JP2010504342A5 - - Google Patents
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- Publication number
- JP2010504342A5 JP2010504342A5 JP2009529306A JP2009529306A JP2010504342A5 JP 2010504342 A5 JP2010504342 A5 JP 2010504342A5 JP 2009529306 A JP2009529306 A JP 2009529306A JP 2009529306 A JP2009529306 A JP 2009529306A JP 2010504342 A5 JP2010504342 A5 JP 2010504342A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- dihydro
- isoquinolin
- chloro
- alkyl
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 140
- 125000003118 aryl group Chemical group 0.000 claims 60
- 125000001072 heteroaryl group Chemical group 0.000 claims 32
- 229910052739 hydrogen Inorganic materials 0.000 claims 26
- 125000000623 heterocyclic group Chemical group 0.000 claims 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 12
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 10
- -1 tetrahydropyran-4-ylmethyl Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 9
- 125000003277 amino group Chemical group 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- JEVASONHRDRRRF-UHFFFAOYSA-N 2-chloro-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-4-nitrobenzamide Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1C(=O)NC(C(=C1)Cl)=CC2=C1C(=O)NC=C2 JEVASONHRDRRRF-UHFFFAOYSA-N 0.000 claims 4
- WHXKGHDWNQPZNP-UHFFFAOYSA-N 4-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)cyclohexane-1-carboxamide Chemical compound C1CC(N)CCC1C(=O)NC(C(=C1)Cl)=CC2=C1C(=O)NC=C2 WHXKGHDWNQPZNP-UHFFFAOYSA-N 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 4
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000005110 aryl thio group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- WMXFMQUBMUSJBJ-UHFFFAOYSA-N n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-1-methylpiperidine-4-carboxamide Chemical compound C1CN(C)CCC1C(=O)NC(C(=C1)Cl)=CC2=C1C(=O)NC=C2 WMXFMQUBMUSJBJ-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims 4
- VARKGNSLBZWGKS-MDOMKXGZSA-N (1R,3S)-3-amino-N-(7-chloro-1-oxo-2H-isoquinolin-6-yl)cyclopentane-1-carboxamide [4-[(7-chloro-1-oxo-2H-isoquinolin-6-yl)carbamoyl]cyclohexyl] acetate Chemical compound ClC1=C(C=C2C=CNC(C2=C1)=O)NC(=O)[C@H]1C[C@H](CC1)N.ClC1=C(C=C2C=CNC(C2=C1)=O)NC(=O)C1CCC(CC1)OC(C)=O VARKGNSLBZWGKS-MDOMKXGZSA-N 0.000 claims 2
- JQLLYNHFEVAHHJ-MNOVXSKESA-N (1r,3s)-3-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)cyclohexane-1-carboxamide Chemical compound C1[C@@H](N)CCC[C@H]1C(=O)NC(C(=C1)Cl)=CC2=C1C(=O)NC=C2 JQLLYNHFEVAHHJ-MNOVXSKESA-N 0.000 claims 2
- PQDMNMYSDXMLIL-NEPJUHHUSA-N (1r,3s)-3-amino-n-(7-methoxy-1-oxo-2h-isoquinolin-6-yl)cyclohexane-1-carboxamide Chemical compound COC1=CC(C(NC=C2)=O)=C2C=C1NC(=O)[C@@H]1CCC[C@H](N)C1 PQDMNMYSDXMLIL-NEPJUHHUSA-N 0.000 claims 2
