IP Library › Granted Patent US 9,399,619

Granted Patent B2

US 9,399,619 · App. 14/130,140 · Granted Jul 26, 2016

Sulfamoylbenzamide derivatives as antiviral agents against HBV infection

Inventors: Ju-Tao Guo (Lansdale, PA); Xiaodong Xu (Doylestown, PA); Timothy M. Block (Doylestown, PA)

Assignees: Baruch S. Blumberg Institute; Drexel University

C07C311/46 A61K31/167 A61K31/18 C07D211/96 C07D213/40 C07D223/04 C07D281/16 C07D295/26 C07D307/52 C07D307/68 A61K31/341 A61K31/44 A61K31/445 A61K31/5377 A61K31/541 A61K31/55

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Quick Facts

Patent No.: US 9,399,619
App. No.: 14/130,140
Granted: Jul 26, 2016
Kind: B2

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Abstract

Pharmaceutical compositions of the invention comprise sulfamoylbenzamide derivative useful as pregenomic RNA encapsidation inhibitors, useful for the treatment of Hepatitis B virus (HBV) infection.

Claims (151)

1. A method for treating Hepatitis B virus (HBV) infection and related conditions, said method comprising administering to a subject in need of such treatment a therapeutically effective amount of at least one compound having formula (I):

wherein

R 1 is hydrogen;

R 2 is selected from a group consisting of hydrogen, methyl, trifluoromethyl, fluorine, and chlorine;

R 3 is selected from a group consisting of hydrogen, methyl, fluorine, and chlorine;

R 4 is selected from a group consisting of hydrogen, fluorine, chlorine, and methyl;

R 5 is selected from a group consisting of hydrogen and chlorine;

R 7 is selected from a group consisting of hydrogen, chlorine, fluorine, and bromine;

R 9 is selected from a group consisting of hydrogen, methyl, fluorine, and chlorine;

R x is selected from the group consisting of: NH 2 ,

or a pharmaceutically acceptable salt form thereof.

2. The method of claim 1 , wherein the at least one compound is selected from the group consisting of

2-Chloro-5-sulfamoyl-N-3-methylphenyl-benzamide;

4-Fluoro-3-sulfamoyl-N-(3-trifluoromethyl-phenyl)-benzamide;

N-(2-Chloro-5-trifluoromethyl-phenyl)-4-fluoro-3-sulfamoyl-benzamide;

N-Phenyl-3-sulfamoyl-benzamide;

5-sec-Butylsulfamoyl-N-(3,4-difluoro-phenyl)-2-fluoro-benzamide;

3-Diethylsulfamoyl-N-phenyl-benzamide;

5-Diethylsulfarnoyl-N-(3,4-difluoro-phenyl)-2-fluoro-benzarnide;

2-Chloro-5-diethylsulfamoyl-N-m-tolyl-benzamide;

N-(4-Chloro-phenyl)-3-diethylsulfamoyl-benzamide;

5-Allylsulfamoyl-N(3,4-difluoro-phenyl)-2-fluoro-benzamide;

N-(3,4-Difluoro-phenyl)-5-dipropylsulfamoyl-2-fluoro-benzamide;

5-Cycloheptylsulfamoyl-N-(3,4-difluoro-phenyl)-2-fluoro-benzamide;

5-Cycloheptylsulfamoyl-2-fluoro-N-p-tolyl-benzamide;

5-Cyclohexylsulfamoyl-N-(3,4-difluoro-phenyl)-2-fluoro-benzamide;

2-Bromo-5-cyclohexylsulfamoyl-N-phenyl-benzamide;

4-Chloro-3-cyclohexylsulfamoyl-N-(4-fluoro-phenyl)-benzamide;

3-Cyclohexylsulfamoyl-4-methyl-N-phenyl-benzamide;

N-(3,4-Difluoro-phenyl)-4-fluoro-3-(2-methyl-cyclohexylsulfamoyl)-benzamide;

3-Cyclopentylsulfamoyl-N-phenyl-benzamide,

5-Cyclopentylsulfamoyl-N-(3,4-difluoro-phenyl)-2-fluoro-benzamide;

