Vaccine against klebsiella pneumoniae
AssigneeIdorsia Pharmaceuticals Ltd
InventorsFelix BROECKER, Claney Lebev PEREIRA, Sharavathi Guddehalli PARAMESWARAPPA, Arne VON BONIN
Life of this patent
Estimating the term…
Abstract
The present invention relates to novel oligosaccharide-carrier protein conjugates of Formula (I), and their use as pharmaceuticals, in particular as vaccines. The invention also concerns related aspects including oligosaccharide intermediates of Formulae (II) and (III), as well as processes for the preparation of the conjugates. Furthermore, the invention relates to pharmaceutical compositions comprising the oligosaccharide-carrier protein conjugates, as well as the use of the oligosaccharide-carrier protein conjugates of Formula (IV) in biological assays.
Claims38
An oligosaccharide-carrier protein conjugate of formula (I)
- wherein
- m is 4, 5 or 6;
- n is 5, 6 or 7;
- i is from 1 to 28;
- and
- -L-T-represents a linker L and a spacer T which together form a bridge having a backbone with a length of 5 to 25 atoms covalently linked together that forms the shortest distance between the oxygen at C1 of the reducing end of the oligosaccharide and the nitrogen of the amino group of a lysine residue at the carrier protein CRM197, wherein the atoms of the backbone are selected from the group consisting of carbon, nitrogen, oxygen and sulphur;
- or a pharmaceutically acceptable salt thereof.
(canceled)
A compound having the formula (II)
- wherein
- m is 4, 5 or 6, preferably 4 or 5, more preferably 4;
- n is 5, 6 or 7, preferably 6 or 7, more preferably 6;
- L1 represents
- *—(C2-10)alkylene-NH2, preferably *—(CH2)l—NH2;
- wherein l is from 2 to 10, more preferably l is 5;
- *—(CH2CH2O)a—CH2CH2NH2, wherein a is 1, 2 or 3;
- *—CH2CH2S—CH2CH2NH2;
- *—(C2-10)fluoroalkylene-NH2;
- *—(CH2)cNHC(O)(CH2)d—NH2, wherein c and d are independently from each other from 2 to 6;
- *—(CH2)eNHC(O)NH(CH2)h—NH2, wherein e and h are independently from each other from 2 to 6;
- *—(C1-10)alkylene-C(O)—NH—(C2-10)alkylene-NH2;
- *—(C2-10)alkylene-O—NH2;
- or
- *—(C2-10)alkylene-SH;
- or a pharmaceutically acceptable salt thereof.
A compound having the formula (III)
- wherein
- m is 4, 5 or 6, preferably m is 4 or 5, most preferably 4;
- n is 5, 6 or 7, preferably n is 6 or 7, most preferably 6;
- L represents
- *—(C2-10)alkylene-NH—, preferably *—(CH2)l—NH— wherein l is from 2 to 10, more preferably 5;
- *—(CH2CH2O)a—CH2CH2NH—, wherein a is 1, 2 or 3;
- *—CH2CH2S—CH2CH2NH—;
- *—(C2-10)fluoroalkylene-NH—;
- *—(CH2)cNHC(O)(CH2)d—NH—, wherein c and d are independently from each other from 2 to 6;
- *—(CH2)eNHC(O)NH(CH2)h—NH—, wherein e and h are independently from each other from 2 to 6;
- *—(C1-10)alkylene-C(O)—NH—(C2-10)alkylene-NH—;
- or
- *—(C2-10)alkylene-O—NH—;
- T1 represents
- —C(O)—(C0-10)alkylene-C(O)X;
- —C(O)—CH2CH2—(OCH2CH2)r—C(O)X, wherein r is from 1 to 5;
- —C(O)—CH2(CH2)f(SCH2(CH2)f′)f″—C(O)X, wherein f is 0 or 1, f′ is 0 or 1, and f″ is
- 1, 2, or 3;
- wherein w is 1 or 2;
- or
- wherein j is from 1 to 4, preferably 1, and s is 1 or 2;
- —C(O)X represents —C(O)OH or an activated ester, wherein preferably
- X represents
- and
- Y represents Me, Et, Bu or —(CH2CH2O)3CH3,
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.