US 12,454,516 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., New York, NY (US)
Filed by EmpathBio, Inc., Encinitas, CA (US)
Filed on Jan. 29, 2024, as Appl. No. 18/426,035.
Application 18/426,035 is a continuation of application No. 18/147,189, filed on Dec. 28, 2022, granted, now 11,912,680.
Claims priority of provisional application 63/294,225, filed on Dec. 28, 2021.
Prior Publication US 2024/0400532 A1, Dec. 5, 2024
This patent is subject to a terminal disclaimer.
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 method of treating social anxiety in a subject in need thereof, the method comprising administering to the subject an effective amount of 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.