US 12,240,813 B2
Deuterated tryptamine derivatives and methods of use
Alex Nivorozhkin, West Roxbury, MA (US); and Michael Palfreyman, St. Petersburg, FL (US)
Assigned to Cybin IRL Limited, Dublin (IE)
Appl. No. 17/999,310
Filed by CYBIN IRL LIMITED, Dublin (IE)
PCT Filed May 19, 2021, PCT No. PCT/IB2021/054340
§ 371(c)(1), (2) Date Nov. 18, 2022,
PCT Pub. No. WO2021/234608, PCT Pub. Date Nov. 25, 2021.
Claims priority of provisional application 63/157,118, filed on Mar. 5, 2021.
Claims priority of provisional application 63/114,738, filed on Nov. 17, 2020.
Claims priority of provisional application 63/026,939, filed on May 19, 2020.
Prior Publication US 2023/0219889 A1, Jul. 13, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 209/16 (2006.01); A61K 9/20 (2006.01); A61K 31/4045 (2006.01)
CPC C07D 209/16 (2013.01) [A61K 9/20 (2013.01); A61K 9/2054 (2013.01); A61K 31/4045 (2013.01); C07B 2200/05 (2013.01); C07B 2200/07 (2013.01)] 20 Claims
 
1. A compound of Formula (I),

OG Complex Work Unit Chemistry
or an optically pure stereoisomer, pharmaceutically acceptable salt, solvate, or prodrug thereof,
wherein:
X1 and X2 are deuterium;
Y1 and Y2 are deuterium;
R is

OG Complex Work Unit Chemistry
R2 is selected from hydrogen, deuterium, unsubstituted or substituted alkyl, unsubstituted or substituted allyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl;
R4 is hydrogen or deuterium;
R5 is selected from hydrogen, deuterium, and unsubstituted or substituted alkoxy;
R6 is selected from hydrogen, deuterium, and halogen;
R7 is selected from hydrogen, deuterium, and halogen;
R8 is an alkyl substituted with one or more deuterium;
R9 is an alkyl substituted with one or more deuterium; and
R10 is selected from hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted allyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl;
wherein at least one of R6 and R7 is halogen.