US 11,912,687 B2
3,4,5-trisubstituted-1,2,4-triazoles and 3,4,5-trisubstituted-3-thio-1,2,4-triazoles and uses thereof
Kenneth A. Witt, Edwardsville, IL (US); Albert M. Crider, Maryville, IL (US); William Neumann, St. Louis, MO (US); Audrey Hospital, Robbinsville, NJ (US); Karin Sandoval, Edwardsville, IL (US); and Maria Kontoyianni, Glen Carbon, IL (US)
Assigned to Board of Trustees of the Southern Illinois University, Edwardsville, IL (US)
Filed by Board of Trustees of the Southern Illinois University, Edwardsville, IL (US)
Filed on Sep. 3, 2021, as Appl. No. 17/466,480.
Application 17/466,480 is a continuation in part of application No. 16/613,086, granted, now 11,136,312, previously published as PCT/US2018/032368, filed on May 11, 2018.
Claims priority of provisional application 62/505,384, filed on May 12, 2017.
Prior Publication US 2022/0002274 A1, Jan. 6, 2022
Int. Cl. C07D 401/14 (2006.01); C07D 403/06 (2006.01); C07D 403/14 (2006.01)
CPC C07D 403/14 (2013.01) [C07D 401/14 (2013.01); C07D 403/06 (2013.01)] 20 Claims
 
1. A compound of Formula (II):

OG Complex Work Unit Chemistry
wherein
custom character are independently a single bond or is absent;
A is C(H) or N;
B and C are independent C(H), N, N(H), O, or S, provided that when B or C is C(H) or N, custom character is a single bond, and when B or C is N(H), O, or S, custom character is absent;
D is S, O, NR16, P, sulfone, or sulfoxide, wherein R16 is hydrogen, C1-C6 alkyl, aryl, or benzyl;
R1 and R7 are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted cycloalkyl or substituted or unsubstituted fused ring system;
R2 is substituted or unsubstituted C1-C6 alkyl;
R3, R4, and R5 are independently hydrogen, F, Cl, Br, I, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amine, thiosulfinate, thiosulfonate, thioamide, sulfimide, sulfoximide, sulfonediimine, or sulfur halide;
R6 and R8 are independently hydrogen, F, Cl, Br, I, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted cycloalkyl; and
R9 and R15 are independently substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted cycloalkyl;
or a pharmaceutically acceptable salt thereof.