DE2338058C3 - 7-Chlor-1,3-dihydro-1-(2-hydroxyäthyl)-3-hydroxy-5-(o-fluorphenyl)-2H-1,4-benzodiazepin-2-on, dieses enthaltendes Arzneimittel und Verfahren zu seiner Herstellung - Google Patents
7-Chlor-1,3-dihydro-1-(2-hydroxyäthyl)-3-hydroxy-5-(o-fluorphenyl)-2H-1,4-benzodiazepin-2-on, dieses enthaltendes Arzneimittel und Verfahren zu seiner HerstellungInfo
- Publication number
- DE2338058C3 DE2338058C3 DE2338058A DE2338058A DE2338058C3 DE 2338058 C3 DE2338058 C3 DE 2338058C3 DE 2338058 A DE2338058 A DE 2338058A DE 2338058 A DE2338058 A DE 2338058A DE 2338058 C3 DE2338058 C3 DE 2338058C3
- Authority
- DE
- Germany
- Prior art keywords
- chloro
- dihydro
- fluorophenyl
- benzodiazepin
- compound
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- VOJLELRQLPENHL-UHFFFAOYSA-N Doxefazepam Chemical compound N=1C(O)C(=O)N(CCO)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F VOJLELRQLPENHL-UHFFFAOYSA-N 0.000 title 1
- 239000003814 drug Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 229940049706 benzodiazepine Drugs 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 2
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- -1 2-acetoxyethyl Chemical group 0.000 description 1
- 206010019133 Hangover Diseases 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- WXAXNYYAYJKARR-UHFFFAOYSA-N benzene;2-(1,4-dioxan-2-yl)acetic acid Chemical compound C1=CC=CC=C1.OC(=O)CC1COCCO1 WXAXNYYAYJKARR-UHFFFAOYSA-N 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- SAADBVWGJQAEFS-UHFFFAOYSA-N flurazepam Chemical compound N=1CC(=O)N(CCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F SAADBVWGJQAEFS-UHFFFAOYSA-N 0.000 description 1
- 229960003528 flurazepam Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
- C07D243/26—Preparation from compounds already containing the benzodiazepine skeleton
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES405260A ES405260A1 (es) | 1972-07-28 | 1972-07-28 | Procedimiento para la preparacion de 3-hidroxi-5-aril-7- sustituidos-1, 3-dihidro-2h-1, 4-benzodiacepin-2-onas. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2338058A1 DE2338058A1 (de) | 1974-02-14 |
| DE2338058B2 DE2338058B2 (de) | 1980-11-06 |
| DE2338058C3 true DE2338058C3 (de) | 1982-01-14 |
Family
ID=8461826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2338058A Expired DE2338058C3 (de) | 1972-07-28 | 1973-07-26 | 7-Chlor-1,3-dihydro-1-(2-hydroxyäthyl)-3-hydroxy-5-(o-fluorphenyl)-2H-1,4-benzodiazepin-2-on, dieses enthaltendes Arzneimittel und Verfahren zu seiner Herstellung |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5738586B2 (enExample) |
| BE (1) | BE865164Q (enExample) |
| DE (1) | DE2338058C3 (enExample) |
| ES (1) | ES405260A1 (enExample) |
| FR (1) | FR2194432B1 (enExample) |
| GB (1) | GB1431282A (enExample) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE621819A (enExample) * | 1961-08-29 | |||
| NL289735A (enExample) * | 1962-03-09 | |||
| NL301733A (enExample) * | 1962-12-20 | |||
| NL298071A (enExample) * | 1963-06-04 | |||
| DE2043614A1 (en) * | 1969-09-19 | 1971-03-25 | Gerot Pharmazeutika Dr Walter Otto KG, Wien | Hydroxy benzodiazepine derivs with sedative - activity |
| JPS5011999B1 (enExample) * | 1971-06-18 | 1975-05-08 |
-
1972
- 1972-07-28 ES ES405260A patent/ES405260A1/es not_active Expired
-
1973
- 1973-07-19 JP JP8253473A patent/JPS5738586B2/ja not_active Expired
- 1973-07-25 GB GB3541273A patent/GB1431282A/en not_active Expired
- 1973-07-26 DE DE2338058A patent/DE2338058C3/de not_active Expired
- 1973-07-27 FR FR7327672A patent/FR2194432B1/fr not_active Expired
-
1978
- 1978-03-22 BE BE2056783A patent/BE865164Q/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2194432B1 (enExample) | 1976-12-03 |
| BE865164Q (fr) | 1978-07-17 |
| DE2338058A1 (de) | 1974-02-14 |
| FR2194432A1 (enExample) | 1974-03-01 |
| JPS4980086A (enExample) | 1974-08-02 |
| GB1431282A (en) | 1976-04-07 |
| ES405260A1 (es) | 1975-07-01 |
| JPS5738586B2 (enExample) | 1982-08-16 |
| DE2338058B2 (de) | 1980-11-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3231255C2 (enExample) | ||
| DE2617738C2 (enExample) | ||
| DE3044740A1 (de) | Nucleosidderivate, ihre herstellung und pharmazeutische mittel | |
| DE2237592C2 (de) | 6-(o-Chlorphenyl)-8-chlor-4H-imidazo-[1,2-a] [1,4]-benzodiazepine und Verfahren zu ihrer Herstellung | |
| DE1720020B2 (de) | 1- eckige Klammer auf alpha-(N-o-Chlorbenzyl)-pyrryl eckige Klammer zu -2-di-sec-burylamino-äthanol, dessen Säureadditionssalze und Verfahren zu seiner Herstellung | |
| DE3202281A1 (de) | Pyrrolidin-derivat | |
| DE2338058C3 (de) | 7-Chlor-1,3-dihydro-1-(2-hydroxyäthyl)-3-hydroxy-5-(o-fluorphenyl)-2H-1,4-benzodiazepin-2-on, dieses enthaltendes Arzneimittel und Verfahren zu seiner Herstellung | |
| DE1811518B2 (de) | Daunorubicinderivale, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| DE2609154C2 (de) | L-Pyroglutamyl-L-histidyl-prolinamide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE1931081A1 (de) | Verfahren zur Herstellung neuer heterocyclischer Verbindungen | |
| DE2904826A1 (de) | Neue derivate des 3-phenyltetrahydropyridins und deren salze, verfahren zu deren herstellung, deren verwendung als arzneimittel und die sie enthaltenden pharmazeutischen zusammensetzungen | |
| DE2719608A1 (de) | Benzodiazepinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| DE1916481A1 (de) | Hydroxylaminderivate,ihre Verwendung und Verfahren zur Herstellung derselben | |
| DE1695298B2 (de) | S-AcetamMo-e-methyl-e-n-propyl-striazolo eckige Klammer auf 4,3-a eckige Klammer zu pyrazin und Verfahren zu seiner Herstellung und Arzneimittel | |
| DE2456311A1 (de) | Benzodiazepinderivate | |
| DE1944404C3 (de) | Verfahren zur Herstellung von 5-Phenyl-l,3-dihydro-2H-l,4-benzodiazepin-2-on-derivaten | |
| DE2305727C2 (de) | Pentapeptide und deren Derivate sowie diese Verbindungen enthaltende Arzneimittel | |
| DE2917890C2 (enExample) | ||
| DE2513136B2 (de) | N-(I -Benzylpiperid-4-yl)-benzamide, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate | |
| DE1620177C3 (de) | N-(2-Hydroxyäthyl)-piperazinocarboxymethyl-tetracyclin, dessen pharmakologisch verwendbaren Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2138773C2 (de) | 1-(2,2,2-Trifluoroäthyl)-7-chloro-1,3-dihydro-5-phenyl-2 H-1,4-benzodiazepin-2-thione, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zubereitungen | |
| EP0069894B1 (de) | Optisch aktives Dipeptide, seine pharmazeutisch verträglichen Salze, Verfahren zur Herstellung und diese enthaltende pharmazeutische Präparate | |
| DE2537069C2 (enExample) | ||
| EP0424670B1 (de) | Neue ZNS-aktive Hexapeptide mit antiamnestischer Wirkung | |
| DE2265139C3 (de) | Substituierte l-Methyl-5-phenyl-13-Dihydro-2H-1,4-benzodiazepin-2-on-derivate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |