IP Library › Granted Patent US 12,378,266

Granted Patent B2

US 12,378,266 · App. 18/678,114 · Granted Aug 5, 2025

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

Inventors: Abdelmalik Slassi (Mississauga, CA); Joseph A. Araujo (Grimsby, CA)

Assignee: Mindset Pharma Inc.

C07F9/5728 C07D209/16 C07D401/14 C07D403/06 C07B2200/05

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Quick Facts

Patent No.: US 12,378,266
App. No.: 18/678,114
Granted: Aug 5, 2025
Kind: B2

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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.

Claims (133)

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

wherein

R 1 is hydrogen;

R 2 is selected from hydrogen and deuterium;

R 3 , R 4 , R 5 and R 6 are independently selected from hydrogen and deuterium;

R 7 is selected from hydrogen, deuterium, CH 3 and CD 3 ;

R 8 is selected from hydrogen, deuterium, CH 3 and CD 3 ;

R 9 , R 10 and R 11 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 R 3 , R 4 , R 5 and R 6 is deuterium; and/or

wherein at least one of R 7 and R 8 comprises deuterium,

provided the compound of Formula I is not a compound wherein

A is P(O)(OH) 2 , R 2 is hydrogen, R 3 , R 4 , R 5 and R 6 are all deuterium, R 9 , R 10 and R 11 are all hydrogen, and R 7 and R 8 are both CH 3 .

2. The compound of claim 1 , wherein R 9 , R 10 and R 11 are all hydrogen.

3. The compound of claim 2 , wherein at least one of R 3 , R 4 , R 5 and R 6 is deuterium, and

R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium; or

R 7 and R 8 are both CH 3 or both CD 3 .

4. The compound of claim 3 , wherein R 3 and R 4 are both deuterium; or R 5 and R 6 are both deuterium, and

R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium.

5. The compound of claim 3 , wherein R 2 is hydrogen, R 3 , R 4 , R 5 and R 6 are all deuterium, R 7 is selected from CH 3 and CD 3 and R 8 is hydrogen, and the compound is selected from

or a pharmaceutically acceptable salt and/or solvate thereof.

6. The compound of claim 3 , wherein R 2 is hydrogen, at least one of R 3 , R 4 , R 5 and R 6 is deuterium, and R 7 and R 8 are both CH 3 or both CD 3 , and the compound is selected from

or a pharmaceutically acceptable salt and/or solvate thereof.

7. The compound of claim 3 , wherein R 2 is hydrogen, R 3 and R 4 are both deuterium; or R 5 and R 6 are both deuterium, and R 7 and R 8 are both CH 3 or both CD 3 , and the compound is selected from

or a pharmaceutically acceptable salt and/or solvate thereof.

8. The compound of claim 2 , wherein R 3 , R 4 , R 5 and R 6 are all hydrogen, and

R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium; or

R 7 and R 8 are both CD 3 .

9. The compound of claim 1 , wherein R 9 , R 10 and R 11 are all deuterium.

10. The compound of claim 9 , wherein at least one of R 3 , R 4 , R 5 and R 6 is deuterium, and

R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium; or

R 7 and R 8 are both CH 3 or both CD 3 .

11. The compound of claim 10 , wherein R 3 and R 4 are both deuterium; or R 5 and R 6 are both deuterium; or R 3 , R 4 , R 5 and R 6 are all deuterium, and

R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium.

12. The compound of claim 10 , wherein R 2 is deuterium, R 3 and R 4 are both deuterium; or

R 5 and R 6 are both deuterium, and R 7 and R 8 are both CH 3 or both CD 3 , and the compound is selected from

or a pharmaceutically acceptable salt and/or solvate thereof.

13. The compound of claim 10 , wherein R 2 is deuterium, R 3 , R 4 , R 5 and R 6 are all deuterium, and R 7 and R 8 are both CD 3 and the compound is

or a pharmaceutically acceptable salt and/or solvate thereof.

