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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- ZAPFZTXQSCYRLE-UHFFFAOYSA-N n-[[3-(methanesulfonamido)phenyl]methyl]-[1]benzofuro[2,3-c]pyridine-7-carboxamide Chemical compound CS(=O)(=O)NC1=CC=CC(CNC(=O)C=2C=C3C(C4=CC=NC=C4O3)=CC=2)=C1 ZAPFZTXQSCYRLE-UHFFFAOYSA-N 0.000 claims 1
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 260
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Classifications
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- C07D491/00—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
- 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
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—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
- 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
- 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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- C—CHEMISTRY; METALLURGY
- 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
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- 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 |
Publications (1)
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| ES2633987T3 true ES2633987T3 (es) | 2017-09-26 |
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| ES14741757.0T Active ES2633987T3 (es) | 2013-07-02 | 2014-07-01 | Derivados de pirido-carboxamidas tricíclicas como inhibidores de ROCK |
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| US (1) | US9914740B2 (enExample) |
| EP (1) | EP3016951B1 (enExample) |
| JP (1) | JP6434968B2 (enExample) |
| CN (1) | CN105492444B (enExample) |
| AR (1) | AR096788A1 (enExample) |
| ES (1) | ES2633987T3 (enExample) |
| TW (1) | TW201506024A (enExample) |
| WO (1) | WO2015002915A1 (enExample) |
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| JP2016509066A (ja) | 2013-02-22 | 2016-03-24 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | アダプター関連キナーゼ１（ａａｋ１）の阻害剤としての５ｈ−クロメノ［３，４−ｃ］ピリジン |
| CN105102448B (zh) | 2013-02-28 | 2018-03-06 | 百时美施贵宝公司 | 作为rock1和rock2抑制剂的苯基吡唑衍生物 |
| AR094929A1 (es) | 2013-02-28 | 2015-09-09 | Bristol Myers Squibb Co | Derivados de fenilpirazol como inhibidores potentes de rock1 y rock2 |
| AR096788A1 (es) | 2013-07-02 | 2016-02-03 | Bristol Myers Squibb Co | Compuestos tricíclicos de carboxamida como inhibidores potentes de rock |
| WO2015002926A1 (en) | 2013-07-02 | 2015-01-08 | Bristol-Myers Squibb Company | Tricyclic pyrido-carboxamide derivatives as rock inhibitors |
| ES2678877T3 (es) | 2013-10-11 | 2018-08-20 | Bristol-Myers Squibb Company | Inhibidores de pirrolotriazina quinasa |
| US9902702B2 (en) | 2014-07-15 | 2018-02-27 | Bristol-Myers Squibb Company | Spirocycloheptanes as inhibitors of rock |
| TW201630899A (zh) | 2015-01-09 | 2016-09-01 | 必治妥美雅史谷比公司 | 作為ｒｏｃｋ抑制劑的環狀脲類 |
| TW201706265A (zh) | 2015-03-09 | 2017-02-16 | 必治妥美雅史谷比公司 | 做為Ｒｈｏ激酶（ＲＯＣＫ）抑制劑之內醯胺 |
