Heteroaromatic glucokinase activators

A compound of formula I:

• wherein, the * indicates an asymmetric atom;
• R1 is selected from the group consisting of H, Cl, F, Br, I, NH2, —NHOH, —CN, —NO2, C1-6 alkyl, —OR5, —C(O)OR6, perfluoro-C1-6 alkyl, C1-6 alkyl-S—, perfluoro-C1-6 alkyl-S—, C1-6 alkyl-SO2—, perfluoro-C1-6 alkyl-SO2—, C1-6 alkoxy-C1-6 alkyl-SO2—, C1-6 alkyl-S(O)—, and —SO2NR13R14;
• R2 is selected from the group consisting of C1-6 alkyl-SO2—, C3-6 cycloalkyl-SO2—, perfluoro-C1-6 alkyl-SO2—, and C1-6 alkoxy-C1-6 alkyl-SO2—;
• R3 is cyclopentyl;
• ring A is a mono-substituted thiazole;
• wherein the substituent is selected from the group consisting of —SCN, —(CH2)0-2—S(O)p—(CH2)1-4—C(O)OR7;
• —(CH2)0-2—S(O)p—(CH2)1-4—C(O)OH;
• —(CH2)0-2—S(O)p—(CH2)n—NR10R11;
• —(CH2)0-2—S(O)p—(CH2)n—C(O)NR10R11;
• and —(CH2)n-5-6 membered heterocycle consisting of carbon atoms and 1-3 heteroatoms selected from S(O)p, O, and N and is substituted with 0-1 C1-4 alkyl;
• and, R7, at each occurrence, is independently selected from the group consisting of C1-4 alkyl and C3-6 cycloalkyl;
• R5, at each occurrence, is independently selected from the group consisting of H, C1-6 alkyl, and perfluoro-C1-6 alkyl;
• R6, at each occurrence, is independently C1-6 alkyl;
• R8, at each occurrence, is independently selected from the group consisting of H, C1-8 alkyl, —(CH2)n—OH, —(CH2)n—C(O)OH, aryl, and 5-10 membered heteroaryl consisting of carbon atoms and 1-3 heteroatoms selected from S(O)p, O, and N;
• R9, at each occurrence, is independently selected from the group consisting of H, C1-8 alkyl, —(CH2)n—OH, —(CH2)n—C(O)OH, aryl, and 5-10 membered heteroaryl consisting of carbon atoms and 1-3 heteroatoms selected from S(O)p, O, and N;
• alternatively, R8 and R9, together with the nitrogen to which they are attached form a 5-6 membered heterocycle, consisting of, in addition to the nitrogen atom to which R8 and R9 are attached, carbon atoms and 0-2 heteroatoms selected from S(O)p, O, and N;
• R10, at each occurrence, is independently selected from the group consisting of H;
• C1-6 alkyl;
• —(CH2)n—OH;
• —(CH2)n—C(O)OH;
• —(CH2)n—C3-8 cycloalkyl;
• —(CH2)n-aryl;
• —(CH2)n-5-10 membered heterocycle consisting of carbon atoms and 1-3 heteroatoms selected from S(O)p, O, and N;
• —(CH2)n-5-10 membered heteroaryl consisting of carbon atoms and 1-3 heteroatoms selected from S(O)p, O, and N;
• —(CH2)p—NHR7;
• and —(CH2)n—NR7R7;
• R11, at each occurrence, is independently selected from the group consisting of H;
• C1-6 alkyl;
• —(CH2)n—OH;
• —(CH2)n—C(O)OH;
• —(CH2)n—C3-8 cycloalkyl;
• —(CH2)n-aryl;
• —(CH2)n-5-10 membered heterocycle consisting of carbon atoms and 1-3 heteroatoms selected from S(O)p, O, and N;
• —(CH2)n-5-10 membered heteroaryl consisting of carbon atoms and 1-3 heteroatoms selected from S(O)p, O, and N;
• —(CH2)n—NHR7;
• and —(CH2)n—NR7R7;
• alternatively, R10 and R11, together with the nitrogen to which they are attached form a 5-6 membered heterocycle, consisting of, in addition to the nitrogen atom to which R10 and R11 are attached, carbon atoms and 0-2 heteroatoms selected from S(O)p, O, and N;
• and wherein the heterocycle thus formed is substituted with 0-2 R12;
• R12, at each occurrence, is independently selected from the group consisting of C1-6 alkyl, Cl, F, Br, I, NO2, —CN, —(CH2)n—OH, —(CH2)n—C(O)OH, NR8R9, NHS(O)2CH3, S(O)2CH3, and S(O)2NH2;
• R13, at each occurrence, is independently selected from the group consisting of H and C1-4 alkyl;
• R14, at each occurrence, is independently selected from the group consisting of H and C1-4 alkyl;
• p, at each occurrence, is selected from 0, 1, and 2;
• and
• n, at each occurrence, is independently selected from 0, 1, 2, 3, 4, 5, and 6 or a pharmaceutically acceptable salt thereof.