Antioxidant inflammation modulators: C-17 homologated oleanolic acid derivatives

A compound of the formula:

• wherein:
• Y is alkanediyl(C≦8), alkenediyl(C≦8), alkynediyl(C≦8), or a substituted version of any of these groups;
• Ra is:
• hydrogen, hydroxy, halo, amino, nitro, cyano, azido, phosphate, 1,3-dioxoisoindolin-2-yl, 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), acyl(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), dialkylamino(C≦12), alkenylamino(C≦12), alkynylamino(C≦12), arylamino(C≦12), aralkylamino(C≦12), heteroarylamino(C≦12), heteroaralkylamino(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), thioacyl(C≦12), alkylsulfonyl(C≦12), alkenylsulfonyl(C≦12), alkynylsulfonyl(C≦12), arylsulfonyl(C≦12), aralkylsulfonyl(C≦12), heteroarylsulfonyl(C≦12), heteroaralkylsulfonyl(C≦12), alkylsulfinyl(C≦12), alkenylsulfinyl(C≦12), alkynylsulfinyl(C≦12), arylsulfinyl(C≦12), aralkylsulfinyl(C≦12), heteroarylsulfinyl(C≦12), heteroaralkylsulfinyl(C≦12), alkylphosphonyl(C≦12), alkylphosphate(C≦12), dialkylphosphate(C≦12), alkylammonium(C≦12), alkylsulfonium(C≦12), alkylsilyl(C≦12), or a substituted version of any of these groups;
• or
• Y and Ra form a three to seven-membered ring, such that Y and Ra are further connected to one another through one or more of —O— and alkanediyl(C1-5), further wherein Y is —CH— and Ra is —CH2—;
• or
• Y, Ra, and carbon numbers 13, 17 and 18 form a ring such that Ra is bound to carbon 13, wherein Y is alkanediyl(C=1) or substituted alkanediyl(C=1) and Ra is —O—;
• X1 and X2 are independently:
• hydrogen, ORb, NRbRc, or SRb, wherein Rb and Rc 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
• a substituent convertible in vivo to hydrogen;
• 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;
• 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;
• R2 is:
• cyano;
• R3 is:
• absent or hydrogen;
• alkyl(C≦8), aryl(C≦8), aralkyl(C≦8), acyl(C≦8), or a substituted version of any of these groups;
• or
• a substituent convertible in vivo to hydrogen;
• provided that R3 is absent when the oxygen atom to which it is bound is part of a double bond, further provided that when R3 is absent the oxygen atom to which it is bound is part of a double bond;
• R4 and R5 are each independently alkyl(C≦8) or substituted alkyl(C≦8);
• R6 is hydrogen, hydroxy or oxo;
• and
• R7 is hydrogen or hydroxy;
• R8, R9, R10 and R11 are each independently hydrogen, hydroxy, alkyl(C≦8), substituted alkyl(C≦8), alkoxy(C≦8) or substituted alkoxy(C≦8);
• or a pharmaceutically acceptable salt or tautomer thereof.