Synthetic vaccines against Streptococcus pneumoniae serotype 2
AssigneeMax-Planck-Gesellschaft zur Forderung der Wissenschaften e.V.
InventorsPeter H. Seeberger, Claney Lebev Pereira, Chakkumkal Anish, Naeem Khan, Madhu Emmadi
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Abstract
The present invention relates to a synthetic saccharide of general formula (I) that is related to Streptococcus pneumoniae serotype 2 capsular polysaccharide, a conjugate thereof and the use of said saccharide and conjugate for raising a protective immune response in a human and/or animal host. Furthermore, the synthetic saccharide of general formula (I) is useful as marker in immunological assays for detection of antibodies against Streptococcus pneumoniae type 2 bacteria.
Claims17
A saccharide of general formula (I)
- V*-Ux+3-Ux+2-Ux+1-Ux-O-L-NH2 (I)
- wherein
- x is an integer selected from 1, 2, 3 and 4;
- V*- represents H-, H-Ux-, H-Ux+1-Ux-, H-Ux+2-Ux+1-Ux- or H-Ux+3-Ux+2-Ux+1-Ux-;
- L is selected from
- —CH2—, —(CH2)2—, —(CH2)3—, —(CH2)4—, —(CH2)5—, —(CH2)6—, —(CH2)7—, —(CH2)8—, —(CH2)9—, —(CH2)10—, —CF2—, —(CF2)2—, —(CF2)3—, —(CF2)4—, —(CF2)5—, —(CF2)6—, —(CF2)7—, —(CF2)8—, —(CF2)9—, —(CF2)10—, —(CH2)2—O—(CH2)2—, —CH2—O—(CH2)3—, —(CH2)3O—CH2—, —CH2—O—(CH2)2—, —(CH2)2O—CH2—, —(CH2)3—O—(CH2)2—, —(CH2)2—O—(CH2)3—, —(CH2)4—O—CH2—, —CH2—O—(CH2)4—, -La-, -La-Le-, -La-Lb-Le-, -La-Lb-Ld-Lc-Le-, and -La-Ld-Le-;
- wherein
- -La- is selected from:
- —(CH2)o—, —(CF2)o—, —(CH2—CH2—O)o—C2H4—, —(CH2—CH2—O)o—CH2—, —(CR10R11)o—,
- -Lb- and -Lc- are independently of each other selected from:
- —O—, —NH—C(O)—NH—, —NH—C(S)—NH—, —NH—C(O)—, —C(O)—NH—, —NH—C(O)—O—, —NR9—, —NR18—, —SO2—,
- -Ld- represents —(CH2)q—, —(CF2)q—, —(CR12R13)q—, —(CH2—CH2—O)q—C2H4—, —CH2—CH2—O)q—CH2—,
- -Le- is selected from:
- —(CH2)p1—, —(CF2)p1—, —C2H4—(O—CH2—CH2)p1—, —CH2—(O—CH2—CH2)p1—, —(CH2)p1—O—(CH2)p2—, —(CR14R15)p1—, —(CR14R15)p1—O—(CR21R22)q2—,
- R9 and R18 are independently of each other selected from:
- —CH3, —C2H5, —C3H7, and —C(O)CH3;
- R10, R11, R12, R13, R14, R15, R16, R17, R19, R20, R21 and R22 are independently of each other selected from:
- —H, —F, —Cl, —CH3, —C2H5, —C3H7, —C5H9, —C6H13, —OCH3, —OC2H5, —CH2F, —CHF2, —CF3, —C(O)—NH2, —SCH3, —SC2H5, —NHC(O)CH3, —N(CH3)2 and —N(C2H5)2;
- o, q, p1 and p2 are independently of each other an integer selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10;
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.