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Details for Patent: 5,616,714

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Details for Patent: 5,616,714

Title: Retroviral protease inhibiting compounds
Abstract:A retroviral protease inhibiting compound of the formula A--X--B is disclosed. Also disclosed are a composition and method for inhibiting a retroviral protease and for treating an HIV infection. Also disclosed are processes and intermediates useful for the preparation of the retroviral protease inhibitors.
Inventor(s): Kempf; Dale J. (Libertyville, IL), Norbeck; Daniel W. (Lindenhurst, IL), Codacovi; Lynn M. (Antioch, IL), Sham; Hing L. (Gurnee, IL), Wittenberger; Steven J. (Mundelein, IL)
Assignee: Abbott Laboratories (Abbott Park, IL)
Filing Date:Mar 24, 1995
Application Number:08/410,260
Claims:1. A compound of the formula: ##STR11## wherein R.sub.2 and R.sub.3 are independently selected from C.sub.3 -to-C.sub.7 -cycloalkyl-C.sub.1 -to-C.sub.6 -alkyl and (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl; and

(a) A is pyridyl-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- or (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- wherein R.sub.9 is -O-, -NH- or -N(C.sub.1 -to-C.sub.6 -loweralkyl)-, R.sub.5 is C.sub.1 -to-C.sub.6 -loweralkyl and substituted-pyridyl is a pyridyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy, halo-C.sub.1 -to-C.sub.6 -alkyl, unsubstituted -C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl,-COOH and -SO.sub.3 H and B is thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)-, thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-N(C.sub.1 -to-C.sub.6 -loweralkyl)-C(O)-, (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)- or (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-N(C.sub.1 -to-C.sub.6 -loweralkyl)-C(O)- wherein substituted-thiazolyl is a thiazolyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy, halo-C.sub.1 -to-C.sub.6 -alkyl, unsubstituted -C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl, -COOH and -SO.sub.3 H; or

(b) A is thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- or (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- wherein R.sub.9 is -O-, -NH- or -N (C.sub.1 -to-C.sub.6 -loweralkyl)-, R.sub.5 is C.sub.1 -to-C.sub.6 -loweralkyl and substituted-thiazolyl is a thiazolyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy, halo-C.sub.1 -to-C.sub.6 -alkyl, unsubstituted -C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl, -COOH and -SO.sub.3 H and B is pyridyl-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, pyridyl-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)-, pyridyl-C.sub.1 -to-C.sub.6 -alkyl-N(loweralkyl)-C(O)-, (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)- or (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-N(C.sub.1 -to-C.sub.6 -loweralkyl)-C(O)- wherein substituted-pyridyl is a pyridyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy, halo-C.sub.1 -to-C.sub.6 -alkyl, unsubstituted -C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl, -COOH and -SO.sub.3 H; or

(c) A is thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)-, thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-N(C.sub.1 -to-C.sub.6 -loweralkyl)-C(O)-, (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)- or (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-N(C.sub.1 -to-C.sub.6 -loweralkyl)-C(O)- wherein substituted-thiazolyl is a thiazolyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy, halo-C.sub.1 -to-C.sub.6 -alkyl, unsubstituted -C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl, -COOH and -SO.sub.3 H and B is pyridyl-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- or (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- wherein R.sub.9 is -O-, -NH- or -N(C.sub.1 -to-C.sub.6 -loweralkyl)-, R.sub.5 is C.sub.1 -to-C.sub.6 -loweralkyl and substituted-pyridyl is a pyridyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy, halo-C.sub.1 -to-C.sub.6 -alkyl, unsubstituted -C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl, -COOH and -SO.sub.3 H; or

(d) A is pyridyl-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, pyridyl-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)-, pyridyl-C.sub.1 -to-C.sub.6 -alkyl-N(C.sub.1 -to-C.sub.6 -loweralkyl)-C(O)-, (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)- or (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-N(C.sub.1 -to-C.sub.6 -loweralkyl)-C(O)- wherein substituted-pyridyl is a pyridyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy, halo-C.sub.1 -to-C.sub.6 -alkyl, unsubstituted -C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl, -COOH and -SO.sub.3 H and B is thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- or (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- wherein R.sub.9 is -O-, -NH- or -N(C.sub.1 -to-C.sub.6 -loweralkyl)-, R.sub.5 is -C.sub.1 -to-C.sub.6 -loweralkyl and substituted-thiazolyl is a thiazolyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy, halo-C.sub.1 -to-C.sub.6 -alkyl, unsubstituted -C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl, -COOH and -SO.sub.3 H; or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 wherein A is pyddyl-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- or (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- wherein R.sub.9 is -O-, -NH- or -N(C.sub.1 -to-C.sub.6 -loweralkyl)-, R.sub.5 is C.sub.1 -to-C.sub.6 -loweralkyl and substituted-pyridyl is a pyridyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy, halo -C.sub.1 -to-C.sub.6 -alkyl, unsubstituted -C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl, -COOH and -SO.sub.3 H and B is thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)-, thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-N(C.sub.1 -to-C.sub.6 -loweralkyl)-C(O)-, (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)- or (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-N(C.sub.1 -to-C.sub.6 -loweralkyl)-C(O)- wherein substituted-thiazolyl is a thiazolyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy, halo-C.sub.1 -to-C.sub.6 -alkyl, unsubstituted-C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl, -COOH and -SO.sub.3 H.

