CA2768333A1 - 1h-quinazoline-2, 4 -diones for use in the treatment of neuronal ceroid lipofuscinosis - Google Patents
1h-quinazoline-2, 4 -diones for use in the treatment of neuronal ceroid lipofuscinosis Download PDFInfo
- Publication number
- CA2768333A1 CA2768333A1 CA2768333A CA2768333A CA2768333A1 CA 2768333 A1 CA2768333 A1 CA 2768333A1 CA 2768333 A CA2768333 A CA 2768333A CA 2768333 A CA2768333 A CA 2768333A CA 2768333 A1 CA2768333 A1 CA 2768333A1
- Authority
- CA
- Canada
- Prior art keywords
- dioxo
- dihydro
- quinazolin
- 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
- 208000002537 Neuronal Ceroid-Lipofuscinoses Diseases 0.000 title claims abstract description 56
- 201000008051 neuronal ceroid lipofuscinosis Diseases 0.000 title claims abstract description 34
- 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 8
- 230000002265 prevention Effects 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims description 85
- 229940002612 prodrug Drugs 0.000 claims description 45
- 239000000651 prodrug Substances 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 39
- 239000003814 drug Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 11
- 206010015037 epilepsy Diseases 0.000 claims description 9
- 230000000750 progressive effect Effects 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 208000036626 Mental retardation Diseases 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 230000000366 juvenile effect Effects 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 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 4
- 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 4
- 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 4
- 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 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 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 3
- 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 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 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
- 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 2
- 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 2
- 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 2
- 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 2
- 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 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
- 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 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
- 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 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
- 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
- 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
- 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
- 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
- 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
- 201000007633 neuronal ceroid lipofuscinosis 2 Diseases 0.000 claims 1
- 230000002860 competitive effect Effects 0.000 abstract description 6
- 229940098747 AMPA receptor antagonist Drugs 0.000 abstract description 2
- 239000000775 AMPA receptor antagonist Substances 0.000 abstract description 2
- 238000012360 testing method Methods 0.000 description 18
- 206010010904 Convulsion Diseases 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 230000001537 neural effect Effects 0.000 description 12
- 230000035772 mutation Effects 0.000 description 11
- 201000010099 disease Diseases 0.000 description 10
- 208000025014 late infantile neuronal ceroid lipofuscinosis Diseases 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 208000024891 symptom Diseases 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 125000004356 hydroxy functional group Chemical group O* 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
- 208000017478 adult neuronal ceroid lipofuscinosis Diseases 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
- 208000017482 infantile neuronal ceroid lipofuscinosis Diseases 0.000 description 6
- 208000017476 juvenile neuronal ceroid lipofuscinosis Diseases 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000008499 blood brain barrier function Effects 0.000 description 5
- 210000001218 blood-brain barrier Anatomy 0.000 description 5
- 230000006735 deficit Effects 0.000 description 5
- 102000003678 AMPA Receptors Human genes 0.000 description 4
- 108090000078 AMPA Receptors Proteins 0.000 description 4
- 208000031277 Amaurotic familial idiocy Diseases 0.000 description 4
- 201000004569 Blindness Diseases 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 201000007607 neuronal ceroid lipofuscinosis 3 Diseases 0.000 description 4
- 101150038645 CLN3 gene Proteins 0.000 description 3
- 241000282414 Homo sapiens Species 0.000 description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
- 206010061296 Motor dysfunction Diseases 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 208000012902 Nervous system disease Diseases 0.000 description 3
- 206010047571 Visual impairment 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
