ES2633987T3 - Derivados de pirido-carboxamidas tricíclicas como inhibidores de ROCK - Google Patents
Derivados de pirido-carboxamidas tricíclicas como inhibidores de ROCK Download PDFInfo
- Publication number
- ES2633987T3 ES2633987T3 ES14741757.0T ES14741757T ES2633987T3 ES 2633987 T3 ES2633987 T3 ES 2633987T3 ES 14741757 T ES14741757 T ES 14741757T ES 2633987 T3 ES2633987 T3 ES 2633987T3
- Authority
- ES
- Spain
- Prior art keywords
- carboxamide
- chromene
- pyridin
- substituted
- 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.)
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- 239000003112 inhibitor Substances 0.000 title 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 title 1
- 239000011435 rock Substances 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 56
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 23
- 101150105130 RORB gene Proteins 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 20
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- -1 (5-phenylisoxazol-3-yl) methyl Chemical group 0.000 claims description 78
- JBOYQZDFEWOILV-UHFFFAOYSA-N 5h-chromene Chemical compound O1C=CC=C2CC=CC=C21 JBOYQZDFEWOILV-UHFFFAOYSA-N 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
- 101000669921 Homo sapiens Rho-associated protein kinase 2 Proteins 0.000 claims description 2
- 102100039314 Rho-associated protein kinase 2 Human genes 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- FPBXOMZZNSZCOX-GFCCVEGCSA-N 1-(difluoromethyl)-N-[(1R)-1-(3-methoxyphenyl)ethyl]-[1]benzofuro[2,3-c]pyridine-7-carboxamide Chemical compound FC(C1=NC=CC2=C1OC1=C2C=CC(=C1)C(=O)N[C@H](C)C1=CC(=CC=C1)OC)F FPBXOMZZNSZCOX-GFCCVEGCSA-N 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- WNHMPCBFTMFRLC-UHFFFAOYSA-N COc1cccc(CNC(=O)c2ccc3c4ccncc4n(C)c(=O)c3c2)c1 Chemical compound COc1cccc(CNC(=O)c2ccc3c4ccncc4n(C)c(=O)c3c2)c1 WNHMPCBFTMFRLC-UHFFFAOYSA-N 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- VPIGHPBOTWERIL-GFCCVEGCSA-N 1-fluoro-N-[(1R)-1-(3-methoxyphenyl)ethyl]-9H-pyrido[3,4-b]indole-7-carboxamide Chemical compound FC1=NC=CC2=C1NC1=CC(=CC=C21)C(=O)N[C@H](C)C1=CC(=CC=C1)OC VPIGHPBOTWERIL-GFCCVEGCSA-N 0.000 claims 1
- RLGISLYKJUGUSQ-UHFFFAOYSA-N 1-fluoro-N-[(3-fluorophenyl)methyl]-9H-pyrido[3,4-b]indole-7-carboxamide Chemical compound FC1=NC=CC2=C1NC1=CC(=CC=C21)C(=O)NCC1=CC(=CC=C1)F RLGISLYKJUGUSQ-UHFFFAOYSA-N 0.000 claims 1
