Vaccine against klebsiella pneumoniae
AssigneeIdorsia Pharmaceuticals Ltd
InventorsFelix BROECKER, Sharavathi Guddehalli PARAMESWARAPPA, Claney Lebev PEREIRA, Marilda P. LISBOA, Arne VON BONIN
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Abstract
The present invention relates to novel immunogenic compounds comprising at least one antigen of Formula (I), in particular immunogenic compounds of Formula (II), and their use as pharmaceuticals, in particular as vaccines. The invention also concerns related aspects including intermediates, as well as processes for the preparation of the immunogenic compounds. Furthermore, the invention relates to pharmaceutical compositions comprising the immunogenic compounds, as well as the use of the antigen of Formula (I) in biological assays.
Claims30
An immunogenic compound comprising at least one oligosaccharide hybrid antigen having the structure of formula (I)
- wherein
- R is OH, or
- m is 3, 4, 5, 6, 7 or 8;
- and
- n is 1, 2, 3, 4, 5 or 6;
- or a pharmaceutically acceptable salt thereof.
An immunogenic compound of formula (II)
- wherein
- R is OH, or
- m is 3, 4, 5, 6, 7 or 8;
- n is 1, 2, 3, 4, 5 or 6;
- 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 structure of formula (III):
- wherein
- R is OH, or
- m is 3, 4, 5, 6, 7 or 8;
- preferably 3, 4, 5 or 6;
- n is 1, 2, 3, 4, 5 or 6;
- preferably 2, 3, or 4;
- L1 represents
- *—(C2-10)alkylene-NH2, preferably *—(CH2)a—NH2;
- wherein a is from 2 to 10, more preferably l is 5;
- *—(CH2CH2O)b—CH2CH2NH2, wherein b is 1, 2 or 3;
- *—CH2CH2S—CH2CH2NH2;
- *—(C2-10)fluoroalkylene-NH2;
- *—(CH2)cNHC(O)(CH2)c′—NH2, wherein c and c′ are independently from each other from 2 to 6;
- *—(CH2)dNHC(O)NH(CH2)d′—NH2, wherein d and d′ 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 structure of formula (IV):
- wherein
- R is OH, or
- m is 3, 4, 5, 6, 7 or 8;
- preferably 3, 4, 5 or 6;
- n is 1, 2, 3, 4, 5 or 6;
- preferably 2, 3, or 4;
- L represents
- *—(C2-10)alkylene-NH—, preferably *—(CH2)a—NH— wherein a is from 2 to 10, more preferably 5;
- *—(CH2CH2O)b—CH2CH2NH—, wherein b is 1, 2 or 3;
- *—CH2CH2S—CH2CH2NH—;
- *—(C2-10)fluoroalkylene-NH—;
- *—(CH2)cNHC(O)(CH2)c′—NH—, wherein c and c′ are independently from each other from 2 to 6;
- *—(CH2)dNHC(O)NH(CH2)d′—NH—, wherein d and d′ 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)j—C(O)X, wherein j is from 1 to 5;
- —C(O)—CH2(CH2)k—(SCH2(CH2)k′)k″—C(O)X, wherein k is 0 or 1, k′ is 0 or 1, and k″ is 1, 2, or 3;
- wherein l is 1 or 2;
- or
- wherein p is from 1 to 4, preferably 1, and
- p′ 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.
Dependencies are inferred from the claim text.