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Vancomycin derivative, preparation method and applications thereof

A technology of vancomycin and its derivatives, applied in the field of vancomycin derivatives and its preparation, can solve the problems of increasing the water solubility and fat solubility of compounds, and large fat solubility

Inactive Publication Date: 2015-03-18
ACESYS PHARMATECH LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The invention provides a vancomycin derivative and a preparation method thereof, which can effectively increase the water solubility of the compound and reduce the fat solubility, thereby solving the problem of high fat solubility

Method used

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  • Vancomycin derivative, preparation method and applications thereof
  • Vancomycin derivative, preparation method and applications thereof
  • Vancomycin derivative, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0241]

[0242] Synthetic steps:

[0243] first step:

[0244]

[0245] Add 2.19g of sodium hydride to a 500ml single-necked bottle, suspend with 100ml of N,N-dimethylformamide, cool to 0-5 degrees under nitrogen protection, dissolve 10.0g of 4-chlorophenylbenzyl alcohol in 100ml of N,N - Dimethylformamide, slowly added dropwise to the reaction solution, after adding and stirring for 0.5 hours, add 7.6 g of methyl bromoacetate dropwise, after adding, raise the temperature to 35-40 degrees and react overnight, after TLC detection, the reaction The solution was poured into 1L of ice water, extracted by adding 500ml of ethyl acetate, the organic phase was washed with saturated sodium chloride, dried over anhydrous sodium sulfate and then spin-dried to obtain the crude product, which was purified by 10% ethyl acetate / petroleum ether column to obtain the oil Liquid 11.0g, yield 83.0%.

[0246] Step two:

[0247]

[0248] Add 2.5g of potassium tert-butoxide into a 100ml ...

Embodiment 2

[0256] Compounds V9, V11, V13, V15, V20, V21, V22, V23, V24, V25, V55, V61 and other compounds can be prepared according to the method in Example 1.

Embodiment 3

[0258]

[0259] Synthetic steps:

[0260] first step:

[0261]

[0262] Add 20ml of n-butanol to a 100ml single-necked bottle, add 1.80g of sodium block in an ice-water bath, heat to reflux until the solid is dissolved, cool to room temperature, add 10.0g of ethyl bromoacetate, after adding, heat up to 40-50 degrees After stirring overnight, after the reaction was detected by TLC, 100 ml of diethyl ether was added, washed with 50 ml of water three times, and the organic phase was spin-dried under reduced pressure to obtain 9.1 g of oily liquid, which could be directly used in the next step.

[0263] Step two:

[0264]

[0265] Add 2.5g of potassium tert-butoxide into a 100ml single-mouth bottle, disperse with 15ml of ether, slowly add 2.2ml of methyl formate solution of 3.0g of the raw material in the previous step under nitrogen protection, react the reaction solution at room temperature overnight, and add ether after the reaction is detected by TLC 50ml, stirred f...

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PUM

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Abstract

The present invention provides a vancomycin derivative, and a preparation method and an application thereof. The vancomycin derivative of the present invention is obtained by introducing a glyceric acid part between a vancomycin derivative and a fat-soluble modification group, and has reduced fat solubility and improved water solubility, thereby reducing a side effect in the cardiovascular aspect.

Description

technical field [0001] The present invention relates to a vancomycin derivative and a preparation method thereof. technical background [0002] Since the clinical use of penicillin in 1940, there have been thousands of antibiotics, and hundreds of them are commonly used clinically. In 2006, the number of anti-infective drugs among the top 500 best-selling drugs in the world has reached 77, which ranks first among the 19 categories of drugs. Due to the large-scale clinical use of antibiotics, bacteria have gradually evolved drug resistance, making more and more antibiotics gradually ineffective. [0003] Vancomycin is a glycopeptide antibiotic produced by a strain of Streptomyces orientalis. It was approved by the US FDA for clinical use in 1958. It is mainly effective against Gram-positive bacteria and has a strong bactericidal ability. It was once known as the last line of defense for humans against bacterial infections. It was not until the 1990s, after nearly 40 years ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K9/00A61K38/14A61P31/04
CPCA61K38/14C07K9/008C07K9/00A61K38/00A61P31/04
Inventor 葛敏
Owner ACESYS PHARMATECH LTD
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