JP2015520764A5 - - Google Patents
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- Publication number
- JP2015520764A5 JP2015520764A5 JP2015513270A JP2015513270A JP2015520764A5 JP 2015520764 A5 JP2015520764 A5 JP 2015520764A5 JP 2015513270 A JP2015513270 A JP 2015513270A JP 2015513270 A JP2015513270 A JP 2015513270A JP 2015520764 A5 JP2015520764 A5 JP 2015520764A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- dihydro
- triazol
- phenyl
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 49
- 229910052739 hydrogen Inorganic materials 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 29
- 125000005843 halogen group Chemical group 0.000 claims 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- -1 R 24 Chemical compound 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000006413 ring segment Chemical group 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 208000016354 hearing loss disease Diseases 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- CZHVMIZYDXTWLF-UHFFFAOYSA-N 3-methyl-4-[6-[[3-methyl-3-(trifluoromethyl)-1h-2-benzofuran-5-yl]oxy]pyridin-3-yl]-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC2(C)C(F)(F)F)C2=C1 CZHVMIZYDXTWLF-UHFFFAOYSA-N 0.000 claims 2
- IYAYIZYTDQZOAS-UHFFFAOYSA-N 4-[6-[(3-tert-butyl-1,3-dihydro-2-benzofuran-5-yl)oxy]pyridin-3-yl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC2C(C)(C)C)C2=C1 IYAYIZYTDQZOAS-UHFFFAOYSA-N 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 208000020685 sleep-wake disease Diseases 0.000 claims 2
- MDTUWBLTRPRXBX-UHFFFAOYSA-N 1,2,4-triazol-3-one Chemical compound O=C1N=CN=N1 MDTUWBLTRPRXBX-UHFFFAOYSA-N 0.000 claims 1
- SWCKNZPFWDTENM-UHFFFAOYSA-N 3-methyl-4-(5-methyl-6-spiro[2h-1-benzofuran-3,1'-cyclopropane]-4-yloxypyridin-3-yl)-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1C)=CN=C1OC1=CC=CC2=C1C1(CC1)CO2 SWCKNZPFWDTENM-UHFFFAOYSA-N 0.000 claims 1
- MAYXIKTYUMBPIQ-UHFFFAOYSA-N 3-methyl-4-(6-spiro[1h-2-benzofuran-3,1'-cyclobutane]-5-yloxypyridin-3-yl)-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC23CCC3)C2=C1 MAYXIKTYUMBPIQ-UHFFFAOYSA-N 0.000 claims 1
- NQUBKMMQOUJYMZ-UHFFFAOYSA-N 3-methyl-4-(6-spiro[1h-2-benzofuran-3,1'-cyclopentane]-5-yloxypyridin-3-yl)-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC23CCCC3)C2=C1 NQUBKMMQOUJYMZ-UHFFFAOYSA-N 0.000 claims 1
- QJEJEPKGWPVGQU-UHFFFAOYSA-N 3-methyl-4-(6-spiro[2h-1-benzofuran-3,1'-cyclopropane]-4-yloxypyridin-3-yl)-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=N1)=CC=C1OC1=CC=CC2=C1C1(CC1)CO2 QJEJEPKGWPVGQU-UHFFFAOYSA-N 0.000 claims 1
- BDINBEGKCACPFR-UHFFFAOYSA-N 3-methyl-4-[2-(7-methylspiro[2h-1-benzofuran-3,1'-cyclopropane]-4-yl)oxypyrimidin-5-yl]-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=N1)=CN=C1OC1=CC=C(C)C2=C1C1(CC1)CO2 BDINBEGKCACPFR-UHFFFAOYSA-N 0.000 claims 1
