Biologically active 4H-benzo [1,4]oxazin-3-ones

A method of treating a subject suffering from a disorder in glucose and lipid metabolism, which comprises administering to the subject a therapeutically effective amount of a compound of Formula (I)

• or an optical isomer, enantiomer, diastereomer, racemate or racemic mixture thereof, ester, prodrug form, or a pharmaceutically acceptable salt thereof, wherein
• A is selected from aryl, heterocyclyl, and C1-C10 alkyl, said aryl, heterocyclyl, and C1-C10 alkyl being optionally substituted with one or more members selected from the group consisting of halogen, OH, aryl, C3-C8 cycloalkyl, C1-C10 alkyl substituted with a halogen, C1-C10 alkyl ether, heterocyclyl, carbonyl, oxime, —C(NNR3R4)R1, —COOR1, —CONR1R2, —OC(O)R1, —OC(O)OR1, —OC(O)NR1R2, —NR1R2, —NR3C(O)R1, —NR3C(O)OR1, and —NR3C(O)NR1R2, wherein
• R1 and R2 are independently selected from hydrogen, C1-C10 alkyl, aryl, heterocyclyl, and alkylaryl, or R1 and R2 may be taken together to form a 5- to 10-member ring;
• and
• R3 and R4 are independently selected from hydrogen, C1-C10 alkyl, aryl, heterocyclyl, alkylaryl, —C(O)R1, or —C(O)NR1R2;
• Z1 is selected from hydrogen, C1-C6 alkyl, aryl, heterocyclyl, COOR1, CONR1R2, OH, C1-C6 alkyl ether, —OC(O)R1, —OC(O)OR1, OC(O)NR1R2, —NR1R2, —NR3C(O)R1, —NR3C(O)OR1, —NR3C(O)NR1R2, halogen, —C(O)R1, —C(NR3)R1, —C(NOR3)R1, and —C(NNR3R4)R1;
• Z2 is selected from halogen, C1-C6 alkyl;
• Z1 and Z2 may together form a fused aromatic ring;
• n is an integer from 0 to 3;
• G is selected from —COOR1, —C(O)COOR1, —CONR1R2, —CF3, —P(O) (OR1) (OR2), —S—R8,
• R5 and R6 are independently hydrogen or C1-C6 alkyl;
• R7 is hydrogen, C1-C6 alkyl, or
• R8 is selected from the group consisting of hydrogen, C1-C6 alkyl, and substituted C1-C6 alkyl;
• and
• B is oxygen or —NR5;
• E is selected from hydrogen, C1-C6 alkyl and a moiety of the formula
• X is hydrogen or oxygen, with the proviso that
• when E is hydrogen and G is —COOH, —COOCH3, or a moiety of the formula of
• A is selected from the group consisting of aryl, heterocyclyl, substituted C1-C6 alkyl and C7-C10 alkyl, provided that when X is hydrogen, n is 1 and G is a moiety of the formula of
• A is selected from the group consisting of heterocyclyl, and C7-C10 alkyl.

A method of inhibiting in a subject the onset of a disorder in glucose and lipid metabolism, which comprises administering to the subject a prophylactically effective dose of a compound according to Formula (I):

• or an optical isomer, enantiomer, diastereomer, racemate or racemic mixture thereof, ester, prodrug form, or a pharmaceutically acceptable salt thereof, wherein
• A is selected from aryl, heterocyclyl, and C1-C10 alkyl, said aryl, heterocyclyl, and C1-C10 alkyl being optionally substituted with one or more members selected from the group consisting of halogen, OH, aryl, C3-C8 cycloalkyl, C1-C10 alkyl substituted with a halogen, C1-C10 alkyl ether, heterocyclyl, carbonyl, oxime, —C(NNR3R4)R1, —COOR1, —CONR1R2, —OC(O)R1, —OC(O)OR1, —OC(O)NR1R2, —NR1R2, —NR3C(O)R1, —NR3C(O)OR1, and —NR3C(O)NR1R2, wherein
• R1 and R2 are independently selected from hydrogen, C1-C10 alkyl, aryl, heterocyclyl, and alkylaryl, or R1 and R2 may be taken together to form a 5- to 10-member ring;
• and
• R3 and R4 are independently selected from hydrogen, C1-C10 alkyl, aryl, heterocyclyl, alkylaryl, —C(O)R1, or —C(O)NR1R2;
• Z1 is selected from hydrogen, C1-C6 alkyl, aryl, heterocyclyl, COOR1, CONR1R2, OH, C1-C6 alkyl ether, —OC(O)R1, —OC(O)OR1, —OC(O)NR1R2, —NR1R2, —NR3C(O)R1, —NR3C(O)OR1, —NR3C(O)NR1R2, halogen, —C(O)R1, —C(NR3)R1, —C(NOR3)R1, and —C(NNR3R4)R1;
• Z2 is selected from hydrogen, halogen, C1-C6 alkyl;
• X is hydrogen or oxygen, with the proviso that
• when E is hydrogen and G is —COOH, —COOCH3, or a moiety of the formula of
• A is selected from the group consisting of aryl, heterocyclyl, substituted C1-C6 alkyl and C7-C10 alkyl, provided that when X is hydrogen, n is 1 and G is a moiety of the formula of
• A is selected from the group consisting of heterocyclyl, and C7-C10 alkyl.