SK280578B6 - Derivát izatinoxímu, spôsob jeho prípravy, farmace - Google Patents
Derivát izatinoxímu, spôsob jeho prípravy, farmace Download PDFInfo
- Publication number
- SK280578B6 SK280578B6 SK238-94A SK23894A SK280578B6 SK 280578 B6 SK280578 B6 SK 280578B6 SK 23894 A SK23894 A SK 23894A SK 280578 B6 SK280578 B6 SK 280578B6
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- isatinoxime
- branched
- formula
- derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000003814 drug Substances 0.000 title claims abstract 5
- ISRAAHLLSDMDOI-UHFFFAOYSA-N 1-hydroxyindole-2,3-dione Chemical class C1=CC=C2N(O)C(=O)C(=O)C2=C1 ISRAAHLLSDMDOI-UHFFFAOYSA-N 0.000 title 1
- NGXLTYPELAIUHE-UHFFFAOYSA-N 2-(hydroxyamino)indol-3-one Chemical class C1=CC=C2C(=O)C(NO)=NC2=C1 NGXLTYPELAIUHE-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000004122 cyclic group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- OZDAOHVKBFBBMZ-UHFFFAOYSA-N 2-aminopentanedioic acid;hydrate Chemical compound O.OC(=O)C(N)CCC(O)=O OZDAOHVKBFBBMZ-UHFFFAOYSA-N 0.000 claims description 6
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 6
- 108010011562 aspartic acid receptor Proteins 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 230000000903 blocking effect Effects 0.000 claims description 6
- 235000013922 glutamic acid Nutrition 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000008177 pharmaceutical agent Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 12
- -1 hydroxyimino Chemical group 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 230000002461 excitatory amino acid Effects 0.000 description 10
- 239000003257 excitatory amino acid Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229940124530 sulfonamide Drugs 0.000 description 9
- UUDAMDVQRQNNHZ-UHFFFAOYSA-N (S)-AMPA Chemical compound CC=1ONC(=O)C=1CC(N)C(O)=O UUDAMDVQRQNNHZ-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 206010010904 Convulsion Diseases 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZPHQBFRCXUIIAZ-UHFFFAOYSA-N benzene;hydrochloride Chemical compound Cl.C1=CC=CC=C1 ZPHQBFRCXUIIAZ-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 208000019901 Anxiety disease Diseases 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 230000036506 anxiety Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- IQGHMTSQJHRRFH-UHFFFAOYSA-N 1,2-bis(bromomethyl)-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(CBr)=C1CBr IQGHMTSQJHRRFH-UHFFFAOYSA-N 0.000 description 4
- 206010053398 Clonic convulsion Diseases 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HXTWAFNCOABMPL-UHFFFAOYSA-N 5-nitro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=C1C=CC=C2[N+](=O)[O-] HXTWAFNCOABMPL-UHFFFAOYSA-N 0.000 description 3
- RUFVVFCAFDRGEI-UHFFFAOYSA-N 6-amino-1-benzazepin-2-one Chemical compound O=C1C=CC=C2C(N)=CC=CC2=N1 RUFVVFCAFDRGEI-UHFFFAOYSA-N 0.000 description 3
- HOUSCZVHLDNRHI-UHFFFAOYSA-N 6-nitro-1-benzazepin-2-one Chemical compound O=C1C=CC=C2C([N+](=O)[O-])=CC=CC2=N1 HOUSCZVHLDNRHI-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical class C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 3
