JP2010519226A5 - - Google Patents
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- Publication number
- JP2010519226A5 JP2010519226A5 JP2009550174A JP2009550174A JP2010519226A5 JP 2010519226 A5 JP2010519226 A5 JP 2010519226A5 JP 2009550174 A JP2009550174 A JP 2009550174A JP 2009550174 A JP2009550174 A JP 2009550174A JP 2010519226 A5 JP2010519226 A5 JP 2010519226A5
- Authority
- JP
- Japan
- Prior art keywords
- sulfonyl
- piperazin
- indole
- methyl
- indazole
- 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.)
- Pending
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- -1 cyano, hydroxy Chemical group 0.000 claims 37
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 20
- 125000004432 carbon atom Chemical group C* 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 229920006395 saturated elastomer Polymers 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000006413 ring segment Chemical group 0.000 claims 8
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 7
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 125000004434 sulfur atom Chemical group 0.000 claims 4
- RQVGCOGAINMQJO-UHFFFAOYSA-N 6-piperazin-1-yl-1-pyridin-3-ylsulfonylindole Chemical compound C1=CC2=CC=C(N3CCNCC3)C=C2N1S(=O)(=O)C1=CC=CN=C1 RQVGCOGAINMQJO-UHFFFAOYSA-N 0.000 claims 3
- 206010010774 Constipation Diseases 0.000 claims 3
- 208000015114 central nervous system disease Diseases 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 230000002496 gastric effect Effects 0.000 claims 3
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- YCNURPYTJNOQOS-UHFFFAOYSA-N 7-(3-ethyl-6-piperazin-1-ylindazol-1-yl)sulfonyl-4-methyl-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2C(CC)=NN(S(=O)(=O)C=3C=C4OCCN(C)C4=CC=3)C2=CC=1N1CCNCC1 YCNURPYTJNOQOS-UHFFFAOYSA-N 0.000 claims 2
- OHPUUSZZEPAKHA-UHFFFAOYSA-N 7-(6-piperazin-1-ylindol-1-yl)sulfonyl-4h-1,4-benzoxazin-3-one Chemical compound C=1C=C2NC(=O)COC2=CC=1S(=O)(=O)N(C1=C2)C=CC1=CC=C2N1CCNCC1 OHPUUSZZEPAKHA-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 206010019196 Head injury Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- ADTDIWLBMBAJKV-NRFANRHFSA-N (3s)-1-[3-(3-ethyl-6-piperazin-1-ylindol-1-yl)sulfonylphenyl]pyrrolidin-3-ol Chemical compound C=1C=C2C(CC)=CN(S(=O)(=O)C=3C=C(C=CC=3)N3C[C@@H](O)CC3)C2=CC=1N1CCNCC1 ADTDIWLBMBAJKV-NRFANRHFSA-N 0.000 claims 1
- XDIKYVLQQLRUDU-UHFFFAOYSA-N 1-(1-benzofuran-5-ylsulfonyl)-6-(1,4-diazepan-1-yl)indazole Chemical compound C=1C=C2OC=CC2=CC=1S(=O)(=O)N(C1=C2)N=CC1=CC=C2N1CCCNCC1 XDIKYVLQQLRUDU-UHFFFAOYSA-N 0.000 claims 1
