JP2006514011A5 - - Google Patents
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- Publication number
- JP2006514011A5 JP2006514011A5 JP2004554900A JP2004554900A JP2006514011A5 JP 2006514011 A5 JP2006514011 A5 JP 2006514011A5 JP 2004554900 A JP2004554900 A JP 2004554900A JP 2004554900 A JP2004554900 A JP 2004554900A JP 2006514011 A5 JP2006514011 A5 JP 2006514011A5
- Authority
- JP
- Japan
- Prior art keywords
- indole
- ylmethyl
- methylpiperazin
- bromo
- indol
- 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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- -1 R 14 Chemical compound 0.000 claims 47
- 150000001875 compounds Chemical class 0.000 claims 25
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- 238000000034 method Methods 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 6
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 6
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 150000001602 bicycloalkyls Chemical group 0.000 claims 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 4
- 208000024891 symptom Diseases 0.000 claims 4
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 3
- ZLVCPTKXUQFVSO-UHFFFAOYSA-N 2-[1-(4-methoxyphenyl)sulfonylindol-3-yl]-2-(4-methylpiperazin-1-yl)acetonitrile Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C(C#N)N2CCN(C)CC2)=C1 ZLVCPTKXUQFVSO-UHFFFAOYSA-N 0.000 claims 3
- JQYKNCIRNONGBB-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)indol-3-yl]-2-(4-methylpiperazin-1-yl)acetonitrile Chemical compound C1CN(C)CCN1C(C#N)C1=CN(S(=O)(=O)C=2C=CC=CC=2)C2=CC=CC=C12 JQYKNCIRNONGBB-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000004442 acylamino group Chemical group 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 3
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims 3
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 3
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 3
- 125000001769 aryl amino group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 125000004986 diarylamino group Chemical group 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 208000019116 sleep disease Diseases 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 3
- 238000011282 treatment Methods 0.000 claims 3
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims 2
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 206010013654 Drug abuse Diseases 0.000 claims 2
- 206010019196 Head injury Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 206010026749 Mania Diseases 0.000 claims 2
- 208000026139 Memory disease Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 206010033664 Panic attack Diseases 0.000 claims 2
- 206010034010 Parkinsonism Diseases 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 206010037211 Psychomotor hyperactivity Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 208000020339 Spinal injury Diseases 0.000 claims 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 206010047700 Vomiting Diseases 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 238000002512 chemotherapy Methods 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 230000001149 cognitive effect Effects 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000002496 gastric effect Effects 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 2
- 125000002346 iodo group Chemical group I* 0.000 claims 2
- 208000024714 major depressive disease Diseases 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 208000030459 obsessive-compulsive personality disease Diseases 0.000 claims 2
- 208000019906 panic disease Diseases 0.000 claims 2
