HIV protease inhibitors

A composition useful for inhibiting HIV protease which comprises

• (1) a compound having the formula II ##STR285## wherein:
• f is 0, 1, or 2;
• A' and B' are individually selected from carbocyclic or heterocyclic, aromatic, saturated or partially saturated 5, 6 or 7 member rings which can be further substituted;
• n' is 0, 1 or 2;
• X' and Z' are individually selected from oxygen and sulphur;
• when f is 2, Y' is a substituted or unsubstituted amino group, oxygen, sulphur, or --CH.sub.2 --;
• when f is 1, Y' is --CH.dbd.;
• when f is 0, Y' is --C.tbd.;
• R'.sub.1, R'.sub.2, R'.sub.3 and R'.sub.4 are individually selected from hydrogen, alkyl, cycloalkyl, aryl, substituted alkyl, cycloalkyl or aryl, substituted oxygen, hydroxyl, substituted or unsubstituted non-cyclic amino and substituted or unsubstituted non-aryl heterocycle, wherein R'.sub.1 and R'.sub.2 or R'.sub.3 and R'.sub.4 can form a ring with the nitrogen atom to which they are attached;
• R.sub.17 and R.sub.18 are individually selected from hydrogen, halogen, hydroxyl, substituted or unsubstituted alkoxy, mercapto, thioether, --NR'.sub.1 R'.sub.2, nitro, alkyl, aryl and substituted alkyl or aryl, wherein R.sub.17 can form a fused ring structure with A' and R.sub.18 can form a fused ring structure with B';
• and
• R.sub.19 is hydrogen or a 1 to 3 carbon substituted or unsubstituted alkyl group;
• or a pharmaceutically acceptable salt thereof;
• and
• (2) a pharmaceutically acceptable carrier.

A process for inhibiting the action of the HIV virus which process comprises administering to a host in recognized need of such treatment an effective amount of a compound of the formula II ##STR286## wherein:

• f is 0, 1, or 2;
• A' and B' are individually selected from carbocyclic or heterocyclic, aromatic, saturated or partially saturated 5, 6 or 7 member rings which can be further substituted;
• n' is 0, 1 or 2;
• X' and Z' are individually selected from oxygen and sulphur;
• when f is 2, Y' is a substituted or unsubstituted amino group, oxygen, sulphur, or --CH.sub.2 --;
• when f is 1, Y' is --CH.dbd.;
• when f is 0, Y' is --C.tbd.;
• R'.sub.1, R'.sub.2, R'.sub.3 and R'.sub.4 are individually selected from hydrogen, alkyl, cycloalkyl, aryl, substituted alkyl, cycloalkyl or aryl, substituted oxygen, hydroxyl, substituted or unsubstituted non-cyclic amino and substituted or unsubstituted non-aryl heterocycle, wherein R'.sub.1 and R'.sub.2 or R'.sub.3 and R'.sub.4 can form a ring with the nitrogen atom to which they are attached;
• R.sub.17 and R.sub.18 are individually selected from hydrogen, halogen, hydroxyl, substituted or unsubstituted alkoxy, mercapto, thioether, --NR'.sub.1 R'.sub.2, nitro, alkyl, aryl and substituted alkyl or aryl, wherein R.sub.17 can form a fused ring structure with A' and R.sub.18 can form a fused ring structure with B';
• and
• R.sub.19 is hydrogen or a 1 to 3 carbon substituted or unsubstituted alkyl group;
• or a pharmaceutically acceptable salt thereof.

A method for preparing a compound of the formula XVI ##STR287## wherein:

• A' and B' are individually selected from carbocyclic or heterocyclic, aromatic, saturated or partially saturated 5, 6 or 7 member rings which can be further substituted;
• R'.sub.1, R'.sub.2, R'.sub.3 and R'.sub.4 are individually selected from hydrogen, alkyl, cycloalkyl, aryl, substituted alkyl, cycloalkyl or aryl, substituted oxygen, hydroxyl, substituted or unsubstituted non-cyclic amino and substituted or unsubstituted non-aryl heterocycle, wherein R'.sub.1 and R'.sub.2 or R'.sub.3 and R'.sub.4 can form a ring with the nitrogen atom to which they are attached;
• R.sub.17 and R.sub.18 are individually selected from hydrogen, halogen, hydroxyl, substituted or unsubstituted alkoxy, mercapto, thioether, --NR'.sub.1 R'.sub.2, nitro, alkyl, aryl and substituted alkyl or aryl, wherein R.sub.17 can form a fused ring structure with A' and R.sub.18 can form a fused ring structure with B';
• which method comprises carrying out the following reactions:
• ##STR288## wherein:
• a) the compound of the formula XIII, wherein R.sub.24 and R'.sub.24 are individually selected from alkyl groups, is reacted with a compound of the formula XIV under conditions sufficient to form a compound of the formula XV;
• and
• b) the compound of the formula XV is sequentially reduced, followed by reaction of the reduced compound with at least one amine selected from R'.sub.1 R'.sub.2 NH and R'.sub.3 R'.sub.4 NH under conditions sufficient to form a compound of the formula XVI.