Imidazolyl amide compounds and uses related thereto

Patent metadata

Field	Value
Publication number	US-9365523-B2
Application number	US-201214006259-A
Country	US
Kind code	B2
Filing date	Mar 28, 2012
Priority date	Mar 31, 2011
Publication date	Jun 14, 2016
Grant date	Jun 14, 2016

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.

First claim

What is claimed:

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.

Assignees

• Plemper Richard K
• Snyder James P
• Sun Aiming
• Ndungu John M
• Yoon Jeong-Joong
• Univ Emory
• Childrens Healthcare Atlanta Inc

Inventors

• Plemper Richard K
• Snyder James P
• Sun Aiming
• Ndungu John M
• Yoon Jeong-Joong

Classifications

• A61K31/4184

  condensed with carbocyclic rings, e.g. benzimidazoles · CPC title

• A61K31/506

  not condensed and containing further heterocyclic rings · CPC title

• C07D403/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• A61K31/4439

  containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465) · CPC title

• C07D401/12

  linked by a chain containing hetero atoms as chain links · CPC title