JP3690423B2 - 置換イソキノリン誘導体およびその抗痙攣薬としての使用 - Google Patents
置換イソキノリン誘導体およびその抗痙攣薬としての使用 Download PDFInfo
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- JP3690423B2 JP3690423B2 JP54024898A JP54024898A JP3690423B2 JP 3690423 B2 JP3690423 B2 JP 3690423B2 JP 54024898 A JP54024898 A JP 54024898A JP 54024898 A JP54024898 A JP 54024898A JP 3690423 B2 JP3690423 B2 JP 3690423B2
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- JP
- Japan
- Prior art keywords
- tetrahydroisoquinolin
- methyl
- iso
- bromo
- trifluoromethylbenzamide
- 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.)
- Expired - Fee Related
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- 239000001961 anticonvulsive agent Substances 0.000 title description 9
- 229940125681 anticonvulsant agent Drugs 0.000 title description 7
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical group 0.000 claims description 146
- -1 methoxyethyl Chemical group 0.000 claims description 68
- 238000002360 preparation method Methods 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000012458 free base Substances 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 208000019695 Migraine disease Diseases 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 206010027599 migraine Diseases 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- CCPKEDYVKFPFIM-UHFFFAOYSA-N n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-4h-benzotriazole-5-carboxamide Chemical compound C1=C2N=NN=C2CC(C(=O)NC2=CC=C3CCN(CC3=C2)C)=C1 CCPKEDYVKFPFIM-UHFFFAOYSA-N 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- HSAUNWQVISCPTB-UHFFFAOYSA-N 4-methoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 HSAUNWQVISCPTB-UHFFFAOYSA-N 0.000 claims description 5
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 208000014617 hemorrhoid Diseases 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- JCMGCQYTXXDTIA-UHFFFAOYSA-N 2,4-dichloro-5-fluoro-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC(F)=C(Cl)C=C1Cl JCMGCQYTXXDTIA-UHFFFAOYSA-N 0.000 claims description 3
- MBACTHKEPMCGMB-UHFFFAOYSA-N 2,4-difluoro-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC=C(F)C=C1F MBACTHKEPMCGMB-UHFFFAOYSA-N 0.000 claims description 3
- VCMRMCDXNASICA-UHFFFAOYSA-N 2-bromo-5-methoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound COC1=CC=C(Br)C(C(=O)NC=2C=C3CN(C)CCC3=CC=2)=C1 VCMRMCDXNASICA-UHFFFAOYSA-N 0.000 claims description 3
- WUCLAEZPVSJCFI-UHFFFAOYSA-N 2-fluoro-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-4-(trifluoromethyl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1F WUCLAEZPVSJCFI-UHFFFAOYSA-N 0.000 claims description 3
- IZTGCMASDIMYQY-UHFFFAOYSA-N 2-methyl-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-1,3-thiazole-4-carboxamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CSC(C)=N1 IZTGCMASDIMYQY-UHFFFAOYSA-N 0.000 claims description 3
- WQYHZEJGOFBCIR-UHFFFAOYSA-N 2-methyl-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C2N=C(C)NC2=CC(C(=O)NC2=CC=C3CCN(CC3=C2)C)=C1 WQYHZEJGOFBCIR-UHFFFAOYSA-N 0.000 claims description 3
- AHONRCXNXUBHGE-UHFFFAOYSA-N 3,4,5-trimethoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NC=2C=C3CN(C)CCC3=CC=2)=C1 AHONRCXNXUBHGE-UHFFFAOYSA-N 0.000 claims description 3