- INIUJLPVWFLHOO-CABZTGNLSA-N (1s,2s)-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-2-methyl-4-oxocyclohexane-1-carboxamide Chemical compound C[C@H]1CC(=O)CC[C@@H]1C(=O)NC(C(=C1)Cl)=CC2=C1C(=O)NC=C2 INIUJLPVWFLHOO-CABZTGNLSA-N 0.000 claims 2
- JQLLYNHFEVAHHJ-QWRGUYRKSA-N (1s,3s)-3-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)cyclohexane-1-carboxamide Chemical compound C1[C@@H](N)CCC[C@@H]1C(=O)NC(C(=C1)Cl)=CC2=C1C(=O)NC=C2 JQLLYNHFEVAHHJ-QWRGUYRKSA-N 0.000 claims 2
- QWFCVBMSMZUVFU-NGQZWQHPSA-N (1s,5r)-3-azoniabicyclo[3.1.0]hexane-6-carboxylate Chemical compound C1NC[C@H]2C(C(=O)O)[C@H]21 QWFCVBMSMZUVFU-NGQZWQHPSA-N 0.000 claims 2
- FJWKKOVBOJSOMJ-QGZVFWFLSA-N (2r)-2-(4-chlorophenyl)-2-hydroxy-n-(4-oxo-1h-quinazolin-7-yl)propanamide Chemical compound C1([C@@](O)(C(=O)NC=2C=C3C(C(NC=N3)=O)=CC=2)C)=CC=C(Cl)C=C1 FJWKKOVBOJSOMJ-QGZVFWFLSA-N 0.000 claims 2
- ZHVIWNFGNBYNDX-OAHLLOKOSA-N (2r)-2-amino-2-cyclohexyl-n-(1-oxo-2h-isoquinolin-6-yl)acetamide Chemical compound C1([C@@H](N)C(=O)NC=2C=C3C(C(NC=C3)=O)=CC=2)CCCCC1 ZHVIWNFGNBYNDX-OAHLLOKOSA-N 0.000 claims 2
- MARASEZVJVDXJQ-MRXNPFEDSA-N (2r)-2-amino-2-cyclohexyl-n-(7-methoxy-1-oxo-2h-isoquinolin-6-yl)acetamide Chemical compound C1([C@@H](N)C(=O)NC2=CC3=C(C(NC=C3)=O)C=C2OC)CCCCC1 MARASEZVJVDXJQ-MRXNPFEDSA-N 0.000 claims 2
- KTCLKJWKHZTJLE-LLVKDONJSA-N (2r)-2-amino-3-methyl-n-(4-oxo-1h-quinazolin-7-yl)butanamide Chemical compound N1=CNC(=O)C=2C1=CC(NC(=O)[C@H](N)C(C)C)=CC=2 KTCLKJWKHZTJLE-LLVKDONJSA-N 0.000 claims 2
- NJZMIVUSGDNAHG-OAHLLOKOSA-N (2r)-2-amino-n-(1-oxo-2h-isoquinolin-6-yl)-2-phenylacetamide Chemical compound C1([C@H](C(=O)NC=2C=C3C(C(NC=C3)=O)=CC=2)N)=CC=CC=C1 NJZMIVUSGDNAHG-OAHLLOKOSA-N 0.000 claims 2
- OGWZKLROEMTEBA-CQSZACIVSA-N (2r)-2-amino-n-(4-oxo-1h-quinazolin-7-yl)-2-phenylacetamide Chemical compound C1([C@H](C(=O)NC=2C=C3C(C(NC=N3)=O)=CC=2)N)=CC=CC=C1 OGWZKLROEMTEBA-CQSZACIVSA-N 0.000 claims 2
- XAFGHLJJPKUZKI-CQSZACIVSA-N (2r)-2-amino-n-(4-oxo-1h-quinazolin-7-yl)-3-phenylpropanamide Chemical compound C([C@@H](N)C(=O)NC=1C=C2C(C(NC=N2)=O)=CC=1)C1=CC=CC=C1 XAFGHLJJPKUZKI-CQSZACIVSA-N 0.000 claims 2
- XQWKVQZDJHYNTI-MRXNPFEDSA-N (2r)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-2-(4-methylphenyl)acetamide Chemical compound C1=CC(C)=CC=C1[C@@H](N)C(=O)NC(C(=C1)Cl)=CC2=C1C(=O)NC=C2 XQWKVQZDJHYNTI-MRXNPFEDSA-N 0.000 claims 2
- LZKXNZXRQFFQAH-OAHLLOKOSA-N (2r)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-2-phenylacetamide Chemical compound C1([C@H](C(=O)NC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)N)=CC=CC=C1 LZKXNZXRQFFQAH-OAHLLOKOSA-N 0.000 claims 2
