Psilocin derivatives as serotonergic psychedelic agents for the treatment of CNS disorders
AssigneeMindset Pharma Inc.
InventorsAbdelmalik Slassi, Joseph A. Araujo
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Abstract
The present application relates to psilocin derivatives of Formula (I), to processes for their preparation, to compositions comprising them and to their use in activation of a serotonin receptor in a cell, as well as to treating diseases, disorders or conditions by activation of a serotonin receptor in a cell.
Claims45
A compound of Formula (I) or a pharmaceutically acceptable salt and/or solvate thereof:
- wherein
- R1 is hydrogen;
- R2 is selected from hydrogen and deuterium;
- R3, R4, R5 and R6 are independently selected from hydrogen and deuterium;
- R7 is selected from hydrogen, deuterium, CH3 and CD3;
- R8 is selected from hydrogen, deuterium, CH3 and CD3;
- R9, R10 and R11 are independently selected from hydrogen and deuterium;
- Y is selected from X-A;
- X is O;
- and
- A is P(O)(OH)2;
- wherein at least one of R3, R4, R5 and R6 is deuterium;
- and/or
- wherein at least one of R7 and R8 comprises deuterium,
- provided the compound of Formula I is not a compound wherein
- A is P(O)(OH)2, R2 is hydrogen, R3, R4, R5 and R6 are all deuterium, R9, R10 and R11 are all hydrogen, and R7 and R8 are both CH3.
A compound of Formula (I) or a pharmaceutically acceptable salt and/or solvate thereof:
- wherein
- R1 is hydrogen;
- R2 is selected from hydrogen and deuterium;
- R3, R4, R5 and R6 are independently selected from hydrogen and deuterium;
- R7 is selected from hydrogen, deuterium, CH3 and CD3;
- R8 is selected from hydrogen, deuterium, CH3 and CD3;
- R9, R10 and R11 are independently selected from hydrogen and deuterium;
- Y is selected from X-A;
- X is O;
- A is H;
- and
- at least one of R3, R4, R5 and R6 is deuterium and/or at least one of R7 and R8 comprises deuterium;
- provided the compound of Formula I is not a compound wherein:
- R2 is hydrogen, R3, R4, R5 and R6 are all deuterium, R9, R10 and R11 are all hydrogen, and R7 and R8 are both CD3;
- or
- R2 is hydrogen, R3, R4, R5 and R6 are all deuterium, R9, R10 and R11 are all hydrogen, and R7 and R8 are both CH3.
A compound of Formula (I) or a pharmaceutically acceptable salt and/or solvate thereof:
- wherein
- R1 is hydrogen;
- R2 is selected from hydrogen and deuterium;
- R3, R4, R5, and R6 are independently selected from hydrogen and deuterium;
- R7 is selected from hydrogen, deuterium, CH3, and CD3;
- R8 is selected from hydrogen, deuterium, CH3, and CD3;
- R9, R10, and R11 are independently selected from hydrogen and deuterium, wherein at least one of R9, R10, and R11 is deuterium;
- Y is selected from X-A;
- X is O;
- and
- A is selected from H and P(O)(OH)2;
- wherein at least one of R3, R4, R5, and R6 is deuterium;
- and/or
- wherein at least one of R7 and R8 comprises deuterium.
A compound of Formula (I) or a pharmaceutically acceptable salt and/or solvate thereof:
- wherein
- R1 is hydrogen;
- R2 is selected from hydrogen and deuterium;
- R3, R4, R5, and R6 are independently selected from hydrogen and deuterium;
- R7 is selected from hydrogen, deuterium, CH32 and CD3;
- R8 is selected from hydrogen, deuterium, CH3, and CD3;
- R9, R10, and R11 are independently selected from hydrogen and deuterium;
- Y is selected from X-A;
- X is O;
- and
- A is H;
- wherein:
- at least one of R3, R4, R5, and R6 is deuterium;
- or
- at least one of R7 and R8 comprises deuterium;
- or
- at least one of R3, R4, R5, and R6 is deuterium and at least one of R7 and R8 comprises deuterium;
- and
- wherein:
- R7 is selected from CH3 and CD3 and R8 is selected from hydrogen and deuterium;
- or
- at least one of R3, R4, R5, and R6 is H;
- or
- R7 is selected from CH3 and CD3, R8 is selected from hydrogen and deuterium, and at least one of R3, R4, R5, and R6 is H.
Dependencies are inferred from the claim text.