US3817982A
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2{40 ,3{40 -unsaturated nucleosides and method of making
Assignee: Syntex USA LLC
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Filing: 1971-12-29
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Granted: 1974-06-18
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Expires: 1991-12-29
Abstract
Abstract Novel 2'',3''-unsaturated nucleosides and 2'',3''-dideoxy nucleosides and generic methods of preparing such compounds. The methods are characterized by the step of treating a 2''- or 3''halonucleoside with chromous ion under reactive conditions. The novel 2'',3''-unsaturated nucleosides are useful as intermediates in the preparation of 2'',3''-dideoxy nucleosides which in turn have utility as antibiotic, cytotoxic, and antiviral agents. The novel 2'',3''-unsaturated nucleosides also possess selective DNA terminating properties selective for a number of viruses, and strains of bacteria, and thus are further useful as antiviral or antibiotic agents for these viruses and strains of bacteria.
Inventors
- 👤 J Verheyden
- 👤 J Moffatt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 15:56
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
29 words
The process of claim 1 wherein said treatment is conducted at temperatures in the range of about from 10* to 30*C for about from 5 minutes to 48 hours.
Claim 2
Dependent Claim
35 words
The process of claim 1 wherein said amino complexing agent is selected from the group consisting of ethylenediamine, propylenediamine, ethanolamine, propanolamine, diethanolamine, dipropanolamine, triethanolamine, tripropanolamine, tripropylamine, N,N,N'',N'' -tetramethylethylenediamine, N,N,N'',N''-tetraethylethylenediamine, N,N,N''-trimethylethylenediamine, diethylenediamine, dipropylenediamine, tris(hydroxymethyl)aminoethanol, and tris(hydroxyethyl)aminoethane.
Claim 3
Dependent Claim
20 words
The process of claim 3 wherein said amino complexing agent is selected from the group consisting of ethylenediamine and ethanolamine.
Claim 4
Dependent Claim
32 words
The process of claim 1 wherein said chromous ion is supplied by a chromous salt selected from the group consisting of chromous acetate, chromous chloride, chromous sulfate, chromous perchlorate, and mixtures thereof.
Claim 5
Dependent Claim
23 words
The process of claim 1 wherein said inert solvent is selected from the group consisting of dimethylformamide, ethanol, methanol, acetonitrile, tetrahydrofuran, and water.
Claim 6
Dependent Claim
19 words
The process of claim 6 wherein said inert solvent is selected from the group consisting of dimethylformamide and ethanol.
Claim 7
Dependent Claim
32 words
The process Of claim 5 wherein said chromous salt is chromous perchlorate, said inert organic solvent is dimethylformamide and said complexing agent is selected from the group consisting of ethylenediamine and ethanolamine.
Claim 8
Dependent Claim
33 words
The process of claim 5 wherein said chromous salt is chromous acetate, said inert organic solvent is ethanol and wherein said complexing agent is selected from the group consisting of ethylenediamine and ethanolamine.
Claim 9
Dependent Claim
29 words
The process of claim 8 wherein said treatment is conducted at temperatures in the range of about from 10 to 30*C for about from 5 minutes to 48 hours.
Claim 10
Dependent Claim
29 words
The process of claim 9 wherein said treatment is conducted at temperatures in the range of about from 10 to 30*C for about from 5 minutes to 48 hours.
Claim 11
Dependent Claim
28 words
The process of claim 1 wherein a reactant ratio in the range of about from one to five equivalents of chromous ion per equivalent of halonucleoside is used.
Claim 12
Dependent Claim
23 words
The process of claim 12 wherein about from 1 to 10 equivalents of amino complexing agent is used per equivalent of chromous ion.
Claim 13
Independent Claim
30 words
A method of preparing 2'',3''-dideoxy- Beta -D-glycero-pentofuranosyl nucleosides which comprises the steps of: a. treating a halogenated nucleoside selected from the group consisting of nucleoside compounds represented by the formulas:
Claim 14
Dependent Claim
30 words
The process of claim 14 wherein step b) is effected by treating the product of step a) with a diimide reducing agent in an inert organic solvent under reactive conditions.
Claim 15
Dependent Claim
17 words
The process of claim 15 wherein said diimide reducing agent is generated in situ from potassium azodicarboxylate.
Claim 16
Dependent Claim
40 words
The process of claim 14, wherein B2 is a pyrimidine base other than 5-chloropyrimidine; 5-bromopyrimidine; 5-iodopyrimidine; and S-alkyl-4-thiopyrimidine; and B3 is a purine base other than 7-cyanopurine; 6-mercaptopurine and 6-alkylthiopurine, and wherein said step (b) is effected by catalytic hydrogenation.
Claim 17
Dependent Claim
36 words
The process of claim 14 wherein said inert organic solvent is dimethylformamide and said complexing agent is selected from the group consisting of ethylenediamine and ethanolamine, and wherein said chromous ion is supplied by chromous perchlorate.
Claim 18
Dependent Claim
37 words
The process of claim 14 wherein said inert organic solvent is ethanol and wherein said complexing agent is selected from the group consisting of ethylenediamine and ethanolamine, and wherein said chromous ion is supplied by chromous acetate.
Claim 19
Dependent Claim
9 words
A compound selected from the group having the formulas:
Claim 20
Dependent Claim
8 words
The compound of claim 20 of formula I.
Claim 21
Dependent Claim
9 words
The compound of claim 21 wherein R is hydrogen.
Claim 22
Dependent Claim
23 words
The compound of claim 22 wherein B is a pyrimidine base selected from the group consisting of 5-methylaminouracil; 5-dimethylaminouracil; 5-azauracil; 6-azauracil and S-methyl-4-thiouracil.
Claim 23
Dependent Claim
25 words
The compound of claim 22 wherein B is a pyrimidine base selected from the group consisting of 5-fluorocytosine; 5-trifluoromethylcytosine; 5-methylcytosine; 5-methylaminocytosine; 5-dimethylaminocytosine; 5-azacytosine; and 6-azacytosine.
Claim 24
Dependent Claim
25 words
The compound of claim 22 wherein B is a purine base selected from the group consisting of 2-fluoroadenine; 6-methylaminopurine; 6-dimethylaminopurine; 2-azaadenine; 7-deazaadenine; 7-cyano-7-deazaadenine; and 8-aza-9-deazaadenine.
Claim 25
Dependent Claim
23 words
The compound of claim 22 wherein B is a purine base selected from the group consisting of S-methyl-6-thioguanine; 6-methylthiopurine; 8-azaguanine; 6-mercaptopurine and hypoxanthine.
Claim 26
Dependent Claim
8 words
The compound of claim 20 of formula II.
Claim 27
Dependent Claim
9 words
The compound of claim 27 wherein R is hydrogen.
Claim 28
Dependent Claim
25 words
The compound of claim 28 wherein B is a purine base selected from the group consisting of fluoroadenine; 6-methylaminopurine; 6-dimethylaminopurine; 2-azaadenine; 7-deazaadenine; 7-cyano-7-deazaadenine; and 8-aza-9-deazaadenine.
References Cited (Backward Citations)
US3280104A
Cited
US3281410A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1977-06-17 | 1977-12-17 | 1978-06-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-06-17 | 1981-12-17 | 1982-06-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-06-17 | 1985-12-17 | 1986-06-18 | $7700.00 | Window Closed / Lapsed |