Carbazole-containing amides, carbamates, and ureas as cryptochrome modulators

A compound of formula I

• or a pharmaceutically acceptable salt or hydrate thereof, wherein
• each of A, D, E, G, J, L, M, and Q is independently N or C;
• each of R1 and R2, when A, D, E, G, J, L, M, or Q is C, is independently selected from H, halo, cyano, nitro, —CF3, —CHF2, —CH2F, trifluoromethoxy, azido, hydroxyl, (C1-C6)alkoxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(C═O)—R8, —(C═O)—O—R8, —O—(C═O)—R8, —NR8(C═O)—R10, —(C═O)—NR8R9, —NR8R9, —NR8OR9, —S(O)cNR8R9, —S(O)d(C1-C8)alkyl, —O—SO2—R8, NR8—S(O)c, —(CR8R9)d(3-10)-membered cycloalkyl, —(CR8R9)e(C6-C10)aryl, —(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)f(C═O)(CR8R9)e(C6-C10)aryl, —(CR8R9)f(C═O)(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)eO(CR8R9)f(C6-C10)aryl, —(CR8R9)eO(CR8R9)f(4-10)-membered heterocyclyl, —(CR8R9)fS(O)d(CR8R9)e(C6-C10)aryl, and —(CR8R9)fS(O)d(CR8R9)e(4-10)-membered heterocyclyl;
• each of R3 and R5 is independently selected from H, cyano, —CF3, —CHF2, —CH2F, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(C═O)—R8, —(C═O)—O—R8, —(C═O)—NR8R9, —S(O)cNR8R9, —S(O)d(C1-C8)alkyl, —(CR8R9)d(3-10)-membered cycloalkyl, —(CR8R9)e(C6-C10)aryl, —(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)f(C═O)(CR8R9)e(C6-C10)aryl, —(CR8R9)f(C═O)(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)eO(CR8R9)f(C6-C10)aryl, —(CR8R9)eO(CR8R9)f(4-10)-membered heterocyclyl, —(CR8R9)fS(O)d(CR8R9)e(C6-C10)aryl, and —(CR8R9)fS(O)d(CR8R9)e(4-10)-membered heterocyclyl;
• wherein each of the R3 groups are optionally linked to each other as a 4-12 membered mono- or bicyclic ring;
• wherein each of the R5 groups are optionally linked to each other as a 4-12 membered mono- or bicyclic ring;
• R4 is H, —CF3, —CHF2, —CH2F, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(C═O)—R8, —(C═O)—O—R8, —(C═O)—NR8R9, —(CR8R9)d(3-10)-membered cycloalkyl, —(CR8R9)e(C6-C10)aryl, —(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)f(C═O)(CR8R9)e(C6-C10)aryl, —(CR8R9)f(C═O)(CR8R9)e(4-10)-membered heterocyclyl, —(CR8R9)eO(CR8R9)f(C6-C10)aryl, —(CR8R9)eO(CR8R9)f(4-10)-membered heterocyclyl, —CR8R9)fS(O)d(CR8R9)e(C6-C10)aryl, and —(CR8R9)fS(O)d(CR8R9)e(4-10)-membered heterocyclyl;
• wherein R6 and R7 are linked to each other as a 4-12 membered mono- or bicyclic ring;
• each of R8, R9 and R10 are independently selected from H, (C1-C6)alkyl, —(CR11R12)e(3-10)-membered cycloalkyl, —(CR11R12)g(C6-C10)aryl, and —(CR11R12)g(4-10)-membered heterocyclyl;
• any carbon atoms of the (C1-C6)alkyl, the (3-10)-membered cycloalkyl, the (C6-C10)aryl and the (4-10)-membered heterocyclyl of the foregoing R1, R2, R3, R4, R8, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16 are independently optionally substituted with 1 to 3 R14 substituents each independently selected from halo, cyano, nitro, —CF3, —CHF2, —CH2F, trifluoromethoxy, azido, hydroxyl, —O—R15, (C1-C6)alkoxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(C═O)—R11, —(C═O)—R15, —(C═O)—O—R11, —(C═O)—O—R15, —O—(C═O)—R11, —O—(C═O)—R15, —NR11(C═O)—R13, —(C═O)—NR11R12, —(C═O)—NR11R15, —NR11R12, —NR11R15, —NR11OR12, —NR11OR15, —S(O)cNR11R12, —S(O)cNR11R15, —S(O)d(C1-C6)alkyl, —S(O)dR15, —O—SO2—R11, —O—SO2—R15, —NR11—S(O)c, —NR15—S(O)c, —(CR11R12)e(3-10)-membered cycloalkyl, —(CR11R12)e(C6-C10)aryl, —(CR11R12)e(4-10)-membered heterocyclyl, —(CR11R12)f(C═O)(CR11R12)e(C6-C10)aryl, —(CR11R12)f(C═O)(CR11R12)e(4-10)-membered heterocyclyl, —(CR11R12)eO(CR11R12)f(C6-C10)aryl, —(CR11R12)eO(CR11R12)f(4-10)-membered heterocyclyl, —(CR11R12)fS(O)d(CR11R12)e(C6-C10)aryl, and —(CR11R12)fS(O)d(CR11R12)e(4-10)-membered heterocyclyl;
• any carbon atoms of the (C1-C6)alkyl, the (3-10)-membered cycloalkyl, the (C6-C10)aryl and the (4-10)-membered heterocyclyl of the foregoing R14 are independently optionally substituted with 1 to 3 R16 substituents each independently selected from halo, cyano, nitro, —CF3, —CHF2, —CH2F, trifluoromethoxy, azido, (CH2)eOH, (C1-C6)alkoxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(C═O)—R11, —(C═O)—R15, —(C═O)—O—R11, —(C═O)—O—R15, —O—(C═O)—R11, —O—(C═O)—R15, —NR11(C═O)—R13, —(C═O)—NR11R12, —NR11R12, and —NR11R15;
• any nitrogen atoms of the (4-10)-membered heterocyclyl of the foregoing R1, R2, R3, R4, R8, R6, R7, R8, R9, R10, R14, and R15 are independently optionally substituted with (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, —(C═O)—R11, —(C═O)—O—R11, —(C═O)—NR11R12, —(CR11R12)e(3-10)-membered cycloalkyl, —(CR11R12)e(C6-C10)aryl, —(CR11R12)e(4-10)-membered heterocyclyl, —(CR11R12)f(C═O)(CR11R12)e(C6-C10)aryl, or —(CR11R12)f(C═O)(CR11R12)e(4-10)-membered heterocyclyl;
• each R11, R12, and R13 are independently H or (C1-C6)alkyl;
• R15 is —(CR11R12)e(3-10)-membered cycloalkyl, —(CR11R12)e(C6-C10)aryl, or —(CR11R12)e(4-10)-membered heterocyclyl;
• a and b are each independently 1, 2, 3, or 4;
• c is 1 or 2;
• d is 0, 1, or 2;
• and
• e, f, and g are each independently 0, 1, 2, 3, 4, or 5.