JP2014516073A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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 |
|---|---|---|---|
| GB1109514.8 | 2011-06-07 | ||
| GBGB1109514.8A GB201109514D0 (en) | 2011-06-07 | 2011-06-07 | Novel compounds |
| GB1113761.9 | 2011-08-10 | ||
| GBGB1113761.9A GB201113761D0 (en) | 2011-08-10 | 2011-08-10 | Novel compounds |
| GBGB1209986.7A GB201209986D0 (en) | 2012-06-06 | 2012-06-06 | Novel compounds |
| GB1209986.7 | 2012-06-06 | ||
| PCT/GB2012/051278 WO2012168710A1 (en) | 2011-06-07 | 2012-06-07 | Hydantoin derivates as kv3 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014516073A JP2014516073A (ja) | 2014-07-07 |
| JP2014516073A5 true JP2014516073A5 (OSRAM) | 2015-07-23 |
| JP6008953B2 JP6008953B2 (ja) | 2016-10-19 |
Family
ID=46246100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014514148A Expired - Fee Related JP6008953B2 (ja) | 2011-06-07 | 2012-06-07 | Ｋｖ３阻害剤としてのヒダントイン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9193704B2 (OSRAM) |
| EP (1) | EP2718285B1 (OSRAM) |
| JP (1) | JP6008953B2 (OSRAM) |
| CN (1) | CN103596943B (OSRAM) |
| BR (1) | BR112013031402A2 (OSRAM) |
| WO (1) | WO2012168710A1 (OSRAM) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101735675B1 (ko) * | 2009-12-11 | 2017-05-15 | 오티포니 세라피틱스 리미티드 | 이미다졸리딘디온 유도체 |
| US9346790B2 (en) | 2010-12-06 | 2016-05-24 | Autifony Therapeutics Limited | Hydantoin derivatives useful as Kv3 inhibitors |
| GB201209986D0 (en) | 2012-06-06 | 2012-07-18 | Autifony Therapeutics Ltd | Novel compounds |
| IN2014CN04014A (OSRAM) * | 2011-12-06 | 2015-07-10 | Autifony Therapeutics Ltd | |
| WO2013175211A1 (en) * | 2012-05-22 | 2013-11-28 | Autifony Therapeutics Limited | Hydantoin derivatives as kv3 inhibitors |
| BR112014028991A2 (pt) | 2012-05-22 | 2017-06-27 | Autifony Therapeutics Ltd | triazóis como inibidores de kv3 |
| 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 |
| US12017994B2 (en) | 2017-09-08 | 2024-06-25 | Symberix, Inc. | Compounds, compositions, and methods for selectively inhibiting β-glucuronidases and alleviating side effects associated with drug treatment induced diarrhea |
| US12358901B2 (en) | 2018-10-16 | 2025-07-15 | Autifony Therapeutics Limited | KV3 modulators |
| FI3867247T3 (fi) | 2018-10-16 | 2024-10-30 | Autifony Therapeutics Ltd | Uusia yhdisteitä |
| AU2019390907B2 (en) | 2018-11-30 | 2025-05-08 | Otsuka Pharmaceutical Co., Ltd. | Heterocyclic compounds for the treatment of epilepsy |
| KR20220139923A (ko) | 2020-02-06 | 2022-10-17 | 오티포니 세라피틱스 리미티드 | Kv3 조절제 |
| US20240327406A1 (en) | 2021-08-10 | 2024-10-03 | Autifony Therapeutics Limited | Potassium channel modulators |
| 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 |
| EP4630117A1 (en) | 2022-12-06 | 2025-10-15 | Autifony Therapeutics Limited | Compounds for the treatment of centra nervous system disorders |
Family Cites Families (43)
| 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 |
| JPS63228150A (ja) * | 1987-03-17 | 1988-09-22 | Konica Corp | 有機着色物質の光褪色防止方法 |
| 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) |
| DK123493D0 (da) | 1993-11-01 | 1993-11-01 | Lundbeck & Co As H | Compounds |
| WO1996036229A1 (en) | 1995-05-17 | 1996-11-21 | E.I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
| MX9708802A (es) | 1995-05-17 | 1998-02-28 | Du Pont | Amidas ciclicas fungicidas. |
| EP0836384A1 (en) | 1995-06-20 | 1998-04-22 | E.I. Du Pont De Nemours And Company | Arthropodicidal 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. |
| WO1998023155A1 (en) | 1996-11-26 | 1998-06-04 | E.I. Du Pont De Nemours And Company | Arthropodicidal and fungicidal cyclic amides |
| EP0944314A1 (en) | 1996-11-26 | 1999-09-29 | E.I. Du Pont De Nemours And Company | Methyl substituted fungicides and arthropodicides |
| WO1998033382A1 (en) | 1997-01-30 | 1998-08-06 | E.I. Du Pont De Nemours And Company | Fungicidal compositions |
| RU2230551C2 (ru) | 1999-07-23 | 2004-06-20 | ШИОНОГИ энд КО, ЛТД. | Ингибиторы th2-дифференцировки |
| WO2001074331A1 (en) | 2000-04-04 | 2001-10-11 | Shionogi & Co., Ltd. | Oily compositions containing highly fat-soluble drugs |