- OKLXJCHECGELKY-UHFFFAOYSA-N 3-methyl-4-[4-(2-methylphenoxy)phenyl]-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=CC=CC=C1C OKLXJCHECGELKY-UHFFFAOYSA-N 0.000 claims 1
- JPCZXWMSLWBUPH-UHFFFAOYSA-N 3-methyl-4-[4-(3-methylphenoxy)phenyl]-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=CC=CC(C)=C1 JPCZXWMSLWBUPH-UHFFFAOYSA-N 0.000 claims 1
- CRDQQBJKVMJSBK-UHFFFAOYSA-N 3-methyl-4-[4-(3-propan-2-ylphenoxy)phenyl]-1h-1,2,4-triazol-5-one Chemical compound CC(C)C1=CC=CC(OC=2C=CC(=CC=2)N2C(NN=C2C)=O)=C1 CRDQQBJKVMJSBK-UHFFFAOYSA-N 0.000 claims 1
- KURMQXDUSWKHDV-UHFFFAOYSA-N 3-methyl-4-[4-[3-(trifluoromethoxy)phenoxy]phenyl]-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=CC=CC(OC(F)(F)F)=C1 KURMQXDUSWKHDV-UHFFFAOYSA-N 0.000 claims 1
- RPSAGKHXCFJOSR-UHFFFAOYSA-N 3-methyl-4-[5-methyl-6-(3-propan-2-ylphenoxy)pyridin-3-yl]-1h-1,2,4-triazol-5-one Chemical compound CC(C)C1=CC=CC(OC=2C(=CC(=CN=2)N2C(NN=C2C)=O)C)=C1 RPSAGKHXCFJOSR-UHFFFAOYSA-N 0.000 claims 1
- MLVZXLGUAWWQTM-UHFFFAOYSA-N 3-methyl-4-[5-methyl-6-(7-methylspiro[2h-1-benzofuran-3,1'-cyclopropane]-4-yl)oxypyridin-3-yl]-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1C)=CN=C1OC1=CC=C(C)C2=C1C1(CC1)CO2 MLVZXLGUAWWQTM-UHFFFAOYSA-N 0.000 claims 1
- AEWMLCWSDURMER-UHFFFAOYSA-N 3-methyl-4-[6-(3-propan-2-ylphenoxy)pyridin-3-yl]-1H-1,2,4-triazol-5-one Chemical compound CC(C)c1cccc(Oc2ccc(cn2)-n2c(C)n[nH]c2=O)c1 AEWMLCWSDURMER-UHFFFAOYSA-N 0.000 claims 1
- SXVVXFKHWPURFB-UHFFFAOYSA-N 3-methyl-4-[6-(7-methylspiro[2h-1-benzofuran-3,1'-cyclopropane]-4-yl)oxypyridin-3-yl]-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=N1)=CC=C1OC1=CC=C(C)C2=C1C1(CC1)CO2 SXVVXFKHWPURFB-UHFFFAOYSA-N 0.000 claims 1
- QYACMTXZEJKARP-UHFFFAOYSA-N 3-methyl-4-[6-[(3,3,7-trimethyl-2h-1-benzofuran-4-yl)oxy]pyridin-3-yl]-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=N1)=CC=C1OC1=CC=C(C)C2=C1C(C)(C)CO2 QYACMTXZEJKARP-UHFFFAOYSA-N 0.000 claims 1
- KSWCRXAOXLLWTG-UHFFFAOYSA-N 3-methyl-4-[6-[4-methyl-3-(trifluoromethoxy)phenoxy]pyridin-3-yl]-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=N1)=CC=C1OC1=CC=C(C)C(OC(F)(F)F)=C1 KSWCRXAOXLLWTG-UHFFFAOYSA-N 0.000 claims 1
- NJRMOMWWHLVMPA-UHFFFAOYSA-N 4-[4-(2,3-dimethylphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=CC=CC(C)=C1C NJRMOMWWHLVMPA-UHFFFAOYSA-N 0.000 claims 1
- PWWRDVISZORIGY-UHFFFAOYSA-N 4-[4-(2,5-dimethylphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=CC(C)=CC=C1C PWWRDVISZORIGY-UHFFFAOYSA-N 0.000 claims 1
- PYBBOFCEIUGTFC-UHFFFAOYSA-N 4-[4-(2,6-dimethylphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=C(C)C=CC=C1C PYBBOFCEIUGTFC-UHFFFAOYSA-N 0.000 claims 1
- YGXKHVQVHCHPMB-UHFFFAOYSA-N 4-[4-(2-ethylphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CCC1=CC=CC=C1OC1=CC=C(N2C(NN=C2C)=O)C=C1 YGXKHVQVHCHPMB-UHFFFAOYSA-N 0.000 claims 1
- HNFWLUZIWLJEDP-UHFFFAOYSA-N 4-[4-(2-fluoro-6-methylphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=C(C)C=CC=C1F HNFWLUZIWLJEDP-UHFFFAOYSA-N 0.000 claims 1
