-methylbutan-1-amine and 2-fluorobenzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.77 (s, 1H), 8.21 (d, J=2.2 Hz, 1H), 8.03 (d, J=2.1 Hz, 1H), 8.01-7.94 (m, 1H), 7.93-7.87 (m, 1H), 7.55-7.35 (m, 4H), 7.33-7.26 (m, 1H), 7.25-7.17 (m, 3H), 4.83-4.74 (m, 1H), 3.91 (s, 2H), 3.68-3.58 (m, 1H), 3.30-3.18 (m, 1H), 3.02-2.78 (m, 2H), 2.01-1.91 (m, 1H), 1.87-1.50 (m, 3H); MS (ESI(+)) m/e 457 (M+H)+.
- The title compound was prepared as described in Example 682, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide. 1H NMR (400 MHz, methanol-d4) δ ppm 9.04-8.96 (m, 1H), 8.51 (s, 1H), 8.05 (s, 1H), 7.85-7.79 (m, 5H), 7.73-7.66 (m, 1H), 7.67-7.59 (m, 2H), 7.35-7.28 (m, 2H), 4.72-4.67 (m, 2H), 3.96-3.88 (m, 2H), 2.63-2.51 (m, 1H), 2.48-2.37 (m, 2H), 1.93-1.85 (m, 2H), 1.86-1.72 (m, 2H); MS (ESI(+)) m/e 476 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 2-(imidazo[1,2-a]pyridin-6-yl)-N-(4-(piperidin-4-yl)phenyl)acetamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.77 (d, J=1.4 Hz, 1H), 8.21 (dd, J=2.2, 0.7 Hz, 1H), 8.03 (d, J=2.2 Hz, 1H), 8.01-7.94 (m, 1H), 7.93-7.87 (m, 1H), 7.53-7.47 (m, 2H), 7.23-7.17 (m, 2H), 4.73-4.64 (m, 1H), 4.21-4.13 (m, 1H), 3.91 (s, 2H), 3.27-3.14 (m, 1H), 2.99 (hept, J=6.7 Hz, 1H), 2.88-2.74 (m, 1H), 2.76-2.63 (m, 1H), 1.96-1.81 (m, 2H), 1.71-1.45 (m, 2H), 1.16-1.07 (m, 6H); MS (ESI(+)) m/e 405 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 2-(imidazo[1,2-a]pyridin-6-yl)-N-(4-(piperidin-4-yl)phenyl)acetamide for 3-methylbutan-1-amine and 2,4-difluorobenzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.77 (d, J=1.4 Hz, 1H), 8.23-8.18 (m, 1H), 8.03 (d, J=2.2 Hz, 1H), 8.01-7.94 (m, 1H), 7.93-7.87 (m, 1H), 7.54-7.42 (m, 3H), 7.25-7.19 (m, 2H), 7.13-7.05 (m, 2H), 4.84-4.74 (m, 2H), 3.91 (s, 2H), 3.68-3.59 (m, 1H), 3.30-3.20 (m, 1H), 3.02-2.79 (m, 1H), 2.00-1.91 (m, 1H), 1.88-1.52 (m, 3H); MS (ESI(+)) m/e 475 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(methoxycarbonyl)benzoic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 4B, substituting methyl 4-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)benzoate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
- The title compound was prepared as described in Example 1A, substituting 2-isobutylpyrrolidine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.17 (t, J=5.9 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 7.95 (d, J=8.2 Hz, 2H), 7.89 (d, J=1.2 Hz, 1H), 7.56 (d, J=8.0 Hz, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 6.86 (dd, J=7.0, 1.7 Hz, 1H), 4.52 (d, J=5.9 Hz, 2H), 4.25-4.14 (m, 1H), 3.58-3.51 (m, 1H), 3.51-3.38 (m, 1H), 2.09-1.53 (m, 5H), 1.33-1.17 (m, 2H), 0.94 (d, J=6.4 Hz, 6H); MS (ESI(+)) m/e 405 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting (2R)-2-(methoxymethyl)pyrrolidine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.18 (t, J=4.8 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 7.95 (d, J=8.3 Hz, 2H), 7.88 (s, 1H), 7.57 (d, J=7.7 Hz, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 6.86 (dd, J=7.0, 1.6 Hz, 1H), 4.52 (d, J=5.9 Hz, 2H), 3.62-2.88 (br m, 8H), 2.05-1.64 (br m, 4H); MS (ESI(+)) m/e 393 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(phenylsulfonyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.53 (t, J=5.9 Hz, 1H), 8.83 (d, J=6.9 Hz, 1H), 8.30 (d, J=2.1 Hz, 1H), 8.16-8.07 (m, 5H), 8.03-7.97 (m, 2H), 7.80-7.61 (m, 4H), 7.46 (dd, J=6.9, 1.6 Hz, 1H), 4.68 (d, J=5.8 Hz, 2H); MS (ESI(+)) m/e 392 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(phenylsulfonyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.32 (t, J=5.8 Hz, 1H), 8.92-8.87 (m, 1H), 8.49-8.46 (m, 1H), 8.07 (m, 4H), 8.01-7.95 (m, 2H), 7.85-7.78 (m, 1H), 7.75-7.67 (m, 1H), 7.68-7.60 (m, 3H), 4.57 (d, J=5.7 Hz, 2H); MS (ESI(+)) m/e 393 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethyl)piperazine-1-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(2-(4-(5-((imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl)furan-2-yl)-1H-pyrazol-1-yl)ethyl)piperazine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.70 (s, 2H), 9.28 (t, J=6.1 Hz, 1H), 8.87 (d, J=6.7 Hz, 1H), 8.33 (s, 2H), 8.15 (d, J=2.1 Hz, 1H), 8.00 (s, 1H), 7.82 (s, 1H), 7.49 (dd, J=7.0, 1.5 Hz, 1H), 7.26 (d, J=3.5 Hz, 1H), 6.72 (d, J=3.5 Hz, 1H), 4.73-4.59 (m, 4H), 3.66-3.56 (m, 2H), 3.41 (d, J=11.4 Hz, 8H); MS (ESI(+)) m/e 420 (M+H)+.
- The title compound was prepared as described in Example 857, substituting methylhydrazine for benzylhydrazine in Example 857B. 1H NMR (300 MHz, DMSO-d6) δ 9.04 (t, J=6.0 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 7.89 (s, 1H), 7.73 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.30 (d, J=3.8 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.32 (s, 1H), 4.47 (d, J=5.9 Hz, 2H), 3.84 (s, 3H), 1.97-1.84 (m, 1H), 1.04-0.89 (m, 2H), 0.75-0.63 (m, 2H); MS (ESI(+)) m/e 378 (M+H)+.
- The title compound was prepared as described in Example 857, substituting (2-methoxyethyl)hydrazine for benzylhydrazine in Example 857B. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.04 (t, J=6.0 Hz, 1H), 8.49 (dd, J=7.0, 1.0 Hz, 1H), 7.89 (s, 1H), 7.73 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.31 (d, J=3.8 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.31 (s, 1H), 4.47 (d, J=5.9 Hz, 2H), 4.33 (t, J=5.5 Hz, 2H), 3.73 (t, J=5.5 Hz, 2H), 3.24 (s, 3H), 2.00-1.87 (m, 1H), 1.01-0.92 (m, 2H), 0.72-0.63 (m, 2H); MS (ESI(+)) m/e 422 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethyl)piperazine-1-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(2-(4-(5-((imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl)thiophen-2-yl)-1H-pyrazol-1-yl)ethyl)piperazine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.52 (s, 2H), 9.28-9.17 (m, 2H), 8.68 (d, J=1.2 Hz, 1H), 8.36-8.30 (m, 1H), 8.27 (d, J=0.4 Hz, 1H), 8.05 (d, J=1.4 Hz, 1H), 7.91 (d, J=0.5 Hz, 1H), 7.81 (d, J=3.9 Hz, 1H), 7.27 (d, J=3.9 Hz, 1H), 4.71-4.48 (m, 2H), 4.07 (s, 8H), 3.37 (s, 4H); MS (ESI(+)) m/e 437 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(phenylsulfonyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.38 (t, J=5.8 Hz, 1H), 9.11 (s, 1H), 8.61-8.57 (m, 1H), 8.18 (s, 1H), 8.16-8.03 (m, 4H), 8.04-7.97 (m, 2H), 7.93-7.89 (m, 1H), 7.76-7.68 (m, 1H), 7.70-7.61 (m, 2H), 4.60 (d, J=5.7 Hz, 2H); MS (ESI(+)) m/e 393 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(phenylsulfonyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.47 (t, J=5.8 Hz, 1H), 8.82 (s, 1H), 8.35-8.30 (m, 1H), 8.19-8.14 (m, 1H), 8.12-8.08 (m, 4H), 8.05-7.88 (m, 4H), 7.76-7.68 (m, 1H), 7.68-7.60 (m, 2H), 4.61 (d, J=5.8 Hz, 2H); MS (ESI(+)) m/e 392 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 1-isobutyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.24 (t, J=5.9 Hz, 1H), 8.51 (dd, J=7.0, 0.7 Hz, 1H), 7.90 (d, J=0.8 Hz, 1H), 7.87 (d, J=3.9 Hz, 1H), 7.57-7.49 (m, 2H), 7.43 (s, 1H), 7.39 (d, J=3.9 Hz, 1H), 6.87 (dd, J=7.0, 1.6 Hz, 1H), 6.56 (d, J=1.9 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 4.08 (d, J=7.4 Hz, 2H), 2.09 (dp, J=13.8, 6.9 Hz, 1H), 0.80 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 380 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate for 3-methylbutan-1-amine and 2-(imidazo[1,2-a]pyridin-7-yl)acetic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.16 (s, 1H), 8.55 (d, J=6.9 Hz, 1H), 7.97 (s, 1H), 7.65-7.53 (m, 2H), 7.53-7.47 (m, 2H), 7.20-7.13 (m, 2H), 7.01-6.95 (m, 1H), 4.09-4.00 (m, 2H), 3.72 (s, 2H), 2.87-2.55 (m, 3H), 1.76-1.67 (m, 2H), 1.50-1.35 (m, 11H); MS (ESI(+)) m/e 435 (M+H)+.