- FFOBQEHTKMMYOK-OAHLLOKOSA-N (2r)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-3-(4-chlorophenyl)propanamide Chemical compound C([C@@H](N)C(=O)NC=1C(=CC=2C(=O)NC=CC=2C=1)Cl)C1=CC=C(Cl)C=C1 FFOBQEHTKMMYOK-OAHLLOKOSA-N 0.000 claims 2
- BHVXQQAOHUXHJX-OAHLLOKOSA-N (2r)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-3-cyclohexylpropanamide Chemical compound C([C@@H](N)C(=O)NC=1C(=CC=2C(=O)NC=CC=2C=1)Cl)C1CCCCC1 BHVXQQAOHUXHJX-OAHLLOKOSA-N 0.000 claims 2
- WXRZSOWZRRRJSB-GFCCVEGCSA-N (2r)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-3-methylbutanamide Chemical compound C1=CNC(=O)C2=C1C=C(NC(=O)[C@H](N)C(C)C)C(Cl)=C2 WXRZSOWZRRRJSB-GFCCVEGCSA-N 0.000 claims 2
- BRUWZKPRMONCGZ-LJQANCHMSA-N (2r)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-3-naphthalen-1-ylpropanamide Chemical compound C1=CNC(=O)C(C=C2Cl)=C1C=C2NC(=O)[C@H](N)CC1=CC=CC2=CC=CC=C12 BRUWZKPRMONCGZ-LJQANCHMSA-N 0.000 claims 2
- FIYBSFIXYPPGOK-LJQANCHMSA-N (2r)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-3-naphthalen-2-ylpropanamide Chemical compound C1=CNC(=O)C(C=C2Cl)=C1C=C2NC(=O)[C@H](N)CC1=CC=C(C=CC=C2)C2=C1 FIYBSFIXYPPGOK-LJQANCHMSA-N 0.000 claims 2
- MPPLZNXMOACWRV-OAHLLOKOSA-N (2r)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-3-phenylpropanamide Chemical compound C([C@@H](N)C(=O)NC=1C(=CC=2C(=O)NC=CC=2C=1)Cl)C1=CC=CC=C1 MPPLZNXMOACWRV-OAHLLOKOSA-N 0.000 claims 2
- CPEUVOVIKQEOHO-CQSZACIVSA-N (2r)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-3-pyridin-4-ylpropanamide Chemical compound C([C@@H](N)C(=O)NC=1C(=CC=2C(=O)NC=CC=2C=1)Cl)C1=CC=NC=C1 CPEUVOVIKQEOHO-CQSZACIVSA-N 0.000 claims 2
- DEUSPAYNLHIUSL-GFCCVEGCSA-N (2r)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-4,4-dimethylpentanamide Chemical compound C1=CNC(=O)C2=C1C=C(NC(=O)[C@H](N)CC(C)(C)C)C(Cl)=C2 DEUSPAYNLHIUSL-GFCCVEGCSA-N 0.000 claims 2
- RADQDLRYXIUSGX-GFCCVEGCSA-N (2r)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-4-methylpentanamide Chemical compound C1=CNC(=O)C2=C1C=C(NC(=O)[C@H](N)CC(C)C)C(Cl)=C2 RADQDLRYXIUSGX-GFCCVEGCSA-N 0.000 claims 2
- OZTWJDXASSVZPZ-QGZVFWFLSA-N (2r)-2-methoxy-n-(7-methoxy-1-oxo-2h-isoquinolin-6-yl)-2-phenylacetamide Chemical compound C1([C@H](C(=O)NC=2C(=CC=3C(=O)NC=CC=3C=2)OC)OC)=CC=CC=C1 OZTWJDXASSVZPZ-QGZVFWFLSA-N 0.000 claims 2
- GJDXVSJQDCVVJF-SNVBAGLBSA-N (2r)-n-(4-oxo-1h-quinazolin-7-yl)pyrrolidine-2-carboxamide Chemical compound C=1C=C(C(NC=N2)=O)C2=CC=1NC(=O)[C@H]1CCCN1 GJDXVSJQDCVVJF-SNVBAGLBSA-N 0.000 claims 2
- DQXBCWGHRZOBIA-QGZVFWFLSA-N (2r)-n-(6-chloro-4-oxo-1h-quinazolin-7-yl)-2-(4-chlorophenyl)-2-hydroxypropanamide Chemical compound C1([C@@](O)(C(=O)NC=2C(=CC=3C(=O)NC=NC=3C=2)Cl)C)=CC=C(Cl)C=C1 DQXBCWGHRZOBIA-QGZVFWFLSA-N 0.000 claims 2
