Benzoylglycine derivatives and methods of making and using same

A method for preparing a benzamide of formula I-A

• or formula II-A
• the method comprising coupling a compound of formula:
• with a compound of formula:
• or
• wherein
• Y represents aryl optionally substituted with R8, heteroaryl optionally substituted with R8, or heterocyclyl optionally substituted with R8;
• m is an integer 0, 1, 2, 3, or 4;
• n is an integer 0, 1, 2, 3, or 4;
• R1 is hydrogen, C1-C6 alkyl optionally substituted with R9, aryl optionally substituted with R8, heteroaryl optionally substituted with R9, or heterocyclyl optionally substituted with R8;
• R5 is —CO2 (C1-C6 alkyl);
• R6 is hydrogen;
• each R7 is independently selected from the group consisting of halogen, —NO2, —CN, C1-C6 alkyl, C1-C6 haloalkyl, —NH2, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2, —OH, C1-C6 alkoxy, and C1-C6 haloalkoxy;
• each R8 is independently selected from the group consisting of halogen, —NO2, —CN, C1-C6 alkyl, C1-C6 haloalkyl, —NH2, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2, —OH, C1-C6 alkoxy, C1-C6 haloalkoxy, —CONH2, —CONH(C1-C6 alkyl), —CON(C1-C6 alkyl)2, —CONH—OH, —CONH—OCO(C1-C6 alkyl), —C(NH)NH—OH, —CONH—NH2, —CO2H, and —CO2(C1-C6 alkyl);
• or two R8 groups when attached to the same carbon atom form ═O;
• each R9 is independently selected from the group consisting of halogen, —NO2, —CN, C1-C6 alkyl, C1-C6 haloalkyl, —NH2, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2, —OH, C1-C6 alkoxy, and C1-C6 haloalkoxy;
• or two R9 groups when attached to the same carbon atom form ═O;
• R11 is —C≡C—R10, C1-C6 alkyl, C1-C6 haloalkyl, —CO(C1-C6 alkyl), —C1-C6 alkyl-CO(C1-C6 alkyl), —C1-C6 alkyl-CO2H, C3-C8 cycloalkyl optionally substituted with R18, (C3-C8 cycloalkyl)C1-C6 alkyl- optionally substituted with R18, or heterocyclyl optionally substituted with R18;
• wherein R10 is C1-C6 alkyl, C1-C6 haloalkyl, —CO(C1-C6 alkyl), —C1-C6 alkyl-CO(C1-C6 alkyl), —C1-C6 alkyl-CO2H, C3-C8 cycloalkyl optionally substituted with R19, (C3-C8 cycloalkyl)C1-C6 alkyl- optionally substituted with R19, or heterocyclyl optionally substituted with R19;
• each R17 is independently selected from the group consisting of halogen, —NO2, —CN, C1-C6 alkyl, C1-C6 haloalkyl, —NH2, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2, —OH, C1-C6 alkoxy, and C1-C6 haloalkoxy;
• each R18 is independently selected from the group consisting of halogen, —NO2, —CN, C1-C6 alkyl, C1-C6 haloalkyl, —NH2, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2, —OH, C1-C6 alkoxy, C1-C6 haloalkoxy, —C1-C6 alkyl-OH, —C1-C6 alkyl-(C1-C6 alkoxy), —C1-C6 alkyl-NH2, —C1-C6 alkyl-NH—C1-C6 alkyl, —C1-C6 alkyl-N(C1-C6 alkyl)2, —C1-C6 alkyl-NH(SO2C1-C6 alkyl), —CONH2, —CONH(C1-C6 alkyl), —CON(C1-C6 alkyl)2, —NH(SO2C1-C6 alkyl), —CONH—OH, —CONH—OCO(C1-C6 alkyl), —C(NH)NH—OH, —CONH—NH2, —CO(C1-C6 alkyl), —CO2H, —CO2(C1-C6 alkyl), —C1-C6 alkyl-CONH2, —C1-C6 alkyl-CONH(C1-C6 alkyl), —C1-C6 alkyl-CON(C1-C6 alkyl)2, —C1-C6 alkyl-CONH—OH, —C1-C6 alkyl-CO(C1-C6 alkyl), —C1-C6 alkyl-CO2H, and —C1-C6 alkyl-CO2(C1-C6 alkyl);
• or two R18 groups when attached to the same carbon atom form ═O;
• each R19 is independently selected from the group consisting of halogen, —NO2, —CN, C1-C6 alkyl, C1-C6 haloalkyl, —NH2, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2, —OH, C1-C6 alkoxy, C1-C6 haloalkoxy, —C1-C6 alkyl-OH, —C1-C6 alkyl-(C1-C6 alkoxy), —C1-C6 alkyl-NH2, —C1-C6 alkyl-NH—C1-C6 alkyl), —C1-C6 alkyl-N(C1-C6 alkyl)2, —C1-C6 alkyl-NH(SO2C1-C6 alkyl), —CONH2, —CONH(C1-C6 alkyl), —CON(C1-C6 alkyl)2, —NH(SO2C1-C6 alkyl), —CONH—OH, —CONH—OCO(C1-C6 alkyl), —C(NH)NH—OH, —CONH—NH2, —CO(C1-C6, alkyl), —CO2H, —CO2(—C1-C6 alkyl), —C1-C6 alkyl-CONH2, —C1-C6 alkyl-CONH(C1-C6alkyl), —C1-C6 alkyl-CON(C1-C6 alkyl)2, —C1-C6 alkyl-CONH—OH, —C1-C6alkyl-CO(C1-C6 alkyl), —C1-C6 alkyl-CO2H, and —C1-C6 alkyl-CO2(C1-C6 alkyl);
• or two R19 groups when attached to the same carbon atom form ═O;
• R15 is —CO2 (C1-C6 alkyl);
• R16 is hydrogen.