SK284103B6 - 3-Substituované deriváty 3H-2,3-benzodiazepínu, spôsob ich výroby, ich použitie v liečivách a farmaceutický prostriedok tieto látky obsahujúci - Google Patents
3-Substituované deriváty 3H-2,3-benzodiazepínu, spôsob ich výroby, ich použitie v liečivách a farmaceutický prostriedok tieto látky obsahujúci Download PDFInfo
- Publication number
- SK284103B6 SK284103B6 SK135-97A SK13597A SK284103B6 SK 284103 B6 SK284103 B6 SK 284103B6 SK 13597 A SK13597 A SK 13597A SK 284103 B6 SK284103 B6 SK 284103B6
- Authority
- SK
- Slovakia
- Prior art keywords
- carbon atoms
- group
- optionally substituted
- alkanoyl
- alkyl
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- RQKDTQACQPHOQL-UHFFFAOYSA-N 3h-2,3-benzodiazepine Chemical class C1=NNC=CC2=CC=CC=C21 RQKDTQACQPHOQL-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 239000003814 drug Substances 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- -1 7-methylcarbamoyl-5- (4-aminophenyl) 6-methyl-7H-1,3-dioxolo [4,5-h] [2,3] benzodiazepine Chemical compound 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- SSZCVESQZCYBBF-UHFFFAOYSA-N 1-[5-(4-aminophenyl)-8-methyl-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-7-yl]ethanone Chemical compound C12=CC=3OCOC=3C=C2C=C(C)N(C(=O)C)N=C1C1=CC=C(N)C=C1 SSZCVESQZCYBBF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 230000002461 excitatory amino acid Effects 0.000 claims description 3
- 239000003257 excitatory amino acid Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 208000013403 hyperactivity Diseases 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 10
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 206010010904 Convulsion Diseases 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
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- 102000003678 AMPA Receptors Human genes 0.000 description 5
- 108090000078 AMPA Receptors Proteins 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 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 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 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 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- RNQRLYWVOJJHKD-UHFFFAOYSA-N 8-methyl-5-(4-nitrophenyl)-9h-[1,3]dioxolo[4,5-h][2,3]benzodiazepine Chemical compound C12=CC=3OCOC=3C=C2CC(C)=NN=C1C1=CC=C([N+]([O-])=O)C=C1 RNQRLYWVOJJHKD-UHFFFAOYSA-N 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
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- 206010053398 Clonic convulsion Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 208000012902 Nervous system disease Diseases 0.000 description 2
- 208000025966 Neurological disease Diseases 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- 229940049706 benzodiazepine Drugs 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
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- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
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- ZVHGCRPPOMGSHZ-UHFFFAOYSA-N 1-[8-methyl-5-(4-nitrophenyl)-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-7-yl]ethanone Chemical compound C12=CC=3OCOC=3C=C2C=C(C)N(C(=O)C)N=C1C1=CC=C([N+]([O-])=O)C=C1 ZVHGCRPPOMGSHZ-UHFFFAOYSA-N 0.000 description 1
