KR20100076022A - Ａｌｋ 억제제로서 유용한 이미다조 [１,２-ａ] 피리딘 유도체 - Google Patents
Ａｌｋ 억제제로서 유용한 이미다조 [１,２-ａ] 피리딘 유도체 Download PDFInfo
- Publication number
- KR20100076022A KR20100076022A KR1020107010615A KR20107010615A KR20100076022A KR 20100076022 A KR20100076022 A KR 20100076022A KR 1020107010615 A KR1020107010615 A KR 1020107010615A KR 20107010615 A KR20107010615 A KR 20107010615A KR 20100076022 A KR20100076022 A KR 20100076022A
- Authority
- KR
- South Korea
- Prior art keywords
- pyridin
- imidazo
- alkyl
- phenyl
- pyridine
- 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.)
- Withdrawn
Links
- 239000003112 inhibitor Substances 0.000 title description 8
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 171
- 238000000034 method Methods 0.000 claims abstract description 48
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 36
- 238000011282 treatment Methods 0.000 claims abstract description 29
- 208000002815 pulmonary hypertension Diseases 0.000 claims abstract description 21
- 201000010099 disease Diseases 0.000 claims abstract description 20
- 208000005069 pulmonary fibrosis Diseases 0.000 claims abstract description 18
- 208000019425 cirrhosis of liver Diseases 0.000 claims abstract description 15
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 13
- 102100034134 Activin receptor type-1B Human genes 0.000 claims abstract description 12
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 11
- 101000712674 Homo sapiens TGF-beta receptor type-1 Proteins 0.000 claims abstract description 9
- 230000001404 mediated effect Effects 0.000 claims abstract description 9
- 101710173011 Activin receptor type-1B Proteins 0.000 claims abstract description 8
- 102100033456 TGF-beta receptor type-1 Human genes 0.000 claims abstract description 8
- 201000011510 cancer Diseases 0.000 claims abstract description 8
- 208000029578 Muscle disease Diseases 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- -1 carboxy, carbonyl Chemical group 0.000 claims description 132
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 59
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 239000003814 drug Substances 0.000 claims description 25
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 230000005764 inhibitory process Effects 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 206010016654 Fibrosis Diseases 0.000 claims description 13
- 210000000988 bone and bone Anatomy 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 12
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 230000004761 fibrosis Effects 0.000 claims description 11
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims description 6
- 208000020084 Bone disease Diseases 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 150000008064 anhydrides Chemical group 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 208000017169 kidney disease Diseases 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 6
- 150000003462 sulfoxides Chemical class 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- 206010006956 Calcium deficiency Diseases 0.000 claims description 5
- 230000001154 acute effect Effects 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 230000001771 impaired effect Effects 0.000 claims description 5
- 230000011164 ossification Effects 0.000 claims description 5
- 208000037803 restenosis Diseases 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 230000029663 wound healing Effects 0.000 claims description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 4
- 206010051246 Photodermatosis Diseases 0.000 claims description 4
- 208000025865 Ulcer Diseases 0.000 claims description 4
- 208000027418 Wounds and injury Diseases 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 208000020832 chronic kidney disease Diseases 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 4
- 230000006870 function Effects 0.000 claims description 4
- 230000008845 photoaging Effects 0.000 claims description 4
- 230000037390 scarring Effects 0.000 claims description 4
- 238000007920 subcutaneous administration Methods 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 231100000397 ulcer Toxicity 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 206010052428 Wound Diseases 0.000 claims description 3
- 206010003246 arthritis Diseases 0.000 claims description 3
- 208000006454 hepatitis Diseases 0.000 claims description 3
- 231100000283 hepatitis Toxicity 0.000 claims description 3
- 210000000653 nervous system Anatomy 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 2
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims description 2
- 201000009273 Endometriosis Diseases 0.000 claims description 2
- 208000018565 Hemochromatosis Diseases 0.000 claims description 2
- 208000002260 Keloid Diseases 0.000 claims description 2
- 206010027398 Mesenteric fibrosis Diseases 0.000 claims description 2
- 208000022873 Ocular disease Diseases 0.000 claims description 2
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 2
- 230000002159 abnormal effect Effects 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 230000004221 bone function Effects 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 2
- 208000002672 hepatitis B Diseases 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 210000001117 keloid Anatomy 0.000 claims description 2
- 201000002793 renal fibrosis Diseases 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 210000000574 retroperitoneal space Anatomy 0.000 claims 1
- 150000003839 salts Chemical group 0.000 abstract description 26
- 108020003175 receptors Proteins 0.000 abstract description 25
- 208000035475 disorder Diseases 0.000 abstract description 14
- 206010028289 Muscle atrophy Diseases 0.000 abstract description 13
- 230000002757 inflammatory effect Effects 0.000 abstract description 12
- 208000023504 respiratory system disease Diseases 0.000 abstract description 12
- 230000000414 obstructive effect Effects 0.000 abstract description 11
- 239000012453 solvate Chemical group 0.000 abstract description 11
- 201000000585 muscular atrophy Diseases 0.000 abstract description 7
- 230000020763 muscle atrophy Effects 0.000 abstract description 6
- 230000009885 systemic effect Effects 0.000 abstract description 3
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 260
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 186
- 239000000543 intermediate Substances 0.000 description 120
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 107
- 239000011541 reaction mixture Substances 0.000 description 74
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 67
- 235000019439 ethyl acetate Nutrition 0.000 description 51
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
- 239000000203 mixture Substances 0.000 description 43
- 239000007787 solid Substances 0.000 description 41
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 36
- 238000003818 flash chromatography Methods 0.000 description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 101800002279 Transforming growth factor beta-1 Proteins 0.000 description 31
- 102000046299 Transforming Growth Factor beta1 Human genes 0.000 description 30
- 102000004887 Transforming Growth Factor beta Human genes 0.000 description 29
- 108090001012 Transforming Growth Factor beta Proteins 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000003795 chemical substances by application Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- 239000012267 brine Substances 0.000 description 25
- 239000011734 sodium Substances 0.000 description 25
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
- 102000005962 receptors Human genes 0.000 description 24
- 239000012298 atmosphere Substances 0.000 description 21
- 239000000377 silicon dioxide Substances 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
- 229910052786 argon Inorganic materials 0.000 description 18
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
- 229940079593 drug Drugs 0.000 description 16
- 230000011664 signaling Effects 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 108010056852 Myostatin Proteins 0.000 description 14
- 208000006673 asthma Diseases 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- CYEFKCRAAGLNHW-UHFFFAOYSA-N furan-3-ylboronic acid Chemical compound OB(O)C=1C=COC=1 CYEFKCRAAGLNHW-UHFFFAOYSA-N 0.000 description 14
- 102100039939 Growth/differentiation factor 8 Human genes 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 13
- 230000014509 gene expression Effects 0.000 description 13
- 108010059616 Activins Proteins 0.000 description 12
- 102000005606 Activins Human genes 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000488 activin Substances 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 210000004072 lung Anatomy 0.000 description 11
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 10
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 9
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 108091000080 Phosphotransferase Proteins 0.000 description 9
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- 108010023082 activin A Proteins 0.000 description 9
- 102000020233 phosphotransferase Human genes 0.000 description 9
- 230000002685 pulmonary effect Effects 0.000 description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 210000002744 extracellular matrix Anatomy 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 208000004248 Familial Primary Pulmonary Hypertension Diseases 0.000 description 7
- 101150003085 Pdcl gene Proteins 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000000443 aerosol Substances 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 230000001684 chronic effect Effects 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- JLIHQPWLAOYTRH-UHFFFAOYSA-N (3-chloropyridin-4-yl)boronic acid Chemical compound OB(O)C1=CC=NC=C1Cl JLIHQPWLAOYTRH-UHFFFAOYSA-N 0.000 description 6
- LZAXVCBLZXZVCK-UHFFFAOYSA-N 3-bromo-6-iodoimidazo[1,2-a]pyridine Chemical compound C1=CC(I)=CN2C(Br)=CN=C21 LZAXVCBLZXZVCK-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 description 6
- 208000019693 Lung disease Diseases 0.000 description 6
- 108090000445 Parathyroid hormone Proteins 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 230000018109 developmental process Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 230000003176 fibrotic effect Effects 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 6
- 208000036971 interstitial lung disease 2 Diseases 0.000 description 6
- 201000008312 primary pulmonary hypertension Diseases 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000002560 therapeutic procedure Methods 0.000 description 6
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 5
- WBPVNANQXSFZES-UHFFFAOYSA-N 3-[(3-bromoimidazo[1,2-a]pyridin-6-yl)amino]cyclohexan-1-ol Chemical compound C1C(O)CCCC1NC1=CN2C(Br)=CN=C2C=C1 WBPVNANQXSFZES-UHFFFAOYSA-N 0.000 description 5
- LBPZKTZBYAXZDD-UHFFFAOYSA-N 3-bromo-7-chloroimidazo[1,2-a]pyridine Chemical compound C1=C(Cl)C=CN2C(Br)=CN=C21 LBPZKTZBYAXZDD-UHFFFAOYSA-N 0.000 description 5
- HNKZXMBWWOIUMV-UHFFFAOYSA-N 7-chloro-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C=1N=C2C=C(Cl)C=CN2C=1C(C=1)=CC=NC=1C1=CC=CC=C1 HNKZXMBWWOIUMV-UHFFFAOYSA-N 0.000 description 5
- 206010006895 Cachexia Diseases 0.000 description 5
- 241000725303 Human immunodeficiency virus Species 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 208000029523 Interstitial Lung disease Diseases 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229940124630 bronchodilator Drugs 0.000 description 5
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 5
- 230000004069 differentiation Effects 0.000 description 5
- 210000002950 fibroblast Anatomy 0.000 description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 5
- 210000002540 macrophage Anatomy 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- NMBKAXJHGMDYGA-UHFFFAOYSA-N (3-pyrazol-1-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(N2N=CC=C2)=C1 NMBKAXJHGMDYGA-UHFFFAOYSA-N 0.000 description 4
- OMCJIJONZGFQKQ-UHFFFAOYSA-N 3-(2-phenylpyridin-4-yl)-7-piperidin-4-ylimidazo[1,2-a]pyridine Chemical compound C1CNCCC1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 OMCJIJONZGFQKQ-UHFFFAOYSA-N 0.000 description 4
- JNQNLGHSMCNDQR-UHFFFAOYSA-N 3-[(3-bromoimidazo[1,2-a]pyridin-6-yl)amino]-1-methylcyclohexan-1-ol Chemical compound C1C(C)(O)CCCC1NC1=CN2C(Br)=CN=C2C=C1 JNQNLGHSMCNDQR-UHFFFAOYSA-N 0.000 description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 4
- YOPGDKBHRQNZPB-UHFFFAOYSA-N 7-chloro-3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridine Chemical compound C=1N=C2C=C(Cl)C=CN2C=1C(C=1)=CC=CC=1N1C=CC=N1 YOPGDKBHRQNZPB-UHFFFAOYSA-N 0.000 description 4
- 102100039705 Beta-2 adrenergic receptor Human genes 0.000 description 4
- 108010006654 Bleomycin Proteins 0.000 description 4
- 206010010904 Convulsion Diseases 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 101000799189 Homo sapiens Activin receptor type-1B Proteins 0.000 description 4
- 102100025748 Mothers against decapentaplegic homolog 3 Human genes 0.000 description 4
- 101710143111 Mothers against decapentaplegic homolog 3 Proteins 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- FYFFPNFUVMBPRZ-UHFFFAOYSA-N [3-(methylcarbamoyl)phenyl]boronic acid Chemical compound CNC(=O)C1=CC=CC(B(O)O)=C1 FYFFPNFUVMBPRZ-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 239000000048 adrenergic agonist Substances 0.000 description 4
- 229940126157 adrenergic receptor agonist Drugs 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 239000012131 assay buffer Substances 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 description 4
- 229960001561 bleomycin Drugs 0.000 description 4
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 229940031098 ethanolamine Drugs 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 210000003205 muscle Anatomy 0.000 description 4
- QBINDBBHLSZZSA-UHFFFAOYSA-N n-(2-hydroxyethyl)-4-[3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridin-7-yl]benzamide Chemical compound C1=CC(C(=O)NCCO)=CC=C1C1=CC2=NC=C(C=3C=C(C=CC=3)N3N=CC=C3)N2C=C1 QBINDBBHLSZZSA-UHFFFAOYSA-N 0.000 description 4
- UMFJAHHVKNCGLG-UHFFFAOYSA-N n-Nitrosodimethylamine Chemical compound CN(C)N=O UMFJAHHVKNCGLG-UHFFFAOYSA-N 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 210000003491 skin Anatomy 0.000 description 4
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- 238000000844 transformation Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- XUYJXHGMSITXMW-VGOFRKELSA-N (1r,3r)-1-methyl-3-[[3-(2-pyrazol-1-ylpyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1[C@](C)(O)CCC[C@H]1NC1=CN2C(C=3C=C(N=CC=3)N3N=CC=C3)=CN=C2C=C1 XUYJXHGMSITXMW-VGOFRKELSA-N 0.000 description 3
- WJYRVVDXJMJLTN-UHFFFAOYSA-N (2-chloropyridin-4-yl)boronic acid Chemical compound OB(O)C1=CC=NC(Cl)=C1 WJYRVVDXJMJLTN-UHFFFAOYSA-N 0.000 description 3
- UWFSVMGORORBJS-UHFFFAOYSA-N 1-ethyl-5-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]pyridin-2-one Chemical compound C1=CC(=O)N(CC)C=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 UWFSVMGORORBJS-UHFFFAOYSA-N 0.000 description 3
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
- OREHQDRYMUUZGL-UHFFFAOYSA-N 3,6-dibromoimidazo[1,2-a]pyridine Chemical compound C1=CC(Br)=CN2C(Br)=CN=C21 OREHQDRYMUUZGL-UHFFFAOYSA-N 0.000 description 3
- KSNFDYZQAVMKTF-UHFFFAOYSA-N 3-(2-phenylpyridin-4-yl)-7-(1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1NCCC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 KSNFDYZQAVMKTF-UHFFFAOYSA-N 0.000 description 3
- WTZPVIPUVFBXET-UHFFFAOYSA-N 3-(2-phenylpyridin-4-yl)-7-(1-propan-2-ylpiperidin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1CN(C(C)C)CCC1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 WTZPVIPUVFBXET-UHFFFAOYSA-N 0.000 description 3
- DDNHLSZIAFNIIT-UHFFFAOYSA-N 3-(3-bromoimidazo[1,2-a]pyridin-7-yl)-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(Br)N3C=C2)=C1 DDNHLSZIAFNIIT-UHFFFAOYSA-N 0.000 description 3
- XSWYKZKYSWIXOA-UHFFFAOYSA-N 3-(3-pyrazol-1-ylphenyl)-7-pyridin-3-ylimidazo[1,2-a]pyridine Chemical compound C1=CC=NN1C1=CC=CC(C=2N3C=CC(=CC3=NC=2)C=2C=NC=CC=2)=C1 XSWYKZKYSWIXOA-UHFFFAOYSA-N 0.000 description 3
- KYAILCUUOVDDJA-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)pyridin-4-yl]-7-[3-(3-piperidin-1-ylpropoxy)phenyl]imidazo[1,2-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C=2C=C(OCCCN3CCCCC3)C=CC=2)=CC=N1 KYAILCUUOVDDJA-UHFFFAOYSA-N 0.000 description 3
- CNDJZKKIPNNHFS-UHFFFAOYSA-N 3-[3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridin-7-yl]benzaldehyde Chemical compound O=CC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)N2N=CC=C2)=C1 CNDJZKKIPNNHFS-UHFFFAOYSA-N 0.000 description 3
- MVMTZLAQSBDSRC-UHFFFAOYSA-N 3-[7-(6-morpholin-4-ylpyridin-3-yl)imidazo[1,2-a]pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N3C=CC(=CC3=NC=2)C=2C=NC(=CC=2)N2CCOCC2)=C1 MVMTZLAQSBDSRC-UHFFFAOYSA-N 0.000 description 3
- LIBKDAUSMLPFBF-UHFFFAOYSA-N 3-bromo-6-chloroimidazo[1,2-a]pyridine Chemical compound C1=C(Cl)C=CC2=NC=C(Br)N21 LIBKDAUSMLPFBF-UHFFFAOYSA-N 0.000 description 3
