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US 4,902,794 AGranted
Triazolo-benzodiazepines
AssigneeThe Upjohn Company
InventorJackson B. Hester, Jr.
Life of this patent
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AssigneeThe Upjohn Company
InventorJackson B. Hester, Jr.
Estimating the term…
1-Substituted-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula (III): ##STR1## wherein R is selected from the group consisting of hydroxy, esters thereof, and alkoxy, in which the alkyl group is of 1 to 3 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): ##STR2## 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 (II): ##STR3## wherein R' is selected from the group consisting of hydroxy, and alkoxy defined as above. When R' is hydroxy, esters can be made in conventional manner. The new products of formula III including their pharmacologically acceptable acid addition salts and N-oxides are useful as sedatives, tranquilizers and muscle relaxants in mammals and birds.
A 1-substituted 6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine of the formula (III):
A 1-substituted-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine of the formula (V):
Esters of alkanoic acids of 2 to 18 carbon atoms, benzoic, phenylacetic, succinic, or glutaric acid with a compound of the formula ##STR16## wherein R is hydroxy and wherein R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive;
Ester of alkanoic acid of 2 to 18 carbon atoms, benzoic, phenylacetic, succinic or glutaric acid with a compound of the formula ##STR17## wherein R" is hydroxy;
Ester or alkanoic acids of 2 to 18 carbon atoms, benzoic, phenylacetic, succinic, or glutaric acid with a compound of the formula ##STR18## wherein R is hydroxy;
8-Chlo ro-1-(hydroxymethyl)-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine acetate ester.
8-Chloro-1- (hydroxymethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine hydrogen succinate ester.
8-chloro-1-(hydroxymet hyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
Dependencies are inferred from the claim text.