- 239000004323 potassium nitrate Substances 0.000 description 3
- 235000010333 potassium nitrate Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 2
- 238000011785 NMRI mouse Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 206010008118 cerebral infarction Diseases 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- 230000001037 epileptic effect Effects 0.000 description 2
- 230000003492 excitotoxic effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 201000000980 schizophrenia Diseases 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 description 1
- YOUJYVLWDDOAIO-UHFFFAOYSA-N 1,3-dihydro-2-benzofuran-4-amine;hydrochloride Chemical compound Cl.NC1=CC=CC2=C1COC2 YOUJYVLWDDOAIO-UHFFFAOYSA-N 0.000 description 1
- ZGAOPGLRQCWPBI-UHFFFAOYSA-N 1,3-dihydro-2-benzothiophen-4-amine Chemical compound NC1=CC=CC2=C1CSC2 ZGAOPGLRQCWPBI-UHFFFAOYSA-N 0.000 description 1
- DYGRWMDWDGCGRN-UHFFFAOYSA-N 1,8-dihydrofuro[3,4-g]indole-2,3,6-trione Chemical compound C1=C2C(=O)C(=O)NC2=C2COC(=O)C2=C1 DYGRWMDWDGCGRN-UHFFFAOYSA-N 0.000 description 1
- ZFSYJCQFOKJSFE-UHFFFAOYSA-N 1-(7-amino-2,3-dihydroindol-1-yl)ethanone Chemical compound C1=CC(N)=C2N(C(=O)C)CCC2=C1 ZFSYJCQFOKJSFE-UHFFFAOYSA-N 0.000 description 1
- USNYHYIHBMWMND-UHFFFAOYSA-N 2-amino-3-(3-hydroxy-5-methyl-2h-1,2-oxazol-3-yl)propanoic acid Chemical compound CC1=CC(O)(CC(N)C(O)=O)NO1 USNYHYIHBMWMND-UHFFFAOYSA-N 0.000 description 1
- OXWNTTVDTPIYRD-UHFFFAOYSA-N 2-methyl-3,4-dihydro-1h-isoquinolin-5-amine Chemical compound C1=CC=C2CN(C)CCC2=C1N OXWNTTVDTPIYRD-UHFFFAOYSA-N 0.000 description 1
- OMYBCESXCXGOTB-UHFFFAOYSA-N 3-(hydroxyamino)-6,8-dihydrothieno[3,4-g]indol-2-one Chemical compound C1=C2C(=NO)C(=O)NC2=C2CSCC2=C1 OMYBCESXCXGOTB-UHFFFAOYSA-N 0.000 description 1
- LNMAXZZQNSPQSR-UHFFFAOYSA-N 3-(hydroxyamino)indol-2-one Chemical compound C1=CC=CC2=NC(=O)C(NO)=C21 LNMAXZZQNSPQSR-UHFFFAOYSA-N 0.000 description 1
- ATTGVJKDTAIHEA-UHFFFAOYSA-N 5-amino-1,2,4,5-tetrahydro-2,4-benzodiazepin-3-one Chemical compound NC1NC(=O)NCC2=CC=CC=C12 ATTGVJKDTAIHEA-UHFFFAOYSA-N 0.000 description 1
- SIYJOMQIFZIUHY-UHFFFAOYSA-N 6,7,9,10-tetrahydro-1h-pyrrolo[3,2-i][2,4]benzodiazepine-2,3,8-trione Chemical compound C1NC(=O)NCC2=C1C=CC1=C2NC(=O)C1=O SIYJOMQIFZIUHY-UHFFFAOYSA-N 0.000 description 1
- GFJBIAKPGHASFW-UHFFFAOYSA-N 6,8-dihydro-1h-furo[3,4-g]indole-2,3-dione Chemical compound C1=C2C(=O)C(=O)NC2=C2COCC2=C1 GFJBIAKPGHASFW-UHFFFAOYSA-N 0.000 description 1
- GBSLETGIPVUDIO-UHFFFAOYSA-N 7-acetyl-3-(hydroxyamino)-5-nitro-8,9-dihydro-6h-pyrrolo[2,3-f]isoquinolin-2-one Chemical compound [O-][N+](=O)C1=C2CN(C(=O)C)CCC2=C2NC(=O)C(=NO)C2=C1 GBSLETGIPVUDIO-UHFFFAOYSA-N 0.000 description 1
- WNZLAONIDDPJJV-UHFFFAOYSA-N 7-acetyl-3-(hydroxyamino)-8,9-dihydro-6h-pyrrolo[2,3-f]isoquinolin-2-one Chemical compound C1=C2CN(C(=O)C)CCC2=C2NC(=O)C(=NO)C2=C1 WNZLAONIDDPJJV-UHFFFAOYSA-N 0.000 description 1
- VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical class [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PVAFTPFFPGLNRV-UHFFFAOYSA-N Cl.O=C1CCCO1 Chemical compound Cl.O=C1CCCO1 PVAFTPFFPGLNRV-UHFFFAOYSA-N 0.000 description 1
