Antiviral compounds

Patent metadata

Field	Value
Publication number	US-9840465-B2
Application number	US-201414765539-A
Country	US
Kind code	B2
Filing date	Feb 2, 2014
Priority date	Feb 2, 2013
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

Compounds useful for treating and preventing viral infections including influenza are disclosed. Methods of treating or preventing viral infections, including influenza A infections are disclosed. Specifically, aminoadamantane derivatives that are structurally analogous to amantadine, including spirocyclic compounds, are provided for the treatment of amantadine-insensitive influenza infection in a subject.

First claim

The invention claimed is:

1. A compound of formula I or pharmaceutically acceptable salts thereof,

wherein R 1 is selected from C 5 -C 8 alkyl, C 1 -C 5 alkylenearyl, and aryl, wherein the aryl of alkylenearyl and aryl are optionally substituted with C 1 -C 4 alkyl, provided that the compounds of formula I exclude compounds where R 1 is phenyl.

2. The compound or pharmaceutically acceptable salts of claim 1 , wherein R 1 is C 5 -C 8 alkyl.

3. A pharmaceutical composition comprising a compound or a pharmaceutically acceptable salt thereof of claim 1 and a pharmaceutically acceptable carrier.

4. The compound of claim 1 , wherein R 1 is C 5 -C 8 alkyl.

5. The compound of claim 1 or pharmaceutically acceptable salts thereof wherein R 1 is C 6 -C 8 alkyl.

6. The compound of claim 1 or pharmaceutically acceptable salts thereof wherein R 1 is aryl optionally substituted with C 1 -C 4 alkyl.

7. The compound of claim 1 or pharmaceutically acceptable salts thereof wherein R 1 is C 1 -C 5 alkylenearyl optionally substituted with C 1 -C 4 alkyl.

8. The compound of claim 1 or pharmaceutically acceptable salts thereof wherein R 1 is aryl optionally substituted with methyl.

9. The compound of claim 1 or pharmaceutically acceptable salts thereof, of the structure

10. A pharmaceutical composition comprising a compound or a pharmaceutically acceptable salt thereof of claim 9 and a pharmaceutically acceptable carrier.

11. The compound of claim 1 or pharmaceutically acceptable salts thereof, of the structure

12. A pharmaceutical composition comprising two or more compounds or pharmaceutically acceptable salts thereof of claim 1 and a pharmaceutically acceptable carrier.

13. The compound or pharmaceutically acceptable salts of claim 1 , wherein R 1 is n-pentyl, n-hexyl, n-heptyl, or n-octyl.

Assignees

• Univ Brigham Young

Inventors

• Kolocouris Antonios
• Busath David D
• Johnson Brent

Classifications

• C07C211/38

  containing condensed ring systems · CPC title

• C07D211/10

  with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms · CPC title

• C07D207/06

  with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07D209/96 Primary

  Spiro-condensed ring systems · CPC title