IP Library › Granted Patent US 12,606,525

Granted Patent B2

US 12,606,525 · App. 18/657,306 · Granted Apr 21, 2026

Dimethyltryptamine analogues as nitric oxide delivery drugs

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

Assignee: Atai Therapeutics, Inc.

C07D209/16 C07B2200/05

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Quick Facts

Patent No.: US 12,606,525
App. No.: 18/657,306
Granted: Apr 21, 2026
Kind: B2

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Abstract

Provided herein are compounds of Formula (I), (II), or a pharmaceutically acceptable salt thereof. Also provided herein are pharmaceutical compositions comprising a compound of Formula (I), (II), or pharmaceutically acceptable salt thereof, and methods of using a compound of Formula (I), (II), or a pharmaceutically acceptable salt thereof.

Claims (46)

1 . A method of treating a mental health disease or disorder, the method comprising administering to a subject in need thereof a compound of Formula (II):

or a pharmaceutically acceptable salt thereof; wherein,

R 3 , R 4 , and R 5 are independently H, halogen, or C 1 -C 6 alkyl;

R 6 is —(C═O)(CR 7 R 7 ′) n —ONO 2 , or —(C═O)(CR 7 R 7 ′) m —CH(NH 2 )CH 2 ONO 2 ;

R 1 and R 2 are each independently H or C 1 -C 6 alkyl; and

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

X, Y, and Z are independently absent or O;

m is 2, 3, or 4; and

each n is independently 1, 2, 3, 4 or 5.

2 . The method of claim 1 , wherein R 1 is C 1 -C 6 alkyl.

3 . The method of claim 1 , wherein R 1 is methyl.

4 . The method of claim 1 , wherein R 1 is H.

5 . The method of claim 1 , wherein R 2 is C 1 -C 6 alkyl.

6 . The method of claim 1 , wherein R 2 is methyl.

7 . The method of claim 1 , wherein R 2 is H.

8 . The method of claim 1 , wherein R 3 is H and X is absent.

9 . The method of claim 1 , wherein R 3 is halogen and X is absent.

10 . The method of claim 1 , wherein R 3 is H and X is O.

11 . The method of claim 1 , wherein R 3 is C 1 -C 6 alkyl and X is O.

12 . The method of claim 1 , wherein R 4 is H and Y is absent.

13 . The method of claim 1 , wherein R 4 is H and Y is O.

14 . The method of claim 1 , wherein R 4 is halogen and Y is absent.

15 . The method of claim 1 , wherein R 4 is C 1 -C 6 alkyl and Y is O.

16 . The method of claim 1 , wherein R 5 is H and Z is absent.

17 . The method of claim 1 , wherein R 5 is H and Z is O.

18 . The method of claim 1 , wherein R 5 is halogen and Z is absent.

19 . The method of claim 1 , wherein R 5 is C 1 -C 6 alkyl and Z is absent.

20 . The method of claim 1 , wherein R 5 is C 1 -C 6 alkyl and Z is O.

21 . The method of claim 1 , wherein R 6 is —(C═O)(CR 7 R 7 ′) n —ONO 2 .

22 . The method of claim 1 , wherein R 6 is —(C═O)(CR 7 R 7 ′) m —CH(NH 2 )CH 2 ONO 2 .

23 . The method of claim 1 , wherein R 6 is —(C═O)(CH 2 ) n —ONO 2 .

24 . The method of claim 1 , wherein R 6 is —(C═O)(CH 2 ) m —CH(NH 2 )CH 2 ONO 2 .

25 . The method of claim 1 , wherein R 6 is —(C═O)(CH 2 ) 3 —ONO 2 .

26 . The method of claim 1 , wherein the compound has the following chemical formula:

or a pharmaceutically acceptable salt thereof.

27 . The method of claim 26 , wherein the compound has the following chemical formula:

or a pharmaceutically acceptable salt thereof.

28 . The method of claim 26 , wherein the compound has the following chemical formula:

or a pharmaceutically acceptable salt thereof.

29 . The method of claim 1 . wherein the compound is administered in a pharmaceutical composition comprising a pharmaceutically acceptable excipient.

30 . A method of treating a mental health disease or disorder, the method comprising administering a therapeutically effective amount of a compound having the following formula:

or a pharmaceutically acceptable salt thereof.

31 . The method of claim 1 , wherein the mental health disease or disorder the mental is selected from the group consisting of major depressive disorder, treatment resistant depression, a substance use disorder, an eating disorder, a compulsive disorder, an anxiety disorder, and rumination.

32 . The method of claim 31 , wherein the eating disorder is anorexia nervosa, bulimia nervosa, or binge eating disorder.

33 . The method of claim 30 , wherein the mental health disease or disorder the mental is selected from the group consisting of major depressive disorder, treatment resistant depression, a substance use disorder, an eating disorder, a compulsive disorder, an anxiety disorder, and rumination.

34 . The method of claim 33 , wherein the eating disorder is anorexia nervosa, bulimia nervosa, or binge eating disorder.

Assignments (6)