| EP3292124B1 (en) | 2015-04-10 | 2019-05-22 | Bristol-Myers Squibb Company | 6h-isochromeno[3,4-c]pyridines and benzo[c][1,7]naphthyridin-6-(5h)-ones as adaptor associated kinase 1 (aak1) inhibitors |
| KR20180011843A (ko) | 2015-06-11 | 2018-02-02 | 바실리어 파마슈티카 인터내셔널 리미티드 | 유출-펌프 억제제 및 이의 치료적 용도 |
| DK3341376T3 (da) * | 2015-08-26 | 2021-03-29 | Fundacion Del Sector Publico Estatal Centro Nac De Investigaciones Oncologicas Carlos Iii F S P Cnio | Kondenserede tricykliske forbindelser som proteinkinase-inhibitorer |
| TWI730032B (zh) | 2016-01-13 | 2021-06-11 | 美商必治妥美雅史谷比公司 | 作為ｒｏｃｋ抑制劑之螺庚烷水楊酸醯胺及相關化合物 |
| EP3426674A4 (en) | 2016-03-09 | 2019-08-14 | Blade Therapeutics, Inc. | CYCLIC KETO AMID COMPOUNDS AS CALPAIN MODULATORS AND METHOD FOR THE PRODUCTION AND USE THEREOF |
| KR102457933B1 (ko) | 2016-05-27 | 2022-10-24 | 브리스톨-마이어스 스큅 컴퍼니 | Rock의 억제제로서의 트리아졸론 및 테트라졸론 |
| US11292801B2 (en) | 2016-07-05 | 2022-04-05 | Blade Therapeutics, Inc. | Calpain modulators and therapeutic uses thereof |
| WO2018009622A1 (en) | 2016-07-07 | 2018-01-11 | Bristol-Myers Squibb Company | Lactam, cyclic urea and carbamate, and triazolone derivatives as potent and selective rock inhibitors |
| KR102491994B1 (ko) | 2016-07-07 | 2023-01-25 | 브리스톨-마이어스 스큅 컴퍼니 | Rock의 억제제로서의 스피로락탐 |
| US10787450B2 (en) | 2016-07-07 | 2020-09-29 | Bristol-Myers Squibb Company | Spiro-fused cyclic ureas as inhibitors of rock |
| AU2017336523B2 (en) | 2016-09-28 | 2022-07-21 | Blade Therapeutics, Inc. | Calpain modulators and therapeutic uses thereof |
| KR102511441B1 (ko) * | 2016-11-30 | 2023-03-16 | 브리스톨-마이어스 스큅 컴퍼니 | 트리시클릭 Rho 키나제 억제제 |
| EP3640242B1 (en) * | 2017-06-16 | 2023-04-19 | Hitgen Ltd. | Rock-inhibiting compound and uses thereof |
| US12060341B2 (en) | 2017-07-12 | 2024-08-13 | Bristol-Myers Squibb Company | Spiroheptanyl hydantoins as ROCK inhibitors |
| TW201908293A (zh) | 2017-07-12 | 2019-03-01 | 美商必治妥美雅史谷比公司 | 作為rock抑制劑之5員及雙環雜環醯胺 |
| US11299488B2 (en) | 2017-07-12 | 2022-04-12 | Bristol-Myers Squibb Company | Five membered-aminoheterocycle and 5,6-or 6,6-membered bicyclic aminoheterocyclic inhibitors of rock for the treatment of heart failure |
| KR102644889B1 (ko) | 2017-07-12 | 2024-03-06 | 브리스톨-마이어스 스큅 컴퍼니 | Rock 억제제로서의 스피로헵타닐 히단토인 |
| US11306081B2 (en) | 2017-07-12 | 2022-04-19 | Bristol-Myers Squibb Company | Phenylacetamides as inhibitors of rock |
| US11192891B2 (en) | 2017-11-03 | 2021-12-07 | Bristol-Myers Squibb Company | Diazaspiro ROCK inhibitors |
| JP2021523092A (ja) * | 2018-03-21 | 2021-09-02 | ピラマル・ファーマ・リミテッドＰｉｒａｍａｌ Ｐｈａｒｍａ Ｌｉｍｉｔｅｄ | アルファ−（ジアリールメチル）アルキルアミンの改良された不斉合成 |
| CN108299429B (zh) * | 2018-04-09 | 2021-10-08 | 中南大学 | 一类八氢苯并萘啶化合物及其制备方法和应用 |
| CN110283119A (zh) * | 2018-04-20 | 2019-09-27 | 长沙理工大学 | 一种合成全碳基取代吡啶衍生物的方法 |
| CN110759923B (zh) * | 2018-07-26 | 2022-08-30 | 上海医药工业研究院有限公司 | 嘧啶并吡咯并哒嗪衍生物、其中间体、制备方法、药物组合物和用途 |
| CA3169676A1 (en) * | 2020-02-28 | 2021-09-02 | Dominic Reynolds | Compounds and methods for modulating splicing |
