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Method for preparing etimicin sulfate

A technology of etimicin sulfate and copper acetate, applied in the field of medicine, can solve the problems of cumbersome process, difficult purification, many by-products and the like, and achieves the effects of high yield, high selectivity and few side reactions

Active Publication Date: 2013-05-22
QILU PHARMA HAINAN +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The disclosed process generally has problems such as low yield, cumbersome process, step-by-step reduction and deprotection steps, high temperature, long cycle, many by-products, and difficult purification during deprotection.

Method used

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  • Method for preparing etimicin sulfate

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Experimental program
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Effect test

Embodiment 1

[0021] 15g of gentamicin C with a purity ≥ 98% 1a Dissolve in 150mL DMF, add 16.3g copper acetate monohydrate at room temperature, and react for 20 minutes; then add 17.5g benzyl chloride to the reaction system, raise the temperature to 25°C, and then add 10.2g sodium bicarbonate to the reaction system in batches , 1.5-2 hours to complete the addition, after the addition, the temperature was controlled at 25°C for 4 hours. Pass hydrogen sulfide gas into the obtained reaction solution for decopper treatment, filter to remove insoluble matter, inject the filtrate into a 732 strong acidic cationic resin column for purification, first wash with water until the optical rotation is not greater than 0.050, and then use a concentration of 0.2-2mol / L of ammonia water was analyzed to obtain the analytical solution of the desired product, which was concentrated under reduced pressure to obtain a light yellow oil, which was Compound Ⅰ, EI (m / z): 720 (M+1);

[0022] Disperse compound I i...

Embodiment 2

[0024] 15g of gentamicin C with a purity of not less than 98% 1a Dissolve in 120mL DMSO, add 16.3g copper acetate monohydrate at room temperature, react for 20 minutes, add 23.6g benzyl bromide to the reaction system, raise the temperature to 25°C, then add 12.2g triethylamine in batches to the reaction system, 1.5-2 hours to complete the addition, after the completion of the addition, control the temperature at 25 ° C for 1 hour, pass hydrogen sulfide gas into the obtained reaction liquid for decopper treatment, filter to remove insoluble matter, inject the filtrate into a 732 strong acid cationic resin column for purification, first Rinse with water until the optical rotation is not greater than 0.050, then analyze with ammonia water with a concentration of 0.2-2mol / L to obtain the analytical solution of the desired product, concentrate under reduced pressure to obtain a light yellow oil, which is compound Ⅰ, EI (m / z ): 720 (M+1);

[0025] Disperse compound I in a mixed sol...

Embodiment 3

[0027] 15g of gentamicin C with a purity of not less than 98% 1a Dissolve in 120mL DMSO, add 16.3g copper acetate monohydrate at room temperature, react for 20 minutes, add 17.5g benzyl chloride to the reaction system, raise the temperature to 25°C, then add 10.2g sodium bicarbonate in batches to the reaction system, 1.5-2 hours to complete the addition, after the completion of the addition, control the temperature at 25 ° C for 2 hours, pass hydrogen sulfide gas into the obtained reaction liquid for decopper treatment, filter to remove insoluble matter, inject the filtrate into a 732 strong acid cationic resin column for purification, first Rinse with water until the optical rotation is not greater than 0.050, then analyze with ammonia water with a concentration of 0.2-2mol / L to obtain the analytical solution of the desired product, and concentrate under reduced pressure to obtain a light yellow oil, which is Compound Ⅰ, EI (m / z): 720 (M+1);

[0028] Disperse compound I in ...

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Abstract

The invention discloses a method for preparing etimicin sulfate, and belongs to the technical field of medicines. The method comprises the steps of: adding copper acetate monohydrate into gentamicin C1a to form a copper ion complex; then adding a benzyl compound into a reaction system, controlling the temperature at 15-40 DEG C, and then adding alkali into the reaction system to react; decoppering and purifying the obtained reaction liquid so as to obtain a light yellow oily compound I; adding acetic acid into the oily substance, controlling the temperature at 5-15 DEG C, adding acetaldehyde to react for a while, adding a catalyst Pd / C and continuously filling hydrogen to react; and separating, purifying and acidizing the reaction liquid so as to obtain etimicin sulfate. The method of utilizing benzyl to protect amino groups is adopted, and high selectivity is obtained; and two reaction steps of reduction and deprotection are completed through a 'one-pot method', and the method is low in reaction temperature and takes a short period, thus, side reaction is less, purification is easy, the reaction and separation costs are lowered, and the method can be easily applied to industrial production.

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, a semi-synthetic aminoglycoside antibiotic, has the characteristics of high efficiency, safety, broad-spectrum antibacterial, and no cross-resistance. It was developed by the "Jiangsu Provincial Institute of Microbiology" and has obtained patents in China, the United States, the United Kingdom, Japan, Russia, Kazakhstan and other countries, and has been widely used because of its advantages as a new type of antibacterial drug with high efficiency and low toxicity. Its mechanism of action is to resist the normal protein synthesis of sensitive bacteria, including Escherichia coli, Klebsiella pneumoniae, Enterobacter, Serratia, Proteus mirabilis, Salmonella, Haemophilus influenzae and Staphylococcus aureus genera have high antibacterial activity, have certain antibacterial activity against so...

Claims

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Application Information

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IPC IPC(8): C07H15/236C07H1/00
Inventor 张雷雷杨庆坤周先国李哲杨波勇吴柯张兆珍董廷华李保勇朱绍万
Owner QILU PHARMA HAINAN
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