2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties
AssigneeIAF BioChem International, Inc.
InventorsBernard Belleau, Nghe Nguyen-Ba
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Abstract
Methods and compositions for preventing or treating human immunodeficiency virus (HIV) infections characterized by 2-substituted-5-substituted-1,3-oxathiolanes.
Claims13
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.
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.
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.
A compound of Formula IX the geometric and optical isomers thereof, and mixtures of those isomers. ##STR29##
A compound of Formula X the geometric and optical isomers thereof, and mixtures of those isomers. ##STR30##
A compound of Formula XI the geometric and optical isomers thereof, and mixtures of those isomers. ##STR31##
A compound of Formula XII the geometric and optical isomers thereof, and mixtures of those isomers. ##STR32##
Dependencies are inferred from the claim text.