CA2846503A1 - Use of 1h-quinazoline-2,4-diones for use in the prevention or treatment of photosensitive epilepsy - Google Patents
Use of 1h-quinazoline-2,4-diones for use in the prevention or treatment of photosensitive epilepsy Download PDFInfo
- Publication number
- CA2846503A1 CA2846503A1 CA2846503A CA2846503A CA2846503A1 CA 2846503 A1 CA2846503 A1 CA 2846503A1 CA 2846503 A CA2846503 A CA 2846503A CA 2846503 A CA2846503 A CA 2846503A CA 2846503 A1 CA2846503 A1 CA 2846503A1
- Authority
- CA
- Canada
- Prior art keywords
- dihydro
- quinazolin
- dioxo
- methanesulfonamide
- trifluoromethyl
- 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.)
- Abandoned
Links
- 201000003040 photosensitive epilepsy Diseases 0.000 title claims abstract description 118
- 201000005070 reflex epilepsy Diseases 0.000 title claims abstract description 69
- 238000011282 treatment Methods 0.000 title claims abstract description 65
- 230000002265 prevention Effects 0.000 title claims abstract description 24
- SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical class C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 title description 31
- 150000001875 compounds Chemical class 0.000 claims description 135
- 229940002612 prodrug Drugs 0.000 claims description 43
- 239000000651 prodrug Substances 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 36
- 239000001961 anticonvulsive agent Substances 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
- 238000009472 formulation Methods 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 230000002829 reductive effect Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- MCECSFFXUPEPDB-UHFFFAOYSA-N n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]methanesulfonamide Chemical compound CC(C)C1=CC=2NC(=O)N(NS(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1C MCECSFFXUPEPDB-UHFFFAOYSA-N 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- HBYOBTHYFIRAOW-UHFFFAOYSA-N n-[2,4-dioxo-6-(oxolan-2-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound C1=C2C(=O)N(NS(=O)(=O)C)C(=O)NC2=CC(C(F)(F)F)=C1C1CCCO1 HBYOBTHYFIRAOW-UHFFFAOYSA-N 0.000 claims 3
- LSKJPQVORRUXOV-UHFFFAOYSA-N n-[6-(1-ethoxyethyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(C)OCC)=C2 LSKJPQVORRUXOV-UHFFFAOYSA-N 0.000 claims 3
- LCFHHNPWFZWYFJ-UHFFFAOYSA-N n-[6-(1-methoxyethyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(C)OC)=C2 LCFHHNPWFZWYFJ-UHFFFAOYSA-N 0.000 claims 3
- YMFABCOTRXIHFU-UHFFFAOYSA-N n-[7-(difluoromethyl)-6-(2-methylpyrazol-3-yl)-2,4-dioxo-1h-quinazolin-3-yl]methanesulfonamide Chemical compound CN1N=CC=C1C1=CC(C(N(NS(C)(=O)=O)C(=O)N2)=O)=C2C=C1C(F)F YMFABCOTRXIHFU-UHFFFAOYSA-N 0.000 claims 3
- OEKIBARTEOJEKR-UHFFFAOYSA-N n-[7-ethyl-6-(2-methylpyrazol-3-yl)-2,4-dioxo-1h-quinazolin-3-yl]methanesulfonamide Chemical compound CCC1=CC=2NC(=O)N(NS(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1C OEKIBARTEOJEKR-UHFFFAOYSA-N 0.000 claims 3
- DSELHYJGEKXXRP-UHFFFAOYSA-N n-[2,4-dioxo-6-(1-propan-2-yloxyethyl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(C)OC(C)C)=C2 DSELHYJGEKXXRP-UHFFFAOYSA-N 0.000 claims 2
- WUTUFPNWYUNDFI-UHFFFAOYSA-N n-[2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound CC(C)N1N=CC=C1C1=CC(C(N(NS(C)(=O)=O)C(=O)N2)=O)=C2C=C1C(F)(F)F WUTUFPNWYUNDFI-UHFFFAOYSA-N 0.000 claims 2
- MIGNZRPDULLXTQ-UHFFFAOYSA-N n-[6-(1-hydroxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(O)CC)=C2 MIGNZRPDULLXTQ-UHFFFAOYSA-N 0.000 claims 2
- QLUSFZJXGQYNMK-UHFFFAOYSA-N n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound CN1N=CC=C1C1=CC(C(N(NS(C)(=O)=O)C(=O)N2)=O)=C2C=C1C(F)(F)F QLUSFZJXGQYNMK-UHFFFAOYSA-N 0.000 claims 2