- 206010013647 Drowning Diseases 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 102000000079 Kainic Acid Receptors Human genes 0.000 description 1
- 108010069902 Kainic Acid Receptors Proteins 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- FCLZCOCSZQNREK-UHFFFAOYSA-N Pyrrolidine, hydrochloride Chemical compound Cl.C1CCNC1 FCLZCOCSZQNREK-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000030886 Traumatic Brain injury Diseases 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003194 amino acid receptor blocking agent Substances 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- DBKKFIIYQGGHJO-UHFFFAOYSA-N diethyl 2-oxopropanedioate Chemical compound CCOC(=O)C(=O)C(=O)OCC DBKKFIIYQGGHJO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- BRPMKDLMTJBMTQ-UHFFFAOYSA-N ethyl 2-[3-(hydroxyamino)-2-oxo-8,9-dihydro-6h-pyrrolo[2,3-f]isoquinolin-7-yl]acetate Chemical compound C1=C2CN(CC(=O)OCC)CCC2=C2NC(=O)C(=NO)C2=C1 BRPMKDLMTJBMTQ-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000010006 flight Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002008 hemorrhagic effect Effects 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000000185 intracerebroventricular administration Methods 0.000 description 1
- 208000001286 intracranial vasospasm Diseases 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 230000016273 neuron death Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 230000009424 thromboembolic effect Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Medicinal Preparation (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75116591A | 1991-08-28 | 1991-08-28 | |
| US83185192A | 1992-02-05 | 1992-02-05 | |
| PCT/EP1992/001999 WO1993005043A1 (en) | 1991-08-28 | 1992-08-27 | Novel isatinoxime derivatives, their preparation and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK23894A3 SK23894A3 (en) | 1994-12-07 |
| SK280578B6 true SK280578B6 (sk) | 2000-04-10 |
Family
ID=27115380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK238-94A SK280578B6 (sk) | 1991-08-28 | 1992-08-27 | Derivát izatinoxímu, spôsob jeho prípravy, farmace |
Country Status (18)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2109516T3 (es) | 1992-10-13 | 1998-01-16 | Warner Lambert Co | Derivados de quinoxalinodiona como antagonistas de aminoacidos excitadores. |
| NZ267081A (en) * | 1993-05-13 | 1997-11-24 | Neurosearch As | Hetero-fused indole and quinoxaline compounds and medicaments thereof |
| US5843945A (en) * | 1993-05-13 | 1998-12-01 | Neurosearch A/S | AMPA antagonists and a method of treatment |
| DK81593D0 (da) * | 1993-07-07 | 1993-07-07 | Neurosearch As | Nye isatinoximderivater, deres fremstilling og anvendelse |
| AU687255B2 (en) * | 1994-09-14 | 1998-02-19 | Neurosearch A/S | Indole-2,3-dione-3-oxime derivatives, their preparation and use |
| JP3164372B2 (ja) * | 1994-09-14 | 2001-05-08 | ノイロサーチ アクティーゼルスカブ | 融合インドール及びキノキサリン誘導体、その製造および使用 |
| UA54403C2 (uk) * | 1996-10-01 | 2003-03-17 | Н'Юросерч А/С | Похідні індол-2,3-діон-3-оксиму, фармацевтична композиція, спосіб лікування розладу чи захворювання ссавців, у тому числі людини та спосіб одержання похідних індол-2,3-діон-3-оксиму |