- The title compound was prepared as described in Example 396, substituting 4-(2-cyclopentylacetamido)-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide for 4-(3-imidazo[1,2-a]pyridin-6-ylureido)-N-((tetrahydro-2H-pyran-2-yl)methyl)benzamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.07 (s, 1H), 9.09 (s, 1H), 8.95 (t, J=5.7 Hz, 1H), 8.28 (s, 1H), 7.95 (s, 1H), 7.87-7.81 (m, 2H), 7.69-7.63 (m, 2H), 4.61 (d, J=5.6 Hz, 2H), 2.38-2.12 (m, 3H), 1.80-1.64 (m, 2H), 1.66-1.40 (m, 4H), 1.25-1.09 (m, 2H); MS (ESI(+)) m/e 412 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 2-(imidazo[1,2-a]pyridin-7-yl)-N-(4-(piperidin-4-yl)phenyl)acetamide for 3-methylbutan-1-amine and 2,4-difluorobenzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.29 (s, 1H), 8.84 (d, J=6.9 Hz, 1H), 8.31 (d, J=1.9 Hz, 1H), 8.14 (d, J=2.1 Hz, 1H), 7.89 (s, 1H), 7.56-7.47 (m, 3H), 7.47-7.40 (m, 1H), 7.42-7.31 (m, 1H), 7.23-7.15 (m, 3H), 4.68-4.60 (m, 1H), 3.95 (bs, 2H), 3.58-3.44 (m, 1H), 3.26-3.09 (m, 1H), 2.94-2.70 (m, 2H), 1.94-1.81 (m, 1H), 1.79-1.40 (m, 3H); MS (ESI(+)) m/e 475 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 2-(imidazo[1,2-a]pyridin-7-yl)-N-(4-(piperidin-4-yl)phenyl)acetamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.28 (s, 1H), 8.84 (d, J=6.9 Hz, 1H), 8.34-8.28 (m, 1H), 8.18-8.14 (m, 1H), 7.89 (s, 1H), 7.55-7.43 (m, 3H), 7.22-7.16 (m, 2H), 4.60-4.50 (m, 1H), 4.09-4.00 (m, 1H), 3.96 (s, 2H), 3.18-3.01 (m, 1H), 2.96-2.82 (m, 1H), 2.79-2.67 (m, 1H), 2.63-2.50 (m, 1H), 1.87-1.70 (m, 2H), 1.57-1.30 (m, 2H), 1.07-0.93 (m, 6H); MS (ESI(+)) m/e 405 (M+H)+.
- The title compound was prepared as described in Example 396, substituting 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-(1-isobutyrylpiperidin-4-yl)phenyl)urea for 4-(3-imidazo[1,2-a]pyridin-6-ylureido)-N-((tetrahydro-2H-pyran-2-yl)methyl)benzamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.31 (bs, 1H), 8.24 (d, J=7.0 Hz, 1H), 7.58 (s, 1H), 7.46 (s, 1H), 7.35-7.29 (m, 2H), 7.12-7.02 (m, 3H), 6.62-6.55 (m, 1H), 4.38 (d, J=6.0 Hz, 2H), 4.36-4.19 (m, 2H), 2.93-2.62 (m, 4H), 1.85-1.77 (m, 2H), 1.53-1.37 (m, 2H), 1.03 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 454 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 2-(imidazo[1,2-a]pyridin-7-yl)-N-(4-(piperidin-4-yl)phenyl)acetamide for 3-methylbutan-1-amine and 2-fluorobenzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.75 (d, J=7.0 Hz, 1H), 8.18 (d, J=2.2 Hz, 1H), 8.00 (d, J=2.2 Hz, 1H), 7.89 (s, 1H), 7.56-7.35 (m, 5H), 7.33-7.25 (m, 1H), 7.25-7.17 (m, 3H), 4.83-4.74 (m, 1H), 3.99 (s, 2H), 3.68-3.59 (m, 1H), 3.31-3.18 (m, 1H), 3.03-2.76 (m, 2H), 2.00-1.92 (m, 1H), 1.87-1.51 (m, 3H); MS (ESI(+)) m/e 457 (M+H)+.
- The title compound was prepared as described in Example 857, substituting 4-methylpent-1-yne for ethynylcyclopropane in Example 857A and methylhydrazine for benzylhydrazine in Example 857B. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.05 (t, J=5.9 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 7.89 (s, 1H), 7.74 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.35 (d, J=3.8 Hz, 1H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 6.46 (s, 1H), 4.48 (d, J=5.9 Hz, 2H), 3.75 (s, 3H), 2.54-2.51 (m, 2H), 1.96-1.84 (m, 1H), 0.94 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 394 (M+H)+.
- The title compound was prepared as described in Example 857, substituting 4-methylpent-1-yne for ethynylcyclopropane in Example 857A. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.05 (t, J=5.8 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 7.89 (s, 1H), 7.76 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.42-7.38 (m, 2H), 7.37-7.23 (m, 3H), 7.17-7.11 (m, 2H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.56 (s, 1H), 5.35 (bs, 2H), 4.48 (d, J=5.9 Hz, 2H), 2.49-2.45 (m, 2H), 1.87-1.74 (m, 1H), 0.87 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 470 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)-2-fluorobenzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.27 (s, 1H), 9.13 (s, 1H), 8.73-8.65 (m, 1H), 8.59-8.56 (m, 1H), 8.24 (s, 1H), 7.94-7.91 (m, 1H), 7.75-7.67 (m, 2H), 7.34 (dd, J=8.5, 1.9 Hz, 1H), 4.59 (d, J=5.8 Hz, 2H), 2.37-2.32 (m, 2H), 2.32-2.16 (m, 1H), 1.82-1.68 (m, 2H), 1.67-1.44 (m, 4H), 1.26-1.10 (m, 2H); MS (ESI(+)) m/e 396 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 2,5-difluorobenzyl amine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.42 (t, J=5.9 Hz, 1H), 9.20 (t, J=5.8 Hz, 1H), 8.83 (d, J=6.9 Hz, 1H), 8.29 (d, J=2.0 Hz, 1H), 8.10 (d, J=2.0 Hz, 1H), 8.04-8.00 (m, 4H), 7.78 (s, 1H), 7.45 (dd, J=6.9, 1.6 Hz, 1H), 7.32-7.12 (m, 3H), 4.69 (d, J=5.8 Hz, 2H), 4.52 (d, J=5.7 Hz, 2H); MS (ESI(+)) m/e 421 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting (propan-2-yl)pyrrolidine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.44-9.36 (m, 1H), 8.86 (d, J=6.9 Hz, 1H), 8.31 (d, J=2.1 Hz, 1H), 8.14 (d, J=2.1 Hz, 1H), 8.01-7.95 (m, 2H), 7.80 (s, 1H), 7.65-7.59 (m, 2H), 7.49 (d, J=7.6 Hz, 1H), 4.69 (d, J=5.8 Hz, 2H), 4.15-4.05 (m, 1H), 3.47-3.19 (m, 2H), 2.39-2.26 (m, 1H), 1.96-1.57 (m, 4H), 0.93-0.85 (m, 6H); MS (ESI(+)) m/e 391 (M+H)+.
