JP2013544873A5 - - Google Patents
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- Publication number
- JP2013544873A5 JP2013544873A5 JP2013542606A JP2013542606A JP2013544873A5 JP 2013544873 A5 JP2013544873 A5 JP 2013544873A5 JP 2013542606 A JP2013542606 A JP 2013542606A JP 2013542606 A JP2013542606 A JP 2013542606A JP 2013544873 A5 JP2013544873 A5 JP 2013544873A5
- Authority
- JP
- Japan
- Prior art keywords
- oxy
- methyl
- imidazolidinedione
- ethyl
- benzofuran
- 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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- 150000001875 compounds Chemical class 0.000 claims 25
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 239000000203 mixture Substances 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 16
- -1 1a-methyl-1,1a, 2,7b-tetrahydrocyclopropa [c] chromen-7-yl Chemical group 0.000 claims 14
- 208000016354 hearing loss disease Diseases 0.000 claims 11
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 10
- 239000004472 Lysine Substances 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 230000002265 prevention Effects 0.000 claims 6
- DJHFOZLDQVQSLW-GICMACPYSA-N (5r)-5-ethyl-3-[6-[(3-ethyl-1,3-dihydro-2-benzofuran-4-yl)oxy]pyridin-3-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@@H](CC)NC(=O)N1C(C=N1)=CC=C1OC1=CC=CC2=C1C(CC)OC2 DJHFOZLDQVQSLW-GICMACPYSA-N 0.000 claims 4
- HOUSIKSZRMQPPQ-UHFFFAOYSA-N 5,5-dimethyl-3-[6-[(3-methyl-3,4-dihydro-2h-chromen-5-yl)oxy]pyridin-3-yl]imidazolidine-2,4-dione Chemical compound C=12CC(C)COC2=CC=CC=1OC(N=C1)=CC=C1N1C(=O)NC(C)(C)C1=O HOUSIKSZRMQPPQ-UHFFFAOYSA-N 0.000 claims 4
- 206010011878 Deafness Diseases 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000006413 ring segment Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 201000000980 schizophrenia Diseases 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 3
- MUHADSVSTHSYGD-GFCCVEGCSA-N (5r)-3-[2-[(3,3-dimethyl-2h-1-benzofuran-4-yl)oxy]pyrimidin-5-yl]-5-ethylimidazolidine-2,4-dione Chemical compound O=C1[C@@H](CC)NC(=O)N1C(C=N1)=CN=C1OC1=CC=CC2=C1C(C)(C)CO2 MUHADSVSTHSYGD-GFCCVEGCSA-N 0.000 claims 2
- CLAKLXYCHLXXMD-MRXNPFEDSA-N (5r)-3-[2-[(3,3-dimethyl-2h-1-benzofuran-4-yl)oxy]pyrimidin-5-yl]-5-propan-2-ylimidazolidine-2,4-dione Chemical compound O=C1[C@@H](C(C)C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=CC2=C1C(C)(C)CO2 CLAKLXYCHLXXMD-MRXNPFEDSA-N 0.000 claims 2
- DEZRPEPAVNAFNI-LLVKDONJSA-N (5r)-3-[4-(1,3-dihydro-2-benzofuran-4-yloxy)phenyl]-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@@H](C)NC(=O)N1C(C=C1)=CC=C1OC1=CC=CC2=C1COC2 DEZRPEPAVNAFNI-LLVKDONJSA-N 0.000 claims 2
- JYJGIGZDJIZOOU-GFCCVEGCSA-N (5r)-3-[4-[(3,3-dimethyl-2h-1-benzofuran-4-yl)oxy]phenyl]-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@@H](C)NC(=O)N1C(C=C1)=CC=C1OC1=CC=CC2=C1C(C)(C)CO2 JYJGIGZDJIZOOU-GFCCVEGCSA-N 0.000 claims 2