- KZJWMGFSZLEGNM-UHFFFAOYSA-N 1-(1-benzofuran-5-ylsulfonyl)-6-(4-methyl-1,4-diazepan-1-yl)indazole Chemical compound C1CN(C)CCCN1C1=CC=C(C=NN2S(=O)(=O)C=3C=C4C=COC4=CC=3)C2=C1 KZJWMGFSZLEGNM-UHFFFAOYSA-N 0.000 claims 1
- PBSVMXJGADSKDH-UHFFFAOYSA-N 1-(1-benzofuran-5-ylsulfonyl)-6-(4-methylpiperazin-1-yl)pyrrolo[2,3-b]pyridine Chemical compound C1CN(C)CCN1C1=CC=C(C=CN2S(=O)(=O)C=3C=C4C=COC4=CC=3)C2=N1 PBSVMXJGADSKDH-UHFFFAOYSA-N 0.000 claims 1
- LOGONEOVTHBFMB-UHFFFAOYSA-N 1-(1-benzofuran-6-ylsulfonyl)-6-(1,4-diazepan-1-yl)indazole Chemical compound C=1C=C2C=COC2=CC=1S(=O)(=O)N(C1=C2)N=CC1=CC=C2N1CCCNCC1 LOGONEOVTHBFMB-UHFFFAOYSA-N 0.000 claims 1
- LFSVOCVEMTYMDO-UHFFFAOYSA-N 1-(1-benzofuran-6-ylsulfonyl)-6-(1,4-diazepan-1-yl)indole Chemical compound C=1C=C2C=COC2=CC=1S(=O)(=O)N(C1=C2)C=CC1=CC=C2N1CCCNCC1 LFSVOCVEMTYMDO-UHFFFAOYSA-N 0.000 claims 1
- NZPJMYLBBHIJIT-UHFFFAOYSA-N 1-(1-benzofuran-6-ylsulfonyl)-6-(4-methyl-1,4-diazepan-1-yl)indazole Chemical compound C1CN(C)CCCN1C1=CC=C(C=NN2S(=O)(=O)C=3C=C4OC=CC4=CC=3)C2=C1 NZPJMYLBBHIJIT-UHFFFAOYSA-N 0.000 claims 1
- JCEBDUAQPWSJIB-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-6-ylsulfonyl)-6-piperazin-1-ylindazole Chemical compound C=1C=C2OCCOC2=CC=1S(=O)(=O)N(C1=C2)N=CC1=CC=C2N1CCNCC1 JCEBDUAQPWSJIB-UHFFFAOYSA-N 0.000 claims 1
- UIHORGBXMUBBTH-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-6-ylsulfonyl)-6-piperazin-1-ylindole Chemical compound C=1C=C2OCCOC2=CC=1S(=O)(=O)N(C1=C2)C=CC1=CC=C2N1CCNCC1 UIHORGBXMUBBTH-UHFFFAOYSA-N 0.000 claims 1
- TXSYYVSCELWWGU-UHFFFAOYSA-N 1-(2,4-difluorophenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound FC1=CC(F)=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=N1 TXSYYVSCELWWGU-UHFFFAOYSA-N 0.000 claims 1
- JSUXIDAHSGHRSP-UHFFFAOYSA-N 1-(2,4-difluorophenyl)sulfonyl-6-piperazin-1-ylindole Chemical compound FC1=CC(F)=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=C1 JSUXIDAHSGHRSP-UHFFFAOYSA-N 0.000 claims 1
- DWJJIOBNTJEODI-UHFFFAOYSA-N 1-(2,5-difluorophenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound FC1=CC=C(F)C(S(=O)(=O)N2C3=CC(=CC=C3C=N2)N2CCNCC2)=C1 DWJJIOBNTJEODI-UHFFFAOYSA-N 0.000 claims 1
- YORNGFATOLBRRJ-UHFFFAOYSA-N 1-(2,5-difluorophenyl)sulfonyl-6-piperazin-1-ylindole Chemical compound FC1=CC=C(F)C(S(=O)(=O)N2C3=CC(=CC=C3C=C2)N2CCNCC2)=C1 YORNGFATOLBRRJ-UHFFFAOYSA-N 0.000 claims 1
