FR2474501A1 - 11-(2'-imidazol-1''-yl)-acetyl-5,11-dihydro-6h-pyrido (2,3-b) (1,4) benzodiazepin-6-ones, leur procede de preparation et leur application dans la therapie de l'ulcere - Google Patents
11-(2'-imidazol-1''-yl)-acetyl-5,11-dihydro-6h-pyrido (2,3-b) (1,4) benzodiazepin-6-ones, leur procede de preparation et leur application dans la therapie de l'ulcere Download PDFInfo
- Publication number
- FR2474501A1 FR2474501A1 FR8101328A FR8101328A FR2474501A1 FR 2474501 A1 FR2474501 A1 FR 2474501A1 FR 8101328 A FR8101328 A FR 8101328A FR 8101328 A FR8101328 A FR 8101328A FR 2474501 A1 FR2474501 A1 FR 2474501A1
- Authority
- FR
- France
- Prior art keywords
- pyrido
- dihydro
- general formula
- acetyl
- benzodiazepin
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000002560 therapeutic procedure Methods 0.000 title abstract description 3
- 208000025865 Ulcer Diseases 0.000 claims abstract description 4
- -1 NITRO GROUP Chemical group 0.000 claims abstract description 3
- 231100000397 ulcer Toxicity 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 230000029936 alkylation Effects 0.000 claims 2
- 238000005804 alkylation reaction Methods 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YZPAKBGVJIVPEU-UHFFFAOYSA-N 1,2-benzodiazepin-6-one Chemical class N1=NC=CC=C2C(=O)C=CC=C21 YZPAKBGVJIVPEU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- QYETZOYLEWPRIX-UHFFFAOYSA-N pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1N=C2C=CC=NC2=NC2=CC=CC=C12 QYETZOYLEWPRIX-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- KSSXNHGPIDAUAS-UHFFFAOYSA-N 1,4-benzodiazepin-6-one Chemical compound N1=CC=NC=C2C(=O)C=CC=C21 KSSXNHGPIDAUAS-UHFFFAOYSA-N 0.000 description 1
- AKMNUCBQGHFICM-UHFFFAOYSA-N 1-(2-methyl-1,3-benzoxazol-6-yl)-3-(1,5-naphthyridin-4-yl)urea Chemical compound C1=CN=C2C(NC(=O)NC3=CC=C4N=C(OC4=C3)C)=CC=NC2=C1 AKMNUCBQGHFICM-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
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002496 gastric effect Effects 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 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 |
|---|---|
| FR2474501A1 true FR2474501A1 (fr) | 1981-07-31 |
Family
ID=11157749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8101328A Pending FR2474501A1 (fr) | 1980-01-24 | 1981-01-23 | 11-(2'-imidazol-1''-yl)-acetyl-5,11-dihydro-6h-pyrido (2,3-b) (1,4) benzodiazepin-6-ones, leur procede de preparation et leur application dans la therapie de l'ulcere |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS56113783A (en, 2012) |
| BE (1) | BE887069A (en, 2012) |
| DE (1) | DE3102152A1 (en, 2012) |
| DK (1) | DK32481A (en, 2012) |
| ES (1) | ES498768A0 (en, 2012) |
| FR (1) | FR2474501A1 (en, 2012) |
| GB (1) | GB2068944A (en, 2012) |
| GR (1) | GR72993B (en, 2012) |
| IT (1) | IT1193371B (en, 2012) |
| PT (1) | PT72392B (en, 2012) |
| SE (1) | SE8100333L (en, 2012) |
| YU (1) | YU16981A (en, 2012) |
| ZA (1) | ZA81510B (en, 2012) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2392991A1 (fr) * | 1977-05-31 | 1978-12-29 | Thomae Gmbh Dr K | Nouvelles 5,11-dihydro-6h-pyrido(2,3-b) (1,4) benzodiazepin-6-ones substituees en position 11, procedes pour leur preparation et medicaments renfermant ces composes |
-
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 DE DE19813102152 patent/DE3102152A1/de not_active Withdrawn
- 1981-01-23 ZA ZA00810510A patent/ZA81510B/xx unknown
- 1981-01-23 DK DK32481A patent/DK32481A/da unknown
- 1981-01-23 PT PT72392A patent/PT72392B/pt unknown
- 1981-01-23 JP JP889481A patent/JPS56113783A/ja active Pending
