NO317099B1 - Kaliumkanalapnere - Google Patents

Info

Publication number

NO317099B1

NO317099B1 NO20003104A NO20003104A NO317099B1 NO 317099 B1 NO317099 B1 NO 317099B1 NO 20003104 A NO20003104 A NO 20003104A NO 20003104 A NO20003104 A NO 20003104A NO 317099 B1 NO317099 B1 NO 317099B1

Authority

NO

Norway

Prior art keywords

dioxide

hexahydro

quinolin

thiopyrano

pyridin

Prior art date

1997-12-18

Links

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• 150000001875 compounds Chemical class 0.000 claims abstract description 188
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 62
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 31
• -1 benzoxadiazolyl Chemical group 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 20
• 229940079593 drug Drugs 0.000 claims description 19
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 12
• 150000002367 halogens Chemical class 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 12
• 238000011282 treatment Methods 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 206010046543 Urinary incontinence Diseases 0.000 claims description 10
• XEDAGIRDUFLQRA-UHFFFAOYSA-N 10-(3-bromo-4-fluorophenyl)-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)CCC2)=C2NC2=C1SCCC2 XEDAGIRDUFLQRA-UHFFFAOYSA-N 0.000 claims description 9
• 150000001408 amides Chemical class 0.000 claims description 9
• 208000035475 disorder Diseases 0.000 claims description 9
• 150000002148 esters Chemical class 0.000 claims description 9
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 7
• 208000030814 Eating disease Diseases 0.000 claims description 7
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
• 206010020772 Hypertension Diseases 0.000 claims description 7
• 208000019695 Migraine disease Diseases 0.000 claims description 7
• 208000002193 Pain Diseases 0.000 claims description 7
• 208000003782 Raynaud disease Diseases 0.000 claims description 7
• 208000012322 Raynaud phenomenon Diseases 0.000 claims description 7
• 208000006673 asthma Diseases 0.000 claims description 7
• 235000014632 disordered eating Nutrition 0.000 claims description 7
• 206010015037 epilepsy Diseases 0.000 claims description 7
• 201000001881 impotence Diseases 0.000 claims description 7
• 206010027599 migraine Diseases 0.000 claims description 7
• 230000004770 neurodegeneration Effects 0.000 claims description 7
• BRMYWLUQYFDDGP-UHFFFAOYSA-N 8-(3-bromo-4-fluorophenyl)-6-thia-2-azatricyclo[7.3.0.03,7]dodeca-1(9),3(7)-dien-10-one Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)CC2)=C2NC2=C1SCC2 BRMYWLUQYFDDGP-UHFFFAOYSA-N 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• GQUXOOISWZKGIA-UHFFFAOYSA-N 10-(3,4-difluorophenyl)-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound C1=C(F)C(F)=CC=C1C1C(C(=O)CCC2)=C2NC2=C1SCCC2 GQUXOOISWZKGIA-UHFFFAOYSA-N 0.000 claims description 5