- UPXIKUHHXPWQCA-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound COC1=CC=C(OC)C(S(=O)(=O)N2C3=CC(=CC=C3C=N2)N2CCNCC2)=C1 UPXIKUHHXPWQCA-UHFFFAOYSA-N 0.000 claims 1
- OGSXIODMEFHLRL-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)sulfonyl-6-piperazin-1-ylindole Chemical compound COC1=CC=C(OC)C(S(=O)(=O)N2C3=CC(=CC=C3C=C2)N2CCNCC2)=C1 OGSXIODMEFHLRL-UHFFFAOYSA-N 0.000 claims 1
- PVSOOIKNRXXNPI-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound ClC1=CC=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=N1 PVSOOIKNRXXNPI-UHFFFAOYSA-N 0.000 claims 1
- BHCYSPJSGWDOOV-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-6-piperazin-1-ylindole Chemical compound ClC1=CC=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=C1 BHCYSPJSGWDOOV-UHFFFAOYSA-N 0.000 claims 1
- MZCPCTDCNNJWCC-UHFFFAOYSA-N 1-(2-fluorophenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound FC1=CC=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=N1 MZCPCTDCNNJWCC-UHFFFAOYSA-N 0.000 claims 1
- ABOPQOOKESSZDQ-UHFFFAOYSA-N 1-(2-fluorophenyl)sulfonyl-6-piperazin-1-ylindole Chemical compound FC1=CC=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=C1 ABOPQOOKESSZDQ-UHFFFAOYSA-N 0.000 claims 1
- JHYJNNNTOHMKGI-UHFFFAOYSA-N 1-(2-methoxyphenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound COC1=CC=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=N1 JHYJNNNTOHMKGI-UHFFFAOYSA-N 0.000 claims 1
- UUZSYDKDHCABIQ-UHFFFAOYSA-N 1-(2-methoxyphenyl)sulfonyl-6-piperazin-1-ylindole Chemical compound COC1=CC=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=C1 UUZSYDKDHCABIQ-UHFFFAOYSA-N 0.000 claims 1
- WXDDYANVEPWXPK-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=N1 WXDDYANVEPWXPK-UHFFFAOYSA-N 0.000 claims 1
- NILMYVRUBSALSA-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)sulfonyl-6-piperazin-1-ylindole Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=C1 NILMYVRUBSALSA-UHFFFAOYSA-N 0.000 claims 1
- RHUWJQJIWGRZSB-UHFFFAOYSA-N 1-(3-chlorophenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound ClC1=CC=CC(S(=O)(=O)N2C3=CC(=CC=C3C=N2)N2CCNCC2)=C1 RHUWJQJIWGRZSB-UHFFFAOYSA-N 0.000 claims 1
- IGMPPSBLAYJPSR-UHFFFAOYSA-N 1-(3-chlorophenyl)sulfonyl-6-piperazin-1-ylindole Chemical compound ClC1=CC=CC(S(=O)(=O)N2C3=CC(=CC=C3C=C2)N2CCNCC2)=C1 IGMPPSBLAYJPSR-UHFFFAOYSA-N 0.000 claims 1
- JZXRJJCQCVSTPP-UHFFFAOYSA-N 1-(3-fluorophenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound FC1=CC=CC(S(=O)(=O)N2C3=CC(=CC=C3C=N2)N2CCNCC2)=C1 JZXRJJCQCVSTPP-UHFFFAOYSA-N 0.000 claims 1