- GJYWKWKWZCUNTJ-UHFFFAOYSA-N 15-methyl-12-(4-nitrophenyl)-4,7-dioxa-13,14-diazatricyclo[9.5.0.03,9]hexadeca-1,3(9),10,12,14-pentaene Chemical compound C12=CC=3COCCOC=3C=C2CC(C)=NN=C1C1=CC=C([N+]([O-])=O)C=C1 GJYWKWKWZCUNTJ-UHFFFAOYSA-N 0.000 description 1
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- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
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-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Toxicology (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4428835A DE4428835A1 (de) | 1994-08-01 | 1994-08-01 | Neue 3-substituierte 3H-2,3-Benzodiazepinderivate, deren Herstellung und Verwendung als Arzneimittel |
| PCT/DE1995/001029 WO1996004283A1 (de) | 1994-08-01 | 1995-07-28 | Neue 3-substituierte 3h-2,3-benzodiazepinderivate, deren herstellung und verwendung als arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK13597A3 SK13597A3 (en) | 1997-07-09 |
| SK284103B6 true SK284103B6 (sk) | 2004-09-08 |
Family
ID=6525693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK135-97A SK284103B6 (sk) | 1994-08-01 | 1995-07-28 | 3-Substituované deriváty 3H-2,3-benzodiazepínu, spôsob ich výroby, ich použitie v liečivách a farmaceutický prostriedok tieto látky obsahujúci |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5756495A (cs) |
| EP (1) | EP0775143B1 (cs) |
| JP (1) | JPH10504543A (cs) |
| KR (1) | KR100386709B1 (cs) |
| CN (1) | CN1048728C (cs) |
| AT (1) | ATE223415T1 (cs) |
| AU (1) | AU693241B2 (cs) |
| CA (1) | CA2195747C (cs) |
| CZ (1) | CZ291276B6 (cs) |
| DE (2) | DE4428835A1 (cs) |
| DK (1) | DK0775143T3 (cs) |
| ES (1) | ES2181787T3 (cs) |
| FI (1) | FI113177B (cs) |
| HU (1) | HU225500B1 (cs) |
| MX (1) | MX9700813A (cs) |
| NO (1) | NO319151B1 (cs) |
| NZ (1) | NZ290777A (cs) |
| PT (1) | PT775143E (cs) |
| RU (1) | RU2146678C1 (cs) |
| SK (1) | SK284103B6 (cs) |
| WO (1) | WO1996004283A1 (cs) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP9701325A1 (hu) | 1997-07-31 | 2000-08-28 | Gyógyszerkutató Intézet Kft. | Új 2,3-benzodiazepin-származékok |
| UA67749C2 (uk) | 1997-08-12 | 2004-07-15 | Егіш Дьйодьсердьяр Рт. | Похідна 8-заміщеного-9н-1,3-діоксол/4,5-h//2,3/бензодіазепіну з властивостями амра/каїнатного антагоніста, спосіб одержання похідних, фармацевтична композиція (варіанти), спосіб її одержання та спосіб лікування |
| PL338681A1 (en) * | 1997-08-12 | 2000-11-20 | Egyt Gyogyszervegyeszeti Gyar | Derivatives of 1,3-dioxolo/4,5-h/2,3-benzodiazepins as inhibitors of ampa/cainate receptors |
| HU227128B1 (en) * | 1999-07-07 | 2010-07-28 | Egyt Gyogyszervegyeszeti Gyar | New 2,3-benzodiazepine derivatives |
| NO320473B1 (no) * | 2002-09-09 | 2005-12-12 | Norsk Hydro As | Anordning ved separator for separasjon av flerfasefluid. |
| US6858605B2 (en) | 2003-02-04 | 2005-02-22 | Ivax Drug Research Institute, Ltd. | Substituted 2,3-benzodiazepine derivatives |
| GB0405034D0 (en) * | 2004-03-05 | 2004-04-07 | Novartis Ag | Organic compounds |
| WO2006107860A2 (en) * | 2005-04-04 | 2006-10-12 | Eisai Co., Ltd. | Dihydropyridine compounds and compositions for headaches |
| NZ566137A (en) * | 2005-09-09 | 2011-05-27 | Novartis Ag | The use of diphenyl thioether derivatives to treat autoimmune diseases |
