Carbonylamino-benzimidazole derivatives as androgen receptor modulators

A compound of formula I:

• or a pharmaceutically acceptable salt or stereoisomer thereof, wherein:
• a is 0 or 1;
• b is 0 or 1;
• R1 is thiazolyl, optionally substituted with one or more R4 groups;
• R2 is —(C═O)NR5R6;
• R3 and R4 are each independently selected from:
• 1) hydrogen,
• 2) halogen,
• 3) —(C═O)aOb(C1-10)alkyl,
• 4) —(C═O)aOb(C2-8)alkenyl,
• 5) —(C═O)aOb(C2-8)alkynyl,
• 6) —(C═O)aOb(C3-10)cycloalkyl,
• 7) —(C═O)aOb(C3-8)heterocyclyl,
• 8) —(C═O)aObaryl,
• 9) —(C═O)aNR5R6,
• 10) —Ob(C═O)NR5R6,
• 11) —NR5(C═O)aObRb,
• 12) —NR5(C═O)NR5R6,
• 13) —NR5S(O)2Rb,
• 14) —(C═O)OH,
• 15) trifluoromethoxy,
• 16) trifluoroethoxy,
• 17) —Ob(C1-10)perfluoroalkyl,
• 18) —S(O)2Ob(C1-10)alkyl,
• 19) —S(O)2Ob(C2-8)alkenyl,
• 20) —S(O)2Ob(C2-8)alkynyl,
• 21) —S(O)2Ob(C3-10)cycloalkyl,
• 22) —S(O)2Ob(C3-8)heterocyclyl,
• 23) —S(O)2Obaryl,
• 24) —NR5S(O)2NR5R6,
• 25) —CN
• 26) —NO2, and
• 27) OH,
• wherein, said aryl, alkyl, alkenyl, alkynyl, heterocyclyl, and cycloalkyl are each optionally substituted with one or more RZ groups;
• R5 is selected from:
• 1) hydrogen,
• 2) —(C═O)aOb(C1-10)alkyl,
• 3) —(C═O)aOb(C2-8)alkenyl,
• 4) —(C═O)aOb(C2-8)alkynyl,
• 5) —(C═O)aOb(C3-10)cycloalkyl,
• 6) —(C═O)aOb(C3-8)heterocyclyl,
• 7) —(C═O)aObaryl,
• 8) —(C═O)N(Rb)2,
• 9) trifluoromethoxy,
• 10) trifluoroethoxy,
• 11) —(C1-10)perfluoroalkyl,
• 12) —S(O)2N(Rb)2, and
• 13) —S(O)2ObRb,
• wherein said alkyl, cycloalkyl, aryl, heterocyclyl, alkenyl, and alkynyl are each optionally substituted with one or more RZ groups,
• R6 is selected from:
• 1) —(C═O)aOb(C1-10)alkyl,
• 2) —(C═O)aOb(C2-8)alkenyl,
• 3) —(C═O)aOb(C2-8)alkynyl,
• 4) —(C═O)aOb(C3-10)cycloalkyl,
• 5) —(C═O)aOb(C3-8)heterocyclyl,
• 6) —(C═O)aObaryl,
• 7) —(C═O)N(Rb)2,
• 8) trifluoromethoxy,
• 9) trifluoroethoxy,
• 10) —(C1-10)perfluoroalkyl,
• 11) —S(O)2N(Rb)2, and
• 12) —S(O)2ObRb,
• wherein, said aryl, heterocyclyl, alkenyl, and alkynyl are optionally substituted with one or more RZ groups, and wherein said alkyl and cycloalkyl are substituted with one or more RZ groups,
• with the proviso that RZ is other than hydrogen when R6 is alkyl or cycloalkyl,
• RZ is selected from:
• 1) hydrogen,
• 2) halogen,
• 3) —(C═O)aOb(C2-8)alkenyl,
• 4) —(C═O)aOb(C2-8)alkynyl,
• 5) —(C═O)aOb(C3-10)cycloalkyl,
• 6) —(C═O)aOb(C3-8)heterocyclyl,
• 7) —(C═O)aObaryl,
• 8) —(C═O)aN(Rb)2,
• 9) —Ob(C═O)N(Rb)2,
• 10) —NRb(C═O)aObRb,
• 11) —NRb(C═O)N(Rb)2,
• 12) —NRbS(O)2Rb,
• 13) —(C═O)OH,
• 14) trifluoromethoxy,
• 15) trifluoroethoxy,
• 16) —Ob(C1-10)perfluoroalkyl,
• 17) —S(O)2Ob(C1-10)alkyl,
• 18) —S(O)2Ob(C2-8)alkenyl,
• 19) —S(O)2Ob(C2-8)alkynyl,
• 20) —S(O)2Ob(C3-10)cycloalkyl,
• 21) —S(O)2Ob(C3-8)heterocyclyl,
• 22) —S(O)2Obaryl,
• 23) —S(O)2N(Rb)2
• 24) —NRbS(O)2N(Rb)2
• 25) —CN,
• 26) —NO2,
• 27) oxo, and
• 28) —OH,
• wherein, said aryl, alkyl, alkenyl, alkynyl, heterocyclyl, and cycloalkyl are each optionally substituted with one or more Ra groups;
• Ra is selected from hydrogen, OH, (C1-6)alkoxy, halogen,
• CO2H, CN, O(C═O)C1-6 alkyl, NO2, trifluoromethoxy, trifluoroethoxy,
• —Ob(C1-10)perfluoroalkyl, and NH2;
• and
• Rb is hydrogen, —(C═O)aOb(C1-10)alkyl, —(C═O)aOb(C2-8)alkenyl,
• —(C═O)aOb(C2-8)alkynyl, —(C═O)aOb(C3-10)cycloalkyl,
• —(C═O)aOb(C3-8)heterocyclyl, —(C═O)aObaryl,
• —(C═O)aOb(C1-10)alkyl, —S(O)2N(Ra)2, —S(O)2ObRa, trifluoromethoxy,
• trifluoroethoxy, or —Ob(C1-10)perfluoroalkyl,
• and wherein said alkyl, alkenyl, alkynyl, cycloalkyl, aryl, and heterocyclyl are optionally substituted with up to three substituents selected from CO2H, NH2, OH, (C1-6)alkoxy, halogen, CN, O(C═O)C1-6alkyl, NO2, trifluoromethoxy, trifluoroethoxy, —Ob(C1-10)perfluoroalkyl and N(Ra)2.