Antioxidant inflammation modulators: oleanolic acid derivatives with saturation in the C-ring

1. A pharmaceutical composition comprising a compound of the formula:

wherein:

Y is cyano, heteroaryl (C≦12) , substituted heteroaryl (C≦12) , or —C(O)R a , further wherein:

R a is:

hydrogen, hydroxy, halo, amino, azido, mercapto or silyl; or

alkyl (C≦12) , alkenyl (C≦12) , alkynyl (C≦12) , aryl (C≦12) , aralkyl (C≦12) , heteroaryl (C≦12) , heteroaralkyl (C≦12) , alkoxy (C≦12) , alkenyloxy (C≦12) , alkynyloxy (C≦12) , aryloxy (C≦12) , aralkoxy (C≦12) , heteroaryloxy (C≦12) , heteroaralkoxy (C≦12) , acyloxy (C≦12) , alkylamino (C≦12) , alkoxyamino (C≦12) , dialkylamino (C≦12) , alkenylamino (C≦12) , alkynylamino (C≦12) , arylamino (C≦12) , aralkylamino (C≦12) , heteroarylamino (C≦12) , heteroaralkylamino (C≦12) , amido (C≦12) , or a substituted version of any of these groups; and

X is OR b , or NR b R c , wherein R b and R c are each independently:

hydrogen or hydroxy;

alkyl (C≦8) , aryl (C≦8) , aralkyl (C≦8) , acyl (C≦8) , alkoxy (C≦8) , aryloxy (C≦8) , acyloxy (C≦8) , alkylamino (C≦8) , arylamino (C≦8) , amido (C≦8) , or a substituted version of any of these groups; or

provided that R b is absent when the atom to which it is bound is part of a double bond, further provided that when R b is absent the atom to which it is bound is part of a double bond;

or a pharmaceutically acceptable salt, tautomer, or optical isomer thereof; and

a pharmaceutically acceptable carrier.

2. The pharmaceutical composition of claim 1 , wherein the compound is further defined as:

wherein R a is:

hydrogen, hydroxy, halo or amino; or

alkyl (C≦8) , alkenyl (C≦8) , alkynyl (C≦8) , aryl (C≦8) , aralkyl (C≦8) , heteroaryl (C≦8) , heteroaralkyl (C≦8) , alkoxy (C≦8) , alkenyloxy (C≦8) , alkynyloxy (C≦8) , aryloxy (C≦8) , aralkoxy (C≦8) , heteroaryloxy (C≦8) , heteroaralkoxy (C≦8) , acyloxy (C≦8) , alkylamino (C≦8) , alkoxyamino (C≦8) , dialkylamino (C≦8) , alkenylamino (C≦8) , alkynylamino (C≦8) , arylamino (C≦8) , aralkylamino (C≦8) , heteroarylamino (C≦8) , heteroaralkylamino (C≦8) , amido (C≦8) , or a substituted version of any of these groups;

or a pharmaceutically acceptable salt, tautomer, or optical isomer thereof.

3. The pharmaceutical composition of claim 2 , wherein the compound is further defined as:

wherein R a is alkoxy (C1-4) , alkylamino (C1-4) , alkoxyamino (C1-4) , dialkylamino (C2-4) , or a substituted version of any of these groups; or a pharmaceutically acceptable salt, tautomer, or optical isomer thereof.

4. The pharmaceutical composition of claim 2 , wherein the compound is further defined as:

wherein R a is hydrogen, hydroxy, amino, methoxy, or 2,2,2-trifluoroethylamino; or a pharmaceutically acceptable salt, tautomer, or optical isomer thereof.

5. The pharmaceutical composition of claim 1 , wherein the compound is further defined as:

wherein Y is heteroaryl (C≦8) or a substituted heteroaryl (C≦8) ; or a pharmaceutically acceptable salt, tautomer, or optical isomer thereof.

6. The pharmaceutical composition of claim 1 , wherein X is OR b .

7. The pharmaceutical composition of claim 6 , wherein R b is absent.

8. The pharmaceutical composition of claim 6 , wherein R b is hydrogen.

9. The pharmaceutical composition of claim 1 , wherein X is NR b .

10. The pharmaceutical composition of claim 9 , wherein R b is hydroxy.

11. The pharmaceutical composition of claim 1 , wherein the compound is further defined as:

12. The pharmaceutical composition of claim 1 , wherein the compound is further defined as:

13. The pharmaceutical composition of claim 1 , wherein the compound is further defined as:

14. The pharmaceutical composition of claim 1 , wherein the compound is further defined as:

15. The composition of claim 1 , wherein the compound is further defined as:

16. The pharmaceutical composition of claim 1 , wherein the compound is further defined as:

17. The pharmaceutical composition of claim 1 , wherein the compound is further defined as:

18. The pharmaceutical composition of claim 1 , wherein the compound is further defined as:

19. The pharmaceutical composition of claim 1 , wherein the compound is further defined as:

20. The pharmaceutical composition of claim 1 , wherein the compound is further defined as:

21. The pharmaceutical composition of claim 1 , wherein the compound is further defined as:

22. The pharmaceutical composition of claim 1 , wherein the compound is further defined as:

23. The pharmaceutical composition of claim 1 , wherein the composition is formulated for oral delivery.

24. A pharmaceutical composition comprising a compound of the formula:

and

a pharmaceutically acceptable carrier.