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Preparation method of 1-N-ethyl gentamicin C1a

A technology of ethyl gentamycin and ethyl gentamycin, applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of low yield, difficult separation and purification, cumbersome process, etc. , to achieve the effect of increasing the yield

Active Publication Date: 2014-03-26
WUXI JIMIN KEXIN SHANHE PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, there are problems such as low yield, difficult separation and purification in the later stage, and complicated process

Method used

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  • Preparation method of 1-N-ethyl gentamicin C1a
  • Preparation method of 1-N-ethyl gentamicin C1a
  • Preparation method of 1-N-ethyl gentamicin C1a

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] At a temperature of 18-20°C, slowly add 288g of sodium borohydride into a three-necked flask filled with 4L of chloroform and 2L of glacial acetic acid. 575g of 3,2',6'-tri-N-acetyl gentamicin C 1a Dissolve it in 6L of chloroform, slowly add it into the above-mentioned three-necked flask through a constant pressure dropping funnel, keep the temperature at 40°C, and vigorously stir for 20 hours. The temperature was lowered to 25°C, and saturated aqueous sodium hydroxide solution was added to neutralize the system. Add 5L of ethanol to dilute, extract three times with 3L of chloroform, and concentrate in vacuo. The obtained oil was added to 4 L of 1N aqueous sodium hydroxide solution and refluxed for 24 hours. Dilute it with 6L of non-salt water, pass it into a chromatographic separation column to load the sample, wash with non-salt water, analyze with ethanol aqueous solution, and collect the effective components. Concentrate and freeze-dry to obtain 396g of the produ...

Embodiment 2

[0022] At a temperature of 18-20°C, slowly add 330 g of sodium borohydride into a three-necked flask filled with 4 L of chloroform and 2 L of glacial acetic acid. 575g of 3,2',6'-tri-N-acetyl gentamicin C 1a Dissolve it in 6L of chloroform, slowly add it into the above-mentioned three-necked flask through a constant pressure dropping funnel, keep the temperature at 50°C, and vigorously stir for 20 hours. The temperature was lowered to 25°C, and saturated aqueous sodium hydroxide solution was added to neutralize the system. Add 5L of ethanol to dilute, extract three times with 3L of chloroform, and concentrate in vacuo. The obtained oil was added to 4 L of 1N aqueous sodium hydroxide solution and refluxed for 24 hours. Dilute it with 6L of non-salt water, pass it into a chromatographic separation column to load the sample, wash with non-salt water, analyze with ethanol aqueous solution, and collect the effective components. Concentrate and freeze-dry to obtain 405g of the pr...

Embodiment 3

[0024] At a temperature of 18-20°C, slowly add 300 g of sodium borohydride into a three-necked flask filled with 4 L of chloroform and 2 L of glacial acetic acid. 575g of 3,2',6'-tri-N-acetyl gentamicin C 1a Dissolve it in 6L of chloroform, slowly add it into the above-mentioned three-neck flask through a constant pressure dropping funnel, keep the temperature at 45°C, and vigorously stir for 20 hours. The temperature was lowered to 25°C, and saturated aqueous sodium hydroxide solution was added to neutralize the system. Add 5L of ethanol to dilute, extract three times with 3L of chloroform, and concentrate in vacuo. The obtained oil was added to 4 L of 1N aqueous sodium hydroxide solution and refluxed for 24 hours. Dilute it with 6L of non-salt water, pass it into a chromatographic separation column to load the sample, wash with non-salt water, analyze with ethanol aqueous solution, and collect the effective components. Concentrate and freeze-dry to obtain 419g of the prod...

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Abstract

The invention relates to a preparation method of 1-N-ethyl gentamicin C1a. The method comprises the following steps: under the condition of 18-20 DEG C, slowly adding sodium borohydride into three flasks with trichloromethane and glacial acetic acid, dissolving 3,2',6'-tri-N-gentamicin C1a into trichloromethane, slowly adding the mixture into the flasks through a constant pressure dropping funnel, keeping the temperature to 40-50 DEG C, vigorously stirring for reaction 20 hours, cooling and adding a saturated sodium hydroxide aqueous solution to neutralize the system, diluting with ethyl alcohol, extracting with trichloromethane, performing vacuum concentration to obtain the oily matter, and adding a 1N sodium hydroxide aqueous solution for circulation reflux for 24 hours; diluting with salt-free water, performing column chromatography isolation, collecting effective constituents, concentrating and freeze-drying to obtain 1-N-ethyl gentamicin C1a.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to an aminoglycoside antibiotic drug gentamicin C 1a Derivatives (1-N-ethyl gentamicin C 1a ) preparation method. Background technique [0002] Etimicin sulfate (Etimicin sulfate) is a new generation of semi-prepared aminoglycoside antibiotics with high efficiency, low toxicity and resistance to drug-resistant bacteria with independent intellectual property rights. It is the only one that has obtained the national first-class new drug certificate. Anti-infective drugs. Its mechanism of action is to resist the normal protein production of sensitive bacteria, and it is effective against Escherichia coli, Klebsiella pneumoniae, Enterobacter spp. etc. have high antibacterial activity, have certain antibacterial activity to some Pseudomonas, Acinetobacter, etc. The MIC values ​​of Helicobacter and Klebsiella pneumoniae are still within the plasma concentration range of the therapeu...

Claims

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Application Information

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IPC IPC(8): C07H15/236C07H1/00
Inventor 姜迎庆
Owner WUXI JIMIN KEXIN SHANHE PHARMA
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