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Claims for Patent: 3,987,052

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Claims for Patent: 3,987,052

Title: 6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines
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.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive; and wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.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.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.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.
Inventor(s): Hester, Jr.; Jackson B. (Kalamazoo, MI)
Assignee: The Upjohn Company (Kalamazoo, MI)
Application Number:04/872,394
Patent Claims: 1. 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.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive; and wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.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.

2. The compound of claim 1 wherein R is methyl, R.sub.1, R.sub.2, R.sub.3, and R.sub.5 are hydrogen and R.sub.4 is 8-chloro and the compound is therefore 8-chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.

3. The compound of claim 1 wherein R is methyl, R.sub.1 and R.sub.5 are hydrogen, R.sub.2 is 2-fluoro, R.sub.3 is 6-fluoro, R.sub.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]benzodia zepine.

4. The compound of claim 1 wherein R is methyl, R.sub.1, R.sub.2 and R.sub.5 are hydrogen, R.sub.3 is o-fluoro, R.sub.4 is 8-chloro and the compound is therefore 8-chloro-1-methyl-6-(o-fluorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepi ne.

5. The compound of claim 1 wherein R is methyl, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen and the compound is therefore 1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.

6. The compound of claim 1 wherein R is propyl, R.sub.1, R.sub.2, R.sub.3 and R.sub.5 are hydrogen, R.sub.4 is 8-chloro and the compound is therefore 8-chloro-1-propyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepi ne.

7. The compound of claim 1 wherein R is phenyl, R.sub.1, R.sub.2, R.sub.3 and R.sub.5 are hydrogen, R.sub.4 is 8-chloro and the compound is therefore 8-chloro-1,6-diphenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.

8. The compound of claim 1 wherein R is benzyl, R.sub.1, R.sub.2, R.sub.3 and R.sub.5 are hydrogen, R.sub.4 is 8-chloro and the compound is therefore 1-benzyl-8-chloro-6-phenyl-4H-s-triazolo[4,34,3-a][1,4]benzodiaz epine.

9. The compound of claim 1 wherein R is ethyl, R.sub.1, R.sub.2, R.sub.3 and R.sub.5 are hydrogen, R.sub.4 is 8-chloro and the compound is therefore 1-ethyl-8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepin e.

10. The compound of claim 1 wherein R is methyl, R.sub.1, R.sub.2, R.sub.3 and R.sub.5 are hyrogen, R.sub.4 is 8-trifluoromethyl and the compound is therefore 1-methyl-6-phenyl-8-(trifluoromethyl)-4H-s-triazolo[4,3-a][1,4]benzodiazep ine.

11. The compound of claim 1 wherein R is methyl, R.sub.1, R.sub.2, R.sub.3 and R.sub.5 are hydrogen, R.sub.4 is 8-nitro and the compound is therefore 1-methyl-8-nitro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.

12. The compound of claim 1 wherein R is methyl, R.sub.1, R.sub.2 and R.sub.5 are hydrogen, R.sub.3 is o-chloro, R.sub.4 is 8-chloro and the compound is therefore 8-chloro-1-methyl-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepi ne.

13. The compound of claim 1 wherein R, R.sub.1, R.sub.2, R.sub.3 and R.sub.5 are hydrogen, R.sub.4 is 8-chloro and the compound is therefore 8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.

14. The compound of claim 1 wherein R is methyl, R.sub.1, R.sub.2, R.sub.3 and R.sub.5 are hydrogen and R.sub.4 is 8-methylthio and the compound is therefore 8-methylthio-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.

15. The compound of claim 1 wherein R is methyl, R.sub.1, R.sub.2, R.sub.3 and R.sub.5 are hydrogen and R.sub.4 is 8-methoxy and the compound is therefore 8-methoxy-1-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
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