5-Cyclopentylsulfamoyl-2-fluoro-N-(4-fluoro-phenyl)-benzamide;

5-Cyclopentylsulfamoyl-N-(3,5-dimethyl-phenyl)-2-fluoro-benzamide;

3-Cyclopentylsulfamoyl-4-fluoro-N-3-methylphenyl-benzamide;

5-Cyclopentylsulfamoyl-N-(3,5-dichloro-phenyl)-2-fluoro-benzamide;

3-[(Furan-2-ylmethyl)-sulfamoyl]-N-phenyl-benzamide;

N-(3-Chloro-4-fluoro-phenyl)-5-[(furan-2-ylmethyl)-sulfamoyl]-2-methyl-benzamide;

2-Fluoro-N-(3-fluoro-phenyl)-5-[(furan-2-ylmethyl)-sulfamoyl]-benzamide;

N-(3,5-Dichloro-phenyl)-2-fluoro-5-[(furan-2-ylmethyl)-sulfamoyl]-benzamide;

4-Fluoro-3-[(furan-2-ylmethyl)-sulfamoyl]-N-3-methylphenyl-benzamide;

5-[(4-Chloro-3-phenylcarbamoyl-benzenesulfonylamino)-methyl]-furan-2-carboxylic acid methyl ester;

N-(3-Chloro-phenyl)-5-(2-cyclohex-1-enyl-ethylsulfamoyl)-2-fluoro-benzamide;

5-(2-Cyclohex-1-enyl-ethylsulfamoyl)-N-(3,5-dimethyl-phenyl)-2-fluoro-benzamide;

N-(3-Chloro-phenyl)-4-fluoro-3-[(pyridin-3-ylmethyl)-sulfamoyl]-benzamide;

N-(3,4-Difluoro-phenyl)-2-fluoro-5-phenethylsulfamoyl-benzamide;

N-(3-Chloro-phenyl)-2-fluoro-5-phenethylsulfamoyl-benzamide;

5-Benzylsulfamoyl-N-(3-chloro-4-fluoro-phenyl)-2-fluoro-benzamide;

5-Benzylsulfamoyl-2-chloro-N-phenyl-benzamide;

N-(4-Chloro-phenyl)-5-[2-(3,4-dimethoxy-phenyl)-ethylsulfamoyl]-2-fluoro-benzamide;

5-(2-Chloro-benzylsulfamoyl)-N-(3,4-difluoro-phenyl)-2-fluoro-benzamide;

3-(2-Chloro-benzylsulfamoyl)-N-(4-chloro-phenyl)-4-fluoro-benzamide;

2-Fluoro-5-(4-methoxy-phenylsulfamoyl)-N-3-methylphenyl-benzamide;

2-Fluoro-5-(4-fluoro-phenylsulfamoyl)-N-3-methylphenyl-benzamide;

N-(4-Chloro-phenyl)-3-(3-fluoro-phenylsulfamoyl)-benzamide;

N-(4-Chloro-phenyl)-3-2-methylphenylsulfamoyl-benzamide;

N-Phenyl-3-m-tolylsulfamoyl-benzamide;

N-Phenyl-3-o-tolylsulfamoyl-benzamide;

3-(Benzyl-ethyl-sulfamoyl)-N-(3,4-difluoro-phenyl)-4-fluoro-benzamide;

5-(Azepane-1-sulfonyl)-N-(3,4-difluoro-phenyl)-2-fluoro-benzamide;

4-Methyl-N-phenyl-3-(piperidine-1-sulfonyl)-benzamide;

4-chloro-N-(4-fluorophenyl)-3-(piperidin-1-ylsulfonyl)benzamide;

4-Chloro-N-(3-fluoro-phenyl)-3-(morpholine-4-sulfonyl)-benzamide;

4-Chloro-N-phenyl-3-(thiomorpholine-4-sulfonyl)-benzamide;

or a pharmaceutically acceptable form thereof.

3. The method of claim 1 , wherein the at least one compound is administered in a composition further comprising at least one pharmaceutically acceptable excipient.