Vaccine against Klebsiella pneumoniae

A saccharide of general formula (II-8) or (II-11):

• wherein
• n is an integer from 1 to 20;
• -L-E represents -La-E, -La-Le-E, -La-Lb-Le-E, or -La-Ld-Le-E;
• wherein
• -La- represents —(CH2)o—, —(CH2—CH2—O)o—C2H4—, or —(CH2—CH2—O)o—CH2;
• -Lb- represents —O—, —NH—CO—NH—, —NH—CO—CH2—NH—, or —NH—CO—;
• -Ld- represents —(CH2)q—, —(CH(OH))q—, —(CF2)q—, —(CH2—CH2—O)q—C2H4—, or —(CH2—CH2—O)q—CH2—;
• -Le- represents —(CH2)p1—, —(CF2)p1—, —C2H4—(O—CH2—CH2)p1—, —CH2—(O—CH2—CH2)p1—, or —(CH2)p1—O—(CH2)p2—;
• and
• E represents —NH2, —N3, —O—NH2, —CH═CH2, —C≡CH, —Br, —Cl, —I, —COOH, —COOCH3, —COOC2H5, —CO2R′, —CO-(3-sulfo-N-hydroxysuccinimidyl), —CO-(dibenzocyclooctyne-sulfo-N-hydroxysuccinimidyl), —CONH—NH2, —OH, or —SH;
• R′ represents
• o, q, p1 and p2 are independently of each other an integer selected from 1,
• 2, 3, 4, 5, and 6, with the proviso that -L-E is not —C3H6—NH2;
• or a pharmaceutically acceptable salt thereof.

A conjugate of general formula (III-4):

• wherein
• R′ represents H or U6,
• U6 represents
• n is an integer from 1 to 20;
• m is an integer from 1 to 20;
• -L- represents -La-, -La-Le-, -La-Lb-Le-, or -La-Ld-Le-;
• -La- represents —(CH2)o—, —(CH2—CH2—O)o—C2H4—, or —(CH2—CH2—O)o—CH2;
• -Lb- represents —O—, —NH—CO—NH—, —NH—CO—CH2—NH—, or —NH—CO—;
• -Ld- represents —(CH2)q—, —(CH(OH))q—, —(CF2)q—, —(CH2—CH2—O)q—C2H4—, or —(CH2—CH2—O)q—CH2—;
• -Le- represents —(CH2)p1—, —(CF2)p1—, —C2H4—(O—CH2—CH2)p1—, —CH2—(O—CH2—CH2)p1—, or —(CH2)p1—O—(CH2)p2—;
• and
• o, q, p1 and p2 are independently of each other an integer selected from 1, 2, 3, 4, 5, and 6;
• E1- represents a covalent bond, —NH—, —O—NH—, —O—, —S—, —CO—,
• —CH═CH—, —CONH—, —CO—NHNH—,
• -T- represents
• a represents an integer from 1 to 10;
• b represents an integer from 1 to 4;
• i is an integer selected from 2 to 25;
• CP is a carrier protein selected from the group consisting of:
• a diphtheria toxoid, a mutated diphtheria toxoid, a modified diphtheria toxoid, a mutated and modified diphtheria toxoid, a tetanus toxoid, a modified tetanus toxoid, a mutated tetanus toxoid, outer membrane protein (OMP), bovine serum albumin (BSA), keyhole limpet hemocyanine (KLH), recombinant non-toxic form of Pseudomonas aeruginosa (rEPA) and cholera toxoid (CT).

A conjugate of general formula (III-8) or (III-11):

• wherein
• n is an integer from 1 to 20;
• -L- represents -La-La-Le-, -La-Lb-Le-, or -La-Ld-Le-;
• -La- represents —(CH2)o—, —(CH2—CH2—O)o—C2H4—, or —(CH2—CH2—O)o—CH2;
• -Lb- represents —O—, —NH—CO—NH—, —NH—CO—CH2—NH—, or —NH—CO—;
• -Ld- represents —(CH2)q—, —(CH(OH))q—, —(CF2)q—, —(CH2—CH2—O)q—C2H4—, or —(CH2—CH2—O)q—CH2—;
• -Le- represents —(CH2)p1—, —(CF2)p1—, —C2H4—(O—CH2—CH2)p1—, —CH2—(O—CH2—CH2)p1—, or —(CH2)p1—O—(CH2)p2—;
• and
• o, q, p1 and p2 are independently of each other an integer selected from 1, 2, 3, 4, 5, and 6;
• -E1- represents a covalent bond, —NH—, —O—NH—, —O—, —S—, —CO—, —CH═CH—, —CONH—, —CO—NHNH—,
• -T- represents
• a represents an integer from 1 to 10;
• b represents an integer from 1 to 4;
• and
• i is an integer selected from 2 to 25;
• CP is a carrier protein selected from the group consisting of:
• a diphtheria toxoid, a mutated diphtheria toxoid, a modified diphtheria toxoid, a mutated and modified diphtheria toxoid, a tetanus toxoid, a modified tetanus toxoid, a mutated tetanus toxoid, outer membrane protein (OMP), bovine serum albumin (BSA), keyhole limpet hemocyanine (KLH), recombinant non-toxic form of Pseudomonas aeruginosa (rEPA) and cholera toxoid (CT).

A conjugate of general formula (III-4):

• wherein
• R1 represents H or U6,
• U6 represents
• n is an integer from 1 to 20;
• m is an integer from 1 to 20;
• -L- represents -La-, -La-Le-, -La-Lb-Le, or -La-Ld-Le-;
• -La- represents —(CH2)o—, —(CH2—CH2—O)o—C2H4—, or —(CH2—CH2—O)o—CH2;
• -Lb- represents —O—, —NH—CO—NH—, —NH—CO—CH2—NH—, or —NH—CO—;
• -Ld- represents —(CH2)q—, —(CH(OH))q—, —(CF2)q—, —(CH2—CH2—O)q—C2H4—, or —(CH2—CH2—O)q—CH2—;
• -Le- represents —(CH2)p1—, —(CF2)p1—, —C2H4—(O—CH2—CH2)p1—, —CH2—(O—CH2—CH2)p1—, or —(CH2)p1—O—(CH2)p2—;
• and
• o, q, p1 and p2 are independently of each other an integer selected from 1, 2, 3, 4, 5, and 6;
• -E1- represents a covalent bond, —NH—, —O—NH—, —O—, —S—, —CO—, —CH═CH—, —CONH—, —CO—NHNH—,
• -T- represents
• a represents an integer from 1 to 10;
• b represents an integer from 1 to 4;
• i is an integer selected from 2 to 25;
• and
• CP is a carrier protein selected from the group consisting of:
• a diphtheria toxoid, a mutated diphtheria toxoid, a modified diphtheria toxoid, a mutated and modified diphtheria toxoid, a tetanus toxoid, a modified tetanus toxoid, a mutated tetanus toxoid, outer membrane protein (OMP), bovine serum albumin (BSA), keyhole limpet hemocyanine (KLH), recombinant non-toxic form of Pseudomonas aeruginosa (rEP A) and cholera toxoid (CT),
• wherein the conjugate is prepared by conjugating a saccharide of general formula (II-4):
• to the carrier protein (CP).