IP Library Granted Patent US 8,148,428
Granted Patent B2
US 8,148,428 · App. 12/281,081 · Granted Apr 3, 2012

Antiviral drugs for treatment of arenavirus infection

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Quick Facts
Patent No.
US 8,148,428
App. No.
12/281,081
Granted
Apr 3, 2012
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 (29)

1. A method for the treatment of an Arenavirus infection or disease associated therewith, comprising administering in a therapeutically effective amount to a mammal in need thereof, a compound of Formula I below:

Wherein R 1 and R 2 taken together to be a methylene;

R 3 is hydrogen or methyl and R 4 is substituted or unsubstituted phenyl and

Ar is substituted or unsubstituted phenyl.

2. The method of claim 1 , wherein R 3 is hydrogen.

3. The method of claim 1 , wherein R 3 is methyl.

4. The method of claim 1 , wherein R 4 is unsubstituted phenyl.

5. The method of claim 1 , wherein R 4 is monosubstituted phenyl.

6. The method of claim 5 , wherein the substituent is halogen.

7. The method of claim 6 , wherein the halogen is selected from the group consisting of chlorine and fluorine.

8. The method of claim 7 , wherein R 4 is selected from the group consisting of o-chlorophenyl and p-fluorophenyl.

9. The method of claim 5 ; wherein the substituent is hydroxyl.

10. The method of claim 9 , wherein R 4 is o-hydroxyphenyl.

11. The method of claim 5 , wherein the substituent is alkyl.

12. The method of claim 11 , wherein R 4 is tolyl.

13. The method of claim 5 , wherein the substituent is cycloalkyl.

14. The method of claim 13 , wherein R 4 is p-cyclohexylphenyl.

15. The method of claim 5 , wherein the substituent is alkoxy.

16. The method of claim 15 , wherein the substituent is methoxy.

17. The method of claim 16 , wherein R 4 is p-methoxyphenyl.

18. The method of claim 5 , wherein R 4 is selected from the group consisting of p-nitrophenyl, m-aminophenyl, m-(2-fluorocarboxyamido)phenyl, p-trifluorocarboxamidophenyl, p-(2-fluorocarboxamido)phenyl, p-(1,3- dichlorophenylcarboxamido)phenyl, m-(2-thienylcarboxamido)phenyl, p-dimethylamino-phenyl, p-cyclohexylphenyl, p[2-(5-chloro)thienylcarboxamido]phenyl, p-carboxamidophenyl, p-(2-furylcarboxamido)phenyl, and p-(cyclopropylcarboxamido)phenyl.

19. The method of claim 1 , wherein R 4 is disubstituted phenyl.

20. The method of claim 19 , wherein R 4 is selected from the group consisting of m-nitro-p-methoxyphenyl and o,p-dimethoxyphenyl.

21. The method of claim 1 , wherein Ar is unsubstituted phenyl.

22. The method of claim 1 , wherein Ar is mono-substituted phenyl.

23. The method of claim 22 , wherein Ar is mono-alkyl substituted phenyl.

24. The method of claim 23 , wherein Ar is p-tert butyl phenyl.

25. The method of claim 22 , wherein Ar is m-aminophenyl.

26. A method for the treatment an Arenavirus infection or disease associated therewith, comprising administering in a therapeutically effective amount to a mammal in need thereof, a compound of Formula I below:

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 →
CONFIRMATORY LICENSE Recorded Dec 22, 2011
From: SIGA TECHNOLOGIES, INC.
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 027437/0880 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 4, 2008
From: HRUBY, DENNIS E.; BOLKEN, TOVE C.; AMBERG, SEAN; DAI, DONGCHENG
To: SIGA TECHNOLOGIES, INC.
Reel/Frame 021780/0547 →