• QCDZUVYDSDNBAZ-UHFFFAOYSA-N 10-(3-fluorophenyl)-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound FC1=CC=CC(C2C3=C(CCCC3=O)NC3=C2SCCC3)=C1 QCDZUVYDSDNBAZ-UHFFFAOYSA-N 0.000 claims description 5
• YOMOCHJDSBVHDK-UHFFFAOYSA-N 9-(3,4-difluorophenyl)-3,4,5,6,7,9-hexahydro-2h-thieno[3,2-b]quinolin-8-one Chemical compound C1=C(F)C(F)=CC=C1C1C(C(=O)CCC2)=C2NC2=C1SCC2 YOMOCHJDSBVHDK-UHFFFAOYSA-N 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• YKLFYUYAQYKRAE-UHFFFAOYSA-N 10-(3,4,5-trifluorophenyl)-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound FC1=C(F)C(F)=CC(C2C3=C(CCCC3=O)NC3=C2SCCC3)=C1 YKLFYUYAQYKRAE-UHFFFAOYSA-N 0.000 claims description 4
• WODMAHYOWKPGOD-UHFFFAOYSA-N 10-(3,4-dichlorophenyl)-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1C(C(=O)CCC2)=C2NC2=C1SCCC2 WODMAHYOWKPGOD-UHFFFAOYSA-N 0.000 claims description 4
• BLLZWSHIIQKBOC-UHFFFAOYSA-N 10-(3-bromophenyl)-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound BrC1=CC=CC(C2C3=C(CCCC3=O)NC3=C2SCCC3)=C1 BLLZWSHIIQKBOC-UHFFFAOYSA-N 0.000 claims description 4
• FMDHPPAOTZLKSC-UHFFFAOYSA-N 10-(3-chloro-4-fluorophenyl)-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound C1=C(Cl)C(F)=CC=C1C1C(C(=O)CCC2)=C2NC2=C1SCCC2 FMDHPPAOTZLKSC-UHFFFAOYSA-N 0.000 claims description 4
• HBLRTIDTQUYDKU-UHFFFAOYSA-N 10-(3-chlorophenyl)-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound ClC1=CC=CC(C2C3=C(CCCC3=O)NC3=C2SCCC3)=C1 HBLRTIDTQUYDKU-UHFFFAOYSA-N 0.000 claims description 4
• MSIUJIBLNVQNHN-UHFFFAOYSA-N 10-(3-nitrophenyl)-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound [O-][N+](=O)C1=CC=CC(C2C3=C(CCCC3=O)NC3=C2SCCC3)=C1 MSIUJIBLNVQNHN-UHFFFAOYSA-N 0.000 claims description 4
• XABVJICWRLPYGF-UHFFFAOYSA-N 10-(4-bromophenyl)-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound C1=CC(Br)=CC=C1C1C(C(=O)CCC2)=C2NC2=C1SCCC2 XABVJICWRLPYGF-UHFFFAOYSA-N 0.000 claims description 4
• OCUHRANHCVHAHB-UHFFFAOYSA-N 10-(4-chloro-3-fluorophenyl)-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound C1=C(Cl)C(F)=CC(C2C3=C(CCCC3=O)NC3=C2SCCC3)=C1 OCUHRANHCVHAHB-UHFFFAOYSA-N 0.000 claims description 4
• FWUYFQRMPZVWGX-UHFFFAOYSA-N 10-(4-chloro-3-nitrophenyl)-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C2C3=C(CCCC3=O)NC3=C2SCCC3)=C1 FWUYFQRMPZVWGX-UHFFFAOYSA-N 0.000 claims description 4
• SFTMFLPMOCYSLR-UHFFFAOYSA-N 10-(4-methyl-3-nitrophenyl)-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1C1C(C(=O)CCC2)=C2NC2=C1SCCC2 SFTMFLPMOCYSLR-UHFFFAOYSA-N 0.000 claims description 4
• PUKYFLOUTAYHEP-UHFFFAOYSA-N 10-[3-(trifluoromethyl)phenyl]-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound FC(F)(F)C1=CC=CC(C2C3=C(CCCC3=O)NC3=C2SCCC3)=C1 PUKYFLOUTAYHEP-UHFFFAOYSA-N 0.000 claims description 4
