JP2010520917A5 - - Google Patents
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- Publication number
- JP2010520917A5 JP2010520917A5 JP2009553146A JP2009553146A JP2010520917A5 JP 2010520917 A5 JP2010520917 A5 JP 2010520917A5 JP 2009553146 A JP2009553146 A JP 2009553146A JP 2009553146 A JP2009553146 A JP 2009553146A JP 2010520917 A5 JP2010520917 A5 JP 2010520917A5
- Authority
- JP
- Japan
- Prior art keywords
- azepino
- tetrahydro
- indole
- sulfonyl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- -1 imidazolylmethyl Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- GTTLPYDKIIPQQI-UHFFFAOYSA-N 1-(phenylsulfonyl)-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinoline Chemical compound C1=C(C=23)CNCC3=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 GTTLPYDKIIPQQI-UHFFFAOYSA-N 0.000 claims 1
- QOEYGXNMQBQLFB-UHFFFAOYSA-N 1-(phenylsulfonyl)-3,4,5,6-tetrahydro-1h-azepino[5,4,3-cd]indol Chemical compound C1=C(C=23)CCNCC3=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 QOEYGXNMQBQLFB-UHFFFAOYSA-N 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- MXOQUXZPZBBQSB-UHFFFAOYSA-N 1h-indol-7-yl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC2=C1NC=C2 MXOQUXZPZBBQSB-UHFFFAOYSA-N 0.000 claims 1
- QURMAAVIGALLEC-UHFFFAOYSA-N 2-(1-benzothiophen-2-ylsulfonyl)-6-ethyl-2,6-diazatricyclo[6.3.1.04,12]dodeca-1(11),3,8(12),9-tetraene Chemical compound C1=CC=C2SC(S(=O)(=O)N3C=C4CN(CC=5C=CC=C3C4=5)CC)=CC2=C1 QURMAAVIGALLEC-UHFFFAOYSA-N 0.000 claims 1
- RSIILEAOAXQJTC-UHFFFAOYSA-N 2-(2-chlorophenyl)sulfonyl-6-ethyl-2,6-diazatricyclo[6.3.1.04,12]dodeca-1(11),3,8(12),9-tetraene Chemical compound C=12C3=CC=CC=1CN(CC)CC2=CN3S(=O)(=O)C1=CC=CC=C1Cl RSIILEAOAXQJTC-UHFFFAOYSA-N 0.000 claims 1
- SZJYSBMEFOOVOT-UHFFFAOYSA-N 2-(3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-3-ylsulfonyl)-4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C(S(=O)(=O)N2C=3C=CC=C4CNCCC(C=34)=C2)=C1 SZJYSBMEFOOVOT-UHFFFAOYSA-N 0.000 claims 1
- DCFURUACQHQNFI-UHFFFAOYSA-N 2-(benzenesulfonyl)-6-(1H-imidazol-2-ylmethyl)-2,6-diazatricyclo[6.3.1.04,12]dodeca-1(11),3,8(12),9-tetraene Chemical compound C1=C(C=23)CN(CC=4NC=CN=4)CC3=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 DCFURUACQHQNFI-UHFFFAOYSA-N 0.000 claims 1
- FPKZCBWYZLWHHN-UHFFFAOYSA-N 2-(benzenesulfonyl)-6-(pyrrolidin-2-ylmethyl)-2,6-diazatricyclo[6.3.1.04,12]dodeca-1(11),3,8(12),9-tetraene Chemical compound C1=C(C=23)CN(CC4NCCC4)CC3=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 FPKZCBWYZLWHHN-UHFFFAOYSA-N 0.000 claims 1
- MHBVHFPOTVTIIV-UHFFFAOYSA-N 2-(benzenesulfonyl)-6-(pyrrolidin-3-ylmethyl)-2,6-diazatricyclo[6.3.1.04,12]dodeca-1(11),3,8(12),9-tetraene Chemical compound C1=C(C=23)CN(CC4CNCC4)CC3=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 MHBVHFPOTVTIIV-UHFFFAOYSA-N 0.000 claims 1
