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Details for Patent: 5,151,426

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Details for Patent: 5,151,426

Title: 2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties
Abstract:Methods and compositions for preventing or treating human immunodeficiency virus (HIV) infections characterized by 2-substituted-5-substituted-1,3-oxathiolanes.
Inventor(s): Belleau; Bernard (Westmount, CA), Nguyen-Ba; Nghe (Brossard, CA)
Assignee: BioChem Pharma Inc. (Laval, CA)
Filing Date:Jun 17, 1991
Application Number:07/716,627
Claims:1. A 1,3-oxathiolane of formula (A), the geometric and optical isomers thereof, and mixtures of those isomers: ##STR17## wherein: Z is selected from a group consisting of sulfur, sulfoxide, and sulfone;

R.sub.1 is selected from a group consisting of hydrogen, and an acyl group having 1 to 16 carbon atoms; and

R.sub.2 is a heterocyclic radical selected from a group consisting of: ##STR18##

2. A compound according to claim 1 wherein R.sub.1 is hydrogen and R.sub.2 is adenosin-9'-yl.

3. A compound according to claim 1 wherein R.sub.1 is hydrogen and R.sub.2 is inosin-9'-yl.

4. A compound according to claim 1 wherein R.sub.1 is hydrogen and R.sub.2 is 2'-amino-purin-9'-yl.

5. A compound according to claim 1 wherein R.sub.1 is hydrogen and R.sub.2 is 2'-amino-6'-chloro-purin-9'-yl.

6. A compound according to claim 1 wherein R.sub.1 is hydrogen and R.sub.2 is 2,40 ,6'-diamino-purin-9'-yl.

7. A compound according to claim 1 wherein R.sup.1 is hydrogen and R.sub.2 is quanin-9'-yl.

8. The compound according to claim 1, wherein R.sub.1 is selected from a group consisting of acetyl, hexanoyl and benzoyl which may be substituted by a group selected from the group consisting of OH, OCH.sub.3, NO.sub.2, CF.sub.3 and NH.sub.2.

9. A method for treating human immunodeficiency virus infections in animals and humans, characterized by administering an antiviral effective amount of a compound selected from the group consisting of a 1,3; -xoathiolane of formula (A), the geomtric and optical isomers thereof, and mixtures of those isomers: ##STR19## wherein: Z is selected from a group consisting of sulfur, sulfoxide, and sulfone;

R.sub.1 is selected from a group consisting of hydrogen, and an acyl group having 1 to 16 carbon atoms; and

R.sub.2 is a heterocyclic radical selected from a group consisting of: ##STR20##

10. A pharmaceutical composition for use in treating HIV infections in animals and humans, characterized by an antiviral effective amount of a compound selected from the group consisting of a 1,3-oxathiolane of formula (A), the geometric and optical isomers thereof, and mixtures of those isomers; ##STR21## wherein: Z is selected from a group consisting of sulfur, sulfoxide, and sulfone;

R.sub.1 is selected from a group consisting of hydrogen, and an acyl group having 1 to 16 carbon atoms; and

R.sub.2 is heterocyclic radical selected from a group consisting of: ##STR22##
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