- 208000022821 personality disease Diseases 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 125000004001 thioalkyl group Chemical group 0.000 claims 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 1
- 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 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 1
- SHNAMJKBPSVVIS-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)sulfonyl-3-(1,4-diazepan-1-ylmethyl)indole Chemical compound BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(CN2CCNCCC2)=C1 SHNAMJKBPSVVIS-UHFFFAOYSA-N 0.000 claims 1
- ZXHYBZYREQQHBQ-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]-5-nitroindole Chemical compound BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C([N+]([O-])=O)C=C2C(CN2CCN(C)CC2)=C1 ZXHYBZYREQQHBQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- JCBJMRJGUSQZOZ-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)sulfonyl-3-[(4-pyridin-2-ylpiperazin-1-yl)methyl]indole Chemical compound BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(CN2CCN(CC2)C=2N=CC=CC=2)=C1 JCBJMRJGUSQZOZ-UHFFFAOYSA-N 0.000 claims 1
- NNKGUYIRAAUQQI-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)sulfonyl-3-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]indole Chemical compound BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(CN2CCN(CC2)C=2C(=CC=CC=2)OC)=C1 NNKGUYIRAAUQQI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- SAXXHHORUWVWGD-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)sulfonyl-5-chloro-2-methyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Cl)C=C2C(CN2CCN(C)CC2)=C1C SAXXHHORUWVWGD-UHFFFAOYSA-N 0.000 claims 1
- ODNZUMAZIDCWJW-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)sulfonyl-5-methoxy-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(OC)C=C2C(CN2CCN(C)CC2)=C1 ODNZUMAZIDCWJW-UHFFFAOYSA-N 0.000 claims 1
- IEJPEGHXAWGYSQ-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)sulfonyl-5-methoxy-3-[(4-methylpiperazin-1-yl)methyl]indole;hydrochloride Chemical compound Cl.BrC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(OC)C=C2C(CN2CCN(C)CC2)=C1 IEJPEGHXAWGYSQ-UHFFFAOYSA-N 0.000 claims 1
- PLLVYYHPNFOESC-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]-5-nitroindole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C(=CC=CC=2)Br)C2=CC=C([N+]([O-])=O)C=C12 PLLVYYHPNFOESC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- UZMFWGANGMYRJI-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole-5-carbonitrile Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C(=CC=CC=2)Br)C2=CC=C(C#N)C=C12 UZMFWGANGMYRJI-UHFFFAOYSA-N 0.000 claims 1
- HZFPOIDKRPOAAB-UHFFFAOYSA-N 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=CC=C12 HZFPOIDKRPOAAB-UHFFFAOYSA-N 0.000 claims 1
- NUFLGFRYXRHUDF-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-3-[(4-pyridin-2-ylpiperazin-1-yl)methyl]indole Chemical compound BrC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(CN2CCN(CC2)C=2N=CC=CC=2)=C1 NUFLGFRYXRHUDF-UHFFFAOYSA-N 0.000 claims 1
- CORLFTYYGFCCMV-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-3-[[4-(3-chlorophenyl)piperazin-1-yl]methyl]indole Chemical compound ClC1=CC=CC(N2CCN(CC=3C4=CC=CC=C4N(C=3)S(=O)(=O)C=3C(=CC=CC=3)Br)CC2)=C1 CORLFTYYGFCCMV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- DKFJMSXDIDGXEM-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]-5-nitroindole Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(Br)=CC=2)C2=CC=C([N+]([O-])=O)C=C12 DKFJMSXDIDGXEM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ZYUBETKYUVIEIY-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole-5-carbonitrile Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(Br)=CC=2)C2=CC=C(C#N)C=C12 ZYUBETKYUVIEIY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- IILSVLGJNBXFHD-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-5-chloro-2-methyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1CN(C)CCN1CC1=C(C)N(S(=O)(=O)C=2C=CC(Br)=CC=2)C2=CC=C(Cl)C=C12 IILSVLGJNBXFHD-UHFFFAOYSA-N 0.000 claims 1
