Granted Patent B2

US 12,344,570 · App. 18/454,711 · Granted Jul 1, 2025

Inventors: Glenn Short (Scituate, MA); Robert B. Perni (Marlborough, MA); Tanweer A. Khan (Bridgewater, NJ)

Assignee: Atai Therapeutics, Inc.

C07C211/42C07D217/08

Abstract

Claims (35)

1. A compound of Formula (III):

or a pharmaceutically acceptable salt thereof; wherein,

R 1 is methyl;

R 2 and R 3 are independently H, C 1 -C 6 alkyl, halogen, CN, or OR 7 ;

R 4 and R 5 are H;

R 7 is H, C 1 -C 6 alkyl, or C 1 -C 6 fluoroalkyl; and

X is CH or N;

wherein the compound is not 5,8-dimethoxy-6-methyl-1,2,3,4-tetrahydronaphthalen-2-amine; 5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine; 6-bromo-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine; 7-bromo-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine; 5,7,8-trimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine;

or 5,6,8-trimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine.

2. The compound of claim 1 , wherein R 2 is H, F, Cl, I, or CN.

3. The compound of claim 1 , wherein R 3 is H, F, Cl, I, or CN.

4. A compound of Formula (IV):

or a pharmaceutically acceptable salt thereof; wherein,

R 1 is independently H or C 1 -C 6 alkyl;

R 3 is H, C 1 -C 6 alkyl, halogen, CN, OR 7 or SR 1 ;

R 4 and R 5 are independently H or C 1 -C 6 alkyl;

R 6 and R 7 are independently H or C 1 -C 6 alkyl;

X is CH or N;

Y is =O or ═NH;

m is 0, 1, 2 or 3; and

n is 0, 1, 2 or 3.

5. The compound of claim 4 , wherein Y is =O.

6. The compound of claim 4 , wherein R 1 is C 1 -C 6 alkyl.

7. The compound of claim 4 , wherein R 3 is H or halogen.

8. The compound of claim 4 , wherein R 4 is H or C 1 -C 6 alkyl.

9. The compound of claim 4 , wherein R 5 is H or C 1 -C 6 alkyl.

10. The compound of claim 4 , wherein X is CH.

11. The compound of claim 4 , wherein m is 0 or 1.

12. The compound of claim 4 , wherein n is 1 or 2.

13. The compound of claim 4 , wherein R 6 is H or methyl.

14. A compound selected from:

15. A pharmaceutical composition, comprising a compound of claim 1 and a pharmaceutically acceptable excipient.

16. A method of treating a mental health disease or disorder, the method comprising administering a therapeutically effective amount of the composition of claim 15 .

17. A pharmaceutical composition, comprising a compound of claim 4 and a pharmaceutically acceptable excipient.

18. A method of treating a mental health disease or disorder, the method comprising administering a therapeutically effective amount of the composition of claim 17 .

Assignments (6)

Continuity (3)

References Cited (164)