- XTDPPFGDGUGSGA-UHFFFAOYSA-N 4-[(3-bromoimidazo[1,2-a]pyridin-6-yl)amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=CN2C(Br)=CN=C2C=C1 XTDPPFGDGUGSGA-UHFFFAOYSA-N 0.000 description 3
- CHQLEOMNCPWPRC-UHFFFAOYSA-N 4-[[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 CHQLEOMNCPWPRC-UHFFFAOYSA-N 0.000 description 3
- RFSJDVRUOHUYCX-UHFFFAOYSA-N 5-[3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridin-7-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)N2N=CC=C2)=C1 RFSJDVRUOHUYCX-UHFFFAOYSA-N 0.000 description 3
- KSHASNSKOUFBAT-UHFFFAOYSA-N 5-[3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridin-7-yl]pyridine-3-carboxamide Chemical compound NC(=O)C1=CN=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)N2N=CC=C2)=C1 KSHASNSKOUFBAT-UHFFFAOYSA-N 0.000 description 3
- BNVRJWISXVGSOF-UHFFFAOYSA-N 6-chloro-3-(2-chloropyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound N12C=C(Cl)C=CC2=NC=C1C1=CC=NC(Cl)=C1 BNVRJWISXVGSOF-UHFFFAOYSA-N 0.000 description 3
- QWCLJGHFPRJARD-UHFFFAOYSA-N 6-chloro-3-(2-methoxypyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=NC(OC)=CC(C=2N3C=C(Cl)C=CC3=NC=2)=C1 QWCLJGHFPRJARD-UHFFFAOYSA-N 0.000 description 3
- REYUNQXPGLPNQI-UHFFFAOYSA-N 6-chloro-4-(7-chloroimidazo[1,2-a]pyridin-3-yl)-n-methylpyridin-2-amine Chemical compound ClC1=NC(NC)=CC(C=2N3C=CC(Cl)=CC3=NC=2)=C1 REYUNQXPGLPNQI-UHFFFAOYSA-N 0.000 description 3
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 3
- SFNVKBMYGWLILH-UHFFFAOYSA-N 7-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]-3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridine Chemical compound C1CN(C)CCN1CC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)N2N=CC=C2)=C1 SFNVKBMYGWLILH-UHFFFAOYSA-N 0.000 description 3
- RWBWPIJHHBXAIO-UHFFFAOYSA-N 7-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1CN(C)CCN1C1=CC=C(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)C=N1 RWBWPIJHHBXAIO-UHFFFAOYSA-N 0.000 description 3
- OASOJRLJBDCVNU-UHFFFAOYSA-N 7-bromoimidazo[1,2-a]pyridine Chemical compound C1=C(Br)C=CN2C=CN=C21 OASOJRLJBDCVNU-UHFFFAOYSA-N 0.000 description 3
- YTTTUJHRYHKUHM-UHFFFAOYSA-N 7-chloro-3-(2,6-dichloropyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C=1N=C2C=C(Cl)C=CN2C=1C1=CC(Cl)=NC(Cl)=C1 YTTTUJHRYHKUHM-UHFFFAOYSA-N 0.000 description 3
- FFUSKIVGRCEUAS-UHFFFAOYSA-N 7-chloro-3-[2-(3-chlorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound ClC1=CC=CC(C=2N=CC=C(C=2)C=2N3C=CC(Cl)=CC3=NC=2)=C1 FFUSKIVGRCEUAS-UHFFFAOYSA-N 0.000 description 3
- NGHRUBVFDAKWBC-UHFFFAOYSA-N 7-chloroimidazo[1,2-a]pyridine Chemical compound C1=C(Cl)C=CN2C=CN=C21 NGHRUBVFDAKWBC-UHFFFAOYSA-N 0.000 description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 3
- 206010003694 Atrophy Diseases 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 102000016970 Follistatin Human genes 0.000 description 3
- 108010014612 Follistatin Proteins 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 101000817629 Homo sapiens Dymeclin Proteins 0.000 description 3
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 3
- 208000029725 Metabolic bone disease Diseases 0.000 description 3
- 102100025751 Mothers against decapentaplegic homolog 2 Human genes 0.000 description 3
- 101710143123 Mothers against decapentaplegic homolog 2 Proteins 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 3
- 206010047924 Wheezing Diseases 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 230000003143 atherosclerotic effect Effects 0.000 description 3
- 230000037444 atrophy Effects 0.000 description 3
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 206010006451 bronchitis Diseases 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 239000005018 casein Substances 0.000 description 3
- 235000021240 caseins Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000003821 enantio-separation Methods 0.000 description 3
- HTGQHSAGPJOMSY-UHFFFAOYSA-N ethyl 3-[3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridin-7-yl]benzoate Chemical compound CCOC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)N2N=CC=C2)=C1 HTGQHSAGPJOMSY-UHFFFAOYSA-N 0.000 description 3
- FVXCHVGOHRLDQM-UHFFFAOYSA-N ethyl 4-[3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridin-7-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=CC2=NC=C(C=3C=C(C=CC=3)N3N=CC=C3)N2C=C1 FVXCHVGOHRLDQM-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 3
- 210000003734 kidney Anatomy 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- SNOAMCGRBIQLTR-UHFFFAOYSA-N n-(2-hydroxyethyl)-3-[3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridin-7-yl]benzamide Chemical compound OCCNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)N2N=CC=C2)=C1 SNOAMCGRBIQLTR-UHFFFAOYSA-N 0.000 description 3
- QFQQUNQDMKEYCL-UHFFFAOYSA-N n-methyl-3-[3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridin-7-yl]benzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)N2N=CC=C2)=C1 QFQQUNQDMKEYCL-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 230000002018 overexpression Effects 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 230000000069 prophylactic effect Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 208000001076 sarcopenia Diseases 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 208000037812 secondary pulmonary hypertension Diseases 0.000 description 3
- 235000004400 serine Nutrition 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 3
- GVWLDFUJNNNLLY-WZONZLPQSA-N (1r,3r)-3-[[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]-1-methylcyclohexan-1-ol Chemical compound C1[C@](C)(O)CCC[C@H]1NC1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 GVWLDFUJNNNLLY-WZONZLPQSA-N 0.000 description 2
- JBCNIEFZSUHIIV-UHFFFAOYSA-N (2-carbamoyl-3-methylphenyl)boronic acid Chemical compound CC1=CC=CC(B(O)O)=C1C(N)=O JBCNIEFZSUHIIV-UHFFFAOYSA-N 0.000 description 2
- DGVCWROXCNSYFO-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]phenyl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)C=C1 DGVCWROXCNSYFO-UHFFFAOYSA-N 0.000 description 2
- 0 *c1cnc2[n]1ccc(*)c2 Chemical compound *c1cnc2[n]1ccc(*)c2 0.000 description 2
- OBOBUDMMFXRNDO-UHFFFAOYSA-N 1-(3-chloropropyl)piperidine;hydron;chloride Chemical compound Cl.ClCCCN1CCCCC1 OBOBUDMMFXRNDO-UHFFFAOYSA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- HGMHJUKRKRGBRP-UHFFFAOYSA-N 1-[(3-bromoimidazo[1,2-a]pyridin-6-yl)amino]cyclohexan-1-ol Chemical compound C1=CC2=NC=C(Br)N2C=C1NC1(O)CCCCC1 HGMHJUKRKRGBRP-UHFFFAOYSA-N 0.000 description 2
- BUVSVPLXSSIZRA-UHFFFAOYSA-N 1-[4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 BUVSVPLXSSIZRA-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- XUYJXHGMSITXMW-UHFFFAOYSA-N 1-methyl-3-[[3-(2-pyrazol-1-ylpyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1C(C)(O)CCCC1NC1=CN2C(C=3C=C(N=CC=3)N3N=CC=C3)=CN=C2C=C1 XUYJXHGMSITXMW-UHFFFAOYSA-N 0.000 description 2
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
- BBDOZQNKVYEOKW-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-n-[[3-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]ethanamine Chemical compound C1CN(C)CCN1CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 BBDOZQNKVYEOKW-UHFFFAOYSA-N 0.000 description 2
- DITFOHYODMIVSH-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-n-[[4-[3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]ethanamine Chemical compound C1CN(C)CCN1CCNCC1=CC=C(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)N2N=CC=C2)C=C1 DITFOHYODMIVSH-UHFFFAOYSA-N 0.000 description 2
- NZQDWKCNBOELAI-KSFYIVLOSA-N 2-[(3s,4r)-3-benzyl-4-hydroxy-3,4-dihydro-2h-chromen-7-yl]-4-(trifluoromethyl)benzoic acid Chemical compound C([C@@H]1[C@H](C2=CC=C(C=C2OC1)C=1C(=CC=C(C=1)C(F)(F)F)C(O)=O)O)C1=CC=CC=C1 NZQDWKCNBOELAI-KSFYIVLOSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- ITXMPLOYLYOSDQ-UHFFFAOYSA-N 3,6-bis(2-methoxypyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=NC(OC)=CC(C=2N3C=C(C=CC3=NC=2)C=2C=C(OC)N=CC=2)=C1 ITXMPLOYLYOSDQ-UHFFFAOYSA-N 0.000 description 2
- DKNSWWCQKLUHPM-UHFFFAOYSA-N 3-(2-chloro-1h-pyridin-2-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine Chemical compound N12C=C(C(F)(F)F)C=CC2=NC=C1C1(Cl)NC=CC=C1 DKNSWWCQKLUHPM-UHFFFAOYSA-N 0.000 description 2
- SCYXGFXNSHBYTR-UHFFFAOYSA-N 3-(2-phenylpyridin-4-yl)-7-(1-propan-2-yl-3,6-dihydro-2h-pyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1N(C(C)C)CCC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 SCYXGFXNSHBYTR-UHFFFAOYSA-N 0.000 description 2
- HWDCLIIVIUMNKR-UHFFFAOYSA-N 3-(2-phenylpyridin-4-yl)-7-pyridin-3-ylimidazo[1,2-a]pyridine Chemical compound C=1N=C2C=C(C=3C=NC=CC=3)C=CN2C=1C(C=1)=CC=NC=1C1=CC=CC=C1 HWDCLIIVIUMNKR-UHFFFAOYSA-N 0.000 description 2
- DWNIIZJASKEMIA-UHFFFAOYSA-N 3-(2-phenylpyridin-4-yl)-7-pyridin-4-ylimidazo[1,2-a]pyridine Chemical compound C=1N=C2C=C(C=3C=CN=CC=3)C=CN2C=1C(C=1)=CC=NC=1C1=CC=CC=C1 DWNIIZJASKEMIA-UHFFFAOYSA-N 0.000 description 2
- RQVHCOMMSKNVDP-UHFFFAOYSA-N 3-(3-pyrazol-1-ylphenyl)-7-pyridin-4-ylimidazo[1,2-a]pyridine Chemical compound C1=CC=NN1C1=CC=CC(C=2N3C=CC(=CC3=NC=2)C=2C=CN=CC=2)=C1 RQVHCOMMSKNVDP-UHFFFAOYSA-N 0.000 description 2
- GICZEAPYVZCPEK-UHFFFAOYSA-N 3-(7-chloroimidazo[1,2-a]pyridin-3-yl)benzamide Chemical compound NC(=O)C1=CC=CC(C=2N3C=CC(Cl)=CC3=NC=2)=C1 GICZEAPYVZCPEK-UHFFFAOYSA-N 0.000 description 2
- UTHGJLRMQDTUGV-UHFFFAOYSA-N 3-[2-(3-fluorophenyl)pyridin-4-yl]-7-(6-methylpyridin-3-yl)imidazo[1,2-a]pyridine Chemical compound C1=NC(C)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=C(F)C=CC=3)N2C=C1 UTHGJLRMQDTUGV-UHFFFAOYSA-N 0.000 description 2
- UDLLNNQPHAAELB-UHFFFAOYSA-N 3-[2-(3-fluorophenyl)pyridin-4-yl]-7-pyridin-3-ylimidazo[1,2-a]pyridine Chemical compound FC1=CC=CC(C=2N=CC=C(C=2)C=2N3C=CC(=CC3=NC=2)C=2C=NC=CC=2)=C1 UDLLNNQPHAAELB-UHFFFAOYSA-N 0.000 description 2
- ONAPXBZCEITGJL-UHFFFAOYSA-N 3-[2-(furan-3-yl)pyridin-4-yl]-6-(1-methylpyrazol-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=NN(C)C=C1C1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 ONAPXBZCEITGJL-UHFFFAOYSA-N 0.000 description 2
- RKIKHQXDVKMWQB-UHFFFAOYSA-N 3-[2-(furan-3-yl)pyridin-4-yl]-6-(2-methoxypyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=NC(OC)=CC(C2=CN3C(C=4C=C(N=CC=4)C4=COC=C4)=CN=C3C=C2)=C1 RKIKHQXDVKMWQB-UHFFFAOYSA-N 0.000 description 2
- QMPLTHGJWUJLJJ-UHFFFAOYSA-N 3-[2-(furan-3-yl)pyridin-4-yl]-6-(3-methoxyphenyl)imidazo[1,2-a]pyridine Chemical compound COC1=CC=CC(C2=CN3C(C=4C=C(N=CC=4)C4=COC=C4)=CN=C3C=C2)=C1 QMPLTHGJWUJLJJ-UHFFFAOYSA-N 0.000 description 2
- ZDPTXOZFGDAOOM-UHFFFAOYSA-N 3-[2-(furan-3-yl)pyridin-4-yl]-6-(4-methoxyphenyl)imidazo[1,2-a]pyridine Chemical compound C1=CC(OC)=CC=C1C1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 ZDPTXOZFGDAOOM-UHFFFAOYSA-N 0.000 description 2
- GJHXYWNIRNREOD-UHFFFAOYSA-N 3-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]-1H-pyridin-2-one Chemical compound OC1=NC=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 GJHXYWNIRNREOD-UHFFFAOYSA-N 0.000 description 2
- GMLMBMBXVSAYOL-UHFFFAOYSA-N 3-[3-[2-(3-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=C(F)C=CC=2)=C1 GMLMBMBXVSAYOL-UHFFFAOYSA-N 0.000 description 2
- PGRRYYHOVNFJHX-UHFFFAOYSA-N 3-[3-[2-(3-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]aniline Chemical compound NC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=C(F)C=CC=2)=C1 PGRRYYHOVNFJHX-UHFFFAOYSA-N 0.000 description 2
- OHLXKVCLVZBTPP-UHFFFAOYSA-N 3-[3-[2-(4-fluorophenyl)-6-(methylamino)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-n-methylbenzamide Chemical class CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=C(NC)C=2)C=2C=CC(F)=CC=2)=C1 OHLXKVCLVZBTPP-UHFFFAOYSA-N 0.000 description 2
- JLVPBQIAPYFGAC-UHFFFAOYSA-N 3-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenol Chemical compound OC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC(F)=CC=2)=C1 JLVPBQIAPYFGAC-UHFFFAOYSA-N 0.000 description 2
- OPKCZRAYCLWVEU-UHFFFAOYSA-N 3-[3-[2-phenyl-6-(propan-2-ylamino)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]benzaldehyde Chemical compound N=1C(NC(C)C)=CC(C=2N3C=CC(=CC3=NC=2)C=2C=C(C=O)C=CC=2)=CC=1C1=CC=CC=C1 OPKCZRAYCLWVEU-UHFFFAOYSA-N 0.000 description 2
- RHAQAVPOOZZHDJ-UHFFFAOYSA-N 3-[7-(3-hydroxyphenyl)imidazo[1,2-a]pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N3C=CC(=CC3=NC=2)C=2C=C(O)C=CC=2)=C1 RHAQAVPOOZZHDJ-UHFFFAOYSA-N 0.000 description 2
- HHHPYCAVWQYDJK-UHFFFAOYSA-N 3-[[3-[2-fluoro-6-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1C(O)CCCC1NC1=CN2C(C=3C=C(N=C(F)C=3)C3=COC=C3)=CN=C2C=C1 HHHPYCAVWQYDJK-UHFFFAOYSA-N 0.000 description 2
- YZGMUNVIHIZITF-UHFFFAOYSA-N 3-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine Chemical compound C1=C(C(F)(F)F)C=CC2=NC=C(Br)N21 YZGMUNVIHIZITF-UHFFFAOYSA-N 0.000 description 2
- PZDFGIYFIUAIOM-UHFFFAOYSA-N 3-imidazo[1,2-a]pyridin-7-yl-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=CN3C=C2)=C1 PZDFGIYFIUAIOM-UHFFFAOYSA-N 0.000 description 2
- OUJPGYOTVDKOGN-UHFFFAOYSA-N 4-(7-chloroimidazo[1,2-a]pyridin-3-yl)-6-(4-fluorophenyl)-n-methylpyridin-2-amine Chemical compound N=1C(NC)=CC(C=2N3C=CC(Cl)=CC3=NC=2)=CC=1C1=CC=C(F)C=C1 OUJPGYOTVDKOGN-UHFFFAOYSA-N 0.000 description 2
- NAWHNDWHVOWPAS-UHFFFAOYSA-N 4-(7-chloroimidazo[1,2-a]pyridin-3-yl)-n-methyl-6-phenylpyridin-2-amine Chemical compound N=1C(NC)=CC(C=2N3C=CC(Cl)=CC3=NC=2)=CC=1C1=CC=CC=C1 NAWHNDWHVOWPAS-UHFFFAOYSA-N 0.000 description 2
- YTOXNKCDJJPUGE-UHFFFAOYSA-N 4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 YTOXNKCDJJPUGE-UHFFFAOYSA-N 0.000 description 2
- MFBOLOYMMAVPPT-UHFFFAOYSA-N 4-[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 MFBOLOYMMAVPPT-UHFFFAOYSA-N 0.000 description 2
- QGNMKAFZXNOYJF-UHFFFAOYSA-N 4-[5-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]pyridin-2-yl]morpholine Chemical compound C1COCCN1C1=CC=C(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)C=N1 QGNMKAFZXNOYJF-UHFFFAOYSA-N 0.000 description 2
- VMRORBHGSJMDJM-UHFFFAOYSA-N 4-[5-[3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridin-7-yl]pyridin-2-yl]morpholine Chemical compound C1COCCN1C1=CC=C(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)N2N=CC=C2)C=N1 VMRORBHGSJMDJM-UHFFFAOYSA-N 0.000 description 2
- XYOABBMZYFBKRI-UHFFFAOYSA-N 4-[[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=CN2C(C=3C=C(N=CC=3)C=3C=CC=CC=3)=CN=C2C=C1 XYOABBMZYFBKRI-UHFFFAOYSA-N 0.000 description 2
- RAMGGTDXKUSFLB-UHFFFAOYSA-N 4-[[3-[2-(1h-pyrazol-5-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=CN2C(C=3C=C(N=CC=3)C3=NNC=C3)=CN=C2C=C1 RAMGGTDXKUSFLB-UHFFFAOYSA-N 0.000 description 2
- DCPKCDDLCUOUGI-UHFFFAOYSA-N 4-[[3-[2-(furan-2-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=CN2C(C=3C=C(N=CC=3)C=3OC=CC=3)=CN=C2C=C1 DCPKCDDLCUOUGI-UHFFFAOYSA-N 0.000 description 2
- QVPYUPQESMTLMX-UHFFFAOYSA-N 4-[[3-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]morpholine Chemical compound C=1C=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=CC=1CN1CCOCC1 QVPYUPQESMTLMX-UHFFFAOYSA-N 0.000 description 2
- ZKQQCQIPBBWDJZ-UHFFFAOYSA-N 4-[[4-[3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]morpholine Chemical compound C=1C=C(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)N2N=CC=C2)C=CC=1CN1CCOCC1 ZKQQCQIPBBWDJZ-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- PYXNITNKYBLBMW-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyrazole Chemical compound FC(F)(F)C1=CC=NN1 PYXNITNKYBLBMW-UHFFFAOYSA-N 0.000 description 2
- PJSSOUGFGYCPMA-UHFFFAOYSA-N 5-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]-1H-pyridin-2-one Chemical compound N1C(=O)C=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 PJSSOUGFGYCPMA-UHFFFAOYSA-N 0.000 description 2
- RPSYDUMFOMMGBT-UHFFFAOYSA-N 5-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]pyridine-3-carboxamide Chemical compound NC(=O)C1=CN=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 RPSYDUMFOMMGBT-UHFFFAOYSA-N 0.000 description 2
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 2
- QPSZJYZDJVGYPS-UHFFFAOYSA-N 6-(furan-3-yl)-3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound O1C=CC(C2=CN3C(C=4C=C(N=CC=4)C4=COC=C4)=CN=C3C=C2)=C1 QPSZJYZDJVGYPS-UHFFFAOYSA-N 0.000 description 2
- NQIVIKBUQJRSQP-UHFFFAOYSA-N 6-(trifluoromethyl)imidazo[1,2-a]pyridine Chemical compound C1=C(C(F)(F)F)C=CC2=NC=CN21 NQIVIKBUQJRSQP-UHFFFAOYSA-N 0.000 description 2
- FXPMFQUOGYGTAM-UHFFFAOYSA-N 6-bromoimidazo[1,2-a]pyridine Chemical compound C1=C(Br)C=CC2=NC=CN21 FXPMFQUOGYGTAM-UHFFFAOYSA-N 0.000 description 2
- XQEGYCZJSVFGEE-UHFFFAOYSA-N 6-chloroimidazo[1,2-a]pyridine Chemical compound C1=C(Cl)C=CC2=NC=CN21 XQEGYCZJSVFGEE-UHFFFAOYSA-N 0.000 description 2
- ZYXOOFUOEJPQKM-UHFFFAOYSA-N 6-iodoimidazo[1,2-a]pyridine Chemical compound C1=C(I)C=CC2=NC=CN21 ZYXOOFUOEJPQKM-UHFFFAOYSA-N 0.000 description 2
- ZNJIJPPINRBBRZ-UHFFFAOYSA-N 6-phenyl-4-(7-phenylimidazo[1,2-a]pyridin-3-yl)-n-propan-2-ylpyridin-2-amine Chemical compound N=1C(NC(C)C)=CC(C=2N3C=CC(=CC3=NC=2)C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 ZNJIJPPINRBBRZ-UHFFFAOYSA-N 0.000 description 2