- PMVOMXDSKUVNOM-OAHLLOKOSA-N (2r)-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-2-(2-chlorophenyl)-2-hydroxyacetamide Chemical compound C1([C@H](C(=O)NC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)O)=CC=CC=C1Cl PMVOMXDSKUVNOM-OAHLLOKOSA-N 0.000 claims 2
- QPXDNPWJKQEBFD-OAHLLOKOSA-N (2r)-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-2-(3-chlorophenyl)-2-hydroxyacetamide Chemical compound C1([C@H](C(=O)NC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)O)=CC=CC(Cl)=C1 QPXDNPWJKQEBFD-OAHLLOKOSA-N 0.000 claims 2
- IFLCAMSZRCEJTF-GOSISDBHSA-N (2r)-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-2-(4-chlorophenyl)-2-hydroxypropanamide Chemical compound C1([C@@](O)(C(=O)NC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)C)=CC=C(Cl)C=C1 IFLCAMSZRCEJTF-GOSISDBHSA-N 0.000 claims 2
- BXYBHROBEQFUAY-OAHLLOKOSA-N (2r)-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-2-cyclohexyl-2-hydroxyacetamide Chemical compound C1([C@@H](O)C(=O)NC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)CCCCC1 BXYBHROBEQFUAY-OAHLLOKOSA-N 0.000 claims 2
- LUYZNSYWWRRMFY-OAHLLOKOSA-N (2r)-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-2-hydroxy-2-phenylacetamide Chemical compound C1([C@H](C(=O)NC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)O)=CC=CC=C1 LUYZNSYWWRRMFY-OAHLLOKOSA-N 0.000 claims 2
- MDVFBZHBVUQEFG-GOSISDBHSA-N (2r)-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-2-hydroxy-2-phenylpropanamide Chemical compound C1([C@@](O)(C(=O)NC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)C)=CC=CC=C1 MDVFBZHBVUQEFG-GOSISDBHSA-N 0.000 claims 2
- LBUGZWJPFXKNGX-GFCCVEGCSA-N (2r)-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-2-hydroxy-3-methylbutanamide Chemical compound C1=CNC(=O)C2=C1C=C(NC(=O)[C@H](O)C(C)C)C(Cl)=C2 LBUGZWJPFXKNGX-GFCCVEGCSA-N 0.000 claims 2
- ZIZDTBAFVYQRCD-MRXNPFEDSA-N (2r)-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-2-methoxy-2-phenylacetamide Chemical compound C1([C@H](C(=O)NC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)OC)=CC=CC=C1 ZIZDTBAFVYQRCD-MRXNPFEDSA-N 0.000 claims 2
- DXMAQMGWRMJOAX-LLVKDONJSA-N (2r)-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-2-phenoxypropanamide Chemical compound O([C@H](C)C(=O)NC=1C(=CC=2C(=O)NC=CC=2C=1)Cl)C1=CC=CC=C1 DXMAQMGWRMJOAX-LLVKDONJSA-N 0.000 claims 2
- NCWXQEQIDGEPAD-GOSISDBHSA-N (2r)-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-2-phenyl-2-propan-2-yloxyacetamide Chemical compound C1([C@H](C(=O)NC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)OC(C)C)=CC=CC=C1 NCWXQEQIDGEPAD-GOSISDBHSA-N 0.000 claims 2
- QIXIMQMDBYEQGJ-GFCCVEGCSA-N (2r)-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)oxolane-2-carboxamide Chemical compound ClC1=CC(C(NC=C2)=O)=C2C=C1NC(=O)[C@H]1CCCO1 QIXIMQMDBYEQGJ-GFCCVEGCSA-N 0.000 claims 2