- VCBGOWIRWGFAOF-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 VCBGOWIRWGFAOF-UHFFFAOYSA-N 0.000 claims 1
- PBTGLAKUUZQCOX-UHFFFAOYSA-N 4-[4-(3,4-dimethylphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=CC=C(C)C(C)=C1 PBTGLAKUUZQCOX-UHFFFAOYSA-N 0.000 claims 1
- QDAJLYKEGAZDCN-UHFFFAOYSA-N 4-[4-(3,5-dichlorophenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 QDAJLYKEGAZDCN-UHFFFAOYSA-N 0.000 claims 1
- UTVLNIMGADRABB-UHFFFAOYSA-N 4-[4-(3,5-dimethylphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=CC(C)=CC(C)=C1 UTVLNIMGADRABB-UHFFFAOYSA-N 0.000 claims 1
- CKZORRHTHFTCKD-UHFFFAOYSA-N 4-[4-(3-chloro-2-fluorophenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=CC=CC(Cl)=C1F CKZORRHTHFTCKD-UHFFFAOYSA-N 0.000 claims 1
- ZWFGBNNTZMTMMJ-UHFFFAOYSA-N 4-[4-(3-chloro-4-fluorophenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=CC=C(F)C(Cl)=C1 ZWFGBNNTZMTMMJ-UHFFFAOYSA-N 0.000 claims 1
- GBVDDWYCRSVWRY-UHFFFAOYSA-N 4-[4-(3-chloro-5-fluorophenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=CC(F)=CC(Cl)=C1 GBVDDWYCRSVWRY-UHFFFAOYSA-N 0.000 claims 1
- MPCUATIVLODBLJ-UHFFFAOYSA-N 4-[4-(3-chloro-5-methoxyphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound COC1=CC(Cl)=CC(OC=2C=CC(=CC=2)N2C(NN=C2C)=O)=C1 MPCUATIVLODBLJ-UHFFFAOYSA-N 0.000 claims 1
- NAXHDKVFQMWPNI-UHFFFAOYSA-N 4-[4-(3-chlorophenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=CC=CC(Cl)=C1 NAXHDKVFQMWPNI-UHFFFAOYSA-N 0.000 claims 1
- IFWWFBSJDUPWOE-UHFFFAOYSA-N 4-[4-(3-ethoxyphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CCOC1=CC=CC(OC=2C=CC(=CC=2)N2C(NN=C2C)=O)=C1 IFWWFBSJDUPWOE-UHFFFAOYSA-N 0.000 claims 1
- MMYODIGMCPBBNL-UHFFFAOYSA-N 4-[4-(3-ethylphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CCC1=CC=CC(OC=2C=CC(=CC=2)N2C(NN=C2C)=O)=C1 MMYODIGMCPBBNL-UHFFFAOYSA-N 0.000 claims 1
- XSONJSCKMNUHGV-UHFFFAOYSA-N 4-[4-(3-methoxy-2-methylphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound COC1=CC=CC(OC=2C=CC(=CC=2)N2C(NN=C2C)=O)=C1C XSONJSCKMNUHGV-UHFFFAOYSA-N 0.000 claims 1
- FQCSOVIZRJNGQV-UHFFFAOYSA-N 4-[4-(3-methoxy-4-methylphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound C1=C(C)C(OC)=CC(OC=2C=CC(=CC=2)N2C(NN=C2C)=O)=C1 FQCSOVIZRJNGQV-UHFFFAOYSA-N 0.000 claims 1
- QRIPGYGUKLYSAX-UHFFFAOYSA-N 4-[4-(3-methoxyphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound COC1=CC=CC(OC=2C=CC(=CC=2)N2C(NN=C2C)=O)=C1 QRIPGYGUKLYSAX-UHFFFAOYSA-N 0.000 claims 1
- NBGXVOXMPPZUHR-UHFFFAOYSA-N 4-[4-(3-methylphenoxy)phenyl]-1H-1,2,4-triazol-5-one Chemical compound Cc1cccc(Oc2ccc(cc2)-n2cn[nH]c2=O)c1 NBGXVOXMPPZUHR-UHFFFAOYSA-N 0.000 claims 1
- QQEXZRDXMWHNMD-UHFFFAOYSA-N 4-[4-(4-chloro-3-methoxyphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound C1=C(Cl)C(OC)=CC(OC=2C=CC(=CC=2)N2C(NN=C2C)=O)=C1 QQEXZRDXMWHNMD-UHFFFAOYSA-N 0.000 claims 1
