US 10,376,593 B2
Glycoconjugates and their use as potential vaccines against infection by Shigella flexneri
Laurence Mulard, Le Kremlin Bicetre (FR); Pierre Chassagne, Beaumont (FR); Philippe Sansonetti, Paris (FR); Armelle Phalipon, Paris (FR); Francois Traincard, Issy-les-moulineaux (FR); and Farida Nato, Antony (FR)
Appl. No. 14/438,750
Filed by INSTITUT PASTEUR, Paris (FR); CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, Paris (FR); INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE, Paris (FR); and UNIVERSITE PARIS DESCARTES, Paris (FR)
PCT Filed Oct. 29, 2013, PCT No. PCT/EP2013/072651
§ 371(c)(1), (2) Date Apr. 27, 2015,
PCT Pub. No. WO2014/067970, PCT Pub. Date May 8, 2014.
Claims priority of application No. 12306351 (EP), filed on Oct. 29, 2012.
Prior Publication US 2015/0290331 A1, Oct. 15, 2015
Int. Cl. A61K 47/64 (2017.01); A61K 9/127 (2006.01); A61K 38/16 (2006.01); C07K 17/10 (2006.01); A61K 47/54 (2017.01)
CPC A61K 47/646 (2017.08) [A61K 9/1271 (2013.01); A61K 38/164 (2013.01); A61K 47/549 (2017.08); C07K 17/10 (2013.01); C07K 2317/76 (2013.01); Y02A 50/475 (2018.01)] 18 Claims
 
1. A vaccine composition comprising a physiologically acceptable vehicle and a conjugate comprising an oligo- or polysaccharide selected from the group consisting of:
(X)x-{BCDA}n-(Y)y
(X)x-{CDAB}n-(Y)y
(X)x-{DABC}n-(Y)y
(X)x-{ABCD}n-(Y)y
wherein:
n is an integer comprised between 2 and 10,
A is a beta-d-Galacturonic acid (1,3) residue,
B is a N-acetyl-beta-d-Galactosamine (1,2) residue,
C is independently, at each occurrence, an alpha-I-Rhamnose (1,2) residue, wherein at most one of its 3c or 4c positions is OAc (i.e O—C(═O)CH3), provided that there is at least one occurrence of C wherein the 3c position is not OAc, and provided that when C is a non reducing end residue, its 2c position may be acetylated or not,
D is an alpha-I-Rhamnose (1,4) residue,
x and y are independently selected among 0 and 1,
X and Y are independently selected among A, B, C, D, AB, BC, CD, DA, ABC, BCD, CDA, DAB,
provided that the ratio of 3C-OAc/4C-OAc is greater than 1,
said oligo- or polysaccharide being bound to a carrier.