- LMHSLTBASZNODR-UHFFFAOYSA-N 7-(2-methoxypyridin-3-yl)-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound COC1=NC=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 LMHSLTBASZNODR-UHFFFAOYSA-N 0.000 description 2
- BNSHFBAIEGHUAB-UHFFFAOYSA-N 7-(6-ethoxypyridin-3-yl)-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=NC(OCC)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 BNSHFBAIEGHUAB-UHFFFAOYSA-N 0.000 description 2
- RQYSJGZTDHZIKQ-UHFFFAOYSA-N 7-(6-methylpyridin-3-yl)-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=NC(C)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 RQYSJGZTDHZIKQ-UHFFFAOYSA-N 0.000 description 2
- RHNAHAKMJJYDPG-UHFFFAOYSA-N 7-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1CN(C)CCN1CC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 RHNAHAKMJJYDPG-UHFFFAOYSA-N 0.000 description 2
- JHMXPLDVKMIEBX-UHFFFAOYSA-N 7-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridine Chemical compound C1CN(C)CCN1CC1=CC=C(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)N2N=CC=C2)C=C1 JHMXPLDVKMIEBX-UHFFFAOYSA-N 0.000 description 2
- SWXXYWZPUFZUMB-UHFFFAOYSA-N 7-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridine Chemical compound C1CN(C)CCN1C1=CC=C(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)N2N=CC=C2)C=N1 SWXXYWZPUFZUMB-UHFFFAOYSA-N 0.000 description 2
- YXPLXQTUGJCUCL-UHFFFAOYSA-N 7-chloro-3-(2-chloropyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C=1N=C2C=C(Cl)C=CN2C=1C1=CC=NC(Cl)=C1 YXPLXQTUGJCUCL-UHFFFAOYSA-N 0.000 description 2
- DOVNWSNCECLXMK-UHFFFAOYSA-N 7-chloro-3-[2-(2,4-difluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound FC1=CC(F)=CC=C1C1=CC(C=2N3C=CC(Cl)=CC3=NC=2)=CC=N1 DOVNWSNCECLXMK-UHFFFAOYSA-N 0.000 description 2
- CTXIEQYJIOMFKK-UHFFFAOYSA-N 7-chloro-3-[2-(2-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound FC1=CC=CC=C1C1=CC(C=2N3C=CC(Cl)=CC3=NC=2)=CC=N1 CTXIEQYJIOMFKK-UHFFFAOYSA-N 0.000 description 2
- FMGJTGGYBXFCTQ-UHFFFAOYSA-N 7-chloro-3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=CC(C=2N3C=CC(Cl)=CC3=NC=2)=CC=N1 FMGJTGGYBXFCTQ-UHFFFAOYSA-N 0.000 description 2
- QZQLDJZRCBWSOW-UHFFFAOYSA-N 7-chloro-3-[3-(3-methylpyrazol-1-yl)phenyl]imidazo[1,2-a]pyridine Chemical compound N1=C(C)C=CN1C1=CC=CC(C=2N3C=CC(Cl)=CC3=NC=2)=C1 QZQLDJZRCBWSOW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 102000055006 Calcitonin Human genes 0.000 description 2
- 108060001064 Calcitonin Proteins 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 208000031229 Cardiomyopathies Diseases 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- 208000002330 Congenital Heart Defects Diseases 0.000 description 2
- 102000004127 Cytokines Human genes 0.000 description 2
- 108090000695 Cytokines Proteins 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 102000016359 Fibronectins Human genes 0.000 description 2
- 108010067306 Fibronectins Proteins 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241000711549 Hepacivirus C Species 0.000 description 2
- 241000700721 Hepatitis B virus Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 206010023421 Kidney fibrosis Diseases 0.000 description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
- 206010067125 Liver injury Diseases 0.000 description 2
- 208000004852 Lung Injury Diseases 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 206010027476 Metastases Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000699660 Mus musculus Species 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 206010049088 Osteopenia Diseases 0.000 description 2
- 102000003982 Parathyroid hormone Human genes 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 108010022233 Plasminogen Activator Inhibitor 1 Proteins 0.000 description 2
- 102000012335 Plasminogen Activator Inhibitor 1 Human genes 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
- 208000002200 Respiratory Hypersensitivity Diseases 0.000 description 2
- 208000037656 Respiratory Sounds Diseases 0.000 description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000007107 Stomach Ulcer Diseases 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 2
- 239000004473 Threonine Substances 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- PCBOWMZAEDDKNH-HOTGVXAUSA-N [4-(trifluoromethoxy)phenyl]methyl (3as,6as)-2-(3-fluoro-4-sulfamoylbenzoyl)-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1=C(F)C(S(=O)(=O)N)=CC=C1C(=O)N1C[C@H]2CN(C(=O)OCC=3C=CC(OC(F)(F)F)=CC=3)C[C@@H]2C1 PCBOWMZAEDDKNH-HOTGVXAUSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 230000010085 airway hyperresponsiveness Effects 0.000 description 2
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 208000033571 alveolar capillary dysplasia with misalignment of pulmonary veins Diseases 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 238000011914 asymmetric synthesis Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 210000000013 bile duct Anatomy 0.000 description 2
- 210000002805 bone matrix Anatomy 0.000 description 2
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 2
- 229960004015 calcitonin Drugs 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 230000007882 cirrhosis Effects 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 208000028831 congenital heart disease Diseases 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- UZBHNSVUMGIKLU-UHFFFAOYSA-N cyclopenten-1-ylboronic acid Chemical compound OB(O)C1=CCCC1 UZBHNSVUMGIKLU-UHFFFAOYSA-N 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000003412 degenerative effect Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000002651 drug therapy Methods 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 210000002889 endothelial cell Anatomy 0.000 description 2
- 229940011871 estrogen Drugs 0.000 description 2
- 239000000262 estrogen Substances 0.000 description 2
- AQFRVPUDLSFZME-UHFFFAOYSA-N ethyl 4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 AQFRVPUDLSFZME-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 230000035876 healing Effects 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229940043355 kinase inhibitor Drugs 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 210000005265 lung cell Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000009401 metastasis Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- KTSAENKRAXJYDE-UHFFFAOYSA-N methyl 3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridine-6-carboxylate Chemical compound COC(=O)c1ccc2ncc(-c3ccnc(c3)-c3ccoc3)n2c1 KTSAENKRAXJYDE-UHFFFAOYSA-N 0.000 description 2
- UZGCHIJIFAKVNH-UHFFFAOYSA-N methyl 3-bromoimidazo[1,2-a]pyridine-6-carboxylate Chemical compound C1=C(C(=O)OC)C=CC2=NC=C(Br)N21 UZGCHIJIFAKVNH-UHFFFAOYSA-N 0.000 description 2
- BTDBMFODXFTFIL-UHFFFAOYSA-N methyl imidazo[1,2-a]pyridine-6-carboxylate Chemical compound C1=C(C(=O)OC)C=CC2=NC=CN21 BTDBMFODXFTFIL-UHFFFAOYSA-N 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000003149 muscarinic antagonist Substances 0.000 description 2
- 230000035772 mutation Effects 0.000 description 2
- 210000000651 myofibroblast Anatomy 0.000 description 2
- ZRBDHRTWJKNXAD-UHFFFAOYSA-N n',n'-dimethyl-n-[[3-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]ethane-1,2-diamine Chemical compound CN(C)CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 ZRBDHRTWJKNXAD-UHFFFAOYSA-N 0.000 description 2
- PVWJOHSYSPVVQO-UHFFFAOYSA-N n',n'-dimethyl-n-[[3-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]propane-1,3-diamine Chemical compound CN(C)CCCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 PVWJOHSYSPVVQO-UHFFFAOYSA-N 0.000 description 2
- SKZWPLZJQDUFNW-UHFFFAOYSA-N n',n'-dimethyl-n-[[4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]propane-1,3-diamine Chemical compound C1=CC(CNCCCN(C)C)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 SKZWPLZJQDUFNW-UHFFFAOYSA-N 0.000 description 2
- JVVZYBGELBFBTR-UHFFFAOYSA-N n',n'-dimethyl-n-[[4-[3-[3-(1h-pyrazol-5-yl)phenyl]imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]propane-1,3-diamine Chemical compound C1=CC(CNCCCN(C)C)=CC=C1C1=CC2=NC=C(C=3C=C(C=CC=3)C3=NNC=C3)N2C=C1 JVVZYBGELBFBTR-UHFFFAOYSA-N 0.000 description 2
- OKFDRAHPFKMAJH-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)-8-(methanesulfonamido)dibenzofuran-1-carboxamide Chemical compound C=12C3=CC(NS(=O)(=O)C)=CC=C3OC2=C(OC(F)F)C=CC=1C(=O)NC1=C(Cl)C=NC=C1Cl OKFDRAHPFKMAJH-UHFFFAOYSA-N 0.000 description 2
- YJULJQDMIBBXHD-UHFFFAOYSA-N n-(4-hydroxycyclohexyl)-4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]benzamide Chemical compound C1CC(O)CCC1NC(=O)C1=CC=C(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)C=C1 YJULJQDMIBBXHD-UHFFFAOYSA-N 0.000 description 2
- BPWDHUWOCADJQB-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-[3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridin-7-yl]benzamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1C1=CC2=NC=C(C=3C=C(C=CC=3)N3N=CC=C3)N2C=C1 BPWDHUWOCADJQB-UHFFFAOYSA-N 0.000 description 2
- BQZAOCQAFIMNOG-UHFFFAOYSA-N n-[3-[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C2=CN3C(C=4C=C(N=CC=4)C4=COC=C4)=CN=C3C=C2)=C1 BQZAOCQAFIMNOG-UHFFFAOYSA-N 0.000 description 2
- HJPCZMQSNMGMGD-UHFFFAOYSA-N n-[3-[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C2=CN3C(C=4C=C(N=CC=4)C4=COC=C4)=CN=C3C=C2)=C1 HJPCZMQSNMGMGD-UHFFFAOYSA-N 0.000 description 2
- DLIKSVCPOWLNKM-UHFFFAOYSA-N n-[[3-[3-[2-(cyclopenten-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]ethanamine Chemical compound CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2CCCC=2)=C1 DLIKSVCPOWLNKM-UHFFFAOYSA-N 0.000 description 2
- ABMJNFWTKIOZLV-UHFFFAOYSA-N n-cyclopropyl-6-phenyl-4-(7-phenylimidazo[1,2-a]pyridin-3-yl)pyridin-2-amine Chemical compound C1CC1NC1=CC(C=2N3C=CC(=CC3=NC=2)C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=N1 ABMJNFWTKIOZLV-UHFFFAOYSA-N 0.000 description 2
- ISDVKKHAISLGTH-UHFFFAOYSA-N n-methyl-3-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]benzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 ISDVKKHAISLGTH-UHFFFAOYSA-N 0.000 description 2
- YTMCFQQGTJRFMC-UHFFFAOYSA-N n-methyl-3-[3-[2-(3-methylphenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]benzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=C(C)C=CC=2)=C1 YTMCFQQGTJRFMC-UHFFFAOYSA-N 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Chemical group 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 239000000199 parathyroid hormone Substances 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 230000026731 phosphorylation Effects 0.000 description 2
- 238000006366 phosphorylation reaction Methods 0.000 description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 210000001147 pulmonary artery Anatomy 0.000 description 2
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 2
- HZFPPBMKGYINDF-UHFFFAOYSA-N pyrimidin-5-ylboronic acid Chemical compound OB(O)C1=CN=CN=C1 HZFPPBMKGYINDF-UHFFFAOYSA-N 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 238000007634 remodeling Methods 0.000 description 2
- 230000029058 respiratory gaseous exchange Effects 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 229960002052 salbutamol Drugs 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 230000036573 scar formation Effects 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229940095743 selective estrogen receptor modulator Drugs 0.000 description 2
- 239000000333 selective estrogen receptor modulator Substances 0.000 description 2
- 230000019491 signal transduction Effects 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- AWIMWKUUVKWCFC-UHFFFAOYSA-N tert-butyl 4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 AWIMWKUUVKWCFC-UHFFFAOYSA-N 0.000 description 2
- WZDGZWOAQTVYBX-XOINTXKNSA-N tibolone Chemical compound C([C@@H]12)C[C@]3(C)[C@@](C#C)(O)CC[C@H]3[C@@H]1[C@H](C)CC1=C2CCC(=O)C1 WZDGZWOAQTVYBX-XOINTXKNSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000011830 transgenic mouse model Methods 0.000 description 2
- 210000004509 vascular smooth muscle cell Anatomy 0.000 description 2
- 230000037314 wound repair Effects 0.000 description 2
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 1
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 1
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 1
- WBPVNANQXSFZES-MWLCHTKSSA-N (1r,3r)-3-[(3-bromoimidazo[1,2-a]pyridin-6-yl)amino]cyclohexan-1-ol Chemical compound C1[C@H](O)CCC[C@H]1NC1=CN2C(Br)=CN=C2C=C1 WBPVNANQXSFZES-MWLCHTKSSA-N 0.000 description 1
- POFFUZYHJYSGMG-SJLPKXTDSA-N (1r,3r)-3-[[3-(2-pyrazol-1-ylpyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1[C@H](O)CCC[C@H]1NC1=CN2C(C=3C=C(N=CC=3)N3N=CC=C3)=CN=C2C=C1 POFFUZYHJYSGMG-SJLPKXTDSA-N 0.000 description 1
- AGBBQXNHMIFXGP-IEBWSBKVSA-N (1r,3r)-3-[[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1[C@H](O)CCC[C@H]1NC1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 AGBBQXNHMIFXGP-IEBWSBKVSA-N 0.000 description 1
- XUYJXHGMSITXMW-JTSKRJEESA-N (1s,3s)-1-methyl-3-[[3-(2-pyrazol-1-ylpyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1[C@@](C)(O)CCC[C@@H]1NC1=CN2C(C=3C=C(N=CC=3)N3N=CC=C3)=CN=C2C=C1 XUYJXHGMSITXMW-JTSKRJEESA-N 0.000 description 1
- WBPVNANQXSFZES-ONGXEEELSA-N (1s,3s)-3-[(3-bromoimidazo[1,2-a]pyridin-6-yl)amino]cyclohexan-1-ol Chemical compound C1[C@@H](O)CCC[C@@H]1NC1=CN2C(Br)=CN=C2C=C1 WBPVNANQXSFZES-ONGXEEELSA-N 0.000 description 1
- POFFUZYHJYSGMG-WMZOPIPTSA-N (1s,3s)-3-[[3-(2-pyrazol-1-ylpyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1[C@@H](O)CCC[C@@H]1NC1=CN2C(C=3C=C(N=CC=3)N3N=CC=C3)=CN=C2C=C1 POFFUZYHJYSGMG-WMZOPIPTSA-N 0.000 description 1
- AGBBQXNHMIFXGP-HKUYNNGSSA-N (1s,3s)-3-[[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1[C@@H](O)CCC[C@@H]1NC1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 AGBBQXNHMIFXGP-HKUYNNGSSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- MWFBZACMGJGNLV-IBGZPJMESA-N (2s)-2-(methylamino)-1-[4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]piperidin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@H](C)NC)CCC1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 MWFBZACMGJGNLV-IBGZPJMESA-N 0.000 description 1
- CJMUIIBZOBKEGZ-UHFFFAOYSA-N (3-methoxypyridin-4-yl)boronic acid Chemical compound COC1=CN=CC=C1B(O)O CJMUIIBZOBKEGZ-UHFFFAOYSA-N 0.000 description 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- ZJLFOOWTDISDIO-ZRDIBKRKSA-N (e)-3-[6-[(2,6-dichlorophenyl)sulfanylmethyl]-3-(2-phenylethoxy)pyridin-2-yl]prop-2-enoic acid Chemical compound C=1C=C(OCCC=2C=CC=CC=2)C(/C=C/C(=O)O)=NC=1CSC1=C(Cl)C=CC=C1Cl ZJLFOOWTDISDIO-ZRDIBKRKSA-N 0.000 description 1
- PMGQWSIVQFOFOQ-BDUVBVHRSA-N (e)-but-2-enedioic acid;(2r)-2-[2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine Chemical compound OC(=O)\C=C\C(O)=O.CN1CCC[C@@H]1CCOC(C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 PMGQWSIVQFOFOQ-BDUVBVHRSA-N 0.000 description 1
- ZCZVGQCBSJLDDS-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,8-naphthyridine Chemical compound C1=CC=C2CCCNC2=N1 ZCZVGQCBSJLDDS-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- MVQUTUUMCDRVMH-UHFFFAOYSA-N 1-(2-methylpropyl)-5-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]pyridin-2-one Chemical compound C1=CC(=O)N(CC(C)C)C=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 MVQUTUUMCDRVMH-UHFFFAOYSA-N 0.000 description 1
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 description 1
- HYDNBISGGZHYPI-UHFFFAOYSA-N 1-[3-[3-[2-(2-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C(=CC=CC=2)F)=C1 HYDNBISGGZHYPI-UHFFFAOYSA-N 0.000 description 1
- WKDKJZGNICWJRH-UHFFFAOYSA-N 1-[3-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC(F)=CC=2)=C1 WKDKJZGNICWJRH-UHFFFAOYSA-N 0.000 description 1
- QXZKQPGKFOGZAR-UHFFFAOYSA-N 1-[3-[3-[2-(cyclopenten-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]-n-methylmethanamine Chemical compound CNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2CCCC=2)=C1 QXZKQPGKFOGZAR-UHFFFAOYSA-N 0.000 description 1
- CEEBYHNFQZVYBI-UHFFFAOYSA-N 1-[3-fluoro-5-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(F)=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 CEEBYHNFQZVYBI-UHFFFAOYSA-N 0.000 description 1
- PVBLJPCMWKGTOH-UHFFFAOYSA-N 1-aminocyclohexan-1-ol Chemical compound NC1(O)CCCCC1 PVBLJPCMWKGTOH-UHFFFAOYSA-N 0.000 description 1
- ZMLPCAJUCUHRRB-UHFFFAOYSA-N 1-ethyl-5-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]pyridin-2-one Chemical compound C1=CC(=O)N(CC)C=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC(F)=CC=3)N2C=C1 ZMLPCAJUCUHRRB-UHFFFAOYSA-N 0.000 description 1
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
- SVJBIDKRYHWBPB-UHFFFAOYSA-N 1-methyl-3-[[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1C(C)(O)CCCC1NC1=CN2C(C=3C=C(N=CC=3)C=3C=CC=CC=3)=CN=C2C=C1 SVJBIDKRYHWBPB-UHFFFAOYSA-N 0.000 description 1
- GOSWRADLWAGFQC-UHFFFAOYSA-N 1-methyl-3-[[3-[2-[3-(trifluoromethyl)pyrazol-1-yl]pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1C(C)(O)CCCC1NC1=CN2C(C=3C=C(N=CC=3)N3N=C(C=C3)C(F)(F)F)=CN=C2C=C1 GOSWRADLWAGFQC-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- DCYGAPKNVCQNOE-UHFFFAOYSA-N 2,2,2-triphenylacetic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)O)C1=CC=CC=C1 DCYGAPKNVCQNOE-UHFFFAOYSA-N 0.000 description 1
