JP2010520917A - 肥満治療用三環式イソキノリン誘導体 - Google Patents

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Publication number

JP2010520917A

JP2010520917A JP2009553146A JP2009553146A JP2010520917A JP 2010520917 A JP2010520917 A JP 2010520917A JP 2009553146 A JP2009553146 A JP 2009553146A JP 2009553146 A JP2009553146 A JP 2009553146A JP 2010520917 A JP2010520917 A JP 2010520917A

Authority

JP

Japan

Prior art keywords

azepino

tetrahydro

indole

alkyl

sulfonyl

Prior art date

2007-03-13

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Withdrawn

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• 238000011282 treatment Methods 0.000 title claims description 17
• 208000008589 Obesity Diseases 0.000 title description 8
• 235000020824 obesity Nutrition 0.000 title description 8
• 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 198
• 238000000034 method Methods 0.000 claims abstract description 80
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
• 239000003814 drug Substances 0.000 claims abstract description 9
• -1 imidazolyl-methyl Chemical group 0.000 claims description 85
• 239000000203 mixture Substances 0.000 claims description 57
• 125000003118 aryl group Chemical group 0.000 claims description 36
• 150000003839 salts Chemical class 0.000 claims description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims description 33
• 239000001257 hydrogen Substances 0.000 claims description 33
• 108020003175 receptors Proteins 0.000 claims description 33
• 102000005962 receptors Human genes 0.000 claims description 33
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• 125000001072 heteroaryl group Chemical group 0.000 claims description 24
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 20
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 13
• 241000282414 Homo sapiens Species 0.000 claims description 13
• 125000001153 fluoro group Chemical group F* 0.000 claims description 11
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
• 230000037396 body weight Effects 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 239000004480 active ingredient Substances 0.000 claims description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
• 230000000694 effects Effects 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
• 230000004584 weight gain Effects 0.000 claims description 7
• 235000019786 weight gain Nutrition 0.000 claims description 7
• 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 description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
• 230000003287 optical effect Effects 0.000 claims description 6
• 239000004031 partial agonist Substances 0.000 claims description 6
• 230000002265 prevention Effects 0.000 claims description 6
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 230000009467 reduction Effects 0.000 claims description 5
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 150000004677 hydrates Chemical class 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 150000003951 lactams Chemical group 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 239000012453 solvate Substances 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 125000004104 aryloxy group Chemical group 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• 238000011321 prophylaxis Methods 0.000 claims description 3
• 239000003751 serotonin 6 antagonist Substances 0.000 claims description 3
• 238000002560 therapeutic procedure Methods 0.000 claims description 3
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
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