CA2691512A1 - Heteroaryl amide analogues - Google Patents

Info

Publication number

CA2691512A1

CA2691512A1 CA002691512A CA2691512A CA2691512A1 CA 2691512 A1 CA2691512 A1 CA 2691512A1 CA 002691512 A CA002691512 A CA 002691512A CA 2691512 A CA2691512 A CA 2691512A CA 2691512 A1 CA2691512 A1 CA 2691512A1

Authority

CA

Canada

Prior art keywords

indole

pyrimidin

carboxamide

methyl

chloro

Prior art date

2007-08-10

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

• Espacenet
• Global Dossier
• CIPO
• Discuss

• -1 Heteroaryl amide Chemical class 0.000 title claims abstract description 133
• 150000001875 compounds Chemical class 0.000 claims abstract description 267
• 102100037602 P2X purinoceptor 7 Human genes 0.000 claims abstract description 138
• 101710189965 P2X purinoceptor 7 Proteins 0.000 claims abstract description 137
• 208000002193 Pain Diseases 0.000 claims abstract description 89
• 230000036407 pain Effects 0.000 claims abstract description 81
• 238000000034 method Methods 0.000 claims abstract description 58
• 239000000556 agonist Substances 0.000 claims abstract description 27
• 238000011282 treatment Methods 0.000 claims abstract description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
• 206010061218 Inflammation Diseases 0.000 claims abstract description 19
• 230000004054 inflammatory process Effects 0.000 claims abstract description 19
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 8
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 8
• 208000022873 Ocular disease Diseases 0.000 claims abstract description 7
• 208000012902 Nervous system disease Diseases 0.000 claims abstract description 5
• 208000026278 immune system disease Diseases 0.000 claims abstract description 5
• 230000000926 neurological effect Effects 0.000 claims abstract 4
• 239000000203 mixture Substances 0.000 claims description 91
• 150000003839 salts Chemical class 0.000 claims description 81
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 72
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 70
• 230000000694 effects Effects 0.000 claims description 67
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 66
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 51
• 238000003556 assay Methods 0.000 claims description 47
• 229910052736 halogen Inorganic materials 0.000 claims description 47
• 150000002367 halogens Chemical class 0.000 claims description 46
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 45
• 125000001424 substituent group Chemical group 0.000 claims description 41
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• 210000004027 cell Anatomy 0.000 claims description 36
• 125000001072 heteroaryl group Chemical group 0.000 claims description 36
• 125000000623 heterocyclic group Chemical group 0.000 claims description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims description 35
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 34
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 32
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 31
• 125000004429 atom Chemical group 0.000 claims description 31
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 28
• 208000004296 neuralgia Diseases 0.000 claims description 25
• 125000003118 aryl group Chemical group 0.000 claims description 24
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 21
• 239000003814 drug Substances 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 20
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
• 125000004043 oxo group Chemical group O=* 0.000 claims description 18