- FEIVZACOGJUUIJ-UHFFFAOYSA-N 1-fluoro-N-[(3-methoxyphenyl)methyl]-9H-pyrido[3,4-b]indole-7-carboxamide Chemical compound FC1=NC=CC2=C1NC1=CC(=CC=C21)C(=O)NCC1=CC(=CC=C1)OC FEIVZACOGJUUIJ-UHFFFAOYSA-N 0.000 claims 1
- MNUNGKPVACPKMW-GFCCVEGCSA-N 3-fluoro-N-[(1R)-1-(3-methoxyphenyl)ethyl]-9H-pyrido[3,4-b]indole-7-carboxamide Chemical compound FC1=CC2=C(NC3=CC(=CC=C23)C(=O)N[C@H](C)C2=CC(=CC=C2)OC)C=N1 MNUNGKPVACPKMW-GFCCVEGCSA-N 0.000 claims 1
- NNPMQSMSQMMCEP-UHFFFAOYSA-N 3-fluoro-N-[(3-fluorophenyl)methyl]-9H-pyrido[3,4-b]indole-7-carboxamide Chemical compound FC1=CC2=C(NC3=CC(=CC=C23)C(=O)NCC2=CC(=CC=C2)F)C=N1 NNPMQSMSQMMCEP-UHFFFAOYSA-N 0.000 claims 1
- VYIBCOSBNVFEIW-UHFFFAOYSA-N 3-phenylpropanamide Chemical compound NC(=O)CCC1=CC=CC=C1 VYIBCOSBNVFEIW-UHFFFAOYSA-N 0.000 claims 1
- HSDLAOURKYHLIT-GFCCVEGCSA-N 4-fluoro-N-[(1R)-1-(3-methoxyphenyl)ethyl]-9H-pyrido[3,4-b]indole-7-carboxamide Chemical compound FC1=CN=CC=2NC3=CC(=CC=C3C=21)C(=O)N[C@H](C)C1=CC(=CC=C1)OC HSDLAOURKYHLIT-GFCCVEGCSA-N 0.000 claims 1
- XMWAXVJTWIHADJ-UHFFFAOYSA-N 4-fluoro-N-[(3-fluorophenyl)methyl]-9H-pyrido[3,4-b]indole-7-carboxamide Chemical compound FC1=CN=CC=2NC3=CC(=CC=C3C=21)C(=O)NCC1=CC(=CC=C1)F XMWAXVJTWIHADJ-UHFFFAOYSA-N 0.000 claims 1
- IKKBUPGYTNFXPN-UHFFFAOYSA-N 4-fluoro-N-[(3-methoxyphenyl)methyl]-9H-pyrido[3,4-b]indole-7-carboxamide Chemical compound FC1=CN=CC=2NC3=CC(=CC=C3C=21)C(=O)NCC1=CC(=CC=C1)OC IKKBUPGYTNFXPN-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- OFQWIOILYATHSB-OAHLLOKOSA-N 5-ethyl-6-oxo-N-[(1R)-1-phenylethyl]benzo[c][1,7]naphthyridine-8-carboxamide Chemical compound C(C)N1C(C2=C(C3=CC=NC=C13)C=CC(=C2)C(=O)N[C@H](C)C1=CC=CC=C1)=O OFQWIOILYATHSB-OAHLLOKOSA-N 0.000 claims 1
- DJDDFFKEKDUPHF-OAHLLOKOSA-N 5-ethyl-N-[(1R)-1-(3-methoxyphenyl)ethyl]-6-oxobenzo[c][1,7]naphthyridine-8-carboxamide Chemical compound C(C)N1C(C2=C(C3=CC=NC=C13)C=CC(=C2)C(=O)N[C@H](C)C1=CC(=CC=C1)OC)=O DJDDFFKEKDUPHF-OAHLLOKOSA-N 0.000 claims 1
- FIYQDRKJJNDGOA-UHFFFAOYSA-N 5-ethyl-N-[(3-methoxyphenyl)methyl]-6-oxobenzo[c][1,7]naphthyridine-8-carboxamide Chemical compound C(C)N1C(C2=C(C3=CC=NC=C13)C=CC(=C2)C(=O)NCC1=CC(=CC=C1)OC)=O FIYQDRKJJNDGOA-UHFFFAOYSA-N 0.000 claims 1
- LQNSBMPWSVIMGD-MRXNPFEDSA-N 6-(2-methoxyethyl)-5-oxo-N-[(1R)-1-phenylethyl]benzo[c][2,7]naphthyridine-8-carboxamide Chemical compound COCCN1C(C2=CN=CC=C2C2=C1C=C(C=C2)C(=O)N[C@H](C)C1=CC=CC=C1)=O LQNSBMPWSVIMGD-MRXNPFEDSA-N 0.000 claims 1