- A suspension of 4-nitrobenzohydrazide (0.500 g, 2.76 mmol), and 4-methylmorpholine (0.455 ml, 4.14 mmol) were stirred in dichloromethane (20 ml). 3,3-Dimethylbutanoyl chloride (0.422 ml, 3.04 mmol) was added and the reaction mixture was stirred for 2 hours. Normal phase chromatography of the crude reaction mixture gave the title compound.
- A mixture of N′-(3,3-dimethylbutanoyl)-4-nitrobenzohydrazide (0.556 g, 1.991 mmol) and methyl N-(triethylammoniumsulfonyl)carbamate (0.572 g, 2.389 mmol) in tetrahydrofuran (10 ml) was heated to 120° C. in a microwave (Biotage Initiator) for 45 minutes. The crude reaction mixture was concentrated and purified by normal phase chromatography to give the title compound.
- The title compound was prepared as described in Example 1B, substituting 2-neopentyl-5-(4-nitrophenyl)-1,3,4-oxadiazole for tert-butyl 4-(4-(1-(benzyloxycarbonyl)azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 4-(5-neopentyl-1,3,4-oxadiazol-2-yl)aniline for tert-butyl 4-(4-aminophenoxy)piperidine-1-carboxylate and 2-(imidazo[1,2-a]pyridin-7-yl)acetic acid for 1-(benzyloxycarbonyl)azetidine-3-carboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.55 (s, 1H), 8.49 (d, J=7.0 Hz, 1H), 7.96-7.89 (m, 3H), 7.86-7.79 (m, 2H), 7.53 (d, J=1.1 Hz, 1H), 7.49 (s, 1H), 6.88 (dd, J=7.0, 1.6 Hz, 1H), 3.77 (s, 2H), 2.82 (s, 2H), 1.02 (s, 9H); MS (ESI(+)) m/e 390 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 4-bromo-2-fluoroaniline for 4-bromoaniline.
- The title compound was prepared as described in Example 1B, substituting tert-butyl 4-(4-amino-3-fluorophenyl)-5,6-dihydropyridine-1(2H)-carboxylate for N-isopentyl-4-nitrobenzamide.
- The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-amino-3-fluorophenyl)piperidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.49 (d, J=7.0 Hz, 1H), 8.37 (d, J=2.3 Hz, 1H), 7.97 (t, J=8.5 Hz, 1H), 7.88 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (s, 1H), 7.12-7.04 (m, 2H), 7.00-6.94 (m, 1H), 6.82 (dd, J=7.0, 1.6 Hz, 1H), 4.35 (d, J=5.9 Hz, 2H), 4.10-4.01 (m, 2H), 2.89-2.56 (m, 3H), 1.77-1.68 (m, 2H), 1.41 (s, 11H); MS (ESI(+)) m/e 468 (M+H)+.
- The title compound was prepared as described in Example 1068, substituting pyrrolidine-1-carbonyl chloride for piperidine-1-carbonyl chloride. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.28-9.21 (m, 1H), 8.85 (d, J=7.0 Hz, 1H), 8.31 (d, J=2.1 Hz, 1H), 8.13 (d, J=2.1 Hz, 1H), 7.91-7.85 (m, 2H), 7.77 (s, 1H), 7.47 (dd, J=7.0, 1.6 Hz, 1H), 7.43-7.36 (m, 2H), 4.67 (d, J=5.8 Hz, 2H), 3.83-3.75 (m, 2H), 3.35-3.23 (m, 4H), 2.85-2.72 (m, 3H), 1.81-1.69 (m, 6H), 1.71-1.53 (m, 2H); MS (ESI(+)) m/e 432 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting tert-butyl 4-(4-amino-3-fluorophenyl)piperidine-1-carboxylate for 3-methylbutan-1-amine and 2-(imidazo[1,2-a]pyridin-7-yl)acetic acid hydrochloride for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.97 (s, 1H), 8.58 (d, J=6.9 Hz, 1H), 8.00 (s, 1H), 7.77-7.67 (m, 2H), 7.58 (d, J=1.4 Hz, 1H), 7.15 (dd, J=12.2, 1.9 Hz, 1H), 7.06-6.99 (m, 2H), 4.10-4.01 (m, 2H), 3.82 (bs, 2H), 2.94-2.58 (m, 3H), 1.78-1.69 (m, 2H), 1.53-1.36 (m, 11H); MS (ESI(+)) m/e 453 (M+H)+.
- A solution of piperidine-1-carbonyl chloride (0.033 g, 0.224 mmol) in N-methyl-2-pyrrolidinone (1 mL) was treated with N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide (0.05 g, 0.150 mmol) and triethylamine (0.042 ml, 0.299 mmol) and the reaction mixture was stirred at room temperature for 18 hours. The mixture was purified by reverse-phase HPLC to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.24 (t, J=5.9 Hz, 1H), 8.84 (d, J=7.0 Hz, 1H), 8.30 (d, J=2.1 Hz, 1H), 8.13 (d, J=2.1 Hz, 1H), 7.91-7.84 (m, 2H), 7.76 (s, 1H), 7.50-7.44 (m, 1H), 7.42-7.36 (m, 2H), 4.67 (d, J=5.8 Hz, 2H), 3.71-3.62 (m, 2H), 3.16-3.10 (m, 4H), 2.89-2.68 (m, 3H), 1.81-1.72 (m, 2H), 1.68-1.44 (m, 8H); MS (ESI(+)) m/e 446 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 1-(2-fluoro-4-(piperidin-4-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.73 (d, J=7.0 Hz, 1H), 8.16 (d, J=2.1 Hz, 1H), 7.99-7.95 (m, 1H), 7.85-7.77 (m, 2H), 7.50-7.39 (m, 6H), 7.11-6.99 (m, 2H), 4.84-4.72 (m, 1H), 4.60 (bs, 2H), 3.93-3.73 (m, 1H), 3.29-3.15 (m, 1H), 3.00-2.76 (m, 2H), 2.03-1.84 (m, 1H), 1.83-1.53 (m, 3H); MS (ESI(+)) m/e 472 (M+H)+.
