Cycloalkyl-dione derivatives and methods of their use
The present invention is directed to compounds of formula I: wherein A is n is 0, 1, or 2; m is 0 or 1; R 1 is H or C 1-6 alkyl and R 2 is H, C 1-6 alkyl, C 1-6 alkaryl, aryl, or heteroaryl; and X is O or NH. Tautomers, enantiomers, and diastereomers, as well as pharmaceutically acceptable salt forms, of compounds of formula I are also within the scope of the invention. Methods of preparing and using the compounds of formula I are also described. wherein A is
1.
wherein
A is
n is 0, 1, or 2;
m is 0 or 1;
R 1 is H or C 1-6 alkyl;
R 2 is H, C 1-6 alkyl, C 1-6 alkaryl, aryl, or heteroaryl; and
X is O or NH;
or a tautomer, enantiomer, or diastereomer thereof;
or a pharmaceutically acceptable salt form thereof.
2. The compound of claim 1 , wherein A is
3. The compound of claim 1 , wherein m is 0.
4. The compound of claim 1 , wherein X is O.
5. The compound of claim 1 , wherein n is 1.
6. The compound of claim 1 , wherein R 1 is H.
7. The compound of claim 1 , wherein R 2 is C 1-6 alkyl.
8. The compound of claim 7 , wherein R 2 is methyl, ethyl, propyl, isopropyl, —CH 2 -cyclopropyl, —CH 2 -isopropyl, or cyclohexyl.
9. The compound of claim 7 , wherein R 2 is methyl.
10. The compound of claim 1 , wherein R 2 is substituted or unsubstituted aryl.
11. The compound of claim 10 , wherein R 2 is substituted or unsubstituted phenyl.
12. The compound of claim 11 , wherein R 2 is substituted phenyl.
13. The compound of claim 12 , wherein R 2 is F-phenyl or methoxyphenyl.
14. The compound of claim 12 , wherein R 2 is disubstituted phenyl.
15. The compound of claim 14 , wherein R 2 is diC 1-6 alkyl-substituted phenyl.
16. The compound of claim 15 , wherein R 2 is dimethylphenyl.
17. The compound of claim 1 , wherein the compound is of formula IA
18. The compound of claim 17 , wherein R 1 is H.
19. The compound of claim 17 , wherein R 1 is C 1-6 alkyl.
20. The compound of claim 17 , wherein X is O; R 1 is H; and R 2 is C 1-6 alkyl.
21. The compound of claim 20 , wherein R 2 is methyl, ethyl, propyl, isopropyl, —CH 2 -isopropyl, or —CH 2 -cyclopropyl.
22. The compound of claim 17 , wherein X is O; R 1 is H; and R 2 is benzyl.
23. The compound of claim 17 , wherein X is O; R 1 is H; and R 2 substituted or unsubstituted phenyl.
24. The compound of claim 23 , wherein R 2 is substituted phenyl.
25. The compound of claim 24 , wherein R 2 is F-phenyl or methoxyphenyl.
26. The compound of claim 24 , wherein R 2 is disubstituted phenyl.
27. The compound of claim 26 , wherein R 2 is diC 1-6 alkyl-substituted phenyl.
28. The compound of claim 27 , wherein R 2 is dimethylphenyl.
29. A pharmaceutical formulation comprising a compound according to claim 1 and a pharmaceutically acceptable carrier or diluent.
30. A method of treating thrombus, Alzheimer's disease, diabetic nephropathy, bronchial asthma, or allergic rhinitis in a patient comprising administering to the patient a compound according to claim 1 .