- GTTGLYXERASJGT-MRXNPFEDSA-N 6-(2-methoxyethyl)-N-[(1R)-1-(3-methoxyphenyl)ethyl]-5-oxobenzo[c][2,7]naphthyridine-8-carboxamide Chemical compound COCCN1C(C2=CN=CC=C2C2=C1C=C(C=C2)C(=O)N[C@H](C)C1=CC(=CC=C1)OC)=O GTTGLYXERASJGT-MRXNPFEDSA-N 0.000 claims 1
- RMGUEWGQPAJGLO-CYBMUJFWSA-N 6-oxo-N-[(1R)-1-phenylethyl]-5H-benzo[c][1,7]naphthyridine-8-carboxamide Chemical compound O=C1NC2=CN=CC=C2C2=C1C=C(C=C2)C(=O)N[C@H](C)C1=CC=CC=C1 RMGUEWGQPAJGLO-CYBMUJFWSA-N 0.000 claims 1
- LJYFVHQERVRDRZ-UHFFFAOYSA-N 9-ethyl-N-(2-hydroxy-1-phenylethyl)pyrido[3,4-b]indole-7-carboxamide Chemical compound C(C)N1C2=C(C3=CC=C(C=C13)C(=O)NC(CO)C1=CC=CC=C1)C=CN=C2 LJYFVHQERVRDRZ-UHFFFAOYSA-N 0.000 claims 1
- KHDTWGHINMBUJH-OAHLLOKOSA-N 9-ethyl-N-[(1R)-1-(3-methoxyphenyl)ethyl]pyrido[3,4-b]indole-7-carboxamide Chemical compound C(C)N1C2=C(C3=CC=C(C=C13)C(=O)N[C@H](C)C1=CC(=CC=C1)OC)C=CN=C2 KHDTWGHINMBUJH-OAHLLOKOSA-N 0.000 claims 1
- PSPBSHYBJYTJCC-UHFFFAOYSA-N 9-ethyl-N-[(2-fluorophenyl)methyl]pyrido[3,4-b]indole-7-carboxamide Chemical compound C(C)N1C2=C(C3=CC=C(C=C13)C(=O)NCC1=C(C=CC=C1)F)C=CN=C2 PSPBSHYBJYTJCC-UHFFFAOYSA-N 0.000 claims 1
- JHLOSJVJHPLCQJ-UHFFFAOYSA-N 9-ethyl-N-[(3-methoxyphenyl)methyl]pyrido[3,4-b]indole-7-carboxamide Chemical compound C(C)N1C2=C(C3=CC=C(C=C13)C(=O)NCC1=CC(=CC=C1)OC)C=CN=C2 JHLOSJVJHPLCQJ-UHFFFAOYSA-N 0.000 claims 1
- DEHSXMGTTWQYHV-CQSZACIVSA-N 9-methyl-N-[(1R)-1-phenylethyl]pyrido[3,4-b]indole-7-carboxamide Chemical compound CN1C2=C(C3=CC=C(C=C13)C(=O)N[C@H](C)C1=CC=CC=C1)C=CN=C2 DEHSXMGTTWQYHV-CQSZACIVSA-N 0.000 claims 1
- KSMHODYMLODQNZ-UHFFFAOYSA-N 9-methyl-N-[[3-(trifluoromethoxy)phenyl]methyl]pyrido[3,4-b]indole-7-carboxamide Chemical compound CN1C2=C(C3=CC=C(C=C13)C(=O)NCC1=CC(=CC=C1)OC(F)(F)F)C=CN=C2 KSMHODYMLODQNZ-UHFFFAOYSA-N 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 206010003225 Arteriospasm coronary Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- ZUPXTGFATWSXGC-CYBMUJFWSA-N C1(=CC=CC=C1)[C@@H](C)NC(=O)C1=CC=C2C3=C(NC2=C1)C=NC=C3 Chemical compound C1(=CC=CC=C1)[C@@H](C)NC(=O)C1=CC=C2C3=C(NC2=C1)C=NC=C3 ZUPXTGFATWSXGC-CYBMUJFWSA-N 0.000 claims 1
- FPPPDEGTHKDSLM-UHFFFAOYSA-N COC=1C=C(CNC(=O)C2=CC=C3C4=C(NC3=C2)C(=NC=C4)C)C=CC1 Chemical compound COC=1C=C(CNC(=O)C2=CC=C3C4=C(NC3=C2)C(=NC=C4)C)C=CC1 FPPPDEGTHKDSLM-UHFFFAOYSA-N 0.000 claims 1
- XKIGTHQQQJJAJT-CYBMUJFWSA-N COc1cccc(c1)[C@@H](C)NC(=O)c1ccc2c(c1)[nH]c1c(C)nccc21 Chemical compound COc1cccc(c1)[C@@H](C)NC(=O)c1ccc2c(c1)[nH]c1c(C)nccc21 XKIGTHQQQJJAJT-CYBMUJFWSA-N 0.000 claims 1
