GB1392327A - Triazolo diazepine derivatives and processes for the production thereof - Google Patents
Triazolo diazepine derivatives and processes for the production thereofInfo
- Publication number
- GB1392327A GB1392327A GB1570272A GB1570272A GB1392327A GB 1392327 A GB1392327 A GB 1392327A GB 1570272 A GB1570272 A GB 1570272A GB 1570272 A GB1570272 A GB 1570272A GB 1392327 A GB1392327 A GB 1392327A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzodiazepine
- compound
- chloro
- reacting
- phenyl
- 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.)
- Expired
Links
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
Abstract
1392327 Triazolo-benzodiazepine derivatives CIBA-GEIGY AG 5 April 1972 [8 April 1971] 15702/72 Heading C2C Novel compounds of the Formula I wherein R 1 is hydrogen or C 1-3 alkyl, each of R 2 is a C 1-4 alkyl group or the R 2 symbols together are a divalent C 2-5 saturated aliphatic hydrocarbon and wherein each of the rings A and B is unsubstituted or substituted by one or more bromine, chlorine, fluorine atoms, trifluoromethyl, nitro or C 1-6 alkyl or alkoxyl substituents, and the 5-oxides and acid addition salts thereof may be prepared by (1) cyclizing a compound II wherein X is mercapto, C 1-2 alkoxy or alkylthio optionally activated by a substituent, or an unsubstituted or mono- or di-substituted amino group with a compound III (2) reacting a compound IV with R 2 OR or HOR 2 -R 2 OH; (3) reacting a compound VII with a reactive ester of VIII optionally followed in each case by forming the 5-oxide and/or salts thereof. 2 - (Methylthio) - 5 - (o - chlorophenyl) - 3H- 1,4-diazepine may be prepared by reacting the corresponding thione in dimethyl sulphate. 6 - Phenyl - 8 - chloro - 4H - s - triazolo- [4,3-a][1,4]benzodiazepine- 1 - carboxaldehyde may be prepared by reacting 2-methylthio-5- phenyl - 7 - chloro - 3H - 1,4 - benzodiazepine with benzyloxyacethydrazide to yield 1 -benzyloxymethyl - 6 - phenyl - 8 - chloro - 4H - striazolo[4,3-a][1,4]benzodiazepine which is debenzylated to yield 6-phenyl-8-chloro-4H-striazolo[4,3-a][1,4]benzodiazepine - 1 - methanol which is oxidized to the required compound. Pharmaceutical compositions of the compounds I with the usual excipients show tranquillizing, sedative, muscle relaxant and antiepileptic activity when administered orally, parenterally or rectally.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH523371 | 1971-04-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1392327A true GB1392327A (en) | 1975-04-30 |
Family
ID=4290168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1570272A Expired GB1392327A (en) | 1971-04-08 | 1972-04-05 | Triazolo diazepine derivatives and processes for the production thereof |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3867536A (en) |
| JP (1) | JPS5614671B1 (en) |
| AR (3) | AR193382A1 (en) |
| AT (2) | AT317230B (en) |
| AU (1) | AU472767B2 (en) |
| BE (1) | BE781816A (en) |
| CA (1) | CA991639A (en) |
| CH (1) | CH545302A (en) |
| CS (3) | CS178449B2 (en) |
| DD (1) | DD97655A5 (en) |
| DE (1) | DE2215939A1 (en) |
| DK (1) | DK141965B (en) |
| FI (1) | FI52583C (en) |
| FR (1) | FR2132767B1 (en) |
| GB (1) | GB1392327A (en) |
| HU (1) | HU165318B (en) |
| IE (1) | IE36231B1 (en) |
| IL (1) | IL39051A (en) |
| NL (1) | NL7204700A (en) |
| NO (1) | NO134839C (en) |
| PL (1) | PL83566B1 (en) |
| SE (1) | SE413408B (en) |
| SU (3) | SU499808A3 (en) |
| ZA (1) | ZA721896B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH572056A5 (en) * | 1972-11-28 | 1976-01-30 | Ciba Geigy Ag |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987052A (en) * | 1969-03-17 | 1976-10-19 | The Upjohn Company | 6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines |
| BE759099A (en) * | 1969-11-18 | 1971-04-30 | Takeda Chemical Industries Ltd | PROCESS FOR MANUFACTURING HETEROCYCLIC COMPOUNDS |
| US3681343A (en) * | 1971-05-11 | 1972-08-01 | Upjohn Co | 6-phenyl-s-triazolo{8 4,3-a{9 {8 1,4{9 {0 benzodiazepines |
-
1971
- 1971-04-08 CH CH1212973A patent/CH545302A/en not_active IP Right Cessation
-
1972
- 1972-03-20 ZA ZA721896A patent/ZA721896B/en unknown
- 1972-03-21 IL IL39051A patent/IL39051A/en unknown
- 1972-03-27 SE SE7203938A patent/SE413408B/en unknown
- 1972-03-28 IE IE404/72A patent/IE36231B1/en unknown
- 1972-03-29 FI FI720882A patent/FI52583C/en active
- 1972-03-30 CA CA138,606A patent/CA991639A/en not_active Expired
- 1972-03-30 US US239780A patent/US3867536A/en not_active Expired - Lifetime
- 1972-04-01 DE DE19722215939 patent/DE2215939A1/en not_active Withdrawn
- 1972-04-05 GB GB1570272A patent/GB1392327A/en not_active Expired
- 1972-04-06 AU AU40820/72A patent/AU472767B2/en not_active Expired
- 1972-04-06 HU HUCI1223A patent/HU165318B/hu unknown
- 1972-04-06 NO NO1163/72A patent/NO134839C/no unknown
- 1972-04-06 DD DD162097A patent/DD97655A5/xx unknown
- 1972-04-07 DK DK169972AA patent/DK141965B/en unknown
- 1972-04-07 CS CS435A patent/CS178449B2/cs unknown
- 1972-04-07 AR AR241356A patent/AR193382A1/en active
- 1972-04-07 FR FR7212299A patent/FR2132767B1/fr not_active Expired
- 1972-04-07 AT AT781173A patent/AT317230B/en not_active IP Right Cessation
- 1972-04-07 AT AT302172A patent/AT317222B/en not_active IP Right Cessation
- 1972-04-07 CS CS2330A patent/CS178406B2/cs unknown
- 1972-04-07 NL NL7204700A patent/NL7204700A/xx not_active Application Discontinuation
- 1972-04-07 CS CS434A patent/CS178448B2/cs unknown
- 1972-04-07 SU SU1771052A patent/SU499808A3/en active
- 1972-04-07 PL PL1972154657A patent/PL83566B1/en unknown
- 1972-04-07 BE BE781816A patent/BE781816A/en unknown
- 1972-04-08 JP JP3486172A patent/JPS5614671B1/ja active Pending
-
1973
- 1973-03-26 AR AR247235A patent/AR194991A1/en active
- 1973-03-26 AR AR247234A patent/AR193942A1/en active
- 1973-10-23 SU SU1964147A patent/SU482045A3/en active
- 1973-10-23 SU SU1964148A patent/SU489332A3/en active
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |