US 12,012,381 B2
Dimethyltryptamine analogues as nitric oxide delivery drugs
Robert B. Perni, Marlborough, MA (US); Glenn Short, Scituate, MA (US); and Tanweer A. Khan, Bridgewater, NJ (US)
Assigned to ATAI THERAPEUTICS, INC., Encinitas, CA (US)
Filed by ATAI Therapeutics, Inc., New York, NY (US)
Filed on Dec. 28, 2022, as Appl. No. 18/147,499.
Claims priority of provisional application 63/295,199, filed on Dec. 30, 2021.
Prior Publication US 2023/0227407 A1, Jul. 20, 2023
Int. Cl. C07D 209/16 (2006.01)
CPC C07D 209/16 (2013.01) [C07B 2200/05 (2013.01)] 33 Claims
 
1. A compound of Formula (II):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof; wherein,
R3, R4, and R5 are independently H, halogen, or C1-C6 alkyl;
R6 is —(C═O)(CR7R7′)n—ONO2,
or —(C═O)(CR7R7′)m—CH(NH2)CH2ONO2;
R1 and R2 are independently H or C1-C6 alkyl;
R7 and R7′ are independently H, halogen, or C1-C6 alkyl;
X, Y, and Z are independently absent or O;
each m is 2, 3, or 4; and
each n is independently 1, 2, 3, 4 or 5.