US4352817A
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Imidazo-diazepines and their use
Assignee: F Hoffmann La Roche AG
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Filing: 1981-02-18
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Granted: 1982-10-05
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Expires: 2001-02-18
Abstract
Abstract There is provided imidazodiazepines of the formula <IMAGE> 1 wherein A together with the two carbon atoms denoted as alpha and beta is the group <IMAGE> X is an oxygen or sulphur atom and R1 is hydrogen or lower alkyl, and either R2 is hydrogen, trifluoromethyl, halogen, cyano or nitro and R3 is hydrogen or R2 is hydrogen and R3 is trifluoromethyl, halogen, cyano, nitro or lower alkyl, and their pharmaceutically acceptable acid addition salts. The compounds are useful in the antagonization of the central-depressant, muscle relaxant, ataxic, blood pressure-lowering and respiratory-depressant properties of 1,4-benzodiazepines which have tranquillizing activity, for example as antidotes in the case of intoxications with 1,4-benzodiazepines which have tranquillizing activity. Also presented are methods to produce the above imidazodiazepines.
Inventors
- 👤 Walter Hunkeler
- 👤 Emilio Kyburz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 20:26
CPC Classifications
C; C07; C07D; C07D495/00; C07D487/00; C07D487/02; C07D487/04; A; A61; A61P; A61P33/00; A61P33/10; A61P39/00; A61P39/02; A61P43/00; C07D243/00; C07D243/06; C07D243/10; C07D243/14; C07D495/12; C07D495/14
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
77 words
A compound of the formula ##STR20## wherein A together with the two carbon atoms denoted as α and β is the group ##STR21## X is an oxygen or sulphur atom and R 1 is hydrogen or lower alkyl, and either R 2 is hydrogen, trifluoromethyl, halogen, cyano or nitro and R 3 is hydrogen or R 2 is hydrogen and R 3 is trifluoromethyl, halogen, cyano, nitro or lower alkyl, and pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
77 words
A compound of the formula ##STR20## wherein A together with the two carbon atoms denoted as α and β is the group ##STR21## X is an oxygen or sulphur atom and R 1 is hydrogen or lower alkyl, and either R 2 is hydrogen, trifluoromethyl, halogen, cyano or nitro and R 3 is hydrogen or R 2 is hydrogen and R 3 is trifluoromethyl, halogen, cyano, nitro or lower alkyl, and pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
10 words
The compound of claim 1, wherein A is group (a).
Claim 4
Dependent Claim
32 words
The compound of claim 2, wherein either R 2 is hydrogen or fluorine and R 3 is hydrogen, or R 2 is hydrogen and R 3 is chlorine, bromine, iodine or cyano.
Claim 5
Dependent Claim
11 words
The compound of claim 3, wherein X is an oxygen atom.
Claim 6
Dependent Claim
10 words
The compound of claim 4, wherein R 1 is methyl.
Claim 7
Dependent Claim
4 words
The compound: t-Butyl 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate.
Claim 8
Dependent Claim
4 words
The compound: t-Butyl 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate.
Claim 9
Dependent Claim
4 words
The compound: t-Butyl 5,6-dihydro-7-iodo-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate.
Claim 10
Dependent Claim
4 words
The compound: t-Butyl 5,6-dihydro-7-iodo-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate.
Claim 11
Dependent Claim
4 words
The compound: t-Butyl 7-bromo-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate.
Claim 12
Dependent Claim
4 words
The compound: t-Butyl 7-bromo-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate.
Claim 13
Dependent Claim
17 words
A compound selected from the group consisting of t-Butyl 7-cyano-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate, t-butyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate, t-butyl 5,6-dihydro-5-methyl-6-thioxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate or t-butyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5a][1,4]benzodiazepine-3-carboxylate.
Claim 14
Dependent Claim
17 words
A compound selected from the group consisting of t-Butyl 7-cyano-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate, t-butyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate, t-butyl 5,6-dihydro-5-methyl-6-thioxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate or t-butyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5a][1,4]benzodiazepine-3-carboxylate.
Claim 15
Independent Claim
117 words
A method of antagonizing, in a patient, the central-depressant, muscle relaxant, ataxic, blood pressure-lowering and respiratory-depressant properties of 1,4-benzodiazepines which have tranquillizing activity which comprises daily administering to said patient from about 0.2 mg to about 500 mg of a compound of the formula ##STR22## wherein A together with the two carbon atoms denoted as α and β is the group ##STR23## X is an oxygen or sulphur atom and R 1 is hydrogen or lower alkyl, and either R 2 is hydrogen, trifluoromethyl, halogen, cyano or nitro and R 3 is hydrogen or R 2 is hydrogen and R 3 is trifluoromethyl, halogen, cyano, nitro or lower alkyl, or the pharmaceutically acceptable acid addition salts thereof.
Claim 16
Independent Claim
117 words
A method of antagonizing, in a patient, the central-depressant, muscle relaxant, ataxic, blood pressure-lowering and respiratory-depressant properties of 1,4-benzodiazepines which have tranquillizing activity which comprises daily administering to said patient from about 0.2 mg to about 500 mg of a compound of the formula ##STR22## wherein A together with the two carbon atoms denoted as α and β is the group ##STR23## X is an oxygen or sulphur atom and R 1 is hydrogen or lower alkyl, and either R 2 is hydrogen, trifluoromethyl, halogen, cyano or nitro and R 3 is hydrogen or R 2 is hydrogen and R 3 is trifluoromethyl, halogen, cyano, nitro or lower alkyl, or the pharmaceutically acceptable acid addition salts thereof.
Claim 17
Dependent Claim
13 words
The method of claim 10 wherein the 1,4-benzodiazepine also has activity against schistosomiasis.
References Cited (Backward Citations)
US4316832A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1985-10-04 | 1986-04-05 | 1986-10-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-10-04 | 1990-04-05 | 1990-10-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-10-04 | 1994-04-05 | 1994-10-05 | $7700.00 | Window Closed / Lapsed |