JP2014516073A5 - - Google Patents
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- Publication number
- JP2014516073A5 JP2014516073A5 JP2014514148A JP2014514148A JP2014516073A5 JP 2014516073 A5 JP2014516073 A5 JP 2014516073A5 JP 2014514148 A JP2014514148 A JP 2014514148A JP 2014514148 A JP2014514148 A JP 2014514148A JP 2014516073 A5 JP2014516073 A5 JP 2014516073A5
- Authority
- JP
- Japan
- Prior art keywords
- imidazolidine
- dione
- methyl
- oxy
- ethyl
- 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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- DNMGPGWXOMGJFN-UHFFFAOYSA-N spiro[1h-2-benzofuran-3,1'-cyclopentane]-5-ol Chemical compound C12=CC(O)=CC=C2COC21CCCC2 DNMGPGWXOMGJFN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 44
- 125000005843 halogen group Chemical group 0.000 claims 32
- 150000001875 compounds Chemical class 0.000 claims 28
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000006413 ring segment Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- 208000016354 hearing loss disease Diseases 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- RFDFIGVUTNWOAX-IVAFLUGOSA-N (5r)-3-[2-[(3-tert-butyl-1,3-dihydro-2-benzofuran-5-yl)oxy]pyrimidin-5-yl]-5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC2C(C)(C)C)C2=C1 RFDFIGVUTNWOAX-IVAFLUGOSA-N 0.000 claims 4
- HEDYZGNKUJMEMM-LEQGEALCSA-N (5r)-3-[6-[(3-tert-butyl-1,3-dihydro-2-benzofuran-5-yl)oxy]pyridin-3-yl]-5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC2C(C)(C)C)C2=C1 HEDYZGNKUJMEMM-LEQGEALCSA-N 0.000 claims 4
- SKXPEZRPXUSJHY-IKJXHCRLSA-N (5r)-5-ethyl-3-[2-[[3-methyl-3-(trifluoromethyl)-1h-2-benzofuran-5-yl]oxy]pyrimidin-5-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@@H](CC)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC2(C)C(F)(F)F)C2=C1 SKXPEZRPXUSJHY-IKJXHCRLSA-N 0.000 claims 4
- XYISZEPLGKRZAR-NYRJJRHWSA-N (5r)-5-ethyl-3-[6-[[3-methyl-3-(trifluoromethyl)-1h-2-benzofuran-5-yl]oxy]pyridin-3-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@@H](CC)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC2(C)C(F)(F)F)C2=C1 XYISZEPLGKRZAR-NYRJJRHWSA-N 0.000 claims 4
- OWUGDYTUCLRMTK-MRTLOADZSA-N (5r)-5-ethyl-5-methyl-3-[2-[[3-methyl-3-(trifluoromethyl)-1h-2-benzofuran-5-yl]oxy]pyrimidin-5-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC2(C)C(F)(F)F)C2=C1 OWUGDYTUCLRMTK-MRTLOADZSA-N 0.000 claims 4
- RGQNUZIWDODFPM-VQCQRNETSA-N (5r)-5-ethyl-5-methyl-3-[5-methyl-6-[[3-methyl-3-(trifluoromethyl)-1h-2-benzofuran-5-yl]oxy]pyridin-3-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=C1C)=CN=C1OC1=CC=C(COC2(C)C(F)(F)F)C2=C1 RGQNUZIWDODFPM-VQCQRNETSA-N 0.000 claims 4
- XHBQTBHBSLUMOU-FIWHBWSRSA-N (5r)-5-ethyl-5-methyl-3-[6-[[3-methyl-3-(trifluoromethyl)-1h-2-benzofuran-5-yl]oxy]pyridin-3-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC2(C)C(F)(F)F)C2=C1 XHBQTBHBSLUMOU-FIWHBWSRSA-N 0.000 claims 4
