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A preparation process of a clarithromycin impurity O or similar compounds

A technology of clarithromycin and preparation process, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of less reports on the preparation process of impurities, and achieves high product yield, good purity, and easy production. The effect of crystallization

Active Publication Date: 2013-08-07
HEC PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] With the improvement of advanced testing levels at home and abroad, higher requirements are put forward for the quality of clarithromycin. At present, the domestic pharmacopoeia has not yet made qualitative analysis requirements for some impurities of clarithromycin, and there are few reports on the preparation process of related impurities.

Method used

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  • A preparation process of a clarithromycin impurity O or similar compounds
  • A preparation process of a clarithromycin impurity O or similar compounds
  • A preparation process of a clarithromycin impurity O or similar compounds

Examples

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Effect test

Embodiment 1

[0021] In a 250ml reaction flask, add clarithromycin oximide 10g (13.4mmol), methanol 150ml., stir to dissolve, add 3.82g (40mmol) methyl bromide, sodium hydroxide 1.6g (40mmol), react at 80°C for 1 hour, and react Finished, filter with suction, concentrate the filtrate under reduced pressure at 40°C, remove methanol, dissolve the residue with 20ml of acetone, control the temperature at 35°C, slowly add 30ml of water dropwise, until the solid precipitates, keep warm for 1 hour, drop to 8°C, and filter with suction , and the filter cake was vacuum-dried at 45°C to obtain 3.8 g of white solid I. Yield 38%, content 98.6%.

Embodiment 2

[0023] In a 250ml reaction flask, add 10g (13.4mmol) of clarithromycin oxime, 100ml of methylene chloride, stir to dissolve, add 3.32g (20mmol) of potassium iodide, 1.68g (20mmol) of sodium bicarbonate, and react at 0°C for 24 hours , the reaction was completed, suction filtered, concentrated the filtrate under reduced pressure at 40°C, recovered dichloromethane, dissolved the residue with 10ml of acetone, controlled the temperature at 35°C, and slowly added 30ml of water until the solid precipitated. °C, filter with suction, and dry the filter cake in vacuum at 45 °C to obtain 4.5 g of white solid I. The yield is 45%, and the content is 98.4%.

Embodiment 3

[0025] In a 250ml reaction flask, add 10g (13.4mmol) of clarithromycin oximide and 200ml of acetone, stir to dissolve, add 6.64g (40mmol) of potassium iodide, 1.6g (40mmol) of sodium hydroxide, react at 20°C for 6 hours, and the reaction ends , filter with suction, concentrate the filtrate under reduced pressure at 40°C, recover acetone, dissolve the residue with 10ml of acetone, control the temperature at 35°C, slowly add 30ml of water dropwise until the solid precipitates, keep it warm for 1 hour, lower it to 8°C, and filter with suction. The filter cake was vacuum-dried at 45°C to obtain 2.8 g of white solid I. The yield is 28%, and the content is 98.7%.

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Abstract

A preparation process of a clarithromycin impurity O or similar compounds comprises: dissolving clarithromycin intermediates or oximation products (II) of B, C, D, E, F components as raw materials in a lower alcohol, a lower ketone or a halogenated hydrocarbon; and with methyl iodide, methyl bromide, or dimethyl sulfate as a methyl agent, and with the action of an acid-binding agent, subjecting to a methylation reaction at a temperature between 0-80 DEG C for 1 to 24 hours, after the reaction is completed, filtering, concentrating mother liquor under reduced pressure, and refining the residue in a mixed system of a lower alcohol with water or a mixed system of a lower ketone with water. The present invention provides a novel preparation process of the clarithromycin impurity O or similar compounds, the product yield is high, the purity is good, the crystallization is easy, and the purification is convenient.

Description

technical field [0001] The invention relates to a preparation process of clarithromycin impurity O and similar compounds. Background technique [0002] The structural formula of clarithromycin 81103-11-9 is: [0003] [0004] Clarithromycin is a broad-spectrum macrolide antibiotic. It has inhibitory effect on Gram-positive bacteria such as Staphylococcus aureus, Streptococcus, Pneumococcus, etc., and has inhibitory effect on some Gram-negative bacteria such as Haemophilus influenzae, Bordetella pertussis, Neisseria gonorrhoeae, Legionella pneumophila and some anorexia Oxygen bacteria such as Bacteroides fragilis, Peptostreptococcus, Propionibacterium acnes, etc. also have inhibitory effects, and also have inhibitory effects on mycoplasma. It has definite curative effect and low toxic and side effects. [0005] With the improvement of advanced detection level at home and abroad, higher requirements are put forward for the quality of clarithromycin. At present, the domes...

Claims

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Application Information

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IPC IPC(8): C07H17/08C07H1/00
Inventor 陈黎明唐金龙张俊山关健平
Owner HEC PHARM
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