JP2012525336A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2012525336A5 JP2012525336A5 JP2012507475A JP2012507475A JP2012525336A5 JP 2012525336 A5 JP2012525336 A5 JP 2012525336A5 JP 2012507475 A JP2012507475 A JP 2012507475A JP 2012507475 A JP2012507475 A JP 2012507475A JP 2012525336 A5 JP2012525336 A5 JP 2012525336A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- inden
- oxo
- dihydropyridine
- carboxamide
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims 44
- -1 R 13 Chemical compound 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- 239000012453 solvate Substances 0.000 claims 15
- 239000000203 mixture Substances 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims 7
- 125000004404 heteroalkyl group Chemical group 0.000 claims 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 7
- 102000006495 integrins Human genes 0.000 claims 6
- 108010044426 integrins Proteins 0.000 claims 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 230000027455 binding Effects 0.000 claims 4
- 150000003857 carboxamides Chemical class 0.000 claims 4
- 239000003446 ligand Substances 0.000 claims 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- MGTSRKSZRYSNRG-UHFFFAOYSA-N 1-(4-bromo-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(Br)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 MGTSRKSZRYSNRG-UHFFFAOYSA-N 0.000 claims 3
- WBJYXSTVRZMYHR-UHFFFAOYSA-N 1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-(4-phenoxyphenyl)pyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 WBJYXSTVRZMYHR-UHFFFAOYSA-N 0.000 claims 3
- DLWITLRKVVCPBW-UHFFFAOYSA-N 1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 DLWITLRKVVCPBW-UHFFFAOYSA-N 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 238000000099 in vitro assay Methods 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229930192474 thiophene Natural products 0.000 claims 3
- WFOKKBXIFGWUGP-UHFFFAOYSA-N 1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-(4-phenylphenyl)pyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC(C=C1)=CC=C1C1=CC=CC=C1 WFOKKBXIFGWUGP-UHFFFAOYSA-N 0.000 claims 2
- BYQYNXXZYYARKU-UHFFFAOYSA-N 1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-phenylpyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C(=CC=C3)N3CCOCC3)CC2)C(=O)C=1C(=O)NC1=CC=CC=C1 BYQYNXXZYYARKU-UHFFFAOYSA-N 0.000 claims 2
- NOXXXWUZNCFIGU-UHFFFAOYSA-N 1-(6-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C12=CC(OC)=CC=C2CCC1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 NOXXXWUZNCFIGU-UHFFFAOYSA-N 0.000 claims 2
- 102000016359 Fibronectins Human genes 0.000 claims 2
- 108010067306 Fibronectins Proteins 0.000 claims 2
- 238000003556 assay Methods 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- CCKYEVWPJBLGSL-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=CC=CC=C3CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 CCKYEVWPJBLGSL-UHFFFAOYSA-N 0.000 claims 1
- FHSNQTUPSULWBN-UHFFFAOYSA-N 1-(3-methyl-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C12=CC=CC=C2C(C)CC1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 FHSNQTUPSULWBN-UHFFFAOYSA-N 0.000 claims 1
- XFVUNFLEGLIUBD-UHFFFAOYSA-N 1-(4-acetamido-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(NC(=O)C)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 XFVUNFLEGLIUBD-UHFFFAOYSA-N 0.000 claims 1
- GOEROXFHACADLC-UHFFFAOYSA-N 1-(4-amino-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(N)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 GOEROXFHACADLC-UHFFFAOYSA-N 0.000 claims 1
- WOJIKDNMHKTBQP-UHFFFAOYSA-N 1-(4-bromo-2,3-dihydro-1h-inden-1-yl)-n-(4-chlorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2Br)=C2CC1 WOJIKDNMHKTBQP-UHFFFAOYSA-N 0.000 claims 1
- FNFRZOUOMFBWCP-UHFFFAOYSA-N 1-(4-chloro-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(Cl)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 FNFRZOUOMFBWCP-UHFFFAOYSA-N 0.000 claims 1
- KPWKCFBQCLGQGD-UHFFFAOYSA-N 1-(4-cyano-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C(=CC=C3)C#N)CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 KPWKCFBQCLGQGD-UHFFFAOYSA-N 0.000 claims 1
- KPLCFCSBJAOAAU-UHFFFAOYSA-N 1-(4-cyclopropyl-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C(=CC=C3)C3CC3)CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 KPLCFCSBJAOAAU-UHFFFAOYSA-N 0.000 claims 1
- PQLTUTXADSMBCD-UHFFFAOYSA-N 1-(4-hydroxy-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-(4-phenylphenyl)pyridine-3-carboxamide Chemical compound C1CC=2C(O)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC(C=C1)=CC=C1C1=CC=CC=C1 PQLTUTXADSMBCD-UHFFFAOYSA-N 0.000 claims 1
- VXPGVFBGQUKIRD-UHFFFAOYSA-N 1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(OC(F)(F)F)C=C1 VXPGVFBGQUKIRD-UHFFFAOYSA-N 0.000 claims 1
- ZWTIJGFALYXVJT-UHFFFAOYSA-N 1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-phenylpyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=CC=C1 ZWTIJGFALYXVJT-UHFFFAOYSA-N 0.000 claims 1