- ROSUGOYJPULAHG-UHFFFAOYSA-N 3,4-dichloro-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 ROSUGOYJPULAHG-UHFFFAOYSA-N 0.000 claims description 3
- VBZOEGVIYRLDGL-UHFFFAOYSA-N 3,4-dimethoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 VBZOEGVIYRLDGL-UHFFFAOYSA-N 0.000 claims description 3
- YUTJCNKMAKHBSJ-UHFFFAOYSA-N 3,5-dichloro-4-ethoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(Cl)C(OCC)=C(Cl)C=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 YUTJCNKMAKHBSJ-UHFFFAOYSA-N 0.000 claims description 3
- VSQFXCNKXMKHLX-UHFFFAOYSA-N 3,5-dichloro-4-methoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(Cl)C(OC)=C(Cl)C=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 VSQFXCNKXMKHLX-UHFFFAOYSA-N 0.000 claims description 3
- UXFHHLFKDLCOIA-UHFFFAOYSA-N 3,5-dichloro-N-(2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)-4-propan-2-yloxybenzamide Chemical compound C1=C(Cl)C(OC(C)C)=C(Cl)C=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 UXFHHLFKDLCOIA-UHFFFAOYSA-N 0.000 claims description 3
- WZDHWRAXEPEQIF-UHFFFAOYSA-N 3-(2,2-dimethylpropanoyl)-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC=CC(C(=O)C(C)(C)C)=C1 WZDHWRAXEPEQIF-UHFFFAOYSA-N 0.000 claims description 3
- WODUVNIZGNEYGM-UHFFFAOYSA-N 3-bromo-4-ethoxy-n-(2-ethyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(Br)C(OCC)=CC=C1C(=O)NC1=CC=C(CCN(CC)C2)C2=C1 WODUVNIZGNEYGM-UHFFFAOYSA-N 0.000 claims description 3
- NQOGZKWMBKMMCO-UHFFFAOYSA-N 3-bromo-4-ethoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(Br)C(OCC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 NQOGZKWMBKMMCO-UHFFFAOYSA-N 0.000 claims description 3
- JIVMWVCRPHFWMT-UHFFFAOYSA-N 3-bromo-4-ethoxy-n-(2-propan-2-yl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(Br)C(OCC)=CC=C1C(=O)NC1=CC=C(CCN(C2)C(C)C)C2=C1 JIVMWVCRPHFWMT-UHFFFAOYSA-N 0.000 claims description 3
- ABYWTYKLGUDGTE-UHFFFAOYSA-N 3-bromo-4-ethoxy-n-(2-propyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C2CN(CCC)CCC2=CC=C1NC(=O)C1=CC=C(OCC)C(Br)=C1 ABYWTYKLGUDGTE-UHFFFAOYSA-N 0.000 claims description 3
- IPTKPOYVYGXQHL-UHFFFAOYSA-N 3-bromo-4-ethoxy-n-[1-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]benzamide Chemical compound C1=C(Br)C(OCC)=CC=C1C(=O)NC1=CC=C(CCNC2CCO)C2=C1 IPTKPOYVYGXQHL-UHFFFAOYSA-N 0.000 claims description 3
- TXOBRBUJCQAAJE-UHFFFAOYSA-N 3-bromo-4-ethyl-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(Br)C(CC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 TXOBRBUJCQAAJE-UHFFFAOYSA-N 0.000 claims description 3
- HSXULVSXQLODTJ-UHFFFAOYSA-N 3-bromo-4-ethyl-n-[1-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]benzamide Chemical compound C1=C(Br)C(CC)=CC=C1C(=O)NC1=CC=C(CCNC2CCO)C2=C1 HSXULVSXQLODTJ-UHFFFAOYSA-N 0.000 claims description 3
- DLNWMRLSPRJTSM-UHFFFAOYSA-N 3-bromo-4-methoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(Br)C(OC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 DLNWMRLSPRJTSM-UHFFFAOYSA-N 0.000 claims description 3
