USRE29835E
Expired / Lapsed
US
⏱️ 0.0 years remaining
1,2,4-Triazole nucleosides
Assignee: Viratek Inc
•
Filing: 1977-03-28
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Granted: 1978-11-14
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Expires: 1997-03-28
Abstract
Abstract As antiviral agents and intermediates therefor, 3-substituted 1-(β-D-glycosyl)-1,2,4-triazoles, O-acylated analogs thereof, and 5'- and 3',5'-cyclic phosphates of the triazole nucleosides, "glycosyl" being .[.a pentofuranosyl moiety, preferably one whose 2'-oxygen is trans to the triazole aglycon, e.g., xylofuranosyl,.]. ribofuranosyl, .[.2-0-methylribofuranosyl, etc.,.]. the triazole aglycon being 3-substituted with cyano, methylcarboxylate, carboxamidoxime, carboxamido-, thiocarboxamido, or carboxamidine. Preparation of these nucleosides is by silylation of the substituted triazole followed by glycosylation with the appropriate blocked glycosyl halide. Alternatively, acid-catalyzed fusion of the requisite 1,2,4-triazole with an O-acylated pentofuranose yields the nucleosides.
Inventors
- 👤 Joseph T. Witkowski
- 👤 Roland K. Robins
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 15:30
CPC Classifications
C; C07; C07H; C07H13/00; C07H13/02; C07H13/04; C07H19/00; C07H19/02; C07H19/04; C07H19/056
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
39 words
A compound of structure ##STR8## wherein G is .[.a pentofuranosyl moiety whose 2'-oxygen is trans to the aglycon.]. .Iadd.β-D-ribofuranosyl .Iaddend.and R 1 is selected from the group consisting of ##STR9## (d) physiologically acceptable acid addition salts of (c), ##STR10##
Claim 2
Dependent Claim
39 words
A compound of structure ##STR8## wherein G is .[.a pentofuranosyl moiety whose 2'-oxygen is trans to the aglycon.]. .Iadd.β-D-ribofuranosyl .Iaddend.and R 1 is selected from the group consisting of ##STR9## (d) physiologically acceptable acid addition salts of (c), ##STR10##
Claim 3
Dependent Claim
19 words
A compound selected from the group consisting of 5'-phosphates and 3',5'-cyclic phosphates of a compound according to claim 1.
Claim 4
Dependent Claim
70 words
A compound selected from the group consisting of (I) compounds of structure: ##STR11## wherein .[.one of R 2 and.]. R 3 .[.are.]. .Iadd.is .Iaddend.hydroxyl.[., the other being.]. .Iadd.and R 2 is .Iaddend.hydrogen, and wherein R 1 is selected from the group consisting of ##STR12## (d) physiologicaly acceptable acid addition salts of (c), ##STR13## (II) a 5'-phosphate of a compound (I); and (III) a 3',5'-cyclic phosphate of a compound (I). .[.
Claim 5
Dependent Claim
70 words
A compound selected from the group consisting of (I) compounds of structure: ##STR11## wherein .[.one of R 2 and.]. R 3 .[.are.]. .Iadd.is .Iaddend.hydroxyl.[., the other being.]. .Iadd.and R 2 is .Iaddend.hydrogen, and wherein R 1 is selected from the group consisting of ##STR12## (d) physiologicaly acceptable acid addition salts of (c), ##STR13## (II) a 5'-phosphate of a compound (I); and (III) a 3',5'-cyclic phosphate of a compound (I). .[.
Claim 6
Dependent Claim
11 words
A compound according to claim 3 wherein R 2 is hydrogen..].
Claim 7
Dependent Claim
14 words
A compound according to claim .[.4.]. .Iadd.3 .Iaddend.wherein otherwise free glycosyl hydroxyls are acyl-blocked.
Claim 8
Dependent Claim
16 words
A compound according to claim .[.4.]. .Iadd.3 .Iaddend.wherein R 1 is (a), (b), (c) or (d).
Claim 9
Dependent Claim
15 words
A compound according to claim .[.4.]. .Iadd.3 .Iaddend.wherein R 1 is (a), (b) or (d).
Claim 10
Dependent Claim
86 words
The ammonium or alkali metal salt of a 5'-phosphate (II) according to claim 7. .[.9. A compound according to claim 3 wherein R 3 is hydrogen..]. .[.10. A compound according to claim 9 wherein otherwise free glycosyl hydroxyls are acyl-blocked..]. .[.11. A compound according to claim 9 and wherein R 1 is (a), (b), (c) or (d)..]. .[.12. A compound according to claim 9 wherein R 1 is (a), (b) or (d)..]. .[.13. The ammonium or alkali metal salt of a 5'-phosphate (II) according to claim
Claim 11
Dependent Claim
11 words
.]. 14. A compound (I) according to claim .[.4.]. .Iadd.3. .Iaddend.
Claim 12
Dependent Claim
33 words
A compound (II) according to claim .[.4.]. .Iadd.3. .Iaddend. 16. A compound (III) according to claim .[.4.]. .Iadd.3. .Iaddend. .[.17. A compound (I) according to claim 9..]. .[.18. A compound (II) according to
Claim 13
Dependent Claim
18 words
claim 9..]. .[.19. A compound (III) according to claim 9..]. 20. The ammonium salt of the 5'-phosphate of
Claim 14
Dependent Claim
1 words
1-(β-D-ribofuransoyl)-1,2,4-triazole-3-carboxamide.
Claim 15
Dependent Claim
1 words
1-(β-D-ribofuransoyl)-1,2,4-triazole-3-carboxamide.
Claim 16
Dependent Claim
1 words
1(-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide.
Claim 17
Dependent Claim
1 words
1(-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide.
Claim 18
Dependent Claim
1 words
1-(β-D-ribofuranosyl)-1,2,4-triazole-3-thiocarboxamide.
Claim 19
Dependent Claim
1 words
1-(β-D-ribofuranosyl)-1,2,4-triazole-3-thiocarboxamide.
Claim 20
Dependent Claim
3 words
1-(β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamidine. 24. 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxa
Claim 21
Dependent Claim
3 words
1-(β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamidine. 24. 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxa
Claim 22
Dependent Claim
5 words
mide. 25. 1-(β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide hydrochloride. .[.26.
Claim 23
Dependent Claim
5 words
mide. 25. 1-(β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide hydrochloride. .[.26.
Claim 24
Dependent Claim
4 words
1-(β-D-xylofuranosyl)-1,2,4-triazole-3-carboxamide..]. 27. 1-(β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide 3',5'-cyclic
Claim 25
Dependent Claim
4 words
1-(β-D-xylofuranosyl)-1,2,4-triazole-3-carboxamide..]. 27. 1-(β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide 3',5'-cyclic
Claim 26
Dependent Claim
11 words
phosphate. 28. The ammonium salt of the compound of claim 27.
References Cited (Backward Citations)
US3541079A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-11-13 | 1982-05-15 | 1982-11-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-11-13 | 1986-05-15 | 1986-11-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-11-13 | 1990-05-15 | 1990-11-14 | $7700.00 | Window Closed / Lapsed |