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

wherein

R 1 is hydrogen;

R 2 is selected from hydrogen and deuterium;

R 3 , R 4 , R 5 and R 6 are independently selected from hydrogen and deuterium;

R 7 is selected from hydrogen, deuterium, CH 3 and CD 3 ;

R 8 is selected from hydrogen, deuterium, CH 3 and CD 3 ;

R 9 , R 10 and R 11 are independently selected from hydrogen and deuterium;

Y is selected from X-A;

X is O;

A is H; and

at least one of R 3 , R 4 , R 5 and R 6 is deuterium and/or at least one of R 7 and R 8 comprises deuterium;

provided the compound of Formula I is not a compound wherein:

R 2 is hydrogen, R 3 , R 4 , R 5 and R 6 are all deuterium, R 9 , R 10 and R 11 are all hydrogen, and R 7 and R 8 are both CD 3 ; or

R 2 is hydrogen, R 3 , R 4 , R 5 and R 6 are all deuterium, R 9 , R 10 and R 11 are all hydrogen, and R 7 and R 8 are both CH 3 .

15. The compound of claim 14 , wherein R 9 , R 10 and R 11 are all hydrogen.

16. The compound of claim 15 , wherein:

R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium; or

R 7 and R 8 are both CH 3 or both CD 3 .

17. The compound of claim 16 , wherein R 2 is hydrogen, R 3 and R 4 are both deuterium; or R 5 and R 6 are both deuterium, R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium.

18. The compound of claim 16 , wherein R 2 is hydrogen, R 3 , R 4 , R 5 and R 6 are all deuterium, R 7 is selected from CH 3 and CD 3 and R 8 is hydrogen and the compound is selected from

or a pharmaceutically acceptable salt and/or solvate thereof.

19. The compound of claim 16 , wherein R 2 is hydrogen, and at least one of R 3 , R 4 , R 5 and R 6 is deuterium, and R 7 and R 8 are both CH 3 or both CD 3 , and the compound is selected from

or a pharmaceutically acceptable salt and/or solvate thereof.

20. The compound of claim 16 , wherein R 2 is hydrogen, R 3 and R 4 are both deuterium; or R 5 and R 6 are both deuterium, and R 7 and R 8 are both CH 3 or both CD 3 , and the compound is selected from

or a pharmaceutically acceptable salt and/or solvate thereof.

21. The compound of claim 16 , wherein R 2 is hydrogen, R 3 , R 4 , R 5 and R 6 are all hydrogen, R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium.

22. The compound of claim 16 , wherein R 2 is hydrogen, R 3 , R 4 , R 5 and R 6 are all hydrogen, and R 7 and R 8 are both CD 3 and the compound is

or a pharmaceutically acceptable salt and/or solvate thereof.

23. The compound of claim 14 , wherein R 9 , R 10 and R 11 are all deuterium.

24. The compound of claim 23 , wherein at least one of R 3 , R 4 , R 5 and R 6 is deuterium, and

R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium; or

R 7 and R 8 are both CH 3 or both CD 3 .

25. The compound of claim 23 , wherein R 3 and R 4 are both deuterium; or R 5 and R 6 are both deuterium; or R 3 , R 4 , R 5 and R 6 are all deuterium, and

R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium.

26. The compound of claim 14 , wherein R 2 is deuterium, R 3 and R 4 are both deuterium; or R 5 and R 6 are both deuterium, and R 7 and R 8 are both CH 3 or both CD 3 , and the compound is selected from

or a pharmaceutically acceptable salt and/or solvate thereof.

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

wherein

R 1 is hydrogen;

R 2 is selected from hydrogen and deuterium;

R 3 , R 4 , R 5 , and R 6 are independently selected from hydrogen and deuterium;

R 7 is selected from hydrogen, deuterium, CH 3 , and CD 3 ;

R 8 is selected from hydrogen, deuterium, CH 3 , and CD 3 ;

R 9 , R 10 , and R 11 are independently selected from hydrogen and deuterium, wherein at least one of R 9 , R 10 , and R 11 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 R 3 , R 4 , R 5 , and R 6 is deuterium; and/or

wherein at least one of R 7 and R 8 comprises deuterium.

28. The compound of claim 27 , wherein R 2 is deuterium, R 3 , R 4 , R 5 and R 6 are all deuterium, and R 7 and R 8 are both CD 3 and the compound is

or a pharmaceutically acceptable salt and/or solvate thereof.

29. A pharmaceutical composition comprising one or more compounds of claim 1 , or a pharmaceutically acceptable salt and/or solvate thereof, and a pharmaceutically acceptable carrier.