| CN115697968B (zh) * | 2020-05-28 | 2024-03-29 | 杭州中美华东制药有限公司 | (s)-2-氨基-3-(4-(2,3-二甲基吡啶-4-基)苯基丙酸甲酯及其盐的制备方法 |
| CN112010853A (zh) * | 2020-09-01 | 2020-12-01 | 成都大学 | 一种食品中杂环胺风险物质norharman及类似物的合成方法 |
| EP4395889A1 (en) * | 2021-08-30 | 2024-07-10 | Remix Therapeutics Inc. | Compounds and methods for modulating splicing |
| CA3238227A1 (en) | 2021-11-11 | 2023-05-19 | The Doshisha | Cryopreservation preparation for corneal endothelial cells and method for producing said cryopreservation preparation |
| CN114544851B (zh) * | 2022-02-22 | 2023-12-15 | 苏州正济医药研究有限公司 | 一种测定邻氯苯甘氨酸甲酯酒石酸盐及杂质的分析方法 |
| CN117105779A (zh) * | 2023-07-18 | 2023-11-24 | 河南师范大学 | 一种5-溴-2-甲酰基苯甲酸甲酯的制备方法 |
| CN119874716B (zh) * | 2025-03-27 | 2025-07-15 | 上海隆盛化工有限公司 | 1-氯-6,8-二氟-7-异丙基苯并呋喃并[2,3-c]吡啶及其合成方法和应用 |
Family Cites Families (102)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU168036B (enExample) | 1973-11-09 | 1976-02-28 | ||
| HU168776B (enExample) | 1973-11-09 | 1976-07-28 | ||
| CA1098910A (en) | 1978-06-15 | 1981-04-07 | Robert N. Schut | 3-amino-2-(5-fluoro and 5-methoxy-1h-indol-3-yl) propanoic acid derivatives |
| JPS57116067A (en) | 1981-01-12 | 1982-07-19 | Sankyo Kagaku Kk | Novel 8-quinolinesulfonyl derivative, its synthesis and use |
| DE3703435A1 (de) | 1987-02-05 | 1988-08-18 | Thomae Gmbh Dr K | Neue thiazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| IE68593B1 (en) | 1989-12-06 | 1996-06-26 | Sanofi Sa | Heterocyclic substituted acylaminothiazoles their preparation and pharmaceutical compositions containing them |
| US5945380A (en) | 1995-05-26 | 1999-08-31 | Bayer Aktiengesellschaft | Pyridyl-thiazoles and their use to protect plants against infections by micro-organisms |
| US6187797B1 (en) | 1996-12-23 | 2001-02-13 | Dupont Pharmaceuticals Company | Phenyl-isoxazoles as factor XA Inhibitors |
| DE69720773T2 (de) | 1996-12-23 | 2004-01-29 | Bristol Myers Squibb Pharma Co | SAUERSTOFF ODER SCHWEFEL ENTHALTENDE 5-GLIEDRIGE HETEROAROMATISHE DERIVATIVE ALS FACTOR Xa HEMMER |
| DE69821132T2 (de) | 1997-10-27 | 2004-10-21 | Takeda Chemical Industries Ltd | 1,3-thiazole als adenosine a3 rezeptor antagonisten zur behandlung von asthma, allergien und diabetes |
| AU3702699A (en) | 1998-04-08 | 1999-11-01 | Bayer Aktiengesellschaft | Substituted oxazolyle and thiazolyl uracil herbicides |
| US7026334B1 (en) | 1999-07-26 | 2006-04-11 | Shionogi & Co., Ltd. | Thiazolidine compounds and pharmaceutical compositions exhibiting thrombopoietin receptor agonism |
| JP5000828B2 (ja) * | 2000-03-15 | 2012-08-15 | サノフィ−アベンティス・ドイチュラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | ＩｋＢキナーゼ阻害活性を有する置換ベーターカルボリン |
| WO2001068648A1 (en) * | 2000-03-15 | 2001-09-20 | Aventis Pharma Deutschland Gmbh | Substituted beta-carbolines with ikb-kinase inhibiting activity |
| GB0010183D0 (en) | 2000-04-26 | 2000-06-14 | Ferring Bv | Inhibitors of dipeptidyl peptidase IV |
| ATE542805T1 (de) | 2000-08-11 | 2012-02-15 | Nippon Chemiphar Co | Ppar-delta aktivatoren |
