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Etimicin sulfate preparation method

A technology of etimicin sulfate and sodium carbonate, applied in the field of medicine, can solve the problems of poor selectivity of protective groups, many impurities in intermediates, and high industrialization cost, and achieve the effects of short reaction time, simple conditions and easy operation.

Active Publication Date: 2014-12-24
QILU PHARMA HAINAN +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The above patents all adopt the synthesis method of metal ion complexation and then protection. The protection group selectivity of this method is poor, the prepared intermediate has more impurities, and the yield is not high; it also faces environmental problems such as heavy metal pollution; at the same time, the above synthesis methods Higher cost of industrialization

Method used

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  • Etimicin sulfate preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 25g of gentamicin C with a purity of not less than 98% 1a Dissolve in 500ml of DMSO, stir to dissolve, add 300ml of 10% sodium carbonate solution, cool down to 0°C, then add 65.2g / 200ml of Fmoc-Cl / DMSO solution dropwise, dropwise in 20-40 minutes, drop After the addition, react at 0-3°C for 2 hours, and then react at room temperature for 2 hours; inject the reaction solution into HPD-950 macroporous adsorption resin for adsorption, first rinse with water, and then analyze with 30% ethanol solution to obtain the analysis solution of the desired product, thin film Evaporator concentrated to a small volume and then evaporated to dryness under reduced pressure to obtain a yellow oil; EI (m / z): 1338 (M+1);

[0027] Dissolve the above yellow oil in 150ml of water and 100ml of DMSO mixture, cool down to 0-5°C, adjust the pH value to 2.5-3.0 with hydrochloric acid, add 12.3ml of 40% acetaldehyde aqueous solution after dissolving, and control the temperature at 0-5°C. React at ...

Embodiment 2

[0031] 25g of gentamicin C with a purity of not less than 98% 1a Dissolve in 500ml of DMSO, stir to dissolve, add 350ml of 10% sodium carbonate solution, lower the temperature to 0°C, and then add 68.1g / 200ml of Fmoc-Cl / DMSO solution dropwise to it, the dropwise addition is completed in 20-40 minutes, dropwise After completion, react at 0-3°C for 2 hours, and then react at room temperature for 2 hours; inject the reaction solution into HPD-950 macroporous adsorption resin for adsorption, rinse with water first, and then analyze with 30% ethanol solution to obtain the analysis solution of the desired product, and evaporate the film Evaporate to dryness under reduced pressure to obtain a yellow oil after being concentrated to a small volume; EI (m / z): 1338 (M+1);

[0032] Dissolve the above yellow oil in 160ml of water and 100ml of DMSO mixture, cool down to 0-5°C, adjust the pH value to 2.5-3.0 with hydrochloric acid, add 12.3ml of 40% acetaldehyde / water solution after dissolvi...

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Abstract

The invention discloses an etimicin sulfate preparation method. The etimicin sulfate preparation method includes the steps of protecting amino groups at 3, 2', 6' and 3' of gentamicin C1a with Fmoc-Cl and performing purification and evaporation to dryness to obtain quadrifluorenyl methoxycarbonyl gentamicin C1a; adding N-ethyl of an acetaldehyde aqueous solution under acidic conditions and performing reduction with sodium triacetoxyborohydride; finally adding a piperidine / DMSO (dimethylsulfoxide) solution for deprotection; performing secondary purification on an reaction solution with weakly acidic cation adsorption resin after performing primary purification on the reaction solution with a macroporous adsorption resin column and adding sulfuric acid to a purified product to obtain etimicin sulfate through reaction. The etimicin sulfate preparation method is high in selectivity and less in side reaction in group protecting, mild in reaction conditions, simple in operation and easy to perform industrial production during the whole reaction process and high in purity and yield of the product. (An equation as shown in the description).

Description

technical field [0001] The invention relates to a preparation method of etimicin sulfate, which belongs to the technical field of medicine. Background technique [0002] Etimicin sulfate is a new generation of semi-synthetic aminoglycoside antibiotics with high efficiency, low toxicity and resistance to drug-resistant bacteria independently developed by my country. It is the only anti-infective drug that has obtained the national first-class new drug certificate. [0003] Chinese patent CN1040177C (application number: 93112412.3) discloses a 1-N-ethyl gentamicin C 1a The preparation method and pharmaceutical preparation of its salt, and described 1-N-ethyl gentamicin C 1a The preparation method: the first step, the purified gentamicin C 1a Dissolve in water or aprotic organic solvents (such as N,N-dimethylformamide, dimethyl sulfoxide, etc.) at room temperature, then add cobalt acetate, dropwise add the tetrahydrofuran solution of acetic anhydride, and keep warm until the ...

Claims

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Application Information

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IPC IPC(8): C07H15/236C07H1/00C07H1/06
Inventor 赵雪宁杨庆坤张雷雷李保勇吴柯张兆珍董廷华孙星星周学文
Owner QILU PHARMA HAINAN
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