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
• 150000001721 carbon Chemical group 0.000 claims description 15
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 14
• 125000002947 alkylene group Chemical group 0.000 claims description 14
• 238000000338 in vitro Methods 0.000 claims description 14
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 14
• 206010016654 Fibrosis Diseases 0.000 claims description 12
• 208000006673 asthma Diseases 0.000 claims description 12
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 208000021722 neuropathic pain Diseases 0.000 claims description 11
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
• 206010029240 Neuritis Diseases 0.000 claims description 10
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 9
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
• 230000001154 acute effect Effects 0.000 claims description 8
• 208000024827 Alzheimer disease Diseases 0.000 claims description 7
• 241000282414 Homo sapiens Species 0.000 claims description 7
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 208000014674 injury Diseases 0.000 claims description 7
• 201000008482 osteoarthritis Diseases 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 239000000126 substance Substances 0.000 claims description 7
• 238000006467 substitution reaction Methods 0.000 claims description 7
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
• 208000023275 Autoimmune disease Diseases 0.000 claims description 6
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 6
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 6
• 125000002837 carbocyclic group Chemical group 0.000 claims description 6
• 210000003169 central nervous system Anatomy 0.000 claims description 6
• 239000006071 cream Substances 0.000 claims description 6
• 238000000099 in vitro assay Methods 0.000 claims description 6
• 210000005036 nerve Anatomy 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 210000003994 retinal ganglion cell Anatomy 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 208000030886 Traumatic Brain injury Diseases 0.000 claims description 5
• 125000004423 acyloxy group Chemical group 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 230000034994 death Effects 0.000 claims description 5
• 239000007788 liquid Substances 0.000 claims description 5
• 206010025135 lupus erythematosus Diseases 0.000 claims description 5
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
• 208000011580 syndromic disease Diseases 0.000 claims description 5
• 230000009529 traumatic brain injury Effects 0.000 claims description 5
• 208000008035 Back Pain Diseases 0.000 claims description 4
• 208000023890 Complex Regional Pain Syndromes Diseases 0.000 claims description 4
• 208000010412 Glaucoma Diseases 0.000 claims description 4
• 201000005569 Gout Diseases 0.000 claims description 4
• 206010023230 Joint stiffness Diseases 0.000 claims description 4
• 206010039710 Scleroderma Diseases 0.000 claims description 4
• 230000008484 agonism Effects 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 206010003246 arthritis Diseases 0.000 claims description 4
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 4
• 230000007882 cirrhosis Effects 0.000 claims description 4
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 4
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 4
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 229910052721 tungsten Inorganic materials 0.000 claims description 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