| JP2002053566A (ja) | 2000-08-11 | 2002-02-19 | Japan Tobacco Inc | チアゾール化合物及びその医薬用途 |
| US20020173507A1 (en) | 2000-08-15 | 2002-11-21 | Vincent Santora | Urea compounds and methods of uses |
| US20020103192A1 (en) | 2000-10-26 | 2002-08-01 | Curtin Michael L. | Inhibitors of histone deacetylase |
| CA2436739A1 (en) | 2000-12-26 | 2002-07-04 | Takeda Chemical Industries, Ltd. | Combination agent |
| US20040077697A1 (en) | 2001-02-02 | 2004-04-22 | Hiroyuki Koshio | 2-Acylaminothiazole derivative or its salt |
| MY130778A (en) | 2001-02-09 | 2007-07-31 | Vertex Pharma | Heterocyclic inhibitiors of erk2 and uses thereof |
| US20020177594A1 (en) | 2001-03-14 | 2002-11-28 | Curtin Michael L. | Inhibitors of histone deacetylase |
| JP4157381B2 (ja) | 2001-03-23 | 2008-10-01 | 日本ケミファ株式会社 | ペルオキシソーム増殖剤応答性受容体の活性化剤 |
| CA2445697A1 (en) | 2001-04-26 | 2002-11-07 | Daiichi Pharmaceutical Co., Ltd. | Drug efflux pump inhibitor |
| US20050080113A1 (en) | 2001-06-11 | 2005-04-14 | Shigenori Ohkawa | Medicinal compositions |
| GB0123589D0 (en) | 2001-10-01 | 2001-11-21 | Syngenta Participations Ag | Organic compounds |
| US7163952B2 (en) | 2001-12-03 | 2007-01-16 | Japan Tobacco Inc. | Azole compound and medicinal use thereof |
| CN1319967C (zh) | 2002-01-18 | 2007-06-06 | 安斯泰来制药有限公司 | 2－酰基氨基噻唑衍生物或其盐 |
| EP1467981A1 (en) | 2002-01-25 | 2004-10-20 | Kylix Pharmaceuticals B.V. | 4(hetero-) aryl substituted (thia-/oxa-/pyra) zoles for inhibition of tie-2 |
| CA2484233A1 (en) | 2002-05-13 | 2003-11-27 | Eli Lilly And Company | Multicyclic compounds for use as melanin concentrating hormone antagonists in the treatment of obesity and diabetes |
| JP2006508042A (ja) | 2002-07-18 | 2006-03-09 | ブリストル−マイヤーズ スクイブ カンパニー | グルココルチコイド受容体の修飾物質および方法 |
| TW200812986A (en) | 2002-08-09 | 2008-03-16 | Nps Pharma Inc | New compounds |
| WO2004016592A1 (en) | 2002-08-14 | 2004-02-26 | Ppd Discovery, Inc. | Prenylation inhibitors and methods of their synthesis and use |
| CA2504320A1 (en) | 2002-10-30 | 2004-05-21 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of rock and other protein kinases |
| GB0230087D0 (en) | 2002-12-24 | 2003-01-29 | Astrazeneca Ab | Therapeutic agents |
| GB0302672D0 (en) | 2003-02-06 | 2003-03-12 | Astrazeneca Ab | Pharmaceutical formulations |
| WO2004071509A1 (ja) | 2003-02-12 | 2004-08-26 | Nippon Chemiphar Co., Ltd. | オリゴデンドロサイト分化促進剤 |
| PT1611088E (pt) | 2003-04-07 | 2009-09-24 | Pharmacyclics Inc | Hidroxamatos como agentes terapêuticos |
| AU2004232958A1 (en) | 2003-04-16 | 2004-11-04 | F.-Hoffmann La-Roche Inc. | 4 - (3,4 - disubstituted phenyl) - pyrrolidin-2-one compounds as phosphodiesterase 4 inhibitors |
| CN100545161C (zh) | 2003-08-15 | 2009-09-30 | 中国科学院上海药物研究所 | 一类杂环衍生物、制备方法及其用途 |
| US7351727B2 (en) | 2003-09-02 | 2008-04-01 | Bristol-Myers Squibb Company | Inhibitors of 15-lipoxygenase |
| RU2006111093A (ru) | 2003-09-06 | 2007-10-27 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Модуляторы атр-связывающих кассетных транспортеров |