3. The compound of claim 2 wherein R.sub.2 and R.sub.3 are benzyl, A is pyridyl-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- wherein R.sub.9 is -O- or -N(CH.sub.3)- and R.sub.5 is isoproply or 2-butyl and B is thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-or (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)- wherein substituted-thiazolyl is a thiazolyl ring substituted with C.sub.1 -to-C.sub.6 -loweralkyl or amino.

4. The compound of claim 1 wherein A is thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- or (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- wherein R.sub.9 is -O-, -NH- or -N(C.sub.1 -to-C.sub.6 -loweralkyl)-, R.sub.5 is C.sub.1 -to-C.sub.6 -loweralkyl and substituted-thiazolyl is a thiazolyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy, halo-C.sub.1 -to-C.sub.6 -alkyl, unsubstituted-C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl, -COOH and -SO.sub.3 H and B is pyridyl-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, pyridyl-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)-, pyridyl-C.sub.1 -to-C.sub.6 -alkyl-N(loweralkyl)-C(O)-, (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)- or (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-N(C.sub.1 -to-C.sub.6 -loweralkyl)-C(O)- wherein substituted-pyridyl is a pyridyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy, halo-C.sub.1 -to-C.sub.6 -alkyl, unsubstituted -C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl, -COOH and -SO.sub.3 H.

5. The compound of claim 4 wherein R.sub.2 and R.sub.3 are benzyl, A is thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- or (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- wherein R.sub.9 is -O- or -N(CH.sub.3)-, R.sub.5 is isopropyl or 2-butyl and substituted-thiazolyl is a thiazolyl ring substituted with C.sub.1 -to-C.sub.6 -loweralkyl or amino and B is pyridyl-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-.

6. The compound of claim 1 wherein A is thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)-, thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-N(C.sub.1 -to-C.sub.6 -loweralkyl)-C(O)-, (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)- or (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-N(C.sub.1 -to-C.sub.6 -loweralkyl)-C(O)- wherein substituted-thiazolyl is a thiazolyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy, halo-C.sub.1 -to-C.sub.6 -alkyl, unsubstituted -C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl, -COOH and -SO.sub.3 H and B is pyridyl-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- or (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- wherein R.sub.9 is -O-, -NH- or -N(C.sub.1 -to-C.sub.6 -loweralkyl)-, R.sub.5 is C.sub.1 -to-C.sub.6 -loweralkyl and substituted-pyridyl is a pyridyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy, halo-C.sub.1 -to-C.sub.6 -alkyl, unsubstituted -C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl, -COOH and -SO.sub.3 H.

7. The compound of claim 6 wherein R.sub.2 and R.sub.3 are benzyl, A is thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)- or (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)- wherein substituted-thiazolyl is a thiazolyl ring substituted with C.sub.1 -to-C.sub.6 -loweralkyl or amino and B is pyridyl-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- wherein R.sub.9 is -O- or -N(CH.sub.3)- and R.sub.5 is isopropyl or 2-butyl.

