US 12,240,815 B2
Potent and selective human neuronal nitric oxide synthase inhibitors
Richard B. Silverman, Winnetka, IL (US); and Ha T. Do, Evanston, IL (US)
Assigned to Northwestern University, Evanston, IL (US)
Filed by Northwestern University, Evanston, IL (US)
Filed on Feb. 24, 2021, as Appl. No. 17/184,544.
Application 17/184,544 is a continuation of application No. PCT/US2020/019466, filed on Feb. 24, 2020.
Claims priority of provisional application 62/980,735, filed on Feb. 24, 2020.
Prior Publication US 2021/0269400 A1, Sep. 2, 2021
Int. Cl. C07D 213/73 (2006.01); C07D 401/06 (2006.01); C07D 401/10 (2006.01); C07D 413/10 (2006.01)
CPC C07D 213/73 (2013.01) [C07D 401/06 (2013.01); C07D 401/10 (2013.01); C07D 413/10 (2013.01)] 23 Claims
 
1. A compound of a Formula (I) or a salt or solvate thereof:

OG Complex Work Unit Chemistry
where X is hydrogen, C1-C6-alkyl, C1-C6-alkoxy, halogen, or haloalkyl,
custom character represents a single, double, or triple bond;
Y is aryl substituted with halogen and a substituent having a formula —Z—Ra; or Y is 7-10 membered heteroaryl substituted at one or more ring positions with a substituent having a formula —Z—Ra; or Y has a formula —Z—Ra;
Z is selected from C1-C6-alkyl, C2-C6-alkenyl, and C2-C6-alkynyl;
Ra is selected from alkylamino, dialkylamino, and a 4-6 membered heterocycle which contains at least one nitrogen atom and which heterocycle is optionally substituted at one or more positions with alkyl, alkoxy, or halogen; and
wherein if Y is aryl substituted with one halogen and one substituent having a formula —C1-C6-alkyl-Ra, then Ra is the 4-6 membered heterocycle which contains at least one nitrogen atom and which heterocycle is optionally substituted at one or more positions with alkyl, alkoxy, or halogen.