Substituted azole acid derivatives useful as antidiabetic and antiobesity agents and method

A compound which has the structure

• 260
• wherein m is 0, 1 or 2;
• n=0, 1 or 2;
• Q is C or N
• A is (CH2)x where x is 1 to 5;
• or A is (CH2)x1, where x1 is 2 to 5, with an alkenyl bond or an alkynyl bond embedded in the chain;
• or A is —(CH2)x2—O—(CH2)x3— where x2 is 0 to 5 and x3 is 0 to 5, provided that at least one of x2 and x3 is other than 0,
• X1 is CH or N
• X2 is C, N, O or S;
• X3 is C, N, O or S;
• X4 is C, N, O or S, provided that at least one of X2,
• X3 and X4 is N;
• X5 is C, N, O or S;
• X6 is C or N;
• X7 is C, N, O or S, provided that at least one of X5, X6 or X7 is N;
• and where in each of X1 through X7, as defined above, C may include CH;
• R1 is H or alkyl;
• R2 is H, alkyl, alkoxy, halogen, amino or substituted amino;
• R2a, R2b and R2c are the same or different and are selected from H, alkyl, alkoxy, halogen, amino or substituted amino;
• R3 and R3a are the same or different and are independently selected from H, alkyl, arylalkyl, aryloxycarbonyl, alkyloxycarbonyl, alkynyloxycarbonyl, alkenyloxycarbonyl, arylcarbonyl, alkylcarbonyl, aryl, heteroaryl, alkyl(halo)aryloxycarbonyl, alkyloxy(halo)aryloxycarbonyl cycloalkylaryloxycarbonyl, cycloalkyloxyaryloxycarbonyl, cycloheteroalkyl, heteroarylcarbonyl, heteroaryl-heteroarylalkyl, alkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, alkoxycarbonylamino, aryloxycarbonylamino, heteroaryloxycarbonylamino, heteroaryl-heteroarylcarbonyl, alkylsulfonyl, alkenylsulfonyl, heteroaryloxycarbonyl, cycloheteroalkyloxycarbonyl, heteroarylalkyl, aminocarbonyl, substituted aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl, heteroarylalkenyl, cycloheteroalkylheteroarylalkyl, hydroxyalkyl, alkoxy, alkoxyaryloxycarbonyl, arylalkyloxycarbonyl, alkylaryloxycarbonyl, arylheteroarylalkyl, arylalkylarylalkyl, aryloxyarylalkyl, alkynyloxycarbonyl, haloalkoxyaryloxycarbonyl, alkoxycarbonylaryloxycarbonyl, aryloxyaryloxycarbonyl, arylsulfinylarylcarbonyl, arylthioarylcarbonyl, alkoxycarbonylaryloxycarbonyl, arylalkenyloxycarbonyl, heteroaryloxyarylalkyl, aryloxyarylcarbonyl, aryloxyarylalkyloxycarbonyl, arylalkenyloxycarbonyl, arylalkylcarbonyl, aryloxyalkyloxycarbonyl arylalkylsulfonyl, arylthiocarbonyl, arylalkenylsulfonyl, hateroarylsulfonyl, arylsulfonyl, alkoxyarylalkyl, heteroarylalkoxycarbonyl, arylheteroarylalkyl, alkoxyarylcarbonyl, aryloxyheteroarylalkyl, heteroarylalkyloxyarylalkyl, arylarylalkyl, arylalkenylarylalkyl, arylalkoxyarylalkyl, arylcarbonylarylalkyl, alkylaryloxyarylalkyl, arylalkoxycarbonylheteroarylalkyl, heteroarylarylalkyl, arylcarbonylheteroarylalkyl, heteroaryloxyarylalkyl, arylalkenylheteroarylalkyl, arylaminoarylalkyl or aminocarbonylarylarylalkyl;
• Y is CO2R4 (where R4 is H or alkyl, or a prodrug ester) or Y is a C-linked 1-tetrazole, a phosphinic acid of the structure P(O)(OR4a)R5, (where R4a is H or a prodrug ester, R5 is alkyl or aryl) or a phosphonic acid of the structure P(O) (OR4a)2′;
• (CH2)x, (CH2)x1, (CH2)x2, (CH2)x3, (CH2)m, and (CH2)n may be optionally substituted with 1, 2 or 3 substituents;
• including all stereoisomers thereof, a prodrug ester thereof, and a pharmaceutically acceptable salt thereof.