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Details for Patent: 6,172,082

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Details for Patent: 6,172,082

Title: .alpha.- and .beta.-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
Abstract:.alpha.- and .beta.-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.
Inventor(s): Vazquez; Michael L. (Gurnee, IL), Mueller; Richard A. (Glencoe, IL), Talley; John J. (St. Louis, MO), Getman; Daniel (Chesterfield, MO), DeCrescenzo; Gary A. (St. Peters, MO), Freskos; John N. (Clayton, MO)
Assignee: G. D. Searle & Co. (Chicago, IL)
Filing Date:Jun 07, 1995
Application Number:08/476,788
Claims:1. Compound represented by the formula: ##STR365##

wherein:

R represents 2-quinolinylcarbonyl;

R.sup.1 represents hydrogen and radicals as defined for R.sup.3 or R and R' together with the nitrogen to which they are attached represent heterocycloalkyl and heteroaryl radical;

R.sup.1 represents hydrogen, --CH.sub.2 SO.sub.2 NH.sub.2, --CH.sub.2 CO.sub.2 CH.sub.3, --CO.sub.2 CH.sub.3, --CONH.sub.2, --CH.sub.2 C(O)NHCH.sub.3, --C(CH.sub.3).sub.2 (SH), --C(CH.sub.3).sub.2 (SCH.sub.3), --C(CH.sub.3).sub.2 (S[O]CH.sub.3), --C(CH.sub.3).sub.2 (S[O].sub.2 CH.sub.3), alkyl, haloalkyl, alkenyl, alkynyl and cycloalkyl radicals, and amino acid side chains selected from asparagine, S-methyl cysteine and the sulfoxide (SO) and sulfone (SO.sub.2) derivatives thereof, isoleucine, allo-isoleucine, alanine, leucine, tert-leucine, phenylalanine, ornithine, histidine, norleucine, glutamine, threonine, glycine, allo-threonine, serine, O-methyl serine, asparatic acid, beta-cyano alanine and valine side chains;

R.sup.2 represents alkyl, aryl, cycloalkyl, cycloalkylalkyl and aralkyl radicals, which radicals are optionally substituted with a group selected from alkyl and halogen radials, --NO.sub.2, --C=N, CF.sub.3, --OR.sup.9, --SR.sup.9, wherein R.sup.9 represents hydrogen and alkyl radicals, and halogen radicals;

R.sup.3 represents alkyl, haloalkyl, alkenyl, alkynyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heteroaryl, heterocycloalkylalkyl, aryl, aralkyl, heteroaralkyl, aminoalkyl and mono- and disubstituted aminoalkyl radicals, wherein said substituents are selected from alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, heteroaralkyl, heterocycloalkyl, and heterocycloalkylalkyl radicals, or in the case of a disubstituted aminoalkyl radical, said substituents along with the nitrogen atom to which they are attached, form a heterocycloalkyl or a heteroaryl radical;

R.sup.4 represents radicals as defined by R.sup.3.

2. Compound of claim 1 wherein R.sup.1 represents alkyl, alkynyl and alkenyl radicals, and amino acid side chains selected from the group consisting of asparagine, valine, threonine, allo-threonine, isoleucine, S-methyl cysteine and the sulfone and sulfoxide derivatives thereof, alanine, and allo-isoleucine.

3. Compound of claim 1 wherein R.sup.1 represents methyl, propargyl, t-butyl, isopropyl and sec-butyl radicals, and amino acid side chains selected from the group consisting of asparagine, valine, S-methyl cysteine, allo-iso-leucine, iso-leucine, threonine, serine, aspartic acid, beta-cyano alanine, and allo-threonine side chains.

4. Compound of claim 1 wherein R.sup.1 represents propargyl and t-butyl radicals.

5. Compound of claim 1 wherein R.sup.1 represents a t-butyl radical.

6. Compound of claim 1 wherein R.sup.1 represents amino acid side chains selected from asparagine, valine, alanine and isoleucine side chains.

7. Compound of claim 1 wherein R.sup.1 represents amino acid side chains selected from asparagine, iso-leucine and valine side chains.

8. Compound of claim 1 wherein R.sup.1 represents an asparagine side chain.

9. Compound of claim 1 wherein R.sup.1 represents a t-butyl radical and an asparagine side chain.

10. Compound of claim 1 wherein R.sup.1 represents a propargyl radical.

11. Compound of claim 1 wherein R.sup.1 represents an isoleucine side chain.

12. Compound of claim 1 wherein R.sup.1 represents a valine side chain.

13. Compound of claim 1 wherein R.sup.2 represents alkyl, cycloalkylalkyl and aralkyl radicals, which radicals are optionally substituted with halogen radicals and radicals represented by the formula --OR.sup.9 and --SR.sup.9 wherein R.sup.9 represents hydrogen and alkyl radicals.

14. Compound of claim 1 wherein R.sup.2 represents alkyl, cycloalkylalkyl and aralkyl radicals.

15. Compound of claim 1 wherein R.sup.2 represents aralkyl radicals.

16. Compound of claim 1 wherein R.sup.2 represents CH.sub.3 SCH.sub.2 CH.sub.2 --, iso-butyl, n-butyl, benzyl, 4-fluorobenzyl, 2-naphthylmethyl and cyclohexylmethyl radicals.

