US 12,071,409 B2
Quinoline derived small molecule inhibitors of nicotinamide N-methyltransferase (NNMT) and uses thereof
Stanley Watowich, Galveston, TX (US); Harshini Neelakantan, Galveston, TX (US); Hua-Yu Wang, Galveston, TX (US); and Stanton Mchardy, Galveston, TX (US)
Assigned to The Board of Regents of the University of Texas, Austin, TX (US)
Filed by The Board of Regents of the University of Texas System, Austin, TX (US)
Filed on Jun. 7, 2022, as Appl. No. 17/834,847.
Application 17/834,847 is a continuation of application No. 16/499,228, granted, now 11,401,243, previously published as PCT/US2018/025134, filed on Mar. 29, 2018.
Claims priority of provisional application 62/559,417, filed on Sep. 15, 2017.
Claims priority of provisional application 62/479,256, filed on Mar. 30, 2017.
Prior Publication US 2023/0107256 A1, Apr. 6, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 215/42 (2006.01); C07D 215/10 (2006.01); C07D 215/26 (2006.01); C07D 405/06 (2006.01)
CPC C07D 215/42 (2013.01) [C07D 215/10 (2013.01); C07D 215/26 (2013.01); C07D 405/06 (2013.01)] 30 Claims
 
1. A cation of Formula I, wherein:

OG Complex Work Unit Chemistry
R1 is C1-4 alkyl;
R2 is independently selected from the group consisting of: H, halogen-substituted C1-4 alkyl, NR9R10, and CN;
R3 is independently selected from the group consisting of: H, halogen-substituted C1-4 alkyl, NR9R10, and CN;
R4 and R5 are independently selected from the group consisting of: H, C1-4 alkyl, halogen-substituted C1-4 alkyl, NR9R10, and CN;
R6 is H or halogen;
R7 is H, methyl, or NR11R12; and
R8 is H, C1-4 alkyl, halogen-substituted C1-4 alkyl;
R9, R10, R11, and R12 are independently selected from H and C1-4 alkyl, wherein R9 and R10, are independently selected from C1-4 alkyl when R4 is NR9R10;
wherein the cation has at least two non-hydrogen substituents at positions R2-R8;
and wherein at least one of R2, R3, R5, and R7 is NH2.