- DHHSJNRTOWLSOO-UHFFFAOYSA-N 3-[2-[(3-tert-butyl-1,3-dihydro-2-benzofuran-5-yl)oxy]pyrimidin-5-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound C1=C2C(C(C)(C)C)OCC2=CC=C1OC(N=C1)=NC=C1N1C(=O)NC(C)(C)C1=O DHHSJNRTOWLSOO-UHFFFAOYSA-N 0.000 claims 4
- BLJABDKRDIIYLJ-UHFFFAOYSA-N 3-[6-[(3-tert-butyl-1,3-dihydro-2-benzofuran-5-yl)oxy]pyridin-3-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound C1=C2C(C(C)(C)C)OCC2=CC=C1OC(N=C1)=CC=C1N1C(=O)NC(C)(C)C1=O BLJABDKRDIIYLJ-UHFFFAOYSA-N 0.000 claims 4
- PFWPHOLELOXFFV-UHFFFAOYSA-N 5,5-dimethyl-3-[2-[[3-methyl-3-(trifluoromethyl)-1h-2-benzofuran-5-yl]oxy]pyrimidin-5-yl]imidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC2(C)C(F)(F)F)C2=C1 PFWPHOLELOXFFV-UHFFFAOYSA-N 0.000 claims 4
- NKMHTNGMJVHRTM-UHFFFAOYSA-N 5,5-dimethyl-3-[6-[[3-methyl-3-(trifluoromethyl)-1h-2-benzofuran-5-yl]oxy]pyridin-3-yl]imidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC2(C)C(F)(F)F)C2=C1 NKMHTNGMJVHRTM-UHFFFAOYSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- -1 1,3-Dihydro-2-benzofuran-5-yloxy Chemical group 0.000 claims 3
- 206010011878 Deafness Diseases 0.000 claims 3
- 208000009205 Tinnitus Diseases 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 231100000886 tinnitus Toxicity 0.000 claims 3
- NGNJDTAVMXCKSV-HXUWFJFHSA-N (5r)-3-[2-[(3,3-dimethyl-1h-2-benzofuran-5-yl)oxy]pyrimidin-5-yl]-5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC2(C)C)C2=C1 NGNJDTAVMXCKSV-HXUWFJFHSA-N 0.000 claims 2
- PXGUUSBQQRYVGW-FBLFFUNLSA-N (5r)-3-[2-[(3-cyclopropyl-1,3-dihydro-2-benzofuran-5-yl)oxy]pyrimidin-5-yl]-5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC2C3CC3)C2=C1 PXGUUSBQQRYVGW-FBLFFUNLSA-N 0.000 claims 2
- GFTJIMPCCPRHLU-OAQYLSRUSA-N (5r)-3-[2-[(4,4-dimethyl-1,3-dihydroisochromen-6-yl)oxy]pyrimidin-5-yl]-5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COCC2(C)C)C2=C1 GFTJIMPCCPRHLU-OAQYLSRUSA-N 0.000 claims 2
- YLINUWFWUKIGBS-JOCHJYFZSA-N (5r)-3-[6-[(3,3-dimethyl-1h-2-benzofuran-5-yl)oxy]-5-methylpyridin-3-yl]-5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=C1C)=CN=C1OC1=CC=C(COC2(C)C)C2=C1 YLINUWFWUKIGBS-JOCHJYFZSA-N 0.000 claims 2
- SHSPZEJVBTZRAQ-OAQYLSRUSA-N (5r)-3-[6-[(3,3-dimethyl-1h-2-benzofuran-5-yl)oxy]pyridin-3-yl]-5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC2(C)C)C2=C1 SHSPZEJVBTZRAQ-OAQYLSRUSA-N 0.000 claims 2
- OWZHSHKAPQCKHB-MRXNPFEDSA-N (5r)-3-[6-[(3,3-dimethyl-1h-2-benzofuran-5-yl)oxy]pyridin-3-yl]-5-ethylimidazolidine-2,4-dione Chemical compound O=C1[C@@H](CC)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC2(C)C)C2=C1 OWZHSHKAPQCKHB-MRXNPFEDSA-N 0.000 claims 2