-
TABLE 25 The following Examples were prepared essentially as described in Example 1069, substituting an appropriate carboxylic acid in Example 1069B. Ex Name MS 1070 1-{4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-2- (ESI(+)) fluorophenyl}-3-(imidazo[1,2-a]pyridin-7- m/e 452 ylmethyl)urea (M + H)+ 1071 1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-2- (ESI(+)) fluorophenyl}-3-(imidazo[1,2-a]pyridin-7- m/e 466 ylmethyl)urea (M + H)+ 1072 1-{2-fluoro-4-[1-(4-methylpentanoyl)piperidin-4- (ESI(+)) yl]phenyl}-3-(imidazo[1,2-a]pyridin-7- m/e 466 ylmethyl)urea (M + H)+ 1073 1-(2-fluoro-4-{1-[(2S)-2-methylbutanoyl]piperidin-4- (ESI(+)) yl}phenyl)-3-(imidazo[1,2-a]pyridin-7- m/e 452 ylmethyl)urea (M + H)+ 1074 1-{2-fluoro-4-[1-(tetrahydro-2H-pyran-4-ylcarbon- (ESI(+)) yl)piperidin-4-yl]phenyl}-3-(imidazo[1,2- m/e 480 a]pyridin-7-ylmethyl)urea (M + H)+ 1075 1-{2-fluoro-4-[1-(pyridin-2-ylcarbonyl)piperidin-4- (ESI(+)) yl]phenyl}-3-(imidazo[1,2-a]pyridin-7- m/e 473 ylmethyl)urea (M + H)+ 1076 1-{4-[1-(2-cyanobenzoyl)piperidin-4-yl]-2- (ESI(+)) fluorophenyl}-3-(imidazo[1,2-a]pyridin-7- m/e 497 ylmethyl)urea (M + H)+ 1078 1-{2-fluoro-4-[1-(2-methylpropanoyl)piperidin-4- (ESI(+)) yl]phenyl}-3-(imidazo[1,2-a]pyridin-7- m/e 438 ylmethyl)urea (M + H)+ - The title compound was prepared as described in Example 1068, substituting N,N-dimethylamine-1-carbonyl chloride for piperidine-1-carbonyl chloride. 1H NMR (400 MHz, methanol-d4) δ ppm 8.75 (d, J=7.0 Hz, 1H), 8.19-8.15 (m, 1H), 8.01-7.97 (m, 1H), 7.89-7.83 (m, 2H), 7.80 (s, 1H), 7.51-7.46 (m, 1H), 7.44-7.38 (m, 2H), 4.77 (s, 2H), 3.85-3.76 (m, 2H), 2.98-2.77 (m, 9H), 1.90-1.81 (m, 2H), 1.81-1.66 (m, 2H); MS (ESI(+)) m/e 406 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting (7-fluoroimidazo[1,2-a]pyridin-6-yl)methanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.08 (s, 1H), 8.87 (t, J=5.5 Hz, 1H), 8.56 (d, J=7.3 Hz, 1H), 7.96 (s, 1H), 7.88-7.82 (m, 2H), 7.71-7.64 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.46-7.39 (m, 1H), 4.49 (d, J=5.5 Hz, 2H), 2.36-2.30 (m, 2H), 2.31-2.15 (m, 1H), 1.81-1.68 (m, 2H), 1.68-1.43 (m, 4H), 1.26-1.10 (m, 2H); MS (ESI(+)) m/e 395 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting (7-fluoroimidazo[1,2-a]pyridin-6-yl)methanamine for 3-methylbutan-1-amine and 5-(1-isobutyl-1H-pyrazol-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.93 (t, J=5.5 Hz, 1H), 8.58 (d, J=7.7 Hz, 1H), 8.14 (d, J=0.8 Hz, 1H), 7.98 (s, 1H), 7.80 (d, J=0.8 Hz, 1H), 7.73 (d, J=3.8 Hz, 1H), 7.53 (d, J=1.3 Hz, 1H), 7.44 (d, J=11.0 Hz, 1H), 7.21 (d, J=3.8 Hz, 1H), 4.48 (d, J=5.5 Hz, 2H), 3.92 (d, J=7.2 Hz, 2H), 2.21-2.05 (m, 1H), 0.85 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 398 (M+H)+.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-{3-fluoro-4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting N-(2-fluoro-4-(piperidin-4-yl)phenyl)-2-(imidazo[1,2-a]pyridin-7-yl)acetamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.75 (dd, J=6.9, 0.9 Hz, 1H), 8.19 (dd, J=2.2, 0.8 Hz, 1H), 8.00 (d, J=2.2 Hz, 1H), 7.91 (s, 1H), 7.78 (t, J=8.2 Hz, 1H), 7.53-7.38 (m, 6H), 7.16-7.04 (m, 2H), 4.83-4.69 (m, 1H), 4.06 (s, 2H), 3.91-3.79 (m, 1H), 3.30-3.14 (m, 1H), 3.03-2.81 (m, 2H), 2.07-1.54 (m, 4H); MS (ESI(+)) m/e 457 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1 (2H)-yl)pyrimidine for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 4-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 4-bromoaniline. 1H NMR (400 MHz, DMSO d6) δ ppm 9.32 (t, J=5.9 Hz, 1H), 8.90-8.80 (m, 2H), 8.38 (dd, J=7.5, 1.2 Hz, 1H), 8.31 (d, J=2.0 Hz, 1H), 8.14 (d, J=2.1 Hz, 1H), 7.95 (d, J=8.5 Hz, 2H), 7.80 (s, 1H), 7.63 (d, J=8.4 Hz, 2H), 7.47 (dd, J=7.0, 1.5 Hz, 1H), 7.32-7.18 (m, 1H), 6.48-6.40 (m, 1H), 4.68 (d, J=5.8 Hz, 2H), 4.57-4.47 (m, 2H), 4.19-4.04 (m, 2H), 2.74-2.64 (m, 2H); MS (ESI(+)) m/e 411 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 2-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1 (2H)-yl)pyrimidine for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 4-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 4-bromoaniline. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.07-8.95 (m, 1H), 8.78 (dd, J=7.0, 0.5 Hz, 1H), 8.28-8.16 (m, 2H), 8.00 (d, J=2.0 Hz, 1H), 7.97-7.87 (m, 2H), 7.80-7.74 (m, 1H), 7.63-7.54 (m, 2H), 7.40 (dd, J=7.0, 1.5 Hz, 1H), 7.04 (d, J=7.4 Hz, 1H), 6.41-6.31 (m, 1H), 4.66 (m, 2H), 4.47 (m, 2H), 4.10 (t, J=5.8 Hz, 2H), 2.77-2.64 (m, 2H), 2.55 (s, 3H); MS (ESI(+)) m/e 425 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1 (2H)-yl)-6-(trifluoromethyl)pyrimidine for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 4-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 4-bromoaniline. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.30 (t, J=5.9 Hz, 1H), 8.84 (d, J=6.9 Hz, 1H), 8.68 (s, 1H), 8.29 (d, J=2.0 Hz, 1H), 8.11 (d, J=2.1 Hz, 1H), 7.99-7.89 (m, 2H), 7.77 (s, 1H), 7.72-7.58 (m, 2H), 7.45 (dd, J=7.0, 1.5 Hz, 1H), 7.38-7.20 (m, 1H), 6.43 (m, 1H), 4.67 (d, J=5.8 Hz, 2H), 4.53-4.31 (m, 2H), 4.13-3.92 (m, 2H), 2.70-2.62 (m, 2H); MS (ESI(+)) m/e 479 (M+H)+.
- In a 50 mL round-bottomed flask, bromine (3 mL) was cooled to 0 OC and iron (0.56 g) was added. The mixture was stirred at 0 OC for 30 minutes. 3,5-Dimethyladamantane-1-carboxylic acid (0.5 g) was added. The mixture was stirred at room temperature overnight. After adding ice and 6N aqueous HCl (10 mL), ethyl acetate (20 mL), and saturated aqueous sodium sulfite were added. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with saturated sodium sulfite and dried over sodium sulfate. After filtration and removal of the solvent, the product was used directly in the next step.
- To a solution of 5-bromo-3,7-dimethyltricyclo[3.3.1.13,7]decane-1-carboxylic acid (4.57 g, 15.9 mmol) in tetrahydrofuran (10 mL) was added borane tetrahydrofuran complex (50 mL, 1 M in THF) dropwise and the mixture was stirred at room temperature for 14 hours. The reaction mixture was quenched with methanol, concentrated and purified by normal phase chromatography to provide the title compound.
- To a solution of the 5-bromo-3,7-dimethyltricyclo[3.3.1.13,7]dec-1-ylmethanol (8.0 g, 29.3 mmol) in toluene (60 mL) was added 1H-pyrazole (1.55 g, 22.7 mmol) and cyanomethylenetributylphosphorane (2.0 g, 29.3 mmol) under nitrogen. After the addition, the mixture was stirred at 90° C. overnight. The reaction mixture was then concentrated, and the residue was purified by normal phase chromatography to give the title compound.
- To a solution of 1-(5-bromo-3,7-dimethyltricyclo[3.3.1.13,7]dec-1-yl)-1H-pyrazole (4.5 g) in ethane-1,2-diol (12 mL) was added triethylamine (3 mL) under nitrogen. The mixture was heated to 150 OC in a Biotage Initiator microwave reactor for 45 minutes. The mixture was poured over water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried with sodium sulfate, filtered and concentrated. The residue was purified by normal phase chromatography to give the title compound.
- To a cold (−78° C.) solution of the 2-{[3,5-dimethyl-7-(1H-pyrazol-1-ylmethyl)tricyclo[3.3.1.13,7]dec-1-yl]oxy}ethanol (3.69 g) in tetrahydrofuran (50 mL) was added n-butyllithium (20 mL, 2.5 M in hexane) under nitrogen. The mixture was stirred at −78° C. for 1.5 hours. Iodomethane (10 mL) was added by syringe, and the mixture was stirred for an additional 3 hours. The reaction mixture was then quenched by the addition of aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried with sodium sulfate, filtered and concentrated. The residue was purified by normal phase chromatography to give the title compound.
- To a solution of the 2-({3,5-dimethyl-7-[(5-methyl-1H-pyrazol-1-yl)methyl]tricyclo[3.3.1.13,7]dec-1-yl}oxy)ethanol (3.5 g, 11 mmol) in N,N-dimethylformamide (30 ml) was added N-iodosuccinimide (3.2 g, 14.22 mmol). The mixture was stirred at room temperature for 1.5 hours. The reaction mixture was then diluted with ethyl acetate and washed with aqueous sodium thiosulfate, water and brine. After drying over anhydrous sodium sulfate, the mixture was filtered and concentrated. The residue was purified by normal phase chromatography to give the title compound.
