Hydroxylated erythro-hydroxynonyladenines and related analogs

A compound selected from the group consisting of:

• (a) 9-[2(S),8-dihydroxy-3(R)-nonyl]adenine;
• (b) pharmacologically acceptable salts thereof;
• (c) pharmacologically acceptable isomers thereof which inhibit adenosine deaminase activity with a Ki value between about 10.sup.-7 to about 10.sup.-10 ;
• and,
• (d) pharmacologically acceptable analogs thereof which have a chemical moiety, other than hydrogen or a hydroxy group, bonded to the number 9 carbon atom on the side chain and which inhibit adenosine deaminase activity with a Ki value between about 10.sup.-7 to about 10.sup.-10.

A method of synthesizing a hydroxylated analog of erythro-hydroxynonyladenine in which an erythro-hydroxynonyl side chain attached to an adenyl structure has been modified by addition of at least one moiety that normally is not present in erythro-hydroxynonyladenine, comprising the following steps:

• a. reacting an epoxide reagent having a desired chiral orientation with an alkyl halide reagent having an unsaturated bond between two selected carbon atoms, under conditions which cause said reagents to create an unsaturated aliphatic compound comprising a first portion having a desired chiral orientation and a second portion having an unsaturated bond;
• b. reacting the unsaturated aliphatic compound with at least one third reagent under conditions which cause said third reagent to modify the unsaturated aliphatic compound by adding at least one hydroxyl group to at least one of the two carbon atoms which previously were bonded to each other by the unsaturated bond, thereby creating a hydroxylated saturated aliphatic compound;
• c. completing any additional steps necessary to remove any protective groups and to finish synthesizing the hydroxylated analog of erythro-hydroxynonyladenine;
• and,
• d. purifying said hydroxylated analog of erythro-hydroxynonyladenine.