NO330341B1 - N-arylsulfonyl-3-substituted indoler med serotoninreseptoraffinitet, deres fremstilling og farmasoytiske preparater inneholdende forbindelsene - Google Patents
N-arylsulfonyl-3-substituted indoler med serotoninreseptoraffinitet, deres fremstilling og farmasoytiske preparater inneholdende forbindelsene Download PDFInfo
- Publication number
- NO330341B1 NO330341B1 NO20052737A NO20052737A NO330341B1 NO 330341 B1 NO330341 B1 NO 330341B1 NO 20052737 A NO20052737 A NO 20052737A NO 20052737 A NO20052737 A NO 20052737A NO 330341 B1 NO330341 B1 NO 330341B1
- Authority
- NO
- Norway
- Prior art keywords
- ylmethyl
- methylpiperazin
- indole
- bromo
- methoxybenzenesulfonyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 150
- 238000002360 preparation method Methods 0.000 title claims description 15
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 title claims description 7
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 title claims description 7
- 150000002475 indoles Chemical class 0.000 title abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 149
- 238000006243 chemical reaction Methods 0.000 claims description 46
- -1 1-(2-bromo-4-methoxybenzenesulfonyl)-3-(4-(2-methoxybenzene-1-yl)pyrazin-1-ylmethyl)-1H-indole Chemical compound 0.000 claims description 22
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 9
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- WCMKMNBKLDQDMF-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]-5-nitroindole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C([N+]([O-])=O)C=C2C(CN2CCN(C)CC2)=C1 WCMKMNBKLDQDMF-UHFFFAOYSA-N 0.000 claims description 5
- SFBKTUOOHOUKIL-UHFFFAOYSA-N 5-bromo-1-(4-fluorophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(F)=CC=2)C2=CC=C(Br)C=C12 SFBKTUOOHOUKIL-UHFFFAOYSA-N 0.000 claims description 5
- 239000002775 capsule Substances 0.000 claims description 5
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005959 diazepanyl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 239000003826 tablet Substances 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- WDGCEXWXLYNQSC-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(Br)=CC=2)C2=CC=CC=C12 WDGCEXWXLYNQSC-UHFFFAOYSA-N 0.000 claims description 3
- NEIGVLDQFAWZRO-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-5-methoxy-3-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]indole;hydrochloride Chemical compound Cl.C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(F)=CC=2)C=C1CN(CC1)CCN1C1=CC=CC=C1OC NEIGVLDQFAWZRO-UHFFFAOYSA-N 0.000 claims description 3
- SERXWDAUKDFLTJ-UHFFFAOYSA-N 4-bromo-1-(4-fluorophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(F)=CC=2)C2=CC=CC(Br)=C12 SERXWDAUKDFLTJ-UHFFFAOYSA-N 0.000 claims description 3
- OESDAVYRNYTCPX-UHFFFAOYSA-N 5-bromo-1-(2-bromophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole;hydrochloride Chemical compound Cl.C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C(=CC=CC=2)Br)C2=CC=C(Br)C=C12 OESDAVYRNYTCPX-UHFFFAOYSA-N 0.000 claims description 3
- MLSFRWLIQYLIMA-UHFFFAOYSA-N 5-bromo-1-(4-methylphenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(C)=CC=2)C2=CC=C(Br)C=C12 MLSFRWLIQYLIMA-UHFFFAOYSA-N 0.000 claims description 3
- ITZXAFVDUMULRD-UHFFFAOYSA-N [1-(benzenesulfonyl)indol-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CN(S(=O)(=O)C=2C=CC=CC=2)C2=CC=CC=C12 ITZXAFVDUMULRD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- JQYKNCIRNONGBB-NRFANRHFSA-N (2r)-2-[1-(benzenesulfonyl)indol-3-yl]-2-(4-methylpiperazin-1-yl)acetonitrile Chemical compound C1CN(C)CCN1[C@@H](C#N)C1=CN(S(=O)(=O)C=2C=CC=CC=2)C2=CC=CC=C12 JQYKNCIRNONGBB-NRFANRHFSA-N 0.000 claims description 2