- SNCIYGCAKRMIIC-UHFFFAOYSA-N 1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-n-[4-(2-methoxyphenyl)phenyl]-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC(C=C1)=CC=C1C1=CC=CC=C1OC SNCIYGCAKRMIIC-UHFFFAOYSA-N 0.000 claims 1
- MDKSZGHWXVNNHA-UHFFFAOYSA-N 1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-n-[4-(4-methoxyphenoxy)phenyl]-2-oxopyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1OC(C=C1)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2OC)=C2CC1 MDKSZGHWXVNNHA-UHFFFAOYSA-N 0.000 claims 1
- JVBDRUXNLPUACH-UHFFFAOYSA-N 1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-n-[4-(4-methoxyphenyl)phenyl]-2-oxopyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C(C=C1)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2OC)=C2CC1 JVBDRUXNLPUACH-UHFFFAOYSA-N 0.000 claims 1
- RBHNCUWUVWCSAY-UHFFFAOYSA-N 1-(4-methyl-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(C)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 RBHNCUWUVWCSAY-UHFFFAOYSA-N 0.000 claims 1
- IQQACCNUSCXUCA-UHFFFAOYSA-N 1-(4-methylsulfanyl-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(SC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 IQQACCNUSCXUCA-UHFFFAOYSA-N 0.000 claims 1
- MSJRPOFHRHBTEH-UHFFFAOYSA-N 1-(4-methylsulfonyl-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(S(=O)(=O)C)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 MSJRPOFHRHBTEH-UHFFFAOYSA-N 0.000 claims 1
- FQGJWZPCMJLUFK-UHFFFAOYSA-N 1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-(4-phenoxyphenyl)pyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C(=CC=C3)N3CCOCC3)CC2)C(=O)C=1C(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 FQGJWZPCMJLUFK-UHFFFAOYSA-N 0.000 claims 1
- OMZUTCXYMPZTTO-UHFFFAOYSA-N 1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCOCC3)=C2CC1 OMZUTCXYMPZTTO-UHFFFAOYSA-N 0.000 claims 1
- OLISEGVDHLJMND-UHFFFAOYSA-N 1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-[4-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCOCC3)=C2CC1 OLISEGVDHLJMND-UHFFFAOYSA-N 0.000 claims 1
- YCIZPTKCERATII-UHFFFAOYSA-N 1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C(=CC=C3)N3CCOCC3)CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 YCIZPTKCERATII-UHFFFAOYSA-N 0.000 claims 1
- MYVYMEPVMOHNMF-UHFFFAOYSA-N 1-(4-nitro-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C([N+](=O)[O-])=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 MYVYMEPVMOHNMF-UHFFFAOYSA-N 0.000 claims 1
- QIUSZEHWTSLBQF-UHFFFAOYSA-N 1-(6-bromo-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C12=CC(Br)=CC=C2CCC1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 QIUSZEHWTSLBQF-UHFFFAOYSA-N 0.000 claims 1
- BGQSTCMBYRTACM-UHFFFAOYSA-N 1-(6-bromo-2,3-dihydro-1h-inden-1-yl)-n-(4-chlorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C2=CC(Br)=CC=C2CC1 BGQSTCMBYRTACM-UHFFFAOYSA-N 0.000 claims 1
- RAWJRBXOODIXOY-UHFFFAOYSA-N 1-(7,8-dihydro-6h-cyclopenta[g][1,3]benzodioxol-6-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C=4OCOC=4C=C3)CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 RAWJRBXOODIXOY-UHFFFAOYSA-N 0.000 claims 1
- UUBVYYFMGGHBAK-UHFFFAOYSA-N 1-(7-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1=2C(OC)=CC=CC=2CCC1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 UUBVYYFMGGHBAK-UHFFFAOYSA-N 0.000 claims 1
- CCKYEVWPJBLGSL-GOSISDBHSA-N 1-[(1r)-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN([C@H]2C3=CC=CC=C3CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 CCKYEVWPJBLGSL-GOSISDBHSA-N 0.000 claims 1
- WQDDRSUCGRFFEB-ZWKOTPCHSA-N 1-[(1r,2s)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound O=C1N([C@@H]2C3=CC=CC=C3C[C@@H]2O)C=CC=C1C(=O)NC1=CC=NC=C1 WQDDRSUCGRFFEB-ZWKOTPCHSA-N 0.000 claims 1
- CCKYEVWPJBLGSL-SFHVURJKSA-N 1-[(1s)-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN([C@@H]2C3=CC=CC=C3CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 CCKYEVWPJBLGSL-SFHVURJKSA-N 0.000 claims 1
- WQDDRSUCGRFFEB-MSOLQXFVSA-N 1-[(1s,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound O=C1N([C@H]2C3=CC=CC=C3C[C@H]2O)C=CC=C1C(=O)NC1=CC=NC=C1 WQDDRSUCGRFFEB-MSOLQXFVSA-N 0.000 claims 1
- QRKJFFQWCLAZIT-UHFFFAOYSA-N 1-[4-(4-acetylpiperazin-1-yl)-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CN(C(=O)C)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CN=CC=2)=CC=C1 QRKJFFQWCLAZIT-UHFFFAOYSA-N 0.000 claims 1
- NRVCMCNZPQSNPP-UHFFFAOYSA-N 1-[4-(4-hydroxypiperidin-1-yl)-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC(O)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CN=CC=2)=CC=C1 NRVCMCNZPQSNPP-UHFFFAOYSA-N 0.000 claims 1
- ICPVZTPGZXVHTQ-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CN(C)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CN=CC=2)=CC=C1 ICPVZTPGZXVHTQ-UHFFFAOYSA-N 0.000 claims 1
- XCCQYAUZLYVYON-UHFFFAOYSA-N 1-[4-(cyclopropylamino)-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C(=CC=C3)NC3CC3)CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 XCCQYAUZLYVYON-UHFFFAOYSA-N 0.000 claims 1
- MUZKIXYETQBYFS-UHFFFAOYSA-N 1-[4-(dimethylamino)-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(N(C)C)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 MUZKIXYETQBYFS-UHFFFAOYSA-N 0.000 claims 1
