US 12,134,602 B2
(−)-huperzine A processes and related compositions and methods of treatment
Seth Herzon, New Haven, CT (US); and Maung Kyaw Moe Tun, New Haven, CT (US)
Assigned to YALE UNIVERSITY, New Haven, CT (US)
Filed by Yale University, New Haven, CT (US)
Filed on Sep. 23, 2021, as Appl. No. 17/482,996.
Application 17/482,996 is a division of application No. 16/892,828, filed on Jun. 4, 2020, granted, now 11,142,503.
Application 16/892,828 is a division of application No. 16/571,720, filed on Sep. 16, 2019, granted, now 10,781,179, issued on Sep. 2, 2020.
Application 16/571,720 is a division of application No. 15/848,350, filed on Dec. 20, 2017, granted, now 10,457,643, issued on Oct. 29, 2019.
Application 15/848,350 is a division of application No. 14/003,213, granted, now 10,059,672, issued on Aug. 28, 2018, previously published as PCT/US2012/025628, filed on Feb. 17, 2012.
Claims priority of provisional application 61/449,198, filed on Mar. 4, 2011.
Prior Publication US 2022/0064123 A1, Mar. 3, 2022
Int. Cl. C07D 221/22 (2006.01); A61K 31/439 (2006.01); C07F 7/10 (2006.01)
CPC C07D 221/22 (2013.01) [A61K 31/439 (2013.01); C07F 7/10 (2013.01)] 2 Claims
OG exemplary drawing
 
1. A compound of the formula (I):

OG Complex Work Unit Chemistry
wherein:
R1 is selected from the group consisting of substituted or unsubstituted C1-C6 alkyl and substituted or unsubstituted ether;
R2 and R5 are independently selected from the group consisting of H, substituted or unsubstituted C1-C6 alkyl, and CN, provided that when one of R2 or R5 is CN, the other must be H;
X is halogen;
R3 at each occurrence is independently selected from the group consisting of H, substituted or unsubstituted C1-C6 alkyl, ether, amino, and alkoxy;
R4 is selected from the group consisting of Si(CH3)2Ph, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkenyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;
A is CH or N;
m is 0, 1, or 2;
or a pharmaceutically acceptable salt, enantiomer, diastereomer, solvate or polymorph thereof.