Patent number: 9540389
Abstract: Novel compounds are disclosed having the structure of Formula I: wherein, n is an integer from 1 to 5; X is —CN, —F, —Cl, —Br, —I, —NO2; W is S, SO, SO2, O, NH, or NR5; R5 is alkyl, aralkyl, alkenyl, or alkynyl; Y is O, S; Z is NR1R2 or heterocycloalkyl; R1, R2 are, independently, hydrogen, alkyl, aralkyl, alkenyl, alkynyl, or cycloalkyl and may be optionally substituted with halo, hydroxy, alkoxy, amino, alkylamino, carboxy, alkoxycarbonyl, or nitrile groups; R3 and R4 are, independently, hydrogen, alkyl, aralkyl, alkenyl, alkynyl, or cycloalkyl and may be optionally substituted with halo, hydroxy, alkoxy, amino, alkylamino, carboxy, alkoxycarbonyl, or nitrile groups, and may together form a cyclic structure; and Ar is mono-, di-, or tri-substituted phenyl or heteroaryl, a pharmaceutically acceptable salts thereof. The compounds are potent bacterial efflux pump inhibitors (EPIs).
Type:
Grant
Filed:
May 3, 2014
Date of Patent:
January 10, 2017
Assignee:
Microbiotix, Inc.
Inventors:
Timothy J. Opperman, Son T. Nguyen, Steven M. Kwasny, Xiaoyuan Ding
Publication number: 20160075714
Abstract: Novel compounds are disclosed having the structure of Formula I: wherein, n is an integer from 1 to 5; X is —CN, —F, —Cl, —Br, —I, —NO2; W is S, SO, SO2, O, NH, or NR5; R5 is alkyl, aralkyl, alkenyl, or alkynyl; Y is O, S; Z is NR1R2 or heterocycloalkyl; R1, R2 are, independently, hydrogen, alkyl, aralkyl, alkenyl, alkynyl, or cycloalkyl and may be optionally substituted with halo, hydroxy, alkoxy, amino, alkylamino, carboxy, alkoxycarbonyl, or nitrile groups; R3 and R4 are, independently, hydrogen, alkyl, aralkyl, alkenyl, alkynyl, or cycloalkyl and may be optionally substituted with halo, hydroxy, alkoxy, amino, alkylamino, carboxy, alkoxycarbonyl, or nitrile groups, and may together form a cyclic structure; and Ar is mono-, di-, or tri-substituted phenyl or heteroaryl, a pharmaceutically acceptable salts thereof. The compounds are potent bacterial efflux pump inhibitors (EPIs).
Type:
Application
Filed:
May 3, 2014
Publication date:
March 17, 2016
Applicant:
MICROBIOTIX, INC.
Inventors:
Timothy J. Opperman, Son T. Nguyen, Steven M. Kwasny, Xiaoyuan Ding