- GKJFEJXFQPSRMV-XMMPIXPASA-N (2s)-2-(4-methylpiperazin-1-yl)-2-[1-(4-propan-2-ylphenyl)sulfonylindol-3-yl]acetonitrile Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C([C@@H](C#N)N2CCN(C)CC2)=C1 GKJFEJXFQPSRMV-XMMPIXPASA-N 0.000 claims description 2
- DQANSWHWCTYCBO-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[1-(4-propan-2-ylphenyl)sulfonylindol-3-yl]methanone Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C(=O)N2CCN(C)CC2)=C1 DQANSWHWCTYCBO-UHFFFAOYSA-N 0.000 claims description 2
- WIMUDGQEEZMMBY-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[5-nitro-1-(4-propan-2-ylphenyl)sulfonylindol-3-yl]methanone Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=C([N+]([O-])=O)C=C2C(C(=O)N2CCN(C)CC2)=C1 WIMUDGQEEZMMBY-UHFFFAOYSA-N 0.000 claims description 2
- HKZXURTXMIWGRG-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(CN2CCN(C)CC2)=C1 HKZXURTXMIWGRG-UHFFFAOYSA-N 0.000 claims description 2
- ONISJWQWAHRUBV-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole;hydrochloride Chemical compound Cl.BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(CN2CCN(C)CC2)=C1 ONISJWQWAHRUBV-UHFFFAOYSA-N 0.000 claims description 2
- BDOQFSVMMKWZRV-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)sulfonyl-4,5,6-trichloro-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC(Cl)=C(Cl)C(Cl)=C2C(CN2CCN(C)CC2)=C1 BDOQFSVMMKWZRV-UHFFFAOYSA-N 0.000 claims description 2
- CUJACFWWRCFAMF-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]-5-nitroindole;hydrochloride Chemical compound Cl.C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C(=CC=CC=2)Br)C2=CC=C([N+]([O-])=O)C=C12 CUJACFWWRCFAMF-UHFFFAOYSA-N 0.000 claims description 2
- PTDMJHNCPAZVKF-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C(=CC=CC=2)Br)C2=CC=CC=C12 PTDMJHNCPAZVKF-UHFFFAOYSA-N 0.000 claims description 2
- FUONENOZCFRGSK-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-4,5,6-trichloro-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C(=CC=CC=2)Br)C2=CC(Cl)=C(Cl)C(Cl)=C12 FUONENOZCFRGSK-UHFFFAOYSA-N 0.000 claims description 2
- DXMCAONVYGAFSX-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-4,5,6-trichloro-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(Br)=CC=2)C2=CC(Cl)=C(Cl)C(Cl)=C12 DXMCAONVYGAFSX-UHFFFAOYSA-N 0.000 claims description 2
- GQJYYUAGLADWPG-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]-5-nitroindole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(F)=CC=2)C2=CC=C([N+]([O-])=O)C=C12 GQJYYUAGLADWPG-UHFFFAOYSA-N 0.000 claims description 2
- WYPLTVNNEJMOPP-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(F)=CC=2)C2=CC=CC=C12 WYPLTVNNEJMOPP-UHFFFAOYSA-N 0.000 claims description 2
- SDFBAGZQPYDGLT-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(C#N)C=C2C(CN2CCN(C)CC2)=C1 SDFBAGZQPYDGLT-UHFFFAOYSA-N 0.000 claims description 2
- HIMJPFQZTGXGGE-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(C)=CC=2)C2=CC=CC=C12 HIMJPFQZTGXGGE-UHFFFAOYSA-N 0.000 claims description 2
- CYEZCUPFDACBTO-UHFFFAOYSA-N 1-(4-propan-2-ylphenyl)sulfonylindole-3-carboxylic acid Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C(O)=O)=C1 CYEZCUPFDACBTO-UHFFFAOYSA-N 0.000 claims description 2
- YHMDTEYVOAWFLZ-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-[(4-methylpiperazin-1-yl)methyl]-5-nitroindole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC=CC=2)C2=CC=C([N+]([O-])=O)C=C12 YHMDTEYVOAWFLZ-UHFFFAOYSA-N 0.000 claims description 2
- UMAQHFAGJQAEBJ-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-bromo-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC=CC=2)C2=CC=C(Br)C=C12 UMAQHFAGJQAEBJ-UHFFFAOYSA-N 0.000 claims description 2
- HANNVHIWGICRKX-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-fluoro-3-[(4-methylpiperazin-1-yl)methyl]-2-phenylindole Chemical compound C1CN(C)CCN1CC(C1=CC(F)=CC=C1N1S(=O)(=O)C=2C=CC=CC=2)=C1C1=CC=CC=C1 HANNVHIWGICRKX-UHFFFAOYSA-N 0.000 claims description 2