- GVUUMTPBEYAKJM-UHFFFAOYSA-N 4-[4-(4-fluoro-3-methoxyphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound C1=C(F)C(OC)=CC(OC=2C=CC(=CC=2)N2C(NN=C2C)=O)=C1 GVUUMTPBEYAKJM-UHFFFAOYSA-N 0.000 claims 1
- OFEZEJXVRWEDRO-UHFFFAOYSA-N 4-[4-(5-methoxy-2-methylphenoxy)phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound COC1=CC=C(C)C(OC=2C=CC(=CC=2)N2C(NN=C2C)=O)=C1 OFEZEJXVRWEDRO-UHFFFAOYSA-N 0.000 claims 1
- CXOVLXHTGLQPCU-UHFFFAOYSA-N 4-[4-[3-(dimethylamino)phenoxy]phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CN(C)C1=CC=CC(OC=2C=CC(=CC=2)N2C(NN=C2C)=O)=C1 CXOVLXHTGLQPCU-UHFFFAOYSA-N 0.000 claims 1
- PNAKZBIOKBEYPQ-UHFFFAOYSA-N 4-[4-[4-fluoro-3-(trifluoromethoxy)phenoxy]phenyl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1)=CC=C1OC1=CC=C(F)C(OC(F)(F)F)=C1 PNAKZBIOKBEYPQ-UHFFFAOYSA-N 0.000 claims 1
- KAFDWVNRZRPCEJ-UHFFFAOYSA-N 4-[6-(2,3-dimethylphenoxy)pyridin-3-yl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=N1)=CC=C1OC1=CC=CC(C)=C1C KAFDWVNRZRPCEJ-UHFFFAOYSA-N 0.000 claims 1
- NUTDLFJSTOHFNY-UHFFFAOYSA-N 4-[6-(3-ethoxyphenoxy)-5-methylpyridin-3-yl]-3-methyl-1H-1,2,4-triazol-5-one Chemical compound CCOc1cccc(Oc2ncc(cc2C)-n2c(C)n[nH]c2=O)c1 NUTDLFJSTOHFNY-UHFFFAOYSA-N 0.000 claims 1
- JPYJRVVTGDSUAV-UHFFFAOYSA-N 4-[6-(3-propan-2-ylphenoxy)pyridin-3-yl]-1H-1,2,4-triazol-5-one Chemical compound CC(C)c1cccc(Oc2ccc(cn2)-n2cn[nH]c2=O)c1 JPYJRVVTGDSUAV-UHFFFAOYSA-N 0.000 claims 1
- GADKJUHCHUWHKA-UHFFFAOYSA-N 4-[6-[(3,3-diethyl-1h-2-benzofuran-5-yl)oxy]pyridin-3-yl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound C1=C2C(CC)(CC)OCC2=CC=C1OC(N=C1)=CC=C1N1C(C)=NNC1=O GADKJUHCHUWHKA-UHFFFAOYSA-N 0.000 claims 1
- IRMDVYGLPAWMSG-UHFFFAOYSA-N 4-[6-[(3,3-dimethyl-2h-1-benzofuran-4-yl)oxy]-5-methylpyridin-3-yl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=C1C)=CN=C1OC1=CC=CC2=C1C(C)(C)CO2 IRMDVYGLPAWMSG-UHFFFAOYSA-N 0.000 claims 1
- FWBDVGGUCXZCAY-UHFFFAOYSA-N 4-[6-[(3,3-dimethyl-2h-1-benzofuran-4-yl)oxy]pyridin-3-yl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=N1)=CC=C1OC1=CC=CC2=C1C(C)(C)CO2 FWBDVGGUCXZCAY-UHFFFAOYSA-N 0.000 claims 1
- RZHPRAFVXFPVPT-UHFFFAOYSA-N 4-[6-[(3-tert-butyl-1,3-dihydro-2-benzofuran-4-yl)oxy]pyridin-3-yl]-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C(C=N1)=CC=C1OC1=CC=CC2=C1C(C(C)(C)C)OC2 RZHPRAFVXFPVPT-UHFFFAOYSA-N 0.000 claims 1
- 206010011878 Deafness Diseases 0.000 claims 1
- 208000001914 Fragile X syndrome Diseases 0.000 claims 1
- 208000009205 Tinnitus Diseases 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 230000010370 hearing loss Effects 0.000 claims 1
- 231100000888 hearing loss Toxicity 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 231100000886 tinnitus Toxicity 0.000 claims 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1209019.7 | 2012-05-22 | ||
| GBGB1209020.5A GB201209020D0 (en) | 2012-05-22 | 2012-05-22 | Novel compounds |
| GB1209013.0 | 2012-05-22 | ||
| GB1209020.5 | 2012-05-22 | ||
