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Tlr agonists

A compound and alkyl technology, which can be used in antiviral agents, allergic diseases, antibacterial drugs, etc., and can solve the problem of reducing auxiliary effects

Inactive Publication Date: 2008-11-12
RGT UNIV OF CALIFORNIA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

) Although TLR agonists (TLR-L) may be sufficiently active for some therapeutic approaches, in some cases microbial interferon antagonists can reduce the adjuvant effect of synthetic TLR-L

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0154] Example 1 The preparation of 4-(2,6-dichloropurin-9-ylmethyl)benzonitrile

[0155] 2,6-Dichloro-9H-purine (16 mmol) was dissolved in DMF (50 mL) and potassium carbonate (50 mmol) was added. α-Bromo-p-tolylcyanide (22 mmol) was then added, and the mixture was stirred at room temperature for 16 h. After removal of insoluble inorganic salts by filtration, the filtrate was poured into water (1500 mL) and extracted with ethyl acetate (2 x 400 mL), dried over magnesium sulfate and evaporated to give a residue which was obtained by using 1:2:10 ethyl acetate Flash chromatography on silica gel of esters / acetone / hexanes. Yield 3.33 g (69%). UV, NMR and MS were consistent with the assigned structure.

Embodiment 2

[0156] Example 2 Preparation of 4-(6-amino-2-chloropurin-9-ylmethyl)benzonitrile

[0157] The product of Example 1 (1.9 g) was placed in a steel reaction vessel and methanolic ammonia (80 mL, 7N) was added. The sealed vessel was heated at 60 °C for 12 h, cooled in ice and the solid product was filtered off. Yield 1.09 g. UV, NMR and MS were consistent with the assigned structure.

Embodiment 3

[0158] Example 3 Preparation of 4-[6-amino-2-(2-methoxyethoxy)purin-9-ylmethyl]benzonitrile

[0159] The sodium salt of 2-methoxyethanol was produced by dissolving metallic sodium (81 mg) in 2-methoxyethanol (30 mL) with heating. To this solution was added the product of Example 2 (1.0 g) dissolved in methoxyethanol (300 mL, heated). The reaction mixture was heated at 115 °C bath temperature for 8 h, concentrated in vacuo to near dryness, and the residue was partitioned with ethyl acetate and water. The organic layer was purified by flash chromatography on silica gel using 5% methanol in dichloromethane to afford 763 mg of product. NMR was consistent with the assigned structure.

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Abstract

The present invention provides TLR agonist conjugates (compounds) and compositions, as well as methods of using them. The compounds of the invention are broad-spectrum, long-lasting, and non-toxic combination of synthetic immunostimulatory agents, which are useful for activating the immune system of a mammal, preferably a human and can help direct the pharmacophore to the receptor within the endosomes of target cells and enhance the signal transduction induced by the pharmacophore.

Description

[0001] related application [0002] This application claims priority from US Provisional Application Serial No. 60 / 710,337, filed August 22, 2005, the contents of which are incorporated herein by reference. [0003] Government funding [0004] The invention described herein was made with Government Grant No. 3 UO1 AI056453-01 awarded by the National Institutes of Health. The US Government has certain rights in this invention. Background technique [0005] Much has been learned in the last decade about the molecular mechanisms of innate recognition of microbial pathogens. It is generally accepted that many somatic cells express a variety of pattern recognition receptors that detect potential pathogens independent of the adaptive immune system. (See Janeway et al., Annu Rev Immunol, 20: 197-216 (2002).) The receptors are thought to interact with microbial components known as pathogen-associated molecular patterns (PAMPs). Examples of PAMPs include peptidoglycan, lipoteich...

Claims

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Application Information

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IPC IPC(8): A61K31/522C07D473/10
CPCC07D473/16C07D473/18C07D473/24A61P1/04A61P17/00A61P19/02A61P31/04A61P31/12A61P31/14A61P31/20A61P35/00A61P35/02A61P37/02A61P37/06A61P43/00C07D473/34
Inventor D·A·卡森K·高林H·B·科塔姆M·陈吴正宁
Owner RGT UNIV OF CALIFORNIA
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