GB1299151A - 7-phenylpyrimido-benzodiazepine derivatives - Google Patents
7-phenylpyrimido-benzodiazepine derivativesInfo
- Publication number
- GB1299151A GB1299151A GB07986/71A GB1798671A GB1299151A GB 1299151 A GB1299151 A GB 1299151A GB 07986/71 A GB07986/71 A GB 07986/71A GB 1798671 A GB1798671 A GB 1798671A GB 1299151 A GB1299151 A GB 1299151A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloro
- alkyl
- reaction
- reacting
- hydrogen
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1299151 7 - Phenylpyrimido - benzodiazepine derivatives UPJOHN CO 28 May 1971 [18 June 1970] 17986/71 Heading C2C Novel compounds of the Formula IX wherein R 1 is hydrogen, C 1-3 alkyl, hydroxy or acetoxy; R 2 , R 3 , R 4 and R 5 are hydrogen, halogen, nitro cyano, trifluoromethyl, sulphonamido, amino or alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkanoylamino or dialkylamino in which the alkyl moities are C 1-3 ; R 6 is hydrogen, C 1-3 alkyl, phenyl or benzyl and X is oxygen, sulphur or imino and pharmaceutically acceptable salts thereof may be prepared (a) where X is oxygen by reacting a 2-amino substituted 1,4-diazepine I where R 1 <SP>1</SP> is hydrogen or C 1-3 alkyl with a 2- oxetanone to form the corresponding N-acetoacetyl derivative and then cyclizing the intermediate by heating in a high boiling hydrocarbon solvent; (b) where X is sulphur by reaction of IX where X is oxygen with phosphorus pentasulphide and (c) where X is imino, reacting the product of (b) with ammonia; (d) where R 1 is acetoxy by forming the 6-N-oxide and reacting this with acetic anhydride; (e) where R 1 is hydroxy by hydrolysis of the product of (d). The intermediate I may be prepared by reacting the appropriate 2-keto compound with phosphorus pentasulphide to form the 2-thio compound followed by reaction with ammonia to form I. The intermediate 1,3 - dihydro - 7 - chloro- 5 - (2,6 - difluorophenyl) - 2H - 1,4 - benzo. diazepin - 2 - one may be prepared by reaction of m-difluorobenzene with butyl lithium followed by 6-chloro-2-methyl-4H-3,1-benzoxazin- 4 - one to yield 4 - chloro - 2 - (2<SP>1</SP>,6<SP>1</SP> - difluorobenzoyl)acetanilide followed by hydrolysis to 2- amino - 5 - chloro - 2<SP>1</SP>,6<SP>1</SP> - difluorobenzophenone, reaction with bromacetyl bromide to form 2- (2 - bromacetamido) - 5 - chloro - 2<SP>1</SP>,6<SP>1</SP> - difluorobenzophenone, reaction with ammonia to form 2 - (2 - aminoacetamido) - 5 - chloro- 2<SP>1</SP>,6<SP>1</SP>-difluoro benzophenone followed by heating in pyridine to form the required product. Pharmaceutical compositions of the compounds IX show tranquilizing, muscle relaxant and antispasmodic activity when administered orally, parenterally or rectally with the usual excipients.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4760270A | 1970-06-18 | 1970-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1299151A true GB1299151A (en) | 1972-12-06 |
Family
ID=21949903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB07986/71A Expired GB1299151A (en) | 1970-06-18 | 1971-05-28 | 7-phenylpyrimido-benzodiazepine derivatives |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5425040B1 (en) |
| AR (4) | AR198784A1 (en) |
| BE (1) | BE768702A (en) |
| CH (2) | CH569017A5 (en) |
| DE (1) | DE2127812C2 (en) |
| ES (1) | ES392364A1 (en) |
| FR (1) | FR2100782B1 (en) |
| GB (1) | GB1299151A (en) |
| HU (1) | HU163364B (en) |
| IL (1) | IL36948A (en) |
| NL (1) | NL167433C (en) |
