Patent ID: 8618095

Claim:
A compound of formula: or a pharmaceutically acceptable salt thereof, wherein: Y is oxygen or sulfur; Z 1 , Z 2 , and Z 3 are independently selected from CH and N, provided that at least one of Z 1 Z 2 and Z 3 is N; R 1 is hydrogen or C 1 -C 6 alkyl; R 2 and R 3 are independently selected from hydrogen, halogen, C 1 -C 6 alkyl, and halo(C 1 -C 6 alkyl), or R 2 and R 3 together with the carbon to which they are attached form C 3 -C 6 cycloalkyl; R 4 is hydrogen, halogen, cyano, nitro, C 1 -C 6 alkyl, or halo(C 1 -C 6 alkyl); R 5 is C 1 -C 6 alkyl, â€”N(R 7 ) 2 , aryl optionally substituted with 1, 2, 3, or 4 R 6 groups, heteroaryl optionally substituted with 1, 2, 3, or 4 R 6 groups, cycloalkyl optionally substituted with 1, 2, 3, 4, 5, 6, 7, or 8 R 6 groups, or heterocycloalkyl optionally substituted with 1, 2, 3, 4, 5, 6, 7, or 8 R 6 groups, in which each R 6 is independently selected from deuterium, halogen, cyano, nitro, hydroxy, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, halo(C 1 -C 6 alkyl), C 1 -C 6 alkoxy, halo(C 1 -C 6 alkoxy), amino, (C 1 -C 6 alkyl)amino, di(C 1 -C 6 alkyl)amino, hydroxy(C 1 -C 6 alkyl), (C 1 -C 6 alkoxy)C 1 -C 6 alkyl, amino(C 1 -C 6 alkyl), ((C 1 -C 6 alkyl)amino)(C 1 -C 6 alkyl), (di(C 1 -C 6 alkyl)amino)(C 1 -C 6 alkyl), â€”C(O)OH, â€”C(O)NH 2 , C 3 -C 8 cycloalkyl, aryl, heteroaryl, and heterocycloalkyl, or two R 6 groups form a spiro-fused C 3 -C 6 cycloalkyl, a spiro-fused heterocycloalkyl, oxo, â•CH 2 , or â•CH(C 1 -C 6 alkyl); and each R 7 is independently selected from hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, halo(C 1 -C 6 alkyl), hydroxy(C 1 -C 6 alkyl), (C 1 -C 6 alkoxy)C 1 -C 6 alkyl, aryl, heteroaryl, heterocycloalkyl, (aryl)C 1 -C 6 alkyl, (heteroaryl)C 1 -C 6 alkyl, and (heterocycloalkyl)C 1 -C 6 alkyl; wherein the arylene is further substituted with 0, 1, 2, 3, or 4 R 9 , where each R 9 is independently selected from halogen, cyano, C 1 -C 6 alkyl, halo(C 1 -C 6 alkyl), C 1 -C 6 alkoxy, and halo(C 1 -C 6 alkoxy), or R 9 and R 5 together with the carbons to which they are attached form C 5 -C 10 heterocycloalkyl; and the heteroarylene is further substituted with 0, 1, 2, 3, or 4 R 10 , where each R 10 is independently selected from halogen, cyano, C 1 -C 6 alkyl, halo(C 1 -C 6 alkyl), C 1 -C 6 alkoxy, and halo(C 1 -C 6 alkoxy), or R 10 and R 5 together with the carbons to which they are attached form C 5 -C 10 heterocycloalkyl, provided the compound is not N4-(3,4-dihydro-3-oxo-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-5-fluoro-N2-(4-morpholinophenyl)-2,4-pyrimidinediamine, N4-(2,2-dimethyl-3,4-dihydro-3-oxo-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-5-fluoro-N2-(4-morpholinophenyl)-2,4-pyrimidinediamine, N4-(2,2-dimethyl-3,4-dihydro-3-oxo-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-5-fluoro-N2-(4-(4-methylpiperazin-1-yl)phenyl)-2,4-pyrimidinediamine, or N4-(3,4-dihydro-3-oxo-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-5-fluoro-N2-(4-ethoxycarbonylpiperazin-1-yl(phenyl))-2,4-pyrimidinediamine.