- DLJGXIMVMXQVOL-AVKWCDSFSA-N (5r)-3-[6-[(3-cyclopropyl-1,3-dihydro-2-benzofuran-5-yl)oxy]pyridin-3-yl]-5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC2C3CC3)C2=C1 DLJGXIMVMXQVOL-AVKWCDSFSA-N 0.000 claims 2
- ODYDLICXEYJNPP-JOCHJYFZSA-N (5r)-3-[6-[(4,4-dimethyl-1,3-dihydroisochromen-6-yl)oxy]pyridin-3-yl]-5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COCC2(C)C)C2=C1 ODYDLICXEYJNPP-JOCHJYFZSA-N 0.000 claims 2
- LSOZZXGDMKCFRV-MRXNPFEDSA-N (5r)-5-ethyl-3-(2-spiro[1h-2-benzofuran-3,1'-cyclobutane]-5-yloxypyrimidin-5-yl)imidazolidine-2,4-dione Chemical compound O=C1[C@@H](CC)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC23CCC3)C2=C1 LSOZZXGDMKCFRV-MRXNPFEDSA-N 0.000 claims 2
- GANVXLQPVDRZDP-QGZVFWFLSA-N (5r)-5-ethyl-3-(6-spiro[1h-2-benzofuran-3,1'-cyclobutane]-5-yloxypyridin-3-yl)imidazolidine-2,4-dione Chemical compound O=C1[C@@H](CC)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC23CCC3)C2=C1 GANVXLQPVDRZDP-QGZVFWFLSA-N 0.000 claims 2
- KUSCHUIKPGUDDF-OTOKDRCRSA-N (5r)-5-ethyl-3-[2-[(3-ethyl-1,3-dihydro-2-benzofuran-5-yl)oxy]pyrimidin-5-yl]-5-methylimidazolidine-2,4-dione Chemical compound C1=C2C(CC)OCC2=CC=C1OC(N=C1)=NC=C1N1C(=O)N[C@](C)(CC)C1=O KUSCHUIKPGUDDF-OTOKDRCRSA-N 0.000 claims 2
- VHCQGDDHMGSPCJ-FBLFFUNLSA-N (5r)-5-ethyl-3-[6-[(3-ethyl-1,3-dihydro-2-benzofuran-5-yl)oxy]pyridin-3-yl]-5-methylimidazolidine-2,4-dione Chemical compound C1=C2C(CC)OCC2=CC=C1OC(N=C1)=CC=C1N1C(=O)N[C@](C)(CC)C1=O VHCQGDDHMGSPCJ-FBLFFUNLSA-N 0.000 claims 2
- ACUNKDPNYHBFML-JOCHJYFZSA-N (5r)-5-ethyl-5-methyl-3-(5-methyl-6-spiro[1h-2-benzofuran-3,1'-cyclobutane]-5-yloxypyridin-3-yl)imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=C1C)=CN=C1OC1=CC=C(COC23CCC3)C2=C1 ACUNKDPNYHBFML-JOCHJYFZSA-N 0.000 claims 2
- IHUKOBHPRYNGAA-OAQYLSRUSA-N (5r)-5-ethyl-5-methyl-3-(6-spiro[1h-2-benzofuran-3,1'-cyclobutane]-5-yloxypyridin-3-yl)imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC23CCC3)C2=C1 IHUKOBHPRYNGAA-OAQYLSRUSA-N 0.000 claims 2
- SLCNIZVVOKLZCY-XPKAQORNSA-N (5r)-5-ethyl-5-methyl-3-[2-[[3-(trifluoromethyl)-1,3-dihydro-2-benzofuran-5-yl]oxy]pyrimidin-5-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC2C(F)(F)F)C2=C1 SLCNIZVVOKLZCY-XPKAQORNSA-N 0.000 claims 2
- DLKGQKBQEFLFBQ-OTOKDRCRSA-N (5r)-5-ethyl-5-methyl-3-[5-methyl-6-[[3-(trifluoromethyl)-1,3-dihydro-2-benzofuran-5-yl]oxy]pyridin-3-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=C1C)=CN=C1OC1=CC=C(COC2C(F)(F)F)C2=C1 DLKGQKBQEFLFBQ-OTOKDRCRSA-N 0.000 claims 2
- SNKUAWZFNNOCOP-LRTDYKAYSA-N (5r)-5-ethyl-5-methyl-3-[6-[[3-(trifluoromethyl)-1,3-dihydro-2-benzofuran-5-yl]oxy]pyridin-3-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC2C(F)(F)F)C2=C1 SNKUAWZFNNOCOP-LRTDYKAYSA-N 0.000 claims 2
- GZJTXYMLKLJLEO-UHFFFAOYSA-N 3-[2-[(3,3-dimethyl-1h-2-benzofuran-5-yl)oxy]pyrimidin-5-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC2(C)C)C2=C1 GZJTXYMLKLJLEO-UHFFFAOYSA-N 0.000 claims 2