• UOHLCLTYTHCWEM-UHFFFAOYSA-N 10-[3-fluoro-5-(trifluoromethyl)phenyl]-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound FC(F)(F)C1=CC(F)=CC(C2C3=C(CCCC3=O)NC3=C2SCCC3)=C1 UOHLCLTYTHCWEM-UHFFFAOYSA-N 0.000 claims description 4
• UFQHCQDZEDLCBO-UHFFFAOYSA-N 10-[4-(trifluoromethyl)phenyl]-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1C(C(=O)CCC2)=C2NC2=C1SCCC2 UFQHCQDZEDLCBO-UHFFFAOYSA-N 0.000 claims description 4
• TYKNPTZOHKBGIS-UHFFFAOYSA-N 10-[4-fluoro-3-(trifluoromethyl)phenyl]-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1C1C(C(=O)CCC2)=C2NC2=C1SCCC2 TYKNPTZOHKBGIS-UHFFFAOYSA-N 0.000 claims description 4
• NFQWYTOJELOVRD-UHFFFAOYSA-N 10-pyridin-4-yl-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound O=C1CCCC(NC2=C3SCCC2)=C1C3C1=CC=NC=C1 NFQWYTOJELOVRD-UHFFFAOYSA-N 0.000 claims description 4
• ZTDCYTCFOBXULR-UHFFFAOYSA-N 3-(8-oxo-3,4,5,6,7,9-hexahydro-2h-thieno[3,2-b]quinolin-9-yl)benzonitrile Chemical compound O=C1CCCC(NC2=C3SCC2)=C1C3C1=CC=CC(C#N)=C1 ZTDCYTCFOBXULR-UHFFFAOYSA-N 0.000 claims description 4
• UIUKLRCKXACBDG-UHFFFAOYSA-N 8-(3-bromo-4-fluorophenyl)-10-thia-2-azatricyclo[7.4.0.03,7]trideca-1(9),3(7)-dien-6-one Chemical compound C1=C(Br)C(F)=CC=C1C1C(SCCC2)=C2NC2=C1C(=O)CC2 UIUKLRCKXACBDG-UHFFFAOYSA-N 0.000 claims description 4
• DXQPPNNHHOXZOL-UHFFFAOYSA-N 9-(3,4-dichlorophenyl)-3,4,5,6,7,9-hexahydro-2h-thieno[3,2-b]quinolin-8-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1C(C(=O)CCC2)=C2NC2=C1SCC2 DXQPPNNHHOXZOL-UHFFFAOYSA-N 0.000 claims description 4
• XSXLZZYRVXBFMT-UHFFFAOYSA-N 9-(3,4-dichlorophenyl)-3,4,5,6,7,9-hexahydrocyclopenta[b]thiopyrano [2,3-e]pyridin-8(2h)-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1C(SCCC2)=C2NC2=C1C(=O)CC2 XSXLZZYRVXBFMT-UHFFFAOYSA-N 0.000 claims description 4
• XKCUBMCJEXEHDA-UHFFFAOYSA-N 9-(3-bromo-4-fluorophenyl)-3,4,5,6,7,9-hexahydro-2h-thieno[3,2-b]quinolin-8-one Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)CCC2)=C2NC2=C1SCC2 XKCUBMCJEXEHDA-UHFFFAOYSA-N 0.000 claims description 4
• JOMZYQIZURXWOG-UHFFFAOYSA-N 9-(3-nitrophenyl)-3,4,5,6,7,9-hexahydro-2h-thieno[3,2-b]quinolin-8-one Chemical compound [O-][N+](=O)C1=CC=CC(C2C3=C(CCCC3=O)NC3=C2SCC3)=C1 JOMZYQIZURXWOG-UHFFFAOYSA-N 0.000 claims description 4
• YQVJORPHMOUXGO-UHFFFAOYSA-N 9-(4-chloro-3-nitrophenyl)-3,4,5,6,7,9-hexahydro-2h-thieno[3,2-b]quinolin-8-one Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C2C3=C(CCCC3=O)NC3=C2SCC3)=C1 YQVJORPHMOUXGO-UHFFFAOYSA-N 0.000 claims description 4
• HGSNLGJWHWCHRX-UHFFFAOYSA-N 9-(4-fluoro-3-iodophenyl)-3,4,5,6,7,9-hexahydro-2h-thieno[3,2-b]quinolin-8-one Chemical compound C1=C(I)C(F)=CC=C1C1C(C(=O)CCC2)=C2NC2=C1SCC2 HGSNLGJWHWCHRX-UHFFFAOYSA-N 0.000 claims description 4
