US 12,378,266 B2
Psilocin derivatives as serotonergic psychedelic agents for the treatment of CNS disorders
Abdelmalik Slassi, Mississauga (CA); and Joseph A. Araujo, Grimsby (CA)
Assigned to Mindset Pharma Inc., St-Laurent (CA)
Filed by Mindset Pharma Inc., St-Laurent (CA)
Filed on May 30, 2024, as Appl. No. 18/678,114.
Application 17/743,718 is a division of application No. 17/387,845, filed on Jul. 28, 2021, granted, now 11,427,604, issued on Aug. 30, 2022.
Application 18/678,114 is a continuation of application No. 18/109,890, filed on Feb. 15, 2023.
Application 18/109,890 is a continuation of application No. 17/743,718, filed on May 13, 2022, granted, now 11,597,738.
Application 17/387,845 is a continuation of application No. PCT/CA2021/050123, filed on Feb. 4, 2021.
Claims priority of provisional application 62/969,934, filed on Feb. 4, 2020.
Prior Publication US 2024/0317782 A1, Sep. 26, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 209/16 (2006.01); C07D 401/14 (2006.01); C07D 403/06 (2006.01); C07F 9/572 (2006.01)
CPC C07F 9/5728 (2013.01) [C07D 209/16 (2013.01); C07D 401/14 (2013.01); C07D 403/06 (2013.01); C07B 2200/05 (2013.01)] 45 Claims
 
1. A compound of Formula (I) or a pharmaceutically acceptable salt and/or solvate thereof:

OG Complex Work Unit Chemistry
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.