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Vaccines against streptococcus pneumoniae serotype 5

一种肺炎、选自的技术，应用在合成糖及其缀合物领域，能够解决疫苗有效制造不利等问题

Active Publication Date: 2018-02-16
MAX PLANCK GESELLSCHAFT ZUR FOERDERUNG DER WISSENSCHAFTEN EV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Heterogeneity of the SP5CPS fragment in terms of size and structure is detrimental for efficient manufacture of well-defined vaccines

Method used

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  • Vaccines against streptococcus pneumoniae serotype 5
  • Vaccines against streptococcus pneumoniae serotype 5
  • Vaccines against streptococcus pneumoniae serotype 5

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0342] Example 1: Synthesis of phenyl 2-azido-2-deoxy-1-seleno-α-D-fucopyranoside (1*)

[0343]

[0344] At -30°C, fucotenose (Bedini, E.et.al.Synlett 2006, 6, 825-830) (4.6g, 21.6mmol) and Ph 2 Se 2 (6.75g, 21.6mmol) To a solution in DCM (70mL) was added PhI(OAc) 2 (6.96 g, 21.6 mmol). TMSN was then added dropwise to the resulting solution 3 (5.74 mL, 43.2 mmol). The solution was warmed to -10°C. The reaction was complete after 4 h at -10 °C. The reaction mixture was warmed to room temperature and washed with NaHCO 3 Wash with saturated solution and then with brine. The solvent was evaporated and the impure was dissolved in MeOH (190 mL). NaOMe 0.5M (4.75 mmol, 9.5 mL) solution was added dropwise to the mixture at room temperature. The reaction was stirred at room temperature for 1 h. Add Amberlite and stir until pH drops to 5. The reaction mixture was filtered and the solvent was evaporated. The residue was purified by silica gel chromatography (DCM 100% to ...

Embodiment 2

[0345] Example 2 : Synthesis of phenyl 2-azido-2-deoxy-3-O-p-methoxybenzyl-1-selenium-α-D-fucopyranoside (2*)

[0346]

[0347] Diol 2* (2.5 g, 7.62 mmol) was coevaporated twice with anhydrous toluene and allowed to dry under high vacuum for 30 min. Anhydrous toluene (80 mL) was then added followed by Bu 2 SnO (2.84 g, 11.43 mmol) and 4AMS. The reaction was stirred at reflux for 1 h. The reaction was cooled to 40 °C; PMBCl (3.11 mL, 22.85 mmol) and TBAB (3.68 g, 11.43 mmol) were added and stirred at room temperature overnight. In the morning the reaction was complete. The reaction was filtered and the solvent was evaporated. The residue was purified by silica gel chromatography (10%-20% EtOAC in hexane). Alcohol 2* was obtained as a yellow oil (3.09 g, 6.89 mmol, 90%). [α] D 20 =+177.4° (c=0.77, CHCl 3 ); IRν max (Film) 3493, 2935, 2111, 1613, 1514, 1249, 1091, 740cm -1 ; 1 H NMR (400MHz, CDCl 3 )δ7.79–7.47(m,2H),7.41–7.12(m,5H),6.92(d,J=8.7Hz,2H),5.88(d,J=5....

Embodiment 3

[0348] Example 3 :Phenyl 2-azido-2-deoxy-3-O-p-methoxybenzyl-4-O-(2-naphthylmethyl)-1-selenium-α-D-fucopyranoside -Synthesis of 2-(bromomethyl)-naphthalene(3*)

[0349]

[0350] 2-(Bromomethyl)-naphthalene (2.8 g, 12.67 mmol) was added to a solution of alcohol 2* (2.84 g, 6.33 mmol) in DMF:THF (1:1, 64 mL). The mixture was then cooled to 0 °C and NaH 60% (304 mg, 7.60 mmol) was added. The reaction was allowed to warm to room temperature and stirred for 1 h. The reaction is complete. It was then cooled to 0°C again and 100 mg of NaH was added. After 1 h the reaction was complete. The reaction mixture was cooled to 0 °C, MeOH was added and the reaction was allowed to warm to room temperature. The reaction mixture was diluted with ether, washed with HCl, NaHCO 3 and washed with brine. The solvent was evaporated and the residue was purified by silica gel chromatography (5%-10% EtOAC in hexane). The product 3* was obtained as a colorless oil (2.56 g, 4.35 mmol, 69%). ...

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PUM

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Abstract

The present invention relates to well-defined synthetic saccharides of general formula (I) that are related to the repeating unit of Streptococcus pneumoniae serotype 5 capsular polysaccharide and conjugates thereof. The conjugates and pharmaceutical compositions containing said conjugates are useful for prevention and / or treatment of diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae serotype 5. Furthermore, the synthetic saccharides of general formula (I) (as represented in the specification) are useful as markerin immunological assays for detection of antibodies against Streptococcus pneumoniae bacteria.

Description

technical field [0001] The present invention relates to well-defined synthetic saccharides of general formula (I) related to the repeating unit of the capsular polysaccharide of Streptococcus pneumoniae serotype 5 and conjugates thereof. The conjugate and the pharmaceutical composition containing the conjugate can be used for preventing and / or treating diseases related to Streptococcus pneumoniae, more specifically for diseases related to Streptococcus pneumoniae serotype 5. Furthermore, synthetic saccharides of general formula (I) can be used as markers in immunological assays for the detection of antibodies against S. pneumoniae bacteria. Background technique [0002] Streptococcus pneumoniae, a Gram-positive sac-shaped bacterium, is a major cause of respiratory infections and can cause severe invasive pneumococcal disease (IPD). More than 90 different pneumococcal serotypes have been described to date. These are classified by the structure of their capsular polysacchari...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/04A61K39/09A61K31/7028A61P31/04
CPCC07H15/04A61K45/06A61K47/6415A61K47/646A61P31/04A61K39/092A61K2039/6037A61K31/702A61K31/7016C07H15/06A61K39/09A61K31/7028A61K2039/55A61K2039/55511
Inventor C·阿尼什M·里斯本C·马丁C·L·佩雷拉P·H·泽贝格尔N·可汗
Owner MAX PLANCK GESELLSCHAFT ZUR FOERDERUNG DER WISSENSCHAFTEN EV
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