- PEFDHAOFDBNZEQ-UHFFFAOYSA-N 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC(Cl)=NC(Cl)=C1 PEFDHAOFDBNZEQ-UHFFFAOYSA-N 0.000 description 1
- KAXASJHTMHMQOU-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)-1-[4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]piperidin-1-yl]ethanone Chemical compound CC1=NC=CN1CC(=O)N1CCC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)CC1 KAXASJHTMHMQOU-UHFFFAOYSA-N 0.000 description 1
- GGYZNUBUAFEOFG-UHFFFAOYSA-N 2-(2-pyrazol-1-ylpyridin-4-yl)-6-pyrimidin-5-ylimidazo[1,2-a]pyridine Chemical compound C1=CC=NN1C1=CC(C=2N=C3C=CC(=CN3C=2)C=2C=NC=NC=2)=CC=N1 GGYZNUBUAFEOFG-UHFFFAOYSA-N 0.000 description 1
- WTQTVNDAXJQBJB-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 WTQTVNDAXJQBJB-UHFFFAOYSA-N 0.000 description 1
- KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 1
- ZKLPARSLTMPFCP-OAQYLSRUSA-N 2-[2-[4-[(R)-(4-chlorophenyl)-phenylmethyl]-1-piperazinyl]ethoxy]acetic acid Chemical compound C1CN(CCOCC(=O)O)CCN1[C@@H](C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-OAQYLSRUSA-N 0.000 description 1
- HIXUFDUYAGLLOF-UHFFFAOYSA-N 2-[2-fluoro-4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]phenyl]acetic acid Chemical compound C1=C(F)C(CC(=O)O)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 HIXUFDUYAGLLOF-UHFFFAOYSA-N 0.000 description 1
- VHHOFYOOLONDKI-UHFFFAOYSA-N 2-[4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 VHHOFYOOLONDKI-UHFFFAOYSA-N 0.000 description 1
- QOTJRZKTFKHNHT-UHFFFAOYSA-N 2-[4-[3-[2-(cyclopenten-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3CCCC=3)N2C=C1 QOTJRZKTFKHNHT-UHFFFAOYSA-N 0.000 description 1
- QNSTZOCPUKGXLJ-UHFFFAOYSA-N 2-[4-[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]pyrazol-1-yl]acetic acid Chemical compound C1=NN(CC(=O)O)C=C1C1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 QNSTZOCPUKGXLJ-UHFFFAOYSA-N 0.000 description 1
- XQZYHFSXJPTABF-UHFFFAOYSA-N 2-[4-[3-[2-(methylamino)-6-phenylpyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]acetic acid Chemical compound N=1C(NC)=CC(C=2N3C=CC(=CC3=NC=2)C=2C=CC(CC(O)=O)=CC=2)=CC=1C1=CC=CC=C1 XQZYHFSXJPTABF-UHFFFAOYSA-N 0.000 description 1
- RNKPPUMEMJPTMM-UHFFFAOYSA-N 2-[[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 RNKPPUMEMJPTMM-UHFFFAOYSA-N 0.000 description 1
- PQMCFTMVQORYJC-UHFFFAOYSA-N 2-aminocyclohexan-1-ol Chemical compound NC1CCCCC1O PQMCFTMVQORYJC-UHFFFAOYSA-N 0.000 description 1
- SPCKHVPPRJWQRZ-UHFFFAOYSA-N 2-benzhydryloxy-n,n-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 SPCKHVPPRJWQRZ-UHFFFAOYSA-N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 1
- DBCKRBGYGMVSTI-UHFFFAOYSA-N 2-oxo-7-[2-[2-[3-(2-phenylethoxy)propylsulfonyl]ethylazaniumyl]ethyl]-3h-1,3-benzothiazol-4-olate Chemical compound C1=2SC(=O)NC=2C(O)=CC=C1CCNCCS(=O)(=O)CCCOCCC1=CC=CC=C1 DBCKRBGYGMVSTI-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- HKFKONSKOCERKL-UHFFFAOYSA-N 3-(2-phenylpyridin-4-yl)-7-(1-propylpiperidin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1CN(CCC)CCC1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 HKFKONSKOCERKL-UHFFFAOYSA-N 0.000 description 1
- YMTYGSHGVUGIOK-UHFFFAOYSA-N 3-(2-phenylpyridin-4-yl)-7-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=NNC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 YMTYGSHGVUGIOK-UHFFFAOYSA-N 0.000 description 1
- NYHHILMEJREZBI-UHFFFAOYSA-N 3-(2-phenylpyridin-4-yl)-7-(3-piperidin-1-ylphenyl)imidazo[1,2-a]pyridine Chemical compound C1CCCCN1C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 NYHHILMEJREZBI-UHFFFAOYSA-N 0.000 description 1
- NTPQBXXZDOEBFU-UHFFFAOYSA-N 3-(2-phenylpyridin-4-yl)-7-[2-(trifluoromethyl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound C1=NC(C(F)(F)F)=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 NTPQBXXZDOEBFU-UHFFFAOYSA-N 0.000 description 1
- QEHOCJDUHNBUAH-UHFFFAOYSA-N 3-(2-phenylpyridin-4-yl)-7-[4-(piperidin-1-ylmethyl)phenyl]imidazo[1,2-a]pyridine Chemical compound C=1C=C(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)C=CC=1CN1CCCCC1 QEHOCJDUHNBUAH-UHFFFAOYSA-N 0.000 description 1
- RJFOCPJCHLMVLV-UHFFFAOYSA-N 3-(2-phenylpyridin-4-yl)-7-[6-(3-piperidin-1-ylpropoxy)pyridin-3-yl]imidazo[1,2-a]pyridine Chemical compound C1CCCCN1CCCOC(N=C1)=CC=C1C(=CC1=NC=2)C=CN1C=2C(C=1)=CC=NC=1C1=CC=CC=C1 RJFOCPJCHLMVLV-UHFFFAOYSA-N 0.000 description 1
- LXRNWRRCMZQNEY-UHFFFAOYSA-N 3-(2-phenylpyridin-4-yl)-7-pyridin-2-ylimidazo[1,2-a]pyridine Chemical compound C=1N=C2C=C(C=3N=CC=CC=3)C=CN2C=1C(C=1)=CC=NC=1C1=CC=CC=C1 LXRNWRRCMZQNEY-UHFFFAOYSA-N 0.000 description 1
- KOOIMHUHLGXQRM-UHFFFAOYSA-N 3-(2-phenylpyridin-4-yl)-7-pyrimidin-5-ylimidazo[1,2-a]pyridine Chemical compound C=1N=C2C=C(C=3C=NC=NC=3)C=CN2C=1C(C=1)=CC=NC=1C1=CC=CC=C1 KOOIMHUHLGXQRM-UHFFFAOYSA-N 0.000 description 1
- DDYUBCCTNHWSQM-UHFFFAOYSA-N 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-(1,3-dioxoisoindol-2-yl)propanamide Chemical compound COC1=CC=C(C(CC(N)=O)N2C(C3=CC=CC=C3C2=O)=O)C=C1OC1CCCC1 DDYUBCCTNHWSQM-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical class C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- YWYUQSGYKDEAMJ-QFIPXVFZSA-N 3-[(2s)-7-[3-[2-(cyclopropylmethyl)-3-methoxy-4-(methylcarbamoyl)phenoxy]propoxy]-8-propyl-3,4-dihydro-2h-chromen-2-yl]propanoic acid Chemical compound O([C@H](CCC(O)=O)CCC=1C=C2)C=1C(CCC)=C2OCCCOC1=CC=C(C(=O)NC)C(OC)=C1CC1CC1 YWYUQSGYKDEAMJ-QFIPXVFZSA-N 0.000 description 1
- RCMWSSVEYCGTIQ-UHFFFAOYSA-N 3-[2-(2,4-difluorophenyl)pyridin-4-yl]-7-(1-methylpyrazol-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=NN(C)C=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C(=CC(F)=CC=3)F)N2C=C1 RCMWSSVEYCGTIQ-UHFFFAOYSA-N 0.000 description 1
- SDCHIKYJNIHVCD-UHFFFAOYSA-N 3-[2-(2,4-difluorophenyl)pyridin-4-yl]-7-pyridin-3-ylimidazo[1,2-a]pyridine Chemical compound FC1=CC(F)=CC=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C=2C=NC=CC=2)=CC=N1 SDCHIKYJNIHVCD-UHFFFAOYSA-N 0.000 description 1
- AODFZLYABGSIMU-UHFFFAOYSA-N 3-[2-(2-fluorophenyl)pyridin-4-yl]-7-(1-methylpyrazol-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=NN(C)C=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C(=CC=CC=3)F)N2C=C1 AODFZLYABGSIMU-UHFFFAOYSA-N 0.000 description 1
- DFIJXQJDUDLICW-UHFFFAOYSA-N 3-[2-(2-fluorophenyl)pyridin-4-yl]-7-(6-methylpyridin-3-yl)imidazo[1,2-a]pyridine Chemical compound C1=NC(C)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C(=CC=CC=3)F)N2C=C1 DFIJXQJDUDLICW-UHFFFAOYSA-N 0.000 description 1
- FYBCQRGPRLBZJV-UHFFFAOYSA-N 3-[2-(2-fluorophenyl)pyridin-4-yl]-7-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]imidazo[1,2-a]pyridine Chemical compound C1CN(C)CCN1CC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C(=CC=CC=2)F)=C1 FYBCQRGPRLBZJV-UHFFFAOYSA-N 0.000 description 1
- YTDDMTICGMDFDY-UHFFFAOYSA-N 3-[2-(2-fluorophenyl)pyridin-4-yl]-7-pyridin-3-ylimidazo[1,2-a]pyridine Chemical compound FC1=CC=CC=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C=2C=NC=CC=2)=CC=N1 YTDDMTICGMDFDY-UHFFFAOYSA-N 0.000 description 1
- ZIVIAMQQLQMJAN-UHFFFAOYSA-N 3-[2-(2-methylpyrrolidin-1-yl)pyridin-4-yl]-7-pyridin-3-ylimidazo[1,2-a]pyridine Chemical compound CC1CCCN1C1=CC(C=2N3C=CC(=CC3=NC=2)C=2C=NC=CC=2)=CC=N1 ZIVIAMQQLQMJAN-UHFFFAOYSA-N 0.000 description 1
- GWTNREGVEXHATG-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)pyridin-4-yl]-7-(1,3,5-trimethylpyrazol-4-yl)imidazo[1,2-a]pyridine Chemical compound CC1=NN(C)C(C)=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC(F)=CC=3)N2C=C1 GWTNREGVEXHATG-UHFFFAOYSA-N 0.000 description 1
- UBGZVFWEFMJVBV-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)pyridin-4-yl]-7-(1-methylpyrazol-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=NN(C)C=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC(F)=CC=3)N2C=C1 UBGZVFWEFMJVBV-UHFFFAOYSA-N 0.000 description 1
- FCRUHTABBNMSCM-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)pyridin-4-yl]-7-(1-piperidin-4-ylpyrazol-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C2=CN(N=C2)C2CCNCC2)=CC=N1 FCRUHTABBNMSCM-UHFFFAOYSA-N 0.000 description 1
- NAWLVVYZOKOHJA-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)pyridin-4-yl]-7-(6-methoxypyridin-3-yl)imidazo[1,2-a]pyridine Chemical compound C1=NC(OC)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC(F)=CC=3)N2C=C1 NAWLVVYZOKOHJA-UHFFFAOYSA-N 0.000 description 1
- ZUFRWDAXJHQFSR-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)pyridin-4-yl]-7-(6-methylpyridin-3-yl)imidazo[1,2-a]pyridine Chemical compound C1=NC(C)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC(F)=CC=3)N2C=C1 ZUFRWDAXJHQFSR-UHFFFAOYSA-N 0.000 description 1
- OLZBRWFGDKTMCW-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)pyridin-4-yl]-7-(6-propan-2-yloxypyridin-3-yl)imidazo[1,2-a]pyridine Chemical compound C1=NC(OC(C)C)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC(F)=CC=3)N2C=C1 OLZBRWFGDKTMCW-UHFFFAOYSA-N 0.000 description 1
- XGPDDSFERSDHGB-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)pyridin-4-yl]-7-[6-(2-methylpropoxy)pyridin-3-yl]imidazo[1,2-a]pyridine Chemical compound C1=NC(OCC(C)C)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC(F)=CC=3)N2C=C1 XGPDDSFERSDHGB-UHFFFAOYSA-N 0.000 description 1
- XCZJLZMXYZFBKR-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)pyridin-4-yl]-7-pyridin-3-ylimidazo[1,2-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C=2C=NC=CC=2)=CC=N1 XCZJLZMXYZFBKR-UHFFFAOYSA-N 0.000 description 1
- UFCWOKFSQYVKQQ-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)pyridin-4-yl]-7-pyridin-4-ylimidazo[1,2-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C=2C=CN=CC=2)=CC=N1 UFCWOKFSQYVKQQ-UHFFFAOYSA-N 0.000 description 1
- BLFSVFMYPQZFHA-UHFFFAOYSA-N 3-[2-(cyclohexen-1-yl)pyridin-4-yl]-7-pyridin-3-ylimidazo[1,2-a]pyridine Chemical compound C1CCCC(C=2N=CC=C(C=2)C=2N3C=CC(=CC3=NC=2)C=2C=NC=CC=2)=C1 BLFSVFMYPQZFHA-UHFFFAOYSA-N 0.000 description 1
- HHFAGTCGNOOBKO-UHFFFAOYSA-N 3-[2-(cyclopenten-1-yl)pyridin-4-yl]-7-(1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1CCC=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C=2CCNCC=2)=CC=N1 HHFAGTCGNOOBKO-UHFFFAOYSA-N 0.000 description 1
- WXAQFEUEXBOSCC-UHFFFAOYSA-N 3-[2-(cyclopenten-1-yl)pyridin-4-yl]-7-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1N(C)CCC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2CCCC=2)=C1 WXAQFEUEXBOSCC-UHFFFAOYSA-N 0.000 description 1
- WHDZSUZZQYMMFL-UHFFFAOYSA-N 3-[2-(cyclopenten-1-yl)pyridin-4-yl]-7-(1-methylpyrazol-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=NN(C)C=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3CCCC=3)N2C=C1 WHDZSUZZQYMMFL-UHFFFAOYSA-N 0.000 description 1
- ZDGBQPWULFYGGE-UHFFFAOYSA-N 3-[2-(cyclopenten-1-yl)pyridin-4-yl]-7-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridine Chemical compound C1CCC=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C2=CNN=C2)=CC=N1 ZDGBQPWULFYGGE-UHFFFAOYSA-N 0.000 description 1
- VPWZWPJWTUTBLE-UHFFFAOYSA-N 3-[2-(cyclopenten-1-yl)pyridin-4-yl]-7-(3-fluorophenyl)imidazo[1,2-a]pyridine Chemical compound FC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2CCCC=2)=C1 VPWZWPJWTUTBLE-UHFFFAOYSA-N 0.000 description 1
- WNWOIEFLGIGWDR-UHFFFAOYSA-N 3-[2-(cyclopenten-1-yl)pyridin-4-yl]-7-(6-methoxypyridin-3-yl)imidazo[1,2-a]pyridine Chemical compound C1=NC(OC)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3CCCC=3)N2C=C1 WNWOIEFLGIGWDR-UHFFFAOYSA-N 0.000 description 1
- BIUVNCGVLOHMBY-UHFFFAOYSA-N 3-[2-(cyclopenten-1-yl)pyridin-4-yl]-7-(furan-3-yl)imidazo[1,2-a]pyridine Chemical compound C1CCC=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C2=COC=C2)=CC=N1 BIUVNCGVLOHMBY-UHFFFAOYSA-N 0.000 description 1
- JKSXVKXUHHGNON-UHFFFAOYSA-N 3-[2-(cyclopenten-1-yl)pyridin-4-yl]-7-phenylimidazo[1,2-a]pyridine Chemical compound C1CCC=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C=2C=CC=CC=2)=CC=N1 JKSXVKXUHHGNON-UHFFFAOYSA-N 0.000 description 1
- GRFBGSFYVOBSNS-UHFFFAOYSA-N 3-[2-(cyclopenten-1-yl)pyridin-4-yl]-7-thiophen-3-ylimidazo[1,2-a]pyridine Chemical compound C1CCC=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C2=CSC=C2)=CC=N1 GRFBGSFYVOBSNS-UHFFFAOYSA-N 0.000 description 1
- XWNZXESXGVOEFF-UHFFFAOYSA-N 3-[2-(furan-3-yl)pyridin-4-yl]-6-(1h-pyrazol-5-yl)imidazo[1,2-a]pyridine Chemical compound N1C=CC(C2=CN3C(C=4C=C(N=CC=4)C4=COC=C4)=CN=C3C=C2)=N1 XWNZXESXGVOEFF-UHFFFAOYSA-N 0.000 description 1
- NFSPKMQWJOZYDH-UHFFFAOYSA-N 3-[2-(furan-3-yl)pyridin-4-yl]-6-(6-piperazin-1-ylpyridin-3-yl)imidazo[1,2-a]pyridine Chemical compound C1CNCCN1C1=CC=C(C2=CN3C(C=4C=C(N=CC=4)C4=COC=C4)=CN=C3C=C2)C=N1 NFSPKMQWJOZYDH-UHFFFAOYSA-N 0.000 description 1
- SVJLRQVYDXTFSA-UHFFFAOYSA-N 3-[2-(furan-3-yl)pyridin-4-yl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine Chemical compound N12C=C(C(F)(F)F)C=CC2=NC=C1C(C=1)=CC=NC=1C=1C=COC=1 SVJLRQVYDXTFSA-UHFFFAOYSA-N 0.000 description 1
- POSJSXUOHJZYFY-UHFFFAOYSA-N 3-[2-(furan-3-yl)pyridin-4-yl]-6-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]imidazo[1,2-a]pyridine Chemical compound C1CN(C)CCN1C1=CC=C(C2=CN3C(C=4C=C(N=CC=4)C4=COC=C4)=CN=C3C=C2)C=N1 POSJSXUOHJZYFY-UHFFFAOYSA-N 0.000 description 1
- HANMOWMQPYVCRM-UHFFFAOYSA-N 3-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]-1-propan-2-ylpyridin-2-one Chemical compound O=C1N(C(C)C)C=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 HANMOWMQPYVCRM-UHFFFAOYSA-N 0.000 description 1
- SLHZTRCBRSFROY-UHFFFAOYSA-N 3-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]aniline Chemical compound NC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 SLHZTRCBRSFROY-UHFFFAOYSA-N 0.000 description 1
- GTHYHUYZHXCKQK-UHFFFAOYSA-N 3-[3-(2-pyrrolidin-1-ylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]benzaldehyde Chemical compound O=CC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)N2CCCC2)=C1 GTHYHUYZHXCKQK-UHFFFAOYSA-N 0.000 description 1
- VQGUKTWLHGQYIE-UHFFFAOYSA-N 3-[3-[2-(2,4-difluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C(=CC(F)=CC=2)F)=C1 VQGUKTWLHGQYIE-UHFFFAOYSA-N 0.000 description 1
- QBXYHQXGVORLLG-UHFFFAOYSA-N 3-[3-[2-(2-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C(=CC=CC=2)F)=C1 QBXYHQXGVORLLG-UHFFFAOYSA-N 0.000 description 1
- FNGPHIPQOVZQEJ-UHFFFAOYSA-N 3-[3-[2-(3-methylpyrazol-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]benzaldehyde Chemical compound N1=C(C)C=CN1C1=CC(C=2N3C=CC(=CC3=NC=2)C=2C=C(C=O)C=CC=2)=CC=N1 FNGPHIPQOVZQEJ-UHFFFAOYSA-N 0.000 description 1
- WUGFFWYCPGBHEN-UHFFFAOYSA-N 3-[3-[2-(4,4-dimethylcyclopenten-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2CC(C)(C)CC=2)=C1 WUGFFWYCPGBHEN-UHFFFAOYSA-N 0.000 description 1
- WSLWDYFVQCTRRJ-UHFFFAOYSA-N 3-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC(F)=CC=2)=C1 WSLWDYFVQCTRRJ-UHFFFAOYSA-N 0.000 description 1
- JFZANFYZCQLJLE-UHFFFAOYSA-N 3-[3-[2-(cyclopenten-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2CCCC=2)=C1 JFZANFYZCQLJLE-UHFFFAOYSA-N 0.000 description 1
- IUVFVBKDYAPPPE-UHFFFAOYSA-N 3-[3-[2-(cyclopenten-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]benzaldehyde Chemical compound O=CC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2CCCC=2)=C1 IUVFVBKDYAPPPE-UHFFFAOYSA-N 0.000 description 1
- MUFQZHHUJCMIKI-UHFFFAOYSA-N 3-[3-[2-(cyclopropylamino)-6-phenylpyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=C(NC3CC3)C=2)C=2C=CC=CC=2)=C1 MUFQZHHUJCMIKI-UHFFFAOYSA-N 0.000 description 1
- CDLZIIHRMLFGPK-UHFFFAOYSA-N 3-[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(C2=CN3C(C=4C=C(N=CC=4)C4=COC=C4)=CN=C3C=C2)=C1 CDLZIIHRMLFGPK-UHFFFAOYSA-N 0.000 description 1
- QIXVRLCKXXCGQQ-UHFFFAOYSA-N 3-[3-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenoxy]-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCOC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC(F)=CC=2)=C1 QIXVRLCKXXCGQQ-UHFFFAOYSA-N 0.000 description 1
- FHLTYWSRZYVLDX-UHFFFAOYSA-N 3-[5-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]pyridin-2-yl]oxy-n,n-dimethylpropan-1-amine Chemical compound C1=NC(OCCCN(C)C)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC(F)=CC=3)N2C=C1 FHLTYWSRZYVLDX-UHFFFAOYSA-N 0.000 description 1
- UYNGFXHJWXXOJB-UHFFFAOYSA-N 3-[7-(1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N3C=CC(=CC3=NC=2)C=2CCNCC=2)=C1 UYNGFXHJWXXOJB-UHFFFAOYSA-N 0.000 description 1
- BAQNNIZMLXXQIX-UHFFFAOYSA-N 3-[7-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)imidazo[1,2-a]pyridin-3-yl]benzamide Chemical compound C1N(C)CCC(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)C(N)=O)=C1 BAQNNIZMLXXQIX-UHFFFAOYSA-N 0.000 description 1
- FQJOIOMUXBFXBF-UHFFFAOYSA-N 3-[7-[1-(2-methylpropyl)-6-oxopyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]benzamide Chemical compound C1=CC(=O)N(CC(C)C)C=C1C1=CC2=NC=C(C=3C=C(C=CC=3)C(N)=O)N2C=C1 FQJOIOMUXBFXBF-UHFFFAOYSA-N 0.000 description 1
