IP Library › Granted Patent US 9,365,523
Granted Patent B2
US 9,365,523 · App. 14/006,259 · Granted Jun 14, 2016

Imidazolyl amide compounds and uses related thereto

Inventors: Richard K. Plemper (Decatur, GA); James P. Snyder (Atlanta, GA); Aiming Sun (Atlanta, GA); John M. Ndungu (Decatur, GA); Jeong-Joong Yoon (Decatur, GA)
Assignees: Emory University; Children's Healthcare of Atlanta, Inc.
C07D235/28A61K31/4184A61K31/422A61K31/427A61K31/4439A61K31/454A61K31/496A61K31/506A61K31/53A61K31/5377A61K45/06C07D401/04C07D401/06C07D401/12C07D403/06C07D403/12C07D413/12C07D417/12
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Quick Facts
Patent No.
US 9,365,523
App. No.
14/006,259
Granted
Jun 14, 2016
Kind
B2
Abstract

This disclosure relates to antiviral compounds disclosed herein and uses related thereto. In certain embodiments, the disclosure relates to pharmaceutical compositions comprising 2-((benzo[d]imidazol-2-yl)thio)-N-phenylpropanamide derivatives, N-phenyl-2-((1-phenyl-benzo[d]imidazol-2-yl)thio)propanamide derivatives, or 2-((benzo[d]imidazol-2-yl)thio)-N-(2-chloro-4-methylphenyl)propanamide derivatives. The derivatives may be substituted with one or more substituents. Typically, the pharmaceutical composition comprises a compound of Formula (I), or salt, prodrug, or ester thereof wherein X, Y, and R1 to R7 are described herein.

Claims (36)

1. A pharmaceutical composition comprising a pharmaceutically acceptable carrier, diluent or excipient and a compound selected from:

N-(2-chloro-4-methylphenyl)-2-((1-(4-(morpholinomethyl)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(4-(cyanomethoxy)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(4-(2-hydroxyethoxy)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(4-(2-(dimethylamino)ethyl)amino)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(4-(2-(dimethylamino)ethyl)(methyl)amino)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

2-((1-(4-(2-acetamidoethoxy)phenyl)-benzo[d]imidazol-2-yl)thio)-N-(2-chloro-4-methylphenyl)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(4-(2-oxoethyl)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(4-(2-hydroxyethyl)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(4-(2-(methylamino)ethyl)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

2-(4-(2-((1-(2-chloro-4-methylphenyl)amino)-1-oxopropan-2-yl)thio)-benzo[d]imidazol-1-yl)phenoxy)acetic acid;

methyl 2-(4-(2-((1-((2-chloro-4-methylphenyl)amino)-1-oxopropan-2-yl)thio)-benzo[d]imidazol-1-yl)phenoxy)acetate;

2-((1-(4-aminophenyl)-benzo[d]imidazol-2-yl)thio)-N-(2-chloro-4-methylphenyl)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(4-hydroxyphenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(4-ethoxyphenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(4-(dimethylamino)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(4-(4-methylpiperazin-1-yl)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(4-morpholinophenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(4-(hydroxymethyl)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

2-((1-(4-azidophenyl)-benzo[d]imidazol-2-yl)thio)-N-(2-chloro-4-methylphenyl)propanamide;

4-(2-((1-(2-chloro-4-methylphenyl)amino)-1-oxopropan-2-yl)thio)-benzo[d]imidazol-1-yl)benzoic acid;

N-(2-chloro-4-methylphenyl)-2-((1-(4-((dimethylamino)methyl)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

methyl 4-(2-((1-((2-chloro-4-methylphenyl)amino)-1-oxopropan-2-yl)thio)-benzo[d]imidazol-1-yl)benzoate;

N-(2-chloro-4-methylphenyl)-2-((1-(4-methoxyphenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-phenyl-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(3-methoxyphenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(m-tolyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(3,5-dimethoxyphenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(3-(morpholinomethyl)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

3-(2-((1-((2-chloro-4-methylphenyl)amino)-1-oxopropan-2-yl)thio)-benzo[d]imidazol-1-yl)benzoic acid;

N-(2-chloro-4-methylphenyl)-2-((1-(2-(morpholinomethyl)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(3-(hydroxymethyl)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(2-(hydroxymethyl)phenyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(4-methoxybenzyl)-benzo[d]imidazol-2-yl)thio)propanamide;

N-(2-chloro-4-methylphenyl)-2-((1-(phenylsulfonyl)-benzo[d]imidazol-2-yl)thio)propanamide; and

N-(2,4-dichlorophenyl)-2-((1-(4-methoxybenzyl)-benzo[d]imidazol-2-yl)thio)propanamide, or salts thereof.

Assignments (3)
CONFIRMATORY LICENSE Recorded Nov 12, 2014
From: EMORY UNIVERSITY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 034206/0756 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 28, 2014
From: EMORY UNIVERSITY
To: EMORY UNIVERSITY; CHILDREN'S HEALTHCARE OF ATLANTA, INC
Reel/Frame 033398/0148 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 25, 2013
From: PLEMPER, RICHARD K.; SNYDER, JAMES P.; SUN, AIMING; NDUNGU, JOHN M.; YOON, JEONG-JOONG
To: EMORY UNIVERSITY
Reel/Frame 031668/0974 →
Continuity (2)
Provisional Application 61470020 · Mar 31, 2011
Related Publication 20140080828A1 · Mar 20, 2014