| GBGB1209013.0A GB201209013D0 (en) | 2012-05-22 | 2012-05-22 | Novel compounds |
| GBGB1209019.7A GB201209019D0 (en) | 2012-05-22 | 2012-05-22 | Novel compounds |
| US201261702337P | 2012-09-18 | 2012-09-18 | |
| US61/702,337 | 2012-09-18 | ||
| GB1222393.9 | 2012-12-12 | ||
| GBGB1222393.9A GB201222393D0 (en) | 2012-12-12 | 2012-12-12 | Novel compounds |
| PCT/GB2013/051347 WO2013175215A1 (en) | 2012-05-22 | 2013-05-22 | Triazoles as kv3 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015520764A JP2015520764A (ja) | 2015-07-23 |
| JP2015520764A5 true JP2015520764A5 (enExample) | 2017-03-23 |
| JP6240667B2 JP6240667B2 (ja) | 2017-11-29 |
Family
ID=49623224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015513270A Expired - Fee Related JP6240667B2 (ja) | 2012-05-22 | 2013-05-22 | Ｋｖ３阻害剤としてのトリアゾール |
Country Status (6)
| Country | Link |
|---|---|
| US (4) | US9422252B2 (enExample) |
| EP (1) | EP2852589B1 (enExample) |
| JP (1) | JP6240667B2 (enExample) |
| CN (1) | CN104334547B (enExample) |
| BR (1) | BR112014028991A2 (enExample) |
| WO (1) | WO2013175215A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5788404B2 (ja) | 2009-12-11 | 2015-09-30 | アウトイフオンイ トヘラペウトイクス リミテッド | イミダゾリジンジオン誘導体 |
| US9193704B2 (en) | 2011-06-07 | 2015-11-24 | Autifony Therapeutics Limited | Hydantoin derivatives as KV3 inhibitors |
| BR112014027644A2 (pt) * | 2012-05-09 | 2017-06-27 | Bayer Cropscience Ag | 5-halogenopirazol-indanil-carboxamidas |
| EP2852588B8 (en) * | 2012-05-22 | 2018-01-10 | Autifony Therapeutics Limited | Hydantoin derivatives as kv3 inhibitors |
| US9422252B2 (en) | 2012-05-22 | 2016-08-23 | Autifony Therapeutics Limited | Triazoles as Kv3 inhibitors |
| WO2015095442A1 (en) * | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | Piperidinyloxy lactone orexin receptor antagonists |
| GB201521751D0 (en) | 2015-12-10 | 2016-01-27 | Autifony Therapeutics Ltd | Novel uses |
| GB201613163D0 (en) | 2016-07-29 | 2016-09-14 | Autifony Therapeutics Ltd | Novel compounds |
| WO2018109484A1 (en) | 2016-12-16 | 2018-06-21 | Autifony Therapeutics Limited | Hydantoin modulators of kv3 channels |
| SG11202003879RA (en) | 2017-10-30 | 2020-05-28 | Neuropore Therapies Inc | Substituted phenyl sulfonyl phenyl triazole thiones and uses thereof |
| WO2019246454A1 (en) * | 2018-06-20 | 2019-12-26 | Neuropore Therapies, Inc. | Method of treating a condition associated with neurodegeneration using inhibitors of oat3 |
| US12358901B2 (en) | 2018-10-16 | 2025-07-15 | Autifony Therapeutics Limited | KV3 modulators |
| TWI827706B (zh) | 2018-10-16 | 2024-01-01 | 英商奧堤凡尼治療股份有限公司 | 新穎化合物 |
| AR116898A1 (es) * | 2018-10-30 | 2021-06-23 | H Lundbeck As | DERIVADOS DE ARILSULFONILPIRROLCARBOXAMIDA COMO ACTIVADORES DE CANALES DE POTASIO Kv3 |
| SG11202104374WA (en) * | 2018-11-30 | 2021-05-28 | Otsuka Pharma Co Ltd | Heterocyclic compounds for the treatment of epilepsy |