- BHSLNPYKWBHNJV-GFCCVEGCSA-N (5r)-3-[4-[(3,6-dimethyl-1,2-benzoxazol-4-yl)oxy]phenyl]-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@@H](C)NC(=O)N1C(C=C1)=CC=C1OC1=CC(C)=CC2=C1C(C)=NO2 BHSLNPYKWBHNJV-GFCCVEGCSA-N 0.000 claims 2
- JRJFHQWKQUKYGP-PUMZCOHWSA-N (5r)-3-[6-(1,1a,2,7b-tetrahydrocyclopropa[c]chromen-7-yloxy)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=CC2=C1C1CC1CO2 JRJFHQWKQUKYGP-PUMZCOHWSA-N 0.000 claims 2
- BANNWOFBMMRBFI-CYBMUJFWSA-N (5r)-3-[6-[(3,3-dimethyl-2h-1-benzofuran-4-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=CC2=C1C(C)(C)CO2 BANNWOFBMMRBFI-CYBMUJFWSA-N 0.000 claims 2
- UFXXLHLRZQDWQK-LLVKDONJSA-N (5r)-3-[6-[(3,3-dimethyl-2h-1-benzofuran-4-yl)oxy]pyridin-3-yl]-5-methylimidazolidine-2,4-dione Chemical compound O=C1[C@@H](C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=CC2=C1C(C)(C)CO2 UFXXLHLRZQDWQK-LLVKDONJSA-N 0.000 claims 2
- XOWFIAMSTPQWIU-CYBMUJFWSA-N (5r)-5-ethyl-3-(6-spiro[2h-1-benzofuran-3,1'-cyclopropane]-4-yloxypyridin-3-yl)imidazolidine-2,4-dione Chemical compound O=C1[C@@H](CC)NC(=O)N1C(C=N1)=CC=C1OC1=CC=CC2=C1C1(CC1)CO2 XOWFIAMSTPQWIU-CYBMUJFWSA-N 0.000 claims 2
- UCUCGUSVXQPQHJ-CYBMUJFWSA-N (5r)-5-ethyl-3-[6-[(3-ethyl-1,2-benzoxazol-4-yl)oxy]pyridin-3-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@@H](CC)NC(=O)N1C(C=N1)=CC=C1OC1=CC=CC2=C1C(CC)=NO2 UCUCGUSVXQPQHJ-CYBMUJFWSA-N 0.000 claims 2
- SUGOIOCOVYLITH-SBXXRYSUSA-N (5r)-5-ethyl-3-[6-[(3-methyl-1,3-dihydro-2-benzofuran-4-yl)oxy]pyridin-3-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@@H](CC)NC(=O)N1C(C=N1)=CC=C1OC1=CC=CC2=C1C(C)OC2 SUGOIOCOVYLITH-SBXXRYSUSA-N 0.000 claims 2
- KGOZBBRMSFXYCI-CYBMUJFWSA-N (5r)-5-ethyl-3-[6-[(3-propan-2-yl-1,2-benzoxazol-4-yl)oxy]pyridin-3-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@@H](CC)NC(=O)N1C(C=N1)=CC=C1OC1=CC=CC2=C1C(C(C)C)=NO2 KGOZBBRMSFXYCI-CYBMUJFWSA-N 0.000 claims 2
- DJFNGVMCJLQBNE-HXUWFJFHSA-N (5r)-5-ethyl-5-methyl-3-(2-spiro[2,3-dihydrochromene-4,1'-cyclopropane]-5-yloxypyrimidin-5-yl)imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=CC2=C1C1(CC1)CCO2 DJFNGVMCJLQBNE-HXUWFJFHSA-N 0.000 claims 2
- CPDWLGQBLZMRST-HXUWFJFHSA-N (5r)-5-ethyl-5-methyl-3-(6-spiro[2h-1-benzofuran-3,1'-cyclopropane]-4-yloxypyridin-3-yl)imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=CC2=C1C1(CC1)CO2 CPDWLGQBLZMRST-HXUWFJFHSA-N 0.000 claims 2
- WBZCSPNCZZLTMR-LLVKDONJSA-N (5r)-5-methyl-3-[4-[(3-methyl-1,2-benzoxazol-4-yl)oxy]phenyl]imidazolidine-2,4-dione Chemical compound O=C1[C@@H](C)NC(=O)N1C(C=C1)=CC=C1OC1=CC=CC2=C1C(C)=NO2 WBZCSPNCZZLTMR-LLVKDONJSA-N 0.000 claims 2
- NPLOCGGQYSBOPP-INIZCTEOSA-N (5r)-5-tert-butyl-3-[2-[(3,3-dimethyl-2h-1-benzofuran-4-yl)oxy]pyrimidin-5-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@@H](C(C)(C)C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=CC2=C1C(C)(C)CO2 NPLOCGGQYSBOPP-INIZCTEOSA-N 0.000 claims 2