- MARKGZBKHMNDHK-UHFFFAOYSA-N 3-bromo-4-methoxy-n-[2-methyl-5-[(2,2,2-trifluoroacetyl)amino]-3,4-dihydro-1h-isoquinolin-7-yl]benzamide Chemical compound C1=C(Br)C(OC)=CC=C1C(=O)NC(C=C1NC(=O)C(F)(F)F)=CC2=C1CCN(C)C2 MARKGZBKHMNDHK-UHFFFAOYSA-N 0.000 claims description 3
- YLODOYNAZKGDST-UHFFFAOYSA-N 3-bromo-4-methyl-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC=C(C)C(Br)=C1 YLODOYNAZKGDST-UHFFFAOYSA-N 0.000 claims description 3
- WKYPTSUUBBODME-UHFFFAOYSA-N 3-bromo-4-tert-butyl-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC=C(C(C)(C)C)C(Br)=C1 WKYPTSUUBBODME-UHFFFAOYSA-N 0.000 claims description 3
- RBJNQWHVTNFMSK-UHFFFAOYSA-N 3-bromo-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-4-propan-2-yloxybenzamide Chemical compound C1=C(Br)C(OC(C)C)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 RBJNQWHVTNFMSK-UHFFFAOYSA-N 0.000 claims description 3
- NZYJXJUCONRBMI-UHFFFAOYSA-N 3-bromo-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-4-propoxybenzamide Chemical compound C1=C(Br)C(OCCC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 NZYJXJUCONRBMI-UHFFFAOYSA-N 0.000 claims description 3
- VOSHURDHUZSVNH-UHFFFAOYSA-N 3-bromo-n-(5-chloro-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-4-ethoxybenzamide Chemical compound C1=C(Br)C(OCC)=CC=C1C(=O)NC1=CC(Cl)=C(CCN(C)C2)C2=C1 VOSHURDHUZSVNH-UHFFFAOYSA-N 0.000 claims description 3
- SVFLVFCOGYPJRC-UHFFFAOYSA-N 3-bromo-n-(5-chloro-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-4-ethylbenzamide Chemical compound C1=C(Br)C(CC)=CC=C1C(=O)NC1=CC(Cl)=C(CCN(C)C2)C2=C1 SVFLVFCOGYPJRC-UHFFFAOYSA-N 0.000 claims description 3
- QPPSHURYJFZBTG-UHFFFAOYSA-N 3-bromo-n-[1-(2-methoxyethyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]-4-propan-2-yloxybenzamide Chemical compound C1=C2C(CCOC)NCCC2=CC=C1NC(=O)C1=CC=C(OC(C)C)C(Br)=C1 QPPSHURYJFZBTG-UHFFFAOYSA-N 0.000 claims description 3
- RBLZLTYJGFEDPG-UHFFFAOYSA-N 3-chloro-4-ethoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(Cl)C(OCC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 RBLZLTYJGFEDPG-UHFFFAOYSA-N 0.000 claims description 3
- IGKVLSYWWDHPOE-UHFFFAOYSA-N 3-chloro-4-methoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(Cl)C(OC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 IGKVLSYWWDHPOE-UHFFFAOYSA-N 0.000 claims description 3
- LBVUZNHYORMEDH-UHFFFAOYSA-N 3-chloro-4-propan-2-yloxy-n-(2-propyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C2CN(CCC)CCC2=CC=C1NC(=O)C1=CC=C(OC(C)C)C(Cl)=C1 LBVUZNHYORMEDH-UHFFFAOYSA-N 0.000 claims description 3
- JFWNAKLXGSTVEN-UHFFFAOYSA-N 3-chloro-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-4-propan-2-yloxybenzamide Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 JFWNAKLXGSTVEN-UHFFFAOYSA-N 0.000 claims description 3
- PMTOIIMQZMMEPR-UHFFFAOYSA-N 3-chloro-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC=CC(Cl)=C1 PMTOIIMQZMMEPR-UHFFFAOYSA-N 0.000 claims description 3
- BAQDRXAJWIEXSH-UHFFFAOYSA-N 3-chloro-n-[1-(2-methoxyethyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]-4-propan-2-yloxybenzamide Chemical compound C1=C2C(CCOC)NCCC2=CC=C1NC(=O)C1=CC=C(OC(C)C)C(Cl)=C1 BAQDRXAJWIEXSH-UHFFFAOYSA-N 0.000 claims description 3