- To a cold (0° C.) solution of 1-({3,5-dimethyl-7-[2-(hydroxy)ethoxy]tricyclo[3.3.1.13,7]dec-1-yl}methyl)-4-iodo-5-methyl-1H-pyrazole (2.1 g) in methylene chloride (30 mL) was added triethylamine (1.42 g) followed by methanesulfonyl chloride (0.542 g). The mixture was stirred at room temperature for 1.5 hours and then was diluted with ethyl acetate. The layers were separated, and the organic layer was washed with water and brine, dried with sodium sulfate, filtered and concentrated to give the title compound, which was used in the next step without further purification.
- A solution of 2-({3-[(4-iodo-5-methyl-1H-pyrazol-1-yl)methyl]-5,7-dimethyltricyclo[3.3.1.13,7]dec-1-yl}oxy)ethyl methanesulfonate (2.5 g) in 2 M methylamine in methanol (15 mL) was heated to 100° C. for 20 minutes in a Biotage Initiator microwave reactor. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine. The organic layer was dried with sodium sulfate, filtered and concentrated to give the title compound which was used in the next reaction without further purification.
- To a solution of 1-({3,5-dimethyl-7-[2-(methylamino)ethoxy]tricyclo[3.3.1.13,7]dec-1-yl}methyl)-4-iodo-5-methyl-1H-pyrazole (2.2 g) in tetrahydrofuran (30 mL) was added Boc-anhydride (1.26 g) and a catalytic amount of 4-dimethylaminopyridine. The mixture was stirred at room temperature for 1.5 hours and diluted with ethyl acetate. The solution was washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was dried with sodium sulfate, filtered and concentrated. The residue was purified by normal phase chromatography to give the title compound
- To a solution of tert-butyl[2-({3-[(4-iodo-5-methyl-1H-pyrazol-1-yl)methyl]-5,7-dimethyltricyclo[3.3.1.13,7]dec-1-yl}oxy)ethyl]methylcarbamate (2.8 g, 5.02 mmol) in dioxane (40 ml) was added bis(benzonitrile)palladium(II) chloride (96 mg, 0.251 mmol), S-Phos (206 mg, 0.502 mmol), and pinacolborane (2 mL) followed by triethylamine (2.5 mL, 5.25 mmol) under nitrogen. The mixture was stirred at reflux overnight. The reaction mixture was then diluted with ethyl acetate and washed with water and brine. After drying (anhydrous sodium sulfate), the solution was filtered and concentrated and the residue was purified by normal phase chromatographyto give the title compound.
- The title compound was prepared as described in Example 51A, substituting tert-butyl {2-[(3,5-dimethyl-7-{[5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}tricyclo[3.3.1.13,7]dec-1-yl)oxy]ethyl}methylcarbamate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline followed by deprotection as described in Example 28A. 1H NMR (400 MHz, DMSO-d6) δ 9.50 (t, J=5.9 Hz, 1H), 8.88 (d, J=7.0 Hz, 1H), 8.76-8.64 (m, 2H), 8.34 (d, J=2.0 Hz, 1H), 8.16 (d, J=2.1 Hz, 1H), 7.93 (d, J=3.9 Hz, 1H), 7.83 (s, 1H), 7.76 (s, 1H), 7.49 (dd, J=7.0, 1.3 Hz, 1H), 7.23 (d, J=3.9 Hz, 1H), 4.65 (d, J=5.8 Hz, 2H), 3.92 (s, 2H), 3.63-3.55 (m, 2H), 3.04-2.91 (m, 2H), 2.51 (dd, J=6.0, 3.7 Hz, 3H), 2.45 (s, 3H), 1.42 (s, 2H), 1.31 (dd, J=27.3, 11.4 Hz, 4H), 1.16 (q, J=12.5 Hz, 4H), 1.07-0.99 (m, 2H), 0.87 (s, 6H); MS (ESI(+)) m/e 587 (M+H)+.
- The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and methyl 4-bromo-2-fluorobenzoate for 4-bromoaniline.
- The title compound was prepared as described in Example 1B, substituting tert-butyl 4-(3-fluoro-4-(methoxycarbonyl)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate for N-isopentyl-4-nitrobenzamide.
- The title compound was prepared as described in Example 4B, substituting tert-butyl 4-(3-fluoro-4-(methoxycarbonyl)phenyl)piperidine-1-carboxylate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
- The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-fluorobenzoic acid for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(3-fluoro-4-((imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl)phenyl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 1-methylcyclopropanecarboxylic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 9.27 (s, 1H), 8.72 (s, 1H), 8.28 (d, J=1.5 Hz, 1H), 8.11 (d, J=1.6 Hz, 1H), 7.78 (t, J=7.9 Hz, 1H), 7.27-7.11 (m, 2H), 4.79 (s, 2H), 4.63-4.51 (m, 2H), 3.23-2.72 (m, 3H), 1.99-1.88 (m, 2H), 1.71-1.54 (m, 2H), 1.33 (s, 3H), 1.02-0.83 (m, 2H), 0.73-0.55 (m, 2H); MS (ESI(+)) m/e 436 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 9.28-9.20 (m, 1H), 8.74-8.65 (m, 1H), 8.30-8.21 (m, 1H), 8.13-8.05 (m, 1H), 7.79 (t, J=7.9 Hz, 1H), 7.51-7.40 (m, 5H), 7.29-7.14 (m, 2H), 4.85-4.72 (m, 3H), 3.94-3.76 (m, 1H), 3.30-3.14 (m, 1H), 3.05-2.86 (m, 2H), 2.07-1.60 (m, 4H); MS (ESI(+)) m/e 458 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 9.26 (s, 1H), 8.75-8.66 (m, 1H), 8.31-8.22 (m, 1H), 8.14-8.06 (m, 1H), 7.78 (t, J=8.0 Hz, 1H), 7.27-7.10 (m, 2H), 4.79 (s, 2H), 4.75-4.66 (m, 1H), 4.26-4.14 (m, 1H), 3.29-3.15 (m, 1H), 3.09-2.86 (m, 2H), 2.79-2.61 (m, 1H), 2.05-1.85 (m, 2H), 1.74-1.48 (m, 2H), 1.18-1.05 (m, 6H); MS (ESI(+)) m/e 424 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting 2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 3,3,3-trifluoropropanoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 9.24 (s, 1H), 8.74-8.65 (m, 1H), 8.30-8.21 (m, 1H), 8.13-8.04 (m, 1H), 7.78 (t, J=7.9 Hz, 1H), 7.27-7.10 (m, 2H), 4.78 (s, 2H), 4.72-4.64 (m, 1H), 4.14-4.00 (m, 1H), 3.63-3.45 (m, 2H), 3.30-3.21 (m, 1H), 3.03-2.86 (m, 1H), 2.77 (m, 1H), 1.98-1.86 (m, 2H), 1.65 (m, 2H); MS (ESI(+)) m/e 464 (M+H)+.
- The title compound was prepared as described in Example 1A, substituting tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate for 3-methylbutan-1-amine and 2-([1,2,4]triazolo[4,3-a]pyridin-6-yl)acetic acid hydrochloride for 4-nitrobenzoic acid.
- The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(4-(2-([1,2,4]triazolo[4,3-a]pyridin-6-yl)acetamido)phenyl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
- The title compound was prepared as described in Example 1A, substituting 2-([1,2,4]triazolo[4,3-a]pyridin-6-yl)-N-(4-(piperidin-4-yl)phenyl)acetamide for 3-methylbutan-1-amine and 2-fluorobenzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 10.28-10.20 (m, 1H), 9.30 (s, 1H), 8.54 (s, 1H), 7.85-7.74 (m, 1H), 7.63-7.46 (m, 4H), 7.41-7.31 (m, 3H), 7.31-7.20 (m, 2H), 4.77-4.65 (m, 1H), 3.75 (s, 2H), 3.56-3.46 (m, 1H), 3.30-3.15 (m, 1H), 2.99-2.75 (m, 2H), 1.97-1.86 (m, 1H), 1.81-1.49 (m, 3H); MS (ESI(+)) m/e 458 (M+H)+.