- 1981-01-23 FR FR8101328A patent/FR2474501A1/fr active Pending
- 1981-01-23 ES ES498768A patent/ES498768A0/es active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2392991A1 (fr) * | 1977-05-31 | 1978-12-29 | Thomae Gmbh Dr K | Nouvelles 5,11-dihydro-6h-pyrido(2,3-b) (1,4) benzodiazepin-6-ones substituees en position 11, procedes pour leur preparation et medicaments renfermant ces composes |
Non-Patent Citations (1)
| Title |
|---|
| DIE PHARMAZIE, vol. 27, no. 3, mars 1972, Berlin (DE) * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56113783A (en) | 1981-09-07 |
| ES8201157A1 (es) | 1981-12-01 |
| ZA81510B (en) | 1982-05-26 |
| IT8019423A0 (it) | 1980-01-24 |
| PT72392B (en) | 1981-12-21 |
| GR72993B (en, 2012) | 1984-01-25 |
| IT1193371B (it) | 1988-06-15 |
| BE887069A (fr) | 1981-05-04 |
| SE8100333L (sv) | 1981-07-25 |
| ES498768A0 (es) | 1981-12-01 |
| YU16981A (en) | 1983-10-31 |
| DK32481A (da) | 1981-07-25 |
| DE3102152A1 (de) | 1981-12-10 |
| GB2068944A (en) | 1981-08-19 |
| PT72392A (en) | 1981-02-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0115248B1 (de) | Substituierte 5H-Pyrimido(5,4-b)indole | |
| JPS63132889A (ja) | キナゾリノン誘導体 | |
| US4251520A (en) | Glucofuranose derivatives | |
| EP0267111A1 (fr) | Imidazopyridines, leur préparation et leur application en thérapeutique | |
| EP0013315A2 (en) | Eburnane derivatives, their synthesis and pharmaceutical compositions containing them | |
| EP0061380A1 (fr) | Dérivés d'imidazo (1,2-a) pyrimidines, leur préparation et leur application en thérapeutique | |
| US5676831A (en) | Isoindolinone derivative, preparation thereof and pharmaceutical compositions containing same | |
| FR2474501A1 (fr) | 11-(2'-imidazol-1''-yl)-acetyl-5,11-dihydro-6h-pyrido (2,3-b) (1,4) benzodiazepin-6-ones, leur procede de preparation et leur application dans la therapie de l'ulcere | |
| JP3221874B2 (ja) | クラウセンアミドおよびネオクラウセンアミド並びにそれらの誘導体の製法 | |
| US4950677A (en) | Benzimidazole derivative compounds and method of making | |
| WO1983000330A1 (en) | New process for the preparation of diphenyl-3,4 methyl-5 pyrazole derivatives | |
| EP0449172B1 (en) | A method of reducing a carbonyl containing acridine | |
| CA1199638A (en) | Eburnane-oxime ethers, process for their preparation and pharmaceutical compositions containing them | |
| EP0239667B1 (de) | 5- oder 6-substituierte-beta-carbolin-3-carbonsäureester | |
| AT338798B (de) | Verfahren zur herstellung von neuen 6-aza-3h-1,4-benzodiazepinen, deren optischen isomeren und deren salzen | |
| US5169859A (en) | Thiazolidinone derivatives, pharmaceutical compositions containing them and process for preparing same | |
| FR2531709A1 (fr) | Diazabicyclooctanes, procede pour leur preparation et compositions pharmaceutiques les renfermant | |
| EP0015786B1 (fr) | Imidazo et pyrimido-pyrido-indoles, leur préparation et médicaments les contenant | |
| BE884977A (fr) | Nouveau n-phenyl-benzamides utiles dans le traitement de l'inflammation et de la douleur des mammiferes | |
| BE665737A (en, 2012) | ||
| FR2523580A1 (fr) | Pyrimidine-dicarbamates et leur utilisation dans la preparation d'oxadiazolopyrimidines connues en tant que medicaments hypotenseurs | |
| BE824491R (fr) | Procede de preparation de derives de 1,8-naphthyridine | |
| IE42462B1 (en) | 1-methyl-2-nitro-imidazole-5-methanol derivatives | |
| FR2600648A1 (fr) | N-imidazolylmethyl-diphenylazomethines, leur preparation et leur application en therapeutique | |
| EP0393109A1 (en) | Novel 2,3-thiomorpholinedione-2-oxime derivatives, pharmaceutical compositions containing them and process for preparing same. |