- CUCWGQZKQLQPTA-CQSZACIVSA-N COc1cccc(c1)[C@@H](C)NC(=O)c1ccc2c(c1)[nH]c1cnc(C)cc21 Chemical compound COc1cccc(c1)[C@@H](C)NC(=O)c1ccc2c(c1)[nH]c1cnc(C)cc21 CUCWGQZKQLQPTA-CQSZACIVSA-N 0.000 claims 1
- OPVSJIZFISHPHE-OAHLLOKOSA-N C[C@@H](NC(=O)c1ccc2c(c1)n(CC#N)c1cnccc21)c1ccccc1 Chemical compound C[C@@H](NC(=O)c1ccc2c(c1)n(CC#N)c1cnccc21)c1ccccc1 OPVSJIZFISHPHE-OAHLLOKOSA-N 0.000 claims 1
- PVXGUMORIMJFSS-GOSISDBHSA-N C[C@@H](NC(=O)c1ccc2c(c1)n(CCN1CCCC1)c(=O)c1cnccc21)c1ccc(F)cc1 Chemical compound C[C@@H](NC(=O)c1ccc2c(c1)n(CCN1CCCC1)c(=O)c1cnccc21)c1ccc(F)cc1 PVXGUMORIMJFSS-GOSISDBHSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims 1
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 1
- QKQXIEVXAPHKLX-UHFFFAOYSA-N ClC1=C(CNC(=O)C2=CC=C3C4=C(NC3=C2)C(=NC=C4)C)C=CC=C1 Chemical compound ClC1=C(CNC(=O)C2=CC=C3C4=C(NC3=C2)C(=NC=C4)C)C=CC=C1 QKQXIEVXAPHKLX-UHFFFAOYSA-N 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 208000003890 Coronary Vasospasm Diseases 0.000 claims 1
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 1
- VVPBUFWVNIAUKT-UHFFFAOYSA-N FC1=C(CNC(=O)C2=CC=C3C4=C(NC3=C2)C(=NC=C4)C)C=C(C=C1)OC Chemical compound FC1=C(CNC(=O)C2=CC=C3C4=C(NC3=C2)C(=NC=C4)C)C=C(C=C1)OC VVPBUFWVNIAUKT-UHFFFAOYSA-N 0.000 claims 1
- BMEMOHHPYXVQJC-CQSZACIVSA-N FC1=CC=C(C=C1)[C@@H](C)NC(=O)C=1C=CC2=C(N(C(C3=CN=CC=C23)=O)CCO)C=1 Chemical compound FC1=CC=C(C=C1)[C@@H](C)NC(=O)C=1C=CC2=C(N(C(C3=CN=CC=C23)=O)CCO)C=1 BMEMOHHPYXVQJC-CQSZACIVSA-N 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- JVKHVHALWMOQBH-UHFFFAOYSA-N N-(2-hydroxy-1-phenylethyl)-9H-pyrido[3,4-b]indole-7-carboxamide Chemical compound OCC(C1=CC=CC=C1)NC(=O)C1=CC=C2C3=C(NC2=C1)C=NC=C3 JVKHVHALWMOQBH-UHFFFAOYSA-N 0.000 claims 1
- RHMGKHDUBRRMSS-UHFFFAOYSA-N N-(2-hydroxy-1-phenylethyl)-[1]benzofuro[2,3-c]pyridine-7-carboxamide Chemical compound C1=NC=CC2=C1OC1=C2C=CC(=C1)C(=O)NC(CO)C1=CC=CC=C1 RHMGKHDUBRRMSS-UHFFFAOYSA-N 0.000 claims 1
- LKMNKIPZENZTEM-CYBMUJFWSA-N N-[(1R)-1-(3-methoxyphenyl)ethyl]-6-oxo-5H-benzo[c][1,7]naphthyridine-8-carboxamide Chemical compound COC=1C=C(C=CC=1)[C@@H](C)NC(=O)C=1C=CC2=C(C(NC3=CN=CC=C23)=O)C=1 LKMNKIPZENZTEM-CYBMUJFWSA-N 0.000 claims 1
- UYWYQQVLMBMSSZ-CQSZACIVSA-N N-[(1R)-1-(3-methoxyphenyl)ethyl]-9-methylpyrido[3,4-b]indole-7-carboxamide Chemical compound COC=1C=C(C=CC=1)[C@@H](C)NC(=O)C1=CC=C2C3=C(N(C2=C1)C)C=NC=C3 UYWYQQVLMBMSSZ-CQSZACIVSA-N 0.000 claims 1
