C-3 substituted bicyclooctane based HIV protease inhibitors

A compound having the formula

• or a pharmaceutically acceptable salt, isomer, mixture of isomers, crystalline form, non crystalline form, hydrate, or solvate thereof;
• wherein
• X1 is C(O), S(O), S(O)2, HNS(O)2, HNC(O), or C(O)NH;
• R1 and R2 are in each instance independently selected from the group consisting of hydrogen, and a prodrug forming group;
• RA represents from 0 to 4 substituents independently selected in each instance from the group consisting of hydroxy, alkyl, heteroalkyl, alkyloxy, heteroalkyloxy, cycloalkyl, cycloheteroalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, each of which is optionally substituted;
• or RA represents from 2 to 4 substituents where two of the substituents are vicinal substituents and taken with the attached carbons form a carbocycle or heterocycle;
• and the remaining substituents, if present, are independently selected in each instance from the group consisting of alkyl, heteroalkyl, alkyloxy, heteroalkyloxy, cycloalkyl, cycloheteroalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, each of which is optionally substituted;
• RB represents from 0 to 4 substituents independently selected in each instance from the group consisting of amino, alkyl, heteroalkyl, alkyloxy, heteroalkyloxy, cycloalkyl, cycloheteroalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, each of which is optionally substituted;
• or RB represents from 2 to 4 substituents where two of the substituents are vicinal substituents and taken with the attached carbons form a carbocycle or heterocycle;
• and the remaining substituents, if present, are independently selected in each instance from the group consisting of alkyl, heteroalkyl, alkyloxy, heteroalkyloxy, cycloalkyl, cycloheteroalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, each of which is optionally substituted;
• R3 is alkyl, cycloalkyl, arylalkyl, or heteroarylalkyl, each of which is optionally substituted;
• R4 and R5 are independently selected in each instance from hydrogen, halogen, oxo, hydroxy, or the group consisting of alkyl, heteroalkyl, alkyloxy, hydroxyalkyl, acyloxy, —OC(C))-amino, acyl, amino, sulfonylamino, acylamino, alkyloxy-C(O)-amino, and alkoxyamino, each of which is optionally substituted, where at least one of R4 or R5 is not hydrogen.