US 12,202,798 B2
Antimicrobial compounds, compositions, and articles of manufacture for selectively inhibiting pathogenic microbes
Anuj Singhal, Huntsville, AL (US); Robert H. Cichewicz, Norman, OK (US); Lin Du, Norman, OK (US); JianLan You, Forest Hills, NY (US); Hanumantha Rao Paritala, Madison, AL (US); and Abigail Grace Edwards, Hazel Green, AL (US)
Assigned to CFD RESEARCH CORPORATION, Huntsville, AL (US); and The Board of Regents of the University of Oklahoma, Norman, OK (US)
Filed by CFD RESEARCH CORPORATION, Huntsville, AL (US); and THE BOARD OF REGENTS OF THE UNIVERSITY OF OKLAHOMA, Norman, OK (US)
Filed on Jun. 17, 2020, as Appl. No. 16/904,370.
Claims priority of provisional application 62/863,027, filed on Jun. 18, 2019.
Prior Publication US 2020/0399218 A1, Dec. 24, 2020
Int. Cl. C07D 209/30 (2006.01); A01N 25/08 (2006.01); A01N 43/38 (2006.01); A01N 43/40 (2006.01); A01N 43/90 (2006.01); A01N 55/00 (2006.01); A61K 47/54 (2017.01); A61K 47/60 (2017.01); C07D 401/12 (2006.01); C07D 417/12 (2006.01); C07D 471/04 (2006.01); C07F 7/18 (2006.01)
CPC C07D 209/30 (2013.01) [A01N 25/08 (2013.01); A01N 43/38 (2013.01); A01N 43/40 (2013.01); A01N 43/90 (2013.01); A01N 55/00 (2013.01); A61K 47/54 (2017.08); A61K 47/545 (2017.08); A61K 47/60 (2017.08); C07D 401/12 (2013.01); C07D 417/12 (2013.01); C07D 471/04 (2013.01); C07F 7/1804 (2013.01)] 20 Claims
 
1. A compound selected from the group consisting of:
3-((4-bromophenyl)thio)-6-fluoro-1H-indole (172A);
2-((4-bromophenyl)thio)-3-methyl-1H-indole (172B);
methyl 3-((4-bromophenyl)thio)-1H-indole-5-carboxylate (172G);
5-bromo-3-((4-bromophenyl) sulfinyl)-1H-indole (172I);
5-bromo-3-((4-bromophenyl) sulfonyl)-1H-indole (172J);
6-bromo-3-((4-bromophenyl)thio)-1H-indole (174A);
5,6-dibromo-3-((4-bromophenyl)thio)-1H-indole (174AB);
5,7-dibromo-3-((4-bromophenyl)thio)-1H-indole (174AC);
5-bromo-3-((perchlorophenyl)thio)-1H-indole (174AD);
4,6-dibromo-3-((4-bromophenyl)thio)-1H-indole (174AE);
5-bromo-3-((4-bromophenyl)thio)-6-chloro-1H-indole (174AF);
5-bromo-3-((2,4,6-trichlorophenyl)thio)-1H-indole (174AG);
5-bromo-3-((3,4,5-tribromophenyl)thio)-1H-indole (174AH);
2-((5-bromo-1H-indol-3-yl)thio)phenol (174AI);
5-bromo-3-((2-chlorophenyl)thio)-1H-indole (174AJ);
3-((2-aminophenyl)thio)-2-methyl-1H-indol-5-ol (174AK);
3-((1H-indol-3-yl)thio)-5-bromo-1H-indole (174AL);
3-((2-hydroxyphenyl)thio)-2-methyl-1H-indol-5-ol (174AO);
3-((2-hydroxyphenyl)thio)-1H-indol-5-ol (174AP);
2-((5-methoxy-1H-indol-3-yl)thio)phenol (174AQ);
3-((2-bromophenyl)thio)-1H-indol-5-ol (174AR);
3-((2-bromophenyl)thio)-5-methoxy-1H-indole (174AS);
(2-((5-bromo-1H-indol-3-yl)thio)phenyl) methanol (174AT);
5-bromo-3-((2-(fluorophenyl)thio)-1H-indole (174AU);
5-bromo-3-((2-(trifluoromethyl)phenyl)thio)-1H-indole (174AV);
3-((2-bromophenyl)thio)-5-(trifluoromethyl)-1H-indole (174AX);
5-bromo-3-(o-tolylthio)-1H-indole (174AY);
5-bromo-3-((2-bromophenyl)thio)-2-methyl-1H-indole (174AZ);
4-bromo-3-((4-bromophenyl)thio)-1H-indole (174D);
3-((4-bromophenyl)thio)-5-fluoro-1H-indole (174E);
7-bromo-3-((4-bromophenyl)thio)-1H-indole (174H);
5-bromo-3-((3-bromophenyl)thio)-1H-indole (174N);
5-bromo-3-((4-bromobenzyl)thio)-1H-indole (1740);
3-([1,1′-biphenyl]-4-ylthio)-5-bromo-1H-indole (174R);
5-bromo-3-((2,3-dichlorophenyl)thio)-1H-indole (174T);
5-bromo-3-((2,4-dichlorophenyl)thio)-1H-indole (174V);
5-bromo-3-((3,4-dichlorophenyl)thio)-1H-indole (174W);
5-bromo-2-((5-bromo-1H-indol-3-yl)thio)aniline (174X);
3-((5-bromo-1H-indol-3-yl)thio)aniline (174Y);
2-((5-(trifluoromethyl)-1H-indol-3-yl)thio)phenol (177A);
4-((5-(trifluoromethyl)-1H-indol-3-yl)thio)phenol (177B);
2-((5-(trifluoromethyl)-1H-indol-3-yl)thio)aniline (177C);
3-((2-fluorophenyl)thio)-5-(trifluoromethyl)-1H-indole (177D);
3-((2-bromophenyl)thio)-5-fluoro-1H-indole (177E);
5-(trifluoromethyl)-3-((2-(trifluoromethyl)phenyl)thio)-1H-indole (177F);
3-((2-ethylphenyl)thio)-5-(trifluoromethyl)-1H-indole (177G);
(5-bromo-3-((2-bromophenyl)thio)-1H-indol-2-yl) methanol (177H);
(3-((2-ethylphenyl)thio)-5-(trifluoromethyl)-1H-indol-2-yl) methanol (177I);
N-((3-((4-hydroxyphenyl)thio)-1H-indol-5-yl)methyl)-4-(triethoxysilyl) butanamide (156SI); and
3-((2-aminophenyl)thio)-5-bromo-N-(3-(triethoxysilyl) propyl)-1H-indole-2-carboxamide (174SI),
or salts thereof.