2,3-Fluorinated glycosides as neuraminidase inhibitors and their use as anti-virals

Patent metadata

Field	Value
Publication number	US-9604954-B2
Application number	US-201514946132-A
Country	US
Kind code	B2
Filing date	Nov 19, 2015
Priority date	Jul 15, 2009
Publication date	Mar 28, 2017
Grant date	Mar 28, 2017

Abstract

Compounds having a structure of Formula I and compositions comprising these compounds are provided. Uses of such compounds and compositions are provided for treatment or prophylaxis of viral infection. In particular, compounds and compositions may be for use in the treatment or prophylaxis of viral influenza.

First claim

What is claimed is:

1. A method of preparing compound 12:

the method comprising:
mixing compound 2:

with NaOMe and MeOH;
then mixing with AcOH until neutral;
then mixing with PMe 3 , H 2 O, and MeOH; and
then reacting with compound VII:

in Et 3 N, MeOH, and DMF to produce compound VIII:

reacting compound VIII with LiOH, H 2 O, and THF;
then reacting with Pd/C, H 2 , H 2 O, and THF.

Assignees

• Univ British Columbia

Inventors

• Withers Stephen
• Watts Andrew Graham
• Kim Jin Hyo
• Wennekes Tom

Classifications

• C07H15/12

  attached to a nitrogen atom of the saccharide radical · CPC title

• C07H15/18

  Acyclic radicals, substituted by carbocyclic rings · CPC title

• C07H13/12

  by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid · CPC title

• C07D309/14 Primary

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

• A61K31/655

  Azo (—N=N—), diazo (=N2), azoxy (>N—O—N< or N(=O)—N<), azido (—N3) or diazoamino (—N=N—N<) compounds · CPC title