US4138562A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Adenosine deaminase resistant antiviral purine nucleosides and method of preparation
Assignee: University of Minnesota System
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Filing: 1977-02-09
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Granted: 1979-02-06
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Expires: 1997-02-09
Abstract
Abstract The preparation of (+/-)-9-[ alpha -(2 alpha ,3 beta -dihydroxy-4 alpha -(hydroxymethyl) cyclopentyl)]-6-substituted purines: <IMAGE> and (+/-)-3-[ alpha -(2 alpha , 3 beta -dihydroxy-4 alpha -(hydroxymethyl)cyclopentyl)]-7-substituted-v-triazolo[4,5d]pyrimidines: <IMAGE> and their derivatives wherein R is amino, mercapto, methylmercapto, hydroxy, halogen, or substituted amino: <IMAGE> wherein R' and R'' may be the same or different and are of hydrogen, methyl, ethyl, propyl or phenyl. The preparation of the single intermediate from which either of these series of compounds may be synthesized is also disclosed. The compounds exhibit antiviral and antitumor activity.
Inventors
- 👤 Robert Vince
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 16:57
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/48; C07D303/00; C07D303/02; C07D303/36; C07D473/00; C07D473/26; C07D473/32; C07D473/34; C07D487/00; C07D487/02; C07D487/04; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6561; C07F9/65616
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
88 words
A method of preparation of the intermediate having the formula: ##STR7## wherein X is halogen, which method comprises: A) hydrolysing 2 -azabicyclo [2.2.1]hept -5en-3-one under acid conditions, B) esterifying the carboxyl function of the resulting cis-4 -aminocyclo-pent-2-ene carboxylic acid salt, C) acetylating the amino group of the resulting ester, D) reducing and acetylating said ester, E) expoxidizing the resulting acetate, F) hydrolysing and acetylating the resulting epoxide, G) forming an amine from the resulting (+)-4α-acetamido-2β, 3α-diacetoxy-1α-cyclopentanemethyl acetate, and H) condensing said amine with 5-amino-4,6-dihalopyrimidine to produce said intermediate.
Claim 2
Independent Claim
88 words
A method of preparation of the intermediate having the formula: ##STR7## wherein X is halogen, which method comprises: A) hydrolysing 2 -azabicyclo [2.2.1]hept -5en-3-one under acid conditions, B) esterifying the carboxyl function of the resulting cis-4 -aminocyclo-pent-2-ene carboxylic acid salt, C) acetylating the amino group of the resulting ester, D) reducing and acetylating said ester, E) expoxidizing the resulting acetate, F) hydrolysing and acetylating the resulting epoxide, G) forming an amine from the resulting (+)-4α-acetamido-2β, 3α-diacetoxy-1α-cyclopentanemethyl acetate, and H) condensing said amine with 5-amino-4,6-dihalopyrimidine to produce said intermediate.
Claim 3
Dependent Claim
10 words
The intermediate 5-amino-4N-[2α, 3β-dihydroxy-4α-(hydroxymethyl)cyclopent-1α-yl] amino-6-halopyrimidine: ##STR8## wherein X is halogen.
Claim 4
Dependent Claim
10 words
The intermediate 5-amino-4N-[2α, 3β-dihydroxy-4α-(hydroxymethyl)cyclopent-1α-yl] amino-6-halopyrimidine: ##STR8## wherein X is halogen.
References Cited (Backward Citations)
US3825541A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-02-05 | 1982-08-07 | 1983-02-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-02-05 | 1986-08-07 | 1987-02-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-02-05 | 1990-08-07 | 1991-02-06 | $7700.00 | Window Closed / Lapsed |