- URUJZJKZXLMCCO-UHFFFAOYSA-N 1-[4-(methylamino)-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(NC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 URUJZJKZXLMCCO-UHFFFAOYSA-N 0.000 claims 1
- DOVUJQMOXPYQMQ-UHFFFAOYSA-N 1-[4-(methylcarbamoyl)-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(C(=O)NC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 DOVUJQMOXPYQMQ-UHFFFAOYSA-N 0.000 claims 1
- KKYCOCFTHSEGSX-UHFFFAOYSA-N 1-[4-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-(4-phenylphenyl)pyridine-3-carboxamide Chemical compound C1CC=2C(OCCOCCOCCO)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC(C=C1)=CC=C1C1=CC=CC=C1 KKYCOCFTHSEGSX-UHFFFAOYSA-N 0.000 claims 1
- XUWPENNWWFSKNQ-UHFFFAOYSA-N 1-[4-[4-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]acetyl]piperazin-1-yl]-2,3-dihydro-1h-inden-1-yl]-n-(4-chlorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1CN(C(=O)COCCOCCOCCN)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CC(Cl)=CC=2)=CC=C1 XUWPENNWWFSKNQ-UHFFFAOYSA-N 0.000 claims 1
- TYNSEQWDCJNOFZ-UHFFFAOYSA-N 2-oxo-1-(4-phenyl-2,3-dihydro-1h-inden-1-yl)-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C(=CC=C3)C=3C=CC=CC=3)CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 TYNSEQWDCJNOFZ-UHFFFAOYSA-N 0.000 claims 1
- DBTUKGQQHXXZRH-UHFFFAOYSA-N 2-oxo-1-(4-piperazin-1-yl-2,3-dihydro-1h-inden-1-yl)-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C(=CC=C3)N3CCNCC3)CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 DBTUKGQQHXXZRH-UHFFFAOYSA-N 0.000 claims 1
- UPUNKRHTHQKKLY-UHFFFAOYSA-N 2-oxo-1-(4-propan-2-yloxy-2,3-dihydro-1h-inden-1-yl)-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(OC(C)C)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 UPUNKRHTHQKKLY-UHFFFAOYSA-N 0.000 claims 1
- MMPSZOGBQOYPSL-UHFFFAOYSA-N 2-oxo-n-pyridin-4-yl-1-(4-pyridin-3-yl-2,3-dihydro-1h-inden-1-yl)pyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C(=CC=C3)C=3C=NC=CC=3)CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 MMPSZOGBQOYPSL-UHFFFAOYSA-N 0.000 claims 1
- UKVNNYDWFGPHLQ-UHFFFAOYSA-N 2-oxo-n-pyridin-4-yl-1-[4-(trifluoromethoxy)-2,3-dihydro-1h-inden-1-yl]pyridine-3-carboxamide Chemical compound C1CC=2C(OC(F)(F)F)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 UKVNNYDWFGPHLQ-UHFFFAOYSA-N 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 102000004264 Osteopontin Human genes 0.000 claims 1
- 108010081689 Osteopontin Proteins 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 claims 1
- 102100023543 Vascular cell adhesion protein 1 Human genes 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000012875 competitive assay Methods 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- KZIJJWKMBXYYTH-UHFFFAOYSA-N n-(3,4-difluorophenyl)-1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(F)C(F)=C1 KZIJJWKMBXYYTH-UHFFFAOYSA-N 0.000 claims 1
- QSSHCHGMGGSIMU-UHFFFAOYSA-N n-(3,4-difluorophenyl)-1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1=C(F)C(F)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCOCC3)=C2CC1 QSSHCHGMGGSIMU-UHFFFAOYSA-N 0.000 claims 1
- BMXFFTVPJAGAJF-UHFFFAOYSA-N n-(4,4-difluorocyclohexyl)-1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1CCC(F)(F)CC1 BMXFFTVPJAGAJF-UHFFFAOYSA-N 0.000 claims 1
- YVGJXLHSJWYZIG-UHFFFAOYSA-N n-(4,4-difluorocyclohexyl)-1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC(F)(F)CCC1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCOCC3)=C2CC1 YVGJXLHSJWYZIG-UHFFFAOYSA-N 0.000 claims 1
- JTWIFVZROQHSFK-UHFFFAOYSA-N n-(4-bromophenyl)-1-(4-hydroxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(O)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(Br)C=C1 JTWIFVZROQHSFK-UHFFFAOYSA-N 0.000 claims 1
- TUYLNPCHEGGGNQ-UHFFFAOYSA-N n-(4-bromophenyl)-1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(Br)C=C1 TUYLNPCHEGGGNQ-UHFFFAOYSA-N 0.000 claims 1
- FYXQPROIXXPHNK-UHFFFAOYSA-N n-(4-bromophenyl)-1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(Br)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCOCC3)=C2CC1 FYXQPROIXXPHNK-UHFFFAOYSA-N 0.000 claims 1
- IWSACEXKDIDSSW-UHFFFAOYSA-N n-(4-bromophenyl)-1-[4-(2-hydroxyethoxy)-2,3-dihydro-1h-inden-1-yl]-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OCCO)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(Br)C=C1 IWSACEXKDIDSSW-UHFFFAOYSA-N 0.000 claims 1
- CMAUXRHGSUFQHT-UHFFFAOYSA-N n-(4-bromophenyl)-1-[4-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-2,3-dihydro-1h-inden-1-yl]-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OCCOCCOCCO)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(Br)C=C1 CMAUXRHGSUFQHT-UHFFFAOYSA-N 0.000 claims 1
- PQXYVIURQPDYJN-UHFFFAOYSA-N n-(4-bromophenyl)-2-oxo-1-(4-piperazin-1-yl-2,3-dihydro-1h-inden-1-yl)pyridine-3-carboxamide Chemical compound C1=CC(Br)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCNCC3)=C2CC1 PQXYVIURQPDYJN-UHFFFAOYSA-N 0.000 claims 1
- GPYKSKBWPPOLEF-UHFFFAOYSA-N n-(4-chlorophenyl)-1-(2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C2=CC=CC=C2CC1 GPYKSKBWPPOLEF-UHFFFAOYSA-N 0.000 claims 1
