Psilocin derivatives as serotonergic psychedelic agents for the treatment of cns disorders

A compound of Formula (I) or a pharmaceutically acceptable salt, solvate and/or prodrug thereof:

• wherein R1 is selected from hydrogen, C1-C3 alkyl, C(O)R12, CO2R12, C(O)N(R12)2, S(O)R12 and SO2R12;
• R2 is selected from hydrogen and C1-C4alkyl
• R3, R4, R5 and R6 are independently selected from hydrogen and C1-C6alkyl;
• R7 and R8 are independently selected from hydrogen, substituted or unsubstituted C1-C6alkyl, substituted or unsubstituted C2-C6alkenyl, substituted or unsubstituted C2-C6alkynyl, substituted or unsubstituted C1-C6haloalkyl, substituted or unsubstituted C3-C7cycloalkyl, substituted or unsubstituted C3-C7heterocycloalkyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl, or
• R7 and R8 are taken together with the nitrogen atom therebetween to form a 3- to 7-membered heterocyclic ring optionally including 1 to 2 additional ring heteromoieties selected from O, S, S(O), SO2, N and NR13
• wherein said C3-C7cycloalkyl and 3- to 7-membered heterocyclic ring are each further optionally substituted with a substituent selected from, halogen, CO2R13, C(O)N(R13)2, SO2R13, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl and a 3- to 6-membered heterocyclic ring including 1 to 2 ring heteromoieties selected from O, S, N, S(O), SO2 and NR13;
• R9, R10 and R11 are independently selected from hydrogen, halogen, CN, OR13, N(R13)2, SR13, C1-C6alkyl, C1-C6haloalkyl, C2-C6haloalkenyl, CO2R13, C(O)N(R13)2, SOR13, SO2R13, C2-C6alkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C7cycloalkyl and a 3- to 7-membered heterocyclic ring including 1 to 2 ring heteromoieties selected from O, S, S(O), SO2, N and NR13, wherein said C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C7cycloalkyl and 3- to 7-membered heterocyclic ring groups are optionally substituted by one or more substituents independently selected from CN, OR13, N(R13)2 and SR13, and wherein said C3-C7cycloalkyl and 3- to 7-membered heterocyclic ring are each further optionally substituted with a substituent selected from halogen, CO2R13, C(O)N(R13)2, SO2R13, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl and a 3- to 6-membered heterocyclic ring including 1 to 2 ring heteromoieties selected from O, S, S(O), SO2, N and NR13;
• Y is selected from halogen and X-A;
• X is selected from O, NR13, S, S(O) and SO2;
• A is selected from hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C3-C7cycloalkyl, C4-C6cycloalkenyl, heterocycloalkyl, aryl, heteroaryl and P(O)(OR12)2;
• each R12 is independently selected from hydrogen, substituted or unsubstituted C1-C6alkyl, substituted or unsubstituted C2-C6alkenyl, substituted or unsubstituted C2-C6alkynyl, substituted or unsubstituted C1-C6haloalkyl, 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;
• each R13 is independently selected from hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C7cycloalkyl, and a 3- to 7-membered heterocyclic ring including 1 to 2 ring 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-C6cycloalkyl and 3- to 7-membered heterocyclic ring groups are optionally substituted by one or more substituents independently selected from CN, OR14, N(R14)2 and SR14, and wherein said C3-C7cycloalkyl and 3- to 7-membered heterocyclic ring are each further optionally substituted with a substituent selected from halogen, CO2R14, C(O)N(R14)2, SO2R14, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl and a 3- to 6-membered heterocyclic ring including 1 to 2 ring heteromoieties selected from O, S, S(O), SO2, N and NR14,
• R14 is selected from hydrogen, substituted or unsubstituted C1-C6alkyl, substituted or unsubstituted C2-C6alkenyl, substituted or unsubstituted C2-C6alkynyl, substituted or unsubstituted C1-C6haloalkyl, substituted or unsubstituted C3-C7cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;
• wherein at least one of R3, R4, R5 and R6 is deuterium or at least one of R3, R4, R5 and R6 comprises deuterium, and
• wherein all available hydrogen atoms are optionally substituted with a halogen atom and/or all available atoms are optionally substituted with an alternate isotope thereof.