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Generated: July 25, 2017

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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: IAF BioChem International, Inc. (Montreal, CA)
Application Number:07/308,101
Patent Claims: 1. A 1,3-oxathiolane of formula (A), the geometric and optical isomers thereof, and mixtures of those isomers: ##STR23## wherein: Z is selected from the group consisting of sulfur, sulfoxide, and sulfone;

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

R.sub.2 is a heterocyclic radical selected from the group consisting of: ##STR24## R.sub.3 and R.sub.4 are independently selected from the group consisting of hydrogen and C.sub.1-6 alkyl groups;

R.sub.5 is selected from the group of hydrogen, C.sub.1-6 alkyl, bromine, chlorine, fluorine, and iodine; and

X and Y are independently selected from the group consisting of bromine, chlorine, fluorine, iodine, amino and hydroxyl groups.

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

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

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

5. The compound according to claim 1 where R.sub.1 is selected from the 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.

6. A method for treating human immunodeficiency virus infections in animals and humans, characterized by administering an antiviral effective amount of a compound of a 1,3-oxathiolane of Formula (A), the geometric and optical isomers thereof, and mixtures of those isomers: ##STR25## wherein: Z is selected from the group consisting of sulfur, sulfoxide and sulfone;

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

R.sub.2 is a heterocyclic radical selected from the group consisting of: ##STR26## R.sub.3 and R.sub.4 are independently selected from the group consisting of hydrogen and C.sub.1-6 alkyl groups;

R.sub.5 is selected from the group of hydrogen, C.sub.1-6 alkyl, bromine, chlorine, fluorine, and iodine; and

X and Y are independently selected from the group consisting of bromine, chlorine, fluorine, iodine, amino and hydroxyl groups.

7. 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: ##STR27## wherein: Z is selected from the group consisting of sulfur, sulfoxide and sulfone;

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

R.sub.2 is a heterocyclic radical selected from the group consisting of: ##STR28## R.sub.3 and R.sub.4 are independently selected from the group consisting of hydrogen and C.sub.1-6 alkyl groups;

R.sub.5 is selected from the group of hydrogen, C.sub.1-6 alkyl, bromine, chlorine, fluorine, and iodine; and

X and Y are independently selected from the group consisting of bromine, chlorine, fluorine, iodine, amino and hydroxyl groups.

8. A compound of Formula IX the geometric and optical isomers thereof, and mixtures of those isomers. ##STR29##

9. A compound of Formula X the geometric and optical isomers thereof, and mixtures of those isomers. ##STR30##

10. A compound of Formula XI the geometric and optical isomers thereof, and mixtures of those isomers. ##STR31##

11. A compound of Formula XII the geometric and optical isomers thereof, and mixtures of those isomers. ##STR32##

12. The compound according to claim 1 wherein R.sub.1 is an aroyl.

13. The compound according to claim 1 wherein R.sub.1 is a benzoyl substituted in any position by at least one bromine, chlorine, fluorine, iodine, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, nitro or trifluoromethyl group.
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