Benzopyrancarboxylic acid derivatives for the treatment of diabetes and lipid disorders

A compound having the formula I:

• or a pharmaceutically acceptable salt or prodrug thereof, wherein:
• Z is selected from the group consisting of CH2 and C═O;
• R1 is selected from the group consisting of H, —OH, C1-7alkyl, C2-7alkenyl, C2-7alkynyl, —OC1-3alkyl, —OC2-3alkenyl, —OC2-3alkynyl, F, Br, Cl, and Ar, wherein alkyl, alkenyl, alkynyl, —Oalkyl, —Oalkenyl and —Oalkynyl are linear or branched and are optionally substituted with (a) 1-7 halogen atoms, (b) 1-3 groups independently selected from (i) —OC1-3alkyl, which is optionally substituted with 1-5 halogen atoms, and (ii) phenyl, which is optionally substituted with 1-3 groups independently selected from halogen, C1-5alkyl and —OC1-3alkyl, said C1-5alkyl and —OC1-3alkyl being linear or branched and optionally substituted with 1-5 halogens, or (c) a mixture of (a) and (b);
• Ar is Aryl, wherein Aryl is in each instance optionally substituted with 1-5 substituents independently selected from (a) halogen, (b) C1-5alkyl, (c) C2-5alkenyl, (d) C2-5alkynyl, (e) —OC1-5alkyl, (f) —OC2-5alkenyl, (g) —OC2-5alkynyl, (h) —SOxC1-5alkyl, (i) —SOxNRaRb, (j) —SOxphenyl, (k) —C(O)C1-3alkyl, and (l) —C(O)NRaRb, wherein in each instance, each alkyl, alkenyl and alkynyl is linear or branched and is optionally substituted with (a) 1-5 halogen atoms, (b) 1-2 groups independently selected from —OC1-3alkyl, which is linear or branched and is optionally substituted with 1-5 halogens, or (c) a mixture thereof, and wherein phenyl is optionally substituted with 1-3 substituents independently selected from halogen, C1-3alkyl, and C1-3alkoxy, wherein C1-3alkyl and C1-3alkoxy are linear or branched and are optionally substituted with 1-5 halogens;
• x is selected from 0, 1 and 2;
• Aryl is selected from phenyl and naphthyl;
• Ra and Rb are independently selected from the group consisting of H, C1-5alkyl, C2-5alkenyl, C2-5alkynyl, —C(O)C1-5alkyl, —C(O)C2-5alkenyl, —C(O)C2-5alkynyl, SOxC1-5alkyl, SOxphenyl, SOxNRdRe, —C(O)NRdRe, halogen, and phenyl, wherein in all instances, alkyl, alkenyl, and alkynyl are linear or branched and are optionally substituted with (a) 1-5 halogen atoms, (b) 1-3 groups independently selected from —OCH3, —OCF3 and phenyl, or (c) a mixture thereof, wherein phenyl in all occurrences is optionally substituted with 1-3 substituents independently selected from halogen, C1-3alkyl, and C1-3alkoxy, said C1-3alkyl and C1-3alkoxy being linear or branched and optionally substituted with 1-5 halogens;
• Rd and Re are independently selected from H, C1-5alkyl, C2-5alkenyl, C2-5alkynyl, and phenyl, wherein said alkyl, alkenyl, and alkynyl are linear or branched and are optionally substituted with (a) 1-5 halogen atoms, (b) 1-3 groups independently selected from —OCH3, —OCF3 and phenyl, or (c) a mixture thereof, wherein phenyl in all occurrences is optionally substituted with 1-3 substituents independently selected from halogen, C1-3alkyl, and C1-3alkoxy, said C1-3alkyl and C1-3alkoxy being linear or branched and optionally substituted with 1-5 halogens;
• X and Y are independently selected from the group consisting of O, S, SO, SO2, NRa and CH2;
• n is an integer from 1-6;
• R2, R3, R5, R6, R7, R8, R9 and R10 are independently selected from the group consisting of H, halogen, C1-7alkyl, C2-7alkenyl, C2-7alkynyl, —OH, —OC1-5alkyl, —OC2-5alkenyl, —OC2-5alkynyl, —C(O)C1-5alkyl, —C(O)C2-5alkenyl, —C(O)C2-5alkynyl, —C(O)OC1-5alkyl, —C(O)OC2-5alkenyl, —C(O)OC2-5alkynyl, —OC(O)C1-5alkyl, —OC(O)C2-5alkenyl, —OC(O)C2-5alkynyl, Ar, —OAr, —C(O)Ar, —C(O)OAr, —OC(O)Ar, C3-8Cycloalkyl, —OC3-8Cycloalkyl, —SOxC1-5alkyl, —SOxNRaRb, —SOxAr, and —C(O)NRaRb, wherein in each instance, each alkyl, alkenyl, and alkynyl is linear or branched and is optionally substituted with (a) 1-5 halogen atoms, (b) 1-2 groups independently selected from —OC1-3alkyl groups which are linear or branched and are optionally substituted with 1-5 halogens, (c) 1 group Ar or C3-6Cycloalkyl, or (d) a mixture of more than one of (a), (b) and (c);
• and
• R4 is OAr.