- A solution of N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methylpiperidin-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide (0.100 g, 0.197 mmol) in N,N-dimethylformamide (2 ml) was added tert-butyl 4-(2-bromoethyl)piperazine-1-carboxylate (0.058 g, 0.197 mmol) followed by N,N-diisopropylethylamine (0.138 ml, 0.788 mmol) and the reaction was stirred overnight. The reaction mixture was purified directly using normal phase chromatography and the resulting material was treated with HCl in dioxane (4M) for 2 hours then concentrated to give the title compound as a hydrochloride salt. 1H NMR (500 MHz, DMSO-d6) δ 14.64 (s, 1H), 10.40 (s, 1H), 9.72 (s, 1H), 9.54 (t, J=6.0 Hz, 1H), 8.89 (d, J=6.9 Hz, 1H), 8.34 (d, J=1.8 Hz, 1H), 8.22 (s, 1H), 8.16 (d, J=2.1 Hz, 1H), 7.91 (d, J=3.9 Hz, 1H), 7.87 (s, 1H), 7.83 (s, 1H), 7.50 (dd, J=7.0, 1.4 Hz, 1H), 7.28 (d, J=3.8 Hz, 1H), 4.64 (d, J=5.8 Hz, 2H), 4.23-3.54 (m, 10H), 3.35 (d, J=38.3 Hz, 8H), 1.72 (d, J=77.7 Hz, 4H), 0.98 (s, 3H); MS (ESI(+)) m/e 547 (M+H)+.
- A suspension of N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methylpiperidin-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide (0.100 g, 0.197 mmol) and 4-methylmorpholine (0.108 ml, 0.985 mmol) in N,N-diisopropylethylamine (0.5 ml) was added to 2,5-dioxopyrrolidin-1-yl 2-bromoacetate (0.056 g, 0.236 mmol) in N,N-diisopropylethylamine (0.5 ml) and stirred at room temperature. After 1 hour, (R)-2-amino-3-mercaptopropanoic acid (0.119 g, 0.985 mmol) as a solution in water (1 ml) was added. After stirring an additional 1 hour, a few drops of TFA were added to form a homogeneous solution which was purified by revere phase chromatography. The product containing peaks were lyophilized to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 9.30 (t, J=6.0 Hz, 1H), 8.86 (d, J=7.0 Hz, 1H), 8.44 (bs, 2H), 8.32 (d, J=2.0 Hz, 1H), 8.18-8.11 (m, 2H), 7.86-7.77 (m, 3H), 7.46 (dd, J=7.0, 1.5 Hz, 1H), 7.27 (dd, J=3.7, 1.8 Hz, 1H), 4.65 (d, J=5.8 Hz, 2H), 4.21-4.13 (m, 1H), 4.13-4.02 (m, 2H), 4.02-3.92 (m, 1H), 3.87-3.57 (m, 3H), 3.42-3.29 (m, 1H), 3.29-3.18 (m, 1H), 3.10 (dd, J=14.6, 4.7 Hz, 1H), 2.98 (dd, J=14.6, 7.6 Hz, 1H), 1.60-1.18 (m, 4H), 0.96 (s, 3H); MS (ESI(+)) m/e 596 (M+H)+.
- A suspension of N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methylpiperidin-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide (0.139 g, 0.274 mmol), 2,2-dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azaicosan-20-oic acid (0.100 g, 0.274 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.104 g, 0.274 mmol) and 4-methylmorpholine (0.105 ml, 0.958 mmol) was stirred at room temperature for 3 hours. The reaction mixture was purified directly by normal phase chromatography and the resulting material was treated with HCl/dioxane (4 M) then concentrated to give the title compound as a hydrochloride salt. 1H NMR (400 MHz, DMSO-d6) δ 14.71 (s, 1H), 9.58 (t, J=6.0 Hz, 1H), 8.89 (d, J=7.0 Hz, 1H), 8.35 (d, J=1.9 Hz, 1H), 8.16 (d, J=2.1 Hz, 2H), 8.06 (s, 3H), 7.92 (d, J=3.9 Hz, 1H), 7.83 (s, 2H), 7.50 (dd, J=7.0, 1.2 Hz, 1H), 7.26 (d, J=3.8 Hz, 1H), 4.64 (d, J=5.8 Hz, 2H), 4.05 (s, 2H), 3.80 (dd, J=11.8, 6.8 Hz, 2H), 3.66-3.58 (m, 4H), 3.55 (dd, J=9.2, 4.4 Hz, 4H), 3.50 (t, J=7.5 Hz, 8H), 3.37-3.26 (m, 1H), 3.23-3.13 (m, 1H), 2.99-2.90 (m, 2H), 2.55 (t, J=6.6 Hz, 2H), 1.53-1.19 (m, 4H), 0.95 (s, 3H); MS (ESI(+)) m/e 682 (M+H)+.
- A suspension of N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methylpiperidin-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide (0.050 g, 0.099 mmol) and 4-methylmorpholine (0.054 ml, 0.493 mmol) in N,N-diisopropylethylamine (0.5 ml) was added to 2,5-dioxopyrrolidin-1-yl 3-(2-bromoacetamido)propanoate (0.036 g, 0.118 mmol) in N,N-diisopropylethylamine (0.5 ml) and the mixture was stirred at room temperature. After 1 hour, (R)-2-amino-3-mercaptopropanoic acid (0.060 g, 0.493 mmol) as a solution in water (1 ml) was added. After 1 hour, a few drops of TFA were added to form a homogeneous solution and the mixture was purified by chromatography to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 9.28 (t, J=5.9 Hz, 1H), 8.85 (d, J=7.0 Hz, 1H), 8.47 (s, 2H), 8.30 (d, J=1.9 Hz, 1H), 8.21 (t, J=5.6 Hz, 1H), 8.17-8.09 (m, 2H), 7.84 (s, 1H), 7.81-7.74 (m, 2H), 7.44 (dd, J=7.0, 1.1 Hz, 1H), 7.27 (d, J=3.8 Hz, 1H), 4.65 (d, J=5.8 Hz, 2H), 4.20 (dd, J=7.5, 4.3 Hz, 1H), 4.06 (s, 2H), 3.90-3.78 (m, 2H), 3.35-2.94 (m, 8H), 2.59-2.41 (m, 2H), 1.57-1.19 (m, 4H), 0.95 (s, 3H); MS (ESI(+)) m/e 667 (M+H)+.
Claims (3)
1-10. (canceled)
11. A method of treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia in a patient, said method comprising administering to the patient a therapeutically effective amount of a compound or a therapeutically acceptable salt thereof, selected from the group consisting of:
5-[1-({3,5-dimethyl-7-[2-(methylamino)ethoxy]tricyclo[3.3.1.13,7]dec-1-yl}methyl)-5-methyl-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-({4-methyl-1-[2-(piperazin-1-yl)ethyl]piperidin-4-yl}methyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
S-(2-{4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidin-1-yl}-2-oxoethyl)-L-cysteine;
5-(1-{[1-(15-amino-4,7,10,13-tetraoxapentadecan-1-oyl)-4-methylpiperidin-4-yl]methyl}-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; and
S-{2-[(3-{4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidin-1-yl}-3-oxopropyl)amino]-2-oxoethyl}-L-cysteine.