| FR2768624B1 (fr) | 1997-09-25 | 1999-11-12 | Oreal | Utilisation d'un inhibiteur d'acides amines excitateurs dans une composition cosmetique ou dermatologique pour peaux sensibles et composition obtenue |
| WO2000071102A2 (en) * | 1999-05-19 | 2000-11-30 | Neurosearch A/S | Inhibitors of proton-gated cation channels and their use in the treatment of ischaemic disorders |
| EP1736468A3 (en) | 2000-01-24 | 2007-01-03 | NeuroSearch A/S | Isatin derivatives with neurotrophic activity useful in the treatment of diseases mediated by the nerve growth factor (NGF) activation |
| US7250422B2 (en) | 2002-10-29 | 2007-07-31 | Sungkyunkwan University | Pharmaceutical composition containing berberine as effective ingredient for preventing and treating addiction or tolerance to morphine |
| KR20080070749A (ko) | 2005-11-23 | 2008-07-30 | 페인셉터 파마 코포레이션 | 개폐 이온 통로를 조절하기 위한 조성물 및 방법 |
| MX2015007710A (es) * | 2012-12-19 | 2015-09-23 | Bayer Cropscience Ag | Indanilcarboxamidas difluorometil-nicotinicas. |
| WO2015129592A1 (ja) * | 2014-02-28 | 2015-09-03 | 住友化学株式会社 | ２－（ハロゲノメチル）－３－メチルニトロベンゼンの製造方法 |
| PL3429352T3 (pl) | 2016-03-17 | 2022-08-22 | Fmc Corporation | Sposób konwersji enancjomeru-S do jego postaci racemicznej |
| CN109776451B (zh) * | 2017-11-15 | 2020-12-11 | 中山光禾医疗科技有限公司 | 光交联水凝胶材料的制备、原料、产品及应用 |
| CN108912127B (zh) * | 2018-08-27 | 2019-12-10 | 青岛农业大学 | 一种基于靛红骨架的苯并[b,e]氮杂卓化合物及其制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE69677B1 (en) * | 1989-12-11 | 1996-10-02 | Neurosearch As | Isatine derivatives their preparation and use |
-
1992
- 1992-08-26 CA CA002076948A patent/CA2076948C/en not_active Expired - Fee Related
- 1992-08-26 MX MX9204914A patent/MX9204914A/es not_active IP Right Cessation
- 1992-08-27 KR KR1019940700676A patent/KR100277481B1/ko not_active Expired - Fee Related
- 1992-08-27 HU HU9400595A patent/HUT70753A/hu unknown
- 1992-08-27 JP JP50493393A patent/JP3170584B2/ja not_active Expired - Fee Related
- 1992-08-27 SK SK238-94A patent/SK280578B6/sk unknown
- 1992-08-27 GE GEAP19922683A patent/GEP20002329B/en unknown
- 1992-08-27 RU RU94019425/04A patent/RU2114827C1/ru not_active IP Right Cessation
- 1992-08-27 CZ CZ94395A patent/CZ282759B6/cs not_active IP Right Cessation
- 1992-08-27 PL PL92302584A patent/PL170920B1/pl unknown
- 1992-08-27 EP EP92114654A patent/EP0529636B1/en not_active Expired - Lifetime
- 1992-08-27 AU AU24820/92A patent/AU655672B2/en not_active Ceased
- 1992-08-27 DE DE69229461T patent/DE69229461T2/de not_active Expired - Lifetime
- 1992-08-27 WO PCT/EP1992/001999 patent/WO1993005043A1/en not_active Ceased
- 1992-08-27 AT AT92114654T patent/ATE181552T1/de not_active IP Right Cessation
- 1992-08-27 DK DK92114654T patent/DK0529636T3/da active
-
1994
- 1994-02-25 NO NO940676A patent/NO301117B1/no unknown
- 1994-02-25 FI FI940889A patent/FI107156B/fi active
-
1995
- 1995-06-21 HU HU95P/P00323P patent/HU211632A9/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU211632A9 (en) | 1995-12-28 |
| FI940889A7 (fi) | 1994-02-25 |