| JP7522203B2 (ja) | 2020-02-06 | 2024-07-24 | アウトイフオンイ トヘラペウトイクス リミテッド | Ｋｖ３モジュレーター |
| US20240327406A1 (en) | 2021-08-10 | 2024-10-03 | Autifony Therapeutics Limited | Potassium channel modulators |
| EP4630117A1 (en) | 2022-12-06 | 2025-10-15 | Autifony Therapeutics Limited | Compounds for the treatment of centra nervous system disorders |
Family Cites Families (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3015090A1 (de) | 1980-04-19 | 1981-10-22 | Basf Ag, 6700 Ludwigshafen | ]-(trihalogenmethyl-sulfenyl)-4-aryl-1,2,4-triazolidin-5-one, verfahren zu ihrer herstellung, diese enthaltende fungizide und verfahren zur bekaempfung von pilzen mit diesen verbindungen |
| DE3133405A1 (de) | 1981-08-24 | 1983-03-10 | Basf Ag, 6700 Ludwigshafen | 1-(trihalogenmethyl-sulfenyl)-4-aryl-1,2,4-triazolidin-5-one und diese enthaltende fungizide |
| US4675403A (en) | 1985-10-16 | 1987-06-23 | American Home Products Corporation | 3-Aminoalkyl derivatives of 5,5-disubstituted hydantoins with psychotropic activity |
| JP2514945B2 (ja) | 1987-02-05 | 1996-07-10 | 三井石油化学工業株式会社 | 芳香族アミン誘導体 |
| DE3810848A1 (de) | 1988-03-30 | 1989-10-19 | Boehringer Ingelheim Kg | Neue 2,3,4-substituierte imidazole und 3,4,5-substituierte 1,2,4-triazole, ihre herstellung und verwendung |
| DE3836175A1 (de) | 1988-10-24 | 1990-05-03 | Bayer Ag | Fluor enthaltende phenole |
| WO1991004027A1 (en) | 1989-09-15 | 1991-04-04 | Pfizer Inc. | New n-aryl and n-heteroarylamide and urea derivatives as inhibitors of acyl coenzyme a: cholesterol acyl transferase (acat) |
| US5362878A (en) | 1991-03-21 | 1994-11-08 | Pfizer Inc. | Intermediates for making N-aryl and N-heteroarylamide and urea derivatives as inhibitors of acyl coenzyme A: cholesterol acyl transferase (ACAT) |
| US6002016A (en) | 1991-12-20 | 1999-12-14 | Rhone-Poulenc Agrochimie | Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones |
| DK123493D0 (da) | 1993-11-01 | 1993-11-01 | Lundbeck & Co As H | Compounds |
| US5607932A (en) | 1994-07-12 | 1997-03-04 | Janssen Pharmaceutica N.V. | Heterocyclic derivatives of azolones |
| EP0825992A1 (en) | 1995-05-17 | 1998-03-04 | E.I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
| WO1996036229A1 (en) | 1995-05-17 | 1996-11-21 | E.I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
| PL324291A1 (en) | 1995-06-20 | 1998-05-11 | Du Pont | Anthropodicidal and fungicidal cyclic amides |
| BR9711816A (pt) | 1996-08-01 | 1999-08-31 | Du Pont | Composto, composição fungicida, método para controlar doenças de plantas causadas pelos agentes patogênicos f·ngicos de plantas, composição artropodicida e método para controlar artrópodes. |
| US5728834A (en) | 1996-11-14 | 1998-03-17 | Wyckoff Chemical Company, Inc. | Process for preparation of 4-aryl-1,2,4-triazol-3-ones |
| WO1998023155A1 (en) | 1996-11-26 | 1998-06-04 | E.I. Du Pont De Nemours And Company | Arthropodicidal and fungicidal cyclic amides |