• ATWCIOGPHPGOGT-UHFFFAOYSA-N 2-(1-adamantyl)-n-(4-chloro-1-pyrimidin-2-ylindol-3-yl)acetamide Chemical compound C1=C(NC(=O)CC23CC4CC(CC(C4)C2)C3)C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 ATWCIOGPHPGOGT-UHFFFAOYSA-N 0.000 claims description 3
• VEEYSQAYZKOZIT-UHFFFAOYSA-N 4-chloro-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 VEEYSQAYZKOZIT-UHFFFAOYSA-N 0.000 claims description 3
• 206010019233 Headaches Diseases 0.000 claims description 3
• 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 3
• 229910006074 SO2NH2 Inorganic materials 0.000 claims description 3
• 229910006069 SO3H Inorganic materials 0.000 claims description 3
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
• 239000000443 aerosol Substances 0.000 claims description 3
• 239000002775 capsule Substances 0.000 claims description 3
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
• 125000003106 haloaryl group Chemical group 0.000 claims description 3
• 231100000869 headache Toxicity 0.000 claims description 3
• ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 claims description 3
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 230000008653 root damage Effects 0.000 claims description 3
• 238000001356 surgical procedure Methods 0.000 claims description 3
• 239000006188 syrup Substances 0.000 claims description 3
• 235000020357 syrup Nutrition 0.000 claims description 3
• 150000003536 tetrazoles Chemical class 0.000 claims description 3
• 230000008733 trauma Effects 0.000 claims description 3
• FPHOPYWEFQYZLM-UHFFFAOYSA-N 1-[(1-methylimidazol-2-yl)methyl]-n-[(1-pyridin-3-ylcyclohexyl)methyl]indole-2-carboxamide Chemical compound CN1C=CN=C1CN1C2=CC=CC=C2C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 FPHOPYWEFQYZLM-UHFFFAOYSA-N 0.000 claims description 2
• ANAIABPQJGVDQA-UHFFFAOYSA-N 4-chloro-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=2C(Cl)=CC=NC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 ANAIABPQJGVDQA-UHFFFAOYSA-N 0.000 claims description 2
• 206010002383 Angina Pectoris Diseases 0.000 claims description 2
• 206010068065 Burning mouth syndrome Diseases 0.000 claims description 2
• 206010058019 Cancer Pain Diseases 0.000 claims description 2
• 208000001387 Causalgia Diseases 0.000 claims description 2
• 206010014020 Ear pain Diseases 0.000 claims description 2
• 206010015958 Eye pain Diseases 0.000 claims description 2
• 206010016059 Facial pain Diseases 0.000 claims description 2
• 208000033830 Hot Flashes Diseases 0.000 claims description 2
• 206010060800 Hot flush Diseases 0.000 claims description 2
• 208000029462 Immunodeficiency disease Diseases 0.000 claims description 2
• 208000000112 Myalgia Diseases 0.000 claims description 2
• 206010049002 Scar pain Diseases 0.000 claims description 2
• 206010072005 Spinal pain Diseases 0.000 claims description 2
• 206010042496 Sunburn Diseases 0.000 claims description 2
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
• 230000008485 antagonism Effects 0.000 claims description 2
• 208000003295 carpal tunnel syndrome Diseases 0.000 claims description 2
• 208000014439 complex regional pain syndrome type 2 Diseases 0.000 claims description 2
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
• 230000001747 exhibiting effect Effects 0.000 claims description 2
• 208000004967 femoral neuropathy Diseases 0.000 claims description 2
• 239000012530 fluid Substances 0.000 claims description 2
• 125000005059 halophenyl group Chemical group 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 208000032184 meralgia paresthetica Diseases 0.000 claims description 2
• 125000002757 morpholinyl group Chemical group 0.000 claims description 2
