Azophenols as ERG Oncogene Inhibitors

A compound of Formula (V)

• or a pharmaceutically acceptable salt thereof,
• wherein:
• R1 is selected from the group consisting of H and C1-C10 alkyl;
• and
• R2 is C2-C10 alkyl,
• with the proviso that when R1 is H, R2 is not ethyl, isobutyl or —C(CH3)2—CH2—C(CH3)3.

A pharmaceutical composition comprising the compound of Formula (I)

• or Formula (II)
• or a pharmaceutically acceptable salt thereof,
• wherein:
• X is NH, O or S;
• X1, X2, X3, X4 and X5 are independently N or CR9, where only one of X1, X2, X3, X4 and X5 is N;
• R1, R2 and R4 are independently selected from the group consisting of H, aryl, halogen, C1-C10 alkyl, C1-C10 alkoxy, C3-C7 cycloalkyl and C3-C7 heterocycloalkyl, wherein the aryl, C1-C10 alkyl, C1-C10 alkoxy, C3-C7 cycloalkyl and C3-C7 heterocycloalkyl are optionally substituted with one or more substituents selected from the group consisting of C1-C8 alkyl, C3-C7 cycloalkyl, C3-C7 heterocycloalkyl, aryl, heteroaryl, halogen, hydroxyl, —CN, —COOH, —CF3, —OCH2F, —OCHF2, —OC1-C8 alkyl, —O-aryl, —O— heteroaryl, —NR5R6, —NR5C(O)R6 and —C(O)NR5R6;
• R3 is selected from the group consisting of H, —OH, —NR5R6, C1-C10 alkyl, C1-C10 alkoxy, C3-C7 cycloalkyl and C3-C7 heterocycloalkyl, wherein the C1-C10 alkyl, C1-C10 alkoxy, C3-C7 cycloalkyl and C3-C7 heterocycloalkyl are optionally substituted with one or more substituents selected from the group consisting of C1-C8 alkyl, C3-C7 cycloalkyl, C3-C7 heterocycloalkyl, aryl, heteroaryl, halogen, hydroxyl, —CN, —COOH, —CF3, —OCH2F, —OCHF2, —OC1-C8 alkyl, —O-aryl, —O-heteroaryl, —NR5R6, —NR5C(O)R6 and —C(O)NR5R6;
• R5 and R6 are independently selected from the group consisting of H, C1-C8 alkyl, aryl and C3-C7 cycloalkyl, or R5 and R6 taken together form a C3-C7 heterocycloalkyl wherein the C1-C8 alkyl and C3-C7 heterocycloalkyl are optionally substituted with one or more substituents selected from the group consisting C1-C8 alkyl, C3-C7 cycloalkyl, C3-C7 heterocycloalkyl, aryl, heteroaryl, halogen, hydroxyl, —CN, —COOH, —CF3, —OCH2F, —OCHF2, —OC1-C8 alkyl, —O-aryl, —O-heteroaryl, —NR7R8, —NR7C(O)R8 and —C(O)NR7R8;
• R7 and R8 are independently selected from the group consisting of H and C1-C8 alkyl;
• each R9 is independently H, halogen, —CN, —OH, COOH, —NR10R11, C1-C10 alkyl, C3-C7 cycloalkyl, C1-C10 alkoxy and C3-C7 heterocycloalkyl wherein the C1-C10 alkyl, C3-C7 cycloalkyl, C1-C10 alkoxy and C3-C7 heterocycloalkyl are optionally substituted with one or more substituents selected from the group consisting of C1-C8 alkyl, C3-C7 cycloalkyl, C3-C7 heterocycloalkyl, aryl, heteroaryl, halogen, hydroxyl, —CN, —COOH, —CF3, —OCH2F, —OCHF2, —OC1—C alkyl, —O-aryl, —O-heteroaryl, —NR10R11, —NR10C(O)R11 and —C(O)NR10R11;
• R10 and R11 are independently selected from the group consisting of H, C1-C8 alkyl and C3-C7 cycloalkyl, or R10 and R11 taken together form a C3-C7 heterocycloalkyl wherein the C1-C8 alkyl and C3-C7 heterocycloalkyl are optionally substituted with one or more substituents selected from the group consisting C1-C8 alkyl, C3-C7 cycloalkyl, C3-C7 heterocycloalkyl, aryl, heteroaryl, halo, hydroxyl, —CN, —COOH, —CF3, —OCH2F, —OCHF2, —OC1-C8 alkyl, —O-aryl, —O-heteroaryl, —NR12R13, —NR12C(O)R13 and —C(O)NR12R13;
• and
• R12 and R13 are independently selected from the group consisting of H and C1-C8 alkyl;
• the pharmaceutical composition further comprising an excipient.