- PXHKOKCNQDWTHM-UHFFFAOYSA-N 3-[2-[(3-cyclopropyl-1,3-dihydro-2-benzofuran-5-yl)oxy]pyrimidin-5-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC2C3CC3)C2=C1 PXHKOKCNQDWTHM-UHFFFAOYSA-N 0.000 claims 2
- YZAKZINCORTXJE-UHFFFAOYSA-N 3-[2-[(3-ethyl-1,3-dihydro-2-benzofuran-5-yl)oxy]pyrimidin-5-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound C1=C2C(CC)OCC2=CC=C1OC(N=C1)=NC=C1N1C(=O)NC(C)(C)C1=O YZAKZINCORTXJE-UHFFFAOYSA-N 0.000 claims 2
- DCQVJUJQVJIWPU-UHFFFAOYSA-N 3-[2-[(4,4-dimethyl-1,3-dihydroisochromen-6-yl)oxy]pyrimidin-5-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COCC2(C)C)C2=C1 DCQVJUJQVJIWPU-UHFFFAOYSA-N 0.000 claims 2
- CQVXHNZMCWCHQE-UHFFFAOYSA-N 3-[6-[(3-cyclopropyl-1,3-dihydro-2-benzofuran-5-yl)oxy]pyridin-3-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC2C3CC3)C2=C1 CQVXHNZMCWCHQE-UHFFFAOYSA-N 0.000 claims 2
- YFHJRRXHMHBQPT-UHFFFAOYSA-N 5,5-dimethyl-3-(2-spiro[1h-2-benzofuran-3,1'-cyclobutane]-5-yloxypyrimidin-5-yl)imidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC23CCC3)C2=C1 YFHJRRXHMHBQPT-UHFFFAOYSA-N 0.000 claims 2
- ABBBYWZTLYAUOM-UHFFFAOYSA-N 5,5-dimethyl-3-(6-spiro[1h-2-benzofuran-3,1'-cyclobutane]-5-yloxypyridin-3-yl)imidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC23CCC3)C2=C1 ABBBYWZTLYAUOM-UHFFFAOYSA-N 0.000 claims 2
- JVLHFRFFZBGGJI-UHFFFAOYSA-N 5,5-dimethyl-3-[2-[[3-(trifluoromethyl)-1,3-dihydro-2-benzofuran-5-yl]oxy]pyrimidin-5-yl]imidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC2C(F)(F)F)C2=C1 JVLHFRFFZBGGJI-UHFFFAOYSA-N 0.000 claims 2
- AARKGPHPYSFFLO-UHFFFAOYSA-N 5,5-dimethyl-3-[5-methyl-6-[[3-(trifluoromethyl)-1,3-dihydro-2-benzofuran-5-yl]oxy]pyridin-3-yl]imidazolidine-2,4-dione Chemical compound C=1N=C(OC=2C=C3C(OCC3=CC=2)C(F)(F)F)C(C)=CC=1N1C(=O)NC(C)(C)C1=O AARKGPHPYSFFLO-UHFFFAOYSA-N 0.000 claims 2
- HYKBZOJSLFUHPQ-UHFFFAOYSA-N 5,5-dimethyl-3-[6-[[3-(trifluoromethyl)-1,3-dihydro-2-benzofuran-5-yl]oxy]pyridin-3-yl]imidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC2C(F)(F)F)C2=C1 HYKBZOJSLFUHPQ-UHFFFAOYSA-N 0.000 claims 2
- 206010003591 Ataxia Diseases 0.000 claims 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 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
- 231100000895 deafness Toxicity 0.000 claims 2
- 229910052805 deuterium Inorganic materials 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- KWWAUFZMGKQKDI-OAQYLSRUSA-N (5r)-3-[2-[(3,3-diethyl-1h-2-benzofuran-5-yl)oxy]pyrimidin-5-yl]-5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC2(CC)CC)C2=C1 KWWAUFZMGKQKDI-OAQYLSRUSA-N 0.000 claims 1
- VGUVXVCVUZURSD-HXUWFJFHSA-N (5r)-3-[2-[(3,3-dimethyl-2h-1-benzofuran-5-yl)oxy]pyrimidin-5-yl]-5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(OCC2(C)C)C2=C1 VGUVXVCVUZURSD-HXUWFJFHSA-N 0.000 claims 1