- LCXPFCGRIBLRQH-CYBMUJFWSA-N N-[(1R)-1-(3-methoxyphenyl)ethyl]-9H-pyrido[3,4-b]indole-7-carboxamide Chemical compound COC=1C=C(C=CC=1)[C@@H](C)NC(=O)C1=CC=C2C3=C(NC2=C1)C=NC=C3 LCXPFCGRIBLRQH-CYBMUJFWSA-N 0.000 claims 1
- QXAFXQGFQUHTBG-GFCCVEGCSA-N N-[(1R)-1-(4-fluorophenyl)ethyl]-5-oxo-6H-benzo[c][2,7]naphthyridine-8-carboxamide Chemical compound FC1=CC=C(C=C1)[C@@H](C)NC(=O)C=1C=CC2=C(NC(C3=CN=CC=C23)=O)C=1 QXAFXQGFQUHTBG-GFCCVEGCSA-N 0.000 claims 1
- JTLNDLQAESIMRK-CQSZACIVSA-N N-[(1R)-1-phenylethyl]-9-(2,2,2-trifluoroethyl)pyrido[3,4-b]indole-7-carboxamide Chemical compound C1(=CC=CC=C1)[C@@H](C)NC(=O)C1=CC=C2C3=C(N(C2=C1)CC(F)(F)F)C=NC=C3 JTLNDLQAESIMRK-CQSZACIVSA-N 0.000 claims 1
- QNJJZWIGOIKFRY-CYBMUJFWSA-N N-[(1R)-1-phenylethyl]-[1]benzofuro[2,3-c]pyridine-7-carboxamide Chemical compound C1=NC=CC2=C1OC1=C2C=CC(=C1)C(=O)N[C@H](C)C1=CC=CC=C1 QNJJZWIGOIKFRY-CYBMUJFWSA-N 0.000 claims 1
- KJFCGGMTRBKRMH-UHFFFAOYSA-N N-[(2,6-difluorophenyl)methyl]-1-fluoro-9H-pyrido[3,4-b]indole-7-carboxamide Chemical compound FC1=C(CNC(=O)C2=CC=C3C4=C(NC3=C2)C(=NC=C4)F)C(=CC=C1)F KJFCGGMTRBKRMH-UHFFFAOYSA-N 0.000 claims 1
- JLSVVFMGBNWRIK-UHFFFAOYSA-N N-[(2,6-difluorophenyl)methyl]-4-fluoro-9H-pyrido[3,4-b]indole-7-carboxamide Chemical compound FC1=C(CNC(=O)C2=CC=C3C4=C(NC3=C2)C=NC=C4F)C(=CC=C1)F JLSVVFMGBNWRIK-UHFFFAOYSA-N 0.000 claims 1
- UDUCDCJFGOIPOU-UHFFFAOYSA-N N-[(2-chlorophenyl)methyl]-1-fluoro-9H-pyrido[3,4-b]indole-7-carboxamide Chemical compound ClC1=C(CNC(=O)C2=CC=C3C4=C(NC3=C2)C(=NC=C4)F)C=CC=C1 UDUCDCJFGOIPOU-UHFFFAOYSA-N 0.000 claims 1
- XYVOWWDUJUXOBT-UHFFFAOYSA-N N-[(2-chlorophenyl)methyl]-5-methyl-6-oxobenzo[c][1,7]naphthyridine-8-carboxamide Chemical compound ClC1=C(C=CC=C1)CNC(=O)C=1C=CC2=C(C(N(C3=CN=CC=C23)C)=O)C=1 XYVOWWDUJUXOBT-UHFFFAOYSA-N 0.000 claims 1
- ZPXFEZKPKQJGEH-UHFFFAOYSA-N N-[(2-chlorophenyl)methyl]-6-oxo-5H-benzo[c][1,7]naphthyridine-8-carboxamide Chemical compound ClC1=C(C=CC=C1)CNC(=O)C=1C=CC2=C(C(NC3=CN=CC=C23)=O)C=1 ZPXFEZKPKQJGEH-UHFFFAOYSA-N 0.000 claims 1
- PBOJPNFHHZYQAP-UHFFFAOYSA-N N-[(2-chlorophenyl)methyl]-9-(2,2,2-trifluoroethyl)pyrido[3,4-b]indole-7-carboxamide Chemical compound ClC1=C(CNC(=O)C2=CC=C3C4=C(N(C3=C2)CC(F)(F)F)C=NC=C4)C=CC=C1 PBOJPNFHHZYQAP-UHFFFAOYSA-N 0.000 claims 1