| WO2015121268A1 (de) * | 2014-02-14 | 2015-08-20 | Bayer Pharma Aktiengesellschaft | 1-phenyl-3h-2,3-benzodiazepine und ihre verwendung als bromodomänen-inhibitoren |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU219778B (hu) * | 1990-12-21 | 2001-07-30 | Gyógyszerkutató Intézet Közös Vállalat | Eljárás N-acil-2,3-benzodiazepin-származékok, savaddíciós sóik és az ezeket tartalmazó gyógyászati készítmények előállítására, valamint a vegyületek egy csoportja, és az ezeket tartalmazó gyógyászati készítmények |
| SI9111433B (sl) * | 1991-08-22 | 1999-02-28 | Pliva | Novi N-sulfonil-tetrahidro-/1,3/-dioksepino/5,6-b/azirini, postopek priprave, intermediati za njihovo pripravo in uporaba |
-
1994
- 1994-08-01 DE DE4428835A patent/DE4428835A1/de not_active Withdrawn
-
1995
- 1995-07-28 JP JP8506095A patent/JPH10504543A/ja not_active Ceased
- 1995-07-28 HU HU9700320A patent/HU225500B1/hu unknown
- 1995-07-28 AT AT95927636T patent/ATE223415T1/de not_active IP Right Cessation
- 1995-07-28 CA CA002195747A patent/CA2195747C/en not_active Expired - Fee Related
- 1995-07-28 NZ NZ290777A patent/NZ290777A/en unknown
- 1995-07-28 DE DE59510364T patent/DE59510364D1/de not_active Expired - Fee Related
- 1995-07-28 CZ CZ1997159A patent/CZ291276B6/cs not_active IP Right Cessation
- 1995-07-28 ES ES95927636T patent/ES2181787T3/es not_active Expired - Lifetime
- 1995-07-28 AU AU31609/95A patent/AU693241B2/en not_active Ceased
- 1995-07-28 DK DK95927636T patent/DK0775143T3/da active
- 1995-07-28 US US08/776,536 patent/US5756495A/en not_active Expired - Fee Related
- 1995-07-28 RU RU97103140A patent/RU2146678C1/ru not_active IP Right Cessation
- 1995-07-28 PT PT95927636T patent/PT775143E/pt unknown
- 1995-07-28 SK SK135-97A patent/SK284103B6/sk unknown
- 1995-07-28 KR KR1019970700650A patent/KR100386709B1/ko not_active Expired - Fee Related
- 1995-07-28 WO PCT/DE1995/001029 patent/WO1996004283A1/de active IP Right Grant
- 1995-07-28 MX MX9700813A patent/MX9700813A/es unknown
- 1995-07-28 EP EP95927636A patent/EP0775143B1/de not_active Expired - Lifetime
- 1995-07-28 CN CN95194402A patent/CN1048728C/zh not_active Expired - Fee Related
-
1997
- 1997-01-31 NO NO19970435A patent/NO319151B1/no unknown
- 1997-01-31 FI FI970434A patent/FI113177B/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| JPH10504543A (ja) | 1998-05-06 |
| CN1155285A (zh) | 1997-07-23 |
| AU693241B2 (en) | 1998-06-25 |
| PT775143E (pt) | 2003-01-31 |
| KR100386709B1 (ko) | 2003-08-19 |
| CA2195747C (en) | 2006-01-24 |
| EP0775143B1 (de) | 2002-09-04 |
| ES2181787T3 (es) | 2003-03-01 |
| DK0775143T3 (da) | 2002-12-02 |
| FI113177B (fi) | 2004-03-15 |
| ATE223415T1 (de) | 2002-09-15 |
| NZ290777A (en) | 1998-07-28 |
| EP0775143A1 (de) | 1997-05-28 |
| SK13597A3 (en) | 1997-07-09 |
| NO319151B1 (no) | 2005-06-27 |
| AU3160995A (en) | 1996-03-04 |
| RU2146678C1 (ru) | 2000-03-20 |
| DE59510364D1 (de) | 2002-10-10 |
| HU225500B1 (en) | 2007-01-29 |
| DE4428835A1 (de) | 1996-02-08 |
| HUT76801A (en) | 1997-11-28 |
| CZ291276B6 (cs) | 2003-01-15 |
| MX9700813A (es) | 1997-05-31 |
| US5756495A (en) | 1998-05-26 |
| NO970435L (no) | 1997-01-31 |
| FI970434A0 (fi) | 1997-01-31 |
| WO1996004283A1 (de) | 1996-02-15 |
| CZ15997A3 (en) | 1997-06-11 |
| FI970434L (fi) | 1997-01-31 |
| NO970435D0 (no) | 1997-01-31 |
| CA2195747A1 (en) | 1996-02-15 |
| CN1048728C (zh) | 2000-01-26 |
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