- CXVLMLRDIJBWSS-UHFFFAOYSA-N 3-[7-[3-(ethylaminomethyl)phenyl]imidazo[1,2-a]pyridin-3-yl]-n-methylbenzamide Chemical compound CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)C(=O)NC)=C1 CXVLMLRDIJBWSS-UHFFFAOYSA-N 0.000 description 1
- FWEJBBAGKDBYOO-UHFFFAOYSA-N 3-[7-[3-(ethylaminomethyl)phenyl]imidazo[1,2-a]pyridin-3-yl]benzamide Chemical compound CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)C(N)=O)=C1 FWEJBBAGKDBYOO-UHFFFAOYSA-N 0.000 description 1
- NSNNCIJGMNNCEV-UHFFFAOYSA-N 3-[7-[3-[(3-methylbutylamino)methyl]phenyl]imidazo[1,2-a]pyridin-3-yl]benzamide Chemical compound CC(C)CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)C(N)=O)=C1 NSNNCIJGMNNCEV-UHFFFAOYSA-N 0.000 description 1
- GSBSXFXYBJRVDL-UHFFFAOYSA-N 3-[7-[4-(propylaminomethyl)phenyl]imidazo[1,2-a]pyridin-3-yl]benzamide Chemical compound C1=CC(CNCCC)=CC=C1C1=CC2=NC=C(C=3C=C(C=CC=3)C(N)=O)N2C=C1 GSBSXFXYBJRVDL-UHFFFAOYSA-N 0.000 description 1
- GRTACEORZTZUNY-UHFFFAOYSA-N 3-[7-[6-(2-methylpropoxy)pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]benzamide Chemical compound C1=NC(OCC(C)C)=CC=C1C1=CC2=NC=C(C=3C=C(C=CC=3)C(N)=O)N2C=C1 GRTACEORZTZUNY-UHFFFAOYSA-N 0.000 description 1
- ZLXQOXRSNUFMOT-UHFFFAOYSA-N 3-[[3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1C(O)CCCC1NC1=CN2C(C=3C=C(C=CC=3)N3N=CC=C3)=CN=C2C=C1 ZLXQOXRSNUFMOT-UHFFFAOYSA-N 0.000 description 1
- XJXTZJJCIZUJPU-UHFFFAOYSA-N 3-[[3-[2-(1,2-oxazol-4-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1C(O)CCCC1NC1=CN2C(C=3C=C(N=CC=3)C3=CON=C3)=CN=C2C=C1 XJXTZJJCIZUJPU-UHFFFAOYSA-N 0.000 description 1
- GTSUNNVKKLPMNZ-UHFFFAOYSA-N 3-[[3-[2-(3,5-dimethylpyrazol-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]-1-methylcyclohexan-1-ol Chemical compound N1=C(C)C=C(C)N1C1=CC(C=2N3C=C(NC4CC(C)(O)CCC4)C=CC3=NC=2)=CC=N1 GTSUNNVKKLPMNZ-UHFFFAOYSA-N 0.000 description 1
- CUXGITJMIIPBFJ-UHFFFAOYSA-N 3-[[3-[2-(3-cyclopropylpyrazol-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]-1-methylcyclohexan-1-ol Chemical compound C1C(C)(O)CCCC1NC1=CN2C(C=3C=C(N=CC=3)N3N=C(C=C3)C3CC3)=CN=C2C=C1 CUXGITJMIIPBFJ-UHFFFAOYSA-N 0.000 description 1
- AGBBQXNHMIFXGP-UHFFFAOYSA-N 3-[[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1C(O)CCCC1NC1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 AGBBQXNHMIFXGP-UHFFFAOYSA-N 0.000 description 1
- JDHPHGQDXTVHNQ-UHFFFAOYSA-N 3-[[3-[2-(tert-butylamino)-6-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound N=1C(NC(C)(C)C)=CC(C=2N3C=C(NC4CC(O)CCC4)C=CC3=NC=2)=CC=1C=1C=COC=1 JDHPHGQDXTVHNQ-UHFFFAOYSA-N 0.000 description 1
- PJIFKWKBFMLLLT-UHFFFAOYSA-N 3-[[3-[2-(triazol-2-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound C1C(O)CCCC1NC1=CN2C(C=3C=C(N=CC=3)N3N=CC=N3)=CN=C2C=C1 PJIFKWKBFMLLLT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NGNBYJVRSSBNLB-UHFFFAOYSA-N 3-bromo-6-chloroimidazo[1,2-a]pyridine;hydrobromide Chemical compound Br.C1=C(Cl)C=CC2=NC=C(Br)N21 NGNBYJVRSSBNLB-UHFFFAOYSA-N 0.000 description 1
- HTOQENIDOXQCQH-UHFFFAOYSA-N 3-bromo-7-pyridin-4-ylimidazo[1,2-a]pyridine Chemical compound C1=CN2C(Br)=CN=C2C=C1C1=CC=NC=C1 HTOQENIDOXQCQH-UHFFFAOYSA-N 0.000 description 1
- APYSHMNJHJRIDR-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine Chemical compound C1=CC=CN2C(Br)=CN=C21 APYSHMNJHJRIDR-UHFFFAOYSA-N 0.000 description 1
- LJQNMDZRCXJETK-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine;hydron;chloride Chemical compound Cl.CN(C)CCCCl LJQNMDZRCXJETK-UHFFFAOYSA-N 0.000 description 1
- DUDNCXOSIYPWMR-UHFFFAOYSA-N 3-fluoro-5-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]benzoic acid Chemical compound OC(=O)C1=CC(F)=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 DUDNCXOSIYPWMR-UHFFFAOYSA-N 0.000 description 1
- ZQGARJVXEPEEMV-UHFFFAOYSA-N 3-fluoro-5-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]phenol Chemical compound OC1=CC(F)=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 ZQGARJVXEPEEMV-UHFFFAOYSA-N 0.000 description 1
- XCCHPXGAVIIULR-UHFFFAOYSA-N 3-fluoro-5-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC(F)=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC(F)=CC=2)=C1 XCCHPXGAVIIULR-UHFFFAOYSA-N 0.000 description 1
- KFZNVYIIBBRFLF-UHFFFAOYSA-N 3-fluoro-n-methyl-5-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]benzamide Chemical compound CNC(=O)C1=CC(F)=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 KFZNVYIIBBRFLF-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- RSMUJOLLTRGPHT-UHFFFAOYSA-N 4-[3-(2-pyrazol-1-ylpyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CN2C(C=3C=C(N=CC=3)N3N=CC=C3)=CN=C2C=C1 RSMUJOLLTRGPHT-UHFFFAOYSA-N 0.000 description 1
- WYCZTBZEJWWKLL-UHFFFAOYSA-N 4-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-n-(2-piperidin-1-ylethyl)benzamide Chemical compound C1=CC(F)=CC=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C=2C=CC(=CC=2)C(=O)NCCN2CCCCC2)=CC=N1 WYCZTBZEJWWKLL-UHFFFAOYSA-N 0.000 description 1
- CMHIZLDMQPRTBW-UHFFFAOYSA-N 4-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-n-[2-(4-methylpiperazin-1-yl)ethyl]benzamide Chemical compound C1CN(C)CCN1CCNC(=O)C1=CC=C(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC(F)=CC=2)C=C1 CMHIZLDMQPRTBW-UHFFFAOYSA-N 0.000 description 1
- NJGPAZRBMJUCFR-UHFFFAOYSA-N 4-[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]-n-(2-hydroxyethyl)benzamide Chemical compound C1=CC(C(=O)NCCO)=CC=C1C1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 NJGPAZRBMJUCFR-UHFFFAOYSA-N 0.000 description 1
- FJTAPTWMPDVCHY-UHFFFAOYSA-N 4-[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]-n-propan-2-ylbenzamide Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1C1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 FJTAPTWMPDVCHY-UHFFFAOYSA-N 0.000 description 1
- XRDPCELZXSBTNL-UHFFFAOYSA-N 4-[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 XRDPCELZXSBTNL-UHFFFAOYSA-N 0.000 description 1
- GSSMWGUMQKFTIN-UHFFFAOYSA-N 4-[5-[3-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]pyridin-2-yl]morpholine Chemical compound C1=NN(C)C=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C=2C=NC(=CC=2)N2CCOCC2)=CC=N1 GSSMWGUMQKFTIN-UHFFFAOYSA-N 0.000 description 1
- WPEWOJFBAROORO-UHFFFAOYSA-N 4-[7-[3-(ethylaminomethyl)phenyl]imidazo[1,2-a]pyridin-3-yl]-6-phenyl-n-propan-2-ylpyridin-2-amine Chemical compound CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=C(NC(C)C)C=2)C=2C=CC=CC=2)=C1 WPEWOJFBAROORO-UHFFFAOYSA-N 0.000 description 1
- NVLNDMMPZJBNLU-UHFFFAOYSA-N 4-[[3-[2-(3-methylpyrazol-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]amino]cyclohexan-1-ol Chemical compound N1=C(C)C=CN1C1=CC(C=2N3C=C(NC4CCC(O)CC4)C=CC3=NC=2)=CC=N1 NVLNDMMPZJBNLU-UHFFFAOYSA-N 0.000 description 1
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 1
- BAQKUNMKVAPWGU-UHFFFAOYSA-N 4-bromopyridin-2-amine Chemical compound NC1=CC(Br)=CC=N1 BAQKUNMKVAPWGU-UHFFFAOYSA-N 0.000 description 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- IHOXNOQMRZISPV-YJYMSZOUSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-methoxyphenyl)propan-2-yl]azaniumyl]ethyl]-2-oxo-1h-quinolin-8-olate Chemical compound C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 IHOXNOQMRZISPV-YJYMSZOUSA-N 0.000 description 1
- JOPSSWGWLCLPPF-RUDMXATFSA-N 5-[2-(2-carboxyethyl)-3-[(e)-6-(4-methoxyphenyl)hex-5-enoxy]phenoxy]pentanoic acid Chemical compound C1=CC(OC)=CC=C1\C=C\CCCCOC1=CC=CC(OCCCCC(O)=O)=C1CCC(O)=O JOPSSWGWLCLPPF-RUDMXATFSA-N 0.000 description 1
- FMEGCUZWEVQJRX-UHFFFAOYSA-N 5-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]-1-(3-piperidin-1-ylpropyl)pyridin-2-one Chemical compound O=C1C=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=CN1CCCN1CCCCC1 FMEGCUZWEVQJRX-UHFFFAOYSA-N 0.000 description 1
- PGXMROFVAXWKOS-UHFFFAOYSA-N 5-[3-[2-(2-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-n,n-dimethylpyridin-2-amine Chemical class C1=NC(N(C)C)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C(=CC=CC=3)F)N2C=C1 PGXMROFVAXWKOS-UHFFFAOYSA-N 0.000 description 1
- AJTSBELVTDBLAO-UHFFFAOYSA-N 5-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-1-(2-methylpropyl)pyridin-2-one Chemical compound C1=CC(=O)N(CC(C)C)C=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC(F)=CC=3)N2C=C1 AJTSBELVTDBLAO-UHFFFAOYSA-N 0.000 description 1
- HHULBOJNHXYJIA-UHFFFAOYSA-N 5-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-1-(3-piperidin-1-ylpropyl)pyridin-2-one Chemical compound C1=CC(F)=CC=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C2=CN(CCCN3CCCCC3)C(=O)C=C2)=CC=N1 HHULBOJNHXYJIA-UHFFFAOYSA-N 0.000 description 1
- BXQYASMSZMDSHS-UHFFFAOYSA-N 5-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-1-propan-2-ylpyridin-2-one Chemical compound C1=CC(=O)N(C(C)C)C=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC(F)=CC=3)N2C=C1 BXQYASMSZMDSHS-UHFFFAOYSA-N 0.000 description 1
- BYDZMHGNWZEUEO-UHFFFAOYSA-N 5-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-1H-pyridin-2-one Chemical compound C1=CC(F)=CC=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C2=CNC(=O)C=C2)=CC=N1 BYDZMHGNWZEUEO-UHFFFAOYSA-N 0.000 description 1
- BBNIOSDHAIMBEG-UHFFFAOYSA-N 5-[3-[2-(cyclopenten-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-1H-pyridin-2-one Chemical compound N1C(=O)C=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2CCCC=2)=C1 BBNIOSDHAIMBEG-UHFFFAOYSA-N 0.000 description 1
- TXWDVWSJMDFNQY-UHFFFAOYSA-N 5-cyclopropyl-1h-pyrazole Chemical compound C1CC1C1=CC=NN1 TXWDVWSJMDFNQY-UHFFFAOYSA-N 0.000 description 1
- IVILGUFRMDBUEQ-UHFFFAOYSA-N 5-iodopyridin-2-amine Chemical compound NC1=CC=C(I)C=N1 IVILGUFRMDBUEQ-UHFFFAOYSA-N 0.000 description 1
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 1
- BUBGRYCPHSKERR-UHFFFAOYSA-N 6-(1h-pyrazol-5-yl)-3-(2-pyrazol-1-ylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=CC=NN1C1=CC(C=2N3C=C(C=CC3=NC=2)C2=NNC=C2)=CC=N1 BUBGRYCPHSKERR-UHFFFAOYSA-N 0.000 description 1
- TZBJYLKSWQJTCR-UHFFFAOYSA-N 6-(2-cyclopropylpyridin-4-yl)-3-(2-pyrazol-1-ylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1CC1C1=CC(C2=CN3C(C=4C=C(N=CC=4)N4N=CC=C4)=CN=C3C=C2)=CC=N1 TZBJYLKSWQJTCR-UHFFFAOYSA-N 0.000 description 1
- NOGPTVLAMXARQC-UHFFFAOYSA-N 6-(4-fluorophenyl)-4-[7-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-n-methylpyridin-2-amine Chemical class N=1C(NC)=CC(C=2N3C=CC(=CC3=NC=2)C=2C=CC(F)=CC=2)=CC=1C1=CC=C(F)C=C1 NOGPTVLAMXARQC-UHFFFAOYSA-N 0.000 description 1
- IBOZOWZSXZNIHI-UHFFFAOYSA-N 6-(trifluoromethyl)pyridin-3-amine Chemical compound NC1=CC=C(C(F)(F)F)N=C1 IBOZOWZSXZNIHI-UHFFFAOYSA-N 0.000 description 1
- QFPAQFNVRQROAR-UHFFFAOYSA-N 6-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]-3-(2-pyrazol-1-ylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1CN(C)CCN1C1=CC(C2=CN3C(C=4C=C(N=CC=4)N4N=CC=C4)=CN=C3C=C2)=CC=N1 QFPAQFNVRQROAR-UHFFFAOYSA-N 0.000 description 1
- XTHKRYHULUJQHN-UHFFFAOYSA-N 6-bromopyridin-3-amine Chemical compound NC1=CC=C(Br)N=C1 XTHKRYHULUJQHN-UHFFFAOYSA-N 0.000 description 1
- QAJYCQZQLVENRZ-UHFFFAOYSA-N 6-chloropyridin-3-amine Chemical compound NC1=CC=C(Cl)N=C1 QAJYCQZQLVENRZ-UHFFFAOYSA-N 0.000 description 1
- XBEKLVMGVLFJBX-UHFFFAOYSA-N 7-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1N(C)CCC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 XBEKLVMGVLFJBX-UHFFFAOYSA-N 0.000 description 1
- HUNTYVHHERPKPB-UHFFFAOYSA-N 7-(1-methylpiperidin-4-yl)-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1CN(C)CCC1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 HUNTYVHHERPKPB-UHFFFAOYSA-N 0.000 description 1
- GNTXLXJPLSUUNC-UHFFFAOYSA-N 7-(1-methylpyrazol-4-yl)-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=NN(C)C=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 GNTXLXJPLSUUNC-UHFFFAOYSA-N 0.000 description 1
- KTJOSJOJSXMMCG-UHFFFAOYSA-N 7-(2-fluoropyridin-3-yl)-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound FC1=NC=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 KTJOSJOJSXMMCG-UHFFFAOYSA-N 0.000 description 1
- PNJOQKBLHDLHKH-UHFFFAOYSA-N 7-(2-methylpyridin-4-yl)-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=NC(C)=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 PNJOQKBLHDLHKH-UHFFFAOYSA-N 0.000 description 1
- QSOFSCLHKSNFST-UHFFFAOYSA-N 7-(3,4-difluorophenyl)-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=C(F)C(F)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 QSOFSCLHKSNFST-UHFFFAOYSA-N 0.000 description 1
- WJUYZQBFRRKJGB-UHFFFAOYSA-N 7-(3,5-difluorophenyl)-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound FC1=CC(F)=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 WJUYZQBFRRKJGB-UHFFFAOYSA-N 0.000 description 1
- NUNNXBAAJHIITH-UHFFFAOYSA-N 7-(3,5-dimethyl-1h-pyrazol-4-yl)-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound CC1=NNC(C)=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 NUNNXBAAJHIITH-UHFFFAOYSA-N 0.000 description 1
- NBPUVFTWVMHQKU-UHFFFAOYSA-N 7-(3-chlorophenyl)-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound ClC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 NBPUVFTWVMHQKU-UHFFFAOYSA-N 0.000 description 1
- NAGPVZJGKMPRGY-UHFFFAOYSA-N 7-(3-fluorophenyl)-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound FC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 NAGPVZJGKMPRGY-UHFFFAOYSA-N 0.000 description 1
- ZOENCXWWJYYKOZ-UHFFFAOYSA-N 7-(3-fluorophenyl)-3-[2-(2-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound FC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C(=CC=CC=2)F)=C1 ZOENCXWWJYYKOZ-UHFFFAOYSA-N 0.000 description 1
- CIZNFZUVNIAXST-UHFFFAOYSA-N 7-(3-fluoropyridin-4-yl)-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound FC1=CN=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 CIZNFZUVNIAXST-UHFFFAOYSA-N 0.000 description 1
- JEWRPYGCIUCPFL-UHFFFAOYSA-N 7-(6-fluoropyridin-3-yl)-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=NC(F)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 JEWRPYGCIUCPFL-UHFFFAOYSA-N 0.000 description 1
- IWTHDKNGHWFXDN-UHFFFAOYSA-N 7-(6-fluoropyridin-3-yl)-3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridine Chemical compound C1=NC(F)=CC=C1C1=CC2=NC=C(C=3C=C(C=CC=3)N3N=CC=C3)N2C=C1 IWTHDKNGHWFXDN-UHFFFAOYSA-N 0.000 description 1
- DHZYKHKUXCBCQY-UHFFFAOYSA-N 7-(6-methylpyridin-3-yl)-3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridine Chemical compound C1=NC(C)=CC=C1C1=CC2=NC=C(C=3C=C(C=CC=3)N3N=CC=C3)N2C=C1 DHZYKHKUXCBCQY-UHFFFAOYSA-N 0.000 description 1
- NRGSDLGKLFQRHW-UHFFFAOYSA-N 7-[1-(2-methylpropyl)-3,6-dihydro-2h-pyridin-4-yl]-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1N(CC(C)C)CCC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 NRGSDLGKLFQRHW-UHFFFAOYSA-N 0.000 description 1
- WXEDDMCASLLCAX-UHFFFAOYSA-N 7-[6-(cyclopropylmethoxy)pyridin-3-yl]-3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=CC(C=2N3C=CC(=CC3=NC=2)C=2C=NC(OCC3CC3)=CC=2)=CC=N1 WXEDDMCASLLCAX-UHFFFAOYSA-N 0.000 description 1
- KIAUTLHGPMFSAF-UHFFFAOYSA-N 7-chloro-3-(3-pyrrolidin-1-ylphenyl)imidazo[1,2-a]pyridine Chemical compound C=1N=C2C=C(Cl)C=CN2C=1C(C=1)=CC=CC=1N1CCCC1 KIAUTLHGPMFSAF-UHFFFAOYSA-N 0.000 description 1
- GUEXRFOUIBIUQW-UHFFFAOYSA-N 7-chloro-3-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound C1=NN(C)C=C1C1=CC(C=2N3C=CC(Cl)=CC3=NC=2)=CC=N1 GUEXRFOUIBIUQW-UHFFFAOYSA-N 0.000 description 1
- LCBYOPZEULGPCH-UHFFFAOYSA-N 7-chloro-3-[2-(3-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound FC1=CC=CC(C=2N=CC=C(C=2)C=2N3C=CC(Cl)=CC3=NC=2)=C1 LCBYOPZEULGPCH-UHFFFAOYSA-N 0.000 description 1
- DXCOUYWVFRISBG-UHFFFAOYSA-N 7-chloro-3-[2-(3-methylcyclopenten-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound CC1CCC(C=2N=CC=C(C=2)C=2N3C=CC(Cl)=CC3=NC=2)=C1 DXCOUYWVFRISBG-UHFFFAOYSA-N 0.000 description 1
- UMTFYSWVZLLQEG-UHFFFAOYSA-N 7-chloro-3-[2-(3-methylphenyl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C=2N=CC=C(C=2)C=2N3C=CC(Cl)=CC3=NC=2)=C1 UMTFYSWVZLLQEG-UHFFFAOYSA-N 0.000 description 1
- PIVZRKRVEJXZJM-UHFFFAOYSA-N 7-chloro-3-[2-(4,4-dimethylcyclopenten-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound C1C(C)(C)CC=C1C1=CC(C=2N3C=CC(Cl)=CC3=NC=2)=CC=N1 PIVZRKRVEJXZJM-UHFFFAOYSA-N 0.000 description 1
- LYGRHOROAFTKPN-UHFFFAOYSA-N 7-chloro-3-[2-(cyclohexen-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound C=1N=C2C=C(Cl)C=CN2C=1C(C=1)=CC=NC=1C1=CCCCC1 LYGRHOROAFTKPN-UHFFFAOYSA-N 0.000 description 1
- KLLHZSMJLRRKIP-UHFFFAOYSA-N 7-chloro-3-[2-(cyclopenten-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound C=1N=C2C=C(Cl)C=CN2C=1C(C=1)=CC=NC=1C1=CCCC1 KLLHZSMJLRRKIP-UHFFFAOYSA-N 0.000 description 1
- ONSOYDYLBUWCDI-UHFFFAOYSA-N 7-chloro-3-[3-(2-methylpyrrolidin-1-yl)phenyl]imidazo[1,2-a]pyridine Chemical compound CC1CCCN1C1=CC=CC(C=2N3C=CC(Cl)=CC3=NC=2)=C1 ONSOYDYLBUWCDI-UHFFFAOYSA-N 0.000 description 1
- CGYXXWWMOTYBCF-UHFFFAOYSA-N 7-phenyl-3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C=1N=C2C=C(C=3C=CC=CC=3)C=CN2C=1C(C=1)=CC=NC=1C1=CC=CC=C1 CGYXXWWMOTYBCF-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 208000007122 AIDS-Associated Nephropathy Diseases 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 108010052946 Activin Receptors Proteins 0.000 description 1
