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Novel HCV virus NS3/4A inhibitor synthesizing intermediate and synthesis method

A synthetic method and inhibitor technology, applied in the direction of organic chemistry, can solve the problems of low product yield and high raw material cost, and achieve the effect of high synthetic yield, low raw material cost and reduced raw material input

Inactive Publication Date: 2019-04-26
NANJING XIAOZHUANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented method involves reacting 2-(dimethoxysilyl)-Naphthalene with bromine under specific conditions for producing hydroxymethanesulfonic acid monosodium salt or its salts that are useful intermediates used in pharmaceuticals such as clonidone. These methods have been developed at an affordable price compared to previous techniques like chemical reactions involving expensive starting products. Additionally, these modifications make it easier than previously possible to produce more pure product without adding unnecessary substances. Overall this technology provides technical benefits over existing processes.

Problems solved by technology

This patented describes different ways how drugs like vanapiris can be used against viruses called HepC Virus that cause acute or persistently sicknesses. However it was discovered during researchers' experiments with other compounds found similar effects when they were tested at MHV laboratories over time.

Method used

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  • Novel HCV virus NS3/4A inhibitor synthesizing intermediate and synthesis method
  • Novel HCV virus NS3/4A inhibitor synthesizing intermediate and synthesis method
  • Novel HCV virus NS3/4A inhibitor synthesizing intermediate and synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048]

Embodiment 2

[0051]

[0052] Add CCl to the 5L reaction flask 4 1.5L, add compound IV 120g, add 2g AIBN, add NBS1.1eq in batches, under the protection of nitrogen, heat up to 85°C and reflux reaction overnight. TLC detects that the reaction of raw materials is complete. The reaction solution was cooled to room temperature, poured into an aqueous solution of sodium thiosulfate, separated the organic phase, extracted the aqueous phase with MTBE, washed the organic phase three times with aqueous sodium thiosulfate, washed twice with saturated aqueous sodium chloride, and anhydrous Dry over sodium sulfate and concentrate. The residue was separated and purified by column chromatography, eluent PE (petroleum ether): EA (ethyl acetate) = 40:1-20:1 to obtain the crude product, and then the crude product was distilled under reduced pressure, 2 Torr, external temperature 168°C, internal temperature 120°C. 110 g of compound III was obtained as a colorless liquid.

Embodiment 3

[0054]

[0055] The compound III obtained in Example 2 was added to the freshly prepared 10M ammonia methanol solution, and stirred overnight. When no white solid is precipitated, filter and drain to obtain 60 g of off-white product. 1 H NMR (400MHz, DMSO) δ8.85(s, 1H), 7.84(d, J=7.8Hz, 1H), 7.73(d, J=7.4Hz, 1H), 7.49(t, J=7.6Hz, 1H ),4.34(s,2H).

[0056] NMR identification of this type of white product was confirmed as compound Ⅱ.

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Abstract

The invention relates to a synthesis method of a medicinal intermediate, and belongs to the field of synthesis of medicines. According to the synthesis method, 4-bromoisoindoline (hydrochloride) is synthesized from 3-bromo-2-methyl-benzoic acid as a raw material. Not only is the raw material cost low, but also a preparation technology is simple, the synthesis yield is high, and industrial application and popularization values are achieved; meanwhile, the stability of the raw material of the intermediate can be improved through one-step t-butyloxycarbonylation, so that the addition amount of the raw material in the synthesis process is reduced, the cost is further reduced, and the synthesis yield is improved.

Description

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Claims

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Application Information

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Owner NANJING XIAOZHUANG UNIV