| SA04250288B1 (ar) | 2003-09-19 | 2008-07-19 | سولفاي فارماسوتيكالز بي . في | مشتقات ثيازول thiazole كمعدلات لمستقبل المكونات الكيميائية للقنب cannabinoid |
| WO2005044194A2 (en) | 2003-10-28 | 2005-05-19 | Pharmacia Corporation | TREATMENT OR PREVENTION OF NEOPLASIA BY USE OF AN Hsp90 INHIBITOR |
| BRPI0415896A (pt) | 2003-10-28 | 2007-01-09 | Pharmacia Corp | combinações compreendendo um inibidor de hsp90 e um inibidor de fosfodiesterase para tratamento ou prevenção de neoplasia |
| JP2007519754A (ja) | 2004-01-30 | 2007-07-19 | スミスクライン ビーチャム コーポレーション | 化合物 |
| WO2005075435A1 (en) | 2004-01-30 | 2005-08-18 | Vertex Pharmaceuticals Incorporated | Modulators of atp-binding cassette transporters |
| WO2005077373A2 (en) | 2004-02-03 | 2005-08-25 | Astrazeneca Ab | Treatment of gastro-esophageal reflux disease (gerd) |
| WO2005077345A1 (en) | 2004-02-03 | 2005-08-25 | Astrazeneca Ab | Compounds for the treatment of gastro-esophageal reflux disease |
| MY148488A (en) | 2004-02-18 | 2013-04-30 | Astrazeneca Ab | Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| AU2005212073B2 (en) | 2004-02-18 | 2010-07-08 | Kyorin Pharmaceutical Co., Ltd. | Bicyclic amide derivatives |
| US7259155B2 (en) | 2004-05-05 | 2007-08-21 | Otsuka Pharmaceutical Factory, Inc. | Phosphonic diester derivatives |
| JP3928086B2 (ja) | 2005-03-29 | 2007-06-13 | 塩野義製薬株式会社 | ３−プロペニルセフェム誘導体 |
| FR2885129B1 (fr) | 2005-04-29 | 2007-06-15 | Proskelia Sas | Nouveaux derives de l'ureee substituee parun thiazole ou benzothiazole, leur procede de preparation, leur application a titre de medicaments, les compositions pharmaceutiques les renfermant et utilisation. |
| KR20080019213A (ko) | 2005-05-09 | 2008-03-03 | 아칠리온 파르마세우티칼스 인코포레이티드 | 티아졸 화합물 및 그 사용방법 |
| US7655446B2 (en) | 2005-06-28 | 2010-02-02 | Vertex Pharmaceuticals Incorporated | Crystal structure of Rho-kinase I kinase domain complexes and binding pockets thereof |
| JP2009505948A (ja) * | 2005-07-11 | 2009-02-12 | デブジェン エヌブイ | キナーゼ阻害剤としてのアミド誘導体 |
| EP1962892A4 (en) | 2005-11-22 | 2011-10-12 | Univ South Florida | INHIBITION OF CELL PROLIFERATION |
| WO2007075896A2 (en) | 2005-12-22 | 2007-07-05 | Kemia, Inc. | Heterocyclic cytokine inhibitors |
| US8455658B2 (en) | 2006-01-25 | 2013-06-04 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
| WO2007116106A1 (es) | 2006-04-12 | 2007-10-18 | Palobiofarma, S.L. | Nuevos compuestos como antagonistas de los receptores a1 de adenosina |
| WO2007133622A2 (en) | 2006-05-12 | 2007-11-22 | Vertex Pharmaceuticals Incorporated | Selective inhibitors of rock protein kinase and uses thereof |
| US7935715B2 (en) | 2006-07-28 | 2011-05-03 | Boehringer Ingelheim International Gmbh | Compounds which modulate the CB2 receptor |
| EA200900403A1 (ru) | 2006-09-25 | 2009-10-30 | Бёрингер Ингельхайм Интернациональ Гмбх | Соединения, которые модулируют рецептор св2 |