- ZWDLCWUDNRHDGU-UHFFFAOYSA-N n-[7-(1,1-difluoroethyl)-6-(2-methylpyrazol-3-yl)-2,4-dioxo-1h-quinazolin-3-yl]methanesulfonamide Chemical compound CN1N=CC=C1C1=CC(C(N(NS(C)(=O)=O)C(=O)N2)=O)=C2C=C1C(C)(F)F ZWDLCWUDNRHDGU-UHFFFAOYSA-N 0.000 claims 2
- JVPVBPHLIBMROY-UHFFFAOYSA-N n-[7-(difluoromethyl)-2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound CC(C)N1N=CC=C1C1=CC(C(N(NS(C)(=O)=O)C(=O)N2)=O)=C2C=C1C(F)F JVPVBPHLIBMROY-UHFFFAOYSA-N 0.000 claims 2
- HSGNDJYOXXCRGB-UHFFFAOYSA-N n-[7-(fluoromethyl)-2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound CC(C)N1N=CC=C1C1=CC(C(N(NS(C)(=O)=O)C(=O)N2)=O)=C2C=C1CF HSGNDJYOXXCRGB-UHFFFAOYSA-N 0.000 claims 2
- FCGZKGLYOHESAU-UHFFFAOYSA-N n-[2,4-dioxo-6-(1-propan-2-yloxypropyl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(OC(C)C)CC)=C2 FCGZKGLYOHESAU-UHFFFAOYSA-N 0.000 claims 1
- NXSCFPKPPNHCCN-UHFFFAOYSA-N n-[2,4-dioxo-6-(1-propoxyethyl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(C)OCCC)=C2 NXSCFPKPPNHCCN-UHFFFAOYSA-N 0.000 claims 1
- NZWSWGBRWWTWJP-UHFFFAOYSA-N n-[2,4-dioxo-6-(1-propoxypropyl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(CC)OCCC)=C2 NZWSWGBRWWTWJP-UHFFFAOYSA-N 0.000 claims 1
- KBYZURXFFPMEEI-UHFFFAOYSA-N n-[2,4-dioxo-6-(oxolan-3-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound C1=C2C(=O)N(NS(=O)(=O)C)C(=O)NC2=CC(C(F)(F)F)=C1C1CCOC1 KBYZURXFFPMEEI-UHFFFAOYSA-N 0.000 claims 1
- WMLSFJLHWQYACM-UHFFFAOYSA-N n-[2,4-dioxo-7-propan-2-yl-6-(2-propan-2-ylpyrazol-3-yl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound CC(C)C1=CC=2NC(=O)N(NS(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1C(C)C WMLSFJLHWQYACM-UHFFFAOYSA-N 0.000 claims 1
- OFJHQRJECRDHRW-UHFFFAOYSA-N n-[6-(1-butoxyethyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(C)OCCCC)=C2 OFJHQRJECRDHRW-UHFFFAOYSA-N 0.000 claims 1
- RVFCUKBZUNLKHH-UHFFFAOYSA-N n-[6-(1-cyclopentyloxyethyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound C=1C(C(N(NS(C)(=O)=O)C(=O)N2)=O)=C2C=C(C(F)(F)F)C=1C(C)OC1CCCC1 RVFCUKBZUNLKHH-UHFFFAOYSA-N 0.000 claims 1
- MMTLKGVPYZLJTG-UHFFFAOYSA-N n-[6-(1-ethoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(CC)OCC)=C2 MMTLKGVPYZLJTG-UHFFFAOYSA-N 0.000 claims 1
- MWEPLWMITBXDHS-UHFFFAOYSA-N n-[6-(1-hydroxy-2-methylpropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(O)C(C)C)=C2 MWEPLWMITBXDHS-UHFFFAOYSA-N 0.000 claims 1
- QDIISXGZVBGRKE-UHFFFAOYSA-N n-[6-(1-hydroxy-3-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(O)CCOC)=C2 QDIISXGZVBGRKE-UHFFFAOYSA-N 0.000 claims 1
- UQTXIYMVGFQNKE-UHFFFAOYSA-N n-[6-(1-hydroxybutyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(O)CCC)=C2 UQTXIYMVGFQNKE-UHFFFAOYSA-N 0.000 claims 1
- IOMNVPHVACWAQD-UHFFFAOYSA-N n-[6-(1-hydroxyethyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(O)C)=C2 IOMNVPHVACWAQD-UHFFFAOYSA-N 0.000 claims 1
- QNOGGNMZYXNFMK-UHFFFAOYSA-N n-[6-(1-methoxy-2-methylpropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(C(C)C)OC)=C2 QNOGGNMZYXNFMK-UHFFFAOYSA-N 0.000 claims 1
- QDNJESWDNWORKP-UHFFFAOYSA-N n-[6-(1-methoxybutyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(OC)CCC)=C2 QDNJESWDNWORKP-UHFFFAOYSA-N 0.000 claims 1
- DKMLPACXXYKYSU-UHFFFAOYSA-N n-[6-(2-hydroxypyrazol-3-yl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound C1=C2C(=O)N(NS(=O)(=O)C)C(=O)NC2=CC(C(F)(F)F)=C1C1=CC=NN1O DKMLPACXXYKYSU-UHFFFAOYSA-N 0.000 claims 1
- CZVNRIDLEZRQFH-UHFFFAOYSA-N n-[6-(3-hydroxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound FC(F)(F)C1=C(CCCO)C=C2C(=O)N(NS(=O)(=O)C)C(=O)NC2=C1 CZVNRIDLEZRQFH-UHFFFAOYSA-N 0.000 claims 1
- NMIQVXYXYPUJHC-UHFFFAOYSA-N n-[6-(oxan-2-yl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound C1=C2C(=O)N(NS(=O)(=O)C)C(=O)NC2=CC(C(F)(F)F)=C1C1CCCCO1 NMIQVXYXYPUJHC-UHFFFAOYSA-N 0.000 claims 1