- DOQNWQCYXSGTBE-UHFFFAOYSA-N n-(4-chlorophenyl)-1-(3-methyl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C12=CC=CC=C2C(C)CC1N(C1=O)C=CC=C1C(=O)NC1=CC=C(Cl)C=C1 DOQNWQCYXSGTBE-UHFFFAOYSA-N 0.000 claims 1
- YBEKNASOCUYZEO-UHFFFAOYSA-N n-(4-chlorophenyl)-1-(4-cyclopropyl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2C3CC3)=C2CC1 YBEKNASOCUYZEO-UHFFFAOYSA-N 0.000 claims 1
- JUENETMURFSLCN-UHFFFAOYSA-N n-(4-chlorophenyl)-1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(Cl)C=C1 JUENETMURFSLCN-UHFFFAOYSA-N 0.000 claims 1
- UEVOFCXPYYCENN-UHFFFAOYSA-N n-(4-chlorophenyl)-1-(4-methylsulfonyl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(S(=O)(=O)C)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(Cl)C=C1 UEVOFCXPYYCENN-UHFFFAOYSA-N 0.000 claims 1
- XKAHONKNAQNURA-UHFFFAOYSA-N n-(4-chlorophenyl)-1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCOCC3)=C2CC1 XKAHONKNAQNURA-UHFFFAOYSA-N 0.000 claims 1
- IVDGZINPJBFSCF-UHFFFAOYSA-N n-(4-chlorophenyl)-1-(5-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC2=CC(OC)=CC=C2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(Cl)C=C1 IVDGZINPJBFSCF-UHFFFAOYSA-N 0.000 claims 1
- QTNSLFWDPHXFNV-UHFFFAOYSA-N n-(4-chlorophenyl)-1-(6-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C12=CC(OC)=CC=C2CCC1N(C1=O)C=CC=C1C(=O)NC1=CC=C(Cl)C=C1 QTNSLFWDPHXFNV-UHFFFAOYSA-N 0.000 claims 1
- GPYKSKBWPPOLEF-LJQANCHMSA-N n-(4-chlorophenyl)-1-[(1r)-2,3-dihydro-1h-inden-1-yl]-2-oxopyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C(C1=O)=CC=CN1[C@H]1C2=CC=CC=C2CC1 GPYKSKBWPPOLEF-LJQANCHMSA-N 0.000 claims 1
- AGDIKYWRWLPPGL-RBUKOAKNSA-N n-(4-chlorophenyl)-1-[(1r,2s)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]-2-oxopyridine-3-carboxamide Chemical compound O=C1N([C@@H]2C3=CC=CC=C3C[C@@H]2O)C=CC=C1C(=O)NC1=CC=C(Cl)C=C1 AGDIKYWRWLPPGL-RBUKOAKNSA-N 0.000 claims 1
- GPYKSKBWPPOLEF-IBGZPJMESA-N n-(4-chlorophenyl)-1-[(1s)-2,3-dihydro-1h-inden-1-yl]-2-oxopyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C(C1=O)=CC=CN1[C@@H]1C2=CC=CC=C2CC1 GPYKSKBWPPOLEF-IBGZPJMESA-N 0.000 claims 1
- AGDIKYWRWLPPGL-MOPGFXCFSA-N n-(4-chlorophenyl)-1-[(1s,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]-2-oxopyridine-3-carboxamide Chemical compound O=C1N([C@H]2C3=CC=CC=C3C[C@H]2O)C=CC=C1C(=O)NC1=CC=C(Cl)C=C1 AGDIKYWRWLPPGL-MOPGFXCFSA-N 0.000 claims 1
- WCFFKNLJNKFSKV-UHFFFAOYSA-N n-(4-chlorophenyl)-1-[4-(4-methylsulfonylpiperazin-1-yl)-2,3-dihydro-1h-inden-1-yl]-2-oxopyridine-3-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CC(Cl)=CC=2)=CC=C1 WCFFKNLJNKFSKV-UHFFFAOYSA-N 0.000 claims 1
- MCVUESRCIUEVBT-UHFFFAOYSA-N n-(4-chlorophenyl)-1-[4-[4-(2-hydroxyethyl)piperazin-1-yl]-2,3-dihydro-1h-inden-1-yl]-2-oxopyridine-3-carboxamide Chemical compound C1CN(CCO)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CC(Cl)=CC=2)=CC=C1 MCVUESRCIUEVBT-UHFFFAOYSA-N 0.000 claims 1
- XLMPERUYAURCDW-UHFFFAOYSA-N n-(4-chlorophenyl)-1-[4-[4-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]piperazin-1-yl]-2,3-dihydro-1h-inden-1-yl]-2-oxopyridine-3-carboxamide Chemical compound C1CN(CCOCCOCCO)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CC(Cl)=CC=2)=CC=C1 XLMPERUYAURCDW-UHFFFAOYSA-N 0.000 claims 1
- KFZGMLHEJPJGPF-UHFFFAOYSA-N n-(4-chlorophenyl)-2-oxo-1-(4-piperazin-1-yl-2,3-dihydro-1h-inden-1-yl)pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCNCC3)=C2CC1 KFZGMLHEJPJGPF-UHFFFAOYSA-N 0.000 claims 1
- VTHSVMKBVHTVQK-UHFFFAOYSA-N n-(4-chlorophenyl)-2-oxo-1-(4-propan-2-yloxy-2,3-dihydro-1h-inden-1-yl)pyridine-3-carboxamide Chemical compound C1CC=2C(OC(C)C)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(Cl)C=C1 VTHSVMKBVHTVQK-UHFFFAOYSA-N 0.000 claims 1
- KDNCSAYNQPIUNG-UHFFFAOYSA-N n-(4-chlorophenyl)-2-oxo-1-[4-(trifluoromethoxy)-2,3-dihydro-1h-inden-1-yl]pyridine-3-carboxamide Chemical compound C1CC=2C(OC(F)(F)F)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(Cl)C=C1 KDNCSAYNQPIUNG-UHFFFAOYSA-N 0.000 claims 1
- QHFVQLSKQGAFLS-UHFFFAOYSA-N n-(4-cyanophenyl)-1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C(=CC=C3)N3CCOCC3)CC2)C(=O)C=1C(=O)NC1=CC=C(C#N)C=C1 QHFVQLSKQGAFLS-UHFFFAOYSA-N 0.000 claims 1
- KCHPRFYSPUDDAB-UHFFFAOYSA-N n-(4-fluorophenyl)-1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(F)C=C1 KCHPRFYSPUDDAB-UHFFFAOYSA-N 0.000 claims 1
- WYHFRIHVHLTYIR-UHFFFAOYSA-N n-(4-fluorophenyl)-1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCOCC3)=C2CC1 WYHFRIHVHLTYIR-UHFFFAOYSA-N 0.000 claims 1
- FCYVRKSBZJTFJV-UHFFFAOYSA-N n-(4-fluorophenyl)-2-oxo-1-(4-piperazin-1-yl-2,3-dihydro-1h-inden-1-yl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCNCC3)=C2CC1 FCYVRKSBZJTFJV-UHFFFAOYSA-N 0.000 claims 1
- IIWSBUKWODLEKS-UHFFFAOYSA-N n-(4-iodophenyl)-1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(I)C=C1 IIWSBUKWODLEKS-UHFFFAOYSA-N 0.000 claims 1
- DGTPBRNONUUWKM-UHFFFAOYSA-N n-(4-iodophenyl)-1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(I)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCOCC3)=C2CC1 DGTPBRNONUUWKM-UHFFFAOYSA-N 0.000 claims 1
