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Cefoxitin anhydrous crystal, preparation method thereof and method for preparing cefoxitin sodium by using same

A technology for cefoxitin acid and anhydrous crystallization, which is applied in the field of preparation of pharmaceutical compounds, and can solve problems such as incomplete crystallization, high total impurities of cefoxitin acid hydrate, and impact on product yield

Inactive Publication Date: 2013-01-02
SHENZHEN SALUBRIS PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] The total impurities of cefoxitin acid hydrate currently on the market are high
Adopt above-mentioned technology to produce cefoxitin acid in addition and there is following problem: because crystallization is water phase crystallization, need add organic solvent to regulate crystal form, thereby crystallization is incomplete, influences the yield of product

Method used

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  • Cefoxitin anhydrous crystal, preparation method thereof and method for preparing cefoxitin sodium by using same
  • Cefoxitin anhydrous crystal, preparation method thereof and method for preparing cefoxitin sodium by using same
  • Cefoxitin anhydrous crystal, preparation method thereof and method for preparing cefoxitin sodium by using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Take 10g of cefoxitin acid hydrate, add it to the reaction flask, raise the temperature to 36°C, add tetrahydrofuran and stir until it dissolves completely, concentrate under reduced pressure to 50-70mL, add dichloromethane dropwise to make the solution cloudy. Cultivate the crystal at 20° C. for half an hour, add dichloromethane to dilute, and continue to grow the crystal at room temperature for half an hour. After filtering, the filter cake was washed with dichloromethane, and the temperature was controlled at 40° C. to dry under vacuum to obtain white crystals of cefoxitin anhydrous. Agilent1200 reversed-phase high-performance liquid phase detection its purity is 99.838% (as Figure 7 Shown), the K-F method measures its water content as 0.28%.

[0046] Gained cefoxitin acid anhydrous crystalline product adopts melting point measuring instrument to measure its melting point to be 152~153 ℃, and its X-ray diffraction pattern is as follows Figure 5As shown, its infra...

Embodiment 2

[0050] Take 10g of cefoxitin acid hydrate, add it to the reaction bottle, raise the temperature to 36°C, add ethanol and stir until it dissolves completely, concentrate under reduced pressure to 50-70mL, add dichloromethane dropwise to make the solution cloudy. Cultivate the crystal at 20° C. for half an hour, add dichloromethane to dilute, and continue to grow the crystal at room temperature for half an hour. After filtering, the filter cake was washed with dichloromethane, and the temperature was controlled at 40° C. to dry under vacuum to obtain white crystals of cefoxitin anhydrous. Agilent1200 reversed-phase high-performance liquid phase detection its purity is 99.747%, and its water content is 0.45% as determined by K-F method.

[0051] The obtained cefoxitin acid anhydrous crystalline product is measured by a melting point detector and has a melting point of 152-153°C. The X-ray diffraction pattern of the product prepared in this example is basically consistent with th...

Embodiment 3

[0053] Take 10 g of the anhydrous cefoxitin acid crystals prepared in the above examples and dissolve them in a mixed solution of 40 mL of methanol and 60 mL of acetone, and add dropwise a solution containing 5.5 g of sodium isooctanoate (sodium 2-ethylhexanoate) at a temperature of about 5° C. and 50mL of methanol, and then add 250mL of acetone to precipitate a solid. The solid is suction filtered, washed with acetone, and dried in vacuo to obtain about 9.6 g of cefoxitin sodium.

[0054] The cefoxitin sodium obtained in this example and the cefoxitin sodium prepared by cefoxitin acid hydrate are measured by the first method of solution color inspection in the Chinese Pharmacopoeia 2010 edition, the color level of the former is less than Y1 and the color level of the latter is less than Y4 . The color level of the cefoxitin sodium prepared from the anhydrous cefoxitin acid crystal of the present invention is significantly reduced, and has a good application prospect.

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Abstract

The invention provides a cefoxitin anhydrous crystal. Peaks exist at 2theta angles of 12.0 degrees, 15.7 degrees, 18.8 degrees and 22.6 degrees of the X-ray diffraction pattern of the crystal. In a differential thermal analysis diagram, an endothermic peak exists at 170.0 degrees and exothermic peak exists at 172.7 degrees. The invention additionally provides a method for preparing the cefoxitin anhydrous crystal and a method for preparing cefoxitin sodium by using the cefoxitin anhydrous crystal. The impurity content of the cefoxitin anhydrous crystal is low, the color level of the cefoxitinsodium is reduced and the application prospect of cefoxitin acid drugs is improved.

Description

technical field [0001] The invention belongs to the field of preparation of pharmaceutical compounds, in particular to a new cefoxitin acid anhydrous crystal and a preparation method thereof, and further relates to a method for preparing cefoxitin sodium from the cefoxitin acid anhydrous crystal. Background technique [0002] Cefoxitin, chemical name: (6R,7S)-3-carbamoyloxymethyl-7-methoxy-8-oxo-7-[2-(-thienyl)acetyl] -5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is a semi-synthetic cephalosporin antibiotic developed by Merck Company of the United States. Its chemical structural formula is as follows: [0003] [0004] Cefoxitin acid is practically insoluble in water, while its sodium salt is easily soluble in water. For the convenience of clinical use, its sodium salt is currently made into pharmaceutical preparations for the treatment of bacterial infections. Cefoxitin Sodium was first approved for marketing under the trade name "Cenomycin" by Japan's Daiich...

Claims

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Application Information

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IPC IPC(8): C07D501/57C07D501/04C07D501/12
Inventor 陈碧陈伟
Owner SHENZHEN SALUBRIS PHARMA CO LTD
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