- RLZSNZIJMXBLGI-UHFFFAOYSA-N 3-[2-[(3,3-dimethyl-2h-1-benzofuran-4-yl)oxy]pyrimidin-5-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound C=12C(C)(C)COC2=CC=CC=1OC(N=C1)=NC=C1N1C(=O)NC(C)(C)C1=O RLZSNZIJMXBLGI-UHFFFAOYSA-N 0.000 claims 2
- QKKIXMMFPYSTEH-UHFFFAOYSA-N 3-[6-[(3,3-dimethyl-2h-1-benzofuran-4-yl)oxy]pyridin-3-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound C=12C(C)(C)COC2=CC=CC=1OC(N=C1)=CC=C1N1C(=O)NC(C)(C)C1=O QKKIXMMFPYSTEH-UHFFFAOYSA-N 0.000 claims 2
- AOZHFMOQYJFMFL-UHFFFAOYSA-N 3-[6-[(3-ethyl-1,3-dihydro-2-benzofuran-4-yl)oxy]pyridin-3-yl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound C=12C(CC)OCC2=CC=CC=1OC(N=C1)=CC=C1N1C(=O)NC(C)(C)C1=O AOZHFMOQYJFMFL-UHFFFAOYSA-N 0.000 claims 2
- FGWRIDDFGDQKEH-UHFFFAOYSA-N 5,5-dimethyl-3-(6-spiro[1,3-dihydroisochromene-4,1'-cyclopropane]-5-yloxypyridin-3-yl)imidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=CC2=C1C1(CC1)COC2 FGWRIDDFGDQKEH-UHFFFAOYSA-N 0.000 claims 2
- BUQRXVHOLHZBJQ-UHFFFAOYSA-N 5,5-dimethyl-3-(6-spiro[2h-1-benzofuran-3,1'-cyclopropane]-4-yloxypyridin-3-yl)imidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=CC2=C1C1(CC1)CO2 BUQRXVHOLHZBJQ-UHFFFAOYSA-N 0.000 claims 2
- JBUBKHPJMWXPDR-UHFFFAOYSA-N 5,5-dimethyl-3-[4-[(3-methyl-1,2-benzoxazol-4-yl)oxy]phenyl]imidazolidine-2,4-dione Chemical compound C=12C(C)=NOC2=CC=CC=1OC(C=C1)=CC=C1N1C(=O)NC(C)(C)C1=O JBUBKHPJMWXPDR-UHFFFAOYSA-N 0.000 claims 2
- FEABXCREHFVJCI-UHFFFAOYSA-N 5,5-dimethyl-3-[6-[(4-methyl-3,4-dihydro-2h-chromen-5-yl)oxy]pyridin-3-yl]imidazolidine-2,4-dione Chemical compound C=12C(C)CCOC2=CC=CC=1OC(N=C1)=CC=C1N1C(=O)NC(C)(C)C1=O FEABXCREHFVJCI-UHFFFAOYSA-N 0.000 claims 2
- ZJEURBVUUVBUMC-UHFFFAOYSA-N 6-[6-[(3,3-dimethyl-2h-1-benzofuran-4-yl)oxy]pyridin-3-yl]-4,6-diazaspiro[2.4]heptane-5,7-dione Chemical compound C=12C(C)(C)COC2=CC=CC=1OC(N=C1)=CC=C1N(C1=O)C(=O)NC21CC2 ZJEURBVUUVBUMC-UHFFFAOYSA-N 0.000 claims 2
- GOPBAXGLRUCBSV-UHFFFAOYSA-N 7-[6-[(3,3-dimethyl-2h-1-benzofuran-4-yl)oxy]pyridin-3-yl]-5,7-diazaspiro[3.4]octane-6,8-dione Chemical compound C=12C(C)(C)COC2=CC=CC=1OC(N=C1)=CC=C1N(C1=O)C(=O)NC21CCC2 GOPBAXGLRUCBSV-UHFFFAOYSA-N 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 2
- 208000009205 Tinnitus Diseases 0.000 claims 2
- 231100000895 deafness Toxicity 0.000 claims 2
- 229910052805 deuterium Inorganic materials 0.000 claims 2
- 231100000888 hearing loss Toxicity 0.000 claims 2
- 230000010370 hearing loss Effects 0.000 claims 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 208000020685 sleep-wake disease Diseases 0.000 claims 2
- 231100000886 tinnitus Toxicity 0.000 claims 2
- LFBFJRDCNKBXII-MRXNPFEDSA-N (5r)-3-[2-[(2,2-difluoro-1,3-benzodioxol-4-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=CC2=C1OC(F)(F)O2 LFBFJRDCNKBXII-MRXNPFEDSA-N 0.000 claims 1