- 239000002775 capsule Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 230000034994 death Effects 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000007659 motor function Effects 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 239000000243 solution 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 206010003591 Ataxia Diseases 0.000 description 2
- 208000033001 Complex partial seizures Diseases 0.000 description 2
- 206010012289 Dementia Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 102000000079 Kainic Acid Receptors Human genes 0.000 description 2
- 108010069902 Kainic Acid Receptors Proteins 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- 208000037006 Progressive epilepsy-intellectual disability syndrome, Finnish type Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- -1 alkyl esters Alcohol Esters Chemical class 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000019771 cognition Effects 0.000 description 2
- 208000010877 cognitive disease Diseases 0.000 description 2
- 230000001149 cognitive effect Effects 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000003745 diagnosis Methods 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
- 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
- 230000001771 impaired effect Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 2
- 206010027599 migraine Diseases 0.000 description 2
- 230000007106 neurocognition Effects 0.000 description 2
- 201000007635 neuronal ceroid lipofuscinosis 8 northern epilepsy variant Diseases 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000002250 progressing effect Effects 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 210000000225 synapse Anatomy 0.000 description 2
- 230000005062 synaptic transmission Effects 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000004393 visual impairment Effects 0.000 description 2
- 102100022440 Battenin Human genes 0.000 description 1
- 101150100050 CLN2 gene Proteins 0.000 description 1
- 101150104491 CLN6 gene Proteins 0.000 description 1
- 101150047836 Cln5 gene Proteins 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- 101100391179 Dictyostelium discoideum forF gene Proteins 0.000 description 1
- 230000010777 Disulfide Reduction Effects 0.000 description 1
- 208000034308 Grand mal convulsion Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101000901683 Homo sapiens Battenin Proteins 0.000 description 1
- 101000845893 Homo sapiens DnaJ homolog subfamily C member 5 Proteins 0.000 description 1
- 101000575454 Homo sapiens Major facilitator superfamily domain-containing protein 8 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 208000015439 Lysosomal storage disease Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 101100165593 Mus musculus Bpifa5 gene Proteins 0.000 description 1
- 208000025966 Neurological disease 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
- 206010034686 Peritonsillar abscess Diseases 0.000 description 1
- 206010037211 Psychomotor hyperactivity Diseases 0.000 description 1
- 208000010340 Sleep Deprivation Diseases 0.000 description 1
- 208000006633 Tonic-Clonic Epilepsy Diseases 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 210000001056 activated astrocyte Anatomy 0.000 description 1
- 230000001154 acute effect Effects 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
- 238000004458 analytical method Methods 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003268 anti-ataxic effect Effects 0.000 description 1
- 239000002585 base Substances 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
- 229960000623 carbamazepine Drugs 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 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
- 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000005584 early death Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000003205 genotyping method Methods 0.000 description 1
- 230000009599 head growth Effects 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000006698 induction Effects 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
- 230000007794 irritation Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000004973 motor coordination Effects 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 201000007642 neuronal ceroid lipofuscinosis 1 Diseases 0.000 description 1
- 201000007640 neuronal ceroid lipofuscinosis 7 Diseases 0.000 description 1
- 201000007638 neuronal ceroid lipofuscinosis 8 Diseases 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000001331 nose Anatomy 0.000 description 1
- 239000006186 oral dosage form Substances 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
- 230000000149 penetrating effect Effects 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000007101 progressive neurodegeneration Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 108091006082 receptor inhibitors Proteins 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 230000007847 structural defect Effects 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
- 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
- 238000012956 testing procedure Methods 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
- 230000000007 visual effect Effects 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
Classifications
