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Synthesis method of cefradine

A synthesis method and technology of cefradine, applied in the field of drug synthesis, can solve problems such as affecting the crystal form and product stability of cefradine

Active Publication Date: 2010-02-10
哈药集团股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Yet existing synthetic method carries out C4-position carboxyl and C7-position amino protection and preparation active dihydrophenylglycine when 7-ADCA, the protective agent that uses enters hydrolyzate with reaction solution, has influenced the crystal form of cephradine and the product stability

Method used

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  • Synthesis method of cefradine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 1. Condensation

[0025] Add 75g of dihydrophenylglycine sodium salt, 400ML of dichloromethane, 20ML of DMA, and 0.1ML of 4-picoline into a 1000ML three-necked bottle; cool down to -20~-25°C, and add 49.0g of carbonyldiimidazole in portions , the reaction is exothermic, the speed of addition should not be too fast, and the temperature should not be higher than -20°C. The reaction was stirred at ℃ for 120 minutes, and the condensation reaction was completed.

[0026] 2. Hydrolysis and decolorization

[0027] Pour the condensation solution into a 2000ML beaker, start stirring, add 300ML of purified water, DMA32ML into the 2000ML beaker, stir evenly, control the temperature at 29-33°C, adjust the pH value to 0.6-0.8 with concentrated hydrochloric acid, then add the hydrolyzate In the separating funnel, let it rest fully, remove the dichloromethane phase, collect the water phase into a 500ML beaker, add an appropriate amount of activated carbon, stir for 10 minutes, and f...

Embodiment 2

[0033] Add 70g of dihydrophenylglycine sodium salt, 400ML of dichloromethane, 25ML of DMF, and 0.2ML of 4-picoline into a 1000ML three-necked bottle; cool down to -20~-25℃, and add 49.8g of carbonyldiimidazole in portions , the reaction is exothermic, the speed of addition should not be too fast, and the temperature should not be higher than -15°C. The reaction was stirred at ℃ for 120 minutes, and the condensation reaction was completed.

[0034] Post-reaction treatment such as crystallization, steps such as washing and drying are the same as in Example 1.

Embodiment 3

[0036] Add 82g of dihydrophenylglycine sodium salt, 400ML of chloroform, 30ML of DMA, and 0.3ML of 4-picoline into a 1000ML three-necked flask; cool down to -20~-25°C, add 63.3g of carbonyldiimidazole in portions, and react Exothermic, the speed of addition should not be too fast, the temperature should not be higher than -15°C, after the dropwise addition, control the temperature at -25~-30°C, keep it for 45 minutes, then add 50g of 7-ADCA, at -20~-25°C The reaction was stirred for 120 minutes, and the condensation reaction was completed.

[0037] Post-reaction treatment such as crystallization, steps such as washing and drying are the same as in Example 1.

[0038] The comparison of technical quality indicators of the above implementation schemes is shown in the table below:

[0039]

[0040]

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Abstract

The invention relates to a synthesis method of cefradine, comprising the following steps: using dihydro phenylglycine sodium dane saltand carbonyldiimidazole to prepare active amide in anhydrous solvent, then performing a reaction between active amide and 7-ADCA and finally hydrolyzing and crystallizing after the reaction to obtain cefradine.

Description

technical field [0001] The invention relates to a method for synthesizing medicine, in particular to a method for synthesizing antibacterial drug cefradine. The method is simple and easy to operate, and the crystal form and stability of the obtained product are good. Background technique [0002] Cephradine is also known as cyclohexenylamine cephalosporin, cyclohexenylglycinamide cephalosporin, cephalosporin VI, etc. It was created by Bristol-Myers Squibb in 1972. [0003] The synthetic method of ceboradine is divided into enzymatic method and chemical synthesis method. Enzymatic synthesis of ceboradine is to use penicillin acylase to catalyze the reaction, but the catalytic enzyme is not only expensive, but also the catalytic performance is easily affected by pH value, temperature, ionic strength, etc., and there are also products and by-products in the reaction process. Inhibition of the reaction, at present, the enzymatic method is not suitable for the industrial product...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/22C07D501/06A61P31/00
Inventor 金乃岩朱彦民马杰唐宝华王力学牟春福杨滨王高升
Owner 哈药集团股份有限公司
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