SE448731B - Forfarande for framstellning av imidazo/1,2-a//1,4/bensodiazepiner - Google Patents
Forfarande for framstellning av imidazo/1,2-a//1,4/bensodiazepinerInfo
- Publication number
- SE448731B SE448731B SE8200271A SE8200271A SE448731B SE 448731 B SE448731 B SE 448731B SE 8200271 A SE8200271 A SE 8200271A SE 8200271 A SE8200271 A SE 8200271A SE 448731 B SE448731 B SE 448731B
- Authority
- SE
- Sweden
- Prior art keywords
- formula
- piperazin
- group
- compound
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 229940049706 benzodiazepine Drugs 0.000 title description 3
- 150000001557 benzodiazepines Chemical class 0.000 title 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000005843 halogen group Chemical group 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 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- -1 aryl sulfonic acids Chemical class 0.000 description 8
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- DXWPKDSKMVHMJF-UHFFFAOYSA-N imidazo[1,2-a][1,4]benzodiazepin-1-one Chemical compound N1=CC2=CC=CC=C2N2C(=O)C=NC2=C1 DXWPKDSKMVHMJF-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 230000001624 sedative effect Effects 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 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- WIITVKVYCUQKMA-UHFFFAOYSA-N [I].[N+](=O)(O)[O-] Chemical compound [I].[N+](=O)(O)[O-] WIITVKVYCUQKMA-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229950005434 chloropyrilene Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001670 myorelaxant effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8106171A FR2502621B1 (enrdf_load_stackoverflow) | 1981-03-27 | 1981-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE448731B true SE448731B (sv) | 1987-03-16 |
Family
ID=9256708
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8200271A SE448731B (sv) | 1981-03-27 | 1982-01-19 | Forfarande for framstellning av imidazo/1,2-a//1,4/bensodiazepiner |
| SE8200271D SE8200271L (sv) | 1981-03-27 | 1982-01-19 | Nytt forfarande for framstellning av imidazobensodiazepiner samt deras salter |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8200271D SE8200271L (sv) | 1981-03-27 | 1982-01-19 | Nytt forfarande for framstellning av imidazobensodiazepiner samt deras salter |
Country Status (17)
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3872090A (en) * | 1972-07-12 | 1975-03-18 | Boehringer Sohn Ingelheim | 3-(amino-methylene)-5-phenyl-1,4-benzodiazepin-2-ones |
| IL48888A (en) * | 1975-02-15 | 1979-03-12 | Roussel Uclaf | 2-aminomethylene-1,2-dihydro-6-phenyl-1h-imidazo(1,2-a)(1,4) benzodiazepin-1-ones, process for their preparation andpharmaceutical compositions incorporating them |
-
1981
- 1981-03-27 FR FR8106171A patent/FR2502621B1/fr not_active Expired
-
1982
- 1982-01-19 SE SE8200271A patent/SE448731B/sv not_active IP Right Cessation
- 1982-01-19 SE SE8200271D patent/SE8200271L/xx not_active Application Discontinuation
- 1982-02-03 ES ES509284A patent/ES8302712A1/es not_active Expired
- 1982-02-22 ZA ZA821141A patent/ZA821141B/xx unknown
- 1982-02-26 AU AU80947/82A patent/AU549222B2/en not_active Expired
- 1982-03-18 MA MA19621A patent/MA19416A1/fr unknown
- 1982-03-19 IT IT48036/82A patent/IT1147917B/it active
- 1982-03-23 NL NL8201208A patent/NL193246C/nl not_active IP Right Cessation
- 1982-03-24 JP JP57045728A patent/JPS57169483A/ja active Pending
- 1982-03-25 FI FI821058A patent/FI71152C/fi not_active IP Right Cessation
- 1982-03-26 DK DK138682A patent/DK153404C/da not_active IP Right Cessation
- 1982-03-26 HU HU82939A patent/HU185092B/hu not_active IP Right Cessation
- 1982-03-26 DE DE19823211243 patent/DE3211243A1/de active Granted
- 1982-03-26 CA CA000399537A patent/CA1175823A/fr not_active Expired
- 1982-03-26 CH CH1896/82A patent/CH651565A5/fr not_active IP Right Cessation
- 1982-03-26 GB GB8208933A patent/GB2095674B/en not_active Expired
- 1982-03-26 PT PT74669A patent/PT74669B/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI71152C (fi) | 1986-11-24 |
| GB2095674B (en) | 1984-10-10 |
| JPS57169483A (en) | 1982-10-19 |
| NL193246B (nl) | 1998-12-01 |
| SE8200271L (sv) | 1982-09-28 |
| ES509284A0 (es) | 1983-01-16 |
| IT8248036A0 (it) | 1982-03-19 |
| DK153404B (da) | 1988-07-11 |
| AU549222B2 (en) | 1986-01-23 |
| PT74669A (fr) | 1982-04-01 |
| DK138682A (da) | 1982-09-28 |
| FI71152B (fi) | 1986-08-14 |
| CH651565A5 (fr) | 1985-09-30 |
| ES8302712A1 (es) | 1983-01-16 |
| PT74669B (fr) | 1985-01-08 |
| NL8201208A (nl) | 1982-10-18 |
| FI821058L (fi) | 1982-09-28 |
| FR2502621A1 (enrdf_load_stackoverflow) | 1982-10-01 |
| FR2502621B1 (enrdf_load_stackoverflow) | 1983-10-28 |
| FI821058A0 (fi) | 1982-03-25 |
| ZA821141B (en) | 1983-01-26 |
| MA19416A1 (fr) | 1982-10-01 |
| AU8094782A (en) | 1982-09-30 |
| IT1147917B (it) | 1986-11-26 |
| DK153404C (da) | 1988-11-21 |
| CA1175823A (fr) | 1984-10-09 |
| DE3211243C2 (enrdf_load_stackoverflow) | 1993-05-19 |
| NL193246C (nl) | 1999-04-02 |
| DE3211243A1 (de) | 1982-10-07 |
| GB2095674A (en) | 1982-10-06 |
| HU185092B (en) | 1984-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAL | Patent in force |
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| NUG | Patent has lapsed |
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