- MCSCOJJHSDROQX-QGZVFWFLSA-N (5r)-3-[2-[(2,2-difluoro-7-methyl-1,3-benzodioxol-4-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(C)C2=C1OC(F)(F)O2 MCSCOJJHSDROQX-QGZVFWFLSA-N 0.000 claims 1
- NTIWPSOEUHNVTN-OAQYLSRUSA-N (5r)-3-[2-[(3,3-dimethyl-1,4-dihydroisochromen-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=CC2=C1CC(C)(C)OC2 NTIWPSOEUHNVTN-OAQYLSRUSA-N 0.000 claims 1
- NXFZEVSAUSOECI-JOCHJYFZSA-N (5r)-3-[6-[(3,3-diethyl-1h-2-benzofuran-4-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=CC2=C1C(CC)(CC)OC2 NXFZEVSAUSOECI-JOCHJYFZSA-N 0.000 claims 1
- JXNSTUBOQNDSKJ-JOCHJYFZSA-N (5r)-3-[6-[(3,3-dimethyl-1,4-dihydroisochromen-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=CC2=C1CC(C)(C)OC2 JXNSTUBOQNDSKJ-JOCHJYFZSA-N 0.000 claims 1
- QHYRGKMMPURNST-OAQYLSRUSA-N (5r)-3-[6-[(3,3-dimethyl-1h-2-benzofuran-4-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=CC2=C1C(C)(C)OC2 QHYRGKMMPURNST-OAQYLSRUSA-N 0.000 claims 1
- LWGBRPAONSBLOJ-CYBMUJFWSA-N (5r)-5-ethyl-3-[2-(7-methylspiro[2h-1-benzofuran-3,1'-cyclopropane]-4-yl)oxypyrimidin-5-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@@H](CC)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(C)C2=C1C1(CC1)CO2 LWGBRPAONSBLOJ-CYBMUJFWSA-N 0.000 claims 1
- NPNNMBCPDXXEAG-CQSZACIVSA-N (5r)-5-ethyl-3-[6-(7-methylspiro[2h-1-benzofuran-3,1'-cyclopropane]-4-yl)oxypyridin-3-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@@H](CC)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(C)C2=C1C1(CC1)CO2 NPNNMBCPDXXEAG-CQSZACIVSA-N 0.000 claims 1
- MDESKNKMZVMFSF-OAQYLSRUSA-N (5r)-5-ethyl-5-methyl-3-[2-(7-methylspiro[1h-2-benzofuran-3,1'-cyclobutane]-4-yl)oxypyrimidin-5-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(C)C2=C1C1(CCC1)OC2 MDESKNKMZVMFSF-OAQYLSRUSA-N 0.000 claims 1
- VJORKOHZKOIAOJ-HXUWFJFHSA-N (5r)-5-ethyl-5-methyl-3-[2-(7-methylspiro[2h-1-benzofuran-3,1'-cyclopropane]-4-yl)oxypyrimidin-5-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CN=C1OC1=CC=C(C)C2=C1C1(CC1)CO2 VJORKOHZKOIAOJ-HXUWFJFHSA-N 0.000 claims 1
- LMDIRIJUNRBPAD-OAQYLSRUSA-N (5r)-5-ethyl-5-methyl-3-[2-[(2,4,4-trimethyl-3,1-benzoxazin-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=CC2=C1C(C)(C)OC(C)=N2 LMDIRIJUNRBPAD-OAQYLSRUSA-N 0.000 claims 1
- OYFGQTVERWVDGF-OAQYLSRUSA-N (5r)-5-ethyl-5-methyl-3-[2-[(3,3,7-trimethyl-2h-1-benzofuran-4-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(C)C2=C1C(C)(C)CO2 OYFGQTVERWVDGF-OAQYLSRUSA-N 0.000 claims 1
- WGUQZTNFOFTICR-VLFLDKFOSA-N (5r)-5-ethyl-5-methyl-3-[2-[(4-methyl-3,4-dihydro-2h-chromen-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=CC2=C1C(C)CCO2 WGUQZTNFOFTICR-VLFLDKFOSA-N 0.000 claims 1