- IJLNIWAAFNHRMB-UHFFFAOYSA-N 2-(benzenesulfonyl)-6-ethyl-2,6-diazatricyclo[6.3.1.04,12]dodeca-1(11),3,8(12),9-tetraene Chemical compound C=12C3=CC=CC=1CN(CC)CC2=CN3S(=O)(=O)C1=CC=CC=C1 IJLNIWAAFNHRMB-UHFFFAOYSA-N 0.000 claims 1
- IDBZXZWHWDELAY-UHFFFAOYSA-N 2-(benzenesulfonyl)-6-methyl-2,6-diazatricyclo[6.3.1.04,12]dodeca-1(11),3,8(12),9-tetraene Chemical compound C=12C3=CC=CC=1CN(C)CC2=CN3S(=O)(=O)C1=CC=CC=C1 IDBZXZWHWDELAY-UHFFFAOYSA-N 0.000 claims 1
- XPCBYLKWDFJZJW-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-2,6-diazatricyclo[6.3.1.04,12]dodeca-1(11),3,8(12),9-tetraen-6-yl]-N,N-dimethylethanamine Chemical compound C=12C3=CC=CC=1CN(CCN(C)C)CC2=CN3S(=O)(=O)C1=CC=CC=C1 XPCBYLKWDFJZJW-UHFFFAOYSA-N 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- OGHLQPHXJWUNCN-UHFFFAOYSA-N 3-(1,2-dimethylimidazol-4-yl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound CN1C(C)=NC(S(=O)(=O)N2C=3C=CC=C4CNCCC(C=34)=C2)=C1 OGHLQPHXJWUNCN-UHFFFAOYSA-N 0.000 claims 1
- LHRXWSTUFXVPDK-UHFFFAOYSA-N 3-(1-benzofuran-2-ylsulfonyl)-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1CNCC2=CC=CC3=C2C1=CN3S(=O)(=O)C1=CC2=CC=CC=C2O1 LHRXWSTUFXVPDK-UHFFFAOYSA-N 0.000 claims 1
- RJVMWHMOILEELU-UHFFFAOYSA-N 3-(1-benzothiophen-2-ylsulfonyl)-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1CNCC2=CC=CC3=C2C1=CN3S(=O)(=O)C1=CC2=CC=CC=C2S1 RJVMWHMOILEELU-UHFFFAOYSA-N 0.000 claims 1
- ZZOGUNWAOMZEJM-UHFFFAOYSA-N 3-(1-benzothiophen-3-ylsulfonyl)-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1CNCC2=CC=CC3=C2C1=CN3S(=O)(=O)C1=CSC2=CC=CC=C12 ZZOGUNWAOMZEJM-UHFFFAOYSA-N 0.000 claims 1
- BPBPQSGPSGOITK-UHFFFAOYSA-N 3-(1-methylimidazol-4-yl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound CN1C=NC(S(=O)(=O)N2C=3C=CC=C4CNCCC(C=34)=C2)=C1 BPBPQSGPSGOITK-UHFFFAOYSA-N 0.000 claims 1
- VEQKNDHXVMXBPI-UHFFFAOYSA-N 3-(2,4-difluorophenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound FC1=CC(F)=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 VEQKNDHXVMXBPI-UHFFFAOYSA-N 0.000 claims 1
- DFTKOYUJDUEEOW-UHFFFAOYSA-N 3-(2,5-difluorophenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound FC1=CC=C(F)C(S(=O)(=O)N2C=3C=CC=C4CNCCC(C=34)=C2)=C1 DFTKOYUJDUEEOW-UHFFFAOYSA-N 0.000 claims 1
- UQSLEKLDWURQRH-UHFFFAOYSA-N 3-(2,5-dimethylfuran-3-yl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound O1C(C)=CC(S(=O)(=O)N2C=3C=CC=C4CNCCC(C=34)=C2)=C1C UQSLEKLDWURQRH-UHFFFAOYSA-N 0.000 claims 1
- HIDJWWKDCABFIX-UHFFFAOYSA-N 3-(2,5-dimethylphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound CC1=CC=C(C)C(S(=O)(=O)N2C=3C=CC=C4CNCCC(C=34)=C2)=C1 HIDJWWKDCABFIX-UHFFFAOYSA-N 0.000 claims 1
- VFULUTRECSYTSU-UHFFFAOYSA-N 3-(2,5-dimethylthiophen-3-yl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound S1C(C)=CC(S(=O)(=O)N2C=3C=CC=C4CNCCC(C=34)=C2)=C1C VFULUTRECSYTSU-UHFFFAOYSA-N 0.000 claims 1