- UMGHFQAQMBXVAN-UHFFFAOYSA-N 3-(1,4-diazepan-1-ylmethyl)-1-(4-propan-2-ylphenyl)sulfonylindole Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(CN2CCNCCC2)=C1 UMGHFQAQMBXVAN-UHFFFAOYSA-N 0.000 claims description 2
- WZOIYLIDQGPBSD-LJQANCHMSA-N 3-[(1r)-1-(4-methylpiperazin-1-yl)ethyl]-1-(4-propan-2-ylphenyl)sulfonylindole Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C([C@@H](C)N2CCN(C)CC2)=C1 WZOIYLIDQGPBSD-LJQANCHMSA-N 0.000 claims description 2
- ODNVEUZDOAIDRE-UHFFFAOYSA-N 3-[(4-benzylpiperazin-1-yl)methyl]-1-(4-methoxyphenyl)sulfonylindole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(CN2CCN(CC=3C=CC=CC=3)CC2)=C1 ODNVEUZDOAIDRE-UHFFFAOYSA-N 0.000 claims description 2
- ADYCVLZJDBHIQK-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-1-(4-propan-2-ylphenyl)sulfonylindole Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(CN2CCN(C)CC2)=C1 ADYCVLZJDBHIQK-UHFFFAOYSA-N 0.000 claims description 2
- LTGLXGRPCVVIPW-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1-(4-propan-2-ylphenyl)sulfonylindole Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=C([N+]([O-])=O)C=C2C(CN2CCN(C)CC2)=C1 LTGLXGRPCVVIPW-UHFFFAOYSA-N 0.000 claims description 2
- FROPHUURXFOJQT-UHFFFAOYSA-N 4,5,6-trichloro-3-[(4-methylpiperazin-1-yl)methyl]-1-(4-propan-2-ylphenyl)sulfonylindole Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC(Cl)=C(Cl)C(Cl)=C2C(CN2CCN(C)CC2)=C1 FROPHUURXFOJQT-UHFFFAOYSA-N 0.000 claims description 2
- MAHWTAWYWUXNJT-UHFFFAOYSA-N 4-bromo-1-(4-methoxyphenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC(Br)=C2C(CN2CCN(C)CC2)=C1 MAHWTAWYWUXNJT-UHFFFAOYSA-N 0.000 claims description 2
- UTTWFVZYEBGVAY-UHFFFAOYSA-N 4-bromo-3-[(4-methylpiperazin-1-yl)methyl]-1-(4-propan-2-ylphenyl)sulfonylindole Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=CC(Br)=C2C(CN2CCN(C)CC2)=C1 UTTWFVZYEBGVAY-UHFFFAOYSA-N 0.000 claims description 2
- DGNZIOXFWMMBAM-UHFFFAOYSA-N 5-bromo-1-(2-bromo-4-methoxyphenyl)sulfonyl-3-(1,4-diazepan-1-ylmethyl)indole Chemical compound BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Br)C=C2C(CN2CCNCCC2)=C1 DGNZIOXFWMMBAM-UHFFFAOYSA-N 0.000 claims description 2
- KDIAKBSMIXPZIZ-UHFFFAOYSA-N 5-bromo-1-(4-fluorophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(F)=CC=2)C2=CC=C(Br)C=C12 KDIAKBSMIXPZIZ-UHFFFAOYSA-N 0.000 claims description 2
- KVOUUCVOAGRQDR-UHFFFAOYSA-N 5-bromo-3-(1,4-diazepan-1-ylmethyl)-1-(4-methoxyphenyl)sulfonylindole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Br)C=C2C(CN2CCNCCC2)=C1 KVOUUCVOAGRQDR-UHFFFAOYSA-N 0.000 claims description 2
- NJSUZBDNWYETFW-UHFFFAOYSA-N 5-bromo-3-(1,4-diazepan-1-ylmethyl)-1-(4-methylphenyl)sulfonylindole Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=CC=C(Br)C=C2C(CN2CCNCCC2)=C1 NJSUZBDNWYETFW-UHFFFAOYSA-N 0.000 claims description 2
- ALNNCJRWRJREPL-UHFFFAOYSA-N 5-chloro-1-(4-fluorophenyl)sulfonyl-2-methyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=C(C)N(S(=O)(=O)C=2C=CC(F)=CC=2)C2=CC=C(Cl)C=C12 ALNNCJRWRJREPL-UHFFFAOYSA-N 0.000 claims description 2
- MSLVYEQHIRXQRE-UHFFFAOYSA-N 5-fluoro-1-(4-methylphenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]-2-phenylindole Chemical compound C1CN(C)CCN1CC(C1=CC(F)=CC=C1N1S(=O)(=O)C=2C=CC(C)=CC=2)=C1C1=CC=CC=C1 MSLVYEQHIRXQRE-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- BJQGJPQIONVXFR-UHFFFAOYSA-N [1-(2-bromophenyl)sulfonylindol-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CN(S(=O)(=O)C=2C(=CC=CC=2)Br)C2=CC=CC=C12 BJQGJPQIONVXFR-UHFFFAOYSA-N 0.000 claims description 2
- UEMFHQFJMMNSGC-UHFFFAOYSA-N [1-(4-fluorophenyl)sulfonyl-5-nitroindol-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CN(S(=O)(=O)C=2C=CC(F)=CC=2)C2=CC=C([N+]([O-])=O)C=C12 UEMFHQFJMMNSGC-UHFFFAOYSA-N 0.000 claims description 2
