Cefuroxime lysine and preparation thereof

A technology of cefuroxime lysine and cefuroxime acid, which is applied in the field of cefuroxime lysine and its preparations, can solve the problems of many impurities and low purity, and achieve the effect of high purity and strong stability

Active Publication Date: 2013-06-05
SHANDONG LUOXIN PARMACEUTICAL GROUP STOCK CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Then the impurity in the cefuroxime lysine crystal in the prior art is many, and purity is not high, for this reason, propose the present invention

Method used

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  • Cefuroxime lysine and preparation thereof
  • Cefuroxime lysine and preparation thereof
  • Cefuroxime lysine and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Example 1 Preparation of 3-decarbamoyl-acetyl-cefuroxim sodium:

[0078]

[0079] (1) Preparation of 7-aminocephalosporanic acid crystals:

[0080] a-1. Weigh 7-aminocephalosporanic acid and add it to 30 times the weight of water to form a suspension, add 4mol / l ammonia water, stir until the 7-aminocephalosporanic acid is completely dissolved, and the pH of the solution is 6.8;

[0081] a-2. Add 4mol / l hydrochloric acid and an organic solvent, the organic solvent is a mixed solvent with a volume ratio of ethanol and ethyl acetate of 2:1, and the volume of the added organic solvent is 7-aminocephalosporanic acid suspension 2 times of the liquid volume; when the pH value is 3.5, stop adding hydrochloric acid dropwise, and continue to add organic solvent;

[0082] a-3. After adding the organic solvent, grow the crystals for 2 hours, filter, wash, and dry in vacuum to obtain 7-aminocephalosporanic acid crystals. Its X-ray diffraction curve is as Figure 16 shown;

[0...

Embodiment 2

[0100] Example 2. Preparation of 3-decarbamyl cefuroxime acid

[0101]

[0102]a. Measure 32ml of methanol and 18ml of NaOH solution (15%), stir and cool down to -16~-20°C, maintain at this temperature, add the condensation solution and 6ml of water at 2°C dropwise; after adding, keep the temperature of the solution Stir for 15 to 20 minutes at -16 to -20°C;

[0103] b. Add 5.4ml of glacial acetic acid dropwise, heat up the water bath, add 0.10g each of hydrosulfite and ethylenediaminetetraacetic acid (EDTA) when the temperature of the solution reaches 1-4°C, continue stirring, then add 75ml of dichloromethane, at this time, The temperature will rise, and the pH value of the solution will be between 5 and 6;

[0104] c. Add 26ml of HCl solution (16%) dropwise, adjust the pH value of the solution to 2.0, then continue to stir for 30 minutes, cool down to 5°C, and keep stirring for 30 minutes;

[0105] d. Filter, wash with 2°C water three times, dichloromethane twice, drain...

Embodiment 3

[0107] Embodiment 3. The preparation of cefuroxime acid

[0108]

[0109] a. Add 85ml of anhydrous tetrahydrofuran into the reaction flask, cool down to -5~-1°C, add decarbamoylcefuroxine under the condition of nitrogen filling, and stir until completely dissolved;

[0110] b. Cool down the solution to -70°C, and add 5.2ml of chlorosulfonyl isocyanate (CSI) dropwise while continuing to cool down; after the addition, the solution temperature should not exceed -40°C;

[0111] c. Stir rapidly at -40~-50°C for 30 minutes, add dropwise 18ml of 2°C water, keep the solution temperature at 0~5°C, and continue stirring for 10 minutes;

[0112] d. Add NaHCO to the reaction flask 3 solution (NaHCO 3 18.00g + pure water 140ml, warm up to 35-40°C and stir to dissolve), adjust the pH value of the solution between 6.5-7.0;

[0113] e. After stirring for 10 minutes, add 72ml of ethyl acetate, stir well, and the pH of the aqueous phase is 6;

[0114] f. The temperature of the water bath...

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Abstract

The invention relates to a cefuroxime lysine compound. The invention is characterized in that the cefuroxime lysine contains 98-99.99 wt% of cefuroxime lysine and 0.01-2 wt% of descarbamoyl cefuroxime, wherein the molecular formula of the descarbamoyl cefuroxime is disclosed as Formula I. The cefuroxime lysine provided by the invention has higher stability than the cefuroxime lysine in the prior art, and lower impurity content and polymer content than the cefuroxime lysine in the prior art, and is very suitable for clinical application.

Description

technical field [0001] The invention relates to a pharmaceutical composition, in particular to a cefuroxime lysine and a preparation thereof. Background technique [0002] Cefuroxime belongs to the second generation of broad-spectrum cephalosporins. It was successfully developed by Glaxo Wellcome (now GlaxoSmithKline). Xin (Zinacef), and then sold in many countries and regions around the world. It was approved by the US FDA on December 28, 1987, and was launched in the US in 1988. Because of its definite curative effect, broad antibacterial spectrum, low toxicity to the kidneys, strong permeability, and stability to β-lactamase, it is widely used to fight various types of infections caused by sensitive fungi. At present, cefuroxime has been included in "USP 32 Edition-NF27", "British Pharmacopoeia 2009 Edition", "Japanese Pharmacopoeia JP14 Edition", "Chinese Pharmacopoeia 2010 Edition". [0003] In the early 1990s, the drug has become the best-selling anti-infective drug...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34C07D501/04A61K31/546A61P31/04
Inventor 李明杰蒋燕杰王平刘怀彬
Owner SHANDONG LUOXIN PARMACEUTICAL GROUP STOCK CO LTD
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