- XWBYOAOSNXJUJL-UHFFFAOYSA-N n-(4-methoxyphenyl)-1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCOCC3)=C2CC1 XWBYOAOSNXJUJL-UHFFFAOYSA-N 0.000 claims 1
- ZLZGMQCUAMVEQR-UHFFFAOYSA-N n-[4-(3-ethoxyphenyl)phenyl]-1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound CCOC1=CC=CC(C=2C=CC(NC(=O)C=3C(N(C4C5=C(C(=CC=C5)OC)CC4)C=CC=3)=O)=CC=2)=C1 ZLZGMQCUAMVEQR-UHFFFAOYSA-N 0.000 claims 1
- CAGPATUTEHOHOQ-UHFFFAOYSA-N n-[4-(3-hydroxyphenyl)phenyl]-1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC(C=C1)=CC=C1C1=CC=CC(O)=C1 CAGPATUTEHOHOQ-UHFFFAOYSA-N 0.000 claims 1
- ZLTXJHIHOZGEHA-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]-1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC(C=C1)=CC=C1C1=CC=C(N)C=C1 ZLTXJHIHOZGEHA-UHFFFAOYSA-N 0.000 claims 1
- CGWJEBBGFKMTHD-UHFFFAOYSA-N n-[4-(4-hydroxyphenyl)phenyl]-1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC(C=C1)=CC=C1C1=CC=C(O)C=C1 CGWJEBBGFKMTHD-UHFFFAOYSA-N 0.000 claims 1
- LTLDWOWHFWDHOP-UHFFFAOYSA-N n-[4-(4-methoxyanilino)phenyl]-1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(C=C1)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCOCC3)=C2CC1 LTLDWOWHFWDHOP-UHFFFAOYSA-N 0.000 claims 1
- RJTXLRFGKBANFQ-UHFFFAOYSA-N n-[4-(difluoromethoxy)phenyl]-1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(OC(F)F)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCOCC3)=C2CC1 RJTXLRFGKBANFQ-UHFFFAOYSA-N 0.000 claims 1
- ZRJSSENUSSKGMT-UHFFFAOYSA-N n-[4-(dimethylamino)phenyl]-1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCOCC3)=C2CC1 ZRJSSENUSSKGMT-UHFFFAOYSA-N 0.000 claims 1
- XNZJEIZZDNELFJ-UHFFFAOYSA-N n-cyclohexyl-1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1CCCCC1 XNZJEIZZDNELFJ-UHFFFAOYSA-N 0.000 claims 1
- RWBINACOBDDDGF-UHFFFAOYSA-N n-cyclohexyl-1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C(=CC=C3)N3CCOCC3)CC2)C(=O)C=1C(=O)NC1CCCCC1 RWBINACOBDDDGF-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 150000003557 thiazoles Chemical class 0.000 claims 1
- 150000003577 thiophenes Chemical class 0.000 claims 1
- 0 *C(C(*)=C1C(N(*)*)=O)=C(*)N(C(C2)CC3C2****3)C1=O Chemical compound *C(C(*)=C1C(N(*)*)=O)=C(*)N(C(C2)CC3C2****3)C1=O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17287609P | 2009-04-27 | 2009-04-27 | |
| US61/172,876 | 2009-04-27 | ||
| PCT/US2010/032632 WO2010126914A1 (en) | 2009-04-27 | 2010-04-27 | Pyridinone antagonists of alpha-4 integrins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012525336A JP2012525336A (ja) | 2012-10-22 |
| JP2012525336A5 true JP2012525336A5 (https=) | 2013-06-13 |
Family
ID=42235905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012507475A Pending JP2012525336A (ja) | 2009-04-27 | 2010-04-27 | α−４インテグリンのピリジノンアンタゴニスト |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US8367836B2 (https=) |
| EP (1) | EP2424841A1 (https=) |
| JP (1) | JP2012525336A (https=) |
| CN (1) | CN102459179A (https=) |
| AU (1) | AU2010241742A1 (https=) |
| BR (1) | BRPI1015259A2 (https=) |
| CA (1) | CA2760151A1 (https=) |
| IL (1) | IL215956A0 (https=) |
| MX (1) | MX2011011326A (https=) |
| SG (2) | SG10201401836RA (https=) |
| WO (1) | WO2010126914A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2726588C (en) | 2008-06-03 | 2019-04-16 | Karl Kossen | Compounds and methods for treating inflammatory and fibrotic disorders |
| BR112013002112B1 (pt) * | 2010-07-29 | 2021-04-06 | Rigel Pharmaceuticals, Inc. | Composto, composição farmacêutica, e, uso de um composto, ou de um respectivo sal farmaceuticamente aceitável, ou de uma composição |
| KR101317656B1 (ko) * | 2011-06-30 | 2013-10-15 | 연세대학교 산학협력단 | 복제효소 인산화를 조절하는 신규 ｃ형 간염 예방 또는 치료용 조성물 |
| EP2562174A1 (de) * | 2011-08-24 | 2013-02-27 | Bayer Cropscience AG | Herbizid wirksame 6-Oxo-1,6-dihydropyrimidin-5-carboxamide und 2-Oxo-1,2-dihydropyridin-3-carboxamide |
| RS55728B1 (sr) * | 2012-01-31 | 2017-07-31 | Daiichi Sankyo Co Ltd | Derivat piridona |
| MX2014013489A (es) * | 2012-05-09 | 2015-02-12 | Bayer Cropscience Ag | 5-halogenopirazolindanil carboxamidas. |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| MX382781B (es) | 2014-04-02 | 2025-03-13 | Intermune Inc | Piridinonas anti-fibroticas. |
| TWI690525B (zh) * | 2014-07-07 | 2020-04-11 | 日商第一三共股份有限公司 | 具有四氫吡喃基甲基之吡啶酮衍生物及其用途 |
| US9840513B2 (en) * | 2015-07-16 | 2017-12-12 | Abbvie S.Á.R.L. | Substituted tricyclics and method of use |
| WO2019200114A1 (en) * | 2018-04-12 | 2019-10-17 | Arbutus Biopharma Corporation | Methods for preparing substituted dihydroindene-4-carboxamide compounds |
| AU2019373242B2 (en) | 2018-10-30 | 2023-07-13 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4 beta 7 integrin |
| KR102659859B1 (ko) | 2018-10-30 | 2024-04-25 | 길리애드 사이언시즈, 인코포레이티드 | 알파4β7 인테그린의 억제를 위한 화합물 |
| EP4541422A3 (en) | 2018-10-30 | 2025-06-25 | Gilead Sciences, Inc. | Quinoline derivatives as alpha4beta7 integrin inhibitors |
| CN112969700B (zh) | 2018-10-30 | 2024-08-20 | 吉利德科学公司 | 作为α4β7整合素抑制剂的咪唑并吡啶衍生物 |
| CA3131930A1 (en) * | 2019-02-28 | 2020-09-03 | Kezar Life Sciences | Thiazole derivatives as protein secretion inhibitors |