- UTNPAJXEQYBRPF-JOCHJYFZSA-N (5r)-3-[4-[(3,3-dimethyl-1h-2-benzofuran-5-yl)oxy]phenyl]-5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=C1)=CC=C1OC1=CC=C(COC2(C)C)C2=C1 UTNPAJXEQYBRPF-JOCHJYFZSA-N 0.000 claims 1
- QOHXMTCRAKZKAS-JOCHJYFZSA-N (5r)-3-[6-[(3,3-diethyl-1h-2-benzofuran-5-yl)oxy]pyridin-3-yl]-5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC2(CC)CC)C2=C1 QOHXMTCRAKZKAS-JOCHJYFZSA-N 0.000 claims 1
- AIKOGQLXSXLSOR-OAQYLSRUSA-N (5r)-3-[6-[(3,3-dimethyl-2h-1-benzofuran-5-yl)oxy]pyridin-3-yl]-5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(OCC2(C)C)C2=C1 AIKOGQLXSXLSOR-OAQYLSRUSA-N 0.000 claims 1
- KAAGFQARPRFVCV-OAHLLOKOSA-N (5r)-3-[6-[(3,3-dimethyl-2h-1-benzofuran-5-yl)oxy]pyridin-3-yl]-5-ethylimidazolidine-2,4-dione Chemical compound O=C1[C@@H](CC)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(OCC2(C)C)C2=C1 KAAGFQARPRFVCV-OAHLLOKOSA-N 0.000 claims 1
- MJACQPDTJQZOIH-HXUWFJFHSA-N (5r)-5-ethyl-5-methyl-3-(2-spiro[1h-2-benzofuran-3,1'-cyclobutane]-5-yloxypyrimidin-5-yl)imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC23CCC3)C2=C1 MJACQPDTJQZOIH-HXUWFJFHSA-N 0.000 claims 1
- NCCOXRAOCBVOBG-OAQYLSRUSA-N (5r)-5-ethyl-5-methyl-3-(2-spiro[1h-2-benzofuran-3,1'-cyclopentane]-5-yloxypyrimidin-5-yl)imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC23CCCC3)C2=C1 NCCOXRAOCBVOBG-OAQYLSRUSA-N 0.000 claims 1
- NJSFHPVYLAMHCN-JOCHJYFZSA-N (5r)-5-ethyl-5-methyl-3-(6-spiro[1h-2-benzofuran-3,1'-cyclopentane]-5-yloxypyridin-3-yl)imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC23CCCC3)C2=C1 NJSFHPVYLAMHCN-JOCHJYFZSA-N 0.000 claims 1
- BMNGAIYZLTVYTC-UHFFFAOYSA-N 3,3-diethyl-1h-2-benzofuran-5-ol Chemical compound C1=C(O)C=C2C(CC)(CC)OCC2=C1 BMNGAIYZLTVYTC-UHFFFAOYSA-N 0.000 claims 1
- STGGENRPHBLBFO-UHFFFAOYSA-N 3,3-dimethyl-1h-2-benzofuran-5-ol Chemical compound C1=C(O)C=C2C(C)(C)OCC2=C1 STGGENRPHBLBFO-UHFFFAOYSA-N 0.000 claims 1
- UBRFCYQKOPCZLL-UHFFFAOYSA-N 3-(trifluoromethyl)-1,3-dihydro-2-benzofuran-5-ol Chemical compound OC1=CC=C2COC(C(F)(F)F)C2=C1 UBRFCYQKOPCZLL-UHFFFAOYSA-N 0.000 claims 1
- HLDVEENPMLMRSM-UHFFFAOYSA-N 3-[2-[(3,3-diethyl-1h-2-benzofuran-5-yl)oxy]pyrimidin-5-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound C1=C2C(CC)(CC)OCC2=CC=C1OC(N=C1)=NC=C1N1C(=O)NC(C)(C)C1=O HLDVEENPMLMRSM-UHFFFAOYSA-N 0.000 claims 1
- UTOYMVFQCHDTBV-UHFFFAOYSA-N 3-[2-[(3,3-dimethyl-2h-1-benzofuran-5-yl)oxy]pyrimidin-5-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound C1=C2C(C)(C)COC2=CC=C1OC(N=C1)=NC=C1N1C(=O)NC(C)(C)C1=O UTOYMVFQCHDTBV-UHFFFAOYSA-N 0.000 claims 1
- HMLJINRNVYUTBC-UHFFFAOYSA-N 3-[6-[(3,3-diethyl-1h-2-benzofuran-5-yl)oxy]pyridin-3-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound C1=C2C(CC)(CC)OCC2=CC=C1OC(N=C1)=CC=C1N1C(=O)NC(C)(C)C1=O HMLJINRNVYUTBC-UHFFFAOYSA-N 0.000 claims 1