• ZFUSOYBCAXSYLP-UHFFFAOYSA-N 9-(4-methyl-3-nitrophenyl)-3,4,5,6,7,9-hexahydro-2h-thieno[3,2-b]quinolin-8-one Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1C1C(C(=O)CCC2)=C2NC2=C1SCC2 ZFUSOYBCAXSYLP-UHFFFAOYSA-N 0.000 claims description 4
• RGVFOVCSSWNZON-UHFFFAOYSA-N 9-[4-fluoro-3-(trifluoromethyl)phenyl]-3,4,5,6,7,9-hexahydro-2h-thieno[3,2-b]quinolin-8-one Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1C1C(C(=O)CCC2)=C2NC2=C1SCC2 RGVFOVCSSWNZON-UHFFFAOYSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 229910052739 hydrogen Inorganic materials 0.000 claims description 4
• 239000001257 hydrogen Substances 0.000 claims description 4
• GLEKEJSYQUFSJJ-UHFFFAOYSA-N 10-phenyl-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound O=C1CCCC(NC2=C3SCCC2)=C1C3C1=CC=CC=C1 GLEKEJSYQUFSJJ-UHFFFAOYSA-N 0.000 claims description 3
• DYGMQFYEGPDFJF-UHFFFAOYSA-N 10-pyridin-3-yl-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-9-one Chemical compound O=C1CCCC(NC2=C3SCCC2)=C1C3C1=CC=CN=C1 DYGMQFYEGPDFJF-UHFFFAOYSA-N 0.000 claims description 3
• OQDPAWKLDAFPBT-UHFFFAOYSA-N 3-(9-oxo-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b]quinolin-10-yl)benzonitrile Chemical compound O=C1CCCC(NC2=C3SCCC2)=C1C3C1=CC=CC(C#N)=C1 OQDPAWKLDAFPBT-UHFFFAOYSA-N 0.000 claims description 3
• MRXWCNUJJPQBOT-UHFFFAOYSA-N 8-(3-bromophenyl)-6-thia-2-azatricyclo[7.3.0.03,7]dodeca-1(9),3(7)-dien-10-one Chemical compound BrC1=CC=CC(C2C3=C(CCC3=O)NC3=C2SCC3)=C1 MRXWCNUJJPQBOT-UHFFFAOYSA-N 0.000 claims description 3
• UQOPONKFSMGKRK-UHFFFAOYSA-N 8-(4-bromo-2-thienyl)-2,3,4,5,6,8-hexahydro-7h-cyclopenta[b]thieno [2,3-e]pyridin-7-one Chemical compound BrC1=CSC(C2C3=C(CCC3=O)NC3=C2SCC3)=C1 UQOPONKFSMGKRK-UHFFFAOYSA-N 0.000 claims description 3
• IKZCZRYTDTYKCY-UHFFFAOYSA-N 8-(4-bromophenyl)-6-thia-2-azatricyclo[7.3.0.03,7]dodeca-1(9),3(7)-dien-10-one Chemical compound C1=CC(Br)=CC=C1C1C(C(=O)CC2)=C2NC2=C1SCC2 IKZCZRYTDTYKCY-UHFFFAOYSA-N 0.000 claims description 3
• LNBGJPGGENBKCV-UHFFFAOYSA-N 8-(4-chloro-3-nitrophenyl)-6-thia-2-azatricyclo[7.3.0.03,7]dodeca-1(9),3(7)-dien-10-one Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C2C3=C(CCC3=O)NC3=C2SCC3)=C1 LNBGJPGGENBKCV-UHFFFAOYSA-N 0.000 claims description 3
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 3
• BRMYWLUQYFDDGP-CQSZACIVSA-N (8R)-8-(3-bromo-4-fluorophenyl)-6-thia-2-azatricyclo[7.3.0.03,7]dodeca-1(9),3(7)-dien-10-one Chemical compound C1=C(Br)C(F)=CC=C1[C@@H]1C(C(=O)CC2)=C2NC2=C1SCC2 BRMYWLUQYFDDGP-CQSZACIVSA-N 0.000 claims description 2
• BRMYWLUQYFDDGP-AWEZNQCLSA-N (8S)-8-(3-bromo-4-fluorophenyl)-6-thia-2-azatricyclo[7.3.0.03,7]dodeca-1(9),3(7)-dien-10-one Chemical compound C1=C(Br)C(F)=CC=C1[C@H]1C(C(=O)CC2)=C2NC2=C1SCC2 BRMYWLUQYFDDGP-AWEZNQCLSA-N 0.000 claims description 2
• FPXMQHRBVCKNIW-OAHLLOKOSA-N (9r)-9-(2,1,3-benzoxadiazol-5-yl)-3,4,5,6,7,9-hexahydro-2h-thieno[3,2-b]quinolin-8-one Chemical compound C1=CC2=NON=C2C=C1[C@@H](C=1SCCC=1N1)C2=C1CCCC2=O FPXMQHRBVCKNIW-OAHLLOKOSA-N 0.000 claims description 2
