US 11,999,694 B2
Delivery of therapeutic alkaloid compounds
Jacob M. Hooker, Winchester, MA (US); and Michael S. Placzek, Waltham, MA (US)
Assigned to Sensorium Therapeutics, Inc., Boston, MA (US)
Filed by Sensorium Therapeutics, Inc., Boston, MA (US)
Filed on Oct. 28, 2022, as Appl. No. 17/976,150.
Claims priority of provisional application 63/352,810, filed on Jun. 16, 2022.
Claims priority of provisional application 63/273,688, filed on Oct. 29, 2021.
Prior Publication US 2023/0159455 A1, May 25, 2023
Int. Cl. C07D 209/12 (2006.01); C07D 401/12 (2006.01); C07D 405/12 (2006.01); C07D 409/12 (2006.01); C07D 475/04 (2006.01); C07D 491/113 (2006.01); C07D 491/20 (2006.01); C07D 495/04 (2006.01); C07D 495/10 (2006.01); C07D 497/10 (2006.01); C07D 498/10 (2006.01); C07D 519/00 (2006.01); C07F 7/18 (2006.01)
CPC C07D 209/12 (2013.01) [C07D 401/12 (2013.01); C07D 405/12 (2013.01); C07D 409/12 (2013.01); C07D 475/04 (2013.01); C07D 491/113 (2013.01); C07D 491/20 (2013.01); C07D 495/04 (2013.01); C07D 495/10 (2013.01); C07D 497/10 (2013.01); C07D 498/10 (2013.01); C07D 519/00 (2013.01); C07F 7/1804 (2013.01)] 21 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein
R1is or C1-C7alkyl or H; and
ring A

OG Complex Work Unit Chemistry
wherein * denotes the attachment points of ring A to the compound of formula (I), and wherein
R3 is —OSi(C1-C6 alkyl)3, —OC(O)C1-C6 alkyl, —OC(O)C2-C6 alkenyl, —OC(O)C3-C10 cycloalkyl, —OC(O)phenyl, —OC(O)-5- to 7-membered heteroaryl, wherein each hydrogen atom in C1-C6 alkyl, C2-C6 alkenyl, C3-C10 cycloalkyl, phenyl, and 5- to 7-membered heteroaryl is optionally substituted by halogen, C1-C6 alkyl, C1-C3 alkoxy, nitro, —N(C1-C3 alkyl)2, C1-C3 haloalkyl, cyano, phenyl, phenoxy or —O(CH2)pOCH3; and
p is 2, 3, or 4.