US 11,912,680 B2
Nitric oxide releasing prodrugs of MDA and MDMA
Robert B. Perni, Marlborough, MA (US); Glenn Short, Scituate, MA (US); and Tanweer A. Khan, Bridgewater, NJ (US)
Assigned to EmpathBio, Inc., Encinitas, CA (US)
Filed by ATAI Life Sciences AG, Berlin (DE)
Filed on Dec. 28, 2022, as Appl. No. 18/147,189.
Claims priority of provisional application 63/294,225, filed on Dec. 28, 2021.
Prior Publication US 2023/0227421 A1, Jul. 20, 2023
Int. Cl. C07D 307/79 (2006.01); C07D 317/58 (2006.01); C07D 319/18 (2006.01)
CPC C07D 317/58 (2013.01) [C07D 307/79 (2013.01); C07D 319/18 (2013.01)] 62 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof; wherein,
R1 is —(C═O)(CR9R9′)n—ONO2 or —(C═O)(CR9R9′)m—CH(NH2)CH2ONO2;
R2 is H, C1-C4 alkyl, or CF3;
R3 and R4 are independently H or F;
R5 and R6 are independently H, C1-C6 alkyl, or CF3;
R7 is H or CH3;
R8 is H, C1-C6 alkyl, or CF3;
R9 and R9′ are independently H, halogen, or C1-C6 alkyl;
X and Y are independently H, F, Cl, Br, or OR8;
n is an integer from 1 to 9; and
m is an integer from 1 to 9.