1-Substituted-6-phenyl-4H-s-triazolo{8 4,3-a{9 {8 1,4{9 benzodiazepines

Abstract

Abstract 6-Phenyl-4H-s-triazolo(4,3-a)(1,4)benzodiazepines of the formula (III): wherein R is selected from the group consisting of cyano, nitro, alkylthio in which the alkyl groups are of 1 to 3 carbon atoms, inclusive, and -COOR'''' in which R'''' is an alkyl group defined as above; wherein R1 is selected from the group consisting of hydrogen and alkyl, defined as above, and wherein R2, R3, R4, and R5 are selected from the group consisting of hydrogen, alkyl defined as above, halogen, nitro, cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, and alkanoylamino, in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive, and dialkylamino in which alkyl is defined as above, are produced by condensing a 1,3-dihydro-5phenyl-2H-1,4-benzodiazepine-2-thione of the formula (I): wherein R1, R2, R3, R4, and R5 are defined as above, with an organic acid hydrazide of the formula (II): wherein R'' is selected from the groups consisting of cyano, nitro, and alkylthio in which the alkyl groups are defined as above, or by hydrolyzing a compound in which R'' is -CN, with an alcohol, water and hydrogen chloride to obtain a product III wherein R is -COOR'''', and R'''' is alkyl, defined as above. The new products of formula III including their pharmacologically acceptable acid addition salts are useful as sedatives, tranquilizers and muscle relaxants in mammals and birds.

Inventors

• 👤 Jr Jackson B Hester

Bibliographic Details