US 9566254 B2 - Inhibitors And Methods Of Inhibiting Bacterial And Viral Pathogens - The Lens - Free & Open Patent and Scholarly Search

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US 9566254 B2

Inhibitors And Methods Of Inhibiting Bacterial And Viral Pathogens

Published: Feb 14, 2017
Earliest Priority: Feb 19 2010
Family: 12
Cited Works: 13
Cited by: 0
Cites: 6
Additional Info: Cited Works Full text

Abstract

Compounds, pharmaceutical compositions and methods for treating viral and bacterial infections, by administering certain thiourea compounds, specifically acylthiourea, carboximidoylthiourea and S-alkyl isothiourea derivatives and analogs, in therapeutically effective amounts are disclosed.

Claims

A method for the treatment of a viral or bacterial infection or disease associated therewith wherein the viral infection is caused by a virus family selected from the group consisting of: Bunyaviridae, Poxviridae, Arenaviridae, Picornaviridae, Togaviridae, Flaviviridae, Filoviridae, Paramyxoviridae, Orthomyxoviridae and Retroviridae, comprising administering in a therapeutically effective amount to a mammal in need thereof, a compound of Formula II below or a pharmaceutically acceptable salt thereof:
wherein X is selected from the group consisting of oxygen and NH;

Y is selected from the group consisting of: —CH₂—, —C(═O)—, —C(═S)— and —C(═NH)—;

A is selected from the group consisting of: N and CR⁵;

B is selected from the group consisting of: N and CR⁶;

R¹is selected from the group consisting of: hydrogen and ethyl;

R²is selected from the group consisting of: hydrogen and chloro;

R³is selected from the group consisting of: hydrogen, methoxy, amino and hydroxyl;

R⁴is selected from the group consisting of: hydrogen, chloro and amino;

R⁵is selected from the group consisting of hydrogen and aminomethyl; and

R⁶is selected from the group consisting of hydrogen, amino and aminomethyl.
The method of claim 1, wherein X is oxygen.
The method of claim 1, wherein Y is —CH₂—.
The method of claim 1, wherein Y is —C(═O)—.
The method of claim 1, wherein A is C—H.
The method of claim 1, wherein B is C—H.
The method of claim 1, wherein R¹is hydrogen.
The method of claim 1, wherein R²is hydrogen.
The method of claim 1, wherein R³is methoxy.
The method of claim 1, wherein R⁴is chloro.
The method of claim 1, wherein each of R⁵and R⁶is hydrogen.
The method of claim 1, wherein the compound of Formula II is selected from the group consisting of: N-[4-[(4-tert-butylbenzoyl)-carbamothioylamino]-2-hydroxy-phenyl]-2-chloro-benzamide; 4-tert-butyl-N-[[4-[(2-chlorophenyl)-methylamino]-3-methoxy-phenyl]-carbamothioyl]-benzamide; N-[2-amino-4-[(4-tert-butylbenzoyl)-carbamothioylamino]-phenyl]-2-chloro-benzamide hydrochloride; N-[(4-benzamido-2-chloro-phenyl)carbamothioyl]-4-tert-butyl-benzamide; 4-tert-butyl-N-[[4-[(2-chlorobenzene-carbothioyl)amino]-3-methoxy-phenyl]-carbamothioyl]benzamide; 4-(aminomethyl)-N-[4-[(4-tert-butylbenzoyl)-carbamothioylamino]-2-methoxy-phenyl]benzamide hydrochloride; N-[4-[(4-tert-butylbenzene-carboximidoyl) -carbamothioylamino]-2-methoxy-phenyl]-2-chloro-benzamide; 4-tert-butyl-N-[[4-[(2-chlorobenzene-carboximidoyl)amino]-3-methoxy-phenyl]-carbamothioyl]benzamide; 3-(aminomethyl)-N-[4-[(4-tert-butylbenzoyl)-carbamothioylamino]-2-methoxy-phenyl]benzamide hydrochloride; 2-amino-N-[4-[(4-tert-butylbenzoyl)-carbamothioylamino]-2-methoxy-phenyl]benzamide; N-[4-[(4-tert-butylbenzoyl)-carbamothioylamino]-2-methoxy-phenyl]pyridine-3-carboxamide; N-[4-[(4-tert-butylbenzoyl)-carbamothioylamino]-2-methoxy-phenyl]pyridine-4-carboxamide; N-[[4-[(4-aminobenzoyl)amino]-3-methoxy-phenyl]-carbamothioyl]-4-tert-butyl-benzamide hydrochloride; N-[4-[(4-tert-butylbenzoyl) -carbamothioyl-ethyl-amino]-2-methoxy-phenyl]-2-chloro-benzamide; N-[4-[(4-tert -butylbenzoyl)-carbamothioylamino]-2-methoxy-phenyl]-2-chloro-benzamide; and N-[(4-benzamidophenyl)-carbamothioyl]-4-tert-butyl-benzamide.
The method of claim 12, wherein the compound of Formula II is N-[2-amino-4-[(4-tert-butylbenzoyl)-carbamothioylamino]-phenyl]-2-chloro-benzamide hydrochloride.
The method of claim 1, wherein the mammal is a human.
The method of claim 1, wherein said Bunyaviridae is selected from the group consisting of Rift Valley fever virus, La Crosse virus and Andes virus.
The method of claim 1, wherein said Poxviridae is selected from the vaccinia virus and monkeypox virus.
The method of claim 1, wherein said Arenaviridae is selected from the group consisting of Tacaribe virus and lymphocytic choriomeningitis virus.
The method of claim 1, wherein said Picornaviridae is Encephalomyocarditis virus.
The method of claim 1, wherein said Togaviridae is Sindbis virus.
The method of claim 1, wherein said Flaviviridae is Dengue virus.
The method of claim 1, wherein the viral infection is caused by a Filoviridae and said Filoviridae is Ebola virus.
The method of claim 1, wherein said Orthomyxoviridae is an influenza virus.
The method of claim 22, wherein said influenza virus is H1N1 virus.
The method of claim 1, wherein said Retroviridae is a Human Immunodeficiency virus.
The method of claim 1, which further comprises co-administration of at least one agent selected from the group consisting of antiviral agent, vaccine, and interferon.
The method of claim 25, wherein said antiviral agent is Ribavirin.
The method of claim 25, wherein said antiviral agent is cidofovir.
The method of claim 25, wherein said interferon is pegylated.
The method of claim 1, wherein said bacterial infection is caused by a bacteria family selected from the group consisting of Chlamydiaceae and Coxiellaceae.
The method of claim 29, wherein said Chlamydiaceae is selected from the group consisting of Chlamydophila caviae and Chlamydophila muridarum.
The method of claim 29, wherein said Coxiellaceae is Coxiella burnetti.
The method of claim 1, wherein the compound of Formula II is N-[4-[(4-tert -butylbenzoyl)-carbamothioylamino]-2-methoxy-phenyl]-2-chloro-benzamide.
The method of claim 32, wherein the viral infection is Ebola virus.

Owners (US)

Siga Technolgies Inc (Aug 20 2012)
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Applicants

Siga Tech Inc
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Inventors

Allen Iii Robert D
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Amberg Sean M
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Dai Dongcheng
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Burgeson James R
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Hruby Dennis E
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Document History

Publication: Feb 14, 2017
US 9566254 B2
Application: Dec 1, 2015
US 201514955697 A
Priority: Dec 1, 2015
US 201514955697 A
Priority: Sep 5, 2012
US 201213578413 A
Priority: Feb 18, 2011
US 2011/0025356 W
Priority: Feb 19, 2010
US 30610210 P

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