| SK23894A3 (en) | 1994-12-07 |
| HUT70753A (en) | 1995-10-30 |
| CA2076948A1 (en) | 1993-03-01 |
| DE69229461D1 (de) | 1999-07-29 |
| WO1993005043A1 (en) | 1993-03-18 |
| NO940676L (cg-RX-API-DMAC10.html) | 1994-04-27 |
| CZ39594A3 (en) | 1994-11-16 |
| CA2076948C (en) | 2002-04-16 |
| NO940676D0 (no) | 1994-02-25 |
| DK0529636T3 (da) | 1999-12-13 |
| PL170920B1 (pl) | 1997-02-28 |
| EP0529636A1 (en) | 1993-03-03 |
| FI107156B (fi) | 2001-06-15 |
| FI940889A0 (fi) | 1994-02-25 |
| ATE181552T1 (de) | 1999-07-15 |
| MX9204914A (es) | 1993-07-01 |
| RU2114827C1 (ru) | 1998-07-10 |
| HU9400595D0 (en) | 1994-05-30 |
| JP3170584B2 (ja) | 2001-05-28 |
| GEP20002329B (en) | 2000-12-25 |
| AU2482092A (en) | 1993-04-05 |
| NO301117B1 (no) | 1997-09-15 |
| KR100277481B1 (ko) | 2001-02-01 |
| JPH06510056A (ja) | 1994-11-10 |
| AU655672B2 (en) | 1995-01-05 |
| EP0529636B1 (en) | 1999-06-23 |
| CZ282759B6 (cs) | 1997-09-17 |
| DE69229461T2 (de) | 1999-10-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2114827C1 (ru) | Производные изатина или изатиноксима, способ получения производных изатиноксима и фармацевтическая композиция | |
| AU599340B2 (en) | Condensed imidazopyridine derivatives | |
| KR100192641B1 (ko) | 하이드라존 유도체, 이의 제조방법 및 이를 포함하는 약제학적 조성물 | |
| EA002123B1 (ru) | Соединения, усиливающие активность ретиноидов | |
| Walser et al. | Pentacyclic triazolodiazepines as PAF‐antagonists | |
| Hussenether et al. | Clozapine derived 2, 3-dihydro-1H-1, 4-and 1, 5-benzodiazepines with D4 receptor selectivity: synthesis and biological testing | |
| JP3010558B2 (ja) | 新規の１，７‐融合１ｈ‐インドール‐２‐カルボン酸‐ｎ‐（１，４‐ベンゾジアゼピン‐３‐イル）‐アミド、その製法及びこれを含有するコレシストキニン拮抗作用薬剤 | |
| NO172437B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrimidindionforbindelser | |
| Huff et al. | Bioactive conformation of 1-arylpiperazines at central serotonin receptors | |
| JP2001114781A (ja) | 新規な多環式アザインドール化合物、それらの調製方法およびそれらを含有する薬学的組成物 | |
| DE60218646T2 (de) | N-biphenylcarbonyl- und n-phenylpyridylcarbonyl substituierte bi- und tricyclische azepine und diazepine als vasopressin-agonisten | |
| EP1381608B1 (en) | Cyclohexylphenyl vasopressin agonists | |
| EP0233049A1 (en) | 2,3,4,8,9,9a-Hexahydro-4-aryl-1H-indeno[1,7-cd]azepines | |
| CS226743B2 (en) | Method of preparing new 1,4,9,10-tetrahydropyrazolo (4,3-e)pyrido (3,2-b) l,4)diazepin-10-ones | |
| AU780027B2 (en) | New indenoindolone compounds, a process for their preparation and pharmaceutical compositions containing them | |
| US5436250A (en) | Isatineoxime derivatives, their preparation and use | |
| US5242918A (en) | Isatinoxime derivatives, their preparation and use | |
| KR20000029564A (ko) | 5ＨＴ2ｃ길항제및Ｄ2길항제를함유하는약제학적조성물 | |
| EP0272865A1 (en) | 1,4-Benzodiazepines with 5-and 6-membered heterocyclic rings | |
| UA79801C2 (en) | Novel derivatives of cycloalcanodiones, method for the production thereof and their pharmacological applications | |
| WO2000027851A1 (en) | Novel type condensed pyridazinone compounds | |
| CN114671829A (zh) | 以茚酮和二苯并氮杂卓为母核的杂二联体及其盐酸盐、其制备方法和用途 | |
| KR19980020007A (ko) | 1,4-벤조디아제핀-2,5-디온 유도체 및 약학적으로 허용되는 그의 염 |