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A kind of 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, simple post-treatment, and convenient purification

Active Publication Date: 2022-08-05
TLC NANJING PHARMA RANDD CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 likely to be a metabolic impurity, so this compound is synthesized by this application to provide a reference for the study of the metabolism of cefixime

Method used

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  • A kind of cefixime impurity and preparation method thereof
  • A kind of cefixime impurity and preparation method thereof
  • A kind of cefixime impurity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of compound A: Suspend 30 g of cefixime in 300 mL of tert-butyl propionate, add 16.4 mL of boron trifluoride ether in an ice bath, and react at 40 degrees for 8 hours. Dry over anhydrous sodium sulfate, filter, spin dry, and purify the crude product through column to obtain 27.8 g of white solid A with a yield of 74.3%.

[0033]

[0034] Preparation of compound B: Dissolve 15.2 g of compound A in 304 mL of acetonitrile, then add 18.3 g of 25% hydrogen peroxide and 0.1 g of sodium tungstate, react at 10 degrees Celsius for 12 hours, monitor the reaction by TLC, dilute with 600 mL of ethyl acetate, wash with water three times, Dry over anhydrous sodium sulfate, filter, spin dry, and purify 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 10 g of compound B in 30 mL of formic acid, react at 30 degrees Celsius for 10 hours, monitor the reaction by TLC, spin dry the react...

Embodiment 2

[0039] The preparation of compound A: 30g of cefixime was suspended in 600mL of tert-butyl propionate, 19.8mL of concentrated sulfuric acid was slowly added dropwise in an ice bath, and the reaction was performed at 25 degrees Celsius for 6 hours. Dry over sodium sulfate, filter, spin dry, and purify the crude product 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 peracetic acid, 30 degrees Celsius of reaction 8 hours, TLC monitoring reaction finishes, add 100mL saturated sodium thiosulfate aqueous solution, quench excess 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%.

[0042]

[0043] The preparation of compound Cefixime Sulfone: get 8.0g compound B and be suspended in 80mL 2M hydr...

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Abstract

The invention discloses a cefixime impurity and a preparation method thereof, belonging to the field of pharmaceutical synthesis. The method of the present application uses cefixime as the starting material, and obtains CefiximeSulfone through acid-catalyzed esterification, oxidation, and then hydrolysis. The route design is reasonable, the raw materials are readily available, the operability is strong, the purification is convenient, the post-processing is simple, and the prepared target The purity of the product can reach more than 99.5%, which can provide a reference sample for the research of cefixime, and can provide the reference material for the analysis and research of the clinical, pharmacology and pharmacokinetics of cefixime, and has important research value in clinical pharmacokinetic research. .

Description

technical field [0001] The invention belongs to the pharmaceutical synthesis technology, in particular to a cefixime impurity and a preparation method thereof. Background technique [0002] Cefixime, 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 Japan Fujisawa Pharmaceutical Co., Ltd. in 1987, and was first listed in Japan for application Clinically, it was listed in the United States in 1989, and has been widely used clinically in more than 80 countries in 1999. [0003] Cefixime is an important component 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 cefixime. Cefaclor, but because cefixime is extremely stable to beta-lactamases including penicillinase and cephalospor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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