- XBRWVPYQEFPNMM-UHFFFAOYSA-N 3-(2,6-difluorophenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound FC1=CC=CC(F)=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 XBRWVPYQEFPNMM-UHFFFAOYSA-N 0.000 claims 1
- KONIGWLFZPECBZ-UHFFFAOYSA-N 3-(2-chloro-6-methylphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 KONIGWLFZPECBZ-UHFFFAOYSA-N 0.000 claims 1
- SXCMVHPFIXZXMR-UHFFFAOYSA-N 3-(2-chlorophenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound ClC1=CC=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 SXCMVHPFIXZXMR-UHFFFAOYSA-N 0.000 claims 1
- OLTLETMORSQJIZ-UHFFFAOYSA-N 3-(2-ethoxy-5-propan-2-ylphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound CCOC1=CC=C(C(C)C)C=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 OLTLETMORSQJIZ-UHFFFAOYSA-N 0.000 claims 1
- JPGKHXYTUDUDDO-UHFFFAOYSA-N 3-(2-methoxy-4-methylphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound COC1=CC(C)=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 JPGKHXYTUDUDDO-UHFFFAOYSA-N 0.000 claims 1
- HDELXLQNDQWJBH-UHFFFAOYSA-N 3-(2-methoxy-5-methylphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 HDELXLQNDQWJBH-UHFFFAOYSA-N 0.000 claims 1
- IQYOCENNLCSLCS-UHFFFAOYSA-N 3-(2-methoxy-6-methylphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound COC1=CC=CC(C)=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 IQYOCENNLCSLCS-UHFFFAOYSA-N 0.000 claims 1
- UYLHSQPLYNPOAU-UHFFFAOYSA-N 3-(2-methylphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound CC1=CC=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 UYLHSQPLYNPOAU-UHFFFAOYSA-N 0.000 claims 1
- HCLFXCNTHCGRIE-UHFFFAOYSA-N 3-(3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-3-ylsulfonyl)benzonitrile Chemical compound C1=C(C=23)CCNCC3=CC=CC=2N1S(=O)(=O)C1=CC=CC(C#N)=C1 HCLFXCNTHCGRIE-UHFFFAOYSA-N 0.000 claims 1
- LGQZNSKGYATOKG-UHFFFAOYSA-N 3-(3,4-difluorophenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1=C(F)C(F)=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 LGQZNSKGYATOKG-UHFFFAOYSA-N 0.000 claims 1
- JRAVWLSYQITGRP-UHFFFAOYSA-N 3-(3,5-difluorophenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound FC1=CC(F)=CC(S(=O)(=O)N2C=3C=CC=C4CNCCC(C=34)=C2)=C1 JRAVWLSYQITGRP-UHFFFAOYSA-N 0.000 claims 1
- HDXZZLXIBGNKHC-UHFFFAOYSA-N 3-(3,5-dimethylphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound CC1=CC(C)=CC(S(=O)(=O)N2C=3C=CC=C4CNCCC(C=34)=C2)=C1 HDXZZLXIBGNKHC-UHFFFAOYSA-N 0.000 claims 1
- JSRQFOATVDUDKP-UHFFFAOYSA-N 3-(3-chloro-2-methylphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 JSRQFOATVDUDKP-UHFFFAOYSA-N 0.000 claims 1
- WFHSFGRMERGQHT-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1=C(Cl)C(F)=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 WFHSFGRMERGQHT-UHFFFAOYSA-N 0.000 claims 1