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US22794009P | 2009-07-23 | 2009-07-23 | |
US61/227,940 | 2009-07-23 | ||
PCT/EP2010/060733 WO2011009951A1 (en) | 2009-07-23 | 2010-07-23 | 1h-quinazoline-2, 4 -diones for use in the treatment of neuronal ceroid lipofuscinosis |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2768333A1 true CA2768333A1 (en) | 2011-01-27 |
Family
ID=42671655
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2768333A Abandoned CA2768333A1 (en) | 2009-07-23 | 2010-07-23 | 1h-quinazoline-2, 4 -diones for use in the treatment of neuronal ceroid lipofuscinosis |
Country Status (12)
Country | Link |
---|---|
US (1) | US20120122903A1 (instruction) |
EP (1) | EP2456442A1 (instruction) |
JP (1) | JP2012533605A (instruction) |
KR (1) | KR20120052341A (instruction) |
CN (1) | CN102470137A (instruction) |
AU (1) | AU2010274921B2 (instruction) |
BR (1) | BR112012001258A2 (instruction) |
CA (1) | CA2768333A1 (instruction) |
IN (1) | IN2012DN00235A (instruction) |
MX (1) | MX2012000956A (instruction) |
RU (1) | RU2012106426A (instruction) |
WO (1) | WO2011009951A1 (instruction) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2694472B1 (en) | 2011-04-05 | 2020-03-11 | Takeda Pharmaceutical Company Limited | Sulfonamide derivative and use thereof |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9400680D0 (en) * | 1994-01-14 | 1994-03-09 | Sandoz Ltd | Improvements in or relating to organic compounds |
GB0416730D0 (en) * | 2004-07-27 | 2004-09-01 | Novartis Ag | Organic compounds |
GB0507298D0 (en) * | 2005-04-11 | 2005-05-18 | Novartis Ag | Organic compounds |
-
2010
- 2010-07-23 CN CN2010800334750A patent/CN102470137A/zh active Pending
- 2010-07-23 RU RU2012106426/04A patent/RU2012106426A/ru not_active Application Discontinuation
- 2010-07-23 AU AU2010274921A patent/AU2010274921B2/en not_active Expired - Fee Related
- 2010-07-23 MX MX2012000956A patent/MX2012000956A/es not_active Application Discontinuation
- 2010-07-23 BR BR112012001258A patent/BR112012001258A2/pt not_active IP Right Cessation
- 2010-07-23 JP JP2012521055A patent/JP2012533605A/ja active Pending
- 2010-07-23 IN IN235DEN2012 patent/IN2012DN00235A/en unknown
- 2010-07-23 WO PCT/EP2010/060733 patent/WO2011009951A1/en active Application Filing
- 2010-07-23 EP EP10734746A patent/EP2456442A1/en not_active Withdrawn
- 2010-07-23 CA CA2768333A patent/CA2768333A1/en not_active Abandoned
- 2010-07-23 US US13/384,280 patent/US20120122903A1/en not_active Abandoned
- 2010-07-23 KR KR1020127004575A patent/KR20120052341A/ko not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
BR112012001258A2 (pt) | 2016-02-10 |
KR20120052341A (ko) | 2012-05-23 |
RU2012106426A (ru) | 2013-08-27 |
AU2010274921B2 (en) | 2014-08-14 |
US20120122903A1 (en) | 2012-05-17 |
AU2010274921A1 (en) | 2012-02-02 |
EP2456442A1 (en) | 2012-05-30 |
CN102470137A (zh) | 2012-05-23 |
JP2012533605A (ja) | 2012-12-27 |
IN2012DN00235A (instruction) | 2015-05-01 |
WO2011009951A1 (en) | 2011-01-27 |
MX2012000956A (es) | 2012-02-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2298295B1 (en) | Tumor necrosis factor inhibitors | |
CA2573103A1 (en) | Quinazoline modulators of hepatocyte growth factor / c-met activity for the treatment of cancer | |
ES2267715T3 (es) | Derivados aminados de dihidro-1,3,5-triazina utiles en el tratamiento de patologias asociadas al sindrome de resistencia a la insulina. | |
ES2798424T3 (es) | Compuestos de triazolopiridina y usos de estos | |
TW201020236A (en) | TRPV1 antagonists | |
CA3150465A1 (en) | Fused ring heteroaryl compounds as ripk1 inhibitors | |
CN101906105A (zh) | 吡唑并[1,5-a]嘧啶酮衍生物及其药物组合物以及其用途 | |
US20150196529A1 (en) | Use of flavone and flavanone derivatives in preparation of sedative and hypnotic drugs | |
EP3368040B1 (en) | Methods and compositions for recovery from stroke | |
US20140163050A1 (en) | Use of 1H-quinazoline-2,4-diones | |
CA2768333A1 (en) | 1h-quinazoline-2, 4 -diones for use in the treatment of neuronal ceroid lipofuscinosis | |
CN102076695A (zh) | 用于治疗骨髓增生疾病和血栓性疾病的作为阿那格雷类似物的咪唑并喹唑啉衍生物 | |
ES2973452T3 (es) | Compuesto de tetrahidro-1H-benzazepina como modulador del canal de potasio, método de preparación y uso del mismo | |
WO2019084300A1 (en) | TREATMENT OF GLIOBLASTOMA WITH FASN INHIBITORS | |
CN102066379A (zh) | 咪唑并[2,1-b]喹唑啉-2-酮衍生物及其作为血小板抗凝集剂的用途 | |
CN111372582A (zh) | 用于治疗抑郁症和偏头痛的新化合物 | |
CN102076687A (zh) | 作为血小板减少剂的取代的喹唑啉 | |
JP2023071839A (ja) | キサンチンオキシダーゼを阻害するためのヒドラジノプリン化合物及びトリアゾロプリン化合物 | |
JP5830983B2 (ja) | 抗癌剤の副作用軽減剤 | |
AU2011376333A1 (en) | Use of 1H-quinazoline- 2, 4 -diones for use in the prevention or treatment photosensitive epilepsy | |
WO2020205801A1 (en) | Treating ophthalmic disease using hypoxia-inducible factor inhibitors | |
CA3110788A1 (en) | Combination therapy for the treatment of estrogen-receptor positive breast cancer | |
RU2720510C2 (ru) | Производные кумарина, тиокумарина и хинолинона, обладающие противосудорожной активностью | |
CN120112293A (zh) | 使用sGC刺激剂治疗线粒体疾病 | |
WO2012150369A1 (es) | Derivados heterociclicos inhibidores de fosfodiesterasa 7 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FZDE | Discontinued |
Effective date: 20160725 |