- USURBQLTQADVAD-UHFFFAOYSA-N n-[6-[1-(2-methylpropoxy)ethyl]-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(C)OCC(C)C)=C2 USURBQLTQADVAD-UHFFFAOYSA-N 0.000 claims 1
- AZAOVWWNNFAHAG-UHFFFAOYSA-N n-[6-[2-(2-methoxyethyl)pyrazol-3-yl]-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound COCCN1N=CC=C1C1=CC(C(N(NS(C)(=O)=O)C(=O)N2)=O)=C2C=C1C(F)(F)F AZAOVWWNNFAHAG-UHFFFAOYSA-N 0.000 claims 1
- JVZQDMCKWPOOIY-UHFFFAOYSA-N n-[6-[2-(2-methoxyethyl)pyrazol-3-yl]-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]methanesulfonamide Chemical compound COCCN1N=CC=C1C1=CC(C(N(NS(C)(=O)=O)C(=O)N2)=O)=C2C=C1C(C)C JVZQDMCKWPOOIY-UHFFFAOYSA-N 0.000 claims 1
- OPYMZVLVOCASOX-UHFFFAOYSA-N n-[7-(1,1-difluoroethyl)-2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound CC(C)N1N=CC=C1C1=CC(C(N(NS(C)(=O)=O)C(=O)N2)=O)=C2C=C1C(C)(F)F OPYMZVLVOCASOX-UHFFFAOYSA-N 0.000 claims 1
- FDHRJKWFUHLAFO-UHFFFAOYSA-N n-[7-(1-fluoroethyl)-2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound CC(C)N1N=CC=C1C1=CC(C(N(NS(C)(=O)=O)C(=O)N2)=O)=C2C=C1C(C)F FDHRJKWFUHLAFO-UHFFFAOYSA-N 0.000 claims 1
- MMKXICJSNZKSDT-UHFFFAOYSA-N n-[7-(1-fluoroethyl)-6-(2-methylpyrazol-3-yl)-2,4-dioxo-1h-quinazolin-3-yl]methanesulfonamide Chemical compound CC(F)C1=CC=2NC(=O)N(NS(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1C MMKXICJSNZKSDT-UHFFFAOYSA-N 0.000 claims 1
- ISBCBAUWMPBZMW-UHFFFAOYSA-N n-[7-(difluoromethyl)-6-(1-ethoxyethyl)-2,4-dioxo-1h-quinazolin-3-yl]methanesulfonamide Chemical compound N1C(=O)N(NS(C)(=O)=O)C(=O)C2=C1C=C(C(F)F)C(C(C)OCC)=C2 ISBCBAUWMPBZMW-UHFFFAOYSA-N 0.000 claims 1
- XWWOWSFUSLLOTP-UHFFFAOYSA-N n-[7-(fluoromethyl)-6-(2-methylpyrazol-3-yl)-2,4-dioxo-1h-quinazolin-3-yl]methanesulfonamide Chemical compound CN1N=CC=C1C1=CC(C(N(NS(C)(=O)=O)C(=O)N2)=O)=C2C=C1CF XWWOWSFUSLLOTP-UHFFFAOYSA-N 0.000 claims 1
- KEEFXFPTFSCWQH-UHFFFAOYSA-N n-[7-ethyl-2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-1h-quinazolin-3-yl]methanesulfonamide Chemical compound CCC1=CC=2NC(=O)N(NS(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1C(C)C KEEFXFPTFSCWQH-UHFFFAOYSA-N 0.000 claims 1
- KPWVCITWUDVCGS-UHFFFAOYSA-N n-[7-ethyl-6-(2-ethylpyrazol-3-yl)-2,4-dioxo-1h-quinazolin-3-yl]methanesulfonamide Chemical compound CCC1=CC=2NC(=O)N(NS(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1CC KPWVCITWUDVCGS-UHFFFAOYSA-N 0.000 claims 1
- 230000002860 competitive effect Effects 0.000 abstract description 7
- 229940098747 AMPA receptor antagonist Drugs 0.000 abstract description 3
- 239000000775 AMPA receptor antagonist Substances 0.000 abstract description 3
- 230000009467 reduction Effects 0.000 description 48
- 230000001629 suppression Effects 0.000 description 41
- 230000000694 effects Effects 0.000 description 34
- 206010010904 Convulsion Diseases 0.000 description 31
- 229940079593 drug Drugs 0.000 description 18
- 230000004044 response Effects 0.000 description 17
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 16
- 229960003965 antiepileptics Drugs 0.000 description 13
- AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 12
- 229940102566 valproate Drugs 0.000 description 12
- 206010015037 epilepsy Diseases 0.000 description 11
- 229960001848 lamotrigine Drugs 0.000 description 11
- PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 description 11
- 241000282414 Homo sapiens Species 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- 229960004002 levetiracetam Drugs 0.000 description 8
- HPHUVLMMVZITSG-ZCFIWIBFSA-N levetiracetam Chemical compound CC[C@H](C(N)=O)N1CCCC1=O HPHUVLMMVZITSG-ZCFIWIBFSA-N 0.000 description 8
- KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical compound C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 7
- 230000000638 stimulation Effects 0.000 description 7
- 229960004394 topiramate Drugs 0.000 description 7
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 description 6
- 230000009471 action Effects 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
- 230000002354 daily effect Effects 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- -1 C-12 Chemical compound 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000008499 blood brain barrier function Effects 0.000 description 5
- 210000001218 blood-brain barrier Anatomy 0.000 description 5
- 230000000007 visual effect Effects 0.000 description 5
- 229960002911 zonisamide Drugs 0.000 description 5
- UBQNRHZMVUUOMG-UHFFFAOYSA-N zonisamide Chemical compound C1=CC=C2C(CS(=O)(=O)N)=NOC2=C1 UBQNRHZMVUUOMG-UHFFFAOYSA-N 0.000 description 5
- 102000003678 AMPA Receptors Human genes 0.000 description 4
- 108090000078 AMPA Receptors Proteins 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 238000013103 analytical ultracentrifugation Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- CXOXHMZGEKVPMT-UHFFFAOYSA-N clobazam Chemical compound O=C1CC(=O)N(C)C2=CC=C(Cl)C=C2N1C1=CC=CC=C1 CXOXHMZGEKVPMT-UHFFFAOYSA-N 0.000 description 4
- 229960001403 clobazam Drugs 0.000 description 4
- 238000003745 diagnosis Methods 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 230000004399 eye closure Effects 0.000 description 4
- 230000003285 pharmacodynamic effect Effects 0.000 description 4
- 230000036470 plasma concentration Effects 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 238000012216 screening Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
- 208000012902 Nervous system disease Diseases 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000011260 co-administration Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229930195712 glutamate Natural products 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000036211 photosensitivity Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 208000025966 Neurological disease Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 235000021152 breakfast Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 230000035622 drinking Effects 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000009510 drug design Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000001037 epileptic effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229940080466 lamotrigine 100 mg Drugs 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000000902 placebo Substances 0.000 description 2
- 229940068196 placebo Drugs 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 210000000225 synapse Anatomy 0.000 description 2
- 230000005062 synaptic transmission Effects 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 208000024255 Audiogenic seizures Diseases 0.000 description 1
- 101100478232 Caenorhabditis elegans spr-3 gene Proteins 0.000 description 1
- 208000032170 Congenital Abnormalities Diseases 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- 230000010777 Disulfide Reduction Effects 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000002877 Epileptic Syndromes Diseases 0.000 description 1
- 208000003078 Generalized Epilepsy Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 102000000079 Kainic Acid Receptors Human genes 0.000 description 1
- 108010069902 Kainic Acid Receptors Proteins 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 238000011795 OF1 mouse Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010061334 Partial seizures Diseases 0.000 description 1