- XYDMEXRIHZGAEP-UHFFFAOYSA-N 3-(3-chlorophenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound ClC1=CC=CC(S(=O)(=O)N2C=3C=CC=C4CNCCC(C=34)=C2)=C1 XYDMEXRIHZGAEP-UHFFFAOYSA-N 0.000 claims 1
- CIQXLKCGLOJSAU-UHFFFAOYSA-N 3-(3-fluorophenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound FC1=CC=CC(S(=O)(=O)N2C=3C=CC=C4CNCCC(C=34)=C2)=C1 CIQXLKCGLOJSAU-UHFFFAOYSA-N 0.000 claims 1
- OTIFSLPNFUCNTN-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 OTIFSLPNFUCNTN-UHFFFAOYSA-N 0.000 claims 1
- IRMPYMVDDSLWMW-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 IRMPYMVDDSLWMW-UHFFFAOYSA-N 0.000 claims 1
- ZLWNHCXAOHTKKY-UHFFFAOYSA-N 3-(4-methoxyphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 ZLWNHCXAOHTKKY-UHFFFAOYSA-N 0.000 claims 1
- QMWFGFSAHSCSPP-UHFFFAOYSA-N 3-(4-methylphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 QMWFGFSAHSCSPP-UHFFFAOYSA-N 0.000 claims 1
- NVDDRFOERFRXSI-UHFFFAOYSA-N 3-(4-propan-2-ylphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 NVDDRFOERFRXSI-UHFFFAOYSA-N 0.000 claims 1
- RLVJETJHQDOMPZ-UHFFFAOYSA-N 3-(4-propylphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 RLVJETJHQDOMPZ-UHFFFAOYSA-N 0.000 claims 1
- VVRGTJFRTBGAHB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 VVRGTJFRTBGAHB-UHFFFAOYSA-N 0.000 claims 1
- FGSJESQUWVTTFP-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound S1C(Cl)=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 FGSJESQUWVTTFP-UHFFFAOYSA-N 0.000 claims 1
- FBFUIFVARQJZSX-UHFFFAOYSA-N 3-(5-ethyl-2-methoxyphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound CCC1=CC=C(OC)C(S(=O)(=O)N2C=3C=CC=C4CNCCC(C=34)=C2)=C1 FBFUIFVARQJZSX-UHFFFAOYSA-N 0.000 claims 1
- FDMATCVPHUSSRJ-UHFFFAOYSA-N 3-(5-fluoro-2-methylphenyl)sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound CC1=CC=C(F)C=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 FDMATCVPHUSSRJ-UHFFFAOYSA-N 0.000 claims 1
- WKKRCJNLADPSGP-UHFFFAOYSA-N 3-(benzenesulfonyl)-11-ethyl-3,11-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1=C(C2=3)CN(CC)CCC2=CC=CC=3N1S(=O)(=O)C1=CC=CC=C1 WKKRCJNLADPSGP-UHFFFAOYSA-N 0.000 claims 1
- IQCBTUNXAQRCPO-UHFFFAOYSA-N 3-(benzenesulfonyl)-11-methyl-3,11-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1=C(C2=3)CN(C)CCC2=CC=CC=3N1S(=O)(=O)C1=CC=CC=C1 IQCBTUNXAQRCPO-UHFFFAOYSA-N 0.000 claims 1
- KBYIVTOFNUFVHS-UHFFFAOYSA-N 3-(benzenesulfonyl)-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-12-one Chemical compound C1=C(C2=3)C(=O)CNCC2=CC=CC=3N1S(=O)(=O)C1=CC=CC=C1 KBYIVTOFNUFVHS-UHFFFAOYSA-N 0.000 claims 1
- QDLBNXIFNYPGOO-UHFFFAOYSA-N 3-(benzenesulfonyl)-3,11-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1=C(C=23)CNCCC3=CC=CC=2N1S(=O)(=O)C1=CC=CC=C1 QDLBNXIFNYPGOO-UHFFFAOYSA-N 0.000 claims 1
