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Claims for Patent: 5,914,332

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Claims for Patent: 5,914,332

Title: Retroviral protease inhibiting compounds
Abstract:A compound of the formula: ##STR1## is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.
Inventor(s): Sham; Hing Leung (Mundelein, IL), Norbeck; Daniel W. (Crystal Lake, IL), Chen; Xiaoqi (Libertyville, IL), Betebenner; David A. (Gurnee, IL)
Assignee: Abbott Laboratories (Abbott Park, IL)
Application Number:08/753,201
Patent Claims: 1. A compound of the formula: ##STR84## wherein R.sub.1 and R.sub.2 are independently selected from the group consisting of loweralkyl, cycloalkylalkyl and arylalkyl;

R.sub.3 is loweralkyl, hydroxyalkyl or cycloalkylalkyl;

R.sub.4 is aryl;

R.sub.5 is ##STR85## wherein n is 1, 2 or 3, X is O, S or NH and Y is --O-- or --N(R.sub.6)-- wherein R.sub.6 is hydrogen, loweralkyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl;

and

L.sub.1 is

a) --O--,

b) --S--,

c) --N(R.sub.7)-- wherein R.sub.7 is hydrogen, loweralkyl, cycloalkyl or cycloalkylalkyl,

d) --O-alkylenyl-,

e) --S-alkylenyl-

f) --S(O)-alkylenyl-,

g) --S(O).sub.2 -alkylenyl-,

h) --N(R.sub.7)-alkylenyl- wherein R.sub.7 is defined as above,

i) -alkylenyl-O--,

j) -alkylenyl-S--,

k) alkylenyl-N(R.sub.7)-- wherein R.sub.7 is defined as above,

l) alkylenyl or

m) alkenylenyl;

or a pharmaceutically acceptable salt, ester or prodrug thereof.

2. A compound according to claim 1 wherein R.sub.1 and R.sub.2 are arylalkyl, R.sub.3 is loweralkyl, R.sub.4 is aryl, R.sub.5 is ##STR86## wherein X, Y and n are defined as therein and L.sub.1 is --O-alkylenyl.

3. A compound according to claim 1 wherein R.sub.1 and R.sub.2 are benzyl or R.sub.1 is benzyl and R.sub.2 is loweralkyl, R.sub.3 is loweralkyl, R.sub.4 is phenyl which is substituted with two loweralkyl groups and which is optionally substituted with a third substituent selected from the group consisting of loweralkyl, hydroxy, amino and halo, R.sub.5 is ##STR87## wherein n is 1 or 2, X is O or S and Y is --NH--, and

L.sub.1 is --O--CH.sub.2 --.

4. A compound according to claim 1 wherein R.sub.1 and R.sub.2 are benzyl or R.sub.1 is benzyl and R.sub.2 is isopropyl, R.sub.3 is loweralkyl, R.sub.4 is 2,6-dimethylphenyl which is optionally substituted with a third substituent selected from the group consisting of loweralkyl and halo, R.sub.5 is ##STR88## wherein n is 1 or 2, X is O or S and Y is --NH--, and

L.sub.1 is --O--CH.sub.2 --.

5. A compound according to claim 1 wherein R.sub.1 and R.sub.2 are benzyl or R.sub.1 is benzyl and R.sub.2 is isopropyl, R.sub.3 is loweralkyl, R.sub.4 is 2,6-dimethylphenyl which is optionally substituted with a third substituent selected from the group consisting of loweralkyl and halo, R.sub.5 is ##STR89## wherein n is 1 or 2, X is O or S and Y is --NH-- and L.sub.1 is --O--CH.sub.2 --.

6. A compound selected from the group consisting of:

(2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-[2S-(1-tetrahydro -pyrimid-2-onyl)-3-methyl butanoyl]amino-1,6-diphenylhexane;

(2S,3S,5S)-2-(2,6-Dimethylphenoxyacetyl)amino-3-hydroxy-5-(2S-(1-imidazolid in-2-onyl)-3,3dimethyl butanoyl)amino-1,6-diphenylhexane;

(2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(2S-(1-imidazolid in-2-thionyl)-3-methyl butanoyl)amino-1,6-diphenylhexane;

(2S,3S,5S)-2-(2,4,6-trimethylphenoxyacetyl)amino-3-hydroxy-5-(2S-(1-imidazo lidin-2-onyl-3-methylbutanoyl)amino-1,6-diphenylhexane;

(2S,3S,5S)-2-(4-fluoro-2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(2S-(1-i mmidazolidin-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane;

(2S,3S,5S)-2-(trans-3-(2,6-dimethylphenyl)propenoyl)amino-3-hydroxy-5-(2S-1 -tetrahydropyrimidin-2-onyl)-3-methyl-butanoyl)amino-1,6-diphenylhexane;

(2S,3S,5S)-2-(3-(2,6-dimethylphenyl)propanoyl)amino-3-hydroxy-5-(2S-(1-tetr ahydropyrimidin-2-onyl)-3-methyl-butanoyl)amino-1,6-diphenylhexane;

(2S,3S,5S)-2-(2,6-Dimethylphenoxyacetyl)amino-3-hydroxy-5-(2S-(1-tetrahydro -pyrimid-2-onyl)-3-methylbutanoyl)amino-1-phenyl-6-methylheptane;

or a pharmaceutically acceptable salt, ester or prodrug thereof.

7. The compound (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(2S-(1-tetrahydr o-pyrimid-2-onyl)-3-methyl butanoyl)amino-1,6-diphenylhexane;

or a pharmaceutically acceptable salt, ester or pyodrug thereof.

8. The compound (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(2-(1-tetrahydro -pyrimid-2-onyl)-3-methyl butanoyl)amino-1,6-diphenylhexane;

or a pharmaceutically acceptable salt thereof.

9. A pharmaceutical composition for inhibiting HIV protease comprising a pharmaceutical carrier and a therapeutically effective amount of the compound of claim 1.

10. A pharmaceutical composition for inhibiting HIV protease comprising a pharmaceutical carrier and a therapeutically effective amount of the compound of claim 7.

11. A pharmaceutical composition for inhibiting HIV protease comprising a pharmaceutical carrier and a therapeutically effective amount of the compound of claim 8.

12. A method for inhibiting HIV protease comprising administering to a human in need of such treatment a therapeuctially effective amount of the compound of claim 1.

13. A method for inhibiting HIV protease comprising administering to a human in need of such treatment a therapeuctially effective amount of the compound of claim 7.

14. A method for inhibiting an HIV infection comprising administering to a human in need of such treatment a therapeuctially effective amount of the compound of claim 1.

15. A method for inhibiting an HIV infection comprising administering to a human in need of such treatment a therapeuctially effective amount of the compound of claim 7.

16. A method for inhibiting HIV protease comprising administering to a human in need of such treatment a therapeuctially effective amount of the compound of claim 8.

17. A method for inhibiting an HIV infection comprising administering to a human in need of such treatment a therapeuctially effective amount of the compound of claim 8.
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