| TW200831081A (en) | 2006-12-25 | 2008-08-01 | Kyorin Seiyaku Kk | Glucokinase activator |
| WO2008124000A2 (en) | 2007-04-02 | 2008-10-16 | Ligand Pharmaceuticals Incorporated | Thiazole derivatives as androgen receptor modulator compounds |
| GB0706793D0 (en) | 2007-04-05 | 2007-05-16 | Evotec Ag | Compounds |
| EP2170309B1 (en) | 2007-06-22 | 2016-10-26 | Hydra Biosciences, Inc. | 2,6-dioxo,-2,3-dihydro-1h-purine compounds useful for treating disorders related to the activity of the trpa1 channel |
| EP2193119B1 (en) | 2007-08-27 | 2014-01-01 | Abbvie Deutschland GmbH & Co. KG | 4-(4-pyridinyl)-benzamides and their use as rock activity modulators |
| WO2009026701A1 (en) | 2007-08-29 | 2009-03-05 | Methylgene Inc. | Sirtuin inhibitors |
| ES2331220B1 (es) | 2007-10-02 | 2010-09-23 | Palobiofarma, S.L. | Nuevos compuestos como antagonistas de los receptores a1 de adenosina. |
| CA2699631A1 (en) | 2007-10-31 | 2009-05-07 | Nissan Chemical Industries, Ltd. | Pyridazinone compounds and p2x7 receptor inhibitors |
| WO2009061652A1 (en) | 2007-11-07 | 2009-05-14 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| WO2009067607A2 (en) | 2007-11-20 | 2009-05-28 | Memory Pharmaceuticals Corporation | Combinations of pde4 inhibitors and antipsychotics for the treatment of psychotic disorders |
| WO2009081222A1 (en) | 2007-12-21 | 2009-07-02 | Glenmark Pharmaceuticals, S.A. | Substituted tricyclic pyridine or pyrimidine vanilloid receptor ligands |
| CA2709784A1 (en) | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| US8563552B2 (en) | 2008-02-08 | 2013-10-22 | Shiseido Company Ltd. | Whitening agent and skin external preparation |
| WO2009114552A1 (en) | 2008-03-10 | 2009-09-17 | The Board Of Trustees Of The Leland Stanford Junior University | Heteroaryl compounds, compositions, and methods of use in cancer treatment |
| US20120108614A1 (en) | 2008-05-14 | 2012-05-03 | Chong Jayhong A | Compounds and compositions for treating chemical warfare agent-induced injuries |
| WO2010028193A1 (en) | 2008-09-03 | 2010-03-11 | Repligen Corporation | Compounds including pimelic acid derivatives as hdac inhibitors |
| US20100063085A1 (en) * | 2008-09-11 | 2010-03-11 | University Court Of The University Of Dundee | Method of treating learning impairment in down's syndrome subjects |
| WO2010029300A1 (en) | 2008-09-12 | 2010-03-18 | Biolipox Ab | Bis aromatic compounds for use in the treatment of inflammation |
| US20120046305A1 (en) | 2008-09-24 | 2012-02-23 | Moran Magdalene M | Methods and compositions for treating respiratory disorders |
| JP5557849B2 (ja) * | 2008-12-19 | 2014-07-23 | ブリストル−マイヤーズ スクイブ カンパニー | カルバゾールおよびカルボリンキナーゼ阻害剤 |
| NZ593135A (en) | 2008-12-19 | 2013-04-26 | Novartis Ag | Isoxazoline derivatives and their use as pesticide |
| MX2011006332A (es) | 2008-12-23 | 2011-06-27 | Abbott Lab | Compuestos antivirales. |
| JP2012051804A (ja) * | 2008-12-26 | 2012-03-15 | Kyoto Univ | Ｅｇ５阻害剤 |