- KFNMVJFJHCQFAI-UHFFFAOYSA-N 3-cyano-4-ethoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(C#N)C(OCC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 KFNMVJFJHCQFAI-UHFFFAOYSA-N 0.000 claims description 3
- YGIWQHCHDAZZRM-UHFFFAOYSA-N 3-cyano-4-methoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(C#N)C(OC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 YGIWQHCHDAZZRM-UHFFFAOYSA-N 0.000 claims description 3
- IQMYJOKMFLMIFJ-UHFFFAOYSA-N 3-cyano-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-4-propoxybenzamide Chemical compound C1=C(C#N)C(OCCC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 IQMYJOKMFLMIFJ-UHFFFAOYSA-N 0.000 claims description 3
- NHPCPNPHLXGHFS-UHFFFAOYSA-N 3-cyano-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC=CC(C#N)=C1 NHPCPNPHLXGHFS-UHFFFAOYSA-N 0.000 claims description 3
- NCCKLCVNZPYCBA-UHFFFAOYSA-N 3-fluoro-4-methoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(F)C(OC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 NCCKLCVNZPYCBA-UHFFFAOYSA-N 0.000 claims description 3
- FRWYQIFMKDKPRJ-UHFFFAOYSA-N 3-fluoro-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-5-(trifluoromethyl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC(F)=CC(C(F)(F)F)=C1 FRWYQIFMKDKPRJ-UHFFFAOYSA-N 0.000 claims description 3
- KSTPICVDHFVDGJ-UHFFFAOYSA-N 3-fluoro-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC=CC(F)=C1 KSTPICVDHFVDGJ-UHFFFAOYSA-N 0.000 claims description 3
- BGJHNIOVHWNFSB-UHFFFAOYSA-N 3-iodo-4-methoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(I)C(OC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 BGJHNIOVHWNFSB-UHFFFAOYSA-N 0.000 claims description 3
- SEQYMQFQAYVQCZ-UHFFFAOYSA-N 3-methyl-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC=CC(C)=C1 SEQYMQFQAYVQCZ-UHFFFAOYSA-N 0.000 claims description 3
- OAIRIOONPZRTFJ-UHFFFAOYSA-N 4-(cyclopropylmethoxy)-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C(C=C1)=CC=C1OCC1CC1 OAIRIOONPZRTFJ-UHFFFAOYSA-N 0.000 claims description 3
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- XUKUHJRTPYTFCV-UHFFFAOYSA-N 4-cyclopentyloxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C(C=C1)=CC=C1OC1CCCC1 XUKUHJRTPYTFCV-UHFFFAOYSA-N 0.000 claims description 3
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- XJYGKTKHKCKQFV-UHFFFAOYSA-N 4-ethoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=CC(OCC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 XJYGKTKHKCKQFV-UHFFFAOYSA-N 0.000 claims description 3
- GNWPNIZCZCNTEZ-UHFFFAOYSA-N 4-ethyl-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-3-methylsulfonylbenzamide Chemical compound C1=C(S(C)(=O)=O)C(CC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 GNWPNIZCZCNTEZ-UHFFFAOYSA-N 0.000 claims description 3
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- HANAXEWRZIUBJG-UHFFFAOYSA-N tert-butyl 7-[(4-azidobenzoyl)amino]-5-iodo-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1=C2CN(C(=O)OC(C)(C)C)CCC2=C(I)C=C1NC(=O)C1=CC=C(N=[N+]=[N-])C=C1 HANAXEWRZIUBJG-UHFFFAOYSA-N 0.000 description 1
- HVIVDQNMQAUBRV-UHFFFAOYSA-N tert-butyl 7-[(5-chlorothiophene-2-carbonyl)amino]-3,4-dihydro-1H-isoquinoline-2-carboxylate 5-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)c1ccc(Cl)s1.CC(C)(C)OC(=O)N1CCc2ccc(NC(=O)c3ccc(Cl)s3)cc2C1 HVIVDQNMQAUBRV-UHFFFAOYSA-N 0.000 description 1