- CPGJUZILFONYDJ-UHFFFAOYSA-N 3-[6-[(3,3-dimethyl-2h-1-benzofuran-5-yl)oxy]pyridin-3-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound C1=C2C(C)(C)COC2=CC=C1OC(N=C1)=CC=C1N1C(=O)NC(C)(C)C1=O CPGJUZILFONYDJ-UHFFFAOYSA-N 0.000 claims 1
- UTGNGYYHQDVNBY-UHFFFAOYSA-N 3-[6-[(3-ethyl-1,3-dihydro-2-benzofuran-5-yl)oxy]pyridin-3-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound C1=C2C(CC)OCC2=CC=C1OC(N=C1)=CC=C1N1C(=O)NC(C)(C)C1=O UTGNGYYHQDVNBY-UHFFFAOYSA-N 0.000 claims 1
- BLQYVYOXUXLEPY-UHFFFAOYSA-N 3-[6-[(4,4-dimethyl-1,3-dihydroisochromen-6-yl)oxy]pyridin-3-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COCC2(C)C)C2=C1 BLQYVYOXUXLEPY-UHFFFAOYSA-N 0.000 claims 1
- QIOGLBJFQABTME-UHFFFAOYSA-N 3-cyclopropyl-1,3-dihydro-2-benzofuran-5-ol Chemical compound C12=CC(O)=CC=C2COC1C1CC1 QIOGLBJFQABTME-UHFFFAOYSA-N 0.000 claims 1
- PERVTWOJHRUPSM-UHFFFAOYSA-N 3-ethyl-1,3-dihydro-2-benzofuran-5-ol Chemical compound C1=C(O)C=C2C(CC)OCC2=C1 PERVTWOJHRUPSM-UHFFFAOYSA-N 0.000 claims 1
- CWAAIRDZAWUAEX-UHFFFAOYSA-N 3-methyl-3-(trifluoromethyl)-1h-2-benzofuran-5-ol Chemical compound C1=C(O)C=C2C(C)(C(F)(F)F)OCC2=C1 CWAAIRDZAWUAEX-UHFFFAOYSA-N 0.000 claims 1
- JAPDYYGHMBSWNY-UHFFFAOYSA-N 3-tert-butyl-1,3-dihydro-2-benzofuran-5-ol Chemical compound C1=C(O)C=C2C(C(C)(C)C)OCC2=C1 JAPDYYGHMBSWNY-UHFFFAOYSA-N 0.000 claims 1
- FDNGFPQTMSOIRB-UHFFFAOYSA-N 4,4-dimethyl-1,3-dihydroisochromen-6-ol Chemical compound C1=C(O)C=C2C(C)(C)COCC2=C1 FDNGFPQTMSOIRB-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- XZCMOAFWCRQHLN-UHFFFAOYSA-N 5,5-dimethyl-3-(2-spiro[1h-2-benzofuran-3,1'-cyclopentane]-5-yloxypyrimidin-5-yl)imidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(COC23CCCC3)C2=C1 XZCMOAFWCRQHLN-UHFFFAOYSA-N 0.000 claims 1
- XLLYTTJDCNRJGT-UHFFFAOYSA-N 5,5-dimethyl-3-(6-spiro[1h-2-benzofuran-3,1'-cyclopentane]-5-yloxypyridin-3-yl)imidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(COC23CCCC3)C2=C1 XLLYTTJDCNRJGT-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- HOZNJMSYPCWZEW-UHFFFAOYSA-N C12(CCC1)OCC1=CC=C(C=C12)OC1=NC=C(C=N1)N1C(NC(C1)=O)=O Chemical compound C12(CCC1)OCC1=CC=C(C=C12)OC1=NC=C(C=N1)N1C(NC(C1)=O)=O HOZNJMSYPCWZEW-UHFFFAOYSA-N 0.000 claims 1
- MKRCLSLPSOGFMF-UHFFFAOYSA-N CCC(C1=C2)OCC1=CC=C2OC(N=C1)=CC=C1N(C(C)(C)C(N1)=O)C1=O Chemical compound CCC(C1=C2)OCC1=CC=C2OC(N=C1)=CC=C1N(C(C)(C)C(N1)=O)C1=O MKRCLSLPSOGFMF-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 231100000888 hearing loss Toxicity 0.000 claims 1
- 230000010370 hearing loss Effects 0.000 claims 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 1
- 229940091173 hydantoin Drugs 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [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
