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

A compound of the formula:

• wherein:
• Y is cyano or —C(O)Ra, wherein
• Ra is:
• hydrogen, hydroxy, halo, amino, hydroxyamino, azido or mercapto;
• 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), alkenyl-oxy(C≦12), alkynyloxy(C≦12), aryloxy(C≦12), aralkoxy(C≦12), heteroaryloxy(C≦12), heteroaralkoxy(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), alkoxyamino(C≦12), alkenylamino(C≦12), alkynylamino(C≦12), arylamino(C≦12), aralkylamino(C≦12), heteroarylamino(C≦12), heteroaralkyl-amino(C≦12), alkylsulfonylamino(C≦12), amido(C≦12), alkylthio(C≦12), alkenylthio(C≦12), alkynylthio(C≦12), arylthio(C≦12), aralkylthio(C≦12), heteroarylthio(C≦12), heteroaralkylthio(C≦12), acylthio(C≦12), alkylammonium(C≦12), alkylsulfonium(C≦12), alkylsilyl(C≦12), or a substituted version of any of these groups;
• X is ORb, NRbRc, or SRb, wherein Rb and Rc are each independently:
• hydrogen;
• alkyl(C≦8), aryl(C≦8), aralkyl(C≦8), acyl(C≦8), or a substituted version of any of these groups;
• or
• provided that Rb is absent when the atom to which it is bound is part of a double bond, further provided that when Rb is absent the atom to which it is bound is part of a double bond;
• and
• R1 is:
• hydrogen, cyano, 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), 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 a salt or tautomer thereof.

A compound of the formula:

• wherein:
• Y is cyano or —C(O)Ra, wherein
• Ra is:
• hydrogen, hydroxy, halo, amino, hydroxyamino, azido or mercapto;
• 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), alkenyl-oxy(C≦12), alkynyloxy(C≦12), aryloxy(C≦12), aralkoxy(C≦12), heteroaryloxy(C≦12), heteroaralkoxy(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), alkoxyamino(C≦12), alkenylamino(C≦12), alkynylamino(C≦12), arylamino(C≦12), aralkylamino(C≦12), heteroarylamino(C≦12), heteroaralkyl-amino(C≦12), alkylsulfonylamino(C≦12), amido(C≦12), alkylthio(C≦12), alkenylthio(C≦12), alkynylthio(C≦12), arylthio(C≦12), aralkylthio(C≦12), heteroarylthio(C≦12), heteroaralkylthio(C≦12), acylthio(C≦12), alkylammonium(C≦12), alkylsulfonium(C≦12), alkylsilyl(C≦12), or a substituted version of any of these groups;
• X is ORb, NRbRc, or SRb, wherein Rb and Rc are each independently:
• hydrogen;
• alkyl(C≦8), aryl(C≦8), aralkyl(C≦8), acyl(C≦8), or a substituted version of any of these groups;
• or
• provided that Rb is absent when the atom to which it is bound is part of a double bond, further provided that when Rb is absent the atom to which it is bound is part of a double bond;
• and
• R1 is:
• hydrogen, cyano, 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), 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;
• R′ is hydroxy, alkoxy(C≦12), substituted alkoxy(C≦12), aryloxy(C≦12), substituted aryloxy(C≦12), aralkoxy(C≦12), substituted aralkoxy(C≦12), acyloxy(C≦12), or substituted acyloxy(C≦12);
• or a salt or tautomer thereof.