- 206010071141 Rasmussen encephalitis Diseases 0.000 description 1
- 208000004160 Rasmussen subacute encephalitis Diseases 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- 208000006633 Tonic-Clonic Epilepsy Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 210000001056 activated astrocyte Anatomy 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000003281 allosteric effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- 150000001607 bioavailable molecules Chemical class 0.000 description 1
- 230000007698 birth defect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229960000623 carbamazepine Drugs 0.000 description 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000013498 data listing Methods 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000008406 drug-drug interaction Effects 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000000537 electroencephalography Methods 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 208000028329 epileptic seizure Diseases 0.000 description 1
- 230000001787 epileptiform Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229960002870 gabapentin Drugs 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000036963 noncompetitive effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000771 oncological effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007833 oxidative deamination reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000013610 patient sample Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920005630 polypropylene random copolymer Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 229960001233 pregabalin Drugs 0.000 description 1
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 108091006082 receptor inhibitors Proteins 0.000 description 1
- 229940127558 rescue medication Drugs 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000021317 sensory perception Effects 0.000 description 1
- 231100000748 severe hepatic injury Toxicity 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 208000005809 status epilepticus Diseases 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 208000028325 tonic-clonic seizure Diseases 0.000 description 1
- 229940097017 topiramate 100 mg Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 229940004662 zonisamide 100 mg Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2011/050687 WO2013036224A1 (en) | 2011-09-07 | 2011-09-07 | Use of 1h-quinazoline- 2, 4 -diones for use in the prevention or treatment photosensitive epilepsy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2846503A1 true CA2846503A1 (en) | 2013-03-14 |
Family
ID=44652020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2846503A Abandoned CA2846503A1 (en) | 2011-09-07 | 2011-09-07 | Use of 1h-quinazoline-2,4-diones for use in the prevention or treatment of photosensitive epilepsy |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP2753331A1 (instruction) |
| JP (1) | JP2014525474A (instruction) |
| KR (1) | KR20140071405A (instruction) |
| CN (1) | CN103889427A (instruction) |
| AU (1) | AU2011376333A1 (instruction) |
| BR (1) | BR112014005210A2 (instruction) |
| CA (1) | CA2846503A1 (instruction) |
| IN (1) | IN2014DN01791A (instruction) |
| MX (1) | MX2014002693A (instruction) |
| WO (1) | WO2013036224A1 (instruction) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201609719A (zh) * | 2014-05-28 | 2016-03-16 | 美國禮來大藥廠 | 作為ＴＡＲＰ－γ８依賴性ＡＭＰＡ受體拮抗劑之６－經取代－３Ｈ－１，３－苯并噻唑－２－酮化合物 |
| MX2018008021A (es) | 2015-12-30 | 2018-11-09 | Adamas Pharmaceuticals Inc | Metodos y composiciones para el tratamiento de trastornos relacionados con convulsiones. |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0128996D0 (en) | 2001-12-04 | 2002-01-23 | Novartis Ag | Organic compounds |