- CWHUKRBJRARMCX-OAQYLSRUSA-N (5r)-5-ethyl-5-methyl-3-[6-(7-methylspiro[2h-1-benzofuran-3,1'-cyclopropane]-4-yl)oxypyridin-3-yl]imidazolidine-2,4-dione Chemical compound O=C1[C@](CC)(C)NC(=O)N1C(C=N1)=CC=C1OC1=CC=C(C)C2=C1C1(CC1)CO2 CWHUKRBJRARMCX-OAQYLSRUSA-N 0.000 claims 1
- DTDJTPCUDZBRJP-JOCHJYFZSA-N (5r)-5-ethyl-5-methyl-3-[6-[(2,4,4-trimethyl-3,1-benzoxazin-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=CC2=C1C(C)(C)OC(C)=N2 DTDJTPCUDZBRJP-JOCHJYFZSA-N 0.000 claims 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims 1
- ZICPNWSAKOAKBG-UHFFFAOYSA-N 3-[2-[(3,3-dimethyl-1,4-dihydroisochromen-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=CC2=C1CC(C)(C)OC2 ZICPNWSAKOAKBG-UHFFFAOYSA-N 0.000 claims 1
- RZIJNHNNRDJJHT-UHFFFAOYSA-N 5,5-dimethyl-3-[2-(7-methylspiro[1h-2-benzofuran-3,1'-cyclobutane]-4-yl)oxypyrimidin-5-yl]imidazolidine-2,4-dione Chemical compound C1OC2(CCC2)C2=C1C(C)=CC=C2OC(N=C1)=NC=C1N1C(=O)NC(C)(C)C1=O RZIJNHNNRDJJHT-UHFFFAOYSA-N 0.000 claims 1
- JYHHQTRVJFMEGR-UHFFFAOYSA-N 5,5-dimethyl-3-[2-(7-methylspiro[2h-1-benzofuran-3,1'-cyclopropane]-4-yl)oxypyrimidin-5-yl]imidazolidine-2,4-dione Chemical compound O1CC2(CC2)C2=C1C(C)=CC=C2OC(N=C1)=NC=C1N1C(=O)NC(C)(C)C1=O JYHHQTRVJFMEGR-UHFFFAOYSA-N 0.000 claims 1
- 206010011903 Deafness traumatic Diseases 0.000 claims 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims 1
- 208000002946 Noise-Induced Hearing Loss Diseases 0.000 claims 1
- 206010036626 Presbyacusis Diseases 0.000 claims 1
- 206010061373 Sudden Hearing Loss Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 208000002982 auditory neuropathy Diseases 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 150000003931 anilides Chemical class 0.000 description 2
- JGQGPIIENVIKOT-UHFFFAOYSA-N Oc1c(C2(CC2)CO2)c2ccc1 Chemical compound Oc1c(C2(CC2)CO2)c2ccc1 JGQGPIIENVIKOT-UHFFFAOYSA-N 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
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| EP2649066B1 (en) | 2010-12-06 | 2015-10-21 | Autifony Therapeutics Limited | Hydantoin derivatives useful as kv3 inhibitors |
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| AU2012349847B2 (en) * | 2011-12-06 | 2017-02-16 | Autifony Therapeutics Limited | Hydantoin derivatives useful as Kv3 inhibitors |
| 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 |
| 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 |
| CN105829303B (zh) * | 2013-12-20 | 2018-11-06 | 吉利德科学公司 | 作为离子通道调节剂的稠合杂环化合物 |
| CA2934891C (en) | 2014-01-16 | 2023-02-28 | Nicholas Ryan DEPREZ | Pyrimidinyloxy benzene derivatives as herbicides |
| CA2942851C (en) * | 2014-03-21 | 2022-10-04 | Biotage Ab | Method and apparatus for the equilibration of a packed chromatography column |
| CN103980205B (zh) * | 2014-06-05 | 2016-01-20 | 武汉格罗宁根医药科技有限公司 | N-3-取代磺酰胺乙基-5-环丙烷螺环乙内酰脲衍生物及其制备方法和应用 |
| TWI713530B (zh) | 2015-06-05 | 2020-12-21 | 美商艾佛艾姆希公司 | 作為除草劑之嘧啶氧基苯衍生物 |
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