US 11,866,408 B2
N,N-dimethyltryptamine and related psychedelics and uses thereof
Matthew Alexander James Duncton, San Bruno, CA (US); and Sam Clark, New York, NY (US)
Assigned to TERRAN BIOSCIENCES INC., New York, NY (US)
Filed by Terran Biosciences Inc., New York, NY (US)
Filed on Feb. 23, 2023, as Appl. No. 18/173,717.
Application 18/173,717 is a continuation of application No. PCT/US2022/036396, filed on Jul. 7, 2022.
Claims priority of provisional application 63/276,516, filed on Nov. 5, 2021.
Claims priority of provisional application 63/219,312, filed on Jul. 7, 2021.
Prior Publication US 2023/0212119 A1, Jul. 6, 2023
Int. Cl. C07D 209/32 (2006.01); C07D 209/12 (2006.01); C07D 209/14 (2006.01)
CPC C07D 209/32 (2013.01) [C07D 209/12 (2013.01); C07D 209/14 (2013.01)] 28 Claims
 
1. A compound of Formula (I), or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein:
R1 is methoxy or hydrogen;
R2 is —C(O)R4, —C(O)OCH(R5)OC(O)OR6,

OG Complex Work Unit Chemistry
R4 is alkyl, which is substituted with —N(R18)R19;
R5 is hydrogen, alkyl, or cycloalkyl;
R6 is alkyl, cycloalkyl, or —CH(RA1)NH2;
RA1 is alkyl or an amino acid side chain;
RA5 is —N(R18)R19 or —N(R13)C(O)R14;
R13 is hydrogen; R14 is alkyl;
R15 is alkyl, heteroalkyl, cycloalkyl, aryl, or heteroaryl, each of which is unsubstituted or substituted with one or more RB; and
each of R18 and R19 is independently hydrogen or alkyl.