Ceftiofur acetoxy ethyl ester and preparation method thereof

A technology for ceftiofur acetoxyethyl ester and cephalosporin, which is applied in the field of ceftiofur acetoxyethyl ester and its preparation, can solve the problem of low bioavailability, instability, poor absorption of ceftiofur and its sodium salt and other problems, to achieve the effect of high bioavailability, reduced side effects, and reduced usage

Active Publication Date: 2013-12-04
LUOYANG HUIZHONG ANIMAL MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Ceftiofur and its sodium salt have significant antibacterial effects, but they are extremely unstable in water and are hydrolyzed into desfuroyl ceftiofur, which loses their pharmacological activity in the gastrointestinal tract after contact with water or oral administration during the preparation process. And its sodium salt is poorly absorbed in the gastrointestinal tract and has low oral bioavailability, which limits the application of ceftiofur in oral administration

Method used

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  • Ceftiofur acetoxy ethyl ester and preparation method thereof
  • Ceftiofur acetoxy ethyl ester and preparation method thereof
  • Ceftiofur acetoxy ethyl ester and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Weigh 10.0g (0.018mol) of ceftiofur sodium (Zhejiang Haizheng batch number 20080501), add it into a 250mL three-necked bottle, add 100mL of N,N-dimethylacetamide, stir to dissolve, cool down to 0°C, 5.1 g (0.058 mol) of 1-bromoethyl acetate (Quanxi Chemical Factory, Huixian City) was put in, and the reactants were stirred and reacted at 1° C. for 90 minutes. Add 0.25g (0.0018mol) of potassium carbonate, and stir at 1-3°C for 2h. Add the reactant to a mixture composed of 200mL ethyl acetate and 50mL 3% W / V sodium bicarbonate, stir for 1h, let stand to separate layers, take the organic phase, and wash with 50mL 1mol / L hydrochloric acid and 15mL 20% sodium chloride solution respectively (containing 2% w / v sodium bicarbonate) wash. The three aqueous phases were all washed with 50 mL of ethyl acetate, the organic phases were combined, and 1 g of activated carbon was added and stirred for 30 min. The filtrate was rotary evaporated at 40°C to 30mL, and 100mL of isopropyl eth...

Embodiment 2

[0046] Weigh 10.0g (0.018mol) ceftiofur (Luoyang Huizhong Veterinary Medicine Co., Ltd., batch number 20090101), add it to a 250mL three-necked bottle, add 100mL tetrahydrofuran and stir to dissolve, it is in a solution state, cool down to 0°C, and weigh 5.1g (0.058mol) 1-bromoethyl acetate, and the reactant was stirred at 1°C for 90min. Add 0.25g (0.0018mol) of potassium carbonate, and stir at 1-3°C for 2h. Quickly add the reactant to the mixed solution consisting of 200mL ethyl acetate and 50mL 3% sodium bicarbonate, stir for 1h, let stand to separate layers, take the organic phase, and use 50mL1mol / L hydrochloric acid and 15mL20%W / V sodium chloride solution respectively (containing 2% w / v sodium bicarbonate) wash. The three aqueous phases were all washed with 50 mL of ethyl acetate, the organic phases were combined, and 1 g of activated carbon was added and stirred for 30 min. The filtrate was rotary evaporated at 40°C to 30mL, added 50mL of isopropanol, evaporated at 40°...

Embodiment 3

[0051] Ceftiofur sodium and ceftiofur acetoxyethyl ester were respectively added with appropriate amount of Baifumei powder (Henan Zhongyuan Biotechnology Co., Ltd.) to make a 10% premix (the content was calculated as the active ingredient), and the SPF experimental animal room was administered orally. Drug two groups of Du Dalong pigs, 20mg / kg (calculated as ceftiofur), 10 pigs in each group, 5mL of blood was collected at 15, 30min, 1, 2, 4, 8, 12, 24, 36, 48, 60, 72h , Determination of blood concentration. The blood sample was added with dithioerythritol, derivatized with iodoacetamide, extracted and purified by solid-phase extraction, dried with nitrogen, added an appropriate amount of mobile phase, and separated on a C18 chromatographic column, using acetonitrile-trifluoroacetic acid-water (volume ratio acetonitrile: three Fluoroacetic acid: water is 300: 1: 700) as mobile phase, 266nm ultraviolet detects, fits and calculates pharmacokinetic parameter with pharmacokinetic ...

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Abstract

The invention provides a compound—ceftiofur acetoxyethyl ester and a preparation method thereof, that is, adding an esterification agent, such as 1-bromoethyl acetate, to an organic solvent from ceftiofur or its sodium salt Steps for obtaining ceftiofur acetoxyethyl ester. The compound, ceftiofur acetoxyethyl ester, has better absorption in the gastrointestinal tract of animals than ceftiofur or its sodium salt, and has the characteristics of high bioavailability, and can be used for the treatment or prevention of pigs, poultry, cattle, The application of drug-resistant Staphylococcus aureus and Gram-negative bacteria in the digestive tract, respiratory tract, and genitourinary tract infection of animals such as sheep and dogs. Bacillus, Pasteurella, etc.

Description

technical field [0001] The invention relates to a ceftiofur axetil and a preparation method thereof, in particular to a ceftiofur acetoxyethyl ester and a preparation method thereof. Background technique [0002] Since the 1960s, with the rapid development of intensification and industrialization, animal husbandry has faced the threat of high morbidity and high mortality. Pathogens are affected by the environment or immune pressure, some pathogens have weakened or enhanced virulence, and new mutant strains or serotypes have emerged. In addition, low or inconsistent immunity levels in livestock and poultry groups lead to atypical changes in epidemiological symptoms and pathology of some livestock and poultry diseases, and the original old diseases appear in new forms, causing atypical diseases. At the same time, the development of intensive and industrialized breeding is not high, the procedures are not strict, and the average quality of the industry is low. Antimicrobial dr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/36C07D501/04A61K31/546A61P31/04A61P1/00A61P11/00A61P13/00
Inventor 张许科刘兴金张晓会
Owner LUOYANG HUIZHONG ANIMAL MEDICINE
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