- CBWMDAWZLANJFW-UHFFFAOYSA-N [1-(4-methylphenyl)sulfonyl-5-nitroindol-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CN(S(=O)(=O)C=2C=CC(C)=CC=2)C2=CC=C([N+]([O-])=O)C=C12 CBWMDAWZLANJFW-UHFFFAOYSA-N 0.000 claims description 2
- WZCHGLJNLIHFMJ-UHFFFAOYSA-N benzyl 4-[[1-(benzenesulfonyl)indol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(CC=2C3=CC=CC=C3N(C=2)S(=O)(=O)C=2C=CC=CC=2)CCN1C(=O)OCC1=CC=CC=C1 WZCHGLJNLIHFMJ-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- GWCYPEHWIZXYFZ-UHFFFAOYSA-N masupirdine Chemical compound C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C(=CC=CC=2)Br)C=C1CN1CCN(C)CC1 GWCYPEHWIZXYFZ-UHFFFAOYSA-N 0.000 claims description 2
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- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- 230000008733 trauma Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
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- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
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- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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- 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
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- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
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- 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
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Public Health (AREA)
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- Pharmacology & Pharmacy (AREA)
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Applications Claiming Priority (2)
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IN884MA2002 | 2002-11-28 | ||
PCT/IN2003/000209 WO2004048330A1 (en) | 2002-11-28 | 2003-06-05 | N-arylsulfonyl-3-substituted indoles having serotonin receptor affinity, process for their preparation and pharmaceutical composition containing them |
Publications (3)
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NO20052737D0 NO20052737D0 (no) | 2005-06-08 |
NO20052737L NO20052737L (no) | 2005-08-25 |
NO330341B1 true NO330341B1 (no) | 2011-03-28 |
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NO20052737A NO330341B1 (no) | 2002-11-28 | 2005-06-08 | N-arylsulfonyl-3-substituted indoler med serotoninreseptoraffinitet, deres fremstilling og farmasoytiske preparater inneholdende forbindelsene |
NO20085054A NO335015B1 (no) | 2002-11-28 | 2008-12-05 | Fremgangsmåte for fremstilling av 5-HT(serotonin)-ligander |
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NO20085054A NO335015B1 (no) | 2002-11-28 | 2008-12-05 | Fremgangsmåte for fremstilling av 5-HT(serotonin)-ligander |
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US (1) | US7875605B2 (pt) |
EP (1) | EP1581492B1 (pt) |
JP (1) | JP4559230B2 (pt) |
KR (1) | KR100818508B1 (pt) |
CN (2) | CN1720225B (pt) |
AT (1) | ATE401307T1 (pt) |
AU (1) | AU2003237599B2 (pt) |
BR (2) | BRPI0318799B8 (pt) |
CA (1) | CA2509982C (pt) |
CY (1) | CY1108786T1 (pt) |
DE (1) | DE60322266D1 (pt) |
DK (1) | DK1581492T3 (pt) |
EA (1) | EA011320B1 (pt) |
ES (1) | ES2310243T3 (pt) |
HK (2) | HK1133002A1 (pt) |
MX (1) | MXPA05005701A (pt) |
NO (2) | NO330341B1 (pt) |
NZ (2) | NZ572186A (pt) |
PT (1) | PT1581492E (pt) |
SI (1) | SI1581492T1 (pt) |
WO (1) | WO2004048330A1 (pt) |
ZA (1) | ZA200504043B (pt) |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
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AU2003208711A1 (en) * | 2002-02-12 | 2003-09-04 | Akzo Nobel N.V. | 1-arylsulfonyl-3-substituted indole and indoline derivatives useful in the treatment of central nervous system disorders |
WO2005005439A1 (en) * | 2003-07-09 | 2005-01-20 | Suven Life Sciences Limited | Benzothiazino indoles |
KR101049868B1 (ko) | 2004-01-02 | 2011-07-19 | 수벤 라이프 사이언시스 리미티드 | 신규한 인데노[2,1a]인덴 및 이소인돌[2,1-a]인돌 |
AU2006274884B2 (en) | 2005-07-29 | 2012-04-05 | F. Hoffmann-La Roche Ag | Indol-3-yl-carbonyl-piperidin and piperazin derivatives |
WO2007020653A1 (en) * | 2005-08-12 | 2007-02-22 | Suven Life Sciences Limited | Thioether derivatives as functional 5-ht6 ligands |
NZ566495A (en) | 2005-08-12 | 2010-06-25 | Suven Life Sciences Ltd | Aminoaryl sulphonamide derivatives as functional 5-HT6 ligands |
KR101250820B1 (ko) | 2005-08-16 | 2013-04-04 | 수벤 라이프 사이언시스 리미티드 | 개선된 로사르탄 제조 방법 |
AU2007343062B2 (en) * | 2007-01-08 | 2011-02-10 | Suven Life Sciences Limited | 4-(Heterocyclyl)alkyl-N-(arylsulfonyl) indole compounds and their use as 5-HT6 ligands |
WO2008084492A1 (en) | 2007-01-08 | 2008-07-17 | Suven Life Sciences Limited | 5-(heterocyclyl)alkyl-n-(arylsulfonyl)indole compounds and their use as 5-ht6 ligands |
MX2009011461A (es) | 2007-05-03 | 2009-11-10 | Suven Life Sciences Ltd | Compuestos de aminoalcoxiarilsulfonamida y su uso como ligandos de la 5-hidroxitriptamina6. |
WO2008144263A1 (en) * | 2007-05-18 | 2008-11-27 | The Ohio State University Research Foundation | Potent indole-3-carbinol-derived antitumor agents |
CA2703157C (en) | 2007-10-26 | 2013-02-05 | Suven Life Sciences Limited | Amino arylsulfonamide compounds and their use as 5-ht6 ligands |
WO2010032257A1 (en) | 2008-09-17 | 2010-03-25 | Suven Life Sciences Limited | Aryl indolyl sulfonamide compounds and their use as 5-ht6 ligands |
EA019496B1 (ru) | 2008-09-17 | 2014-04-30 | Сувен Лайф Сайенсиз Лимитед | Арилсульфонамидные аминосоединения и их применение в качестве лигандов 5-ht |
EP2464227A4 (en) * | 2009-08-10 | 2013-02-20 | Galenea Corp | COMPOUNDS AND METHODS OF USE |
US8153680B2 (en) * | 2009-08-25 | 2012-04-10 | The Ohio State University Research Foundation | Alkyl indole-3-carbinol-derived antitumor agents |
KR101463190B1 (ko) | 2010-01-05 | 2014-11-18 | 수벤 라이프 사이언시스 리미티드 | 5ht6 수용체 리간드인 술폰 화합물 |
CN102093149A (zh) * | 2010-12-08 | 2011-06-15 | 天津理工大学 | 一种促进氰基快速水解制备羧酸类化合物的方法 |
US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
US9394285B2 (en) | 2013-03-15 | 2016-07-19 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
KR101534136B1 (ko) * | 2013-06-11 | 2015-07-07 | 이화여자대학교 산학협력단 | 인돌 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 포함하는 5-ht6 수용체 관련 질환의 예방 또는 치료용 약학적 조성물 |
AU2014358682B2 (en) | 2013-12-02 | 2016-10-20 | Suven Life Sciences Limited | Process for large scale production of 1-[(2-bromophenyl)sulfonyl]-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]-1H-indole dimesylate monohydrate |
WO2015090233A1 (en) | 2013-12-20 | 2015-06-25 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic compounds and their application in pharmaceuticals |
AU2015286049B2 (en) | 2014-07-08 | 2018-03-01 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic derivatives and pharmaceutical applications thereof |
PL3180001T3 (pl) * | 2014-08-16 | 2019-07-31 | Suven Life Sciences Limited | Aktywny metabolit monohydrat dimesylanu 1-[(2-bromofenylo)sulfonylo]-5-metoksy-3-[(4-metylo-1-piperazynylo)metylo]-1h-indolu oraz sól dihydrat dimesylanu aktywnego metabolitu |
EA038087B1 (ru) | 2016-05-18 | 2021-07-05 | Сувен Лайф Сайенсиз Лимитед | Трехкомпонентная фармацевтическая комбинация чистых антагонистов 5-ht6 рецепторов, ингибиторов ацетилхолинэстеразы и антагониста nmda рецептора, применение указанной комбинации и содержащей ее фармацевтической композиции в лечении когнитивных расстройств и способ такого лечения |
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CN109069449A (zh) * | 2016-05-18 | 2018-12-21 | 苏文生命科学有限公司 | 纯5-ht6受体拮抗剂与nmda受体拮抗剂的组合 |
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