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Technology for enzymatic synthesis of tulathromycin

A teramycin and enzymatic synthesis technology, applied in fermentation and other directions, can solve the problems of cumbersome production process, serious pollution, dangerous operation, etc., and achieve the effects of high product purity, less pollution and less side reactions

Inactive Publication Date: 2017-02-22
AMICOGEN CHINA BIOPHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] In the existing process of chemical synthesis of telamycin, the removal of the protective group on the 4-hydroxyl group requires the use of expensive and dangerous palladium carbon for hydrogenation removal under high pressure, the production process is cumbersome, the operation is dangerous, and the pollution is serious , the problem of high cost, the present invention provides a kind of new technology of enzymatic synthesis telamycin, reaction route is as follows:

Method used

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  • Technology for enzymatic synthesis of tulathromycin
  • Technology for enzymatic synthesis of tulathromycin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Add 140ml of dichloromethane, 17g (23.1mmol) of demethylated azithromycin, 4.6g (27.6mmol) of benzyl chloroformate into the reaction flask, control the temperature at 0-5°C for 1h, cool down to -80°C, add dimethyl 32g (409.5mol) of sulfoxide, 16.2g (77.0mmol) of trifluoroacetic anhydride was added dropwise, the reaction was completed for 30min, and 17.2g (170.0mmol) of triethylamine was added dropwise for 30min, after the reaction was completed, 100ml of water was added to the system for extraction. The organic phase was concentrated under reduced pressure to obtain 23.8 g of compound one.

[0040] Add 130ml THF, 20.8g (132mmol) trimethylsulfide bromide, 19.6g (175mmol) potassium tert-butoxide to the reaction flask, carry out sulfur ylide reaction at -10~15°C, react for 1.5h and cool down to -80°C, put Compound 2 was dissolved in 50ml of dichloromethane, added to sulfur ylide solution, and reacted at -75 to -85 for 2.5 hours. After the reaction was completed, the reacti...

Embodiment 2

[0043]140ml of dichloromethane, 17g (23.1mmol) of demethyl azithromycin, 4.6g (27.6mmol) of benzyl chloroformate were added to the reaction flask, the temperature was controlled at 0-5°C and reacted for 1h, cooled to -80°C, and dimethyl 32g (409.5mol) of sulfoxide, 16.2g (77.0mmol) of trifluoroacetic anhydride were added dropwise, the reaction was completed dropwise for 30min, 17.2g (170.0mmol) of triethylamine was added dropwise for 30min, and 100ml of water was added to the system for extraction after the reaction was completed. The organic phase was concentrated under reduced pressure to obtain compound-23.5 g.

[0044] Add 130ml of THF, 20.8g (132mmol) of trimethyl sulfide bromide, 19.6g (175mmol) of potassium tert-butoxide into the reaction flask, carry out sulfur ylide reaction at -10~15°C, and cool down to -80°C for 1.5h. The compound was dissolved in 50ml of dichloromethane and added to the sulfur ylide solution, -75~-85 was reacted for 2.5h, after the reaction was com...

Embodiment 3

[0047] 140ml of dichloromethane, 17g (23.1mmol) of demethyl azithromycin, 4.6g (27.6mmol) of benzyl chloroformate were added to the reaction flask, the temperature was controlled at 0-5°C and reacted for 1h, cooled to -80°C, and dimethyl 32g (409.5mol) of sulfoxide, 16.2g (77.0mmol) of trifluoroacetic anhydride were added dropwise, the reaction was completed dropwise for 30min, 17.2g (170.0mmol) of triethylamine was added dropwise for 30min, and 100ml of water was added to the system for extraction after the reaction was completed. After the organic phase was concentrated under reduced pressure, compound one 23.6 was obtained.

[0048] Add 130ml of THF, 20.8g (132mmol) of trimethyl sulfide bromide, 19.6g (175mmol) of potassium tert-butoxide into the reaction flask, carry out sulfur ylide reaction at -10~15°C, and cool down to -80°C for 1.5h. Compound 1 was dissolved in 50ml of dichloromethane and added to the sulfur ylide solution, -75~-85 was reacted for 2.5h, after the react...

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Abstract

The invention relates to a method for synthesizing a veterinary medicine, and in particular, relates to a method for enzymatic synthesis of tulathromycin. A compound II and a immobilized esterase are added to water, after each-time reaction, a mother liquor and the immobilized lipase only require to be filtered and separated, and the immobilized esterase only requires to be washed with deionized water and can be reused; the synthesis process has the advantages of simple technology, convenience in operation, short reaction time, high production efficiency, low cost and less pollution.

Description

[0001] Technical field: [0002] The invention designs a method for synthesizing veterinary drugs, specifically a method for enzymatically synthesizing telamycin. [0003] Background technique: [0004] Respiratory tract infections of livestock in animal husbandry are generally multiple infections, with many pathogenic factors and complicated conditions. While seeking biological control and environmental blocking, drug treatment and prevention are the main ways at present. Therefore, it is imminent to find a new type of antibacterial drug that is safe, effective and low-residue for this infection. [0005] Pfizer Pharmaceuticals launched Tyramycin in 2002. Various countries have conducted a large number of in vivo and in vitro pharmacology and toxicology related experiments. At the same time, a large number of clinical trials have proved that Tyramycin has strong antibacterial activity and broad antibacterial spectrum. , long half-life and many other advantages, it has become ...

Claims

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Application Information

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IPC IPC(8): C12P19/62
CPCC12P19/62
Inventor 王晶金永东李秀秀李建国王玲
Owner AMICOGEN CHINA BIOPHARM CO LTD
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