- GLFWREZYZAEHQC-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-5-chloro-3-[(4-methylpiperazin-1-yl)methyl]-2-phenylindole Chemical compound C1CN(C)CCN1CC(C1=CC(Cl)=CC=C1N1S(=O)(=O)C=2C=CC(Br)=CC=2)=C1C1=CC=CC=C1 GLFWREZYZAEHQC-UHFFFAOYSA-N 0.000 claims 1
- COKPBQBGLKTUQP-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-5-methoxy-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(Br)=CC=2)C=C1CN1CCN(C)CC1 COKPBQBGLKTUQP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- YDRLSTVVRBLOHG-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole-5-carbonitrile Chemical compound C1CN(C)CCN1CC1=CN(S(=O)(=O)C=2C=CC(F)=CC=2)C2=CC=C(C#N)C=C12 YDRLSTVVRBLOHG-UHFFFAOYSA-N 0.000 claims 1
- MBDBSGITWCTYBM-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-3-[(4-pyridin-2-ylpiperazin-1-yl)methyl]indole Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(CN2CCN(CC2)C=2N=CC=CC=2)=C1 MBDBSGITWCTYBM-UHFFFAOYSA-N 0.000 claims 1
- PIQRFUCZSGOHKB-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-5-methoxy-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(F)=CC=2)C=C1CN1CCN(C)CC1 PIQRFUCZSGOHKB-UHFFFAOYSA-N 0.000 claims 1
- JQSOUZQNWRSGCT-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-5-methoxy-3-[(4-pyridin-2-ylpiperazin-1-yl)methyl]indole Chemical compound C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(F)=CC=2)C=C1CN(CC1)CCN1C1=CC=CC=N1 JQSOUZQNWRSGCT-UHFFFAOYSA-N 0.000 claims 1
- IIDFNRRTWIENTJ-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-5-methoxy-3-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]indole Chemical compound C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(F)=CC=2)C=C1CN(CC1)CCN1C1=CC=CC=C1OC IIDFNRRTWIENTJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- AVIQOMXISMYLAD-QGZVFWFLSA-N 1-(4-methoxyphenyl)sulfonyl-3-[(1r)-1-(4-methylpiperazin-1-yl)ethyl]indole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C([C@@H](C)N2CCN(C)CC2)=C1 AVIQOMXISMYLAD-QGZVFWFLSA-N 0.000 claims 1
- AVIQOMXISMYLAD-KRWDZBQOSA-N 1-(4-methoxyphenyl)sulfonyl-3-[(1s)-1-(4-methylpiperazin-1-yl)ethyl]indole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C([C@H](C)N2CCN(C)CC2)=C1 AVIQOMXISMYLAD-KRWDZBQOSA-N 0.000 claims 1
- 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 1
- XKGGZLWYPXYHEE-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-3-[(4-methylpiperazin-1-yl)methyl]indole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(CN2CCN(C)CC2)=C1 XKGGZLWYPXYHEE-UHFFFAOYSA-N 0.000 claims 1
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| WO2005005439A1 (en) * | 2003-07-09 | 2005-01-20 | Suven Life Sciences Limited | Benzothiazino indoles |
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| RU2422442C2 (ru) | 2005-07-29 | 2011-06-27 | Ф. Хоффманн-Ля Рош Аг | Производные индол-3-ил-карбонил-пиперидина и пиперазина |
| CA2618636C (en) | 2005-08-12 | 2011-01-18 | Suven Life Sciences Limited | Aminoaryl sulphonamide derivatives as functional 5-ht6 ligands |
| WO2007020653A1 (en) * | 2005-08-12 | 2007-02-22 | Suven Life Sciences Limited | Thioether derivatives as functional 5-ht6 ligands |
| KR101250820B1 (ko) | 2005-08-16 | 2013-04-04 | 수벤 라이프 사이언시스 리미티드 | 개선된 로사르탄 제조 방법 |
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| JP2010515674A (ja) * | 2007-01-08 | 2010-05-13 | スベン ライフ サイエンシズ リミティド | ５−（ヘテロシクリル）アルキル−ｎ−（アリールスルホニル）インドール化合物および５−ｈｔ６リガンドとしてのそれらの使用 |
