Preparation method of ceftiofur axetil compound or its halogen salt

A compound and thifurate technology are applied in the field of preparation of ceftiofur axetil compounds or their halogen salts, which can solve the problems of cumbersome preparation process, low reaction rate, environmental pollution and the like, and achieve green environmental protection and bioavailability of the preparation process. Low, increase the effect of specific surface area

Active Publication Date: 2020-12-04
济宁市化工研究院 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] But what the preparation method of ceftiofur acetoxyethyl ester used in this patent is traditional esterification process, uses a large amount of DMF (N,N-dimethylformamide) in the preferred preparation process, and DMF is easily soluble in It is extremely difficult to recycle, and it will be decomposed into dimethylamine and carbon monoxide gas during the recycling process, which will pollute the environment. At the same time, it also has the disadvantages of low reaction rate and cumbersome preparation process.

Method used

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  • Preparation method of ceftiofur axetil compound or its halogen salt
  • Preparation method of ceftiofur axetil compound or its halogen salt
  • Preparation method of ceftiofur axetil compound or its halogen salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Weigh 21g (0.04mom) of ceftiofur (self-made 20170816), add it to a 500mL three-necked flask, add 40mL of methanol, add 5.5g (0.04mol) of potassium carbonate and stir to dissolve, add 50g of D201 resin, cool to 10°C, add 40ml of ethyl acetate, then add 12g (0.05mol) iodomethyl pivalate for 90 minutes of ultrasonic reaction at 35°C. Filter, wash the filter cake with 100mL of ethyl acetate, rotary evaporate the filtrate to 30mL at 40°C, add 50ml of isopropanol to dilute, Add 150mL of isopropyl ether dropwise for no less than 30min, grow crystals at room temperature for 1h, filter, and vacuum dry at 40°C for 8h to obtain 18.2g of off-white powder with a purity of 97%.

Embodiment 2

[0053] Weigh 21g (0.04mom) of ceftiofur (self-made 20170816), add it to a 500mL three-necked flask, add 40mL of methanol, then add 5.5g (0.04mol) of potassium carbonate and stir to dissolve it, add 50g of D201 resin, cool down to 10°C, Add 40 ml of ethyl acetate, add 12 g (0.05 mol) of iodoethyl isopropyl carbonate and react ultrasonically at 35 ° C for 90 minutes. Filter, wash the filter cake with ethyl acetate, and rotary evaporate the filtrate to 30 mL at 40 ° C, add 50 ml of isopropanol to dilute , add 150mL isopropyl ether dropwise, the dropping time is not less than 30min, grow crystals at room temperature for 1h, filter, and vacuum dry at 40°C for 8h to obtain 17.3g of off-white powder with a purity of 96.5%.

Embodiment 3

[0055]Weigh 21g (0.04mom) of ceftiofur (self-made 20170816), add it to a 500mL three-necked flask, add 40mL of methanol, then add 5.5g (0.04mol) of potassium carbonate and stir to dissolve it, add 50g of D201 resin, cool down to 10°C, Add 40ml of ethyl acetate, add 15g (0.05mol) of 1-iodoethylcyclohexyl carbonate and react ultrasonically at 35°C for 90 minutes. Filter, wash the filter cake with ethyl acetate, rotary evaporate the filtrate to 30mL at 40°C, add 50ml of isopropanol Dilute, add 150mL isopropyl ether dropwise, dropwise for not less than 30min, grow crystals at room temperature for 1h, filter, and vacuum dry at 40°C for 8h to obtain 20.2g of off-white powder with a purity of 96.3%.

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Abstract

The invention provides a ceftiofur ester type compound or halogen salt thereof as well as a preparation method and application of the ceftiofur ester type compound or the halogen salt thereof. The ceftiofur or sodium salt thereof takes anion exchange resin as a reaction carrier, and an esterification reagent, such as chloro(iodo)methyl pivalate, 1-iodoethyl isopropyl carbonate, 1-iodoethyl cyclohexyl carbonate, methoxyethoxychloromethyl ether, 4-chloromethyl-5-1,3-dioxole-2-one, 1-iodoethyl cyclohexyl carbonate, 2-chlorotriethylamine and hydrochloride thereof, is added into an organic solvent;then ultrasonic reaction is carried out to prepare an ester type compound corresponding to the ceftiofur; furthermore, the halogen salt of the ceftiofur is prepared. In a preparation process, DMF (Dimethyl Formamide) is not used so that the pollution is reduced; the anion exchange resin is used as the reaction carrier so that the reaction speed is improved, a technology is saved and the preparation method is simple.

Description

technical field [0001] The invention relates to the technical field of veterinary medicine, in particular to a preparation method of ceftiofur-like compounds or halogen salts thereof. Background technique [0002] Ceftiofur (Ceftiofur) is a veterinary-specific third-generation cephalosporin successfully developed by Upjohn Company in the 1980s. Its molecular formula is C 19 h 17 N 5 o 7 S 3 , the chemical name is [6R-[6α,7β(z)]]7-[[(α-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[(2-furancarbonyl ) Thio]methyl]-8-oxo-5-thia-1-azabicyclo[4,2,0]oct-2-ene-2carboxylic acid. The drug was first listed in the United States in 1988. Due to its excellent antibacterial activity and pharmacokinetic characteristics, and the stability of β-lactamase produced by Gram-positive bacteria and negative bacteria, it has been successively adopted by some countries in the United States, Canada, Japan and Europe. It has been officially approved by the state to be used for the treatment o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/36C07D501/04C07D501/12A61P31/04A61P11/00A61P1/00A61P13/00
CPCA61P1/00A61P11/00A61P13/00A61P31/04C07D501/04C07D501/12C07D501/36
Inventor 茌亚青李献国杨淑瑛赵德英王志源王姿姿
Owner 济宁市化工研究院
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