17. Compound of claim 1 wherein R.sup.2 represents an n-butyl and iso-butyl radicals.

18. Compound of claim 1 wherein R.sup.2 represents benzyl, 4-fluorobenzyl and 2-naphthylmethyl radicals.

19. Compound of claim 1 wherein R.sup.2 represents a cyclohexylmethyl radical.

20. Compound of claim 1 wherein R.sup.3 and R.sup.4 independently represent alkyl, haloalkyl, alkenyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, aralkyl and heteroaralkyl radicals.

21. Compound of claim 20 wherein R.sup.4 represents phenyl.

22. Compound of claim 20 wherein R.sup.3 and R.sup.4 independently represent alkyl and alkenyl radicals.

23. Compound of claim 20 wherein R.sup.3 and R.sup.4 independently represent alkyl, alkenyl, haloalkyl, alkoxyalkyl and hydroxyalkyl radicals.

24. Compound of claim 20 wherein R.sup.3 and R.sup.4 independently represent alkyl, cycloalkyl and cycloalkylalkyl radicals.

25. Compound of claim 20 wherein R.sup.3 and R.sup.4 independently represent alkyl, heterocycloalkyl and heterocycloalkylalkyl radicals.

26. Compound of claim 20 wherein R.sup.3 and R.sup.4 independently represent alkyl, aryl and aralkyl radicals.

27. Compound of claim 20 wherein R.sup.4 represents phenyl and substituted phenyl radicals.

28. Compound of claim 1 wherein R.sup.3 represents alkyl radicals having from about 2 to about 5 carbon atoms.

29. Compound of claim 1 wherein R.sup.3 represents n-pentyl, n-hexyl, n-propyl, i-butyl, cyclohexyl, neo-pentyl, i-amyl, and n-butyl radicals.

30. Compound of claim 1 wherein R.sup.3 and R.sup.4 independently represent alkyl radicals having from about 2 to about 5 carbon atoms, cycloalkylalkyl radicals, aralkyl radicals, heterocycloalkylalkyl radicals or heteroaralkyl radicals.

31. Compound of claim 1 wherein R.sup.3 represents isobutyl, n-propyl, n-butyl, isoamyl, cyclohexyl, cyclohexylmethyl radicals and R.sup.4 represents phenyl and substituted phenyl radicals.

32. Compound of claim 1 wherein R.sup.3 is cyclohexylmethyl and R.sup.4 is phenyl and substituted phenyl radicals.

33. Compound of claim 1 wherein R.sup.3 is i-amyl or i-butyl and R.sup.4 is phenyl or substituted phenyl selected from para-chlorophenyl, para-fluorophenyl, para-nitrophenyl, para-aminophenyl, and para-methoxyphenyl.

34. Compound of claim 1 wherein R.sup.3 is i-butyl and R.sup.4 is phenyl.

35. Compound of claim 1 wherein R.sup.3 is n-butyl and R.sup.4 is phenyl.

36. Compound of claim 1 wherein R.sup.3 is cyclohexyl and R.sup.4 is phenyl or substituted phenyl selected from para-chlorophenyl, para-fluorophenyl, para-nitrophenyl, para-aminophenyl, and para-methoxyphenol.

37. Compound of claim 1 wherein R.sup.4 represents alkyl and cycloalkyl radicals.

38. Compound of claim 1 wherein R.sup.4 represents aryl radicals.

39. Compound of claim 1 wherein R.sup.4 represents heteroaryl radicals.

40. Compound of claim 1 wherein R.sup.3 represents heteroaralkyl radicals and R.sup.4 is phenyl or substituted phenyl selected from para-chlorophenyl, para-fluorophenyl, para-nitrophenyl, para-aminophenyl, and para-methoxyphenyl.

41. Compound of claim 1 wherein R.sup.3 is a p-fluorobenzyl radical and R.sup.4 is a phenyl radical or substituted phenyl selected from para-chlorophenyl, para-fluorophenyl, para-nitrophenyl, para-aminophenyl, and para-methoxyphenyl.

42. Compound of claim 1 wherein R.sup.3 is a 4-pyridylmethyl radical or its N-oxide and R.sup.4 is a phenyl radical or substituted phenyl selected from para-chlorophenyl, para-fluorophenyl, para-nitrophenyl, para-aminophenyl, and para-methoxyphenyl.

43. Compound of claim 1 wherein R.sup.4 represents an alkyl radical having from 1 to about 6 carbon atoms.

44. Compound of claim 1 wherein R.sup.4 represents a 5 or 6-membered heterocyclyl radical, optionally substituted with an alkyl radical having from 1 to about 3 carbon atoms.

45. Compound of claim 1 where R.sup.1 represents the amino acid side chain of asparagine.

46. A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier.

47. Method of treating a retroviral infection comprising administering an effective amount of a composition of claim 46.

48. Method of claim 47 wherein the retroviral infection is an HIV infection.

49. Method for treating AIDS comprising administering an effective amount of a composition of claim 46.
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