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| WO2008144263A1 (en) * | 2007-05-18 | 2008-11-27 | The Ohio State University Research Foundation | Potent indole-3-carbinol-derived antitumor agents |
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| ES2424036T3 (es) | 2008-09-17 | 2013-09-26 | Suven Life Sciences Limited | Compuestos de amina de arilsulfonamida y su uso como ligandos de 5-HT6 |
| US8912220B2 (en) * | 2009-08-10 | 2014-12-16 | Galenea Pharmaceuticals | Compounds and methods of use thereof |
| US8153680B2 (en) * | 2009-08-25 | 2012-04-10 | The Ohio State University Research Foundation | Alkyl indole-3-carbinol-derived antitumor agents |
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| 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 |
| CA2905242C (en) | 2013-03-15 | 2016-11-29 | Pfizer Inc. | Indole 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 |
| WO2015083179A1 (en) * | 2013-12-02 | 2015-06-11 | 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 |
| EP3083588B1 (en) | 2013-12-20 | 2020-12-09 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic compounds and their application in pharmaceuticals |
| EP3166924B1 (en) | 2014-07-08 | 2019-02-20 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic derivatives and pharmaceutical applications thereof |
| BR112017002921B1 (pt) | 2014-08-16 | 2023-03-28 | Suven Life Sciences Limited | Composto metabólito ativo de monohidrato dimesilato de 1-[(2- bromofenil)sulfonil]-5-metoxi-3-[(4-metil-1-piperazinil)metil]-1h-indola,processo para a preparação do composto e composição farmacêutica |
| DK3458039T3 (da) * | 2016-05-18 | 2020-09-14 | Suven Life Sciences Ltd | Tripelkombination af rene 5-ht6-receptorantagonister, acetylcholinesterasehæmmere og nmda-receptorantagonist |
| DK3458040T3 (da) * | 2016-05-18 | 2021-05-03 | Suven Life Sciences Ltd | Kombination af rene 5-ht6-receptorantagonister med nmda-receptorantagonist |
| CA3023819C (en) * | 2016-05-18 | 2019-10-22 | Suven Life Sciences Limited | Combination of pure 5-ht6 receptor antagonists with acetylcholinesterase inhibitors |
| HRP20211092T1 (hr) * | 2016-10-03 | 2021-10-15 | Suven Life Sciences Limited | Farmaceutske kompozicije antagonista 5-ht6 |
| CN107174586B (zh) * | 2017-02-21 | 2020-08-11 | 中国科学院昆明植物研究所 | 以芦竹碱衍生物为活性成分的药物组合物及其应用 |
| JP6959371B2 (ja) * | 2017-07-03 | 2021-11-02 | スヴェン・ライフ・サイエンシーズ・リミテッドＳｕｖｅｎ Ｌｉｆｅ Ｓｃｉｅｎｃｅｓ Ｌｉｍｉｔｅｄ | 純粋な５−ｈｔ６受容体アンタゴニストの新たな使用 |
| BR112022010540A2 (pt) | 2019-12-02 | 2022-08-16 | Suven Life Sciences Ltd | Métodos para tratar sintomas comportamentais e psicológicos em pacientes com demência |
| WO2021111330A1 (en) | 2019-12-02 | 2021-06-10 | Suven Life Sciences Limited | Treating behavioral and psychological symptoms in dementia patients |
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| CN111362858B (zh) * | 2020-03-16 | 2021-05-11 | 东莞市东阳光新药研发有限公司 | 芳杂环类衍生物的盐及其用途 |
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| CN115504925B (zh) * | 2021-06-22 | 2024-03-12 | 广东药科大学 | 一类ppar激动剂、其制备方法及其作为药物的用途 |
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| GB8719167D0 (en) | 1987-08-13 | 1987-09-23 | Glaxo Group Ltd | Chemical compounds |
| GB8724912D0 (en) | 1987-10-23 | 1987-11-25 | Wellcome Found | Indole derivatives |
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| JPH04208263A (ja) * | 1990-01-02 | 1992-07-29 | Fujisawa Pharmaceut Co Ltd | インドール誘導体およびそれらの製造法 |
| IL96891A0 (en) | 1990-01-17 | 1992-03-29 | Merck Sharp & Dohme | Indole-substituted five-membered heteroaromatic compounds,their preparation and pharmaceutical compositions containing them |
