Granted Patent B2

US 12,251,371 · App. 18/163,388 · Granted Mar 18, 2025

Inventors: Peter Rands (London, GB); Ellen James (London, GB); Tiffanie Benway (London, GB); Zelah Joel (London, GB); Marie Layzell (London, GB)

Assignee: Cybin UK Ltd.

A61K31/4045C07D209/16

Abstract

Claims (26)

1. A compound of formula (I):

wherein:

n is 1, and wherein R 1 is 5-methoxy or 5-bromo;

R 2 is CD 3 ;

R 3 is CD 3 or H;

and

each y H is deuterium;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is 5-methoxy.

3. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein both R 2 and R 3 are CD 3 .

4. The compound of claim 1 , in the form of a pharmaceutically acceptable salt.

5. The compound of claim 1 , wherein the pharmaceutically acceptable salt is a fumarate salt.

6. The compound of claim 2 , wherein the compound has a molecular weight from 224.3 to 226.4 grams per mole as the free base.

7. A composition comprising a compound as defined in claim 1 , or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable excipient.

8. A method of treating a psychiatric or neurological disorder in a patient, comprising administering to the patient a therapeutically effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

9. The method according to claim 8 , wherein the psychiatric or neurological disorder is selected from (i) an obsessive compulsive disorder, (ii) a depressive disorder, (iii) a schizophrenia disorder, (iv) a schizotypal disorder, (v) an anxiety disorder, (vi) substance abuse, and (vii) an avolition disorder.

10. The method according to claim 8 , wherein the disorder is major depressive disorder, or treatment resistant depression.

11. The method according to claim 8 , wherein said administering is oral administration of the compound or salt.

12. The compound of claim 1 , which is 5-methoxy-α,α,bis-deutero-N,N-di(trideuteromethyl)tryptamine, or a pharmaceutically acceptable salt thereof.

13. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is 5-bromo.

14. The compound of claim 2 , or a pharmaceutically acceptable salt thereof, wherein both R 2 and R 3 are CD 3 .

15. The compound of claim 13 , or a pharmaceutically acceptable salt thereof, wherein both R 2 and R 3 are CD 3 .

16. The compound of claim 2 , in the form of a pharmaceutically acceptable salt.

17. The compound of claim 13 , in the form of a pharmaceutically acceptable salt.

18. The compound of claim 2 , wherein the pharmaceutically acceptable salt is a fumarate salt.

19. The compound of claim 13 , wherein the pharmaceutically acceptable salt is a fumarate salt.

Assignments (2)

Priority Claims (6)

Continuity (3)

References Cited (114)