12. A method of treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia or spleen cancer in a patient, said method comprising administering to the patient therapeutically effective amount of the compound or a therapeutically acceptable salt thereof, selected from the group consisting of:
5-[1-({3,5-dimethyl-7-[2-(methylamino)ethoxy]tricyclo[3.3.1.13,7]dec-1-yl}methyl)-5-methyl-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide;
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-({4-methyl-[2-(piperazin-1-yl)ethyl]piperidin-4-yl}methyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide;
S-(2-{4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidin-1-yl}-2-oxoethyl)-L-cysteine;
5-(1-{[1-(15-amino-4,7,10,13-tetraoxapentadecan-1-oyl)-4-methylpiperidin-4-yl]methyl}-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; and
S-{2-[(3-{4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidin-1-yl}-3-oxopropyl)amino]-2-oxoethyl}-1-cysteine; and a therapeutically effective amount of one additional therapeutic agent or more than one additional therapeutic agent.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14/878,858 US20170135994A9 (en) | 2012-05-11 | 2015-10-08 | Nampt inhibitors |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261645679P | 2012-05-11 | 2012-05-11 | |
US201261718998P | 2012-10-26 | 2012-10-26 | |
US201361779626P | 2013-03-13 | 2013-03-13 | |
US13/891,349 US9193723B2 (en) | 2012-05-11 | 2013-05-10 | NAMPT inhibitors |
US13/891,366 US9187472B2 (en) | 2012-05-11 | 2013-05-10 | NAMPT inhibitors |
US14/878,858 US20170135994A9 (en) | 2012-05-11 | 2015-10-08 | Nampt inhibitors |
Related Parent Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/891,366 Division US9187472B2 (en) | 2012-05-11 | 2013-05-10 | NAMPT inhibitors |
US13/891,349 Division US9193723B2 (en) | 2012-05-11 | 2013-05-10 | NAMPT inhibitors |
Publications (2)
Publication Number | Publication Date |
---|---|
US20160184282A1 US20160184282A1 (en) | 2016-06-30 |
US20170135994A9 true US20170135994A9 (en) | 2017-05-18 |
Family
ID=48576512
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/891,349 Active US9193723B2 (en) | 2012-05-11 | 2013-05-10 | NAMPT inhibitors |
US13/891,366 Active US9187472B2 (en) | 2012-05-11 | 2013-05-10 | NAMPT inhibitors |
US14/878,836 Abandoned US20160184281A1 (en) | 2012-05-11 | 2015-10-08 | Nampt inhibitors |
US14/878,858 Abandoned US20170135994A9 (en) | 2012-05-11 | 2015-10-08 | Nampt inhibitors |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/891,349 Active US9193723B2 (en) | 2012-05-11 | 2013-05-10 | NAMPT inhibitors |
US13/891,366 Active US9187472B2 (en) | 2012-05-11 | 2013-05-10 | NAMPT inhibitors |
US14/878,836 Abandoned US20160184281A1 (en) | 2012-05-11 | 2015-10-08 | Nampt inhibitors |
Country Status (25)
Country | Link |
---|---|
US (4) | US9193723B2 (en) |
EP (1) | EP2847192A1 (en) |
JP (1) | JP2015516435A (en) |
KR (1) | KR20150007349A (en) |
CN (1) | CN104428301A (en) |
AR (1) | AR091022A1 (en) |
AU (1) | AU2013259344A1 (en) |
BR (1) | BR112014028042A2 (en) |
CA (1) | CA2873060A1 (en) |
CL (1) | CL2014003026A1 (en) |
CO (1) | CO7151512A2 (en) |
CR (1) | CR20140573A (en) |
DO (1) | DOP2014000253A (en) |
EC (1) | ECSP14030779A (en) |
HK (2) | HK1208221A1 (en) |
IL (1) | IL235354A0 (en) |
MX (1) | MX2014013734A (en) |
PE (1) | PE20150224A1 (en) |
PH (1) | PH12014502513A1 (en) |
RU (1) | RU2014150049A (en) |
SG (1) | SG11201407372UA (en) |
TW (1) | TW201350481A (en) |
UA (1) | UA114323C2 (en) |
WO (1) | WO2013170112A1 (en) |
ZA (1) | ZA201407904B (en) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR112014028042A2 (en) * | 2012-05-11 | 2017-06-27 | Abbvie Inc | nampt inhibitors |
US9266891B2 (en) | 2012-11-16 | 2016-02-23 | Boehringer Ingelheim International Gmbh | Substituted [1,2,4]triazolo[4,3-A]pyrazines that are BRD4 inhibitors |
US10144742B2 (en) | 2014-04-18 | 2018-12-04 | Millennium Pharmaceuticals, Inc. | Quinoxaline compounds and uses thereof |
TW201625641A (en) * | 2014-05-22 | 2016-07-16 | 健臻公司 | NAMPT inhibitors and methods |
MX2016015248A (en) * | 2014-06-25 | 2017-02-23 | Hoffmann La Roche | Imidazo[1,2-a]pyrazin-1yl-benzamide compounds for treating spinal muscular atrophy. |
EP3172205A1 (en) * | 2014-07-23 | 2017-05-31 | Aurigene Discovery Technologies Limited | 4,5-dihydroisoxazole derivatives as nampt inhibitors |
CN107438598A (en) | 2015-01-20 | 2017-12-05 | 米伦纽姆医药公司 | Quinazoline and quinoline compound and application thereof |
PE20181496A1 (en) * | 2015-10-23 | 2018-09-18 | Vifor Int Ag | NOVELTY FERROPORTIN INHIBITORS |
EP3438091A4 (en) * | 2016-03-30 | 2019-11-27 | Ajinomoto Co., Inc. | Compound having enhancing activity for glucagon-like peptide-1 receptor actions |
EP3279192A1 (en) * | 2016-08-05 | 2018-02-07 | Centre Hospitalier Universitaire Vaudois (CHUV) | Piperidine derivatives for use in the treatment of pancreatic cancer |
KR20190074292A (en) | 2016-10-18 | 2019-06-27 | 시애틀 지네틱스, 인크. | Targeted delivery of remedial pathway inhibitors of nicotinamide adenine dinucleotides |
JOP20180036A1 (en) | 2017-04-18 | 2019-01-30 | Vifor Int Ag | Novel ferroportin-inhibitor salts |
BR112019022445A2 (en) | 2017-04-27 | 2020-05-12 | Seattle Genetics, Inc. | COMPOSITION OF BINDER-DRUG CONJUGATE, FORMULATION, METHOD TO INHIBIT THE TUMOR CELL OR CANCER CELL MULTIPLICATION OR CAUSE APOPTOSIS IN A TUMOR OR CANCER CELL, AND, PHARMACEUTICAL CONNECTOR COMPOUND |
GB201908453D0 (en) * | 2019-06-12 | 2019-07-24 | Enterprise Therapeutics Ltd | Compounds for treating respiratory disease |
WO2021032935A1 (en) * | 2019-08-21 | 2021-02-25 | Kalvista Pharmaceuticals Limited | Enzyme inhibitors |
WO2021123051A1 (en) | 2019-12-20 | 2021-06-24 | Bayer Aktiengesellschaft | Substituted thiophene carboxamides, thiophene carboxylic acids and derivatives thereof |
Family Cites Families (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MY115155A (en) | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
US6277985B1 (en) | 1995-09-15 | 2001-08-21 | Pharmacia & Upjohn Company | Aminoaryl oxazolidinone N-oxides |
DE19624659A1 (en) | 1996-06-20 | 1998-01-08 | Klinge Co Chem Pharm Fab | New pyridylalkene and pyridylalkanoic acid amides |
DE19624668A1 (en) | 1996-06-20 | 1998-02-19 | Klinge Co Chem Pharm Fab | Use of pyridylalkane, pyridylalken or pyridylalkynamides |
US20030220234A1 (en) | 1998-11-02 | 2003-11-27 | Selvaraj Naicker | Deuterated cyclosporine analogs and their use as immunodulating agents |
GB9918037D0 (en) | 1999-07-30 | 1999-09-29 | Biochemie Gmbh | Organic compounds |
EP1348434A1 (en) | 2002-03-27 | 2003-10-01 | Fujisawa Deutschland GmbH | Use of pyridyl amides as inhibitors of angiogenesis |
WO2005016928A1 (en) * | 2003-08-15 | 2005-02-24 | Banyu Pharmaceutical Co., Ltd. | Imidazopyridine derivatives |
WO2005085252A1 (en) | 2004-03-04 | 2005-09-15 | Biofocus Discovery Limited | Imidazo ‘1,2-a’ pyrazine compounds which interact with protein kinases |
US7307163B2 (en) | 2004-04-19 | 2007-12-11 | Symed Labs Limited | Process for the preparation of linezolid and related compounds |
EP1768967B1 (en) | 2004-07-20 | 2009-04-22 | Symed Labs Limited | Novel intermediates for linezolid and related compounds |
WO2006015737A1 (en) * | 2004-08-02 | 2006-02-16 | Schwarz Pharma Ag | Indolizine carboxamides and the aza and diaza derivatives thereof |