- AHKAQEGHWJZFSR-UHFFFAOYSA-N N-[(2-chlorophenyl)methyl]-9-(cyclopropylmethyl)pyrido[3,4-b]indole-7-carboxamide Chemical compound ClC1=C(CNC(=O)C2=CC=C3C4=C(N(C3=C2)CC2CC2)C=NC=C4)C=CC=C1 AHKAQEGHWJZFSR-UHFFFAOYSA-N 0.000 claims 1
- QENFYLVCIRIVKM-UHFFFAOYSA-N N-[(2-chlorophenyl)methyl]-9-methylpyrido[3,4-b]indole-7-carboxamide Chemical compound ClC1=C(CNC(=O)C2=CC=C3C4=C(N(C3=C2)C)C=NC=C4)C=CC=C1 QENFYLVCIRIVKM-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D498/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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| US201361842098P | 2013-07-02 | 2013-07-02 | |
| US201361842098P | 2013-07-02 | ||
| PCT/US2014/044988 WO2015002915A1 (en) | 2013-07-02 | 2014-07-01 | Tricyclic pyri do-carboxam i d e derivatives as rock inhibitors |
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| ES2633987T3 true ES2633987T3 (es) | 2017-09-26 |
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| TW (1) | TW201506024A (https=) |
| WO (1) | WO2015002915A1 (https=) |
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| US9708337B2 (en) | 2013-02-22 | 2017-07-18 | Bristol-Myers Squibb Company | Aryl amide-based kinase inhibitors |
| WO2014134391A1 (en) | 2013-02-28 | 2014-09-04 | Bristol-Myers Squibb Company | Phenylpyrazole derivatives as potent rock1 and rock2 inhibitors |
| AR094929A1 (es) | 2013-02-28 | 2015-09-09 | Bristol Myers Squibb Co | Derivados de fenilpirazol como inhibidores potentes de rock1 y rock2 |
| US9914740B2 (en) | 2013-07-02 | 2018-03-13 | Bristol-Myers Squibb Company | Tricyclic pyrido-carboxamide derivatives as rock inhibitors |
| EP3016950B1 (en) | 2013-07-02 | 2017-06-07 | Bristol-Myers Squibb Company | Tricyclic pyrido-carboxamide derivatives as rock inhibitors |
| WO2015054358A1 (en) | 2013-10-11 | 2015-04-16 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| US9902702B2 (en) | 2014-07-15 | 2018-02-27 | Bristol-Myers Squibb Company | Spirocycloheptanes as inhibitors of rock |
| US10123993B2 (en) | 2015-01-09 | 2018-11-13 | Bristol-Myers Squibb Company | Cyclic ureas as inhibitors of rock |
| ES2730112T3 (es) | 2015-03-09 | 2019-11-08 | Bristol Myers Squibb Co | Lactamas como inhibidores de ROCK |
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| WO2015002915A1 (en) | 2015-01-08 |
| TW201506024A (zh) | 2015-02-16 |
| CN105492444B (zh) | 2018-09-07 |
| CN105492444A (zh) | 2016-04-13 |
| US20160152628A1 (en) | 2016-06-02 |
| JP6434968B2 (ja) | 2018-12-05 |
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