| WO2001076582A1 (fr) | 2000-04-05 | 2001-10-18 | Shionogi & Co., Ltd. | Micro-emulsions huile dans eau contenant des composes tricycliques ou des preconcentres de ceux-ci |
| 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 |
| EP1485088B1 (en) | 2002-02-07 | 2008-08-06 | The Curators Of The University Of Missouri | Opioid receptor active 4-(3-hydroxyphenyl) or 4-(3-alkoxyphenyl)-1,2,4-triazole compounds |
| ES2290743T3 (es) | 2003-04-30 | 2008-02-16 | The Institutes For Pharmaceutical Discovery, Llc | Heteroarilos sustituidos como inhibidores de las proteina-tirosina fosfatasas. |
| WO2005000309A2 (en) | 2003-06-27 | 2005-01-06 | Ionix Pharmaceuticals Limited | Chemical compounds |
| US7256208B2 (en) | 2003-11-13 | 2007-08-14 | Bristol-Myers Squibb Company | Monocyclic N-Aryl hydantoin modulators of androgen receptor function |
| US20060211697A1 (en) | 2004-12-08 | 2006-09-21 | Liren Huang | 2-(2 Or 4-substituted aryloxy)-phenol derivatives as antibacterial agents |
| RS53967B1 (sr) | 2005-05-13 | 2015-08-31 | The Regents Of The University Of California | Diaril hidantoin jedinjenja kao antagonisti receptora androgena za lečenje raka |
| US7709517B2 (en) | 2005-05-13 | 2010-05-04 | The Regents Of The University Of California | Diarylhydantoin compounds |
| WO2007012064A2 (en) * | 2005-07-20 | 2007-01-25 | Cypress Bioscience, Inc. | Prevention and treatment of hearing disorders |
| LT2656841T (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 |
| MX2008012492A (es) | 2006-03-29 | 2008-12-12 | Univ California | Compuestos de diariltiohidantoina. |
| CA2684950A1 (en) | 2007-04-20 | 2008-10-30 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
| MX2010011545A (es) * | 2008-04-21 | 2011-04-11 | Otonomy Inc | Formulaciones para tratar enfermedades y afecciones del oido. |
| AU2009331660A1 (en) | 2008-12-22 | 2011-06-30 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| KR101735675B1 (ko) | 2009-12-11 | 2017-05-15 | 오티포니 세라피틱스 리미티드 | 이미다졸리딘디온 유도체 |
| WO2011073114A1 (en) | 2009-12-14 | 2011-06-23 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| US9346790B2 (en) * | 2010-12-06 | 2016-05-24 | Autifony Therapeutics Limited | Hydantoin derivatives useful as Kv3 inhibitors |
| GB201209986D0 (en) | 2012-06-06 | 2012-07-18 | Autifony Therapeutics Ltd | Novel compounds |
| IN2014CN04014A (OSRAM) | 2011-12-06 | 2015-07-10 | Autifony Therapeutics Ltd | |
| WO2013175211A1 (en) | 2012-05-22 | 2013-11-28 | Autifony Therapeutics Limited | Hydantoin derivatives as kv3 inhibitors |
| BR112014028991A2 (pt) | 2012-05-22 | 2017-06-27 | Autifony Therapeutics Ltd | triazóis como inibidores de kv3 |
| 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 EP EP12726849.8A patent/EP2718285B1/en active Active
- 2012-06-07 WO PCT/GB2012/051278 patent/WO2012168710A1/en not_active Ceased
- 2012-06-07 CN CN201280027811.XA patent/CN103596943B/zh not_active Expired - Fee Related
- 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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2014516073A5 (OSRAM) | ||
| JP2013544873A5 (OSRAM) | ||
| JP2016145215A5 (OSRAM) | ||
| JP2015520764A5 (OSRAM) | ||
| JP2015517563A5 (OSRAM) | ||
| US9278960B2 (en) | Quinoline carboxamide and quinoline carbonitrile derivatives as mGluR2-negative allosteric modulators, compositions, and their use | |
| JP6162144B2 (ja) | ４，４−二置換−１，４−ジヒドロピリミジン、及びｂ型肝炎の処置のための医薬としてのその使用 | |
| IL258577A (en) | 2,4-dihydroxy-nicotinamides as apj agonists | |
| JP2013545744A5 (OSRAM) | ||
| JP2019506367A5 (OSRAM) | ||
| JP2016538313A5 (OSRAM) | ||
| RU2018112237A (ru) | Новые бициклические соединения в качестве дуальных ингибиторов atx/ca | |
| JP2015502951A5 (OSRAM) | ||
| JP2010508338A5 (OSRAM) | ||
| JP2017510576A5 (OSRAM) | ||
| JP2019537594A5 (OSRAM) | ||
| JP2018530591A5 (OSRAM) | ||
| RU2014124640A (ru) | Производные аминопиримидина в качестве модуляторов богатой лейцином повторной киназы 2 (lrrk2) | |
| JP2017513894A5 (OSRAM) | ||
| RU2013136542A (ru) | Конденсированные производные аминодигидротиазина | |
| JP2014501246A5 (OSRAM) | ||
| RU2012145237A (ru) | Производные арилэтинила | |
| RU2010137300A (ru) | Модуляторы бета-амилоида | |
| RU2012105284A (ru) | Спиро-аминосоединения, пригодные для лечения нарушений сна и лекарственного привыкания | |
| JP2014532619A5 (OSRAM) |