IP Library Granted Patent US 8,492,434
Granted Patent B2
US 8,492,434 · App. 13/402,167 · Granted Jul 23, 2013

Antiviral drugs for treatment of arenavirus infection

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Quick Facts
Patent No.
US 8,492,434
App. No.
13/402,167
Granted
Jul 23, 2013
Kind
B2
Abstract

Compounds, methods and pharmaceutical compositions for treating viral infections, by administering certain novel compounds in therapeutically effective amounts are disclosed. Methods for preparing the compounds and methods of using the compounds and pharmaceutical compositions thereof are also disclosed. In particular, the treatment and prophylaxis of viral infections such as caused by hemorrhagic fever viruses is disclosed, i.e., including but not limited to, Arenaviridae (Junin, Machupo, Guanarito, Sabia, Lassa, Tacaribe, and Pichinde), Filoviridae (Ebola and Marburg viruses), Flaviviridae (yellow fever, Omsk hemorrhagic fever and Kyasanur Forest disease viruses), and Bunyaviridae (Rift Valley fever).

Claims (33)

1. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or excipient and a pharmaceutically effective amount of a compound or a pharmaceutically-acceptable salt thereof, selected from the group consisting of

2-Phenyl-cyclopropanecarboxylic acid [1-(4-amino-phenyl)-eth-(E)-ylidene]-hydrazide;

Cyclopropanecarboxylic acid (4-[1-[(2-phenyl-cyclopropanecarbonyl)-hydrazono]-ethyl]-phenyl)-amide;

2-Phenyl-cyclopropanecarboxylic acid [1-(2,4-dimethoxy-phenyl)-eth-(E)-ylidene]-hydrazide;

2-Phenyl-cyclopropanecarboxylic acid [1-p-tolyl-eth-(E)-ylidene]-hydrazide;

2-Phenyl-cyclopropanecarboxylic acid [1-biphenyl-4-yl-eth-(E)-ylidene]-hydrazide;

2-Phenyl-cyclopropanecarboxylic acid [1-(3,4-dimethoxy-phenyl)-eth-(E)-ylidene]-hydrazide;

Furan-2-carboxylic acid (4-[1-[(2-phenyl-cyclopropanecarbonyl)-hydrazono]-ethyl]-phenyl)-amide;

2,4-Dichloro-N-(4-[1-[(2-Phenyl-cyclopropanecarbonyl)-hydrazono]-ethyl]-phenyl)-benzamide;

2-Phenyl-cyclopropanecarboxylic acid [1-(2-hydroxy-phenyl)-eth-(E)-ylidene]-hydrazide;

Thiophene-2-carboxylic acid (4-[1-[(2-phenyl-cyclopropanecarbonyl)-hydrazono]-ethyl]-phenyl)-amide;

2-Phenyl-cyclopropanecarboxylic acid [1-(4-dimethylamino-phenyl)-eth-(E)-ylidene]-hydrazide;

2-Phenyl-cyclopropanecarboxylic acid [1-(4-methoxy-phenyl)-eth-(Z)-ylidene]-hydrazide;

2-Phenyl-cyclopropanecarboxylic acid [1-(4-cyclohexyl-phenyl)-eth-(E)-ylidene]-hydrazide;

N-[3-(1-[[2-(4-tert-Butyl-phenyl)-cyclopropanecarbonyl]-hydrazono]-ethyl)-phenyl]-2-fluoro-benzamide;

5-Chloro-thiophene-2-carboxylic acid (4[1-[(2-phenyl-cyclopropanecarbonyl)-hydrazono]-ethyl]-phenyl)-amide;

2-Fluoro-N-(3-[1-[(2-phenyl-cyclopropanecarbonyl)-hydrazono]-ethyl]-phenyl)-benzamide;

2,2,2-Trifluoro-N-(4-[1-[(2-phenyl-cyclopropanecarbonyl)-hydrazono]-ethyl]-phenyl)-acetamide;

2-(4-tert-Butyl-phenyl)-cyclopropanecarboxylic acid [1-(4-fluoro-phenyl)-eth-(Z)-ylidene]-hydrazide and

2-(4-tert-Butyl-phenyl)-cyclopropanecarboxylic acid [1-(4-methoxy-3-nitro-phenyl)-eth-(Z)-ylidene]-hydrazide,

wherein said pharmaceutical composition is suited for human or animal administration.

2. The pharmaceutical composition of claim 1 , wherein said compound is furan-2-carboxylic acid (4-[1-[(2-phenyl-cyclopropanecarbonyl)-hydrazono]-ethyl]-phenyl)-amide.

3. The pharmaceutical composition of claim 2 , wherein said excipient is solid or semi-solid.

4. The pharmaceutical composition of claim 2 , wherein said excipient is liquid.

5. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a pharmaceutically effective amount of 3-Phenyl-propionic acid [1-(3-amino-phenyl)-eth-(E)-ylidene]-hydrazide or a pharmaceutically-acceptable salt thereof, wherein said pharmaceutical composition is suited for human or animal administration.

6. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a pharmaceutically effective amount of 2-Phenyl-cyclopropanecarboxylic acid [1-thiophen-2-yl-eth-(Z)-ylidene]-hydrazide or a pharmaceutically-acceptable salt thereof, wherein said pharmaceutical composition is suited for human or animal administration.

7. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or excipient and a pharmaceutically effective amount of 2-Phenyl-cyclopropanecarboxylic acid [4-bromo-5-methyl-2-oxo-1,2-dihydro-indol-(3E)-ylidene]-hydrazide or a pharmaceutically-acceptable salt thereof, wherein said pharmaceutical composition is suited for human or animal administration.

8. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or excipient and a pharmaceutically effective amount of 2-Phenyl-cyclopropanecarboxylic acid [5-nitro-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-hydrazide or a pharmaceutically-acceptable salt thereof, wherein said pharmaceutical composition is suited for human or animal administration.

9. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or excipient and a pharmaceutically effective amount of 2-Phenyl-cyclopropanecarboxylic acid [1-acenaphthen-5-yl)-eth-(Z)-ylidene]-hydrazide or a pharmaceutically-acceptable salt thereof, wherein said pharmaceutical composition is suited for human or animal administration.

10. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or excipient and a pharmaceutically effective amount of 2-Phenyl-cyclopropanecarboxylic acid [1-cyclopropyl-eth-(E)-ylidene]-hydrazide or a pharmaceutically-acceptable salt thereof, wherein said pharmaceutical composition is suited for human or animal administration.

11. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or excipient and a pharmaceutically effective amount of 2-Phenyl-cyclopropanecarboxylic acid [2-oxo-1,2-dihydro-indol-(3E)-ylidene]-hydrazide or a pharmaceutically-acceptable salt thereof, wherein said pharmaceutical composition is suited for human or animal administration.

12. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or excipient and a pharmaceutically effective amount of 3-[(2-Phenyl-cyclopropanecarbonyl)-hydrazono]-butyric acid ethyl ester or a pharmaceutically-acceptable salt thereof, wherein said pharmaceutical composition is suited for human or animal administration.

13. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or excipient and a pharmaceutically effective amount of 2-Phenyl-cyclopropanecarboxylic acid [2-methyl-1-phenyl)-prop-(E)-ylidene]-hydrazide or a pharmaceutically-acceptable salt thereof, wherein said pharmaceutical composition is suited for human or animal administration.

Assignments (5)
CONFIRMATORY LICENSE Recorded Jun 17, 2021
From: SIGA TECHNOLOGIES INC
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 056615/0766 →
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 →