- NAMPQGWZNDHZGR-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-methoxy-9,10-dimethyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4(13),5,7-tetraene Chemical compound C1=C(C2=3)CCN(C)C(C)C=3C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 NAMPQGWZNDHZGR-UHFFFAOYSA-N 0.000 claims 1
- JSNWEDRXKALPPP-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-methoxy-9-methyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4(13),5,7-tetraene Chemical compound C1=C(C2=3)CCNC(C)C=3C(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 JSNWEDRXKALPPP-UHFFFAOYSA-N 0.000 claims 1
- AUDFZEFEHAENTR-UHFFFAOYSA-N 3-[(5-bromo-2,3-dihydro-1-benzofuran-7-yl)sulfonyl]-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1CNCC2=CC=CC3=C2C1=CN3S(=O)(=O)C1=CC(Br)=CC2=C1OCC2 AUDFZEFEHAENTR-UHFFFAOYSA-N 0.000 claims 1
- KRCCVGCPWCIAND-UHFFFAOYSA-N 3-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1CNCC2=CC=CC3=C2C1=CN3S(=O)(=O)C1=C(C)C2=CC(Cl)=CC=C2S1 KRCCVGCPWCIAND-UHFFFAOYSA-N 0.000 claims 1
- BORYLEFKISJIHK-UHFFFAOYSA-N 3-[2-(trifluoromethyl)phenyl]sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound FC(F)(F)C1=CC=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 BORYLEFKISJIHK-UHFFFAOYSA-N 0.000 claims 1
- MCPVTARLKAGTRL-UHFFFAOYSA-N 3-[3-(trifluoromethyl)phenyl]sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2C=3C=CC=C4CNCCC(C=34)=C2)=C1 MCPVTARLKAGTRL-UHFFFAOYSA-N 0.000 claims 1
- XVYUFHWXVRVOMZ-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenyl]sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 XVYUFHWXVRVOMZ-UHFFFAOYSA-N 0.000 claims 1
- KPBYGOWJTXKKAM-UHFFFAOYSA-N 3-[4-fluoro-3-(trifluoromethyl)phenyl]sulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 KPBYGOWJTXKKAM-UHFFFAOYSA-N 0.000 claims 1
- XXWHMIZCYYXHBP-UHFFFAOYSA-N 3-pyridin-3-ylsulfonyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene Chemical compound C1=C(C=23)CCNCC3=CC=CC=2N1S(=O)(=O)C1=CC=CN=C1 XXWHMIZCYYXHBP-UHFFFAOYSA-N 0.000 claims 1
- JUKBCDXNQFULIQ-UHFFFAOYSA-N 4-(3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-3-ylsulfonyl)-3,5-dimethyl-1,2-oxazole Chemical compound CC1=NOC(C)=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 JUKBCDXNQFULIQ-UHFFFAOYSA-N 0.000 claims 1
- BZYUDYAUGGGSDV-UHFFFAOYSA-N 4-(3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-3-ylsulfonyl)benzonitrile Chemical compound C1=C(C=23)CCNCC3=CC=CC=2N1S(=O)(=O)C1=CC=C(C#N)C=C1 BZYUDYAUGGGSDV-UHFFFAOYSA-N 0.000 claims 1
- GTKYAHHXPHVLHN-UHFFFAOYSA-N 5-(3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-3-ylsulfonyl)-2,4-dimethyl-1,3-thiazole Chemical compound S1C(C)=NC(C)=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 GTKYAHHXPHVLHN-UHFFFAOYSA-N 0.000 claims 1
