US4005099A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1-[(Dimethylamino)-methyl]-6-aryl-4H-imidazo[1,5-a][1,4]benzodiazepines
Assignee: Pharmacia and Upjohn Co
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Filing: 1975-11-21
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Granted: 1977-01-25
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Expires: 1995-11-21
Abstract
Abstract Compounds of the formula III ##STR1## wherein R 1 is hydrogen or methyl; wherein R 2 is hydrogen, fluoro, chloro, bromo, trifluoromethyl, or nitro; and wherein Ar is phenyl, o-chlorophenyl, o-fluorophenyl, o,o-difluorophenyl, or 2-pyridyl, are produced by a two-step process. The compounds of formula III as well as their pharmacologically acceptable acid addition salts thereof are antidepressant agents possessing additionally antianxiety activity. Thus these compounds III are useful in the treatment of anxieties in mammals and birds, and also as anti-depressants in man.
Inventors
- 👤 Martin Gall
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 20:59
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/64; C07D243/00; C07D243/06; C07D243/10; C07D243/14; C07D243/16; C07D487/00; C07D487/02; C07D487/04
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
43 words
A compound of the formula III: ##STR6##wherein R 1 is hydrogen or methyl; wherein R 2 is hydrogen, fluoro, chloro, bromo, trifluoromethyl, or nitro; and wherein A r is phenyl, o-chlorophenyl, o-fluorophenyl, o,o-difluorophenyl, or 2-pyridyl, and the pharmacologically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
43 words
A compound of the formula III: ##STR6##wherein R 1 is hydrogen or methyl; wherein R 2 is hydrogen, fluoro, chloro, bromo, trifluoromethyl, or nitro; and wherein A r is phenyl, o-chlorophenyl, o-fluorophenyl, o,o-difluorophenyl, or 2-pyridyl, and the pharmacologically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
43 words
A compound according to claim 1, of the formula IIIA: ##STR7## wherein R 1 is hydrogen or methyl; wherein R' 2 is hydrogen, fluoro, chloro, or trifluoromethyl; wherein R 3 is hydrogen, chloro, or fluoro, and the pharmacologically acceptable acid addition salts thereof.
Claim 4
Dependent Claim
41 words
A compound according to claim 1, of the formula IIIB: ##STR8##wherein R 1 is hydrogen or methyl; wherein R" 2 is hydrogen, chloro, or fluoro; and wherein R' 3 is hydrogen or chloro and the pharmacologically acceptable acid addition salts thereof.
Claim 5
Dependent Claim
25 words
A compound according to claim 1, wherein A r is 2-pyridyl, R 1 is hydrogen, R 2 is 8-bromo, and the compound is therefore 8-bromo-1-[(dimethylamino)methyl]-6-(2-pyridyl)-4H-imidazo[1,5-a][1,4]benzodiazepine.
Claim 6
Dependent Claim
27 words
A compound according to claim 3, wherein R 1 is CH 3 , R" 2 is 8-chloro, R' 3 is o-chloro and the compound is therefore 8-chloro-1-[(dimethylamino)methyl]-6-(o-chlorophenyl)-3-methyl-4H-imidazo[1,5-a][1,4]benzodiazepine.
Claim 7
Dependent Claim
24 words
A compound according to claim 3, wherein R 1 and R' 3 are hydrogen, R" 2 is 8-chloro, and the compound is therefore 8-chloro-1-[(dimethylamino)methyl]-6-phenyl4H-imidazo[1,5-a][1,4]benzodiazepine.
Claim 8
Dependent Claim
25 words
A compound according to claim 3, wherein R 1 is methyl, R" 2 is 8-chloro, R' 3 is hydrogen, and the compound is therefore 8-chloro-1-[(dimethylamino)methyl]-3-methyl-6-phenyl-4H-imidazo[1,5-a][1,4]benzodiazepine.
Claim 9
Dependent Claim
24 words
A compound according to claim 3, wherein R 1 and R' 3 are hydrogen, R" 2 is o-fluoro and the compound is therefore 8-fluoro-1-[(dimethylamino)methyl]-6-phenyl-4Himidazo[1,5-a][1,4]benzodiazepine.
Claim 10
Dependent Claim
25 words
A compound according to claim 3, wherein R 1 is methyl; R" 2 is 8-trifluoromethyl, R' 3 is hydrogen, and the compound is therefore 8-trifluoromethyl-1-[(dimethylamino)methyl]-3-methyl-6-phenyl-4H-imidazo[1,5-a][1,4]benzodiazepine.
Claim 11
Dependent Claim
25 words
A compound according to claim 3, wherein R 1 is hydrogen, R" 2 is 8-fluoro, R' 3 is o-fluoro; and the compound is therefore 8-fluoro-1-[(dimethylamino)methyl]-6-(o-fluorophenyl)-4H-imidazo[1,5-a][1,4]benzodiazepine.
References Cited (Backward Citations)
US3910946A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-01-25 | 1980-07-26 | 1981-01-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-01-25 | 1984-07-26 | 1985-01-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-01-25 | 1988-07-26 | 1989-01-25 | $7700.00 | Window Closed / Lapsed |