- BHQAIVKFNDVAPK-UHFFFAOYSA-N 1-(3-fluorophenyl)sulfonyl-6-piperazin-1-ylindole Chemical compound FC1=CC=CC(S(=O)(=O)N2C3=CC(=CC=C3C=C2)N2CCNCC2)=C1 BHQAIVKFNDVAPK-UHFFFAOYSA-N 0.000 claims 1
- ALYLEASIAJLDBX-UHFFFAOYSA-N 1-(3-methoxyphenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound COC1=CC=CC(S(=O)(=O)N2C3=CC(=CC=C3C=N2)N2CCNCC2)=C1 ALYLEASIAJLDBX-UHFFFAOYSA-N 0.000 claims 1
- JAIIGEQOPCQWAG-UHFFFAOYSA-N 1-(3-methoxyphenyl)sulfonyl-6-piperazin-1-ylindole Chemical compound COC1=CC=CC(S(=O)(=O)N2C3=CC(=CC=C3C=C2)N2CCNCC2)=C1 JAIIGEQOPCQWAG-UHFFFAOYSA-N 0.000 claims 1
- RZVXKPIPNJZLHT-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=N1 RZVXKPIPNJZLHT-UHFFFAOYSA-N 0.000 claims 1
- OPBLPJLFVJLIOK-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-ethyl-6-piperazin-1-ylindazole Chemical compound C=1C=C2C(CC)=NN(S(=O)(=O)C=3C=CC=CC=3)C2=CC=1N1CCNCC1 OPBLPJLFVJLIOK-UHFFFAOYSA-N 0.000 claims 1
- LWTJQRDPEPNEGQ-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-(4-methylpiperazin-1-yl)indazole-3-carboxylic acid Chemical compound C1CN(C)CCN1C1=CC=C(C(=NN2S(=O)(=O)C=3C=CC=CC=3)C(O)=O)C2=C1 LWTJQRDPEPNEGQ-UHFFFAOYSA-N 0.000 claims 1
- ZZRPBEZGINGVMX-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-(4-methylpiperazin-1-yl)indole Chemical compound C1CN(C)CCN1C1=CC=C(C=CN2S(=O)(=O)C=3C=CC=CC=3)C2=C1 ZZRPBEZGINGVMX-UHFFFAOYSA-N 0.000 claims 1
- RTGJTPRVJSBLFD-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-piperazin-1-ylindole Chemical compound C1=CC2=CC=C(N3CCNCC3)C=C2N1S(=O)(=O)C1=CC=CC=C1 RTGJTPRVJSBLFD-UHFFFAOYSA-N 0.000 claims 1
- KQBDABKQHCVIOK-UHFFFAOYSA-N 1-[3-(3-ethyl-6-piperazin-1-ylindazol-1-yl)sulfonylphenyl]pyrrolidin-3-ol Chemical compound C=1C=C2C(CC)=NN(S(=O)(=O)C=3C=C(C=CC=3)N3CC(O)CC3)C2=CC=1N1CCNCC1 KQBDABKQHCVIOK-UHFFFAOYSA-N 0.000 claims 1
- YUYWZLUDWVMIKW-UHFFFAOYSA-N 1-[3-(3-methoxypyrrolidin-1-yl)phenyl]sulfonyl-6-(4-methyl-1,4-diazepan-1-yl)indazole Chemical compound C1C(OC)CCN1C1=CC=CC(S(=O)(=O)N2C3=CC(=CC=C3C=N2)N2CCN(C)CCC2)=C1 YUYWZLUDWVMIKW-UHFFFAOYSA-N 0.000 claims 1
- YWNMMMWJURYOPU-UHFFFAOYSA-N 1-[3-(3-methoxypyrrolidin-1-yl)phenyl]sulfonyl-6-(4-methyl-1,4-diazepan-1-yl)indole Chemical compound C1C(OC)CCN1C1=CC=CC(S(=O)(=O)N2C3=CC(=CC=C3C=C2)N2CCN(C)CCC2)=C1 YWNMMMWJURYOPU-UHFFFAOYSA-N 0.000 claims 1
- JPJKFVCJTBXCSV-UHFFFAOYSA-N 1-[3-(3-methoxypyrrolidin-1-yl)phenyl]sulfonyl-6-(4-methylpiperazin-1-yl)indazole Chemical compound C1C(OC)CCN1C1=CC=CC(S(=O)(=O)N2C3=CC(=CC=C3C=N2)N2CCN(C)CC2)=C1 JPJKFVCJTBXCSV-UHFFFAOYSA-N 0.000 claims 1
- LBIQENJTASNXQV-UHFFFAOYSA-N 1-[3-(3-methoxypyrrolidin-1-yl)phenyl]sulfonyl-6-(4-methylpiperazin-1-yl)indole Chemical compound C1C(OC)CCN1C1=CC=CC(S(=O)(=O)N2C3=CC(=CC=C3C=C2)N2CCN(C)CC2)=C1 LBIQENJTASNXQV-UHFFFAOYSA-N 0.000 claims 1
- IIACDKWDBOSBHI-UHFFFAOYSA-N 1-[3-(3-methoxypyrrolidin-1-yl)phenyl]sulfonyl-6-(4-methylpiperazin-1-yl)pyrrolo[2,3-b]pyridine Chemical compound C1C(OC)CCN1C1=CC=CC(S(=O)(=O)N2C3=NC(=CC=C3C=C2)N2CCN(C)CC2)=C1 IIACDKWDBOSBHI-UHFFFAOYSA-N 0.000 claims 1
- NIKGJIHOYXJKKP-UHFFFAOYSA-N 1-[3-(3-methoxypyrrolidin-1-yl)phenyl]sulfonyl-6-piperazin-1-ylindole Chemical compound C1C(OC)CCN1C1=CC=CC(S(=O)(=O)N2C3=CC(=CC=C3C=C2)N2CCNCC2)=C1 NIKGJIHOYXJKKP-UHFFFAOYSA-N 0.000 claims 1
- PMFOAOBYVVLKED-FQEVSTJZSA-N 1-[3-[(3s)-3-methoxypyrrolidin-1-yl]phenyl]sulfonyl-3-methyl-6-piperazin-1-ylindazole Chemical compound C1[C@@H](OC)CCN1C1=CC=CC(S(=O)(=O)N2C3=CC(=CC=C3C(C)=N2)N2CCNCC2)=C1 PMFOAOBYVVLKED-FQEVSTJZSA-N 0.000 claims 1
- SNPGIQRSFYALIF-NRFANRHFSA-N 1-[3-[(3s)-3-methoxypyrrolidin-1-yl]phenyl]sulfonyl-3-methyl-6-piperazin-1-ylindole Chemical compound C1[C@@H](OC)CCN1C1=CC=CC(S(=O)(=O)N2C3=CC(=CC=C3C(C)=C2)N2CCNCC2)=C1 SNPGIQRSFYALIF-NRFANRHFSA-N 0.000 claims 1
- OGDHHBWNUBKISC-UHFFFAOYSA-N 1-[3-[3-ethyl-6-(4-methylpiperazin-1-yl)indazol-1-yl]sulfonylphenyl]pyrrolidin-3-ol Chemical compound C=1C=C2C(CC)=NN(S(=O)(=O)C=3C=C(C=CC=3)N3CC(O)CC3)C2=CC=1N1CCN(C)CC1 OGDHHBWNUBKISC-UHFFFAOYSA-N 0.000 claims 1
- TTYFOZJVVOCZPF-UHFFFAOYSA-N 1-[5-(3-ethyl-6-piperazin-1-ylindazol-1-yl)sulfonyl-2,3-dihydroindol-1-yl]ethanone Chemical compound C=1C=C2C(CC)=NN(S(=O)(=O)C=3C=C4CCN(C4=CC=3)C(C)=O)C2=CC=1N1CCNCC1 TTYFOZJVVOCZPF-UHFFFAOYSA-N 0.000 claims 1
- FPEVBJQZBQEUGQ-UHFFFAOYSA-N 1-[5-(6-piperazin-1-ylindol-1-yl)sulfonyl-2,3-dihydroindol-1-yl]ethanone Chemical compound C=1C=C2N(C(=O)C)CCC2=CC=1S(=O)(=O)N(C1=C2)C=CC1=CC=C2N1CCNCC1 FPEVBJQZBQEUGQ-UHFFFAOYSA-N 0.000 claims 1
- QOGSBGQZNBPMMR-UHFFFAOYSA-N 1-[5-[6-(1,4-diazepan-1-yl)indazol-1-yl]sulfonyl-2,3-dihydroindol-1-yl]ethanone Chemical compound C=1C=C2N(C(=O)C)CCC2=CC=1S(=O)(=O)N(C1=C2)N=CC1=CC=C2N1CCCNCC1 QOGSBGQZNBPMMR-UHFFFAOYSA-N 0.000 claims 1
- QSBBSFIHUJRJPJ-UHFFFAOYSA-N 1-[5-[6-(1,4-diazepan-1-yl)indol-1-yl]sulfonyl-2,3-dihydroindol-1-yl]ethanone Chemical compound C=1C=C2N(C(=O)C)CCC2=CC=1S(=O)(=O)N(C1=C2)C=CC1=CC=C2N1CCCNCC1 QSBBSFIHUJRJPJ-UHFFFAOYSA-N 0.000 claims 1
- TZIHAMMSUVQTHM-UHFFFAOYSA-N 1-[5-[6-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)indol-1-yl]sulfonyl-2,3-dihydroindol-1-yl]ethanone Chemical compound C1CN2CCCC2CN1C(C=C12)=CC=C2C=CN1S(=O)(=O)C1=CC=C2N(C(=O)C)CCC2=C1 TZIHAMMSUVQTHM-UHFFFAOYSA-N 0.000 claims 1
- IFGMBCIJORJSHN-UHFFFAOYSA-N 1-[5-[6-(4-methyl-1,4-diazepan-1-yl)indol-1-yl]sulfonyl-2,3-dihydroindol-1-yl]ethanone Chemical compound C1CN(C)CCCN1C1=CC=C(C=CN2S(=O)(=O)C=3C=C4CCN(C4=CC=3)C(C)=O)C2=C1 IFGMBCIJORJSHN-UHFFFAOYSA-N 0.000 claims 1
- DZPGWWPFCLDAQA-UHFFFAOYSA-N 1-[5-[6-(4-methylpiperazin-1-yl)indazol-1-yl]sulfonyl-2,3-dihydroindol-1-yl]ethanone Chemical compound C1CN(C)CCN1C1=CC=C(C=NN2S(=O)(=O)C=3C=C4CCN(C4=CC=3)C(C)=O)C2=C1 DZPGWWPFCLDAQA-UHFFFAOYSA-N 0.000 claims 1
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| Country | Link |
|---|---|
| US (1) | US20080200471A1 (https=) |
| EP (1) | EP2121603A2 (https=) |
| JP (1) | JP2010519226A (https=) |
| KR (1) | KR20100014413A (https=) |
| CN (1) | CN101641329A (https=) |
| AU (1) | AU2008216032A1 (https=) |
| BR (1) | BRPI0807602A2 (https=) |
| CA (1) | CA2674087A1 (https=) |
| MX (1) | MX2009008324A (https=) |
| WO (1) | WO2008101247A2 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8318725B2 (en) | 2008-09-17 | 2012-11-27 | Suven Life Sciences Limited | Aryl indolyl sulfonamide compounds and their use as 5-HT6 ligands |
| JO3250B1 (ar) | 2009-09-22 | 2018-09-16 | Novartis Ag | إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7 |
| FR2955110A1 (fr) | 2010-01-08 | 2011-07-15 | Fournier Lab Sa | Nouveaux derives de type pyrrolopyridine benzoique |
| FR2955108B1 (fr) | 2010-01-08 | 2012-03-16 | Fournier Lab Sa | Utilisation de derives de pyrrolopyridine comme activateurs de nurr-1, pour le traitement de la maladie de parkinson |
| 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 |
| DK3180001T3 (en) * | 2014-08-16 | 2019-04-01 | Suven Life Sciences Ltd | ACTIVE METABOLITE OF 1 - [(2-BROMPHENYL) SULPHONYL] -5-METHOXY-3 - [(4-METHYL-1-PIPERAZINYL) METHYL] -1H-INDOL-DIMESYLATE-MONOHYDRATE AND DIMESYLATE-DIHYDRATE SALT |
| CN108752342A (zh) * | 2018-08-17 | 2018-11-06 | 西安瑞联新材料股份有限公司 | 1-H-吡啶并[1,2-a]-6-氢吡嗪-1,4-二酮的制备方法 |
| CN110183383A (zh) * | 2019-06-25 | 2019-08-30 | 深圳市格物致欣化学技术有限公司 | 3-醛基-1h-取代吲唑及其制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6100291A (en) * | 1998-03-16 | 2000-08-08 | Allelix Biopharmaceuticals Inc. | Pyrrolidine-indole compounds having 5-HT6 affinity |
