Antimicrobial compounds
View Patent ↗This invention provides compounds and methods for treating, with said compound, a mycobacterial infection by administering to an animal a pharmaceutical composition containing a compound having the formula R—SO n -Z-CO—Y, where R is an alkyl groups having 6-20 carbon atoms, unsaturated hydrocarbon groups having 6-20 carbon atoms, or alkyl groups having 6-20 carbon atoms interrupted by at least one aromatic ring; Z is —CH 2 —, —CH 2 CH 2 —, —NH—NH—, —O—, ——NH—, —O—NH—, —CH 2 —NH—, —CH 2 —O—, —NH—O—, —NH—CH 2 —, —O—CH 2 —, and —CH═CH—; Y is —NH 2 , —O—CH 2 —C 6 H 5 , —CO—CO—O—CH 3 , and —O—CH 3 ; and n is 1 or 2. It has been discovered that these compounds treat microbially-based infections caused by corynebacteria, nocardiae, rhodococcus, and mycobacteria. These compounds may be used to treat mycobacterial cells, such as Mycobacteria tuberculosis , drug resistant M. tuberculosis, M. avium intracellulare, M. leprae, M. paratuberculosis , and pathogenic Mycobacteria sp.
1. A method of inhibiting growth of a mycobacterial cell, comprising administering an effective amount of a compound of formula I to the cell:
R—SO n -Z-CO—Y I
wherein:
R is selected from the group consisting of any alkyl group having from 6-10 carbon atoms, any unsaturated hydrocarbon having from 6-10 carbon atoms, or any alkyl group having from 6-10 carbon atoms interrupted by at least one aromatic ring;
Z is —CH 2 —;
Y is selected from the group consisting of —NH 2 , and —O—CH 3 ; and
n is 1 or 2;
and wherein, the mycobacterial cell is selected from the group consisting of cells of Mycobacteria tuberculosis , drug resistant M. tuberculosis, M. bovis, M. leprae , and M. paratuberculosis.
2. The method of claim 1 , wherein R is an alkyl group having 6-10 carbon atoms interrupted by an aromatic ring to give ortho-, meta-, or para-disubstitution.
3. The method of claim 1 , wherein R is a branched alkyl group.
4. The method of claim 1 , wherein R is an n-alkyl group.
5. The method of claim 1 , wherein n is 1.
6. The method of claim 1 , wherein n is 2.
7. The method of claim 1 , wherein Y is —NH 2 .
8. The method of claim 1 , wherein: R is —(CH 2 ) 9 —CH 3 , n is 1, Z is —CH 2 — and Y is —NH 2 .
9. The method of claim 1 , wherein: R is —(CH 2 ) 7 —CH 3 , n is 1, Z is —CH 2 — and Y is —NH 2 .
10. The method of claim 1 , wherein: R is —(CH 2 ) 9 —CH 3 , n is 2, Z is —CH 2 — and Y is —NH 2 .
11. The method of claim 1 , wherein: R is —(CH 2 ) 7 —CH 3 , n is 2, Z is CH 2 — and Y is —NH 2 —.