- 102000018918 Activin Receptors Human genes 0.000 description 1
- 208000000884 Airway Obstruction Diseases 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 108010064733 Angiotensins Proteins 0.000 description 1
- 102000015427 Angiotensins Human genes 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 208000037874 Asthma exacerbation Diseases 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- MBUVEWMHONZEQD-UHFFFAOYSA-N Azeptin Chemical compound C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 MBUVEWMHONZEQD-UHFFFAOYSA-N 0.000 description 1
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 102000007350 Bone Morphogenetic Proteins Human genes 0.000 description 1
- 108010007726 Bone Morphogenetic Proteins Proteins 0.000 description 1
- 229940078581 Bone resorption inhibitor Drugs 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 1
- LERNTVKEWCAPOY-VOGVJGKGSA-N C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical compound C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 LERNTVKEWCAPOY-VOGVJGKGSA-N 0.000 description 1
- KORNTPPJEAJQIU-KJXAQDMKSA-N Cabaser Chemical compound C1=CC([C@H]2C[C@H](CN(CC=C)[C@@H]2C2)C(=O)N(CCCN(C)C)C(=O)NCC)=C3C2=CNC3=C1 KORNTPPJEAJQIU-KJXAQDMKSA-N 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- 101150015280 Cel gene Proteins 0.000 description 1
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 description 1
- 241000819038 Chichester Species 0.000 description 1
- 208000032544 Cicatrix Diseases 0.000 description 1
- LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 0.000 description 1
- 208000029147 Collagen-vascular disease Diseases 0.000 description 1
- 102000015225 Connective Tissue Growth Factor Human genes 0.000 description 1
- 108010039419 Connective Tissue Growth Factor Proteins 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- 108010020097 DPC11870-11 Proteins 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010056340 Diabetic ulcer Diseases 0.000 description 1
- 201000003066 Diffuse Scleroderma Diseases 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000010228 Erectile Dysfunction Diseases 0.000 description 1
- RRJFVPUCXDGFJB-UHFFFAOYSA-N Fexofenadine hydrochloride Chemical compound Cl.C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RRJFVPUCXDGFJB-UHFFFAOYSA-N 0.000 description 1
- 206010017076 Fracture Diseases 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 206010018366 Glomerulonephritis acute Diseases 0.000 description 1
- 206010018367 Glomerulonephritis chronic Diseases 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- VPNYRYCIDCJBOM-UHFFFAOYSA-M Glycopyrronium bromide Chemical compound [Br-].C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 VPNYRYCIDCJBOM-UHFFFAOYSA-M 0.000 description 1
- 239000007821 HATU Substances 0.000 description 1
- 206010070737 HIV associated nephropathy Diseases 0.000 description 1
- 241000711557 Hepacivirus Species 0.000 description 1
- 206010019663 Hepatic failure Diseases 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020843 Hyperthermia Diseases 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 208000024934 IgG4-related mediastinitis Diseases 0.000 description 1
- 208000014919 IgG4-related retroperitoneal fibrosis Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 102000002746 Inhibins Human genes 0.000 description 1
- 108010004250 Inhibins Proteins 0.000 description 1
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 125000002842 L-seryl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])O[H] 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010049694 Left Ventricular Dysfunction Diseases 0.000 description 1
- 208000005777 Lupus Nephritis Diseases 0.000 description 1
- AXUZQJFHDNNPFG-UXBLZVDNSA-N MK 571 Chemical compound CN(C)C(=O)CCSC(SCCC(O)=O)C1=CC=CC(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)=C1 AXUZQJFHDNNPFG-UXBLZVDNSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000002805 Mediastinal fibrosis Diseases 0.000 description 1
- 208000011682 Mitral valve disease Diseases 0.000 description 1
- PVLJETXTTWAYEW-UHFFFAOYSA-N Mizolastine Chemical compound N=1C=CC(=O)NC=1N(C)C(CC1)CCN1C1=NC2=CC=CC=C2N1CC1=CC=C(F)C=C1 PVLJETXTTWAYEW-UHFFFAOYSA-N 0.000 description 1
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 description 1
- 102100025725 Mothers against decapentaplegic homolog 4 Human genes 0.000 description 1
- 101710143112 Mothers against decapentaplegic homolog 4 Proteins 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- 208000002231 Muscle Neoplasms Diseases 0.000 description 1
- 208000021642 Muscular disease Diseases 0.000 description 1
- 208000009525 Myocarditis Diseases 0.000 description 1
- ONXPDKGXOOORHB-BYPYZUCNSA-N N(5)-methyl-L-glutamine Chemical compound CNC(=O)CC[C@H](N)C(O)=O ONXPDKGXOOORHB-BYPYZUCNSA-N 0.000 description 1
- GVUJBEGNEYUVDH-UHFFFAOYSA-N N-methyl-2-pyridin-2-ylbenzamide Chemical compound N1=CC=CC=C1C1=C(C(=O)NC)C=CC=C1 GVUJBEGNEYUVDH-UHFFFAOYSA-N 0.000 description 1
- 206010028851 Necrosis Diseases 0.000 description 1
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 description 1
- 206010061309 Neoplasm progression Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 1
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000283903 Ovis aries Species 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000031481 Pathologic Constriction Diseases 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 206010034650 Peritoneal adhesions Diseases 0.000 description 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 1
- 102100036829 Probable peptidyl-tRNA hydrolase Human genes 0.000 description 1
- 108010050808 Procollagen Proteins 0.000 description 1
- 208000002158 Proliferative Vitreoretinopathy Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102000016611 Proteoglycans Human genes 0.000 description 1
- 108010067787 Proteoglycans Proteins 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010067284 Pulmonary arteriopathy Diseases 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 101100437153 Rattus norvegicus Acvr2b gene Proteins 0.000 description 1
- 208000003782 Raynaud disease Diseases 0.000 description 1
- 208000012322 Raynaud phenomenon Diseases 0.000 description 1
- 206010038934 Retinopathy proliferative Diseases 0.000 description 1
- 206010038979 Retroperitoneal fibrosis Diseases 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 206010039580 Scar Diseases 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 description 1
- 201000010001 Silicosis Diseases 0.000 description 1
- 102000007374 Smad Proteins Human genes 0.000 description 1
- 108010007945 Smad Proteins Proteins 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 201000009594 Systemic Scleroderma Diseases 0.000 description 1
- 206010042953 Systemic sclerosis Diseases 0.000 description 1
- 108091005735 TGF-beta receptors Proteins 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 208000001435 Thromboembolism Diseases 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 102000016715 Transforming Growth Factor beta Receptors Human genes 0.000 description 1
- 102000011117 Transforming Growth Factor beta2 Human genes 0.000 description 1
- 102000004060 Transforming Growth Factor-beta Type II Receptor Human genes 0.000 description 1
- 108010082684 Transforming Growth Factor-beta Type II Receptor Proteins 0.000 description 1
- 101800000304 Transforming growth factor beta-2 Proteins 0.000 description 1
- 206010069363 Traumatic lung injury Diseases 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 206010057469 Vascular stenosis Diseases 0.000 description 1
- 206010058990 Venous occlusion Diseases 0.000 description 1
- 229930003316 Vitamin D Natural products 0.000 description 1
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 1
- YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 description 1
- YJBKAMMKXVRSAI-CUCKRJOPSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-(3-fluorophenyl)-n-[(3,4,5-trifluorophenyl)methyl]carbamate;(2s,3s)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O.FC1=CC=CC(N(CC=2C=C(F)C(F)=C(F)C=2)C(=O)O[C@@H]2C3CCN(CC3)C2)=C1 YJBKAMMKXVRSAI-CUCKRJOPSA-N 0.000 description 1
- CLSGMFARLQWVRZ-UHFFFAOYSA-N [3-fluoro-5-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]methanol Chemical compound OCC1=CC(F)=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC(F)=CC=2)=C1 CLSGMFARLQWVRZ-UHFFFAOYSA-N 0.000 description 1
- OUAAKHOMCQAOAC-UHFFFAOYSA-N [4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]piperidin-1-yl]-pyrrolidin-2-ylmethanone Chemical compound C1CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)CCN1C(=O)C1CCCN1 OUAAKHOMCQAOAC-UHFFFAOYSA-N 0.000 description 1
- NMBGEXLBZCQCAQ-UHFFFAOYSA-N [4-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC(F)=CC=2)C=C1 NMBGEXLBZCQCAQ-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- OMZAMQFQZMUNTP-UHFFFAOYSA-N acetic acid;1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methylindol-5-ol Chemical compound CC(O)=O.C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 OMZAMQFQZMUNTP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- YAJCHEVQCOHZDC-QMMNLEPNSA-N actrapid Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3N=CNC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@H](C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@H](C)CC)[C@H](C)CC)[C@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C(N)=O)C1=CNC=N1 YAJCHEVQCOHZDC-QMMNLEPNSA-N 0.000 description 1
- 208000024716 acute asthma Diseases 0.000 description 1
- 206010069351 acute lung injury Diseases 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 210000001132 alveolar macrophage Anatomy 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 208000000252 angiomatosis Diseases 0.000 description 1
- 238000002399 angioplasty Methods 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000011861 anti-inflammatory therapy Methods 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 229940124623 antihistamine drug Drugs 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000003434 antitussive agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 206010002906 aortic stenosis Diseases 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- GVTLDPJNRVMCAL-UHFFFAOYSA-N arofylline Chemical compound C1=2N=CNC=2C(=O)N(CCC)C(=O)N1C1=CC=C(Cl)C=C1 GVTLDPJNRVMCAL-UHFFFAOYSA-N 0.000 description 1
- 229950009746 arofylline Drugs 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- GXDALQBWZGODGZ-UHFFFAOYSA-N astemizole Chemical compound C1=CC(OC)=CC=C1CCN1CCC(NC=2N(C3=CC=CC=C3N=2)CC=2C=CC(F)=CC=2)CC1 GXDALQBWZGODGZ-UHFFFAOYSA-N 0.000 description 1
- 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 229960004574 azelastine Drugs 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 229960000817 bazedoxifene Drugs 0.000 description 1
- 229950000210 beclometasone dipropionate Drugs 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 150000005347 biaryls Chemical group 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000002617 bone density conservation agent Substances 0.000 description 1
- 229940112869 bone morphogenetic protein Drugs 0.000 description 1
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 1
- 229960002802 bromocriptine Drugs 0.000 description 1
- 230000007885 bronchoconstriction Effects 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 229960004436 budesonide Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229960004596 cabergoline Drugs 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000009787 cardiac fibrosis Effects 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000001364 causal effect Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000005754 cellular signaling Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229960004342 cetirizine hydrochloride Drugs 0.000 description 1
- CFBUZOUXXHZCFB-OYOVHJISSA-N chembl511115 Chemical compound COC1=CC=C([C@@]2(CC[C@H](CC2)C(O)=O)C#N)C=C1OC1CCCC1 CFBUZOUXXHZCFB-OYOVHJISSA-N 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 231100000012 chronic liver injury Toxicity 0.000 description 1
- 229960003728 ciclesonide Drugs 0.000 description 1
- BZMKNPGKXJAIDV-VAWYXSNFSA-N cinalukast Chemical compound CCC(CC)(C(O)=O)CC(=O)NC1=CC=CC(\C=C\C=2SC=C(N=2)C2CCC2)=C1 BZMKNPGKXJAIDV-VAWYXSNFSA-N 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229960002689 clemastine fumarate Drugs 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 208000018631 connective tissue disease Diseases 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 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 1
- 125000004090 cyclononenyl group Chemical group C1(=CCCCCCCC1)* 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- YRCPIXCRSAKRGM-UHFFFAOYSA-N cyclopentyl n-[1-[[4-(benzenesulfonylcarbamoyl)-2-methoxyphenyl]methyl]indazol-6-yl]carbamate Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=CC=C1CN(C1=C2)N=CC1=CC=C2NC(=O)OC1CCCC1 YRCPIXCRSAKRGM-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 239000000850 decongestant Substances 0.000 description 1
- 229940124581 decongestants Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- DPOGTJDEMBEUSH-UHFFFAOYSA-N dicyclohexyl(ethyl)phosphane Chemical compound C1CCCCC1P(CC)C1CCCCC1 DPOGTJDEMBEUSH-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229960001992 dimetindene Drugs 0.000 description 1
- MVMQESMQSYOVGV-UHFFFAOYSA-N dimetindene Chemical compound CN(C)CCC=1CC2=CC=CC=C2C=1C(C)C1=CC=CC=N1 MVMQESMQSYOVGV-UHFFFAOYSA-N 0.000 description 1
- 229960000525 diphenhydramine hydrochloride Drugs 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
- 230000009109 downstream regulation Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- HRKSGGJDQQUXJJ-UHFFFAOYSA-N ethyl 2-[2-fluoro-4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]phenyl]acetate Chemical compound C1=C(F)C(CC(=O)OCC)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 HRKSGGJDQQUXJJ-UHFFFAOYSA-N 0.000 description 1
- SBVYURPQULDJTI-UHFFFAOYSA-N ethyl n-[amino-[4-[[3-[[4-[2-(4-hydroxyphenyl)propan-2-yl]phenoxy]methyl]phenyl]methoxy]phenyl]methylidene]carbamate Chemical compound C1=CC(C(=N)NC(=O)OCC)=CC=C1OCC1=CC=CC(COC=2C=CC(=CC=2)C(C)(C)C=2C=CC(O)=CC=2)=C1 SBVYURPQULDJTI-UHFFFAOYSA-N 0.000 description 1
- 229960001582 fenfluramine Drugs 0.000 description 1
- JFSPBVWPKOEZCB-UHFFFAOYSA-N fenfuram Chemical compound O1C=CC(C(=O)NC=2C=CC=CC=2)=C1C JFSPBVWPKOEZCB-UHFFFAOYSA-N 0.000 description 1
- 229960001022 fenoterol Drugs 0.000 description 1
- LSLYOANBFKQKPT-UHFFFAOYSA-N fenoterol Chemical compound C=1C(O)=CC(O)=CC=1C(O)CNC(C)CC1=CC=C(O)C=C1 LSLYOANBFKQKPT-UHFFFAOYSA-N 0.000 description 1
- 229960000354 fexofenadine hydrochloride Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 description 1
- 229960000289 fluticasone propionate Drugs 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229960002848 formoterol Drugs 0.000 description 1
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 206010061989 glomerulosclerosis Diseases 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 229940124750 glucocorticoid receptor agonist Drugs 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 229940015042 glycopyrrolate Drugs 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 description 1
- 102000052842 human TGFBR1 Human genes 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 230000002390 hyperplastic effect Effects 0.000 description 1
- 230000036031 hyperthermia Effects 0.000 description 1
- 208000018875 hypoxemia Diseases 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 108700016226 indium-bleomycin Proteins 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 238000002664 inhalation therapy Methods 0.000 description 1
- 239000000893 inhibin Substances 0.000 description 1
- ZPNFWUPYTFPOJU-LPYSRVMUSA-N iniprol Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC=4C=CC=CC=4)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC2=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]2N(CCC2)C(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N2[C@@H](CCC2)C(=O)N3)C(=O)NCC(=O)NCC(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](C(=O)N1)C(C)C)[C@@H](C)O)[C@@H](C)CC)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 ZPNFWUPYTFPOJU-LPYSRVMUSA-N 0.000 description 1
- 102000006495 integrins Human genes 0.000 description 1
- 108010044426 integrins Proteins 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 229960001361 ipratropium bromide Drugs 0.000 description 1
- KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 208000011379 keloid formation Diseases 0.000 description 1
- 238000011813 knockout mouse model Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 1
- 150000002616 leukotriene B4 ethanolamides Chemical class 0.000 description 1
- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 description 1
- 229960001508 levocetirizine Drugs 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 231100000835 liver failure Toxicity 0.000 description 1
- 208000007903 liver failure Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 description 1
- 229960003088 loratadine Drugs 0.000 description 1
- 230000004199 lung function Effects 0.000 description 1
- 231100000515 lung injury Toxicity 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- NOSGKFXTZKCCNR-UHFFFAOYSA-N methyl 2-[4-[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]pyrazol-1-yl]acetate Chemical compound C1=NN(CC(=O)OC)C=C1C1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 NOSGKFXTZKCCNR-UHFFFAOYSA-N 0.000 description 1
- IHONOJCQHUFCJS-UHFFFAOYSA-N methyl 2-[[4-[3-(2-pyrazol-1-ylpyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]benzoyl]amino]acetate Chemical compound C1=CC(C(=O)NCC(=O)OC)=CC=C1C1=CN2C(C=3C=C(N=CC=3)N3N=CC=C3)=CN=C2C=C1 IHONOJCQHUFCJS-UHFFFAOYSA-N 0.000 description 1
- SVYIFRZRAGBCNU-UHFFFAOYSA-N methyl 2-[[4-[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]benzoyl]amino]acetate Chemical compound C1=CC(C(=O)NCC(=O)OC)=CC=C1C1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 SVYIFRZRAGBCNU-UHFFFAOYSA-N 0.000 description 1
- DWDJJUSKDKFJRX-UHFFFAOYSA-N methyl 3-(2-chloropyridin-4-yl)imidazo[1,2-a]pyridine-6-carboxylate Chemical compound COC(=O)c1ccc2ncc(-c3ccnc(Cl)c3)n2c1 DWDJJUSKDKFJRX-UHFFFAOYSA-N 0.000 description 1
- JACPDLJUQLKABC-UHFFFAOYSA-N methyl 6-aminopyridine-3-carboxylate Chemical compound COC(=O)C1=CC=C(N)N=C1 JACPDLJUQLKABC-UHFFFAOYSA-N 0.000 description 1
- 210000004925 microvascular endothelial cell Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 229960001144 mizolastine Drugs 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229960002744 mometasone furoate Drugs 0.000 description 1
- WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 229960005127 montelukast Drugs 0.000 description 1
- 238000000491 multivariate analysis Methods 0.000 description 1
- 201000002077 muscle cancer Diseases 0.000 description 1
- 230000009753 muscle formation Effects 0.000 description 1
- 230000004220 muscle function Effects 0.000 description 1
- 230000037257 muscle growth Effects 0.000 description 1
- SLDMANLELUCHNZ-UHFFFAOYSA-N n,n-dimethyl-3-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]aniline Chemical compound CN(C)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 SLDMANLELUCHNZ-UHFFFAOYSA-N 0.000 description 1
- JHGYWKFWHAGUON-UHFFFAOYSA-N n,n-dimethyl-5-[3-(2-pyrazol-1-ylpyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]pyridin-2-amine Chemical compound C1=NC(N(C)C)=CC=C1C1=CN2C(C=3C=C(N=CC=3)N3N=CC=C3)=CN=C2C=C1 JHGYWKFWHAGUON-UHFFFAOYSA-N 0.000 description 1
- IPKZJOQESDMKJR-UHFFFAOYSA-N n,n-dimethyl-5-[3-[2-(3-methylpyrazol-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]pyridin-2-amine Chemical compound C1=NC(N(C)C)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)N3N=C(C)C=C3)N2C=C1 IPKZJOQESDMKJR-UHFFFAOYSA-N 0.000 description 1
- NPGREARFJMFTDF-UHFFFAOYSA-N n-(3,5-dichloro-1-hydroxypyridin-4-ylidene)-8-methoxy-2-(trifluoromethyl)quinoline-5-carboxamide Chemical compound C12=CC=C(C(F)(F)F)N=C2C(OC)=CC=C1C(=O)N=C1C(Cl)=CN(O)C=C1Cl NPGREARFJMFTDF-UHFFFAOYSA-N 0.000 description 1
- DPHDSIQHVGSITN-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-2-[1-[(4-fluorophenyl)methyl]-5-hydroxyindol-3-yl]-2-oxoacetamide Chemical compound C1=C(C(=O)C(=O)NC=2C(=CN=CC=2Cl)Cl)C2=CC(O)=CC=C2N1CC1=CC=C(F)C=C1 DPHDSIQHVGSITN-UHFFFAOYSA-N 0.000 description 1
- BMKINZUHKYLSKI-DQEYMECFSA-N n-[2-hydroxy-5-[(1r)-1-hydroxy-2-[2-[4-[[(2r)-2-hydroxy-2-phenylethyl]amino]phenyl]ethylamino]ethyl]phenyl]formamide Chemical compound C1([C@@H](O)CNC2=CC=C(C=C2)CCNC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)=CC=CC=C1 BMKINZUHKYLSKI-DQEYMECFSA-N 0.000 description 1
- LXEVVEMOSGKCPR-UHFFFAOYSA-N n-[3-[3-(2-pyrazol-1-ylpyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C2=CN3C(C=4C=C(N=CC=4)N4N=CC=C4)=CN=C3C=C2)=C1 LXEVVEMOSGKCPR-UHFFFAOYSA-N 0.000 description 1
- SNPZIWJQTKPURN-UHFFFAOYSA-N n-[4-[3-(2-pyrazol-1-ylpyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CN2C(C=3C=C(N=CC=3)N3N=CC=C3)=CN=C2C=C1 SNPZIWJQTKPURN-UHFFFAOYSA-N 0.000 description 1
- QEESMQJNHOQGAU-UHFFFAOYSA-N n-[4-[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CN2C(C=3C=C(N=CC=3)C3=COC=C3)=CN=C2C=C1 QEESMQJNHOQGAU-UHFFFAOYSA-N 0.000 description 1
- GRWFIYMXWDKMFG-UHFFFAOYSA-N n-[[3-[3-(2-pyrrolidin-1-ylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]propan-2-amine Chemical compound CC(C)NCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)N2CCCC2)=C1 GRWFIYMXWDKMFG-UHFFFAOYSA-N 0.000 description 1
- BXSMJCMJQSBSGH-UHFFFAOYSA-N n-[[3-[3-[2-(2,4-difluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]-n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C(=CC(F)=CC=2)F)=C1 BXSMJCMJQSBSGH-UHFFFAOYSA-N 0.000 description 1
- HBIAERLZIXDCGC-UHFFFAOYSA-N n-[[3-[3-[2-(2,4-difluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]ethanamine Chemical compound CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C(=CC(F)=CC=2)F)=C1 HBIAERLZIXDCGC-UHFFFAOYSA-N 0.000 description 1
- AIBZBAXSTCJRPB-UHFFFAOYSA-N n-[[3-[3-[2-(2-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]-3-methylbutan-1-amine Chemical compound CC(C)CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C(=CC=CC=2)F)=C1 AIBZBAXSTCJRPB-UHFFFAOYSA-N 0.000 description 1
- DXHFGVJBZDMRFH-UHFFFAOYSA-N n-[[3-[3-[2-(2-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]ethanamine Chemical compound CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C(=CC=CC=2)F)=C1 DXHFGVJBZDMRFH-UHFFFAOYSA-N 0.000 description 1
- SOAYIRQGHACPQD-UHFFFAOYSA-N n-[[3-[3-[2-(3,3-difluoropyrrolidin-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]ethanamine Chemical compound CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)N2CC(F)(F)CC2)=C1 SOAYIRQGHACPQD-UHFFFAOYSA-N 0.000 description 1
- YWKYRDHIRFHAFD-UHFFFAOYSA-N n-[[3-[3-[2-(3-methylpyrazol-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]ethanamine Chemical class CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)N2N=C(C)C=C2)=C1 YWKYRDHIRFHAFD-UHFFFAOYSA-N 0.000 description 1
- CRSBXDPGYAGMQA-UHFFFAOYSA-N n-[[3-[3-[2-(4-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]ethanamine Chemical compound CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC(F)=CC=2)=C1 CRSBXDPGYAGMQA-UHFFFAOYSA-N 0.000 description 1
- DUUOSCSEVNOGSS-UHFFFAOYSA-N n-[[3-[3-[2-(cyclohexen-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]ethanamine Chemical compound CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2CCCCC=2)=C1 DUUOSCSEVNOGSS-UHFFFAOYSA-N 0.000 description 1
- FMRUYASNGXDWKV-UHFFFAOYSA-N n-[[3-[3-[2-(cyclopenten-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]-n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2CCCC=2)=C1 FMRUYASNGXDWKV-UHFFFAOYSA-N 0.000 description 1
- LEXHQDAXAWMKOE-UHFFFAOYSA-N n-[[3-[3-[2-(cyclopenten-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]propan-2-amine Chemical compound CC(C)NCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2CCCC=2)=C1 LEXHQDAXAWMKOE-UHFFFAOYSA-N 0.000 description 1
- ABEDNMNZZWNGKC-UHFFFAOYSA-N n-[[4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]furan-2-yl]methyl]ethanamine Chemical compound O1C(CNCC)=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 ABEDNMNZZWNGKC-UHFFFAOYSA-N 0.000 description 1
- IZLPTUWOVWIUFD-UHFFFAOYSA-N n-[[4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]propan-1-amine Chemical compound C1=CC(CNCCC)=CC=C1C1=CC2=NC=C(C=3C=C(N=CC=3)C=3C=CC=CC=3)N2C=C1 IZLPTUWOVWIUFD-UHFFFAOYSA-N 0.000 description 1
- DMFWDEPRSNUKAP-UHFFFAOYSA-N n-[[4-[3-[2-(3-fluorophenyl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]phenyl]methyl]-2-(4-methylpiperazin-1-yl)ethanamine Chemical compound C1CN(C)CCN1CCNCC1=CC=C(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=C(F)C=CC=2)C=C1 DMFWDEPRSNUKAP-UHFFFAOYSA-N 0.000 description 1
- ULGSUXKRLQOKDG-UHFFFAOYSA-N n-cyclopropyl-4-[3-(2-pyrazol-1-ylpyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonamide Chemical compound C=1C=C(C2=CN3C(C=4C=C(N=CC=4)N4N=CC=C4)=CN=C3C=C2)C=CC=1S(=O)(=O)NC1CC1 ULGSUXKRLQOKDG-UHFFFAOYSA-N 0.000 description 1
- RMFMYVYBVIVAHB-UHFFFAOYSA-N n-cyclopropyl-4-[3-[2-(furan-3-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-6-yl]benzamide Chemical compound C=1C=C(C2=CN3C(C=4C=C(N=CC=4)C4=COC=C4)=CN=C3C=C2)C=CC=1C(=O)NC1CC1 RMFMYVYBVIVAHB-UHFFFAOYSA-N 0.000 description 1
- NMEMXBXEMOPJQJ-UHFFFAOYSA-N n-ethyl-3-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]aniline Chemical compound CCNC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 NMEMXBXEMOPJQJ-UHFFFAOYSA-N 0.000 description 1
- AEKPTRGYUWHEKL-UHFFFAOYSA-N n-ethyl-5-[3-(3-pyrazol-1-ylphenyl)imidazo[1,2-a]pyridin-7-yl]pyridine-3-carboxamide Chemical compound CCNC(=O)C1=CN=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(C=CC=2)N2N=CC=C2)=C1 AEKPTRGYUWHEKL-UHFFFAOYSA-N 0.000 description 1
- KNJVXBJLDMVAIJ-UHFFFAOYSA-N n-methyl-1-[3-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]phenyl]methanamine Chemical compound CNCC1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 KNJVXBJLDMVAIJ-UHFFFAOYSA-N 0.000 description 1
- MVIKWONEGZDQPH-UHFFFAOYSA-N n-methyl-1-[4-[3-(2-phenylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]furan-2-yl]methanamine Chemical compound O1C(CNC)=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 MVIKWONEGZDQPH-UHFFFAOYSA-N 0.000 description 1
- MEKLQACUHBKVDZ-UHFFFAOYSA-N n-methyl-3-[3-(2-pyrrolidin-1-ylpyridin-4-yl)imidazo[1,2-a]pyridin-7-yl]benzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)N2CCCC2)=C1 MEKLQACUHBKVDZ-UHFFFAOYSA-N 0.000 description 1
- IVFDAUDBVLLVQE-UHFFFAOYSA-N n-methyl-3-[3-[2-(2-methylpyrrolidin-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]benzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)N2C(CCC2)C)=C1 IVFDAUDBVLLVQE-UHFFFAOYSA-N 0.000 description 1
- JQPVMCQSTOIIDL-UHFFFAOYSA-N n-methyl-3-[3-[2-(3-methylcyclopenten-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]benzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2CCC(C)C=2)=C1 JQPVMCQSTOIIDL-UHFFFAOYSA-N 0.000 description 1
- HPYTYLNRRCBHMT-UHFFFAOYSA-N n-methyl-3-[3-[2-(3-methylpyrazol-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]benzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)N2N=C(C)C=C2)=C1 HPYTYLNRRCBHMT-UHFFFAOYSA-N 0.000 description 1
- HUFYKLLDKCSYKI-UHFFFAOYSA-N n-methyl-3-[3-[2-(methylamino)-6-phenylpyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]benzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=C(NC)C=2)C=2C=CC=CC=2)=C1 HUFYKLLDKCSYKI-UHFFFAOYSA-N 0.000 description 1
- NEKHROSXWLHRHE-UHFFFAOYSA-N n-methyl-3-[3-[2-phenyl-6-(propan-2-ylamino)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]benzamide Chemical compound CNC(=O)C1=CC=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=C(NC(C)C)C=2)C=2C=CC=CC=2)=C1 NEKHROSXWLHRHE-UHFFFAOYSA-N 0.000 description 1
- OCAXEWDCOPEFAS-UHFFFAOYSA-N n-methyl-6-phenyl-4-(7-phenylimidazo[1,2-a]pyridin-3-yl)pyridin-2-amine Chemical compound N=1C(NC)=CC(C=2N3C=CC(=CC3=NC=2)C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 OCAXEWDCOPEFAS-UHFFFAOYSA-N 0.000 description 1
- NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 description 1
- CJAOCUSGKIYOEF-UHFFFAOYSA-N n-tert-butyl-4-[3-(2-pyrazol-1-ylpyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC(C)(C)C)=CC=C1C1=CN2C(C=3C=C(N=CC=3)N3N=CC=C3)=CN=C2C=C1 CJAOCUSGKIYOEF-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 208000021971 neovascular inflammatory vitreoretinopathy Diseases 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 208000014055 occupational lung disease Diseases 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 229950000175 oglemilast Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 229960002657 orciprenaline Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000002188 osteogenic effect Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NVOYVOBDTVTBDX-PMEUIYRNSA-N oxitropium Chemical compound CC[N+]1(C)[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)[C@H](CO)C1=CC=CC=C1 NVOYVOBDTVTBDX-PMEUIYRNSA-N 0.000 description 1
- 229960000797 oxitropium Drugs 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 108010073509 parathyroid hormone (1-31) Proteins 0.000 description 1
- 108010073230 parathyroid hormone (1-38) Proteins 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 208000008494 pericarditis Diseases 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 1
- 206010035653 pneumoconiosis Diseases 0.000 description 1
- 208000005987 polymyositis Diseases 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003334 potential effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 208000037920 primary disease Diseases 0.000 description 1
- 229960002288 procaterol Drugs 0.000 description 1
- FKNXQNWAXFXVNW-BLLLJJGKSA-N procaterol Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)[C@@H](NC(C)C)CC FKNXQNWAXFXVNW-BLLLJJGKSA-N 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 230000006785 proliferative vitreoretinopathy Effects 0.000 description 1
- 229960003910 promethazine Drugs 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 208000014731 pulmonary artery disease Diseases 0.000 description 1
- 210000004879 pulmonary tissue Anatomy 0.000 description 1
- 208000037813 pulmonary venous hypertension Diseases 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 1
- 229960004622 raloxifene Drugs 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229960004017 salmeterol Drugs 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 201000004409 schistosomiasis Diseases 0.000 description 1
- 208000037921 secondary disease Diseases 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 101150005548 sel gene Proteins 0.000 description 1
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 1
- 229960003946 selegiline Drugs 0.000 description 1
- 150000003355 serines Chemical group 0.000 description 1
- 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
- 208000013220 shortness of breath Diseases 0.000 description 1
- 208000007056 sickle cell anemia Diseases 0.000 description 1
- 108091006024 signal transducing proteins Proteins 0.000 description 1
- 102000034285 signal transducing proteins Human genes 0.000 description 1
- 210000002363 skeletal muscle cell Anatomy 0.000 description 1
- 230000025175 skeletal muscle hypertrophy Effects 0.000 description 1
- 230000004096 skeletal muscle tissue growth Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000036262 stenosis Effects 0.000 description 1
- 208000037804 stenosis Diseases 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960000195 terbutaline Drugs 0.000 description 1
- OGBMKVWORPGQRR-UMXFMPSGSA-N teriparatide Chemical compound C([C@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@@H](N)CO)C(C)C)[C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CNC=N1 OGBMKVWORPGQRR-UMXFMPSGSA-N 0.000 description 1
- GGYMOMSZKYBHHG-UHFFFAOYSA-N tert-butyl 4-[3-[2-(cyclopenten-1-yl)pyridin-4-yl]imidazo[1,2-a]pyridin-7-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C2=CC3=NC=C(N3C=C2)C=2C=C(N=CC=2)C=2CCCC=2)=C1 GGYMOMSZKYBHHG-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
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 230000001732 thrombotic effect Effects 0.000 description 1
- 229960001023 tibolone Drugs 0.000 description 1
- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical class O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 description 1
- 229960000257 tiotropium bromide Drugs 0.000 description 1
- 230000007838 tissue remodeling Effects 0.000 description 1
- MWYHLEQJTQJHSS-UHFFFAOYSA-N tomelukast Chemical compound C1=CC(C(C)=O)=C(O)C(CCC)=C1OCCCCC1=NNN=N1 MWYHLEQJTQJHSS-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 229940099456 transforming growth factor beta 1 Drugs 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229940062627 tribasic potassium phosphate Drugs 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 230000005751 tumor progression Effects 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 231100000216 vascular lesion Toxicity 0.000 description 1
- 201000002282 venous insufficiency Diseases 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229960004764 zafirlukast Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
- A61P17/18—Antioxidants, e.g. antiradicals
-
- 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
-
- 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
-
- 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
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
- A61P31/14—Antivirals for RNA viruses
-
- 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
- A61P31/20—Antivirals for DNA viruses
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Virology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Dermatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Endocrinology (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Psychiatry (AREA)
- Vascular Medicine (AREA)
- Biotechnology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07118726 | 2007-10-17 | ||