| UA103918C2 (en) | 2009-03-02 | 2013-12-10 | Айерем Элелси | N-(hetero)aryl, 2-(hetero)aryl-substituted acetamides for use as wnt signaling modulators |
| US8362249B2 (en) | 2009-04-27 | 2013-01-29 | Boehringer Ingelheim International Gmbh | CXCR3 receptor antagonists |
| KR20120026611A (ko) | 2009-06-09 | 2012-03-19 | 아브락시스 바이오사이언스, 엘엘씨 | 헷지호그 신호전달의 피리딜-트리아진 억제제 |
| SG178873A1 (en) | 2009-08-25 | 2012-04-27 | Abraxis Bioscience Llc | Combination therapy with nanoparticle compositions of taxane and hedgehog inhibitors |
| JP5856064B2 (ja) * | 2009-11-17 | 2016-02-09 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | 治療特性を有する１，４−ベンゾジアゼピン−２，５−ジオンおよび関連化合物 |
| CN102762203A (zh) | 2009-12-18 | 2012-10-31 | 艾克提弗赛特制药股份有限公司 | 血浆激肽释放酶抑制剂的前药 |
| JP5766690B2 (ja) | 2010-04-12 | 2015-08-19 | 塩野義製薬株式会社 | インテグラーゼ阻害活性を有するピリドン誘導体 |
| WO2011130740A2 (en) | 2010-04-16 | 2011-10-20 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Pyridylthiazole-based ureas as inhibitors of rho associated protein kinase (rock) and methods of use |
| WO2011159857A1 (en) * | 2010-06-16 | 2011-12-22 | Bristol-Myers Squibb Company | Carboline carboxamide compounds useful as kinase inhibitors |
| WO2012054367A1 (en) * | 2010-10-19 | 2012-04-26 | Boehringer Ingelheim International Gmbh | Rho kinase inhibitors |
| HUE036040T2 (hu) * | 2012-03-09 | 2018-06-28 | Lexicon Pharmaceuticals Inc | Adaptor-asszociált kináz 1 gátlása fájdalom kezelésére |
| US8703953B2 (en) | 2012-03-09 | 2014-04-22 | Bristol-Myers Squibb Company | Aryl ether-base kinase inhibitors |
| AR096788A1 (es) | 2013-07-02 | 2016-02-03 | Bristol Myers Squibb Co | Compuestos tricíclicos de carboxamida como inhibidores potentes de rock |
| WO2015002926A1 (en) | 2013-07-02 | 2015-01-08 | Bristol-Myers Squibb Company | Tricyclic pyrido-carboxamide derivatives as rock inhibitors |
-
2014
- 2014-07-01 AR ARP140102466A patent/AR096788A1/es unknown
- 2014-07-01 CN CN201480047827.6A patent/CN105492444B/zh not_active Expired - Fee Related
- 2014-07-01 JP JP2016524303A patent/JP6434968B2/ja not_active Expired - Fee Related
- 2014-07-01 US US14/900,238 patent/US9914740B2/en active Active
- 2014-07-01 ES ES14741757.0T patent/ES2633987T3/es active Active
- 2014-07-01 WO PCT/US2014/044988 patent/WO2015002915A1/en not_active Ceased
- 2014-07-01 EP EP14741757.0A patent/EP3016951B1/en not_active Not-in-force
- 2014-07-01 TW TW103122739A patent/TW201506024A/zh unknown
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| Publication number | Publication date |
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| TW201506024A (zh) | 2015-02-16 |
| JP2016523922A (ja) | 2016-08-12 |
| CN105492444B (zh) | 2018-09-07 |
| US20160152628A1 (en) | 2016-06-02 |
| CN105492444A (zh) | 2016-04-13 |
| AR096788A1 (es) | 2016-02-03 |
| US9914740B2 (en) | 2018-03-13 |
| JP6434968B2 (ja) | 2018-12-05 |
| EP3016951A1 (en) | 2016-05-11 |
| EP3016951B1 (en) | 2017-05-31 |
| WO2015002915A1 (en) | 2015-01-08 |
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