CH651565A5 - Procede de preparation d'imidazobenzodiazepines ainsi que de leurs sels. - Google Patents
Procede de preparation d'imidazobenzodiazepines ainsi que de leurs sels. Download PDFInfo
- Publication number
- CH651565A5 CH651565A5 CH1896/82A CH189682A CH651565A5 CH 651565 A5 CH651565 A5 CH 651565A5 CH 1896/82 A CH1896/82 A CH 1896/82A CH 189682 A CH189682 A CH 189682A CH 651565 A5 CH651565 A5 CH 651565A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- piperazin
- alkyl
- product
- radical
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 150000003839 salts Chemical class 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- -1 4-phenyl-piperazin-1-yl Chemical group 0.000 claims description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 2
- 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 description 2
- 239000000047 product Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- IBYCDDNFZLAIAO-UHFFFAOYSA-N 2,4-dihydroimidazo[1,2-a][1,4]benzodiazepin-1-one Chemical compound C1N=CC2=CC=CC=C2N2C(=O)CN=C21 IBYCDDNFZLAIAO-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QQUIWIVTEWQHKA-UHFFFAOYSA-N 3h-1,4-benzodiazepine Chemical compound C1=NCC=NC2=CC=CC=C21 QQUIWIVTEWQHKA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical group [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229960002195 perazine Drugs 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- JWALPKATZIMQNG-UHFFFAOYSA-N azepine-2-thione Chemical compound S=C1C=CC=CC=N1 JWALPKATZIMQNG-UHFFFAOYSA-N 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
- 229960002130 benzoin Drugs 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([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
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 150000002238 fumaric acids Chemical class 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- KLNFAMGHSZQYHR-UHFFFAOYSA-N imidazo[4,5-i][1,2]benzodiazepine Chemical class C1=CC=NN=C2C3=NC=NC3=CC=C21 KLNFAMGHSZQYHR-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000002936 tranquilizing effect Effects 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 |
|---|---|
| CH651565A5 true CH651565A5 (fr) | 1985-09-30 |
Family
ID=9256708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1896/82A CH651565A5 (fr) | 1981-03-27 | 1982-03-26 | Procede de preparation d'imidazobenzodiazepines ainsi que de leurs sels. |
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 SE8200271D patent/SE8200271L/xx not_active Application Discontinuation
- 1982-01-19 SE SE8200271A patent/SE448731B/sv not_active IP Right Cessation
- 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 PT PT74669A patent/PT74669B/pt unknown
- 1982-03-26 CH CH1896/82A patent/CH651565A5/fr not_active IP Right Cessation
- 1982-03-26 DE DE19823211243 patent/DE3211243A1/de active Granted
- 1982-03-26 DK DK138682A patent/DK153404C/da not_active IP Right Cessation
- 1982-03-26 CA CA000399537A patent/CA1175823A/fr not_active Expired
- 1982-03-26 GB GB8208933A patent/GB2095674B/en not_active Expired
- 1982-03-26 HU HU82939A patent/HU185092B/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES509284A0 (es) | 1983-01-16 |
| FI821058L (fi) | 1982-09-28 |
| MA19416A1 (fr) | 1982-10-01 |
| ES8302712A1 (es) | 1983-01-16 |
| NL193246C (nl) | 1999-04-02 |
| SE8200271L (sv) | 1982-09-28 |
| FR2502621B1 (enrdf_load_stackoverflow) | 1983-10-28 |
| FR2502621A1 (enrdf_load_stackoverflow) | 1982-10-01 |
| PT74669B (fr) | 1985-01-08 |
| HU185092B (en) | 1984-11-28 |
| AU8094782A (en) | 1982-09-30 |
| DK153404C (da) | 1988-11-21 |
| JPS57169483A (en) | 1982-10-19 |
| NL8201208A (nl) | 1982-10-18 |
| IT1147917B (it) | 1986-11-26 |
| ZA821141B (en) | 1983-01-26 |
| DE3211243A1 (de) | 1982-10-07 |
| CA1175823A (fr) | 1984-10-09 |
| NL193246B (nl) | 1998-12-01 |
| FI821058A0 (fi) | 1982-03-25 |
| IT8248036A0 (it) | 1982-03-19 |
| FI71152C (fi) | 1986-11-24 |
| DK138682A (da) | 1982-09-28 |
| GB2095674B (en) | 1984-10-10 |
| DK153404B (da) | 1988-07-11 |
| GB2095674A (en) | 1982-10-06 |
| AU549222B2 (en) | 1986-01-23 |
| FI71152B (fi) | 1986-08-14 |
| SE448731B (sv) | 1987-03-16 |
| PT74669A (fr) | 1982-04-01 |
| DE3211243C2 (enrdf_load_stackoverflow) | 1993-05-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PFA | Name/firm changed |
Owner name: ROUSSEL-UCLAF TRANSFER- ROUSSEL UCLAF * ROUSSEL UC |
|
| PL | Patent ceased |