| EP07118726.4 | 2007-10-17 | ||
| EP08151336.8 | 2008-02-12 | ||
| EP08151336 | 2008-02-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20100076022A true KR20100076022A (ko) | 2010-07-05 |
Family
ID=39944334
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020107010615A Withdrawn KR20100076022A (ko) | 2007-10-17 | 2008-10-15 | Ａｌｋ 억제제로서 유용한 이미다조 [１,２-ａ] 피리딘 유도체 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US8367662B2 (enExample) |
| EP (1) | EP2212323B1 (enExample) |
| JP (1) | JP5456681B2 (enExample) |
| KR (1) | KR20100076022A (enExample) |
| CN (1) | CN101827844B (enExample) |
| AR (1) | AR068877A1 (enExample) |
| AU (1) | AU2008313773B2 (enExample) |
| BR (1) | BRPI0817434A2 (enExample) |
| CA (1) | CA2703037A1 (enExample) |
| CL (1) | CL2008003056A1 (enExample) |
| CO (1) | CO6270321A2 (enExample) |
| EA (1) | EA201000615A1 (enExample) |
| ES (1) | ES2393430T3 (enExample) |
| IL (1) | IL204720A0 (enExample) |
| MA (1) | MA31766B1 (enExample) |
| MX (1) | MX2010004244A (enExample) |
| PE (1) | PE20091383A1 (enExample) |
| PL (1) | PL2212323T3 (enExample) |
| PT (1) | PT2212323E (enExample) |
| TN (1) | TN2010000167A1 (enExample) |
| TW (1) | TW200922570A (enExample) |
| WO (1) | WO2009050183A2 (enExample) |
| ZA (1) | ZA201002334B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150002639A (ko) * | 2012-03-30 | 2015-01-07 | 에이전시 포 사이언스, 테크놀로지 앤드 리서치 | Mnk1 및 mnk2 조절제로서 바이시클릭 헤테로시클릭 및 이의 용도 |
| KR20220052939A (ko) * | 2019-07-26 | 2022-04-28 | 메드샤인 디스커버리 아이엔씨. | Fgfr 및 vegfr 이중 억제제로서의 피리딘 유도체 |
Families Citing this family (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8343966B2 (en) * | 2008-01-11 | 2013-01-01 | Novartis Ag | Organic compounds |
| FR2945806B1 (fr) * | 2009-05-19 | 2013-04-05 | Sanofi Aventis | Nouveaux derives imidazo[1,2-a]pyridine,procede de preparation,medicaments,compositions pharmaceutiques et utilisation notamment comme inhibiteurs de met |
| EA201170223A1 (ru) * | 2008-07-18 | 2011-08-30 | Санофи-Авентис | НОВЫЕ ПРОИЗВОДНЫЕ ИМИДАЗО[1,2-a]ПИРИДИНА, СПОСОБ ИХ ПОЛУЧЕНИЯ, ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ЛЕКАРСТВЕННЫХ СРЕДСТВ, ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ И НОВОЕ ПРИМЕНЕНИЕ, В ЧАСТНОСТИ, В КАЧЕСТВЕ ИНГИБИТОРОВ МЕТ |
| MX2011012037A (es) * | 2009-05-13 | 2012-02-28 | Amgen Inc | Compuestos de heteroarilo como inhibidores de pikk. |
| JP2012533551A (ja) * | 2009-07-15 | 2012-12-27 | アボット・ラボラトリーズ | ピロロピラジン系キナーゼ阻害薬 |
| UY33213A (es) | 2010-02-18 | 2011-09-30 | Almirall Sa | Derivados de pirazol como inhibidores de jak |
| WO2011146287A1 (en) | 2010-05-20 | 2011-11-24 | Takeda Pharmaceutical Company Limited | Pyrazolo[4,3-b]pyridine-7-amine inhibitors of alk5 |
| CN102443009B (zh) * | 2010-09-30 | 2014-04-16 | 山东轩竹医药科技有限公司 | 并环激酶抑制剂 |
| EP2463289A1 (en) | 2010-11-26 | 2012-06-13 | Almirall, S.A. | Imidazo[1,2-b]pyridazine derivatives as JAK inhibitors |
| CN103764657B (zh) * | 2011-07-01 | 2016-05-25 | 拜耳知识产权有限责任公司 | 作为alk1抑制剂的羟甲基芳基取代的吡咯并三嗪 |
| EP2554544A1 (en) | 2011-08-01 | 2013-02-06 | Almirall, S.A. | Pyridin-2(1h)-one derivatives as jak inhibitors |
| HK1203412A1 (en) | 2011-12-28 | 2015-10-30 | Global Blood Therapeutics, Inc. | Substituted heteroaryl aldehyde compounds and methods for their use in increasing tissue oxygenation |
| HRP20171665T1 (hr) * | 2011-12-28 | 2017-12-15 | Global Blood Therapeutics, Inc. | Supstituirani spojevi benzaldehida i metode za njihovu primjenu u povećanju oksigenacije tkiva |
| US10280168B2 (en) | 2012-03-30 | 2019-05-07 | Agency For Science, Technology And Research | Bicyclic heteroaryl derivatives as MNK1 and MNK2 modulators and uses thereof |
| ES2984771T3 (es) | 2012-06-13 | 2024-10-31 | Incyte Holdings Corp | Compuestos tricíclicos sustituidos como inhibidores de FGFR |
| ES2660051T3 (es) * | 2012-09-28 | 2018-03-20 | Vanderbilt University | Compuestos heterocíclicos condensados como inhibidores selectivos de BMP |
| US9422279B2 (en) | 2013-03-15 | 2016-08-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US10100043B2 (en) | 2013-03-15 | 2018-10-16 | Global Blood Therapeutics, Inc. | Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation |
| CA2902711C (en) | 2013-03-15 | 2021-07-06 | Global Blood Therapeutics, Inc. | Substituted pyridinyl-6-methoxy-2-hydroxybenzaldehyde derivatives and pharmaceutical compositions thereof useful for the modulation of hemoglobin |
| US10266551B2 (en) | 2013-03-15 | 2019-04-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US8952171B2 (en) | 2013-03-15 | 2015-02-10 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9604999B2 (en) | 2013-03-15 | 2017-03-28 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9458139B2 (en) | 2013-03-15 | 2016-10-04 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| PE20161035A1 (es) | 2013-03-15 | 2016-11-13 | Global Blood Therapeutics Inc | Compuestos y usos de estos para la modulacion de la hemoglobina |
| EP2970308B1 (en) | 2013-03-15 | 2021-07-14 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9802900B2 (en) | 2013-03-15 | 2017-10-31 | Global Blood Therapeutics, Inc. | Bicyclic heteroaryl compounds and uses thereof for the modulation of hemoglobin |
| US20140274961A1 (en) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| EA035095B1 (ru) | 2013-04-19 | 2020-04-27 | Инсайт Холдингс Корпорейшн | Бициклические гетероциклы в качестве ингибиторов fgfr |
| WO2015031285A1 (en) * | 2013-08-27 | 2015-03-05 | Global Blood Therapeutics, Inc. | Crystalline 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde ansolvate salts |
| EA201992707A1 (ru) | 2013-11-18 | 2020-06-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| AP2016009261A0 (en) | 2014-02-07 | 2016-06-30 | Global Blood Therapeutics Inc | Crystalline polymorphs of the free base of 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| MA41841A (fr) | 2015-03-30 | 2018-02-06 | Global Blood Therapeutics Inc | Composés aldéhyde pour le traitement de la fibrose pulmonaire, de l'hypoxie, et de maladies auto-immunes et des tissus conjonctifs |
| AU2016305513A1 (en) | 2015-08-11 | 2018-03-08 | Neomed Institute | Aryl-substituted dihydroquinolinones, their preparation and their use as pharmaceuticals |
| WO2017024406A1 (en) | 2015-08-11 | 2017-02-16 | Neomed Institute | N-substituted bicyclic lactams, their preparation and their use as pharmaceuticals |
| JP6912039B2 (ja) | 2015-08-12 | 2021-07-28 | ネオメド インスティテュートＮｅｏｍｅｄ Ｉｎｓｔｉｔｕｔｅ | 置換ベンゾイミダゾール、それらの調製及び医薬品としてのそれらの使用 |
| US10501459B2 (en) | 2015-10-21 | 2019-12-10 | Neomed Institute | Substituted imidazo[1,2-a]pyridines as bromodomain inhibitors |
| DK3383392T3 (da) | 2015-12-04 | 2025-08-18 | Global Blood Therapeutics Inc | Doseringsskema for 2.HYDROXY.6.((2.(1.ISOPROPYL.1H.PYRAZOL.5.YL)PYRIDIN.3.YL)METHOXY)BENZALDEHYD |
| US10519151B2 (en) | 2016-01-28 | 2019-12-31 | Neomed Institute | Substituted [1,2,4]triazolo[4,3-A]pyridines, their preparation and their use as pharmaceuticals |
| TWI752307B (zh) | 2016-05-12 | 2022-01-11 | 美商全球血液治療公司 | 新穎化合物及製造化合物之方法 |
| US11352328B2 (en) | 2016-07-12 | 2022-06-07 | Arisan Therapeutics Inc. | Heterocyclic compounds for the treatment of arenavirus |
| JP2019533643A (ja) * | 2016-09-14 | 2019-11-21 | ヴァンダービルト ユニバーシティーＶａｎｄｅｒｂｉｌｔ Ｕｎｉｖｅｒｓｉｔｙ | Ｂｍｐシグナル伝達の阻害、その化合物、組成物および使用 |
| TW202332423A (zh) | 2016-10-12 | 2023-08-16 | 美商全球血液治療公司 | 包含2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)-苯甲醛之片劑 |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| IL312674A (en) | 2018-01-29 | 2024-07-01 | Merck Patent Gmbh | GCN2 inhibitors and uses thereof |
| WO2019178383A1 (en) | 2018-03-14 | 2019-09-19 | Vanderbilt University | Inhibition of bmp signaling, compounds, compositions and uses thereof |
| RS66310B1 (sr) | 2018-05-04 | 2025-01-31 | Incyte Corp | Čvrsti oblici inhibitora fgfr i procesi za njegovu pripremu |
| US11174257B2 (en) | 2018-05-04 | 2021-11-16 | Incyte Corporation | Salts of an FGFR inhibitor |
| US11014884B2 (en) | 2018-10-01 | 2021-05-25 | Global Blood Therapeutics, Inc. | Modulators of hemoglobin |
| US12419865B2 (en) | 2018-12-06 | 2025-09-23 | Arisan Therapeutics Inc. | Compounds for the treatment of arenavirus infection |
| AU2019401649B2 (en) * | 2018-12-20 | 2025-08-28 | Incyte Corporation | Imidazopyridazine and imidazopyridine compounds as inhibitors of activin receptor-like kinase-2 |
| WO2020185532A1 (en) | 2019-03-08 | 2020-09-17 | Incyte Corporation | Methods of treating cancer with an fgfr inhibitor |
| WO2021007269A1 (en) | 2019-07-09 | 2021-01-14 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| JP7395723B2 (ja) | 2019-10-02 | 2023-12-11 | トルレモ・セラピューティクス・アクチェンゲゼルシャフト | 複素環式誘導体、医薬組成物および癌の処置または寛解におけるそれらの使用 |
| US11566028B2 (en) | 2019-10-16 | 2023-01-31 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| AU2020395185A1 (en) | 2019-12-04 | 2022-06-02 | Incyte Corporation | Derivatives of an FGFR inhibitor |
| EP4069696A1 (en) | 2019-12-04 | 2022-10-12 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| CN111116582B (zh) * | 2019-12-18 | 2022-07-29 | 大连大学 | 一种mGluR2拮抗剂 |
| US20230076057A1 (en) * | 2019-12-19 | 2023-03-09 | Universite De Strasbourg | Sigma-1 receptor ligands and therapeutic uses thereof |
| EP4087657A1 (en) | 2020-01-08 | 2022-11-16 | Synthis Therapeutics, Inc. | Alk5 inhibitor conjugates and uses thereof |
| US12012409B2 (en) | 2020-01-15 | 2024-06-18 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| CN114728965B (zh) * | 2020-01-21 | 2024-05-28 | 四川科伦博泰生物医药股份有限公司 | 吡啶并杂环类化合物、其制备方法及用途 |
| WO2021252781A1 (en) | 2020-06-12 | 2021-12-16 | Incyte Corporation | Imidazopyridazine compounds with activity as alk2 inhibitors |
| BR112022026186A2 (pt) | 2020-06-25 | 2023-01-17 | Tolremo Therapeutics Ag | Combinação de um inibidor de bromodomínio cbp/p300 e um inibidor de kras |
| IL299338A (en) * | 2020-06-25 | 2023-02-01 | Tolremo Therapeutics Ag | Heterocyclic derivatives, pharmaceutical preparations and their use for the treatment, amelioration or prevention of fibrotic disease |
| CN116096719B (zh) | 2020-07-15 | 2025-09-30 | 奇斯药制品公司 | 作为alk5抑制剂的哒嗪基氨基衍生物 |
| US20240116947A1 (en) | 2020-07-15 | 2024-04-11 | Chiesi Farmaceutici S.P.A. | Pyrido oxazine derivatives as alk5 inhibitors |
| KR20230041003A (ko) | 2020-07-15 | 2023-03-23 | 키에시 파르마슈티시 엣스. 피. 에이. | Alk5 억제제로서 피리도 옥사진 아미노 유도체 |
| US20240116948A1 (en) | 2020-12-23 | 2024-04-11 | Chiesi Farmaceutici S.P.A. | Pyrido oxazine derivatives as alk5 inhibitors |
| AU2022213682C1 (en) * | 2021-01-26 | 2025-04-17 | Cgenetech (Suzhou, China) Co., Ltd | Crystal form of methylpyrazole-substituted pyridoimidazole compound and preparation method therefor |
| JP2024513575A (ja) | 2021-04-12 | 2024-03-26 | インサイト・コーポレイション | Ｆｇｆｒ阻害剤及びネクチン－４標的化剤を含む併用療法 |
| TW202313610A (zh) | 2021-06-09 | 2023-04-01 | 美商英塞特公司 | 作為ｆｇｆｒ抑制劑之三環雜環 |
| WO2022261160A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| AU2022351219A1 (en) | 2021-09-21 | 2024-05-02 | Chiesi Farmaceutici S.P.A. | Pyridazinyl amino derivatives as alk5 inhibitors |
| AU2022359801A1 (en) | 2021-10-04 | 2024-02-01 | Forx Therapeutics Ag | Parg inhibitory compounds |
| EP4514802A1 (en) | 2022-04-27 | 2025-03-05 | Chiesi Farmaceutici S.p.A. | Imidazole derivatives as alk5 inhibitors |
| WO2024074497A1 (en) | 2022-10-03 | 2024-04-11 | Forx Therapeutics Ag | Parg inhibitory compound |
| WO2024209035A1 (en) | 2023-04-05 | 2024-10-10 | Forx Therapeutics Ag | Parg inhibitory compounds |
| WO2024258967A1 (en) | 2023-06-13 | 2024-12-19 | Synthis Therapeutics, Inc. | Anti-cd5 antibodies and their uses |
| WO2025073870A1 (en) | 2023-10-03 | 2025-04-10 | Forx Therapeutics Ag | Parg inhibitory compound |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1016489B (it) | 1974-03-18 | 1977-05-30 | Isf Spa | Inalatore |
| DE59605366D1 (de) | 1995-12-07 | 2000-07-06 | Jago Pharma Ag Muttenz | Inhalator zur mehrfachen dosisweisen abgabe eines pharmakologischen trockenpulvers |
| ES2172763T3 (es) | 1996-02-21 | 2002-10-01 | Schering Corp | Inhalador de medicamento en polvo. |
| GB9927687D0 (en) * | 1999-11-23 | 2000-01-19 | Merck Sharp & Dohme | Therapeutic agents |
| DE10117183A1 (de) * | 2001-04-05 | 2002-10-10 | Gruenenthal Gmbh | Verwendung von substituierten Imidazo[1,2-a]-pyridinverbindungen als Arzneimittel |
| ATE402164T1 (de) * | 2001-04-26 | 2008-08-15 | Eisai R&D Man Co Ltd | Stickstoffhaltige verbindung mit kondensiertem ring und pyrazolylgruppe als substituent und medizinische zusammensetzung davon |
| GB0128499D0 (en) * | 2001-11-28 | 2002-01-23 | Merck Sharp & Dohme | Therapeutic agents |
| AU2003241326B2 (en) * | 2002-05-02 | 2008-05-01 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| GB0217783D0 (en) | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Compounds |
| AR040726A1 (es) * | 2002-07-31 | 2005-04-20 | Smithkline Beecham Corp | Compuesto de 2- fenilpiridin-4-il-heterociclico, composicion farmaceutica que lo comprende y su uso para la fabricacion de un medicamento |
| GB2407042B (en) | 2003-10-17 | 2007-10-24 | Vectura Ltd | Inhaler |
| GB0410712D0 (en) | 2004-05-13 | 2004-06-16 | Novartis Ag | Organic compounds |
| AU2005278292B2 (en) * | 2004-08-31 | 2011-09-08 | Msd K.K. | Novel substituted imidazole derivatives |
| WO2006044509A2 (en) * | 2004-10-15 | 2006-04-27 | Biogen Idec Ma Inc. | Methods of treating vascular injuries |
| DOP2006000051A (es) * | 2005-02-24 | 2006-08-31 | Lilly Co Eli | Inhibidores de vegf-r2 y métodos |
| HRP20150642T1 (hr) * | 2006-12-22 | 2015-08-14 | Astex Therapeutics Limited | BICIKLIÄŚKE HETEROCIKLIÄŚKE TVARI KAO INHIBITORI FGFR-a |
-
2008
- 2008-10-15 JP JP2010529359A patent/JP5456681B2/ja not_active Expired - Fee Related
- 2008-10-15 EP EP08838625A patent/EP2212323B1/en active Active
- 2008-10-15 KR KR1020107010615A patent/KR20100076022A/ko not_active Withdrawn
- 2008-10-15 BR BRPI0817434-2A patent/BRPI0817434A2/pt not_active IP Right Cessation
- 2008-10-15 PT PT08838625T patent/PT2212323E/pt unknown
- 2008-10-15 AR ARP080104492A patent/AR068877A1/es unknown
- 2008-10-15 WO PCT/EP2008/063841 patent/WO2009050183A2/en not_active Ceased
- 2008-10-15 US US12/679,549 patent/US8367662B2/en not_active Expired - Fee Related
- 2008-10-15 AU AU2008313773A patent/AU2008313773B2/en not_active Ceased
- 2008-10-15 PE PE2008001769A patent/PE20091383A1/es not_active Application Discontinuation
- 2008-10-15 CN CN2008801122032A patent/CN101827844B/zh not_active Expired - Fee Related
- 2008-10-15 MX MX2010004244A patent/MX2010004244A/es active IP Right Grant
- 2008-10-15 PL PL08838625T patent/PL2212323T3/pl unknown
- 2008-10-15 CA CA2703037A patent/CA2703037A1/en not_active Abandoned
- 2008-10-15 ES ES08838625T patent/ES2393430T3/es active Active
- 2008-10-15 EA EA201000615A patent/EA201000615A1/ru unknown
- 2008-10-16 TW TW097139735A patent/TW200922570A/zh unknown
- 2008-10-16 CL CL2008003056A patent/CL2008003056A1/es unknown
-
2010
- 2010-03-25 IL IL204720A patent/IL204720A0/en unknown
- 2010-04-01 ZA ZA2010/02334A patent/ZA201002334B/en unknown
- 2010-04-08 MA MA32756A patent/MA31766B1/fr unknown
- 2010-04-16 TN TN2010000167A patent/TN2010000167A1/fr unknown
- 2010-05-11 CO CO10056124A patent/CO6270321A2/es not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150002639A (ko) * | 2012-03-30 | 2015-01-07 | 에이전시 포 사이언스, 테크놀로지 앤드 리서치 | Mnk1 및 mnk2 조절제로서 바이시클릭 헤테로시클릭 및 이의 용도 |
| KR20220052939A (ko) * | 2019-07-26 | 2022-04-28 | 메드샤인 디스커버리 아이엔씨. | Fgfr 및 vegfr 이중 억제제로서의 피리딘 유도체 |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0817434A2 (pt) | 2015-06-16 |
| TW200922570A (en) | 2009-06-01 |
| CO6270321A2 (es) | 2011-04-20 |
| MA31766B1 (fr) | 2010-10-01 |
| PL2212323T3 (pl) | 2013-01-31 |
| CN101827844A (zh) | 2010-09-08 |
| PT2212323E (pt) | 2012-11-27 |
| WO2009050183A2 (en) | 2009-04-23 |
| AU2008313773A8 (en) | 2010-04-29 |
| CN101827844B (zh) | 2013-08-14 |
| MX2010004244A (es) | 2010-04-30 |
| AU2008313773B2 (en) | 2012-04-12 |
| PE20091383A1 (es) | 2009-10-17 |
| AR068877A1 (es) | 2009-12-09 |
| EP2212323A2 (en) | 2010-08-04 |
| ZA201002334B (en) | 2011-03-30 |
| EP2212323B1 (en) | 2012-08-15 |
| US20100210641A1 (en) | 2010-08-19 |
| US8367662B2 (en) | 2013-02-05 |
| IL204720A0 (en) | 2010-11-30 |
| JP5456681B2 (ja) | 2014-04-02 |
| TN2010000167A1 (en) | 2011-11-11 |
| CA2703037A1 (en) | 2009-04-23 |
| WO2009050183A3 (en) | 2009-07-16 |
| ES2393430T3 (es) | 2012-12-21 |
| CL2008003056A1 (es) | 2009-07-31 |
| JP2011500623A (ja) | 2011-01-06 |
| EA201000615A1 (ru) | 2010-12-30 |
| AU2008313773A1 (en) | 2009-04-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5456681B2 (ja) | ＡＬＫ阻害剤として有用なイミダゾ［１，２−ａ］ピリジン誘導体 | |
| EP2307402B1 (en) | Imidazo-pyridine derivatives as activin-like receptor kinase (alk4 or alk5) inhibitors | |
| JP5090528B2 (ja) | ＡＬＫ４またはＡＬＫ５が介在する疾患を処置するための２、３、７位置換イミダゾ［１，２−ｂ］ピリダジン類 | |
| JP5643110B2 (ja) | ピロロピリミジン類およびピロロピリジン類 | |
| JP5566909B2 (ja) | ピリジン誘導体 | |
| US8431578B2 (en) | Organic compounds | |
| JP2010508315A (ja) | 抗炎症剤としてのヘテロ環式化合物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20100514 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |