DE3102152A1 - 5,11-dihydro-6h-pyrido-(2,3-b) (1,4)-benzodiazepin-6-on-derivate, verfahren zu deren herstellung und dieselben enthaltendes mittel - Google Patents
5,11-dihydro-6h-pyrido-(2,3-b) (1,4)-benzodiazepin-6-on-derivate, verfahren zu deren herstellung und dieselben enthaltendes mittelInfo
- Publication number
- DE3102152A1 DE3102152A1 DE19813102152 DE3102152A DE3102152A1 DE 3102152 A1 DE3102152 A1 DE 3102152A1 DE 19813102152 DE19813102152 DE 19813102152 DE 3102152 A DE3102152 A DE 3102152A DE 3102152 A1 DE3102152 A1 DE 3102152A1
- Authority
- DE
- Germany
- Prior art keywords
- pyrido
- dihydro
- benzodiazepin
- acetyl
- general formula
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims 2
- MIRBIZDDMSFTKY-UHFFFAOYSA-N 5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical class O=C1NC2=CC=CN=C2NC2=CC=CC=C12 MIRBIZDDMSFTKY-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 229940049706 benzodiazepine Drugs 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000012790 confirmation Methods 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 208000025865 Ulcer Diseases 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 231100000397 ulcer Toxicity 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 230000000767 anti-ulcer Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- CJYVBBVAFYUWDF-UHFFFAOYSA-N 1,2-benzodiazepin-6-one;hydrochloride Chemical compound Cl.N1=NC=CC=C2C(=O)C=CC=C21 CJYVBBVAFYUWDF-UHFFFAOYSA-N 0.000 description 1
- FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- HOBWAPHTEJGALG-JKCMADFCSA-N [(1r,5s)-8-methyl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;sulfate Chemical compound [O-]S([O-])(=O)=O.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1 HOBWAPHTEJGALG-JKCMADFCSA-N 0.000 description 1
- JDQJWBCSXZWVGM-UHFFFAOYSA-N acetonitrile;2-propan-2-yloxypropane Chemical compound CC#N.CC(C)OC(C)C JDQJWBCSXZWVGM-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229960002028 atropine sulfate Drugs 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19423/80A IT1193371B (it) | 1980-01-24 | 1980-01-24 | 11-(2'-imidazol-1''-il)-acetil-5,11-diidro-6h-pirido 2,3-b 1,4 benzodiazepin-6-oni,metodo per la loro preparazione e la loro applicazione nella terapia dell'ulcera |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3102152A1 true DE3102152A1 (de) | 1981-12-10 |
Family
ID=11157749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813102152 Withdrawn DE3102152A1 (de) | 1980-01-24 | 1981-01-23 | 5,11-dihydro-6h-pyrido-(2,3-b) (1,4)-benzodiazepin-6-on-derivate, verfahren zu deren herstellung und dieselben enthaltendes mittel |
Country Status (13)
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4210648A (en) * | 1977-05-31 | 1980-07-01 | Boehringer Ingelheim Gmbh | II-Aminoacyl-5,11-dihydro-6H-pyrido(2,3-B) (1,4)benzodiazepin-6-ones and salts thereof |
-
1979
- 1979-01-22 GR GR63939A patent/GR72993B/el unknown
-
1980
- 1980-01-24 IT IT19423/80A patent/IT1193371B/it active
-
1981
- 1981-01-14 BE BE0/203478A patent/BE887069A/fr unknown
- 1981-01-19 GB GB8101518A patent/GB2068944A/en not_active Withdrawn
- 1981-01-21 SE SE8100333A patent/SE8100333L/xx not_active Application Discontinuation
- 1981-01-22 YU YU00169/81A patent/YU16981A/xx unknown
- 1981-01-23 JP JP889481A patent/JPS56113783A/ja active Pending
- 1981-01-23 ES ES498768A patent/ES498768A0/es active Granted
- 1981-01-23 PT PT72392A patent/PT72392B/pt unknown
- 1981-01-23 ZA ZA00810510A patent/ZA81510B/xx unknown
- 1981-01-23 FR FR8101328A patent/FR2474501A1/fr active Pending
- 1981-01-23 DE DE19813102152 patent/DE3102152A1/de not_active Withdrawn
- 1981-01-23 DK DK32481A patent/DK32481A/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE887069A (fr) | 1981-05-04 |
| PT72392B (en) | 1981-12-21 |
| FR2474501A1 (fr) | 1981-07-31 |
| ZA81510B (en) | 1982-05-26 |
| PT72392A (en) | 1981-02-01 |
| GB2068944A (en) | 1981-08-19 |
| YU16981A (en) | 1983-10-31 |
| IT1193371B (it) | 1988-06-15 |
| JPS56113783A (en) | 1981-09-07 |
| SE8100333L (sv) | 1981-07-25 |
| DK32481A (da) | 1981-07-25 |
| IT8019423A0 (it) | 1980-01-24 |
| ES8201157A1 (es) | 1981-12-01 |
| ES498768A0 (es) | 1981-12-01 |
| GR72993B (enrdf_load_stackoverflow) | 1984-01-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2658544C2 (de) | Carbostyrilderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2824781C3 (de) | l-Alkyl^-hydroxymethyl-SAStrihydroxy-piperidinderivate | |
| DE69620306T2 (de) | 4-(.Alpha.-hydroxy-.alpha.-aryl-alkylcarbonylamino)-Piperidine zur Behandlung und Prophylaxe von Erkrankungen der Harnwege | |
| DE2426149C3 (de) | 7-Fluor-substituierte Phenothiazine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel | |
| DE1914571C3 (de) | L-SHydroxy-e-oxomorphinan-Verbindungen | |
| EP0018360B1 (de) | N-(5-Methoxybentofuran-2-ylcarbonyl)-N'-benzylpiperazin und Verfahren zu dessen Herstellung | |
| DE2724478C2 (de) | 5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-on-derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE60116902T2 (de) | Neue desloratadinsalze, verfahren zu deren synthese und diese enthaltende pharmazeutische zusammensetzungen | |
| DE2757858C2 (enrdf_load_stackoverflow) | ||
| DE68912252T2 (de) | Imidazolantiarrythmische Mittel. | |
| DE3102152A1 (de) | 5,11-dihydro-6h-pyrido-(2,3-b) (1,4)-benzodiazepin-6-on-derivate, verfahren zu deren herstellung und dieselben enthaltendes mittel | |
| DE2634336B2 (de) | Diaminoandrostan-Derivate, deren Säureadditionssalze und quaternären Salze sowie ein Verfahren zur Herstellung dieser Verbindungen | |
| DE3223877C2 (enrdf_load_stackoverflow) | ||
| CH616141A5 (enrdf_load_stackoverflow) | ||
| DE2942832C2 (de) | Carbamoylpiperazinderivate | |
| DE3874465T2 (de) | 1,2,3,4-tetrahydroisochonoline als antiarrhythmische mittel. | |
| DE3132475A1 (de) | Neue cytostatisch wirksame verbindungen und verfahren zu ihrer herstellung | |
| DE2849572C2 (de) | 4,5,6,7-Tetrahydroimidazo-[4,5-c]-pyridin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE3888697T2 (de) | 2,3-thiomorpholinedion-2-oxim-derivate, arzneimittelzusammensetzungen und verfahren zur herstellung. | |
| DE1100639B (de) | Verfahren zur Herstellung von basisch substituierten Barbitursaeure-derivaten | |
| DE3886125T2 (de) | Harnstoff-Derivate. | |
| DE2262912A1 (de) | Pyrido eckige klammer auf 3,4-d eckige klammer zu pyridazinderivate und verfahren zu ihrer herstellung | |
| AT364824B (de) | Verfahren zur herstellung neuer n-(1-(3-benzoylpropyl)-4-piperidyl)-sulfonsaeureamide und von deren saeureadditionssalzen | |
| AT376973B (de) | Verfahren zum herstellen neuer carbostyrilderivate und von saeureadditionssalzen und quaternaeren salzen hievon und ihren optischen isomeren | |
| AT330176B (de) | Verfahren zur herstellung von arylketonen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: BARTELS, H. HELD, M., DIPL.-ING. DR.-ING., PAT.-AN |
|
| 8139 | Disposal/non-payment of the annual fee |