Inhibitors of Bruton's tyrosine kinase

A compound of Formula III,

• wherein:
• Q is or N;
• R is H, —R1, —R1—R2—R3, —R1—R3, or —R2—R3;
• R1 is aryl, heteroaryl, cycloalkyl, or heterocycloalkyl, each of which is optionally substituted with one or more lower alkyl, hydroxy, hydroxy lower alkyl, lower alkoxy, halo, nitro, amino, amido, cyano, oxo, or halo-lower alkyl;
• R2 is —C(═O), —O, —C(═O)O, —C(═O)NR2′, —C(R2′)2, —C(R2′)2C(═O), —C(R2′)2C(═O)NR2′, C(R2′)2 N(R2′)C(═O), —OC(R2′)2, —C(═NH), —C(R2′)2NR2′, or —S(═O)2;
• each R2′ is independently H, lower alkyl, or lower haloalkyl;
• R3 is H or R4;
• R4 is lower alkyl, lower alkoxy, amino, lower alkyl amino, lower dialkyl amino, aryl, arylalkyl, alkylaryl, heteroaryl, alkyl heteroaryl, heteroaryl alkyl, cycloalkyl, alkyl cycloalkyl, cycloalkyl alkyl, heterocycloalkyl, alkyl heterocycloalkyl, heterocycloalkyl alkyl, bicyclic cycloalkyl, bicyclic heterocycloalkyl, spirocycloalkyl, or spiroheterocycloalkyl, each of which is optionally substituted with one or more lower alkyl, lower alkyl amino, lower dialkyl amino, hydroxy, hydroxy lower alkyl, lower alkoxy, halo, nitro, amino, amido, acyl, cyano, oxo, guanidino, hydroxyl amino, carboxy, carbamoyl, carbamate, halo lower alkoxy, or halo lower alkyl, wherein two lower alkyl groups may together form a ring;
• X is CH or N;
• X′ is CH or N, with the proviso that when X is N, X′ is CH;
• Y1 is H, lower alkyl, or lower haloalkyl;
• Y2′ and each Y2 is independently halogen, oxime, or lower alkyl, wherein lower alkyl is optionally substituted with one or more substituents selected from the group consisting of hydroxy, lower alkoxy, lower haloalkoxy, lower haloalkyl, carboxy, amino, and halogen;
• n is 0, 1, or 2;
• each Y3 is independently H, halogen, or lower alkyl, wherein lower alkyl is optionally substituted with one or more substituents selected from the group consisting of hydroxy, lower alkoxy, amino, and halogen;
• m is 0 or 1;
• Y4 is Y4a, Y4b, Y4c, or Y4d;
• Y4a is H or halogen;
• Y4b is lower alkyl, optionally substituted with one or more substituents selected from the group consisting of haloalkyl, halogen, hydroxy, amino, cyano, and lower alkoxy;
• Y4c is lower cycloalkyl, optionally substituted with one or more substituents selected from the group consisting of lower alkyl, lower haloalkyl, halogen, hydroxy, hydroxy lower alkyl, amino, cyano, and lower alkoxy;
• Y4d is amino, optionally substituted with one or more lower alkyl, alkoxy lower alkyl, or hydroxy lower alkyl;
• and
• Y5 is halogen, hydroxy, lower alkyl, lower alkoxy, lower hydroxyalkyl, cyano, or lower haloalkyl;
• or a pharmaceutically acceptable salt thereof.