- XKQQGXAQKQKNQR-UHFFFAOYSA-N spiro[1h-2-benzofuran-3,1'-cyclobutane]-5-ol Chemical compound C12=CC(O)=CC=C2COC21CCC2 XKQQGXAQKQKNQR-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
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| GBGB1109514.8A GB201109514D0 (en) | 2011-06-07 | 2011-06-07 | Novel compounds |
| GB1109514.8 | 2011-06-07 | ||
| GBGB1113761.9A GB201113761D0 (en) | 2011-08-10 | 2011-08-10 | Novel compounds |
| GB1113761.9 | 2011-08-10 | ||
| GB1209986.7 | 2012-06-06 | ||
| GBGB1209986.7A GB201209986D0 (en) | 2012-06-06 | 2012-06-06 | Novel compounds |
| PCT/GB2012/051278 WO2012168710A1 (en) | 2011-06-07 | 2012-06-07 | Hydantoin derivates as kv3 inhibitors |
Publications (3)
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| JP2014516073A JP2014516073A (ja) | 2014-07-07 |
| JP2014516073A5 true JP2014516073A5 (https=) | 2015-07-23 |
| JP6008953B2 JP6008953B2 (ja) | 2016-10-19 |
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| EP (1) | EP2718285B1 (https=) |
| JP (1) | JP6008953B2 (https=) |
| CN (1) | CN103596943B (https=) |
| BR (1) | BR112013031402A2 (https=) |
| WO (1) | WO2012168710A1 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2509961B1 (en) * | 2009-12-11 | 2016-03-09 | Autifony Therapeutics Limited | Imidazolidinedione derivatives |
| EA023768B1 (ru) | 2010-12-06 | 2016-07-29 | Отифони Терапеутикс Лимитед | ПРОИЗВОДНЫЕ ГИДАНТОИНА, ПОЛЕЗНЫЕ В КАЧЕСТВЕ ИНГИБИТОРОВ Kv3-КАНАЛОВ |
| GB201209986D0 (en) | 2012-06-06 | 2012-07-18 | Autifony Therapeutics Ltd | Novel compounds |
| EP2788339B1 (en) * | 2011-12-06 | 2016-03-09 | Autifony Therapeutics Limited | Hydantoin derivatives useful as kv3 inhibitors |
| US9669030B2 (en) | 2012-05-22 | 2017-06-06 | Autifony Therapeutics Limited | Hydantoin derivatives as Kv3 inhibitors |
| US9422252B2 (en) | 2012-05-22 | 2016-08-23 | Autifony Therapeutics Limited | Triazoles 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 |
| GB201521751D0 (en) | 2015-12-10 | 2016-01-27 | Autifony Therapeutics Ltd | Novel uses |
| JOP20190005A1 (ar) * | 2016-07-20 | 2019-01-20 | Bayer Ag | مركبات ديازاهيترو ثنائية الحلقة مستبدلة واستخداماتها |
| GB201613163D0 (en) | 2016-07-29 | 2016-09-14 | Autifony Therapeutics Ltd | Novel compounds |
| EP3555073A1 (en) | 2016-12-16 | 2019-10-23 | Autifony Therapeutics Limited | Hydantoin modulators of kv3 channels |
| WO2018220762A1 (ja) * | 2017-05-31 | 2018-12-06 | 大塚製薬株式会社 | ピリミジン化合物 |
| JP7336469B2 (ja) | 2017-09-08 | 2023-08-31 | シムベリックス，インコーポレーティッド | β－グルクロニダーゼを選択的に阻害し、薬物治療誘発性下痢に関連する副作用を緩和する化合物、組成物、及び方法 |
| US12358901B2 (en) | 2018-10-16 | 2025-07-15 | Autifony Therapeutics Limited | KV3 modulators |
| KR102854594B1 (ko) | 2018-10-16 | 2025-09-02 | 오티포니 세라피틱스 리미티드 | 신규한 화합물 |