30. A method of treating a disease, disorder or condition treatable by activation of a serotonin receptor comprising administering a therapeutically effective amount of one or more compounds of claim 1 , or a pharmaceutically acceptable salt and/or solvate thereof to a subject in need thereof, wherein the disease, disorder or condition is selected from a mental illness, psychosis and psychotic symptoms, or wherein the disease, disorder or condition is selected from Alzheimer's disease, presenile dementia, senile dementia, vascular dementia, Lewy body dementia, cognitive impairment, Parkinson's disease, Parkinson dementia, corticobasal degeneration, supranuclear palsy, epilepsy, CNS trauma, CNS infections, CNS inflammation, stroke, multiple sclerosis, Huntington's disease, mitochondrial disorders, Fragile X syndrome, Angelman syndrome, hereditary ataxias, neuro-otological disorders, eye movement disorders, neurodegenerative diseases of the retina, amyotrophic lateral sclerosis, tardive dyskinesias, hyperkinetic disorders, attention deficit hyperactivity disorder, attention deficit disorders, restless leg syndrome, Tourette's syndrome, schizophrenia, autism spectrum disorders, tuberous sclerosis, Rett syndrome, cerebral palsy, eating disorders, trichotillomania, dermotillomania, nail biting, migraine, fibromyalgia, and peripheral neuropathy of any etiology, and combinations thereof.

31. The compound of claim 14 , wherein the compound is:

32. A pharmaceutical composition comprising one or more compounds of claim 14 , or a pharmaceutically acceptable salt and/or solvate thereof, and a pharmaceutically acceptable carrier.

33. A method of treating a disease, disorder or condition treatable by activation of a serotonin receptor comprising administering a therapeutically effective amount of one or more compounds of claim 14 , or a pharmaceutically acceptable salt and/or solvate thereof to a subject in need thereof, wherein the disease, disorder or condition is selected from a mental illness, psychosis and psychotic symptoms, or wherein the disease, disorder or condition is selected from Alzheimer's disease, presenile dementia, senile dementia, vascular dementia, Lewy body dementia, cognitive impairment, Parkinson's disease, Parkinson dementia, corticobasal degeneration, supranuclear palsy, epilepsy, CNS trauma, CNS infections, CNS inflammation, stroke, multiple sclerosis, Huntington's disease, mitochondrial disorders, Fragile X syndrome, Angelman syndrome, hereditary ataxias, neuro-otological disorders, eye movement disorders, neurodegenerative diseases of the retina, amyotrophic lateral sclerosis, tardive dyskinesias, hyperkinetic disorders, attention deficit hyperactivity disorder, attention deficit disorders, restless leg syndrome, Tourette's syndrome, schizophrenia, autism spectrum disorders, tuberous sclerosis, Rett syndrome, cerebral palsy, eating disorders, trichotillomania, dermotillomania, nail biting, migraine, fibromyalgia, and peripheral neuropathy of any etiology, and combinations thereof.

34. A pharmaceutical composition comprising one or more compounds of claim 27 , or a pharmaceutically acceptable salt and/or solvate thereof, and a pharmaceutically acceptable carrier.

35. A method of treating a disease, disorder or condition treatable by activation of a serotonin receptor comprising administering a therapeutically effective amount of one or more compounds of claim 27 , or a pharmaceutically acceptable salt and/or solvate thereof to a subject in need thereof, wherein the disease, disorder or condition is selected from a mental illness, psychosis and psychotic symptoms, or wherein the disease, disorder or condition is selected from Alzheimer's disease, presenile dementia, senile dementia, vascular dementia, Lewy body dementia, cognitive impairment, Parkinson's disease, Parkinson dementia, corticobasal degeneration, supranuclear palsy, epilepsy, CNS trauma, CNS infections, CNS inflammation, stroke, multiple sclerosis, Huntington's disease, mitochondrial disorders, Fragile X syndrome, Angelman syndrome, hereditary ataxias, neuro-otological disorders, eye movement disorders, neurodegenerative diseases of the retina, amyotrophic lateral sclerosis, tardive dyskinesias, hyperkinetic disorders, attention deficit hyperactivity disorder, attention deficit disorders, restless leg syndrome, Tourette's syndrome, schizophrenia, autism spectrum disorders, tuberous sclerosis, Rett syndrome, cerebral palsy, eating disorders, trichotillomania, dermotillomania, nail biting, migraine, fibromyalgia, and peripheral neuropathy of any etiology, and combinations thereof.

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

wherein

R 1 is hydrogen;

R 2 is selected from hydrogen and deuterium;

R 3 , R 4 , R 5 , and R 6 are independently selected from hydrogen and deuterium;

R 7 is selected from hydrogen, deuterium, CH 32 and CD 3 ;

R 8 is selected from hydrogen, deuterium, CH 3 , and CD 3 ;

R 9 , R 10 , and R 11 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 R 3 , R 4 , R 5 , and R 6 is deuterium; or

at least one of R 7 and R 8 comprises deuterium; or

at least one of R 3 , R 4 , R 5 , and R 6 is deuterium and at least one of R 7 and R 8 comprises deuterium; and

wherein:

R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium; or

at least one of R 3 , R 4 , R 5 , and R 6 is H; or

R 7 is selected from CH 3 and CD 3 , R 8 is selected from hydrogen and deuterium, and at least one of R 3 , R 4 , R 5 , and R 6 is H.

37. The compound of claim 36 , wherein R 9 , R 10 and R 11 are all hydrogen.

38. The compound of claim 37 , wherein:

R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium; or

R 7 and R 8 are both CH 3 or both CD 3 .

39. The compound of claim 38 , wherein R 2 is hydrogen, and R 3 and R 4 are both deuterium; or R 5 and R 6 are both deuterium, R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium.

40. The compound of claim 38 , wherein R 2 is hydrogen, R 3 , R 4 , R 5 and R 6 are all hydrogen, R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium.

41. The compound of claim 36 , wherein R 9 , R 10 and R 11 are all deuterium.

42. The compound of claim 41 , wherein at least one of R 3 , R 4 , R 5 and R 6 is deuterium, and

R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium; or

R 7 and R 8 are both CH 3 or both CD 3 .

43. The compound of claim 41 , wherein R 3 and R 4 are both deuterium; or R 5 and R 6 are both deuterium; or R 3 , R 4 , R 5 and R 6 are all deuterium, and

R 7 is selected from CH 3 and CD 3 and R 8 is selected from hydrogen and deuterium.

44. A pharmaceutical composition comprising one or more compounds of claim 36 , or a pharmaceutically acceptable salt and/or solvate thereof, and a pharmaceutically acceptable carrier.

45. A method of treating a disease, disorder or condition treatable by activation of a serotonin receptor comprising administering a therapeutically effective amount of one or more compounds of claim 38 , or a pharmaceutically acceptable salt and/or solvate thereof to a subject in need thereof, wherein the disease, disorder or condition is selected from a mental illness, psychosis and psychotic symptoms, or wherein the disease, disorder or condition is selected from Alzheimer's disease, presenile dementia, senile dementia, vascular dementia, Lewy body dementia, cognitive impairment, Parkinson's disease, Parkinson dementia, corticobasal degeneration, supranuclear palsy, epilepsy, CNS trauma, CNS infections, CNS inflammation, stroke, multiple sclerosis, Huntington's disease, mitochondrial disorders, Fragile X syndrome, Angelman syndrome, hereditary ataxias, neuro-otological disorders, eye movement disorders, neurodegenerative diseases of the retina, amyotrophic lateral sclerosis, tardive dyskinesias, hyperkinetic disorders, attention deficit hyperactivity disorder, attention deficit disorders, restless leg syndrome, Tourette's syndrome, schizophrenia, autism spectrum disorders, tuberous sclerosis, Rett syndrome, cerebral palsy, eating disorders, trichotillomania, dermotillomania, nail biting, migraine, fibromyalgia, and peripheral neuropathy of any etiology, and combinations thereof.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 31, 2024

From: SLASSI, ABDELMALIK; ARAUJO, JOSEPH

To: MINDSET PHARMA INC.

Reel/Frame 067564/0984 →

Continuity (6)

Continuation 18109890 · Feb 15, 2023

Continuation 17743718 · May 13, 2022

Division 17387845 · Jul 28, 2021

Continuation PCTCA2021050123 · Feb 4, 2021

Provisional Application 62969934 · Feb 4, 2020

Related Publication 20240317782A1 · Sep 26, 2024

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Pichini, Simona et al., “Liquid chromatography-atmospheric pressure ionization electrospray mass spectrometry determination of ‘hallucinogenic designer drugs’ in urine of consumers,” Journal of Pharmaceutical and Biomed… [cited by applicant]

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