| KR20000057254A (ko) | 1996-11-26 | 2000-09-15 | 메리 이. 보울러 | 메틸 치환된 살진균제 및 살절지동물제 |
| AU6040398A (en) | 1997-01-30 | 1998-08-25 | E.I. Du Pont De Nemours And Company | Fungicidal compositions |
| JP4171549B2 (ja) | 1998-01-28 | 2008-10-22 | 大正製薬株式会社 | 含フッ素アミノ酸誘導体 |
| JP4194715B2 (ja) | 1998-08-31 | 2008-12-10 | 大正製薬株式会社 | ６−フルオロビシクロ［３．１．０］ヘキサン誘導体 |
| JP2000072731A (ja) | 1998-08-31 | 2000-03-07 | Taisho Pharmaceut Co Ltd | ４−置換−２−アミノビシクロ［３．１．０］ヘキサン−２，６−ジカルボン酸誘導体及び製薬用組成物 |
| BR0012697A (pt) | 1999-07-23 | 2002-04-09 | Shionogi & Co | Inibidores da diferenciação de th2 |
| KR20030009416A (ko) | 2000-04-04 | 2003-01-29 | 시오노기세이야쿠가부시키가이샤 | 고지용성 약물을 함유하는 유성 조성물 |
| FR2807434B1 (fr) | 2000-04-05 | 2002-10-18 | Hoechst Marion Roussel Inc | Nouveaux derives de la 1,2,3,4-tetrahydroisoquinoleine, leur procede de preparation et leur application comme fongicides |
| AU2001244610A1 (en) | 2000-04-05 | 2001-10-23 | Shionogi And Co., Ltd. | Oil-in-water microemulsions containing tricyclic compounds or preconcentrates thereof |
| FR2812633A1 (fr) | 2000-08-04 | 2002-02-08 | Aventis Cropscience Sa | Derives de phenyl(thio)urees et phenyl(thio)carbamates fongicides |
| AU2002354410A1 (en) | 2001-12-05 | 2003-06-17 | Japan Tobacco Inc. | Triazole compound and medicinal use thereof |
| AU2003210916B9 (en) | 2002-02-07 | 2008-12-18 | The Curators Of The University Of Missouri | Opioid receptor active 4-(3-hydroxyphenyl) or 4-(3-alkoxyphenyl)-1,2,4-triazole compounds |
| AU2003206021A1 (en) | 2003-02-20 | 2004-09-09 | Ranbaxy Laboratories Limited | Derivatives of azasugars as anticancer agents |
| MXPA05011523A (es) | 2003-04-30 | 2006-01-23 | Inst For Pharm Discovery Inc | Heteroarilos sustituidos como inhibidores de proteinas de tirosina fosfatasas. |
| WO2005000309A2 (en) | 2003-06-27 | 2005-01-06 | Ionix Pharmaceuticals Limited | Chemical compounds |
| GB0325175D0 (en) | 2003-10-28 | 2003-12-03 | Novartis Ag | Organic compounds |
| US7256208B2 (en) | 2003-11-13 | 2007-08-14 | Bristol-Myers Squibb Company | Monocyclic N-Aryl hydantoin modulators of androgen receptor function |
| SI1751131T1 (sl) * | 2004-03-10 | 2009-04-30 | Janssen Pharmaceutica Nv | MTP inhibirajoči aril piperidini ali piperazini substituirani s 5-členskimi heterocikli |
| US20060211697A1 (en) | 2004-12-08 | 2006-09-21 | Liren Huang | 2-(2 Or 4-substituted aryloxy)-phenol derivatives as antibacterial agents |
| AR052342A1 (es) | 2004-12-21 | 2007-03-14 | Janssen Pharmaceutica Nv | Derivados sustituidos de triazolona,tetrazolona e imidazolona con actividad selectiva antagonista de alfa2c-adenoreceptores |
| NZ564223A (en) | 2005-05-13 | 2011-03-31 | Univ California | Diarylhydantoin compounds for treating hormone refractory prostate cancer |
| US7709517B2 (en) | 2005-05-13 | 2010-05-04 | The Regents Of The University Of California | Diarylhydantoin compounds |
