3′ equatorial-fluorine-substituted neuraminidase inhibitor compounds, compositions and methods for the use thereof as anti-virals

Patent metadata

Field	Value
Publication number	US-9949945-B2
Application number	US-201615243679-A
Country	US
Kind code	B2
Filing date	Aug 22, 2016
Priority date	Jan 19, 2012
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

Abstract

Equatorial 2,3-fluorinated glycosides compounds of formula (I) useful for the treatment or prophylaxis of viral infection, particularly viral influenza, the methods for their preparation, and their pharmaceutical compositions are provided. The therapeutic effect is achieved via inhibition of viral neuraminidases.

First claim

What is claimed is:

1. A method of treating a viral infection comprising administering to a subject in need thereof an effective amount of a compound of formula I:

or an effective amount of a pharmaceutically acceptable salt thereof
wherein
T is COOH or COOEt;
Z is F;
D is F;
X is NHC(NH)NH 2 ;
Q is OH;
E is OH; and
A is OH,

and wherein the viral infection is caused, at least in part, by an influenza virus that is resistant to zanamivir, oseltamivir, or peramivir, or a combination thereof.

2. The method of claim 1 , wherein the influenza virus is resistant to zanamivir.

3. The method of claim 1 , wherein the influenza virus is resistant to oseltamivir.

4. The method of claim 1 , wherein the influenza virus is resistant to peramivir.

5. The method of claim 1 , wherein T is COOH, and wherein the influenza virus is an H1N1, H3N2 or H1N9 subtype.

6. The method of claim 1 , wherein T is COOH, and wherein the influenza virus is resistant to zanamivir.

7. The method of claim 1 , wherein T is COOH, and wherein the influenza virus is resistant to oseltamivir.

8. The method of claim 1 , wherein T is COOH, and wherein the influenza virus is resistant to peramivir.

9. The method of claim 1 , wherein T is COOH, and wherein the influenza virus is an influenza B virus.

10. The method of claim 1 , wherein T is COOEt.

11. The method of claim 10 , wherein the influenza virus is an H1N1, H3N2 or H1N9 subtype.

12. The method of claim 10 , wherein the influenza virus is resistant to zanamivir.

13. The method of claim 10 , wherein the influenza virus is resistant to oseltamivir.

14. The method of claim 10 , wherein the influenza virus is resistant to peramivir.

15. The method of claim 10 , wherein the influenza virus is an influenza B virus.

16. A method of treating a viral infection comprising administering to a subject in need thereof an effective amount of a compound of formula I:

or an effective amount of a pharmaceutically acceptable salt thereof,
wherein
T is COOH or COOEt;
Z is F;
D is F;
X is NHC(NH)NH 2 ;
Q is OH;
E is OH; and
A is OH,

and wherein the viral infection is caused, at least in part, by an influenza B virus.

17. The method of claim 16 , wherein T is COOEt.

Assignees

• Univ British Columbia

Inventors

• Withers Stephen
• Chen Hongming
• Resende Ricardo
• Breschkin Jennifer Lois

Classifications

• A61P31/12

  Antivirals · CPC title

• A61K31/351 Primary

  not condensed with another ring · CPC title

• C07D309/14 Primary

  Nitrogen atoms not forming part of a nitro radical · CPC title

• A61P31/16

  for influenza or rhinoviruses · CPC title