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Cefotaxime sodium preparation method

A technology of cefotaxime sodium and cefotaxime acid is applied in the field of preparation of antibacterial drug cefotaxime sodium, can solve problems such as unfavorable production, research and utilization, unprotected functional groups, easy oxidative degradation and the like, and achieves improvement of market competition Good strength and color grade, reducing the effect of degradation process

Active Publication Date: 2019-04-05
辽宁美亚制药有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the above process, due to the unprotected active functional groups such as 7-ACA amino carboxyl group, it is easy to be oxidized and degraded during the reaction process, and the result of high impurities
Moreover, the color grade of the obtained product is relatively high, which is not conducive to subsequent production, research and utilization

Method used

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  • Cefotaxime sodium preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0068] Add 500ml of chloroform, 20g of 7-aminocephalosporanic acid, and 22g of HMDS at room temperature. Raise the temperature and heat to reflux for 5-6.0hr, then lower the temperature to below 20°C and add 28g of AE-active ester to condense for 12-15hr.

[0069] Then add 300 ml of 8% aqueous sodium bicarbonate solution for extraction, add 2 g of active carbon to the water phase for decolorization and filter for 20 min. Control the temperature of the filtrate below 30°C, add 130ml of acetone and 65ml of n-butanol, add dropwise dilute acid solution to adjust the pH to 2.8-3.0, and precipitate crystals. After filtering, the filter cake was washed with pure water, and then washed with acetone after draining, dried and discharged to obtain crude cefotaxime acid, with a yield of 85%.

[0070] The purity of high-pressure liquid phase is 99.6%, and the color is yellow-green≤2#. (see attached figure 1 )

Embodiment 1-2

[0072] Add 300ml of anhydrous methanol into the reactor, add 15g of sodium acetate, and stir to dissolve. Then add 45 g of crude product of cefotaxime acid, stir and dissolve. Add 2 g of activated carbon, decolorize for 20 min, and filter. Acetone was added dropwise to the filtrate until cloudy. Crystal growth 60min. Then acetone was added dropwise in the later stage, the temperature was lowered to 0-5°C, and the crystal was grown for 60 minutes. Suction filtration and drying to obtain cefotaxime sodium with a yield of 87%.

[0073] The purity of high-pressure liquid phase is 99.6%, and the color is yellow-green≤2#. (see attached figure 2 )

Embodiment 2-1

[0075] At room temperature, 300 ml of dichloromethane, 20 g of 7-aminocephalosporanic acid, and 35 g of BSU were added. Raise the temperature and heat to reflux for 5-6.0hr, then lower the temperature to below 20°C and add 30g of AE-active ester to condense for 12-15hr.

[0076] Then add 200ml of 6% aqueous sodium hydroxide solution for extraction, add 2g of activated carbon to the water phase for decolorization and filter for 20min. Control the temperature of the filtrate below 30°C, add 130ml of tetrahydrofuran and 65ml of n-butanol, add dropwise dilute acid solution to adjust the pH to 2.8-3.0, and precipitate crystals. After filtering, the filter cake was washed with pure water, drained and then washed with tetrahydrofuran, dried and discharged to obtain crude cefotaxime acid with a yield of 88%.

[0077] The purity of high-pressure liquid phase is 99.6%, and the color is yellow-green≤2#. (see attached image 3 )

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Abstract

The invention provides a cefotaxime sodium preparation method. The method is characterized in that after an active group of 7-aminocephalosporanic acid is protected by a silanization reagent, subjecting to condensation reaction with AE-active ester to generate cefotaxime acid containing a protecting group; after deprotection of the cefotaxime acid containing the protecting group under the action of a deprotection agent, sequentially subjecting to aqueous-phase acidification and crystallization to obtain cefotaxime acid; subjecting the cefotaxime acid to salification and solvent crystallizationto obtain a pure product of cefotaxime sodium. In a whole technical process, a product degradation process is reduced, product quality is evidently improved, product market competitiveness is improved, and medication safety is further guaranteed.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of antibacterial drug cefotaxime sodium. Background technique [0002] The chemical name of cefotaxime sodium is (6R,7R)-3-[(acetoxy)methyl]-7-[(2-amino-4-thiazolyl)-(methoxyimino)acetamido] -Sodium 8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate. It is the third-generation cephalosporin antibiotic product for injection. [0003] At present, the technology of this variety is mainly 7-aminocephalosporanic acid and 2-methoxyimino-2-(2-amino-4-thiazolyl)-(z)-phenylhydrazolyl thioacetate in dichloromethane or 2 - adding cefotaxime acid to a solvent such as methyl tetrahydrofuran, then adding organic alcohol and other solvents, adding dilute acid dropwise to adjust the pH and crystallization, and centrifuging to obtain a completely dried cefotaxime acid solid. [0004] Afterwards, the dried solid pure product is formed into a sodium salt in an aqueous s...

Claims

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Application Information

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IPC IPC(8): C07D501/34C07D501/04C07D501/12
CPCC07D501/04C07D501/12C07D501/34Y02P20/55
Inventor 于永宏侯微王凤一
Owner 辽宁美亚制药有限公司
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