US 11,731,964 B2
Benzamide antibacterial agents
Herman O. Sintim, West Lafayette, IN (US); Mohamed Seleem, West Lafayette, IN (US); Clement Opoku-Temeng, Worcester, MA (US); Haroon Taj Mohammad, West Lafayette, IN (US); and George Naclerio, Lafayette, IN (US)
Assigned to Purdue Research Foundation, West Lafayette, IN (US)
Appl. No. 17/46,957
Filed by Purdue Research Foundation, West Lafayette, IN (US)
PCT Filed Mar. 29, 2019, PCT No. PCT/US2019/024934
§ 371(c)(1), (2) Date Oct. 12, 2020,
PCT Pub. No. WO2019/199496, PCT Pub. Date Oct. 17, 2019.
Claims priority of provisional application 62/656,638, filed on Apr. 12, 2018.
Prior Publication US 2021/0047316 A1, Feb. 18, 2021
Int. Cl. C07D 417/14 (2006.01); A61P 31/04 (2006.01); C07D 409/14 (2006.01); C07D 413/12 (2006.01); C07D 413/14 (2006.01)
CPC C07D 417/14 (2013.01) [A61P 31/04 (2018.01); C07D 409/14 (2013.01); C07D 413/12 (2013.01); C07D 413/14 (2013.01)] 12 Claims
 
1. A compound having a formula

OG Complex Work Unit Chemistry
or an analog thereof or a pharmaceutically acceptable salt thereof, wherein
X is O;
R1 is methyl;
R2 is an alkyl, alkenyl, alkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl, heterocyclyl, cycloalkyl, cycloalkenyl, cycloheteroalkyl, cycloheteroalkenyl, acyl, aryl, heteroaryl, arylalkyl, arylalkenyl, or arylalkynyl;
R3 represents four substituents, each independently selected from the group consisting of hydrogen, deuterium, halo, azido, cyano, nitro, hydroxy, amino, thio, carboxy, ester, amide, and derivatives thereof, and acyl, sulfoxyl, sulfonyl, phosphate, phosphoryl, alkyl, alkenyl, alkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl, heterocyclyl, cycloalkyl, cycloalkenyl, cycloheteroalkyl, cycloheteroalkenyl, aryl, heteroaryl, arylalkyl, arylalkenyl, and arylalkynyl or any two adjacent substituents are taken together with the attached carbons form cyclic or heterocyclic moiety; and
R4 is an acyl, ester, alkenyl, alkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl, heterocyclyl, cycloalkyl, cycloalkenyl, cycloheteroalkyl, cycloheteroalkenyl, aryl, heteroaryl, arylalkyl, arylalkenyl, and arylalkynyl, and wherein R4 is not a thiophene ring or a substituted thiophene ring, wherein R4 is optionally substituted with one or more of a halogen that is not fluoride, an alkoxy group, a hydroxyl group, an aryloxy group, an aralkyloxy group, a carbonyl group, a thiol, a cyano, an acyl, and an amino group.