| SI2656842T1 (sl) | 2006-03-27 | 2016-10-28 | The Regents Of The University Of California | Modulator androgenih receptorjev za zdravljenje raka prostate in bolezni, povezanih z androgenimi receptorji |
| WO2007127010A2 (en) | 2006-03-29 | 2007-11-08 | The Regents Of The University Of California | Diarylthiohydantoin compounds |
| CN101600689A (zh) * | 2006-12-15 | 2009-12-09 | Irm责任有限公司 | 作为大麻素受体1活性抑制剂的化合物和组合物 |
| WO2008131276A1 (en) | 2007-04-20 | 2008-10-30 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
| EP2242747A1 (de) | 2008-02-07 | 2010-10-27 | Sanofi-Aventis | Substituierte imidazolidin-2,4-dione, verfahren zu ihrer herstellung, diese verbindungen enthaltende arzneimittel und ihre verwendung |
| EP2356111A1 (en) | 2008-11-10 | 2011-08-17 | Schering Corporation | Compounds for the treatment of inflammatory disorders |
| CN102256968A (zh) | 2008-12-22 | 2011-11-23 | 弗·哈夫曼-拉罗切有限公司 | 杂环抗病毒化合物 |
| JP5788404B2 (ja) | 2009-12-11 | 2015-09-30 | アウトイフオンイ トヘラペウトイクス リミテッド | イミダゾリジンジオン誘導体 |
| CA2780526A1 (en) | 2009-12-14 | 2011-06-23 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| EP2616443A1 (en) | 2010-09-14 | 2013-07-24 | Exelixis, Inc. | Phtalazine derivatives as jak1 inhibitors |
| EP2649066B1 (en) * | 2010-12-06 | 2015-10-21 | Autifony Therapeutics Limited | Hydantoin derivatives useful as kv3 inhibitors |
| US9193704B2 (en) * | 2011-06-07 | 2015-11-24 | Autifony Therapeutics Limited | Hydantoin derivatives as KV3 inhibitors |
| GB201209986D0 (en) | 2012-06-06 | 2012-07-18 | Autifony Therapeutics Ltd | Novel compounds |
| AU2012349847B2 (en) | 2011-12-06 | 2017-02-16 | Autifony Therapeutics Limited | Hydantoin derivatives useful as Kv3 inhibitors |
| US9422252B2 (en) | 2012-05-22 | 2016-08-23 | Autifony Therapeutics Limited | Triazoles as Kv3 inhibitors |
| EP2852588B8 (en) | 2012-05-22 | 2018-01-10 | Autifony Therapeutics Limited | Hydantoin derivatives as kv3 inhibitors |
| WO2013182851A1 (en) | 2012-06-06 | 2013-12-12 | Autifony Therapeutics Limited | Prophylaxis or treatment of diseases where a modulator of kv3.3 channels is required |
-
2013
- 2013-05-22 US US14/403,048 patent/US9422252B2/en active Active
- 2013-05-22 EP EP13725447.0A patent/EP2852589B1/en active Active
- 2013-05-22 WO PCT/GB2013/051347 patent/WO2013175215A1/en not_active Ceased
- 2013-05-22 BR BR112014028991A patent/BR112014028991A2/pt not_active IP Right Cessation
- 2013-05-22 CN CN201380026338.8A patent/CN104334547B/zh not_active Expired - Fee Related
- 2013-05-22 JP JP2015513270A patent/JP6240667B2/ja not_active Expired - Fee Related
-
2016
- 2016-07-12 US US15/208,329 patent/US10160730B2/en active Active
-
2018
- 2018-11-06 US US16/181,864 patent/US10611735B2/en active Active
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2020
- 2020-02-07 US US16/785,083 patent/US11180461B2/en active Active
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