| MY210184A (en) | 2018-11-30 | 2025-08-31 | Otsuka Pharma Co Ltd | Heterocyclic compounds for the treatment of epilepsy |
| BR112022013339A2 (pt) | 2020-02-06 | 2022-09-13 | Autifony Therapeutics Ltd | Moduladores de kv3 |
| KR20240046748A (ko) | 2021-08-10 | 2024-04-09 | 오티포니 세라피틱스 리미티드 | 칼륨 채널 조절제 |
| CN114605331A (zh) * | 2022-03-17 | 2022-06-10 | 上海健康医学院 | 一种尼鲁米特及其中间体的制备方法 |
| CN115536509B (zh) * | 2022-04-06 | 2023-11-07 | 苏州当量生物医药有限公司 | 2-溴-4-羟基苯甲醛的合成方法 |
| WO2024121552A1 (en) | 2022-12-06 | 2024-06-13 | Autifony Therapeutics Limited | Compounds for the treatment of centra nervous system disorders |
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| CA2524221A1 (en) | 2003-04-30 | 2004-11-18 | The Institutes For Pharmaceutical Discovery, Llc | Substituted heteroaryls as inhibitors of protein tyrosine phosphatases |
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| LT2656842T (lt) | 2006-03-27 | 2016-09-26 | The Regents Of The University Of California | Androgeno receptoriaus moduliatorius, skirtas prostatos vėžio ir su androgeno receptoriumi susijusių ligų gydymui |
| KR101456722B1 (ko) | 2006-03-29 | 2014-10-31 | 더 리전트 오브 더 유니버시티 오브 캘리포니아 | 디아릴티오히단토인 화합물 |
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| KR20130097813A (ko) * | 2008-04-21 | 2013-09-03 | 오토노미, 인코포레이티드 | 귀 질환 및 병태를 치료하기 위한 귀 조제물 |
| EP2379534A1 (en) | 2008-12-22 | 2011-10-26 | F. Hoffmann-La Roche AG | Heterocyclic antiviral compounds |
| EP2509961B1 (en) | 2009-12-11 | 2016-03-09 | Autifony Therapeutics Limited | Imidazolidinedione derivatives |
| WO2011073114A1 (en) | 2009-12-14 | 2011-06-23 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| EA023768B1 (ru) * | 2010-12-06 | 2016-07-29 | Отифони Терапеутикс Лимитед | ПРОИЗВОДНЫЕ ГИДАНТОИНА, ПОЛЕЗНЫЕ В КАЧЕСТВЕ ИНГИБИТОРОВ Kv3-КАНАЛОВ |
| GB201209986D0 (en) | 2012-06-06 | 2012-07-18 | Autifony Therapeutics Ltd | Novel compounds |
| EP2788339B1 (en) | 2011-12-06 | 2016-03-09 | Autifony Therapeutics Limited | Hydantoin derivatives useful as kv3 inhibitors |
| US9669030B2 (en) | 2012-05-22 | 2017-06-06 | Autifony Therapeutics Limited | Hydantoin derivatives as Kv3 inhibitors |
| US9422252B2 (en) | 2012-05-22 | 2016-08-23 | Autifony Therapeutics Limited | Triazoles 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 |
-
2012
- 2012-06-07 CN CN201280027811.XA patent/CN103596943B/zh not_active Expired - Fee Related
- 2012-06-07 WO PCT/GB2012/051278 patent/WO2012168710A1/en not_active Ceased
- 2012-06-07 EP EP12726849.8A patent/EP2718285B1/en active Active
- 2012-06-07 JP JP2014514148A patent/JP6008953B2/ja not_active Expired - Fee Related
- 2012-06-07 BR BR112013031402A patent/BR112013031402A2/pt not_active Application Discontinuation
- 2012-06-07 US US14/124,516 patent/US9193704B2/en active Active
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