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Details for Patent: 3,991,078

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Details for Patent: 3,991,078

Title: N-substituted 1,2,4-triazoles
Abstract:Antiviral 1-(G)-1,2,4-triazole carboxamides, thiocarboxamides and carboxamidines wherein G is an acid labile hydrocarbon moiety, e.g., 1-(.alpha.-alkoxyalkyl), are prepared by, e.g., the acid-catalyzed addition reaction of appropriately substituted 1,2,4-triazole and an .alpha.,.beta.-unsaturated ether.
Inventor(s): Witkowski; Joseph T. (Laguna Niguel, CA), Robins; Roland K. (Santa Ana, CA)
Assignee: ICN Pharmaceuticals, Inc. (Irvine, CA)
Filing Date:Mar 18, 1974
Application Number:05/452,213
Claims:1. An N-substituted 1,2,4-triazole of the structure ##SPC3##

wherein R.sub.1 is selected from the group consisting of carboxamido, thiocarboxamido, cyano, carboxamidino and its physiologically acceptable acid-addition salts and alkyl carboxylate groups and wherein G is a moiety of the structure ##SPC4##

wherein R' and R" are alkyl groups having from 1 to 9 carbon atoms or R'

4. A compound according to claim 2 wherein G is selected from the group

5. A compound according to claim 3 wherein G is selected from the group

14. A method of forming acid labile N-substituted 1,2,4-triazoles which comprises effecting the acid-catalyzed addition reaction, under anhydrous conditions, of 1,2,4-triazole of formula ##SPC5##

wherein R.sub.1 is a cyano, carboxamido, thiocarboxamido or alkylcarboxylate group with an .alpha.,.beta.-unsaturated ether of the formula ##STR2## wherein R" is alkyl of 1 to 9 carbons, inclusive, and R'" is hydrogen or alkyl of 1 to 8 carbon atoms, inclusive, or R" and R'", taken together, are dimethylene or trimethylene to form compounds of structure ##SPC6##

wherein G is as defined in claim 1.
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