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Toll-like receptor ligands

A technology of -O-C, -OSO3H, applied in pharmaceutical formulations, antibody medical components, viruses/bacteriophages, etc., can solve problems such as low efficacy, hindered use, poor stability, etc.

Pending Publication Date: 2020-10-30
英尼穆内公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Heterogeneity, low potency, and poor stability of MPL and other naturally derived or synthetic TLR4 ligands hinder their use in many indications

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0325] 2-[(R)-3-Decanoyloxytetradecanoylamino]ethyl 2,3-bis-[(R)-3-Decanoyloxytetradecanoylamino]-2,3-di Preparation of deoxy-4-O-phosphono-β-D-allopyranoside (allopyranoside) (compound 1)

[0326]

example 1

[0329] 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-β-D-glucopyranose hydrochloride (76.47 g, 0.23 mol) was dissolved in dichloromethane (350 mL) and H 2 The solution in O (350 mL) was treated with sodium bicarbonate (149.94 g, 1.79 mol) added slowly in portions. Benzyl chloroformate (79.17 g, 0.46 mol) was added portionwise to control gas evolution and the reaction was stirred vigorously for 2.5 hours. The layers were separated, and the aqueous layer was extracted with dichloromethane (100 mL). The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated to about 100 mL. Methyl tert-butyl ether (200 mL) was added and the resulting mixture was stirred and cooled to 0 °C and the precipitate was collected by filtration, washed with cold methyl tert-butyl ether and dried in a vacuum oven to give 88.89 g (81%) of 1,3,4,6-tetra-O-acetyl-2-(benzyloxycarbonylamino)2-deoxy-β-D-glucopyranoside.

example 1

[0331] The compound prepared in Example 1A above (10 g, 20.8 mmol) and benzyl N-(2-hydroxyethyl)carbamate (4.48 g, 22.9 mmol) cooled to -15 °C were dissolved in anhydrous dichloromethane (80 mL) The solution in , was treated dropwise with trimethylsilyl triflate (0.37 mL, 2.08 mmol). The reaction mixture was allowed to warm to room temperature over 5.5 hours. The reaction was quenched with saturated aqueous sodium bicarbonate (40 mL), and the layers were separated. The aqueous layer was extracted with dichloromethane (2 x 20 mL), and the combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product obtained was crystallized from dichloromethane / heptane to give 10.4 g (81%) of 2-(benzyloxycarbonylamino)ethyl 3,4,6-tri-O-acetyl-2- Benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside as a white solid.

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PUM

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Abstract

Toll-like receptor (TLR) ligands having an allose-based core are stable in aqueous formulation and are useful in treating, preventing, or reducing susceptibility to diseases or conditions mediated byTLRs, such as cancer, infectious disease, allergy, autoimmune disease, sepsis, and ischemia reperfusion.

Description

[0001] related application [0002] This application claims priority to U.S. Provisional Application No. 62 / 629,513, filed February 12, 2018, which is hereby incorporated by reference in its entirety. [0003] Statement of Government Interest [0004] This invention was made with government support under Grant No. 1R43AI136081-01A1 awarded by the National Institute of Allergy and Infectious Diseases. The government has certain rights in this invention. technical field [0005] The present invention relates to Toll-like receptor ligands useful in the treatment of diseases or conditions mediated by Toll-like receptors. Background technique [0006] Gram-negative bacteria have long been known to elicit immune responses via Toll-like receptors (TLRs). Unique structural components characteristic of these pathogens are associated with efficient innate and adaptive immune responses. Development of agonists and antagonists of TLRs as pharmacological manipulation of the innate im...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K39/02A61K39/39A61P31/04
CPCA61K39/39A61P31/04A61K39/12C12N2760/16134A61K2039/55511A61K45/06A61K31/7008C07H15/12C07H15/04A61K2300/00A61K39/00C07H15/26A61P31/00C07H15/14A61K39/35A61P27/02A61K2039/57A61P25/08A61P35/00A61P17/04A61P37/00A61P9/10A61P11/02
Inventor H·巴津-李G·埃廷格J·哈拉夫K·T·瑞特
Owner 英尼穆内公司
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