| US6133287A (en) * | 1998-03-24 | 2000-10-17 | Allelix Biopharmaceuticals Inc. | Piperidine-indole compounds having 5-HT6 affinity |
| US6251893B1 (en) * | 1998-06-15 | 2001-06-26 | Nps Allelix Corp. | Bicyclic piperidine and piperazine compounds having 5-HT6 receptor affinity |
| US6191141B1 (en) * | 1999-08-12 | 2001-02-20 | Nps Allelix Corp. | Azaindoles having serotonin receptor affinity |
| US6686374B1 (en) * | 1999-08-12 | 2004-02-03 | Nps Allelix Corp. | Azaindoles having serotonin receptor affinity |
| WO2001032660A1 (en) * | 1999-11-05 | 2001-05-10 | Nps Allelix Corp. | Compounds having 5-ht6 receptor antagonist activity |
| US6897215B1 (en) * | 1999-11-05 | 2005-05-24 | Nps Allelix Corp. | Compounds having 5-HT6 receptor antagonist activity |
| US7034029B2 (en) * | 2000-11-02 | 2006-04-25 | Wyeth | 1-aryl- or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6 ligands |
| JP4184077B2 (ja) * | 2000-11-02 | 2008-11-19 | ワイス | ５−ヒドロキシトリプトアミン−６リガンドとしての１−アリールまたは１−アルキルスルホニル−ヘテロシクリルベンザゾール |
| WO2002041889A2 (en) * | 2000-11-24 | 2002-05-30 | Smithkline Beecham P.L.C. | Indolsulfonyl compounds useful in the treatment of cns disorders |
| WO2002051837A2 (en) * | 2000-12-22 | 2002-07-04 | Wyeth | Heterocyclindazole and azaindazole compounds as 5-hydroxytryptamine-6 ligands |
| BR0210929A (pt) * | 2001-06-07 | 2004-06-08 | Hoffmann La Roche | Derivados de indol com afinidade para o receptor 5-ht6 |
| GB0202679D0 (en) * | 2002-02-05 | 2002-03-20 | Glaxo Group Ltd | Novel compounds |
| EP1984351A1 (en) * | 2006-02-17 | 2008-10-29 | Memory Pharmaceuticals Corporation | Compounds having 5-ht6 receptor affinity |
-
2008
- 2008-02-19 AU AU2008216032A patent/AU2008216032A1/en not_active Abandoned
- 2008-02-19 WO PCT/US2008/054309 patent/WO2008101247A2/en not_active Ceased
- 2008-02-19 KR KR1020097019250A patent/KR20100014413A/ko not_active Withdrawn
- 2008-02-19 CN CN200880005213A patent/CN101641329A/zh active Pending
- 2008-02-19 BR BRPI0807602-2A patent/BRPI0807602A2/pt not_active IP Right Cessation
- 2008-02-19 US US12/033,797 patent/US20080200471A1/en not_active Abandoned
- 2008-02-19 JP JP2009550174A patent/JP2010519226A/ja active Pending
- 2008-02-19 EP EP08730168A patent/EP2121603A2/en not_active Withdrawn
- 2008-02-19 CA CA002674087A patent/CA2674087A1/en not_active Abandoned
- 2008-02-19 MX MX2009008324A patent/MX2009008324A/es not_active Application Discontinuation
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