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Semi-synthesis method for preparing antibiotic telithromycin

A technology of telithromycin and a synthesis method, which is applied in the directions of sugar derivatives, bulk chemical production, organic chemistry, etc., to achieve the effects of less by-products, easy separation, and convenient operation

Inactive Publication Date: 2008-08-06
CHENGDU WINS CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The nitric acid oxidation method is also used for desulfhydrylation, which has certain production limitations.

Method used

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  • Semi-synthesis method for preparing antibiotic telithromycin
  • Semi-synthesis method for preparing antibiotic telithromycin
  • Semi-synthesis method for preparing antibiotic telithromycin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Preparation of 3-acetylpyridine oxime (4):

[0032] 10g (82.5mmol) of 3-acetylpyridine (3), methanol (20ml), triethylamine (5g, 495mmol) and hydroxylamine hydrochloride (10g, 143mmol), stirred under reflux for 6.5 hours and cooled to 10°C in an ice bath Next, slowly adjust the pH to 10 with concentrated ammonia water, and solids precipitated out. Continue cooling in an ice bath for 1 hour to crystallize, filter with suction, and dry the filter cake to obtain 10.7 g of white solids, yield 95.2, mp: 114-118°C.

Embodiment 2

[0034] Preparation of 0-p-toluenesulfonyl-3-acetylpyridinium oxime (5):

[0035] 10.3g (75mmol) of 3-acetylpyridine oxime (4) and 36mL of anhydrous pyridine were mixed uniformly under stirring, cooled in an ice bath, 15.7g (82mmol) of p-toluenesulfonyl chloride was added in batches, and the temperature was controlled below 5°C. Then stirred overnight at 0°C, poured into 400g of crushed ice, and filtered to obtain 19.3g of a yellowish solid, yield 88.6%, mp: 77-79°C.

Embodiment 3

[0037] Preparation of 2-amino-1-(3-pyridyl)ethanone dihydrochloride (6):

[0038] Under nitrogen protection, potassium ethylate (6.4g, 76mmol) was added to absolute ethanol (50ml), and after the internal temperature dropped to room temperature, 40mL of 0-p-toluenesulfonyl-3-acetylpyridinium oxime (5) (20g, 68.1mmol) was slowly added ) ethanol suspension, stirred vigorously, a large amount of orange-yellow solid was precipitated, the reaction solution became thicker and thicker, the inner temperature rose to 50°C and then dropped to room temperature for 4 hours of reaction, adding anhydrous diethyl ether (400mL), filtered, and the filter cake was washed with Wash with water and ether, add concentrated HCl (100mL) slowly to the filtrate and lotion, a large amount of orange precipitate precipitates, cool in an ice bath for 1 hour and filter, dry the filter cake and recrystallize with absolute ethanol to obtain 10.5g off-white crystals , yield 78.5%, mp: 171-173°C.

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PUM

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Abstract

The invention relates to a semi-synthetic method for preparing a new antibiotic as telithromycin (I), belonging to pharmacy technical field, which comprises using self-manufactured Fe-V-Ti-ZSM-5 of 3-(2-mercaptoglyoxaline-4-radical) pyridine and hydrogen dioxide solution catalysis oxidization desulfhydro method to prepare high-purity side chain key intermediate compound (II), reacting the compound (II) with abomacetin decorated mother ring (III) protected by benzoyl, removing protective radical (benzoyl) to obtain telithromycin. The preparation method has mild conditions, high product yield and eliminated column chromatography separation purification replaced by simple recrystallization purification, to reduce device investment and reduce cost with simple operation and support for industrial production.

Description

technical field [0001] The invention relates to a semi-synthetic method for preparing antibiotic telithromycin (I), which belongs to the field of pharmacy. Background technique [0002] The novel antibiotic telithromycin produced by Sanofi-Aventis in France is the first novel antibiotic-ketolide antibiotic that has been widely clinically evaluated. Mainly used to treat respiratory infections, bronchitis and pneumonia. Telithromycin was approved in Europe in August 2001 for sale in 15 EU member states, and was approved for marketing in Japan in December 2003. The U.S. FDA approved telithromycin for marketing in the United States in 2004. Telithromycin is a product of the erythromycin series, and the synthesis of telithromycin is quite technically difficult. Currently, the domestic development of this drug has a good market prospect. [0003] The synthetic technique of telithromycin is usually modified parent ring (III) by erythromycin ( figure 1 ) and side chain key interm...

Claims

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Application Information

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IPC IPC(8): C07H17/08
CPCY02P20/55
Inventor 鲁灵江魏峰唐元友罗仕忠林晓琴杨永荣
Owner CHENGDU WINS CHEM
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