8. The compound of claim 1 wherein A is pyridyl-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, pyridyl-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)-pyridyl-C.sub.1 -to-C.sub.6 -alkyl-N(C.sub.1 -to-C.sub.6 -loweralkyl)-C(O)-, (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)-, (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-NH-C(O)- or (substituted-pyridyl)-C.sub.1 -to-C.sub.6 -alkyl-N(C.sub.1 -to-C.sub.6 -loweralkyl)-C(O)- wherein substituted-pyridyl is a pyridyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy-halo-C.sub.1 -to-C.sub.6 -alkyl, unsubstituted -C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl, -COOH and -SO.sub.3 H and B is thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- or (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- wherein R.sub.9 is -O-, -NH- or -N(C.sub.1 -to-C.sub.6 -loweralkyl)-, R.sub.5 is -C.sub.1 -to-C.sub.6 -loweralkyl and substituted-thiazolyl is a thiazolyl ring substituted with one or two substituents independently selected from C.sub.1 -to-C.sub.6 -loweralkyl, hydroxy, halo, amino, C.sub.1 -to-C.sub.6 -alkylamino, di-C.sub.1 -to-C.sub.6 -alkylamino, C.sub.1 -to-C.sub.6 -alkoxy-halo-C.sub.1 -to-C.sub.6 -alkyl, unsubstituted -C.sub.3 -to-C.sub.7 -cycloalkyl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl, unsubstituted (C.sub.6 -monocyclic or C.sub.9 - or C.sub.10 -bicyclic)aryl-C.sub.1 -to-C.sub.6 -alkyl, -COOH and -SO.sub.3 H.

9. The compound of claim 8 wherein R.sub.2 and R.sub.3 are benzyl, A is pyridyl-C.sub.1 -to-C.sub.6 -alkyl-O-C(O)- and B is thiazolyl-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- or (substituted-thiazolyl)-C.sub.1 -to-C.sub.6 -alkyl-R.sub.9 -C(O)-NH-CH(R.sub.5)-C(O)- wherein R.sub.9 is -O- or -N(CH.sub.3)-, R.sub.5 is isopropyl or 2-butyl and substituted-thiazolyl is a thiazolyl ring substituted with C.sub.1 -to-C.sub.6 -loweralkyl or amino.

10. A compound selected from the group consisting of

(2S,3S,5S)-2-(N-(N-((N-Methy-N-((2-thiazolyl)-methyl)amino)carbonyl)valinyl )amino)-5-(N-((3-pyridinyl)-methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhe xane;

(2S,3S,5S)-2-(N-(N-((N-Methyl-N-((4-thiazolyl)-methyl)amino)carbonyl)valiny l)amino)-5-(N-((3-pyridinyl)-methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyh exane;

(2S,3S,5S)-5-(N-(N-((N-Methyl-N-((4-thiazolyl)-methyl)amino)carbonyl)valiny l)amino)-2-(N-((3-pyridinyl)-methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyh exane;

(2S,3S,5S)-5-(N-(N-((2-Thiazolyl)methoxycarbonyl)-valinyl)amino)-2-(N-((3-p yridinyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane;

(2S,3S,5S)-2-(N-(N-((2-Thiazolyl)methoxycarbonyl)-valinyl)amino)-5-(N-((3-p yridinyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane;

(2S,3S,5S)-2-(N-(N-((N-Methyl-N-((2-methyl-4-thiazolyl)methyl)amino)carbony l)valinyl)amino)-5-(N-((3-pyridinyl)methoxycarbonyl)amino)-1,6-diphenyl-3-h ydroxyhexane;

(2S,3S,5S)-2-(N-(N-((N-Methyl-N-((2-amino-4-thiazolyl)methyl)amino)carbonyl )valinyl)amino)-5-(N-((3-pyridinyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hy droxyhexane;

(2S,3S,5S)-5-(N-(N-((N-Methyl-N-((2-amino-4-thiazolyl)methyl)amino)carbonyl )valinyl)amino)-2-(N-((3-pyridinyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hy droxyhexane;

(2S,3S,5S)-5-(N-(N-((N-Methyl-N-((2-methyl-4-thiazolyl)methyl)amino)carbony l)valinyl)amino)-2-(N-((3-pyridinyl)methoxycarbonyl)amino)-1,6-diphenyl-3-h ydroxyhexane;

(2S,3S,5S)-2-(N-(N-((2-Pyridinyl)methoxycarbonyl)-valinyl)amino)-5-(N-((5-t hiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane;

(2S,3S,5S)-5-(N-(N-((2-Pyridinyl)methoxycarbonyl)-valinyl)amino)-2-(N-((5-t hiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane;

(2S,3S,5S)-2-(N-(N-((N-Methyl-N-((2-pyridinyl)methyl)-amino)carbonyl)isoleu cinyl)amino)-5-(N-((5-thiazolyl)-methoxycarbonyl)amino)-1,6-diphenyl-3-hydr oxyhexane; and

(2S,3S,5S)-5-(N-(N-((N-Methyl-N-((2-pyridinyl)methyl)-amino)carbonyl)isoleu cinyl)amino)-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-1,6-diphenyl-3-hydr oxyhexane;

or a pharmaceutically acceptable salt thereof.
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