- AGRBXKCSGCUXST-UHFFFAOYSA-N tert-butyl 7-amino-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1=C(N)C=C2CN(C(=O)OC(C)(C)C)CCC2=C1 AGRBXKCSGCUXST-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical class OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Psychology (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9705619.6A GB9705619D0 (en) | 1997-03-18 | 1997-03-18 | Novel compounds |
GB9705619.6 | 1997-03-18 | ||
GB9726695.1 | 1997-12-17 | ||
GBGB9726695.1A GB9726695D0 (en) | 1997-12-17 | 1997-12-17 | Novel compounds |
PCT/GB1998/000782 WO1998041508A1 (en) | 1997-03-18 | 1998-03-16 | Substituted isoquinoline derivatives and their use as anticonvulsants |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2001515504A JP2001515504A (ja) | 2001-09-18 |
JP3690423B2 true JP3690423B2 (ja) | 2005-08-31 |
Family
ID=26311215
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP54024898A Expired - Fee Related JP3690423B2 (ja) | 1997-03-18 | 1998-03-16 | 置換イソキノリン誘導体およびその抗痙攣薬としての使用 |
Country Status (16)
Country | Link |
---|---|
EP (1) | EP0968190A1 (tr) |
JP (1) | JP3690423B2 (tr) |
KR (1) | KR100568654B1 (tr) |
CN (1) | CN1183116C (tr) |
AR (1) | AR012092A1 (tr) |
AU (1) | AU737955B2 (tr) |
BR (1) | BR9809047A (tr) |
CA (1) | CA2284218A1 (tr) |
CO (1) | CO4950553A1 (tr) |
IL (1) | IL131756A0 (tr) |
NO (1) | NO314081B1 (tr) |
NZ (1) | NZ337424A (tr) |
PL (1) | PL192116B1 (tr) |
TR (1) | TR199902283T2 (tr) |
TW (1) | TW555694B (tr) |
WO (1) | WO1998041508A1 (tr) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9726695D0 (en) * | 1997-12-17 | 1998-02-18 | Smithkline Beecham Plc | Novel compounds |
WO1999021836A1 (en) * | 1997-10-24 | 1999-05-06 | Smithkline Beecham Plc | Substituted isoquinoline derivatives and their use as anticonvulsants |
GB9817424D0 (en) | 1998-08-11 | 1998-10-07 | Smithkline Beecham Plc | Novel compounds |
US20020006908A1 (en) * | 1998-12-03 | 2002-01-17 | Daniel P. Van Kammen | Anticonvulsant derivatives useful in treating schizophrenia |
EP1177188B1 (en) * | 1999-05-12 | 2005-10-12 | Ortho-McNeil Pharmaceutical, Inc. | Pyrazole carboxamides useful for the treatment of obesity and other disorders |
GB9915589D0 (en) * | 1999-07-02 | 1999-09-01 | Smithkline Beecham Plc | Novel compounds |
FR2795724B1 (fr) * | 1999-07-02 | 2002-12-13 | Sanofi Synthelabo | Nouveaux derives du benzene, un procede pour leur preparation et les compositions pharmaceutiques les contenant |
EP2033953A1 (en) * | 2002-02-15 | 2009-03-11 | Glaxo Group Limited | Vanilloid receptor modulators |
GB0210762D0 (en) * | 2002-05-10 | 2002-06-19 | Glaxo Group Ltd | Compounds |
WO2004014388A1 (en) * | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | 6,6-fused heteroaryl derivatives as matrix metalloproteinase inhibitors |
GB0226724D0 (en) * | 2002-11-15 | 2002-12-24 | Merck Sharp & Dohme | Therapeutic agents |
MXPA05013434A (es) | 2003-06-12 | 2006-03-17 | Astellas Pharma Inc | Derivados de benzamida o sal del mismo. |
GB2406856B (en) * | 2003-10-07 | 2005-10-19 | Renovis Inc | Amide compounds as ion channel ligands and uses thereof |
