SU452098A3 - Способ получени 1-арил-3н-1,4 -бензодиазепин-2,5-(1н,4н)-дионов - Google Patents
Способ получени 1-арил-3н-1,4 -бензодиазепин-2,5-(1н,4н)-дионовInfo
- Publication number
- SU452098A3 SU452098A3 SU1860137*7A SU1860137A SU452098A3 SU 452098 A3 SU452098 A3 SU 452098A3 SU 1860137 A SU1860137 A SU 1860137A SU 452098 A3 SU452098 A3 SU 452098A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- phenyl
- benzodiazepin
- dione
- nitro
- obtaining
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- -1 nitro, amino Chemical group 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NDJFJYDIKGUXRV-UHFFFAOYSA-N 2-anilino-4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1NC1=CC=CC=C1 NDJFJYDIKGUXRV-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2165311A DE2165311A1 (de) | 1971-12-29 | 1971-12-29 | Neue 1-aryl-3h-1,4-benzodiazepin2,5-(1h,4h)-dione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU452098A3 true SU452098A3 (ru) | 1974-11-30 |
Family
ID=5829591
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1860137*7A SU452098A3 (ru) | 1971-12-29 | 1972-12-20 | Способ получени 1-арил-3н-1,4 -бензодиазепин-2,5-(1н,4н)-дионов |
| SU1955543A SU461502A3 (ru) | 1971-12-29 | 1972-12-20 | Способ получени 1-арил-3н-1, 4-бензодиазепин-2,5-(1н,4н)дионов |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1955543A SU461502A3 (ru) | 1971-12-29 | 1972-12-20 | Способ получени 1-арил-3н-1, 4-бензодиазепин-2,5-(1н,4н)дионов |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS4885587A (enExample) |
| AT (2) | AT327912B (enExample) |
| BE (1) | BE793460A (enExample) |
| BG (2) | BG19805A3 (enExample) |
| CA (1) | CA1028702A (enExample) |
| CH (2) | CH583208A5 (enExample) |
| DD (1) | DD106384A5 (enExample) |
| DE (1) | DE2165311A1 (enExample) |
| DK (1) | DK129655B (enExample) |
| ES (2) | ES410057A1 (enExample) |
| FI (1) | FI54920C (enExample) |
| FR (1) | FR2166204B1 (enExample) |
| GB (1) | GB1395772A (enExample) |
| HU (1) | HU165306B (enExample) |
| IE (1) | IE37815B1 (enExample) |
| IL (1) | IL41198A (enExample) |
| NL (1) | NL7217795A (enExample) |
| NO (1) | NO138089C (enExample) |
| PL (2) | PL84244B1 (enExample) |
| RO (1) | RO62852A (enExample) |
| SE (1) | SE405120B (enExample) |
| SU (2) | SU452098A3 (enExample) |
| ZA (1) | ZA729073B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2687556C1 (ru) * | 2018-12-24 | 2019-05-15 | Акционерное общество "Федеральный научно-производственный центр "Алтай" | Способ получения 7-хлор-1,3-дигидро-1-метил-5-фенил-2Н-1,4-бензодиазепин-2-она |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1319144C (en) * | 1986-11-14 | 1993-06-15 | Quirico Branca | Tetrahydronaphthalene derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT280290B (de) * | 1967-11-24 | 1970-04-10 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von neuen 1-Phenyl-4-alkyl-3H-1,4-benzodiazepin-2,5-[1H,4H]-dionen |
-
0
- BE BE793460D patent/BE793460A/xx unknown
-
1971
- 1971-12-29 DE DE2165311A patent/DE2165311A1/de active Pending
-
1972
- 1972-12-19 AT AT1080772A patent/AT327912B/de not_active IP Right Cessation
- 1972-12-19 RO RO7200073207A patent/RO62852A/ro unknown
- 1972-12-19 AT AT228574*1A patent/AT324345B/de not_active IP Right Cessation
- 1972-12-20 SU SU1860137*7A patent/SU452098A3/ru active
- 1972-12-20 SU SU1955543A patent/SU461502A3/ru active
- 1972-12-21 DK DK641872AA patent/DK129655B/da unknown
- 1972-12-26 BG BG022240A patent/BG19805A3/xx unknown
- 1972-12-26 JP JP47129704A patent/JPS4885587A/ja active Pending
- 1972-12-26 BG BG025578A patent/BG20375A3/xx unknown
- 1972-12-27 ES ES410057A patent/ES410057A1/es not_active Expired
- 1972-12-27 CH CH250676A patent/CH583208A5/xx not_active IP Right Cessation
- 1972-12-27 DD DD168055*A patent/DD106384A5/xx unknown
- 1972-12-27 CH CH1887672A patent/CH587830A5/xx not_active IP Right Cessation
- 1972-12-27 ZA ZA729073A patent/ZA729073B/xx unknown
- 1972-12-28 NO NO4808/72A patent/NO138089C/no unknown
- 1972-12-28 PL PL1972175731A patent/PL84244B1/pl unknown
- 1972-12-28 SE SE7217089A patent/SE405120B/xx unknown
- 1972-12-28 GB GB5988172A patent/GB1395772A/en not_active Expired
- 1972-12-28 FI FI3686/72A patent/FI54920C/fi active
- 1972-12-28 HU HUBO5306A patent/HU165306B/hu unknown
- 1972-12-28 PL PL1972159831A patent/PL85284B1/pl unknown
- 1972-12-28 IL IL41198A patent/IL41198A/en unknown
- 1972-12-28 CA CA160,145A patent/CA1028702A/en not_active Expired
- 1972-12-29 FR FR7247013A patent/FR2166204B1/fr not_active Expired
- 1972-12-29 NL NL7217795A patent/NL7217795A/xx not_active Application Discontinuation
- 1972-12-29 IE IE1805/72A patent/IE37815B1/xx unknown
-
1974
- 1974-04-16 ES ES425329A patent/ES425329A1/es not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2687556C1 (ru) * | 2018-12-24 | 2019-05-15 | Акционерное общество "Федеральный научно-производственный центр "Алтай" | Способ получения 7-хлор-1,3-дигидро-1-метил-5-фенил-2Н-1,4-бензодиазепин-2-она |
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