• 208000013465 muscle pain Diseases 0.000 claims description 2
• JZYSYXDHRXPHKQ-UHFFFAOYSA-N n-(1-adamantylmethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)C(C1=CC=CC=C11)=CN1C1=NC=CC=N1 JZYSYXDHRXPHKQ-UHFFFAOYSA-N 0.000 claims description 2
• YJCCGSIXSDHVLI-UHFFFAOYSA-N n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-yl-4-(trifluoromethyl)indole-3-carboxamide Chemical compound C1=2C(C(F)(F)F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 YJCCGSIXSDHVLI-UHFFFAOYSA-N 0.000 claims description 2
• 230000008764 nerve damage Effects 0.000 claims description 2
• 201000009985 neuronitis Diseases 0.000 claims description 2
• 150000002825 nitriles Chemical group 0.000 claims description 2
• 239000006187 pill Substances 0.000 claims description 2
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
• 239000002435 venom Substances 0.000 claims description 2
• 210000001048 venom Anatomy 0.000 claims description 2
• 231100000611 venom Toxicity 0.000 claims description 2
• 208000009935 visceral pain Diseases 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• TZKDHXJYDQGLFK-UHFFFAOYSA-N 4-chloro-n-[2-(3,4-difluorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(F)C(F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 TZKDHXJYDQGLFK-UHFFFAOYSA-N 0.000 claims 2
• LKMRWAUYFFIPLS-UHFFFAOYSA-N 1-(3-cyanopyridin-2-yl)-4-methyl-n-(2-morpholin-4-yl-2-phenylethyl)indole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2C(=CC=CN=2)C#N)C=C1C(=O)NCC(C=1C=CC=CC=1)N1CCOCC1 LKMRWAUYFFIPLS-UHFFFAOYSA-N 0.000 claims 1
• JCSUYDVTWQJBCI-UHFFFAOYSA-N 1-(3-ethylpyrazin-2-yl)-n-[(1-pyridin-3-ylcyclohexyl)methyl]indole-3-carboxamide Chemical compound CCC1=NC=CN=C1N1C2=CC=CC=C2C(C(=O)NCC2(CCCCC2)C=2C=NC=CC=2)=C1 JCSUYDVTWQJBCI-UHFFFAOYSA-N 0.000 claims 1
• DVQJAIGHURJMKU-UHFFFAOYSA-N 1-(5-fluoropyrimidin-2-yl)-n-[(1-pyridin-3-ylcyclohexyl)methyl]indole-3-carboxamide Chemical compound N1=CC(F)=CN=C1N1C2=CC=CC=C2C(C(=O)NCC2(CCCCC2)C=2C=NC=CC=2)=C1 DVQJAIGHURJMKU-UHFFFAOYSA-N 0.000 claims 1
• FLPKUPFRCHXLDY-UHFFFAOYSA-N 1-pyrimidin-2-yl-n-[[1-[4-(trifluoromethyl)phenyl]cyclohexyl]methyl]indole-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 FLPKUPFRCHXLDY-UHFFFAOYSA-N 0.000 claims 1
• GGNNKOPRPONVQA-UHFFFAOYSA-N 1-pyrimidin-2-ylindole-3,4-dicarboxylic acid Chemical compound C12=CC=CC(C(O)=O)=C2C(C(=O)O)=CN1C1=NC=CC=N1 GGNNKOPRPONVQA-UHFFFAOYSA-N 0.000 claims 1
• STSVLKXCUGQLSX-UHFFFAOYSA-N 2-[3-(1-adamantylmethylcarbamoyl)indol-1-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1N1C2=CC=CC=C2C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 STSVLKXCUGQLSX-UHFFFAOYSA-N 0.000 claims 1
• RVHSUIQQODJJDG-UHFFFAOYSA-N 2-[3-(1-adamantylmethylcarbamoyl)indol-1-yl]pentanoic acid Chemical compound C12=CC=CC=C2N(C(C(O)=O)CCC)C=C1C(=O)NCC1(C2)CC(C3)CC2CC3C1 RVHSUIQQODJJDG-UHFFFAOYSA-N 0.000 claims 1
• LCLKNJIWBCOANV-UHFFFAOYSA-N 3-chloro-1-[(1-methylimidazol-2-yl)methyl]-n-(4-methyl-2-pyridin-3-ylpentyl)indole-2-carboxamide Chemical compound C=1C=CN=CC=1C(CC(C)C)CNC(=O)C1=C(Cl)C2=CC=CC=C2N1CC1=NC=CN1C LCLKNJIWBCOANV-UHFFFAOYSA-N 0.000 claims 1
• YZFMHZXAUUEHDM-UHFFFAOYSA-N 3-chloro-n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-1-[(1-methylimidazol-2-yl)methyl]indole-2-carboxamide Chemical compound CN1C=CN=C1CN1C2=CC=CC=C2C(Cl)=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCCCC1 YZFMHZXAUUEHDM-UHFFFAOYSA-N 0.000 claims 1
• QYDVTNYUERGOIZ-UHFFFAOYSA-N 3-chloro-n-[[4-(4-chlorophenyl)oxan-4-yl]methyl]-1-[(1-methylimidazol-2-yl)methyl]indole-2-carboxamide Chemical compound CN1C=CN=C1CN1C2=CC=CC=C2C(Cl)=C1C(=O)NCC1(C=2C=CC(Cl)=CC=2)CCOCC1 QYDVTNYUERGOIZ-UHFFFAOYSA-N 0.000 claims 1
• GHPANTLFSOVSKV-UHFFFAOYSA-N 4-bromo-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Br)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 GHPANTLFSOVSKV-UHFFFAOYSA-N 0.000 claims 1
• SZMUXKSFYOVBLZ-UHFFFAOYSA-N 4-chloro-1-[2-(dimethylamino)ethyl]-n-(4-methyl-2-pyridin-3-ylpentyl)indole-3-carboxamide Chemical compound C=1N(CCN(C)C)C2=CC=CC(Cl)=C2C=1C(=O)NCC(CC(C)C)C1=CC=CN=C1 SZMUXKSFYOVBLZ-UHFFFAOYSA-N 0.000 claims 1
• KCGVNAOUYOFNIB-UHFFFAOYSA-N 4-chloro-1-[3-(dimethylamino)propyl]-n-(4-methyl-2-pyridin-3-ylpentyl)indole-3-carboxamide Chemical compound C=1N(CCCN(C)C)C2=CC=CC(Cl)=C2C=1C(=O)NCC(CC(C)C)C1=CC=CN=C1 KCGVNAOUYOFNIB-UHFFFAOYSA-N 0.000 claims 1
• FTKQORPRCLRPNX-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-yl-n-(3,3,5-trimethylcyclohexyl)indole-3-carboxamide Chemical compound C1C(C)(C)CC(C)CC1NC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FTKQORPRCLRPNX-UHFFFAOYSA-N 0.000 claims 1
• XUTHDCGXPKNBGI-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-yl-n-[[1-[4-(trifluoromethyl)phenyl]cyclohexyl]methyl]indole-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 XUTHDCGXPKNBGI-UHFFFAOYSA-N 0.000 claims 1
• GBQVSGPQEXAYLT-VMBOVVBDSA-N 4-chloro-N-[[(1R)-6,6-dimethyl-2-bicyclo[3.1.1]heptanyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C([C@]1(C2(C)C)[H])C2CCC1CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 GBQVSGPQEXAYLT-VMBOVVBDSA-N 0.000 claims 1
• LRSPAPPWXYSXKT-UHFFFAOYSA-N 4-chloro-n-(2,3-diphenylpropyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)CC1=CC=CC=C1 LRSPAPPWXYSXKT-UHFFFAOYSA-N 0.000 claims 1
• WSPSZBVPJYACII-UHFFFAOYSA-N 4-chloro-n-(2-cyclohexyl-2-phenylethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)C1CCCCC1 WSPSZBVPJYACII-UHFFFAOYSA-N 0.000 claims 1
• YTJSTQCNEZOXLZ-UHFFFAOYSA-N 4-chloro-n-(2-morpholin-4-yl-2-phenylethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)N1CCOCC1 YTJSTQCNEZOXLZ-UHFFFAOYSA-N 0.000 claims 1
• WXIVLUUFVMVXNN-UHFFFAOYSA-N 4-chloro-n-(2-morpholin-4-yl-2-phenylethyl)-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=2C(Cl)=CC=NC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)N1CCOCC1 WXIVLUUFVMVXNN-UHFFFAOYSA-N 0.000 claims 1
• QKSVJBHORLUNPE-UHFFFAOYSA-N 4-chloro-n-(2-phenylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CC=CC=1C(CCC)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 QKSVJBHORLUNPE-UHFFFAOYSA-N 0.000 claims 1
• RGVNVQZTKWHPNU-UHFFFAOYSA-N 4-chloro-n-(3-cyclopentyl-2-phenylpropyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)CC1CCCC1 RGVNVQZTKWHPNU-UHFFFAOYSA-N 0.000 claims 1
• NQIVGAXWGWVAGP-UHFFFAOYSA-N 4-chloro-n-(3-methylbutyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C12=CC=CC(Cl)=C2C(C(=O)NCCC(C)C)=CN1C1=NC=CC=N1 NQIVGAXWGWVAGP-UHFFFAOYSA-N 0.000 claims 1
• JNXFOEOZSYOZCN-UHFFFAOYSA-N 4-chloro-n-(3-phenylbutyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CC=CC=1C(C)CCNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 JNXFOEOZSYOZCN-UHFFFAOYSA-N 0.000 claims 1
• OYPGSBLIRKBVFP-UHFFFAOYSA-N 4-chloro-n-(4-methyl-2-phenylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CC=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 OYPGSBLIRKBVFP-UHFFFAOYSA-N 0.000 claims 1
• KQVGATDURWAKBQ-UHFFFAOYSA-N 4-chloro-n-(4-methyl-2-pyridin-3-ylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CN=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 KQVGATDURWAKBQ-UHFFFAOYSA-N 0.000 claims 1
• KRFPMTFREZYDKB-UHFFFAOYSA-N 4-chloro-n-(4-methyl-2-pyridin-3-ylpentyl)-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CN=C11)=CN1C1=NC=CC=N1 KRFPMTFREZYDKB-UHFFFAOYSA-N 0.000 claims 1
• YPHBXMYPYMXXKK-UHFFFAOYSA-N 4-chloro-n-(4-phenylbutyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCCCCC1=CC=CC=C1 YPHBXMYPYMXXKK-UHFFFAOYSA-N 0.000 claims 1
• QNCAVWZEJVXGSL-UHFFFAOYSA-N 4-chloro-n-(cycloheptylmethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1CCCCCC1 QNCAVWZEJVXGSL-UHFFFAOYSA-N 0.000 claims 1
• IXEUUUTXRDEESS-UHFFFAOYSA-N 4-chloro-n-[(1-hydroxycycloheptyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(Cl)=C2C=1C(=O)NCC1(O)CCCCCC1 IXEUUUTXRDEESS-UHFFFAOYSA-N 0.000 claims 1
• NCQCHKXQFNBEPU-UHFFFAOYSA-N 4-chloro-n-[(1-hydroxycycloheptyl)methyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=NC=CC(Cl)=C2C=1C(=O)NCC1(O)CCCCCC1 NCQCHKXQFNBEPU-UHFFFAOYSA-N 0.000 claims 1
• QHXNCWYVURIMHA-UHFFFAOYSA-N 4-chloro-n-[(1-hydroxycyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(Cl)=C2C=1C(=O)NCC1(O)CCCCC1 QHXNCWYVURIMHA-UHFFFAOYSA-N 0.000 claims 1
• JAXLKCRYONSHKK-UHFFFAOYSA-N 4-chloro-n-[(1-hydroxycyclohexyl)methyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=NC=CC(Cl)=C2C=1C(=O)NCC1(O)CCCCC1 JAXLKCRYONSHKK-UHFFFAOYSA-N 0.000 claims 1
• MJSYWSCNWAHYJT-UHFFFAOYSA-N 4-chloro-n-[(1-hydroxycyclopentyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(Cl)=C2C=1C(=O)NCC1(O)CCCC1 MJSYWSCNWAHYJT-UHFFFAOYSA-N 0.000 claims 1
• NDLYAXIBRQFGQO-UHFFFAOYSA-N 4-chloro-n-[(4-hydroxythian-4-yl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(Cl)=C2C=1C(=O)NCC1(O)CCSCC1 NDLYAXIBRQFGQO-UHFFFAOYSA-N 0.000 claims 1
• HUMJOZFHUVTLGE-UHFFFAOYSA-N 4-chloro-n-[2-(2,4-difluorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound FC1=CC(F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 HUMJOZFHUVTLGE-UHFFFAOYSA-N 0.000 claims 1
• WSZARDIHNUIOKO-UHFFFAOYSA-N 4-chloro-n-[2-(3,4-difluorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C(F)C(F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CN=C11)=CN1C1=NC=CC=N1 WSZARDIHNUIOKO-UHFFFAOYSA-N 0.000 claims 1
• PTDLAPWZPSAZJT-UHFFFAOYSA-N 4-chloro-n-[2-(4-chloro-3-fluorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(Cl)C(F)=CC(C(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)N2CCCCC2)=C1 PTDLAPWZPSAZJT-UHFFFAOYSA-N 0.000 claims 1
• ZHQIUAHDKPUOKT-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCOCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 ZHQIUAHDKPUOKT-UHFFFAOYSA-N 0.000 claims 1
• XKBDSAHQQPZOGB-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCOCC1)CNC(=O)C(C1=C(Cl)C=CN=C11)=CN1C1=NC=CC=N1 XKBDSAHQQPZOGB-UHFFFAOYSA-N 0.000 claims 1
• VZMLUTLVCOGUEI-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-2-piperazin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCNCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 VZMLUTLVCOGUEI-UHFFFAOYSA-N 0.000 claims 1
• JFUGGKDZPSAIOY-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 JFUGGKDZPSAIOY-UHFFFAOYSA-N 0.000 claims 1
• HFOVPPMTYJOFMT-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CN=C11)=CN1C1=NC=CC=N1 HFOVPPMTYJOFMT-UHFFFAOYSA-N 0.000 claims 1
• ADFDHZKHHVMNEO-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-4-methylpentyl]-1-[2-(dimethylamino)ethyl]indole-3-carboxamide Chemical compound C=1N(CCN(C)C)C2=CC=CC(Cl)=C2C=1C(=O)NCC(CC(C)C)C1=CC=C(Cl)C=C1 ADFDHZKHHVMNEO-UHFFFAOYSA-N 0.000 claims 1
• MWHKATVDYBPMRL-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-4-methylpentyl]-1-[3-(dimethylamino)propyl]indole-3-carboxamide Chemical compound C=1N(CCCN(C)C)C2=CC=CC(Cl)=C2C=1C(=O)NCC(CC(C)C)C1=CC=C(Cl)C=C1 MWHKATVDYBPMRL-UHFFFAOYSA-N 0.000 claims 1
