IP Library Granted Patent US 8,791,110
Granted Patent B2
US 8,791,110 · App. 13/339,478 · Granted Jul 29, 2014

Anti-arenaviral compounds

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Quick Facts
Patent No.
US 8,791,110
App. No.
13/339,478
Granted
Jul 29, 2014
Kind
B2
Abstract

Described herein are 4-methyl-piperazine-1-carbothioic acid amide derivatives and analogs, as well as compositions containing the same, for the treatment or prophylaxis of viral infections and diseases associated therewith, particularly those viral infections and associated diseases caused by hemorrhagic fever viruses, such as Arenaviruses.

Claims (30)

1. A method for treatment of an Arenavirus infection comprising administering in a therapeutically effective amount to a mammal in need thereof, a compound selected from the group consisting of:

N1,N4-diphenylpiperazine-1,4-dicarbothioamide;

N-(4-chlorophenyl)-4-methyl-piperazine-1-carbothioamide;

N-(3,4-dichlorophenyl)-4-phenyl-piperazine-1-carbothioamide;

N-(3-chlorophenyl)-4-methyl-piperazine-1-carbothioamide;

N-(2,4-dichlorophenyl)-4-methyl-piperazine-1-carbothioamide;

4-methyl-N-(m-tolyl)piperazine-1-carbothioamide;

N-(3,4-dichlorophenyl)piperidine-1-carbothioamide;

N-(3,4-dichlorophenyl)morpholine-4-carbothioamide;

4-methyl-N-[3-(trifluoromethyl)phenyl]piperazine-1-carbothioamide;

ethyl 4-[(3,4-dichlorophenyl)carbamothioyl]piperazine-1-carboxylate;

N-(3,4-dichlorophenyl)-4-(2-pyridyl)piperazine-1-carbothioamide;

N-(3-methoxyphenyl)-4-methyl-piperazine-1-carbothioamide;

N-(3,5-dimethylphenyl)-4-methyl-piperazine-1-carbothioamide;

N-(2,4-dimethylphenyl)-4-methyl-piperazine-1-carbothioamide;

1-tert-butyl-3-(3,4-dichlorophenyl)thiourea;

N-(4-chloro-2,5-dimethoxy-phenyl)-4-methyl-piperazine-1-carbothioamide;

N-(4-anilinophenyl)-4-methyl-piperazine-1-carbothioamide;

1-(3,4-dichlorophenyl)-3-(4-ethylphenyl)thiourea;

1-(3,4-dichlorophenyl)-3-(m-tolyl)thiourea;

N-(3,4-dichlorophenyl)-4-pyrimidin-2-yl-piperazine-1-carbothioamide;

N-(3-chloro-4-fluoro-phenyl)-4-methylsulfonyl-piperazine-1-carbothioamide;

N-(3-chloro-4-methyl-phenyl)-4-ethyl-piperazine-1-carbothioamide;

1-(3-chloro-4-fluoro-phenyl)-3-[4-(diethylamino)phenyl]thiourea and

1-[(3-chlorophenyl)methyl]-1-(2-morpholinoethyl)-3-phenyl-thiourea.

2. The method of claim 1 , wherein the compound of Formula I is N-(3,4-dichlorophenyl)piperidine-1-carbothioamide.

3. The method of claim 1 , wherein the compound of Formula I is N-(3,4-dichlorophenyl)morpholine-4-carbothioamide.

4. The method of claim 1 , wherein the mammal is a human.

5. The method of claim 1 , wherein an Arenavirus is selected from the group consisting of Junin, Machupo, Tacaribe, Guanarito, Machupo, Pichinde and Lassa.

6. The method of claim 1 , further comprising administering to the subject an additional antiviral agent selected from the group consisting of zidovudine, acyclovir, ganciclovir, vidarabidine, idoxuridine, trifluridine, foscarnet, interferon, amantadine, rimantadine, and ribavirin.

Assignments (6)
RELEASE OF SECURITY INTEREST Recorded Apr 2, 2015
From: GENERAL ELECTRIC CAPITAL CORPORATION, AS AGENT
To: SIGA TECHNOLOGIES, INC.
Reel/Frame 035319/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2014
From: SIGA TECHNOLOGIES INC.
To: KINETA FOUR LLC
Reel/Frame 033588/0427 →
RELEASE OF SECURITY INTEREST Recorded Aug 14, 2014
From: GENERAL ELECTRIC CAPITAL CORPORATION
To: SIGA TECHNOLOGIES INC.
Reel/Frame 033544/0324 →
SECURITY AGREEMENT Recorded Dec 31, 2012
From: SIGA TECHNOLOGIES, INC.
To: GE CAPITAL EQUITY INVESTMENTS, INC. C/O GE HEALTHCARE FINANCIAL SERVICES, INC.
Reel/Frame 029557/0771 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 21, 2012
From: AMBERG, SEAN M.; DAI, DONGCHENG; BOLKEN, TOVE' C.; HRUBY, DENNIS E.
To: SIGA TECHNOLOGIES, INC.
Reel/Frame 028821/0404 →
CONFIRMATORY LICENSE Recorded Jul 16, 2012
From: SIGA TECHNOLOGIES, INC.
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 028557/0498 →