US7511013B2 (en) | 2004-09-29 | 2009-03-31 | Amr Technology, Inc. | Cyclosporin analogues and their pharmaceutical uses |
TW200716636A (en) | 2005-05-31 | 2007-05-01 | Speedel Experimenta Ag | Heterocyclic spiro-compounds |
US7514068B2 (en) | 2005-09-14 | 2009-04-07 | Concert Pharmaceuticals Inc. | Biphenyl-pyrazolecarboxamide compounds |
WO2008026018A1 (en) | 2006-09-01 | 2008-03-06 | Topotarget Switzerland Sa | New method for the treatment of inflammatory diseases |
US8796267B2 (en) | 2006-10-23 | 2014-08-05 | Concert Pharmaceuticals, Inc. | Oxazolidinone derivatives and methods of use |
KR101222412B1 (en) | 2007-02-15 | 2013-01-15 | 에프. 호프만-라 로슈 아게 | 2-aminooxazolines as taar1 ligands |
KR20100012031A (en) | 2007-04-19 | 2010-02-04 | 콘서트 파마슈티컬즈, 인크. | Deuterated morpholinyl compounds |
US7531685B2 (en) | 2007-06-01 | 2009-05-12 | Protia, Llc | Deuterium-enriched oxybutynin |
US20090131485A1 (en) | 2007-09-10 | 2009-05-21 | Concert Pharmaceuticals, Inc. | Deuterated pirfenidone |
US20090118238A1 (en) | 2007-09-17 | 2009-05-07 | Protia, Llc | Deuterium-enriched alendronate |
US20090088416A1 (en) | 2007-09-26 | 2009-04-02 | Protia, Llc | Deuterium-enriched lapaquistat |
US20090082471A1 (en) | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched fingolimod |
WO2009045476A1 (en) | 2007-10-02 | 2009-04-09 | Concert Pharmaceuticals, Inc. | Pyrimidinedione derivatives |
US20090105338A1 (en) | 2007-10-18 | 2009-04-23 | Protia, Llc | Deuterium-enriched gabexate mesylate |
EP2212298B1 (en) | 2007-10-18 | 2013-03-27 | Concert Pharmaceuticals Inc. | Deuterated etravirine |
CA2703591C (en) | 2007-10-26 | 2013-05-07 | Concert Pharmaceuticals, Inc. | Deuterated darunavir |
EP2245029B1 (en) * | 2008-02-20 | 2015-04-15 | Novartis AG | Heterocyclic inhibitors of stearoyl-coa desaturase |
EP2098231A1 (en) | 2008-03-05 | 2009-09-09 | Topotarget Switzerland SA | Use of NAD formation inhibitors for the treatment of ischemia-reperfusion injury |
CA2809391A1 (en) * | 2010-09-03 | 2012-03-08 | Genentech, Inc. | 4-{[(pyridin-3-yl-methyl)aminocarbonyl]amino}benzene-sulfone derivatives as nampt inhibitors for therapy of diseases such as cancer |
RU2617988C2 (en) * | 2010-09-03 | 2017-05-02 | ФОРМА ТиЭм, ЭлЭлСИ | New compounds and compositions for nampt inhibition |
KR20130133905A (en) * | 2011-04-05 | 2013-12-09 | 화이자 리미티드 | Pyrrolo[2,3-d]pyrimidine derivatives as inhibitors of tropomyosin-related kinases |
RU2617643C2 (en) * | 2011-05-09 | 2017-04-25 | ФОРМА ТиЭм, ЭлЭлСИ | Novel compounds and compositions for inhibiting nampt |
WO2013091011A1 (en) * | 2011-12-21 | 2013-06-27 | Biota Europe Ltd | Heterocyclic urea compounds |
WO2013130935A1 (en) * | 2012-03-02 | 2013-09-06 | Genentech, Inc. | Amido-benzyl sulfoxide derivatives |
WO2013130943A1 (en) * | 2012-03-02 | 2013-09-06 | Genentech, Inc. | Alkyl-and di-substituted amido-benzyl sulfonamide derivatives |
WO2013127268A1 (en) * | 2012-03-02 | 2013-09-06 | Genentech,Inc. | Amido-benzyl sulfone and sulfonamide derivatives |
SG11201405054PA (en) * | 2012-03-02 | 2014-09-26 | Genentech Inc | Amido-benzyl sulfone and sulfoxide derivatives |
EP2820017B1 (en) * | 2012-03-02 | 2016-12-21 | Genentech, Inc. | Pyridinyl and pyrimidinyl sulfoxide and sulfone derivatives |
BR112014028042A2 (en) * | 2012-05-11 | 2017-06-27 | Abbvie Inc | nampt inhibitors |
WO2014111871A1 (en) * | 2013-01-17 | 2014-07-24 | Aurigene Discovery Technologies Limited | 4,5-dihydroisoxazole derivatives as nampt inhibitors |
-
2013
- 2013-05-10 BR BR112014028042A patent/BR112014028042A2/en not_active IP Right Cessation
- 2013-05-10 EP EP13726916.3A patent/EP2847192A1/en not_active Withdrawn
- 2013-05-10 RU RU2014150049A patent/RU2014150049A/en not_active Application Discontinuation
- 2013-05-10 US US13/891,349 patent/US9193723B2/en active Active
- 2013-05-10 MX MX2014013734A patent/MX2014013734A/en unknown
- 2013-05-10 PE PE2014002007A patent/PE20150224A1/en not_active Application Discontinuation
- 2013-05-10 TW TW102116754A patent/TW201350481A/en unknown
- 2013-05-10 WO PCT/US2013/040476 patent/WO2013170112A1/en active Application Filing
- 2013-05-10 JP JP2015511728A patent/JP2015516435A/en active Pending
- 2013-05-10 SG SG11201407372UA patent/SG11201407372UA/en unknown
- 2013-05-10 KR KR1020147034748A patent/KR20150007349A/en not_active Application Discontinuation
- 2013-05-10 CN CN201380037081.6A patent/CN104428301A/en active Pending
- 2013-05-10 CA CA2873060A patent/CA2873060A1/en not_active Abandoned
- 2013-05-10 AR ARP130101636A patent/AR091022A1/en unknown
- 2013-05-10 UA UAA201413266A patent/UA114323C2/en unknown
- 2013-05-10 AU AU2013259344A patent/AU2013259344A1/en not_active Abandoned
- 2013-05-10 US US13/891,366 patent/US9187472B2/en active Active
-
2014
- 2014-10-27 IL IL235354A patent/IL235354A0/en unknown
- 2014-10-29 ZA ZA2014/07904A patent/ZA201407904B/en unknown
- 2014-11-07 DO DO2014000253A patent/DOP2014000253A/en unknown
- 2014-11-07 CL CL2014003026A patent/CL2014003026A1/en unknown
- 2014-11-11 PH PH12014502513A patent/PH12014502513A1/en unknown
- 2014-12-03 CO CO14266532A patent/CO7151512A2/en unknown
- 2014-12-11 CR CR20140573A patent/CR20140573A/en unknown
- 2014-12-11 EC ECIEPI201430779A patent/ECSP14030779A/en unknown
-
2015
- 2015-09-10 HK HK15108839.1A patent/HK1208221A1/en unknown
- 2015-09-16 HK HK15109035.1A patent/HK1208450A1/en unknown
- 2015-10-08 US US14/878,836 patent/US20160184281A1/en not_active Abandoned
- 2015-10-08 US US14/878,858 patent/US20170135994A9/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
CL2014003026A1 (en) | 2014-12-26 |
EP2847192A1 (en) | 2015-03-18 |
AR091022A1 (en) | 2014-12-30 |
ECSP14030779A (en) | 2015-09-30 |
US20160184282A1 (en) | 2016-06-30 |
UA114323C2 (en) | 2017-05-25 |
CO7151512A2 (en) | 2014-12-29 |
PE20150224A1 (en) | 2015-03-08 |
US20160184281A1 (en) | 2016-06-30 |
CN104428301A (en) | 2015-03-18 |
IL235354A0 (en) | 2014-12-31 |
US9187472B2 (en) | 2015-11-17 |
CA2873060A1 (en) | 2013-11-14 |
BR112014028042A2 (en) | 2017-06-27 |
HK1208450A1 (en) | 2016-03-04 |
WO2013170112A1 (en) | 2013-11-14 |
JP2015516435A (en) | 2015-06-11 |
KR20150007349A (en) | 2015-01-20 |
US20130303508A1 (en) | 2013-11-14 |
AU2013259344A1 (en) | 2014-11-13 |
MX2014013734A (en) | 2015-06-10 |
HK1208221A1 (en) | 2016-02-26 |
US9193723B2 (en) | 2015-11-24 |
US20130303511A1 (en) | 2013-11-14 |
RU2014150049A (en) | 2016-07-10 |
SG11201407372UA (en) | 2014-12-30 |
PH12014502513A1 (en) | 2014-12-15 |
ZA201407904B (en) | 2017-08-30 |
CR20140573A (en) | 2015-02-25 |
TW201350481A (en) | 2013-12-16 |
DOP2014000253A (en) | 2015-01-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8975398B2 (en) | NAMPT inhibitors | |
US9187472B2 (en) | NAMPT inhibitors | |
US10093624B2 (en) | NAMPT and ROCK inhibitors | |
US20120122924A1 (en) | Nampt inhibitors | |
EP2776393B1 (en) | Nampt inhibitors | |
EP2852585A1 (en) | Nampt inhibitors | |
US9073922B2 (en) | Pyrrolo[2,3-B]pyridine CDK9 kinase inhibitors | |
US9796708B2 (en) | Pyrrolo [2,3-B] pyridine CDK9 kinase inhibitors | |
US9334264B2 (en) | NAMPT inhibitors | |
US9758511B2 (en) | NAMPT inhibitors | |
US20170253562A1 (en) | Nampt Inhibitors |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |