US4268672A
Expired / Lapsed
US
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Adenosine deaminase resistant antiviral purine nucleosides and method of preparation
Assignee: University of Minnesota System
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Filing: 1979-01-05
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Granted: 1981-05-19
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Expires: 1999-01-05
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. Acid salts and esters of the purine nucleosides have also been prepared.
Inventors
- 👤 Robert Vince
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 23:50
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; C07D473/36; C07D473/38; C07D473/40; C07D487/00; C07D487/02; C07D487/04; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6561; C07F9/65616
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
175 words
A method of preparation of the purine nucleoside analog having the formula: ##STR9## wherein R is selected from the group of substituent groups consisting of amino, hydroxyl, mercapto, methylmercapto and substituted amino NR'R" wherein R' and R" may be the same or different and are hydrogen, methyl, ethyl, propyl or phenyl, which method comprises: (A) preparing the intermediate ##STR10## wherein X is halogen, by (1) hydrolysing 2-azabicyclo[2.2.1]hept-5-en-3-one under acid conditions. (2) esterifying the carboxyl function of the resulting cis-4-aminocyclo-pent-2-ene carboxylic acid salt, (3) acetylating the amino group of the resulting ester, (4) reducing and acetylating said ester, (5) epoxidizing the resulting acetate, (6) hydrolysing and acetylating the resulting epoxide, (7) forming an amine from the resulting (±)-4α-acetamido-2β, 3α-diacetoxy-1α-cyclopentanemethyl acetate, and (8) condensing said amine with 5-amino-4,6-dihalopyrimidine to produce said intermediate; (B) closing the ring of said intermediate by reaction with a ring closing agent selected from the class consisting of diethoxymethyl acetate and triethyl orthoformate, and (C) replacing the halogen with a substituent from the group consisting of amino, hydroxyl, mercapto, methylmercapto and substituted amino.
Claim 2
Independent Claim
175 words
A method of preparation of the purine nucleoside analog having the formula: ##STR9## wherein R is selected from the group of substituent groups consisting of amino, hydroxyl, mercapto, methylmercapto and substituted amino NR'R" wherein R' and R" may be the same or different and are hydrogen, methyl, ethyl, propyl or phenyl, which method comprises: (A) preparing the intermediate ##STR10## wherein X is halogen, by (1) hydrolysing 2-azabicyclo[2.2.1]hept-5-en-3-one under acid conditions. (2) esterifying the carboxyl function of the resulting cis-4-aminocyclo-pent-2-ene carboxylic acid salt, (3) acetylating the amino group of the resulting ester, (4) reducing and acetylating said ester, (5) epoxidizing the resulting acetate, (6) hydrolysing and acetylating the resulting epoxide, (7) forming an amine from the resulting (±)-4α-acetamido-2β, 3α-diacetoxy-1α-cyclopentanemethyl acetate, and (8) condensing said amine with 5-amino-4,6-dihalopyrimidine to produce said intermediate; (B) closing the ring of said intermediate by reaction with a ring closing agent selected from the class consisting of diethoxymethyl acetate and triethyl orthoformate, and (C) replacing the halogen with a substituent from the group consisting of amino, hydroxyl, mercapto, methylmercapto and substituted amino.
Claim 3
Dependent Claim
23 words
A method according to claim 1 further characterized in that R is NH 2 and said halogen is replaced by reaction with ammonia.
Claim 4
Dependent Claim
23 words
A method according to claim 1 further characterized in that R is OH and said halogen is replaced by refluxing in aqueous acid.
Claim 5
Dependent Claim
22 words
A method according to claim 1 further characterized in that R is SH and said halogen is replaced by reaction with thiourea.
Claim 6
Dependent Claim
37 words
A method according to claim 1 further characterized in that R is SCH 3 , said halogen is replaced by a mercapto group by reaction with thiourea and said mercapto is methylated by reaction with methyl iodide.
References Cited (Backward Citations)
No citation records indexed.
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| 7.5 Years (Year 8) | 1988-05-18 | 1988-11-17 | 1989-05-19 | $3760.00 | Window Closed / Lapsed |
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