• DXQPPNNHHOXZOL-OAHLLOKOSA-N (9r)-9-(3,4-dichlorophenyl)-3,4,5,6,7,9-hexahydro-2h-thieno[3,2-b]quinolin-8-one Chemical compound C1=C(Cl)C(Cl)=CC=C1[C@@H]1C(C(=O)CCC2)=C2NC2=C1SCC2 DXQPPNNHHOXZOL-OAHLLOKOSA-N 0.000 claims description 2
• YQVJORPHMOUXGO-OAHLLOKOSA-N (9r)-9-(4-chloro-3-nitrophenyl)-3,4,5,6,7,9-hexahydro-2h-thieno[3,2-b]quinolin-8-one Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC([C@@H]2C3=C(CCCC3=O)NC3=C2SCC3)=C1 YQVJORPHMOUXGO-OAHLLOKOSA-N 0.000 claims description 2
• FPXMQHRBVCKNIW-HNNXBMFYSA-N (9s)-9-(2,1,3-benzoxadiazol-5-yl)-3,4,5,6,7,9-hexahydro-2h-thieno[3,2-b]quinolin-8-one Chemical compound C1=CC2=NON=C2C=C1[C@H](C=1SCCC=1N1)C2=C1CCCC2=O FPXMQHRBVCKNIW-HNNXBMFYSA-N 0.000 claims description 2
• DXQPPNNHHOXZOL-HNNXBMFYSA-N (9s)-9-(3,4-dichlorophenyl)-3,4,5,6,7,9-hexahydro-2h-thieno[3,2-b]quinolin-8-one Chemical compound C1=C(Cl)C(Cl)=CC=C1[C@H]1C(C(=O)CCC2)=C2NC2=C1SCC2 DXQPPNNHHOXZOL-HNNXBMFYSA-N 0.000 claims description 2
• XKCUBMCJEXEHDA-HNNXBMFYSA-N (9s)-9-(3-bromo-4-fluorophenyl)-3,4,5,6,7,9-hexahydro-2h-thieno[3,2-b]quinolin-8-one Chemical compound C1=C(Br)C(F)=CC=C1[C@H]1C(C(=O)CCC2)=C2NC2=C1SCC2 XKCUBMCJEXEHDA-HNNXBMFYSA-N 0.000 claims description 2
• GYOUARGCPLTMJD-UHFFFAOYSA-N 1-[8-(4-chloro-3-nitrophenyl)-6-methyl-1,1-dioxo-3,4,5,8-tetrahydro-2h-thiopyrano[3,2-b]pyridin-7-yl]ethanone Chemical compound CC(=O)C1=C(C)NC(CCCS2(=O)=O)=C2C1C1=CC=C(Cl)C([N+]([O-])=O)=C1 GYOUARGCPLTMJD-UHFFFAOYSA-N 0.000 claims description 2
• CVDVLEPOMDZYRD-UHFFFAOYSA-N 10-(3-bromo-4-fluorophenyl)-2,3,4,5,6,7,8,10-octahydro-9h-cyclopenta[b]thiepino[2,3-e]pyridin-9-one Chemical compound C1=C(Br)C(F)=CC=C1C1C(SCCCC2)=C2NC2=C1C(=O)CC2 CVDVLEPOMDZYRD-UHFFFAOYSA-N 0.000 claims description 2
• YLNCMJBZJWCKGM-UHFFFAOYSA-N 3-(10-oxo-6-thia-2-azatricyclo[7.3.0.03,7]dodeca-1(9),3(7)-dien-8-yl)benzonitrile Chemical compound O=C1CCC(NC2=C3SCC2)=C1C3C1=CC=CC(C#N)=C1 YLNCMJBZJWCKGM-UHFFFAOYSA-N 0.000 claims description 2
• POZBSCBKLKBYCS-UHFFFAOYSA-N 3-(6-oxo-10-thia-2-azatricyclo[7.4.0.03,7]trideca-1(9),3(7)-dien-8-yl)benzonitrile Chemical compound O=C1CCC(NC2=C3SCCC2)=C1C3C1=CC=CC(C#N)=C1 POZBSCBKLKBYCS-UHFFFAOYSA-N 0.000 claims description 2
• PSYUDRVGMAYKFT-UHFFFAOYSA-N 4-(10-oxo-6-thia-2-azatricyclo[7.3.0.03,7]dodeca-1(9),3(7)-dien-8-yl)pyridine-2-carbonitrile Chemical compound O=C1CCC(NC2=C3SCC2)=C1C3C1=CC=NC(C#N)=C1 PSYUDRVGMAYKFT-UHFFFAOYSA-N 0.000 claims description 2
• YYQMCQABMFYKRB-UHFFFAOYSA-N 8-(2,1,3-benzoxadiazol-5-yl)-6-thia-2-azatricyclo[7.3.0.03,7]dodeca-1(9),3(7)-dien-10-one Chemical compound C1=CC2=NON=C2C=C1C(C=1SCCC=1N1)C2=C1CCC2=O YYQMCQABMFYKRB-UHFFFAOYSA-N 0.000 claims description 2
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