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Preparation method of hydrochloric acid ceftiofur

A technology of ceftiofur hydrochloride and cefuroxime, which is applied in the field of chemical synthesis of veterinary chemical raw materials, can solve the problems of inconvenient large-scale production, cumbersome operation, and long cycle, and achieves the advantages of small toxic and side effects, simple operation, and few impurities. Effect

Active Publication Date: 2010-02-24
PU LIKE BIO ENG
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] The reported synthetic route of ceftiofur hydrochloride: directly synthesize ceftiofur hydrochloride with dry product of ceftiofur free acid. The advantage of this method is that the target product is of high purity. It is cumbersome, the cycle is long, and a large amount of solvent is used, which is not convenient for large-scale production

Method used

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  • Preparation method of hydrochloric acid ceftiofur
  • Preparation method of hydrochloric acid ceftiofur

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 (6R, 7R)-7-[2-(2-aminothiazol-4-yl)-(Z)-2-(methoxyimino)acetamido]-3-[(2-furancarbonyl ) Synthesis of thiomethyl]-3-cephem-4-carboxylic acid (II).

[0039] In a 500ml three-necked reaction flask, add 198ml of acetone, cool down in an ice bath, stir for 30 minutes, add 5.28g of cefuroxime, 10.2g of AE-active ester and 1.2g of antioxidant BHT in batches, stir for 25 minutes, and then add triethyl ether dropwise 10.6ml of amine was added dropwise in 30 minutes, kept in an ice bath for 6 hours, and the reaction was complete. Raise the temperature to 20-35°C, add 198ml of acetone to dilute, add 19.0ml of water, then add 5.0g of activated carbon, stir for 45 minutes to decolorize, and remove the activated carbon by suction filtration to obtain (6R,7R)-7-[2-( 2-aminothiazol-4-yl)-(Z)-2-(methoxyimino)acetamido]-3-[(2-furancarbonyl)thiomethyl]-3-cephem-4-carboxylic acid (II), namely ceftiofur free acid solution.

Embodiment 2

[0040] The synthesis of embodiment 2 ceftiofur hydrochloride:

[0041] Add the ceftiofur free acid solution prepared in Example 1 into a 1000ml three-necked reaction flask, stir, add 5ml of concentrated hydrochloric acid (37.7%) drop by drop, a large amount of crystals are precipitated after the addition, stir for 1 hour, and place at room temperature overnight to grow crystals . Suction filtration to obtain a wet product of ceftiofur hydrochloride, and drying under reduced pressure at 30-35°C for 24 hours to obtain 7.2 g of ceftiofur hydrochloride white to off-white crystalline powder with a purity of 99.7%.

Embodiment 3

[0042] The synthesis of embodiment 3 ceftiofur hydrochloride:

[0043] In a 1000ml three-necked reaction flask, add 17.28g of cefurofuric acid and 432ml of tetrahydrofuran, stir for 30 minutes, add 21.32g of AE-active ester in batches, add 2.33g of antioxidant BHT, and cool in an ice bath for 1 hour. 25.3 ml of triethylamine was added, and the addition was completed in 30 minutes. Keep the reaction in an ice bath for 6 hours. After the reaction is complete, add 21ml of water, slowly warm up to room temperature, then add an appropriate amount of concentrated hydrochloric acid to adjust the pH value to 1.0, stir for 1 hour, crystals gradually precipitate, and place at room temperature overnight to grow crystals. Suction filtration to obtain ceftiofur hydrochloride wet product, dried under reduced pressure at 30-35°C for 24 hours, ceftiofur hydrochloride white to off-white crystalline powder 25.3g, purity 99.1%.

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Abstract

The invention discloses a preparation method of hydrochloric acid ceftiofur, which relates to the field of the chemical synthesis of bulk pharmaceutical chemicals for livestock and comprises the following steps: adding reaction organic solvents in a reaction bottle; taking AE-active ester; adding ceftiofur and an antioxidant in the reaction bottle; uniformly stirring to obtain a reaction solution;dripping an organic amine solution in the obtained reaction solution; keeping the temperature and reacting; adding the organic solvents for diluting; decoloring active carbon; filtering out the active carbon to obtain a reaction solution; adding the solvents in the reaction solution for diluting; adding water and concentrated hydrochloric acid; regulating pH value to be 1 to 2; stirring for 1 hour; gradually separating out crystals; putting and maintaining the crystals over a night at room temperature; filtering; rinsing; drying and eliminating the solvents to obtain the crystals of the hydrochloric acid ceftiofur. The ceftiofur is used as raw material; the condensation reaction process for preparing free acid of the ceftiofur and the reaction for generating hydrochloride of the free acidof the ceftiofur are combined; the preparation method is simple and an obtained target product has high purity and high-purity hydrochloric acid ceftiofur and can be industrially produced in large batch.

Description

【Technical field】 [0001] The invention belongs to the field of chemical synthesis of veterinary chemical raw materials, and in particular relates to a method for preparing ceftiofur hydrochloride. 【Background technique】 [0002] Ceftiofur hydrochloride, a third-generation cephalosporin antibiotic specially used for livestock and poultry, has a broad antibacterial spectrum, strong antibacterial activity, and rapid action. It has antibacterial effect and can be widely used clinically to treat respiratory and digestive infections of livestock and poultry. So far, ceftiofur sodium and hydrochloride have been used to treat bacterial diseases of cattle, sheep, pigs, poultry, dogs, cats and other animals. Highly sensitive, sensitive bacteria mainly Pasteurella multocida, Pasteurella hemolyticus, Actinobacillus pleuropneumoniae, Haemophilus, Salmonella, Escherichia coli, Staphylococcus, Streptococcus, Bacillus perfringens, etc. [0003] Table 1 Antibacterial test effect of ceftiof...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/36C07D501/06
Inventor 刘兴金李兴国谷志勇
Owner PU LIKE BIO ENG
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