Psilocin derivatives as serotonergic psychedelic agents for the treatment of CNS disorders
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.
1. A compound of Formula IG, or a pharmaceutically acceptable salt or solvate thereof:
wherein
R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen and deuterium;
R 7 and R 8 are independently selected from the group consisting of hydrogen, and unsubstituted C 1-6 alkyl; or
R 7 and R 8 are taken together with the atoms to which they are attached form a 3- to 7-membered heterocyclic ring;
R 10 is selected from the group consisting of hydrogen, halogen, cyano and lower alkyl; and
Q′ is selected from
wherein one or more of R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 10 optionally comprises deuterium.
2. The compound of claim 1 , wherein Q′ is selected from the group consisting of:
3. The compound of claim 2 , wherein Q′ is
4. The compound of claim 1 , wherein R 3 , R 4 , R 5 , and R 6 are hydrogen.
5. The compound of claim 3 , wherein R 3 , R 4 , R 5 , and R 6 are hydrogen.
6. The compound of claim 1 having the following structure:
wherein
R 7 and R 8 are independently selected from the group consisting of hydrogen, and unsubstituted C 1-6 alkyl; or
R 7 and R 8 are taken together with the atoms to which they are attached form a 3- to 6-membered heterocyclic ring, or
a pharmaceutically acceptable salt or solvate thereof.
7. The compound of claim 6 , wherein R 7 and R 8 are independently selected from the group consisting of hexyl, pentyl, n-butyl, iso-buty, sec-butyl, tert-butyl, n-propyl, iso-propyl, ethyl, and methyl.
8. The compound of claim 7 , wherein R 7 and R 8 are independently selected from the group consisting of n-butyl, iso-butyl, sec-butyl, tert-butyl, n-propyl isopropyl, ethyl, and methyl.
9. The compound of claim 1 , wherein R 10 is hydrogen.
10. The compound of claim 3 , wherein R 10 is hydrogen.
11. The compound of claim 1 selected from the group consisting of:
or a pharmaceutically acceptable salt or solvate thereof.
12. The compound of claim 1 selected from the group consisting of:
or a pharmaceutically acceptable salt or solvate thereof.
13. The compound of claim 1 that is:
or a pharmaceutically acceptable salt or solvate thereof.
14. A pharmaceutical composition comprising one or more compounds of claim 1 , or a pharmaceutically acceptable salt and/or solvate thereof, and pharmaceutically acceptable carrier.
15. A pharmaceutical composition comprising the compound of claim 13 , or a pharmaceutically acceptable salt and/or solvate thereof, and pharmaceutically acceptable carrier.