| OA (1) | OA03874A (en) |
| PH (1) | PH9777A (en) |
| SE (1) | SE370238B (en) |
| SU (1) | SU406358A3 (en) |
| YU (1) | YU151471A (en) |
| ZA (1) | ZA713364B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE790356A (en) * | 1971-10-21 | 1973-04-20 | Takeda Chemical Industries Ltd | BENZODIAZEPINE DERIVATIVES |
| BE790839A (en) * | 1971-11-02 | 1973-04-30 | Upjohn Co | NEW BENZODIAZEPINES, THEIR PREPARATION PROCESS AND THE MEDICINAL PRODUCT CONTAINING THEM |
| BE793118A (en) * | 1971-12-24 | 1973-06-21 | Takeda Chemical Industries Ltd | BENZODIAZOCINE DERIVATIVES |
| GB1402810A (en) * | 1973-01-15 | 1975-08-13 | Upjohn Co | Pyrimidobenzodiazepines |
| US3842080A (en) * | 1973-01-15 | 1974-10-15 | Upjohn Co | 7-phenylpyrimido(1,2-a)(1,4)benzodiazepin-1(5h)-ones |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1545214A (en) * | 1966-11-23 | 1968-11-08 | Hoffmann La Roche | Process for the preparation of benzodiazepine derivatives |
| BE755139A (en) * | 1969-08-21 | 1971-02-22 | Upjohn Co | BENZODIAZEPINONES DERIVATIVES, THEIR INTERMEDIARIES, AND THEIR PREPARATION |
| BE759099A (en) * | 1969-11-18 | 1971-04-30 | Takeda Chemical Industries Ltd | PROCESS FOR MANUFACTURING HETEROCYCLIC COMPOUNDS |
-
1971
- 1971-05-25 ZA ZA713364A patent/ZA713364B/en unknown
- 1971-05-28 IL IL36948A patent/IL36948A/en unknown
- 1971-05-28 GB GB07986/71A patent/GB1299151A/en not_active Expired
- 1971-06-04 DE DE2127812A patent/DE2127812C2/en not_active Expired
- 1971-06-07 CH CH1638474A patent/CH569017A5/xx not_active IP Right Cessation
- 1971-06-07 CH CH830171A patent/CH560217A5/xx not_active IP Right Cessation
- 1971-06-10 PH PH12532A patent/PH9777A/en unknown
- 1971-06-11 YU YU01514/71A patent/YU151471A/en unknown
- 1971-06-16 HU HUUO70A patent/HU163364B/hu unknown
- 1971-06-16 SE SE7107817A patent/SE370238B/xx unknown
- 1971-06-17 ES ES392364A patent/ES392364A1/en not_active Expired
- 1971-06-17 OA OA54273A patent/OA03874A/en unknown
- 1971-06-17 NL NL7108319.A patent/NL167433C/en not_active IP Right Cessation
- 1971-06-17 FR FR7122104A patent/FR2100782B1/fr not_active Expired
- 1971-06-18 JP JP4338871A patent/JPS5425040B1/ja active Pending
- 1971-06-18 BE BE768702A patent/BE768702A/en not_active IP Right Cessation
- 1971-06-18 SU SU1677616A patent/SU406358A3/ru active
-
1972
- 1972-04-28 AR AR241710A patent/AR198784A1/en active
- 1972-04-28 AR AR241712A patent/AR199278A1/en active
- 1972-04-28 AR AR241713A patent/AR201546A1/en active
- 1972-04-28 AR AR241711A patent/AR200111A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| IL36948A0 (en) | 1971-07-28 |
| DE2127812A1 (en) | 1971-12-23 |
| PH9777A (en) | 1976-03-17 |
| JPS5425040B1 (en) | 1979-08-24 |
| NL167433B (en) | 1981-07-16 |
| NL7108319A (en) | 1971-12-21 |
| BE768702A (en) | 1971-12-20 |
| AR200111A1 (en) | 1974-10-24 |
| CH560217A5 (en) | 1975-03-27 |
| FR2100782A1 (en) | 1972-03-24 |
| AR198784A1 (en) | 1974-07-24 |
| AR201546A1 (en) | 1975-03-31 |
| SE370238B (en) | 1974-10-07 |
| DE2127812C2 (en) | 1982-12-02 |
| OA03874A (en) | 1971-12-24 |
| IL36948A (en) | 1974-11-29 |
| ZA713364B (en) | 1972-01-26 |
| SU406358A3 (en) | 1973-11-05 |
| ES392364A1 (en) | 1973-10-01 |
| AR199278A1 (en) | 1974-08-23 |
| CH569017A5 (en) | 1975-11-14 |
| FR2100782B1 (en) | 1975-01-17 |
| YU151471A (en) | 1979-04-30 |
| HU163364B (en) | 1973-07-28 |
| NL167433C (en) | 1981-12-16 |
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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 |