- PMYJVMYDCUOWSM-UHFFFAOYSA-N 5-(3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-3-ylsulfonyl)-2-fluorobenzonitrile Chemical compound C1=C(C#N)C(F)=CC=C1S(=O)(=O)N1C(C=CC=C2CNCC3)=C2C3=C1 PMYJVMYDCUOWSM-UHFFFAOYSA-N 0.000 claims 1
- CUGMEDIZNAIZJK-UHFFFAOYSA-N 5-methyl-1-(phenylsulfonyl)-3,4,5,6-tetrahydro-1h-azepino[5,4,3-cd]indole Chemical compound C=12C3=CC=CC=1CN(C)CCC2=CN3S(=O)(=O)C1=CC=CC=C1 CUGMEDIZNAIZJK-UHFFFAOYSA-N 0.000 claims 1
- PUZRAZDSLPFZBV-UHFFFAOYSA-N 6-(3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-3-ylsulfonyl)-1,3-benzothiazole Chemical compound C1CNCC2=CC=CC3=C2C1=CN3S(=O)(=O)C1=CC=C(N=CS2)C2=C1 PUZRAZDSLPFZBV-UHFFFAOYSA-N 0.000 claims 1
- YGHNAXPTONJHJD-UHFFFAOYSA-N 6-chloro-5-(3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-3-ylsulfonyl)imidazo[2,1-b][1,3]thiazole Chemical compound C1CNCC2=CC=CC3=C2C1=CN3S(=O)(=O)C1=C(Cl)N=C2N1C=CS2 YGHNAXPTONJHJD-UHFFFAOYSA-N 0.000 claims 1
- HDWPPKRQCUSKOL-UHFFFAOYSA-N 6-ethyl-2-[2-(trifluoromethyl)phenyl]sulfonyl-2,6-diazatricyclo[6.3.1.04,12]dodeca-1(11),3,8(12),9-tetraene Chemical compound C=12C3=CC=CC=1CN(CC)CC2=CN3S(=O)(=O)C1=CC=CC=C1C(F)(F)F HDWPPKRQCUSKOL-UHFFFAOYSA-N 0.000 claims 1
- WMHLDULSLHZDIB-UHFFFAOYSA-N 6-methyl-1-(phenylsulfonyl)-3,4,5,6-tetrahydro-1h-azepino[5,4,3-cd]indol-7-ol Chemical compound C=12C3=CC=C(O)C=1C(C)NCCC2=CN3S(=O)(=O)C1=CC=CC=C1 WMHLDULSLHZDIB-UHFFFAOYSA-N 0.000 claims 1
- FNTIMKOXGDBGCH-UHFFFAOYSA-N 6-methyl-1-(phenylsulfonyl)-3,4,5,6-tetrahydro-1h-azepino[5,4,3-cd]indole Chemical compound C=12C3=CC=CC=1C(C)NCCC2=CN3S(=O)(=O)C1=CC=CC=C1 FNTIMKOXGDBGCH-UHFFFAOYSA-N 0.000 claims 1
- YZEYJYUAFAMVRK-UHFFFAOYSA-N 7-ethoxy-6-methyl-1-(phenylsulfonyl)-3,4,5,6-tetrahydro-1h-azepino[5,4,3-cd]indole Chemical compound C1=C(C2=3)CCNC(C)C=3C(OCC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 YZEYJYUAFAMVRK-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- PCKPVGOLPKLUHR-UHFFFAOYSA-N indoxyl Chemical compound C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 150000003951 lactams Chemical group 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0700611 | 2007-03-13 | ||
| US202907P | 2007-11-05 | 2007-11-05 | |
| PCT/EP2008/053002 WO2008110598A1 (en) | 2007-03-13 | 2008-03-13 | Tricyclic isoquinoline derivatives for treatment of obesity |
Publications (2)
| Publication Number | Publication Date |
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| JP2010520917A JP2010520917A (ja) | 2010-06-17 |
| JP2010520917A5 true JP2010520917A5 (enExample) | 2011-05-06 |
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| EP (1) | EP2134714A1 (enExample) |
| JP (1) | JP2010520917A (enExample) |
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| EA (1) | EA016592B1 (enExample) |
