Granted Patent B2

US 12,318,477 · App. 18/056,771 · Granted Jun 3, 2025

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

Assignee: Cybin UK Ltd

A61K9/0019A61K9/19A61K31/4045A61K45/06

Abstract

Claims (38)

1. A pharmaceutical formulation suitable for intramuscular injection, comprising a salt of a compound of Formula IB:

wherein:

n is 0;

R 1b is independently selected from —R 4b , —OH, —OR 4b , —O(CO)R 4b , monohydrogen phosphate, —F, —Cl, —Br or —I;

R 2b is C( xb H) 3 ;

R 3b is C( xb H) 3 ;

each R 4b is independently selected from C 1 -C 4 alkyl; and

each xb H, yb H and z H is independently selected from protium or deuterium;

and a Brønsted acid having a pKa of from about 3 to about 5;

a base agent, water, and optionally a buffer which is separate to the salt;

wherein the formulation has a pH of from about 5 to about 6.5, a concentration of the compound of Formula IB of about 10 mg/ml or greater as the freebase equivalent, and an osmolality of from about 250 to about 350 mOsm/Kg; and

wherein the formulation comprises a dose of the compound of Formula IB within a volume of 5 ml or less.

2. The formulation of claim 1 , wherein the formulation has a pH of from about 5 to about 6.

3. The formulation of claim 1 , wherein the formulation comprises a dose of the compound of Formula IB within a volume of 3 ml or less.

4. The formulation of claim 1 , wherein R 2b is CD 3 and R 3b is CD 3 ; and/or wherein each yb H is D.

5. The formulation of claim 1 , wherein the compound of Formula IB is N,N-dimethyltryptamine.

6. The formulation of claim 1 , wherein the compound of Formula IB is selected from the group consisting of α,α-dideutero-N,N-dimethyltryptamine, α,α-dideutero-N,N-di(trideuteromethyl)tryptamine, α,α,β,β-tetradeutero-N,N-dimethyltryptamine, and α,α,β,β-tetradeutero-N,N-di(trideuteromethyl)tryptamine.

7. The formulation of claim 1 , wherein the Brønsted acid is selected from the group consisting of fumaric acid, tartaric acid, citric acid, acetic acid, lactic acid and gluconic acid.

8. The formulation of claim 1 , wherein the concentration of the compound of Formula IB is from about 20 mg/mL to about 40 mg/mL (as the freebase equivalent).

9. The formulation of claim 1 , wherein the formulation comprises the buffer which is separate to the salt, optionally wherein the buffer comprises an acetate salt and acetic acid; or a citrate salt and citric acid; or a phosphate salt and phosphoric acid; or the buffer comprises an acetate salt, a citrate salt, or a phosphate salt.

10. The formulation of claim 1 , wherein the formulation further comprises a tonicity agent and/or a pH adjuster.

11. The formulation of claim 1 , wherein the formulation consists of the salt of the compound of Formula IB, water, the base agent and optionally the buffer and/or a tonicity agent and/or pH adjuster.

12. The formulation of claim 1 , having an oxygen content of less than 5 ppm, or less than 2 ppm.

13. The formulation of claim 1 , comprising the salt of the compound of Formula IB, the base agent, water, the buffer which is separate to the salt, and a tonicity agent or pH adjuster.

14. The formulation of claim 13 , comprising a salt of the compound of Formula IB; the base agent which is selected from potassium hydroxide or sodium hydroxide; water; the buffer which is a citrate salt; and the tonicity agent or pH adjuster which is an acid.

15. A kit suitable for preparing the formulation of claim 1 , said kit comprising the salt of the compound of Formula IB; optionally a tonicity agent and/or a pH adjuster; the base agent and optionally the buffer which is separate to the salt.

16. A lyophilised powder formulation comprising the formulation according to claim 1 which has been lyophilised.

17. The formulation of claim 1 , wherein the concentration of the compound of Formula IB is about 25 mg/mL (as the freebase equivalent).

18. The formulation of claim 1 , wherein the compound of Formula IB is a deuterated N,N-dimethyltryptamine.

19. The formulation of claim 18 , wherein the deuterated N,N-dimethyltryptamine is selected from the group consisting of α,α-dideutero-N,N-dimethyltryptamine, α,α-dideutero-N,N-di(trideuteromethyl)tryptamine, α,α,β,β-tetradeutero-N,N-dimethyltryptamine, and α,α,β,β-tetradeutero-N,N-di(trideuteromethyl)tryptamine.

20. A pharmaceutical formulation suitable for intramuscular injection, comprising:

a fumarate salt of deuterated N,N-dimethyltryptamine selected from the group consisting of α,α-dideutero-N,N-dimethyltryptamine, α,α-dideutero-N,N-di(trideuteromethyl)tryptamine, α,α,β,β-tetradeutero-N,N-dimethyltryptamine, and α,α,β,β-tetradeutero-N,N-di(trideuteromethyl)tryptamine;

a base agent selected from potassium hydroxide and sodium hydroxide;

water; and

a buffer which comprises an acetate salt, a citrate salt, or a phosphate salt;

wherein the formulation has a pH of from about 5 to about 6.5, a concentration of the deuterated N,N-dimethyltryptamine from about 20 mg/mL to about 40 mg/mL as the freebase equivalent, and an osmolality of from about 250 to about 350 mOsm/Kg; and

wherein the formulation comprises a dose of the deuterated N,N-dimethyltryptamine within a volume of 5 ml or less.

21. A formulation according to claim 20 , comprising a fumarate salt of α,α,β,β-tetradeutero-N,N-di(trideuteromethyl)tryptamine.

Assignments (2)

Priority Claims (4)

Continuity (1)

References Cited (130)