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Claims for Patent: 5,648,497

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Claims for Patent: 5,648,497

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 Laboraotries (Abbott Park, IL)
Application Number:08/410,623
Patent Claims: 1. A compound of the formula: ##STR17## 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 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)- and R.sub.5 is C.sub.1 -to-C.sub.6 -loweralkyl 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)-- and wherein at each occurrence substituted-thiazolyl is independently selected from 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-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)-- 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)- and R.sub.5 is C.sub.1 -to-C.sub.6 -loweralkyl and wherein at each occurrence substituted-thiazolyl is independently selected from 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 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)- and R.sub.5 is C.sub.1 -to-C.sub.6 -loweralkyl 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)-- and wherein at each occurrence substituted-thiazolyl is independently selected from 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 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 --O(O)--NH--CH(R.sub.5)--C(O)-- wherein R.sub.9 is --O-- or --N(CH.sub.3)-- and R.sub.5 is C.sub.1 -to-C.sub.6 -loweralkyl 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)-- and wherein at each occurrence substituted-thiazolyl is as defined therein.

4. The compound of claim 3 wherein R.sub.5 is isopropyl and at each occurrence substituted-thiazolyl is independently amino-substituted thiazolyl or C.sub.1 -to-C.sub.6 -loweralkyl-substituted thiazolyl.

5. 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)-- 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)- and R.sub.5 is C.sub.1 -to-C.sub.6 -loweralkyl and wherein at each occurrence substituted-thiazolyl is independently selected from 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.

6. The compound of claim 5 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)-- 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)-- and R.sub.5 is C.sub.1 -to-C.sub.6 -loweralkyl and wherein at each occurrence substituted-thiazolyl is as defined therein.

7. The compound of claim 6 wherein R.sub.5 is isopropyl and at each occurrence substituted-thiazolyl is independently amino-substituted thiazolyl or C.sub.1 -to-C.sub.6 -loweralkyl-substituted thiazolyl.

8. The compound (2S,3S,5S)-2-(N-(N-((N-Methyl-N-((2-amino-4-thiazolyl)methyl)amino)carbony l)valinyl)amino)-5-(N-((5-thiazolyl)-methoxycarbonyl)amino)-1,6-diphenyl-3- hydroxyhexane; or a pharmaceutically acceptable salt thereof.
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