Antidiabetic agents

A compound of the formula

• 37
• or the pharmaceutically acceptable salt thereof;
• wherein
• n is 0, 1, 2, 3 or 4;
• m is 0, 1, 2, 3 or 4;
• Z is oxygen or sulfur;
• R1 is
• 38
• wherein the dashed lines represent optional double bonds;
• a is 1, 2 or 3;
• each R2 is independently hydrogen, halo, hydroxy, amino, nitro, (C1-C6)alkoxy, cyano, C(O)H or (C1-C6)alkyl optionally substituted by one to three fluoro atoms;
• R3 is hydrogen, halo, cyano, (C1-C6)alkyl or (C1-C3)alkynyl;
• R4 is hydrogen, halo, cyano or (C1-C6)alkyl;
• R5 is
• 39
• wherein the dashed lines represent optional double bonds;
• A, B and E are each independently nitrogen or CR15;
• X and Y are each independently CH2, oxygen, S(O)d wherein d is 0, 1 or 2;
• nitrogen or NR16;
• R8, R9, R10 and R11 are each independently hydrogen or (C1-C6)alkyl;
• R12 is hydrogen, HC(O)(C0-C6)alkyl, carboxy(C0-C3)alkyl, R17R18N—C(O)-(C0-C3)alkyl, hydroxy(C1-C3)alkyl, R17(C1-C3)alkyl, R17R18N(C0-C3)alkyl, (C1-C6)alkyl-C(O)—NH, (C6-C10)aryl-C(O)—NH, (C6-C10)aryl(C1-C6)alkyl-C(O)—NH, (C2-C9)heteroaryl(C1-C6)alkyl-C(O)—NH, (C1-C6)alkylaminocarbonylamino, (C6-C10)arylaminocarbonylamino, (C6-C10)aryl(C1-C6)alkylaminocarbonylamino, (C2-C9)heteroaryl(C1-C6)alkylaminocarbonylamino, (C1-C6)alkylsulfonylamino, (C6-C10)aryl(C1-C6)alkylsulfonylamino, (C2-C9)heteroarylsulfonylamino, (C2-C9)heteroaryl(C1-C6)alkylsulfonylamino, (C1-C6)alkylsulfonyl N((C1-C6)alkyl), (C6-C10)aryl(C1-C6)alkylsulfonyl N((C1-C6)alkyl), (C2-C9)heteroarylsulfonyl N((C1-C6)alkyl), (C2-C9)heteroaryl(C1-C6)alkylsulfonyl N((C1-C6)alkyl), (C3-C7)cycloalkylamino, ((C3-C7)cycloalkyl)2amino, (C3-C7)cycloalkylcarbonylamino, (C6-C10)aryl(C3-C7)cycloalkylcarbonylamino, (C2-C9)heteroaryl(C3-C7)cycloalkylcarbonylamino, (C3-C7)cycloalkylaminocarbonylamino, (C6-C10)aryl(C3-C7)cycloalkylaminocarbonylamino, (C2-C9)heteroaryl(C3-C7)cycloalkylaminocarbonylamino, (C3-C7)cycloalkylsulfonylamino, (C6-C10)aryl(C3-C7)cycloalkylsulfonylamino, (C2-C9)heteroaryl(C3-C7)cycloalkylsulfonylamino, (C3-C7)cycloalkylsulfonyl N((C3-C7)cycloalkyl), (C6-C10)aryl(C3-C7)cycloalkylsulfonyl N((C3-C7)cycloalkyl, (C2-C9)heteroarylsulfonyl N((C3-C7)cycloalkyl), (C2-C9)heteroaryl(C3-C7)cycloalkylsulfonyl N((C3-C7)cycloalkyl), (C1-C6)alkyl S(O)c, (C3-C7)cycloalkyl S(O)c, (C6-C10)aryl(C1-C6)alkyl S(O)c, (C6-C10)aryl S(O)c, (C1-C6)alkylamino S(O)c, (C1-C6)arylamino S(O)c, (C6-C10)arylC1-C6)alkylamino S(O)c wherein c is 0, 1 or 2;
• R13 is hydrogen or (C1-C6)alkyl;
• R14 is hydrogen, hydroxy, (C1-C6)alkoxy, (C6-C10)aryloxy or NR17R18;
• R15 is hydrogen, (C1-C6)alkylcarbonylcarboxy, hydroxy(C1-C6)alkyl, (C1-C6)alkyl piperazinylcarbonyl or piperidinylcarbonyl;
• R16 is hydrogen, HCO, (C1-C6)alkyl, (C1-C6)alkoxycarbonyl(C1-C6)alkyl, carboxy(C1-C6)alkyl, piperidinyl(C1-C6)alkylcarbonyl;
• (C1-C6)acyl;
• piperidinyl carbonyl(C1-C6)alkyl, hydroxy(C1-C6)alkyl, halo(C1-C6)alkylcarbonyl or morpholinyl(C1-C6)alkylcarbonyl;
• R17 and R18 are each independently hydrogen, (C1-C6)alkyl, (C6-C10)aryl(C1-C6)alkyl and (C2-C9)heteroaryl(C1-C6)alkyl.