3-pyrrolidine-indole dimers as serotonergic agents useful for the treatment of disorders related thereto

A compound of Formula I:

• or a pharmaceutically acceptable salt, solvate, and/or prodrug thereof,
• wherein:
• Q is selected from P(O)OR9, C1-C4alkylene-P(O)OR9—C1-C6alkylene, C(O), S(O)2, C(O)Q′C(O), C(O)OQ′OC(O), and C(O)NR9′Q′NR9′C(O);
• R1 is selected from H, C1-C3alkyl, C(O)R10, CO2R10, C(O)N(R10)(R11), S(O)R10, and SO2R10;
• R2, R3, R4, and R5are independently selected from H and C1-C6alkyl;
• R6, R7, and R8 are independently selected from H, halo, CN, OR12, N(R12)(R13), SR12, C1-C6alkyl, C1-C6haloalkyl, C2-C6haloalkenyl, CO2R12, C(O)N(R12)(R13), S(O)R12, SO2R12, C2-C6alkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C7cycloalkyl, and C3-C7heterocycloalkyl comprising 1 to 2 heteromoieties selected from O, S, S(O), SO2, N, and NR14, wherein said C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C7cycloalkyl, and C3-C7heterocycloalkyl are optionally substituted by one or more substituents independently selected from CN, OR15, N(R15)(R16), and SR15, and wherein said C3-C7cycloalkyl and C3-C7heterocycloalkyl are each further optionally substituted with one or more substituents selected from halo, CO2R17, C(O)N(R17)(R18), SO2R17, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, and C3-C6heterocycloalkyl comprising 1 to 2 heteromoieties selected from O, S, S(O), SO2, N, and NR19;
• Q′ is selected from a direct bond, C1-C20alkylene, C1-C20haloalkylene, C2-C20alkenylene, C2-C20haloalkenylene, C2-C20alkynylene, C2-C20haloalkynylene, C3-C7cycloalkylene, and C3-C7heterocycloalkylene comprising 1 to 2 heteromoieties selected from O, S, S(O), SO2, N, and NR20, wherein said C1-C20alkylene, C2-C20haloalkylene, C2-C6alkenylene, C2-C20haloalkenylene, C3-C7cycloalkylene, and C3-C7heterocycloalkylene are optionally substituted with one or more substituents independently selected from CN, OR21, N(R21)(R22), and SR21, and/or are disubstituted on the same carbon atom with C1-6alkyl, or with C2-6alkylene to form a C3-C7cycloalkyl ring, and wherein said C3-C7cycloalkylene and C3-C7heterocycloalkylene are each further optionally substituted with one or more substituents selected from C1-C3alkyl and C1-C3haloalkyl, provided when Q is C(O)OQ′OC(O) or C(O)NR9′Q′NR9′C(O), then Q′ is not a direct bond;
• each R9, R10, R11, R12, R13, R14, R15, R16, R17, R18 R19, R20, R21, and R22 is independently selected from H, substituted or unsubstituted C1-C6alkyl, substituted or unsubstituted C2-C6alkenyl, substituted or unsubstituted C2-C6alkynyl, substituted or unsubstituted C1-C5haloalkyl, substituted or unsubstituted C3-C7cycloalkyl, substituted or unsubstituted C3-C7heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted C1-C6alkyleneC3-C7cycloalkyl, substituted or unsubstituted C1-C6alkyleneC3-C7heterocycloalkyl, substituted or unsubstituted C1-C6alkylenearyl, and substituted or unsubstituted C1-C6alkyleneheteroaryl;
• and
• R9′ is independently selected from H and C1-C6alkyl;
• wherein all available hydrogen atoms are optionally substituted with a fluorine atom or a chlorine atom and/or all available atoms are optionally substituted with an alternate isotope thereof.