- CIJSISGZZDYHIK-GFCCVEGCSA-N (2r)-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)piperidine-2-carboxamide Chemical compound ClC1=CC(C(NC=C2)=O)=C2C=C1NC(=O)[C@H]1CCCCN1 CIJSISGZZDYHIK-GFCCVEGCSA-N 0.000 claims 2
- ASOKPJKABROLOA-LLVKDONJSA-N (2r)-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)pyrrolidine-2-carboxamide Chemical compound ClC1=CC(C(NC=C2)=O)=C2C=C1NC(=O)[C@H]1CCCN1 ASOKPJKABROLOA-LLVKDONJSA-N 0.000 claims 2
- MARASEZVJVDXJQ-INIZCTEOSA-N (2s)-2-amino-2-cyclohexyl-n-(7-methoxy-1-oxo-2h-isoquinolin-6-yl)acetamide Chemical compound C1([C@H](N)C(=O)NC2=CC3=C(C(NC=C3)=O)C=C2OC)CCCCC1 MARASEZVJVDXJQ-INIZCTEOSA-N 0.000 claims 2
- XAFGHLJJPKUZKI-AWEZNQCLSA-N (2s)-2-amino-n-(4-oxo-1h-quinazolin-7-yl)-3-phenylpropanamide Chemical compound C([C@H](N)C(=O)NC=1C=C2C(C(NC=N2)=O)=CC=1)C1=CC=CC=C1 XAFGHLJJPKUZKI-AWEZNQCLSA-N 0.000 claims 2
- LEQCZRIIDQNHNS-HNNXBMFYSA-N (2s)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-2-cyclohexylacetamide Chemical compound C1([C@H](N)C(=O)NC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)CCCCC1 LEQCZRIIDQNHNS-HNNXBMFYSA-N 0.000 claims 2
- BHVXQQAOHUXHJX-HNNXBMFYSA-N (2s)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-3-cyclohexylpropanamide Chemical compound C([C@H](N)C(=O)NC=1C(=CC=2C(=O)NC=CC=2C=1)Cl)C1CCCCC1 BHVXQQAOHUXHJX-HNNXBMFYSA-N 0.000 claims 2
- WXRZSOWZRRRJSB-LBPRGKRZSA-N (2s)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-3-methylbutanamide Chemical compound C1=CNC(=O)C2=C1C=C(NC(=O)[C@@H](N)C(C)C)C(Cl)=C2 WXRZSOWZRRRJSB-LBPRGKRZSA-N 0.000 claims 2
- MPPLZNXMOACWRV-HNNXBMFYSA-N (2s)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-3-phenylpropanamide Chemical compound C([C@H](N)C(=O)NC=1C(=CC=2C(=O)NC=CC=2C=1)Cl)C1=CC=CC=C1 MPPLZNXMOACWRV-HNNXBMFYSA-N 0.000 claims 2
- DEUSPAYNLHIUSL-LBPRGKRZSA-N (2s)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-4,4-dimethylpentanamide Chemical compound C1=CNC(=O)C2=C1C=C(NC(=O)[C@@H](N)CC(C)(C)C)C(Cl)=C2 DEUSPAYNLHIUSL-LBPRGKRZSA-N 0.000 claims 2
- RADQDLRYXIUSGX-LBPRGKRZSA-N (2s)-2-amino-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-4-methylpentanamide Chemical compound C1=CNC(=O)C2=C1C=C(NC(=O)[C@@H](N)CC(C)C)C(Cl)=C2 RADQDLRYXIUSGX-LBPRGKRZSA-N 0.000 claims 2
- OZTWJDXASSVZPZ-KRWDZBQOSA-N (2s)-2-methoxy-n-(7-methoxy-1-oxo-2h-isoquinolin-6-yl)-2-phenylacetamide Chemical compound C1([C@@H](C(=O)NC=2C(=CC=3C(=O)NC=CC=3C=2)OC)OC)=CC=CC=C1 OZTWJDXASSVZPZ-KRWDZBQOSA-N 0.000 claims 2
- ZDTCHBCAYSXSNH-SFHVURJKSA-N (2s)-n-(7-chloro-1-oxo-2h-isoquinolin-6-yl)-2-cyclohexyl-2-(propan-2-ylamino)acetamide Chemical compound C1([C@H](NC(C)C)C(=O)NC=2C(=CC=3C(=O)NC=CC=3C=2)Cl)CCCCC1 ZDTCHBCAYSXSNH-SFHVURJKSA-N 0.000 claims 2
