Biaryl linked hydroxamates: preparation and pharmaceutical applications

A compound of the Formula (I)

• wherein
• Z is a single bond or a C1-C4 hydrocarbon chain containing no more than 1 double or triple bond, optionally substituted with one or more substituents independently selected from the group consisting of C1-C4 alkyl;
• A is an aromatic ring selected from the group consisting of optionally substituted arylene and optionally substituted heteroarylene, wherein A is not benzimidazole and when Z is a single bond then A is not selected from the group consisting of phenylene and six-membered heteroarylene containing 3 or less than 3 nitrogens;
• B is an aromatic ring selected from the group consisting of aryl and heteroaryl and wherein A and B can not both be phenylene and wherein when Z is a single bond then B is not a bicyclic aryl or bicyclic heteroaryl;
• wherein A and B are connected via a carbon-carbon bond;
• R2 is selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, heteroalkyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl, arylalkenyl, cycloalkylheteroalkyl, heterocycloalkylheteroalkyl, heteroarylheteroalkyl, arylheteroalkyl, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, alkoxyaryl, alkenyloxy, alkynyloxy, cycloalkylkoxy, heterocycloalkyloxy, aryloxy, heteroaryloxy, arylalkyloxy, amino, alkylamino, aminoalkyl, acylamino, arylamino, phenoxy, benzyloxy, COOH, COOR4, SH, CONHR4, NHR4, —(CH2)nNHCOR4, NHCOR4, NHCOOR4 NHCONHR4, C(═NOH)R4, NHSOR4 NHSO2R4, —(CH2)n—NR6R7, alkoxycarbonyl, alkylaminocarbonyl, sulfonyl, alkylsulfonyl, alkylsulfinyl, aryisulfonyl, arylsulfinyl, aminosulfonyl, aminosulfinyl, SR4 and acyl each of which may optionally be substituted, provided that R2 does not contain the moiety NHCONHCO or NHCONHSO2;
• R3 is selected from the group consisting of H, halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, heteroalkyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl, arylalkenyl, cycloalkylheteroalkyl, heterocycloalkylheteroalkyl, heteroarylheteroalkyl, arylheteroalkyl, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, alkoxyaryl, alkenyloxy, alkynyloxy, cycloalkylkoxy, heterocycloalkyloxy, aryloxy, heteroaryloxy, arylalkyloxy, amino, alkylamino, aminoalkyl, acylamino, arylamino, phenoxy, benzyloxy, COOH, COOR4, SH, CONHR4, NHR4, —(CH2)nNHCOR4, NHCOR4, NHCOOR4 NHCONHR4, C(═NOH)R4, NHSOR4 NHSO2R4, —(CH2)n—NR6R7, alkoxycarbonyl, alkylaminocarbonyl, sulfonyl, alkylsulfonyl, alkylsulfinyl, arylsulfonyl, arylsulfinyl, aminosulfonyl, aminosulfinyl, SR4 and acyl;
• each of which may optionally be substituted provided that R3 does not contain the moiety NHCONHCO or NHCONHSO2;
• or R2 and R3 together with portion of ring B may form a non-aromatic ring fused to B;
• X and Y are the same or different and are independently selected from the group consisting of H, halogen, —CN, —NO2, —CF3, —OCF3, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, heteroalkyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, alkoxyaryl, alkoxyheteroaryl, alkenyloxy, alkynyloxy, cycloalkyloxy, cycloalkenyloxy, heterocycloalkyloxy, heterocycloalkenyloxy, aryloxy, heteroaryloxy, arylalkyl, heteroarylalkyl, arylalkyloxy, amino, alkylamino, acylamino, aminoalkyl, arylamino, sulfonylamino, sulfinylamino, sulfonyl, alkylsulfonyl, arylsulfonyl, aminosulfonyl, aminoalkyl, alkoxyalky, —COOH, —C(O)OR4, —COR4, —SH, —SR4, —OR4, acyl and —NR8R9 each of which may be optionally substituted;
• each R4 is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, haloalkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl and acyl each of which may be optionally substituted;
• each R6 and R7 is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, haloalkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl and acyl;
• each of which may be optionally substituted;
• each R8 and R9 is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, haloalkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl and acyl;
• each of which may be optionally substituted;
• n is an integer from 0 to 6,
• m is an integer from 0 to 4;
• or a pharmaceutically acceptable salt or prodrug thereof,
• wherein when A is 2,5-oxazolene and Z is single bond, R2=R3=H, then B is not a phenyl, 4-Cl-phenyl, 4-CH3—O-phenyl or 4-NO2-phenyl.