| SE0201943D0 (sv) | 2002-06-20 | 2002-06-20 | Astrazeneca Ab | New use |
| EP1677789A1 (en) | 2003-10-31 | 2006-07-12 | AstraZeneca AB | Alkynes i |
| EP1677788A1 (en) | 2003-10-31 | 2006-07-12 | AstraZeneca AB | Alkynes iii |
| CA2549969A1 (en) | 2003-10-31 | 2005-05-19 | Astrazeneca Ab | Alkynes ii |
| CN1933838A (zh) | 2004-02-12 | 2007-03-21 | 默克公司 | 作为代谢型谷氨酸受体－5调节剂的联吡啶酰胺 |
| GB0507298D0 (en) | 2005-04-11 | 2005-05-18 | Novartis Ag | Organic compounds |
| GB0508319D0 (en) | 2005-04-25 | 2005-06-01 | Novartis Ag | Organic compounds |
| KR20080076962A (ko) | 2005-12-20 | 2008-08-20 | 노파르티스 아게 | 대사성 글루타메이트 수용체 조절제로서의 니코틴산 유도체 |
| AU2010316600A1 (en) * | 2009-11-03 | 2012-05-31 | Lupin Limited | Modified release formulation of lacosamide |
-
2011
- 2011-09-07 KR KR1020147008752A patent/KR20140071405A/ko not_active Withdrawn
- 2011-09-07 CA CA2846503A patent/CA2846503A1/en not_active Abandoned
- 2011-09-07 WO PCT/US2011/050687 patent/WO2013036224A1/en active Application Filing
- 2011-09-07 JP JP2014529647A patent/JP2014525474A/ja not_active Withdrawn
- 2011-09-07 CN CN201180073318.7A patent/CN103889427A/zh active Pending
- 2011-09-07 MX MX2014002693A patent/MX2014002693A/es not_active Application Discontinuation
- 2011-09-07 EP EP11757513.4A patent/EP2753331A1/en not_active Withdrawn
- 2011-09-07 AU AU2011376333A patent/AU2011376333A1/en not_active Abandoned
- 2011-09-07 BR BR112014005210A patent/BR112014005210A2/pt not_active IP Right Cessation
- 2011-09-07 IN IN1791DEN2014 patent/IN2014DN01791A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20140071405A (ko) | 2014-06-11 |
| AU2011376333A1 (en) | 2014-03-13 |
| CN103889427A (zh) | 2014-06-25 |
| IN2014DN01791A (instruction) | 2015-05-15 |
| WO2013036224A1 (en) | 2013-03-14 |
| BR112014005210A2 (pt) | 2017-03-21 |
| MX2014002693A (es) | 2014-06-04 |
| EP2753331A1 (en) | 2014-07-16 |
| JP2014525474A (ja) | 2014-09-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6861764B2 (ja) | 軸索再生および神経機能を促進するための方法および組成物 | |
| TWI353835B (en) | Novel methods for identifying improved, non-sedati | |
| US10111889B2 (en) | Uses of ganaxolone | |
| Rogawski et al. | Preclinical pharmacology of perampanel, a selective non‐competitive AMPA receptor antagonist | |
| WO2009005771A1 (en) | A drug demonstrating anxiolytic effect based on hydrogenated pyrido (4, 3-b) indoles, its pharmacological compound and application method | |
| US7226949B2 (en) | Compounds of use in the treatment of epilepsy, seizure, and electroconvulsive disorders | |
| CA2674460C (en) | 3-substituted-h.2.31-benzotriazinone compound for enhancing glutamatergic synaptic responses | |
| US20140163050A1 (en) | Use of 1H-quinazoline-2,4-diones | |
| US12208079B2 (en) | Enantiomers of A2-73, analogues, and sigma agonist activity | |
| KR20170048541A (ko) | 스미스 마제니스 증후군을 치료하기 위한 타시멜테온 | |
| CA2846503A1 (en) | Use of 1h-quinazoline-2,4-diones for use in the prevention or treatment of photosensitive epilepsy | |
| EA023728B1 (ru) | Терапевтическое средство от тревожных расстройств | |
| Herrling et al. | D-CPPene (SDZ EAA-494)—a competitive NMDA antagonist: pharmacology and results in humans | |
| BR112021004938A2 (pt) | métodos e composições para tratamento de danos associados com o envelhecimento usando inibidores de ccr3 | |
| CN111050800A (zh) | 血清素3受体激动剂对疼痛的治疗 | |
| JP2005314347A (ja) | 疼痛抑制剤 | |
| KR20120052341A (ko) | 신경 세로이드 리포푸스신증의 치료에 사용하기 위한 1ｈ-퀴나졸린-2,4-디온 | |
| Hemanthkumar | Study of anticonvulsant activity of acetazolamide on albino rats and its influence on anticonvulsant activity of sodium valproate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20160908 |