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Details for Patent: 3,984,396

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Details for Patent: 3,984,396

Title: 1-(.beta.,-D-ribofuranosyl)-1,2,4-triazole acid esters
Abstract:Phosphate and carboxylic acid esters of 1-(.beta.-D-ribofuranosyl)-1,2,4-triazoles are prepared by a variety of methods and their antiviral activity reported.
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:05/452,065
Claims:1. A 1-(.beta.-D-ribofuranosyl)-1,2,4-triazole nucleoside of structure ##SPC3##

wherein R.sub.1 is selected from the group consisting of (a) carboxamido, (b) thiocarboxamido, and (c) carboxamidino groups and physiologically acceptable acid addition salts of (c); and wherein X is hydrogen or C.sub.1 -C.sub.18 acyl, at least one X being hydrogen and at least one X being acyl.

2. A 1-(5'-O-acyl-.beta.-D-ribofuranosyl)-1,2,4-triazole according to claim 1.

3. A compound 1-(5'-O-acyl-.beta.-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide according to claim 1.

4. A compound 1-(5'-O-acyl-.beta.-D-ribofuranosyl)-1,2,4-triazole-3-thiocarboxamide according to claim 1.

5. A compound 1-(5'-O-acyl-.beta.-D-ribofuranosyl)-1,2,4-triazole-3-carboxamidine hydrochloride according to claim 1.

6. 1-(5'-O-Benzoyl-.beta.-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide.

7. 1-(5'-O-acetyl-.beta.-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide.

8. 1-(5'-O-butyryl-.beta.-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide.

9. A 1-(.beta.-D-ribofuranosyl)-1,2,4-triazole nucleotide of structure ##SPC4##

wherein R.sub.1 is selected from the group consisting of (a) carboxamido, (b) thiocarboxamido and (c) carboxamidino groups and physiologically acceptable acid addition salts of (c); and wherein R is hydrogen or C.sub.1 -C.sub.18 acyl.

10. A compound according to claim 9 wherein R is hydrogen.

11. 1-(.beta.-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide 2',3'-cyclic phosphate.

12. An hydrolysis product of a compound according to claim 9 comprising a mixture of corresponding 2'- and 3'-monophosphates.

13. A mixture comprising the 2'- and 3'-monophosphates of 1-(.beta.-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide.

14. A compound selected from the group consisting of 2' and 3'-phosphates of a compound of a structure: ##SPC5##

wherein R.sub.1 is selected from the group consisting of (a) carboxamido, (b) thiocarboxamido, and (c) carboxamidino groups and physiologically acceptable acid addition salts of (c).
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