| CA2042295A1 (fr) | 1990-05-15 | 1991-11-16 | Jacques Chauveau | Derives de mediateurs endogenes, leurs sels, procede de preparation, applications, et compositions les renfermant |
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| TW263508B (enExample) * | 1991-02-12 | 1995-11-21 | Pfizer | |
| GB9113802D0 (en) | 1991-06-26 | 1991-08-14 | Smithkline Beecham Plc | Medicaments |
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| GB9210400D0 (en) | 1992-05-15 | 1992-07-01 | Merck Sharp & Dohme | Therapeutic agents |
| KR940007001A (ko) | 1992-09-16 | 1994-04-26 | 최승주 | 새로운 n-신나모일-2-메틸-5-메톡시-3-인돌 아세트산 에스테르, 그 제조방법 및 이를 함유하는 약학적 제제 |
| CA2194984C (en) * | 1994-07-26 | 2002-07-02 | John Eugene Macor | 4-indole derivatives as serotonin agonists and antagonists |
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| CN1317276C (zh) | 2000-09-29 | 2007-05-23 | 中国科学院上海药物研究所 | 一类吲哚基哌啶类化合物及其制备方法和用途 |
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| WO2002041889A2 (en) * | 2000-11-24 | 2002-05-30 | Smithkline Beecham P.L.C. | Indolsulfonyl compounds useful in the treatment of cns disorders |
| AU2002226048A1 (en) * | 2000-12-11 | 2002-06-24 | Smith Kline Beecham Corporation | Urotensin-ii receptor antagonists |
| ATE327232T1 (de) * | 2000-12-22 | 2006-06-15 | Wyeth Corp | Heterozyklylalkylindole oder -azaindole als 5- hydroxytryptamine-6 liganden |
| JP2004524295A (ja) * | 2001-01-26 | 2004-08-12 | スミスクライン・ビーチャム・コーポレイション | ウロテンシン−ｉｉ受容体アンタゴニスト |
| JP4694129B2 (ja) * | 2002-02-12 | 2011-06-08 | ナームローゼ・フエンノートチヤツプ・オルガノン | 中枢神経系疾患の治療において有用な１−アリールスルホニル−３−置換インドール及びインドリン誘導体 |
-
2003
- 2003-06-05 BR BRPI0318799A patent/BRPI0318799B8/pt active IP Right Grant
- 2003-06-05 CN CN200910134498XA patent/CN101544592B/zh not_active Expired - Lifetime
- 2003-06-05 AU AU2003237599A patent/AU2003237599B2/en not_active Expired
- 2003-06-05 US US10/536,618 patent/US7875605B2/en active Active
- 2003-06-05 BR BRPI0315959A patent/BRPI0315959C1/pt not_active IP Right Cessation
- 2003-06-05 SI SI200331342T patent/SI1581492T1/sl unknown
- 2003-06-05 NZ NZ540840A patent/NZ540840A/en not_active IP Right Cessation
- 2003-06-05 PT PT03735970T patent/PT1581492E/pt unknown
- 2003-06-05 CN CN038254883A patent/CN1720225B/zh not_active Expired - Lifetime
- 2003-06-05 EP EP03735970A patent/EP1581492B1/en not_active Expired - Lifetime
- 2003-06-05 MX MXPA05005701A patent/MXPA05005701A/es active IP Right Grant
- 2003-06-05 ES ES03735970T patent/ES2310243T3/es not_active Expired - Lifetime
- 2003-06-05 JP JP2004554900A patent/JP4559230B2/ja not_active Expired - Lifetime
- 2003-06-05 EA EA200500881A patent/EA011320B1/ru unknown
- 2003-06-05 NZ NZ572186A patent/NZ572186A/en not_active IP Right Cessation
- 2003-06-05 CA CA2509982A patent/CA2509982C/en not_active Expired - Lifetime
- 2003-06-05 DK DK03735970T patent/DK1581492T3/da active
- 2003-06-05 AT AT03735970T patent/ATE401307T1/de active
- 2003-06-05 DE DE60322266T patent/DE60322266D1/de not_active Expired - Lifetime
- 2003-06-05 KR KR1020057009512A patent/KR100818508B1/ko not_active Expired - Lifetime
- 2003-06-05 WO PCT/IN2003/000209 patent/WO2004048330A1/en not_active Ceased
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2005
- 2005-05-19 ZA ZA200504043A patent/ZA200504043B/en unknown
- 2005-06-08 NO NO20052737A patent/NO330341B1/no not_active IP Right Cessation
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2008
- 2008-09-17 CY CY20081100999T patent/CY1108786T1/el unknown
- 2008-12-05 NO NO20085054A patent/NO335015B1/no not_active IP Right Cessation
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