| JP7636326B2 (ja) * | 2019-07-29 | 2025-02-26 | 武田薬品工業株式会社 | 複素環化合物 |
| KR102908219B1 (ko) | 2019-08-14 | 2026-01-08 | 길리애드 사이언시즈, 인코포레이티드 | 알파 4 베타 7 인테그린의 저해용 화합물 |
| KR20220111673A (ko) * | 2021-02-02 | 2022-08-09 | 주식회사 엘지화학 | 단백질 키나아제 억제제로서의 신규한 화합물 |
| TW202511256A (zh) * | 2023-05-25 | 2025-03-16 | 大陸商北京雙鶴潤創科技有限公司 | 肌成束蛋白抑制劑 |
Family Cites Families (90)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2525656A1 (de) | 1974-06-19 | 1976-01-15 | Sandoz Ag | Verfahren zur herstellung neuer heterocyclischer verbindungen |
| US4096255A (en) * | 1974-11-08 | 1978-06-20 | Mitsubishi Chemical Industries Limited | N2 -naphthalenesulfonyl-L-argininamides, and pharmaceutical salts, compositions and methods |
| US4046876A (en) * | 1974-11-08 | 1977-09-06 | Mitsubishi Chemical Industries Limited | N2 -alkoxynaphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US4018915A (en) * | 1976-01-05 | 1977-04-19 | Mitsubishi Chemical Industries Ltd. | N2 -alkoxynaphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US4104392A (en) * | 1974-11-08 | 1978-08-01 | Mitsubishi Chemical Industries Ltd. | N2 -naphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof, and antithrombotic compositions and methods employing them |
| US4055651A (en) * | 1974-11-08 | 1977-10-25 | Mitsubishi Chemical Industries Ltd. | N2 -alkoxynaphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US4070457A (en) * | 1974-11-08 | 1978-01-24 | Mitsubishi Chemical Industries Ltd. | N2 -naphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US4041156A (en) * | 1974-11-08 | 1977-08-09 | Mitsubishi Chemical Industries Limited | N2 -alkoxynaphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US4073914A (en) * | 1974-11-08 | 1978-02-14 | Mitsubishi Chemical Industries Limited | N2 -naphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US4055636A (en) * | 1974-11-08 | 1977-10-25 | Mitsubishi Chemical Industries Ltd. | N2 -alkoxynaphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| JPS5727454B2 (https=) * | 1975-02-21 | 1982-06-10 | ||
| US4018913A (en) * | 1976-01-14 | 1977-04-19 | Mitsubishi Chemical Industries Ltd. | N2 -alkoxynaphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| CA1102316A (en) | 1975-12-09 | 1981-06-02 | Shosuke Okamoto | N su2 xx-arylsulfonyl-l-argininamides and the pharmaceutically acceptable salts thereof |
| US4036955A (en) * | 1976-07-22 | 1977-07-19 | Mitsubishi Chemical Industries Ltd. | N2 -naphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| DE2742173A1 (de) * | 1977-09-20 | 1979-03-29 | Bayer Ag | Phenoxy-pyridinyl(pyrimidinyl)-alkanole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| US4235871A (en) * | 1978-02-24 | 1980-11-25 | Papahadjopoulos Demetrios P | Method of encapsulating biologically active materials in lipid vesicles |
| IT1211096B (it) * | 1981-08-20 | 1989-09-29 | Lpb Ist Farm | Pirimidine e s.triazinici adattivita' ipolipidemizzante. |
| US4672065A (en) * | 1982-11-19 | 1987-06-09 | Chevron Research Company | N-substituted phenoxyacetamide fungicides |
| US4501728A (en) * | 1983-01-06 | 1985-02-26 | Technology Unlimited, Inc. | Masking of liposomes from RES recognition |
| US4565814A (en) | 1983-01-28 | 1986-01-21 | Sanofi | Pyridazine derivatives having a psychotropic action and compositions |
| JPS59212480A (ja) | 1983-05-17 | 1984-12-01 | Nippon Soda Co Ltd | ピリダジン誘導体及び除草剤 |
| DE3322720A1 (de) * | 1983-06-24 | 1985-01-03 | Chemische Werke Hüls AG, 4370 Marl | Verwendung von in 2-stellung mit (substituierten) aminogruppen substituierten 4-dl-alkylester-(alpha)-alaninyl-6-chlor-s-triazinen als herbizide, insbesondere gegen flughafer |
| US4505910A (en) * | 1983-06-30 | 1985-03-19 | American Home Products Corporation | Amino-pyrimidine derivatives, compositions and use |
| NZ210669A (en) | 1983-12-27 | 1988-05-30 | Syntex Inc | Benzoxazin-4-one derivatives and pharmaceutical compositions |
| PH22520A (en) * | 1984-11-12 | 1988-10-17 | Yamanouchi Pharma Co Ltd | Heterocyclic compounds having 4-lover alkyl-3-hydroxy-2-lower alkyl phenoxy-lower alkylene-y-group, and process of producing them |
| US4959364A (en) * | 1985-02-04 | 1990-09-25 | G. D. Searle & Co. | Method of treating inflammation, allergy, asthma and proliferative skin disease using heterocyclic amides |
| US5023252A (en) * | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US4837028A (en) * | 1986-12-24 | 1989-06-06 | Liposome Technology, Inc. | Liposomes with enhanced circulation time |
| JPH0784424B2 (ja) | 1987-04-15 | 1995-09-13 | 味の素株式会社 | チロシン誘導体及びその用途 |
| EP0330506A3 (en) | 1988-02-26 | 1990-06-20 | Dana Farber Cancer Institute | Vla proteins |
| US5011472A (en) * | 1988-09-06 | 1991-04-30 | Brown University Research Foundation | Implantable delivery system for biological factors |
| DE3904931A1 (de) * | 1989-02-17 | 1990-08-23 | Bayer Ag | Pyridyl-substituierte acrylsaeureester |
| US5030644A (en) * | 1989-07-31 | 1991-07-09 | Merck & Co., Inc. | Imidazole compounds and their use as transglutaminase inhibitors |
