US 12,065,405 B2
Prodrugs and conjugates of dimethyltryptamine
Robert B. Perni, Marlborough, MA (US); Glenn Short, Scituate, MA (US); Srinivas G. Rao, Encinitas, CA (US); and Tanweer A. Khan, Bridgewater, NJ (US)
Assigned to ATAI Therapeutics, Inc., New York, NY (US)
Filed by ATAI Therapeutics, Inc., New York, NY (US)
Filed on Apr. 12, 2023, as Appl. No. 18/299,347.
Application 18/299,347 is a continuation of application No. 17/889,013, filed on Aug. 16, 2022, granted, now 11,643,391.
Application 17/889,013 is a continuation of application No. 17/836,984, filed on Jun. 9, 2022, abandoned.
Claims priority of provisional application 63/229,879, filed on Aug. 5, 2021.
Claims priority of provisional application 63/208,874, filed on Jun. 9, 2021.
Prior Publication US 2023/0357146 A1, Nov. 9, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 209/16 (2006.01); C07D 209/08 (2006.01); C07D 209/12 (2006.01); C07D 209/14 (2006.01); C07D 401/06 (2006.01); C07D 403/06 (2006.01); C07F 9/572 (2006.01)
CPC C07D 209/16 (2013.01) [C07D 209/08 (2013.01); C07D 209/12 (2013.01); C07D 209/14 (2013.01); C07D 401/06 (2013.01); C07D 403/06 (2013.01); C07F 9/5728 (2013.01)] 30 Claims
 
1. A compound of Formula:

OG Complex Work Unit Chemistry
wherein R1 and R2 are independently hydrogen, alkyl, or cycloalkyl; or R1 and R2, together with the atoms to which they are attached form a heterocyclic ring;
X, Y, and Z are independently hydrogen, halogen, —O—, —S—, —NRA—, or (P═O)—ORA(—OR′), wherein R′ and RA are independently hydrogen or alkyl;
R3, R4, and R5 are independently absent, —(C═O)CHR7(NH2), —(C═O)CH(NH2)(CH2)n(NH2), or —(C═O)CH(NH2)(CH2)n(NH)(C═NH)(NH2);
R7 is hydrogen or alkyl;
R9 is hydrogen, alkyl, or halogen;
R11 is a pharmaceutically acceptable cation, hydrogen, deuterium, alkyl, or cycloalkyl; and
n is an integer from 2-7.