Cefixime impurity and preparation method thereof

A technology for cefixime and impurities, applied in the field of cefixime impurities and its preparation, to achieve the effects of reasonable route design, convenient purification, and easy availability of raw materials

Active Publication Date: 2021-07-20
TLC NANJING PHARMA RANDD CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Up to now, no report about the impurity compound of this application and its synthesis method has been retrieved in the database. This compound is lik

Method used

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  • Cefixime impurity and preparation method thereof
  • Cefixime impurity and preparation method thereof
  • Cefixime impurity and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Preparation of Compound A: Suspend 30g of cefixime in 300mL of tert-butyl propionate, add 16.4mL of boron trifluoride diethyl ether in an ice bath, and react at 40°C for 8 hours. After the reaction is complete, the reaction solution is added to water, extracted three times with ethyl acetate, Dried over anhydrous sodium sulfate, filtered, and spin-dried, the crude product was purified by column to obtain 27.8 g of white solid A with a yield of 74.3%.

[0033]

[0034] Preparation of Compound B: Dissolve 15.2g of Compound A in 304mL of acetonitrile, then add 18.3g of 25% hydrogen peroxide and 0.1g of sodium tungstate, react at 10°C for 12 hours, monitor the end of the reaction by TLC, dilute with 600mL of ethyl acetate, wash three times with water, Dried over anhydrous sodium sulfate, filtered, spin-dried, and purified by column to obtain 10.2 g of white solid B with a yield of 63.5%.

[0035]

[0036] Preparation of compound Cefixime Sulfone: Dissolve 10g of compo...

Embodiment 2

[0039] The preparation of compound A: 30g cefixime was suspended in 600mL tert-butyl propionate, 19.8mL concentrated sulfuric acid was slowly added dropwise in an ice bath, and reacted for 6 hours at 25 degrees Celsius. After the reaction was completed, the reaction solution was added to water, extracted three times with ethyl acetate, and no Dried over sodium sulfate, filtered, and spin-dried, the crude product was purified by column to obtain 29.5 g of white solid A with a yield of 78.8%.

[0040]

[0041] The preparation of compound B: get 15.5g compound A and dissolve in 310mL acetonitrile, then add 16.7g peroxyacetic acid, react 8 hours at 30 degrees centigrade, TLC monitoring reaction finishes, add 100mL saturated sodium thiosulfate aqueous solution, quench excessive oxidant, The organic phase was washed three times with water, dried over anhydrous sodium sulfate, filtered, spin-dried, and purified by column to obtain 8.3 g of white solid B with a yield of 50.7%.

[0...

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Abstract

The invention discloses a cefixime impurity and a preparation method thereof, and belongs to the field of medicine synthesis. According to the method, cefixime serves as a starting raw material, CefiximeSulfone is obtained through acid catalysis esterification, oxidation and hydrolysis, the route design is reasonable, the raw materials are easy to obtain, operability is high, purification is convenient, aftertreatment is simple, the purity of the prepared target product can reach 99.5% or above, a reference sample is provided for cefixime research, a reference substance for analysis and research can be provided for clinical, pharmacological and pharmacokinetics of cefixime, and the method has important research value in clinical pharmacokinetics research.

Description

technical field [0001] The invention belongs to the medicine synthesis technology, and in particular relates to a cefixime impurity and a preparation method thereof. Background technique [0002] Cefixime (Cefixime), the chemical name is (6R,7R)-7-((Z)-2-(2-aminothiazol-4-yl)-2-((carboxymethoxy)imino)acetamido)-8-oxo- 3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, which was successfully developed by Fujisawa Pharmaceutical Co., Ltd. in Japan in 1987, and was first listed in Japan for use in Clinically, it was launched in the United States in 1989 and has been widely used clinically in more than 80 countries in 1999. [0003] Cefixime is an important part of anti-infective drugs, and cefixime is the first orally effective third-generation cephalosporin, although cefixime is less permeable to the outer membrane of Gram-negative bacteria than cephalexin and Cefaclor, but due to the extreme stability of cefixime to β-lactamases including penicillinase and cepha...

Claims

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Application Information

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IPC IPC(8): C07D501/22C07D501/04
CPCC07D501/22C07D501/04
Inventor 耿庆振李建忠马森张池崔希林
Owner TLC NANJING PHARMA RANDD CO LTD
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