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Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2724449C (en) | 2008-05-29 | 2017-05-30 | Albany Molecular Research, Inc. | 5-ht3 receptor modulators, methods of making, and use thereof |
| EP2575815A4 (en) | 2010-06-04 | 2013-12-25 | Albany Molecular Res Inc | GLYCIN TRANSPORTER 1 INHIBITORS, METHODS OF MAKING THE SAME, AND USES THEREOF |
| WO2012106448A1 (en) * | 2011-02-02 | 2012-08-09 | Biocryst Pharmaceuticals, Inc. | Heterocyclic compounds as janus kinase inhibitors |
| JP6198715B2 (ja) * | 2012-03-06 | 2017-09-20 | 武田薬品工業株式会社 | 三環性化合物 |
| US10675283B2 (en) | 2017-03-24 | 2020-06-09 | University Of South Florida | Compositions and methods for white to beige adipogenesis |
| CN109180687A (zh) * | 2018-08-31 | 2019-01-11 | 山东轩德医药科技有限公司 | 一种瑞卡帕步中间体的制备方法 |
| CN111961047A (zh) * | 2020-08-19 | 2020-11-20 | 南通大学 | 一种6-乙氧基-3,4-二氢-2,7-萘啶-1（2h）-酮及其合成方法 |
| CN115925658B (zh) * | 2022-11-21 | 2024-02-27 | 常州佳德医药科技有限公司 | 一种2-氨基乙基呋喃的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795451A (fr) * | 1972-02-23 | 1973-08-16 | Pfizer | Agents hypoglycemiants aza indoliques tricycliques |
| US3950343A (en) * | 1973-11-06 | 1976-04-13 | Ayerst, Mckenna And Harrison Ltd. | Pyrroloisoquinoline derivatives |
| MX9700693A (es) | 1994-07-26 | 1997-04-30 | Pfizer | Derivados del 4-indol. |
| US6133287A (en) * | 1998-03-24 | 2000-10-17 | Allelix Biopharmaceuticals Inc. | Piperidine-indole compounds having 5-HT6 affinity |
| GB9820113D0 (en) | 1998-09-15 | 1998-11-11 | Merck Sharp & Dohme | Therapeutic agents |
| MXPA01005905A (es) | 1998-12-11 | 2002-09-18 | Univ Virginia Commonwealth | Ligandos selectivos de receptores de 5-ht6. |
| WO2002032863A1 (en) | 2000-10-20 | 2002-04-25 | Biovitrum Ab | 2-, 3-, 4-, or 5-substituted-n1-(benzensulfonyl)indoles and their use in therapy |
| PL374401A1 (en) * | 2002-06-05 | 2005-10-17 | F.Hoffmann-La Roche Ag | 1-sulfonyl-4-aminoalkoxy indole derivatives as 5-ht6-receptor modulators for the treatment of cns-disorders |
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2008
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- 2008-03-13 EP EP08717746A patent/EP2134714A1/en not_active Withdrawn
- 2008-03-13 US US12/075,979 patent/US8138333B2/en not_active Expired - Fee Related
- 2008-03-13 JP JP2009553146A patent/JP2010520917A/ja not_active Withdrawn
- 2008-03-13 AU AU2008225753A patent/AU2008225753A1/en not_active Abandoned
- 2008-03-13 WO PCT/EP2008/053002 patent/WO2008110598A1/en not_active Ceased
- 2008-03-13 CN CN200880008061A patent/CN101631787A/zh active Pending
- 2008-03-13 EA EA200970849A patent/EA016592B1/ru not_active IP Right Cessation
- 2008-03-13 CA CA002679346A patent/CA2679346A1/en not_active Abandoned
- 2008-03-13 NZ NZ579360A patent/NZ579360A/en not_active IP Right Cessation
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