GB2413129A (en) * | 2003-10-07 | 2005-10-19 | Renovis Inc | Aromatic amide compounds as ion channel ligands and uses thereof |
CA2553968A1 (en) * | 2004-01-23 | 2005-08-11 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments of inflammatory and neuropathic pain |
JP2008513426A (ja) * | 2004-09-20 | 2008-05-01 | バイオリポックス エービー | 炎症の治療に有用なピラゾール化合物 |
SE0403117D0 (sv) * | 2004-12-21 | 2004-12-21 | Astrazeneca Ab | New compounds 1 |
DK2046787T3 (da) | 2006-08-01 | 2011-07-18 | Glaxo Group Ltd | Pyrazolo[3,4-B]pyridin-forbindelser, og deres anvendelse som PDE4-inhibitorer |
CN106608901B (zh) * | 2015-10-22 | 2020-10-16 | 彭莉 | 二羟基二甲基四氢异喹啉-3-甲酰-Lys(Lys-Ala),其合成,活性及应用 |
CN111138359A (zh) * | 2020-01-19 | 2020-05-12 | 浙江农林大学暨阳学院 | 制备3-羰基-4-叠氮基-n-苯磺酰基-1,2,3,4-四氢异喹啉类化合物的方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4022900A (en) * | 1970-09-09 | 1977-05-10 | Marion Laboratories, Inc. | Compositions containing 1,2,3,4-tetrahydroisoquinolines used as hypotensive agents |
PL330465A1 (en) * | 1996-06-17 | 1999-05-24 | Smithkline Beecham Plc | Substituted benzamide derivatives and their application as anticonvulsants |
-
1998
- 1998-03-16 BR BR9809047-0A patent/BR9809047A/pt not_active Application Discontinuation
- 1998-03-16 JP JP54024898A patent/JP3690423B2/ja not_active Expired - Fee Related
- 1998-03-16 WO PCT/GB1998/000782 patent/WO1998041508A1/en not_active Application Discontinuation
- 1998-03-16 NZ NZ337424A patent/NZ337424A/en unknown
- 1998-03-16 AU AU64128/98A patent/AU737955B2/en not_active Ceased
- 1998-03-16 CN CNB988048809A patent/CN1183116C/zh not_active Expired - Fee Related
- 1998-03-16 CA CA002284218A patent/CA2284218A1/en not_active Abandoned
- 1998-03-16 KR KR1019997008443A patent/KR100568654B1/ko not_active IP Right Cessation
- 1998-03-16 TR TR1999/02283T patent/TR199902283T2/tr unknown
- 1998-03-16 PL PL335676A patent/PL192116B1/pl unknown
- 1998-03-16 IL IL13175698A patent/IL131756A0/xx active IP Right Grant
- 1998-03-16 EP EP98909647A patent/EP0968190A1/en not_active Withdrawn
- 1998-03-17 AR ARP980101199A patent/AR012092A1/es unknown
- 1998-03-18 CO CO98015157A patent/CO4950553A1/es unknown
- 1998-03-20 TW TW087104135A patent/TW555694B/zh not_active IP Right Cessation
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1999
- 1999-09-17 NO NO19994510A patent/NO314081B1/no unknown
Also Published As
Publication number | Publication date |
---|---|
KR20000076342A (ko) | 2000-12-26 |
TW555694B (en) | 2003-10-01 |
PL335676A1 (en) | 2000-05-08 |
IL131756A0 (en) | 2001-03-19 |
AU737955B2 (en) | 2001-09-06 |
KR100568654B1 (ko) | 2006-04-07 |
EP0968190A1 (en) | 2000-01-05 |
CO4950553A1 (es) | 2000-09-01 |
JP2001515504A (ja) | 2001-09-18 |
CN1255124A (zh) | 2000-05-31 |
BR9809047A (pt) | 2000-08-01 |
AU6412898A (en) | 1998-10-12 |
WO1998041508A1 (en) | 1998-09-24 |
CN1183116C (zh) | 2005-01-05 |
NZ337424A (en) | 2001-08-31 |
PL192116B1 (pl) | 2006-08-31 |
NO994510L (no) | 1999-09-17 |
NO314081B1 (no) | 2003-01-27 |
NO994510D0 (no) | 1999-09-17 |
TR199902283T2 (tr) | 1999-12-21 |
CA2284218A1 (en) | 1998-09-24 |
AR012092A1 (es) | 2000-09-27 |
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