Carbazole derivatives

A compound of the formula:

• or a pharmaceutically acceptable salt thereof, wherein
• X, R1, R2, and R3 are each independently selected from H, halo, C1-C6 alkyl, halo(C1-C6)-alkyl, C1-C6 alkoxy, nitro, hydroxy, cyano, C2-C6 alkenyl, C2-C6 alkynyl, thiol, amino, mono- or di-(C1-C6)alkylamino, mono C3-C6 alkenylamino, carboxamide, aryl, heteroaryl, C3-C7 cycloalkyl, and C3-C7 cycloalkyl(C1-C6)alkyl, where each alkyl or cycloalkyl group is optionally substituted with aryl, heteroaryl, or 1-2 R22 groups,
• where each of the foregoing aryl and heteroaryl groups is optionally substituted with from 1-4 R22 groups;
• where R22 at each occurrence is independently C1-C6 alkyl, C1-C6 alkoxy, trifluoromethyl, halogen, hydroxy, amino, mono- or di-(C1-C6)alkylamino, nitro, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, or carboxamide;
• or R2 and R3 together with the atoms to which they are attached form a 5-12 membered mono-, bi-, or tricyclic ring system, where the 5-12 membered ring is partially unsaturated or aromatic and optionally contains one or two of oxygen, S(O)m where m is 0, 1, or 2, nitrogen, or NR7 where R7 is hydrogen or C1-C6 alkyl, and wherein the 5-12 membered ring is optionally substituted with 1 or 2 R22 groups;
• or R1 and X together with the atoms to which they are attached form a 5-12 membered mono-, bi-, or tricyclic ring system, where the 5-12 membered ring is partially unsaturated or aromatic and optionally contains one or two of oxygen, S(O)m where m is 0, 1, or 2, nitrogen, or NR7 where R7 is hydrogen or C1-C6 alkyl, and wherein the 5-12 membered ring is optionally substituted with 1 or 2 R22 groups;
• Y is H, NR7R7′, NR7(C3-C6)alkenyl, NR7CONHCOR7′, C(=Z)NR7R7′, NR7CONR7R7′, NR7COR7′, or —NR7—(C1-C6)alkyl-(C1-C6)alkoxy, where Z is O, S, or NOR7, and
• R7 and R7′ at each occurrence are independently selected from H and C1-C6 alkyl;
• R4 is H or C1-C6 alkyl optionally substituted with 1-2 groups selected from oxo, aryl, heteroaryl, or R22;
• R5 is OR7, NR7R7′, NR7OR7′, or C1-C6 alkyl optionally substituted with 1-2 groups selected from oxo, aryl, heteroaryl, or R22;
• or
• R4 and R5 together with the atoms to which they are attached form a 5-12 membered mono-, bi-, or tricyclic ring system, where the 5-12 membered ring is partially unsaturated or aromatic and optionally contains one or two of oxygen, S(O)m where m is 0, 1, or 2, nitrogen, NOR7 or NR7 where R7 is hydrogen or C1-C6 alkyl, and wherein the 5-12 membered ring is optionally substituted with 1 or 2 R22 groups;
• n is 0, 1, 2, 3, or 4;
• R6 at each occurrence is independently halo, C1-C6 alkyl, halo (C1-C6)-alkyl, C1-C6 alkoxy, nitro, hydroxyl, cyano, alkenyl, alkynyl, thiol, amino, mono- or di-(C1-C6) alkylamino, aryl, heteroaryl, C3-C7 cycloalkyl, and C3-C7 cycloalkyl(C1-C6)alkyl, where each alkyl or cycloalkyl group is optionally substituted with aryl, heteroaryl, or 1-2 R22 groups,
• where each of the foregoing aryl groups and heteroaryl groups is optionally substituted with from 1-4 R22 groups;
• or two R6 groups on adjacent carbons, together with the atoms to which they are attached, form a 5-12 membered mono-, bi-, or tricyclic ring system fused to the ring to which Y is attached, where the 5-12 membered ring is partially unsaturated or aromatic and optionally contains one or two of oxygen, S(O)m where m is 0, 1, or 2, nitrogen, or NR7 where R7 is hydrogen or C1-C6 alkyl, wherein the 5-12 membered ring is optionally substituted with 1 or 2 R22 groups;
• R8 is H;
• and
• R9 is OH;
• or R8 and R9 together are Q, wherein Q is ═O or ═NOR7, provided that when the 5-12 membered ring formed by R4 and R5 is aromatic, one of R8 and R9 is absent.