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| WO2007008942A2 (en) * | 2005-07-11 | 2007-01-18 | Aerie Pharmaceuticals, Inc. | Phenylamino-acetic acid [1-(pyridin-4-yl)-methylidene]-hydrazide derivatives and related compounds as modulators of g protein-coupled receptor kinases for the treatment of eye diseases |
| ES2729424T3 (es) | 2006-09-20 | 2019-11-04 | Aerie Pharmaceuticals Inc | Inhibidores de Rho cinasa |
| EP2066619A2 (en) * | 2006-11-02 | 2009-06-10 | Arete Therapeutics, INC. | Soluble epoxide hydrolase inhibitors |
| US8455513B2 (en) | 2007-01-10 | 2013-06-04 | Aerie Pharmaceuticals, Inc. | 6-aminoisoquinoline compounds |
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| MY153756A (en) * | 2008-06-24 | 2015-03-13 | Sanofi Aventis | Bi-and polycyclic substituted isoquinoline and isoquinoline derivatives as rho kinase inhibitors |
| US8450344B2 (en) | 2008-07-25 | 2013-05-28 | Aerie Pharmaceuticals, Inc. | Beta- and gamma-amino-isoquinoline amide compounds and substituted benzamide compounds |
| JP5937353B2 (ja) * | 2008-08-19 | 2016-06-22 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプＪａｎｓｓｅｎ Ｐｈａｒｍａｃｅｕｔｉｃａ Ｎａａｍｌｏｚｅ Ｖｅｎｎｏｏｔｓｃｈａｐ | 冷感−メントール受容体拮抗剤 |
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| WO2012054367A1 (en) | 2010-10-19 | 2012-04-26 | Boehringer Ingelheim International Gmbh | Rho kinase inhibitors |
| CN103864684A (zh) * | 2012-12-07 | 2014-06-18 | 天津科技大学 | 一种新颖的3,4-二氢-1(2h)异喹啉类衍生物的合成与抗肿瘤药物的应用 |
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| KR102579582B1 (ko) | 2015-11-17 | 2023-09-15 | 에어리 파마슈티컬즈, 인코포레이티드 | 키나아제 억제제 및 이의 중간체의 제조 방법 |
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-
2007
- 2007-09-13 ES ES07814835T patent/ES2729424T3/es active Active
- 2007-09-13 EP EP12003567A patent/EP2526948A1/en not_active Withdrawn
- 2007-09-13 EP EP07814835.0A patent/EP2068878B1/en not_active Not-in-force
- 2007-09-13 WO PCT/US2007/078343 patent/WO2008036540A2/en not_active Ceased
- 2007-09-13 CA CA2664335A patent/CA2664335C/en active Active
- 2007-09-13 JP JP2009529306A patent/JP5235887B2/ja not_active Expired - Fee Related
- 2007-09-14 CL CL200702686A patent/CL2007002686A1/es unknown
- 2007-09-18 US US11/856,740 patent/US8809326B2/en active Active
- 2007-09-19 TW TW096134934A patent/TW200819133A/zh unknown
- 2007-09-19 AR ARP070104139A patent/AR062900A1/es not_active Application Discontinuation
-
2014
- 2014-08-18 US US14/461,597 patent/US20140357652A1/en not_active Abandoned
-
2015
- 2015-06-30 US US14/754,787 patent/US20150297581A1/en not_active Abandoned
-
2016
- 2016-04-29 US US15/142,448 patent/US20160243102A1/en not_active Abandoned
-
2017
- 2017-12-29 US US15/858,995 patent/US10624882B2/en active Active
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