• LYJDGLXLBJVRCJ-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-4-methylpentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 LYJDGLXLBJVRCJ-UHFFFAOYSA-N 0.000 claims 1
• FSSJSUBFNKMDTL-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CCC)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FSSJSUBFNKMDTL-UHFFFAOYSA-N 0.000 claims 1
• OTOKCOMTTJYKQA-UHFFFAOYSA-N 4-chloro-n-[2-(4-fluorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 OTOKCOMTTJYKQA-UHFFFAOYSA-N 0.000 claims 1
• YCOBLIXIJZXBLR-UHFFFAOYSA-N 4-chloro-n-[2-(6-methoxypyridin-3-yl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=NC(OC)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 YCOBLIXIJZXBLR-UHFFFAOYSA-N 0.000 claims 1
• IUCVSEOIXFTRMF-UHFFFAOYSA-N 4-chloro-n-[2-piperidin-1-yl-2-[4-(trifluoromethyl)phenyl]ethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 IUCVSEOIXFTRMF-UHFFFAOYSA-N 0.000 claims 1
• APXFQTNXUQJHBO-UHFFFAOYSA-N 4-chloro-n-[2-piperidin-1-yl-2-[6-(trifluoromethyl)pyridin-3-yl]ethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=NC(C(F)(F)F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 APXFQTNXUQJHBO-UHFFFAOYSA-N 0.000 claims 1
• FKCPUVYYGVELQN-UHFFFAOYSA-N 4-chloro-n-[4-methyl-2-(4-methylphenyl)pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FKCPUVYYGVELQN-UHFFFAOYSA-N 0.000 claims 1
• FAURIVHGMPPVLE-UHFFFAOYSA-N 4-chloro-n-[4-methyl-2-[4-(trifluoromethyl)phenyl]pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FAURIVHGMPPVLE-UHFFFAOYSA-N 0.000 claims 1
• RUEJAIZHINZZDH-SUMWQHHRSA-N 4-chloro-n-[[(1s,2r)-2-hydroxycyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound O[C@@H]1CCCC[C@H]1CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 RUEJAIZHINZZDH-SUMWQHHRSA-N 0.000 claims 1
• KAENIFYSTKFXFA-UHFFFAOYSA-N 4-chloro-n-[[1-(4-chlorophenyl)cyclobutyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCC1 KAENIFYSTKFXFA-UHFFFAOYSA-N 0.000 claims 1
• OXHUCARSSRATMO-UHFFFAOYSA-N 4-chloro-n-[[1-(4-chlorophenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 OXHUCARSSRATMO-UHFFFAOYSA-N 0.000 claims 1
• DERUNCJUFQBRRW-UHFFFAOYSA-N 4-chloro-n-[[1-(4-methoxyphenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 DERUNCJUFQBRRW-UHFFFAOYSA-N 0.000 claims 1
• GDLABCVOIPYOGZ-UHFFFAOYSA-N 4-chloro-n-[[1-(4-methylpiperazin-1-yl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1CN(C)CCN1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 GDLABCVOIPYOGZ-UHFFFAOYSA-N 0.000 claims 1
• PIODEHXTCAOMMR-UHFFFAOYSA-N 4-chloro-n-[[4-(4-chlorophenyl)oxan-4-yl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCOCC1 PIODEHXTCAOMMR-UHFFFAOYSA-N 0.000 claims 1
• RRTLCYYRRUBNTG-UHFFFAOYSA-N 4-chloro-n-[[4-(4-chlorophenyl)oxan-4-yl]methyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CN=C3N(C=3N=CC=CN=3)C=2)CCOCC1 RRTLCYYRRUBNTG-UHFFFAOYSA-N 0.000 claims 1
• PDAPGQZQFOLEID-UHFFFAOYSA-N 4-cyano-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(C#N)=C2C=1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 PDAPGQZQFOLEID-UHFFFAOYSA-N 0.000 claims 1
• SPIDLTVGBQEWBZ-UHFFFAOYSA-N 4-fluoro-n-(4-methyl-2-pyridin-3-ylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CN=CC=1C(CC(C)C)CNC(=O)C(C1=C(F)C=CC=C11)=CN1C1=NC=CC=N1 SPIDLTVGBQEWBZ-UHFFFAOYSA-N 0.000 claims 1
• AHBGYVPATHFLKO-UHFFFAOYSA-N 4-fluoro-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 AHBGYVPATHFLKO-UHFFFAOYSA-N 0.000 claims 1
• QBYJBBMCFSHBTP-UHFFFAOYSA-N 4-fluoro-n-[2-(6-methoxypyridin-3-yl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=NC(OC)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(F)C=CC=C11)=CN1C1=NC=CC=N1 QBYJBBMCFSHBTP-UHFFFAOYSA-N 0.000 claims 1
