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US3987052A
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6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines
Assignee: Pharmacia and Upjohn Co
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Filing: 1969-10-29
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Granted: 1976-10-19
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Expires: 1989-10-29
Abstract
Abstract 6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula (IV): ##SPC1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, phenyl, benzyl and -COOR' in which R' is alkyl of 1 to 4 carbon atoms, inclusive; wherein R 1 is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive; and wherein R 2 , R 3 , R 4 and R 5 are selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, halogen, nitro, cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkanoylamino and dialkylamino in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive, are produced by condensing a 1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione of the formula (I): ##SPC2## wherein R 1 , R 2 , R 3 , R 4 and R 5 are defined as above, with an organic acid hydrazide of the formula: ##EQU1## wherein R is defined as above. The new products of formula IV including their pharmacologically acceptable acid addition salts are useful as sedatives, tranquilizers and muscle relaxants in mammals and birds.
Inventors
- 👤 Jackson B. Hester, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 12:43
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; C07D243/00; C07D243/06; C07D243/10; C07D243/14; C07D243/16; C07D243/18; C07D243/20
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
110 words
A 6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine of the formula: ##SPC4## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, phenyl, and benzyl whwerein R 1 is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive; and wherein R 2 , R 3 , R 4 , and R 5 are selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, halogen, nitro cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkanoylamino and dialkylamino in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive, and their pharmacologically acceptable acid addition salts.
Claim 2
Dependent Claim
110 words
A 6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine of the formula: ##SPC4## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, phenyl, and benzyl whwerein R 1 is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive; and wherein R 2 , R 3 , R 4 , and R 5 are selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, halogen, nitro cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkanoylamino and dialkylamino in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive, and their pharmacologically acceptable acid addition salts.
Claim 3
Dependent Claim
34 words
The compound of claim 1 wherein R is methyl, R 1 , R 2 , R 3 , and R 5 are hydrogen and R 4 is 8-chloro and the compound is therefore 8-chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
Claim 4
Dependent Claim
34 words
The compound of claim 1 wherein R is methyl, R 1 and R 5 are hydrogen, R 2 is 2-fluoro, R 3 is 6-fluoro, R 4 is 8-chloro, and the compound is therefore 8-chloro-1-methyl-6-(2,6-difluorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
Claim 5
Dependent Claim
33 words
The compound of claim 1 wherein R is methyl, R 1 , R 2 and R 5 are hydrogen, R 3 is o-fluoro, R 4 is 8-chloro and the compound is therefore 8-chloro-1-methyl-6-(o-fluorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
Claim 6
Dependent Claim
31 words
The compound of claim 1 wherein R is methyl, R 1 , R 2 , R 3 , R 4 and R 5 are hydrogen and the compound is therefore 1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
Claim 7
Dependent Claim
32 words
The compound of claim 1 wherein R is propyl, R 1 , R 2 , R 3 and R 5 are hydrogen, R 4 is 8-chloro and the compound is therefore 8-chloro-1-propyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
Claim 8
Dependent Claim
32 words
The compound of claim 1 wherein R is phenyl, R 1 , R 2 , R 3 and R 5 are hydrogen, R 4 is 8-chloro and the compound is therefore 8-chloro-1,6-diphenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
Claim 9
Dependent Claim
32 words
The compound of claim 1 wherein R is benzyl, R 1 , R 2 , R 3 and R 5 are hydrogen, R 4 is 8-chloro and the compound is therefore 1-benzyl-8-chloro-6-phenyl-4H-s-triazolo[4,34,3-a][1,4]benzodiazepine.
Claim 10
Dependent Claim
32 words
The compound of claim 1 wherein R is ethyl, R 1 , R 2 , R 3 and R 5 are hydrogen, R 4 is 8-chloro and the compound is therefore 1-ethyl-8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
Claim 11
Dependent Claim
32 words
The compound of claim 1 wherein R is methyl, R 1 , R 2 , R 3 and R 5 are hyrogen, R 4 is 8-trifluoromethyl and the compound is therefore 1-methyl-6-phenyl-8-(trifluoromethyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
Claim 12
Dependent Claim
32 words
The compound of claim 1 wherein R is methyl, R 1 , R 2 , R 3 and R 5 are hydrogen, R 4 is 8-nitro and the compound is therefore 1-methyl-8-nitro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
Claim 13
Dependent Claim
33 words
The compound of claim 1 wherein R is methyl, R 1 , R 2 and R 5 are hydrogen, R 3 is o-chloro, R 4 is 8-chloro and the compound is therefore 8-chloro-1-methyl-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
Claim 14
Dependent Claim
30 words
The compound of claim 1 wherein R, R 1 , R 2 , R 3 and R 5 are hydrogen, R 4 is 8-chloro and the compound is therefore 8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
Claim 15
Dependent Claim
33 words
The compound of claim 1 wherein R is methyl, R 1 , R 2 , R 3 and R 5 are hydrogen and R 4 is 8-methylthio and the compound is therefore 8-methylthio-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
Claim 16
Dependent Claim
33 words
The compound of claim 1 wherein R is methyl, R 1 , R 2 , R 3 and R 5 are hydrogen and R 4 is 8-methoxy and the compound is therefore 8-methoxy-1-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
References Cited (Backward Citations)
US2891862A
Cited
US3422091A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-10-19 | 1980-04-19 | 1980-10-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-10-19 | 1984-04-19 | 1984-10-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-10-19 | 1988-04-19 | 1988-10-19 | $7700.00 | Window Closed / Lapsed |