| US5260210A (en) | 1989-09-27 | 1993-11-09 | Rubin Lee L | Blood-brain barrier model |
| US4992439A (en) * | 1990-02-13 | 1991-02-12 | Bristol-Myers Squibb Company | Pyridazine carboxylic acids and esters |
| FR2679903B1 (fr) | 1991-08-02 | 1993-12-03 | Elf Sanofi | Derives de la n-sulfonyl indoline portant une fonction amidique, leur preparation, les compositions pharmaceutiques en contenant. |
| NZ239846A (en) * | 1990-09-27 | 1994-11-25 | Merck & Co Inc | Sulphonamide derivatives and pharmaceutical compositions thereof |
| DE4108029A1 (de) * | 1991-03-13 | 1992-09-17 | Bayer Ag | Triazinyl-substituierte acrylsaeureester |
| WO1992016549A1 (de) | 1991-03-18 | 1992-10-01 | Pentapharm Ag | Para-substituierte phenylalanin-derivate |
| IT1247509B (it) * | 1991-04-19 | 1994-12-17 | Univ Cagliari | Composti di sintesi atti all'impiego nella terapia delle infezioni da rhinovirus |
| US5296486A (en) | 1991-09-24 | 1994-03-22 | Boehringer Ingelheim Pharmaceuticals, Inc. | Leukotriene biosynthesis inhibitors |
| AU3420693A (en) | 1991-12-24 | 1993-07-28 | Fred Hutchinson Cancer Research Center | Competitive inhibition of high-avidity alpha4-beta1 receptor using tripeptide ldv |
| JPH07504654A (ja) * | 1992-03-11 | 1995-05-25 | ナルヘックス リミテッド | オキソ及びヒドロキシ置換炭化水素のアミン誘導体 |
| GB9307555D0 (en) * | 1992-04-16 | 1993-06-02 | Zeneca Ltd | Heterocyclic compounds |
| US5518730A (en) | 1992-06-03 | 1996-05-21 | Fuisz Technologies Ltd. | Biodegradable controlled release flash flow melt-spun delivery system |
| DE4227748A1 (de) * | 1992-08-21 | 1994-02-24 | Bayer Ag | Pyridyloxy-acrylsäureester |
| JP2848232B2 (ja) * | 1993-02-19 | 1999-01-20 | 武田薬品工業株式会社 | アルデヒド誘導体 |
| US5770573A (en) * | 1993-12-06 | 1998-06-23 | Cytel Corporation | CS-1 peptidomimetics, compositions and methods of using the same |
| TW530047B (en) * | 1994-06-08 | 2003-05-01 | Pfizer | Corticotropin releasing factor antagonists |
| US5510332A (en) * | 1994-07-07 | 1996-04-23 | Texas Biotechnology Corporation | Process to inhibit binding of the integrin α4 62 1 to VCAM-1 or fibronectin and linear peptides therefor |
| WO1996001644A1 (en) | 1994-07-11 | 1996-01-25 | Athena Neurosciences, Inc. | Inhibitors of leukocyte adhesion |
| US6306840B1 (en) | 1995-01-23 | 2001-10-23 | Biogen, Inc. | Cell adhesion inhibitors |
| IL117659A (en) | 1995-04-13 | 2000-12-06 | Dainippon Pharmaceutical Co | Substituted 2-phenyl pyrimidino amino acetamide derivative process for preparing the same and a pharmaceutical composition containing same |
| PT765879E (pt) * | 1995-09-29 | 2001-05-31 | Sankyo Co | Derivados 13-substituidos de milbemicina-5-oxima sua preparacao e utilizacao contra insectos e outras pragas |
| DE19536891A1 (de) | 1995-10-04 | 1997-04-10 | Basf Ag | Neue Aminosäurederivate, ihre Herstellung und Verwendung |
| DE19548709A1 (de) | 1995-12-23 | 1997-07-03 | Merck Patent Gmbh | Tyrosinderivate |
| EP0910575B1 (en) | 1996-06-21 | 2002-09-25 | Takeda Chemical Industries, Ltd. | Method for producing peptides |
| KR20000022190A (ko) | 1996-06-28 | 2000-04-25 | 플레믹 크리스티안 | 인테그린 저해제로서의 페닐알라닌 유도체 |
| DE19654483A1 (de) | 1996-06-28 | 1998-01-02 | Merck Patent Gmbh | Phenylalanin-Derivate |
| DE19629817A1 (de) * | 1996-07-24 | 1998-01-29 | Hoechst Ag | Neue Imino-Derivate als Inhibitoren der Knochenresorption und Vitronectinrezeptor-Antagonisten |
| DE19647317A1 (de) * | 1996-11-15 | 1998-05-20 | Hoechst Schering Agrevo Gmbh | Substituierte Stickstoff-Heterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| DE19713000A1 (de) | 1997-03-27 | 1998-10-01 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten |
| IL143928A0 (en) * | 1999-01-22 | 2002-04-21 | Elan Pharm Inc | Fused ring heteroaryl and heterocyclic compounds which inhibit leukocyte adhesion mediated by vla-4 |
| PL350050A1 (en) * | 1999-01-22 | 2002-10-21 | Elan Pharm Inc | Acyl derivatives which treat vla-4 related disorders |
| US6436904B1 (en) * | 1999-01-25 | 2002-08-20 | Elan Pharmaceuticals, Inc. | Compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| AU782616B2 (en) * | 1999-05-07 | 2005-08-11 | Encysive Pharmaceuticals Inc. | Carboxylic acid derivatives that inhibit the binding of integrins to their receptors |
| DK1176956T3 (da) * | 1999-05-07 | 2008-05-26 | Encysive Pharmaceuticals Inc | Carboxylsyrederivater, som inhiberer bindingen af integriner til deres receptorer |
| US6544994B2 (en) * | 2000-06-07 | 2003-04-08 | Eprov Ag | Pharmaceutical preparation for treating or preventing cardiovascular or neurological disorders by modulating of the activity of nitric oxide synthase |
| WO2002008206A1 (en) * | 2000-07-21 | 2002-01-31 | Elan Pharmaceuticals, Inc. | 3-amino-2-(4-aminocarbonyloxy)phenyl-propionic acid derivatives as alpha-4- integrin inhibitors |
| US6794506B2 (en) * | 2000-07-21 | 2004-09-21 | Elan Pharmaceuticals, Inc. | 3-(heteroaryl) alanine derivatives-inhibitors of leukocyte adhesion mediated by VLA-4 |
| ES2330719T3 (es) * | 2000-12-28 | 2009-12-15 | SHIONOGI & CO., LTD. | Derivados de 2-piridona con afinidad para el receptor cannabinoide de tipo 2. |
| SI21096B (sl) * | 2001-10-09 | 2012-05-31 | Encysive Pharmaceuticals Inc | Derivati karboksilne kisline ki inhibirajo vezavo integrinov na njihove receptorje |
| TWI281470B (en) * | 2002-05-24 | 2007-05-21 | Elan Pharm Inc | Heterocyclic compounds which inhibit leukocyte adhesion mediated by alpha4 integrins |
| TW200307671A (en) * | 2002-05-24 | 2003-12-16 | Elan Pharm Inc | Heteroaryl compounds which inhibit leukocyte adhesion mediated by α 4 integrins |
| WO2004046122A2 (en) * | 2002-11-16 | 2004-06-03 | Oxford Glycosciences (Uk) Ltd | Benzoxazole, benzthiazole and benzimidazole acid derivatives and their use as heparanase inhibitors |
| SE0302486D0 (sv) * | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | Novel compounds |
| US20050176755A1 (en) * | 2003-10-31 | 2005-08-11 | Dyatkin Alexey B. | Aza-bridged-bicyclic amino acid derivatives as alpha4 integrin antagonists |
| KR20070001976A (ko) * | 2004-02-10 | 2007-01-04 | 얀센 파마슈티카 엔.브이. | 알파４ 인테그린의 길항제로서의 피리다지논 우레아 |
| TWI418346B (zh) * | 2004-07-08 | 2013-12-11 | 伊蘭製藥公司 | 包括聚合物部分之多價ｖｌａ-４拮抗劑 |
| TW200843761A (en) * | 2004-10-28 | 2008-11-16 | Shionogi & Co | 3-carbamoyl-2-pyridone derivatives |
| US20060116713A1 (en) * | 2004-11-26 | 2006-06-01 | Ivan Sepetka | Aneurysm treatment devices and methods |
| JO2787B1 (en) * | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
| WO2007008541A2 (en) * | 2005-07-08 | 2007-01-18 | Kalypsys, Inc. | Cellular cholesterol absorption modifiers |
| CA2624524C (en) * | 2005-09-29 | 2014-07-08 | Elan Pharmaceuticals, Inc. | Carbamate compounds which inhibit leukocyte adhesion mediated by vla-4 |
| ATE493405T1 (de) * | 2005-09-29 | 2011-01-15 | Elan Pharm Inc | Pyrimidinylamidverbindungen, die die durch vla-4 vermittelte leukozytenadhäsion inhibieren |
| JP2009526761A (ja) * | 2006-01-30 | 2009-07-23 | アレイ バイオファーマ、インコーポレイテッド | ヘテロ二環式チオフェン化合物および使用の方法 |
| WO2007101165A1 (en) * | 2006-02-27 | 2007-09-07 | Elan Pharmaceuticals, Inc. | Pyrimidinyl sulfonamide compounds which inhibit leukocyte adhesion mediated by vla-4 |
| US8778977B2 (en) * | 2006-06-30 | 2014-07-15 | Sunesis Pharmaceuticals, Inc. | Pyridinonyl PDK1 inhibitors |
| WO2008084671A1 (ja) * | 2006-12-27 | 2008-07-17 | Shionogi & Co., Ltd. | １－置換－２－ピリドン－３－カルボン酸誘導体の製造方法 |
| WO2009032277A1 (en) * | 2007-09-06 | 2009-03-12 | Schering Corporation | Gamma secretase modulators |
-
2010
- 2010-04-27 AU AU2010241742A patent/AU2010241742A1/en not_active Abandoned
- 2010-04-27 SG SG10201401836RA patent/SG10201401836RA/en unknown
- 2010-04-27 SG SG2011078409A patent/SG175355A1/en unknown
- 2010-04-27 CA CA2760151A patent/CA2760151A1/en not_active Abandoned
- 2010-04-27 WO PCT/US2010/032632 patent/WO2010126914A1/en not_active Ceased
- 2010-04-27 JP JP2012507475A patent/JP2012525336A/ja active Pending
- 2010-04-27 CN CN2010800273757A patent/CN102459179A/zh active Pending
- 2010-04-27 EP EP10719684A patent/EP2424841A1/en not_active Withdrawn
- 2010-04-27 MX MX2011011326A patent/MX2011011326A/es active IP Right Grant
- 2010-04-27 US US12/768,680 patent/US8367836B2/en not_active Expired - Fee Related
- 2010-04-27 BR BRPI1015259A patent/BRPI1015259A2/pt not_active IP Right Cessation
-
2011
- 2011-10-26 IL IL215956A patent/IL215956A0/en unknown
-
2012
- 2012-12-28 US US13/730,522 patent/US20130252957A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012525336A5 (https=) | ||
| JP6440321B2 (ja) | スルホンアミド誘導体またはその薬学的に許容される酸付加塩 | |
| TWI567067B (zh) | ＴｒＫ抑制化合物 | |
| US8003642B2 (en) | Nitrogenated heterocyclic derivative, and pharmaceutical agent comprising the derivative as active ingredient | |
| JP2018522823A5 (https=) | ||
| JP2015517981A5 (https=) | ||
| CA2529686C (en) | 2-acylaminothiazole derivative or salt thereof | |
| JP5059275B2 (ja) | 新規３置換尿素誘導体およびその医薬としての用途 | |
| ES2533954T3 (es) | Derivados de resorcinol como inhibidores de HSP90 | |
| RU2013143028A (ru) | Тиазолилфенилбензолсульфонамидопроизводные в качестве ингибиторов киназ | |
| RU2013130925A (ru) | Оксимовые соединения в качестве средств для повышения уровня холестерина высокой плотности | |
| JP2007519754A5 (https=) | ||
| RU2010101633A (ru) | Новое сульфонамидное производное малоновой кислоты и его фармацевтическое применение | |
| RU2005108999A (ru) | Азотсодержащие ароматические производные | |
| JP2010526096A5 (ja) | キナーゼ阻害剤として有用なチアゾールおよびピラゾール | |
| TW200815422A (en) | Heteroaryl derivatives as cytokine inhibitors | |
| RU2017145650A (ru) | Ингибиторы тирозинкиназы брутона | |
| JP2014511869A5 (https=) | ||
| NZ553696A (en) | Nitrogenous heterocyclic derivative and medicine containing the same as an active ingredient | |
| TWI226240B (en) | Piperazine compound | |
| TW200914440A (en) | Vinyl-aryl derivatives for inflammation and immune-related uses | |
| TWI317359B (en) | N-phenyl-arylsulfonamide compound and the pharmaceuticals containing the same as active ingredient | |
| RU2018131766A (ru) | 6-гетероциклил-4-морфолин-4-илпиридин-2-оны, пригодные для лечения рака и диабета | |
| JP2016534124A5 (https=) | ||
| JP5055268B2 (ja) | ヒストンデアセチラーゼの新規な阻害剤としての置換されたアミノプロペニルピペリジンまたはモルホリン誘導体 |