• MYTXBBJPZVAHBU-UHFFFAOYSA-N 4-fluoro-n-[4-methyl-2-(4-methylphenyl)pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(F)C=CC=C11)=CN1C1=NC=CC=N1 MYTXBBJPZVAHBU-UHFFFAOYSA-N 0.000 claims 1
• GEJZOVZEMUQBQK-UHFFFAOYSA-N 4-fluoro-n-[4-methyl-2-[4-(trifluoromethyl)phenyl]pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(F)C=CC=C11)=CN1C1=NC=CC=N1 GEJZOVZEMUQBQK-UHFFFAOYSA-N 0.000 claims 1
• QJKMIQZBXGSLAK-UHFFFAOYSA-N 4-fluoro-n-[[1-(4-fluorophenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(F)=CC=C1C1(CNC(=O)C=2C3=C(F)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 QJKMIQZBXGSLAK-UHFFFAOYSA-N 0.000 claims 1
• RANXEHMUKRYIEL-UHFFFAOYSA-N 4-fluoro-n-[[1-(4-methoxyphenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1(CNC(=O)C=2C3=C(F)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 RANXEHMUKRYIEL-UHFFFAOYSA-N 0.000 claims 1
• GUCURJGUSGPXIC-UHFFFAOYSA-N 4-fluoro-n-[[1-(4-methylphenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(C)=CC=C1C1(CNC(=O)C=2C3=C(F)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 GUCURJGUSGPXIC-UHFFFAOYSA-N 0.000 claims 1
• SCBJKZLZBBFRSW-UHFFFAOYSA-N 4-methyl-n-(2-morpholin-4-yl-2-phenylethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)N1CCOCC1 SCBJKZLZBBFRSW-UHFFFAOYSA-N 0.000 claims 1
• FGRZUIMQKHWIGY-UHFFFAOYSA-N 4-methyl-n-(4-methyl-2-morpholin-4-ylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1COCCN1C(CC(C)C)CNC(=O)C(C1=C(C)C=CC=C11)=CN1C1=NC=CC=N1 FGRZUIMQKHWIGY-UHFFFAOYSA-N 0.000 claims 1
• JVYOELCASNKUKK-UHFFFAOYSA-N 4-methyl-n-(4-methyl-2-pyridin-3-ylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CN=CC=1C(CC(C)C)CNC(=O)C(C1=C(C)C=CC=C11)=CN1C1=NC=CC=N1 JVYOELCASNKUKK-UHFFFAOYSA-N 0.000 claims 1
• OIKQYDBRBPIGDB-UHFFFAOYSA-N 4-methyl-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 OIKQYDBRBPIGDB-UHFFFAOYSA-N 0.000 claims 1
• GPRICYCQYFLCSD-UHFFFAOYSA-N 7-chloro-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2C(C(=O)NCC2(CCCCC2)C=2C=NC=CC=2)=CN1C1=NC=CC=N1 GPRICYCQYFLCSD-UHFFFAOYSA-N 0.000 claims 1
• 229910018828 PO3H2 Inorganic materials 0.000 claims 1
• LTRXFYKSRHNZMG-UHFFFAOYSA-N methyl 2-[3-[(1-pyridin-3-ylcyclohexyl)methylcarbamoyl]indol-1-yl]pyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CN=C1N1C2=CC=CC=C2C(C(=O)NCC2(CCCCC2)C=2C=NC=CC=2)=C1 LTRXFYKSRHNZMG-UHFFFAOYSA-N 0.000 claims 1
• UUCNBNVIKYMGID-UHFFFAOYSA-N n-(1-adamantylmethyl)-4-chloro-1-[2-(dimethylamino)ethyl]indole-3-carboxamide Chemical compound C12=C(Cl)C=CC=C2N(CCN(C)C)C=C1C(=O)NCC1(C2)CC(C3)CC2CC3C1 UUCNBNVIKYMGID-UHFFFAOYSA-N 0.000 claims 1
• PFXSYZMQBXGURF-UHFFFAOYSA-N n-(1-adamantylmethyl)-4-chloro-1-[3-(dimethylamino)propyl]indole-3-carboxamide Chemical compound C12=C(Cl)C=CC=C2N(CCCN(C)C)C=C1C(=O)NCC1(C2)CC(C3)CC2CC3C1 PFXSYZMQBXGURF-UHFFFAOYSA-N 0.000 claims 1
• AFWMMWSWXVYLDZ-UHFFFAOYSA-N n-(1-adamantylmethyl)-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 AFWMMWSWXVYLDZ-UHFFFAOYSA-N 0.000 claims 1
• NCRXZRNQZWAQQE-UHFFFAOYSA-N n-(1-adamantylmethyl)-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C=2C(C)=CC=CC=2N1C1=NC=CC=N1 NCRXZRNQZWAQQE-UHFFFAOYSA-N 0.000 claims 1
• GXQNBGUOACJYPR-UHFFFAOYSA-N n-(2-adamantyl)-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(C(=O)NC2C3CC4CC(C3)CC2C4)C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 GXQNBGUOACJYPR-UHFFFAOYSA-N 0.000 claims 1
• TZMRUUUUXCOCJO-UHFFFAOYSA-N n-(4-methyl-2-phenylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CC=CC=1C(CC(C)C)CNC(=O)C(C1=CC=CC=C11)=CN1C1=NC=CC=N1 TZMRUUUUXCOCJO-UHFFFAOYSA-N 0.000 claims 1
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