Preparation method of cefminox sodium

A technology of cefminox sodium and cefminox sodium, which is applied in the direction of organic chemistry, can solve the problems of affecting product quality and yield, high price, and unavoidable hydrolysis, so as to improve product purity, increase product yield, and inhibit The effect of side effects

Active Publication Date: 2012-08-22
山东安弘制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This process uses expensive and highly toxic trifluoroacetic acid, and the product yield is low, which is not conducive to industrial production
[0010] In the synthetic method of cefminox sodium in the prior art, the method of introducing D-cysteine ​​on the 7β-amide group is to carry out the condensation rea

Method used

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  • Preparation method of cefminox sodium
  • Preparation method of cefminox sodium
  • Preparation method of cefminox sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] A preparation method for cefminox sodium, comprising the steps of:

[0045] (1) Add 20.0 g of anhydrous D-cysteine ​​to 200 ml of methanol to prepare D-cysteine-methanol suspension; Add 90.0 g of sodium methoxide solution with a concentration of 30 wt % to the cystine-methanol suspension, and stir for 20 minutes to prepare a solution containing D-cysteine ​​sodium thiolate (the structural compound of formula (IV));

[0046] (2) 1 L of ethyl acetate solution containing the compound of the formula (III) structure (43.5 g of the compound containing the formula (III) structure, the specific impurity IMP detected by HPLC is 0.65% (254nm, detected by the area normalization method, the same below )), concentrated under reduced pressure at 30°C and a pressure of -0.1MPa until the concentration of the compound of the formula (III) structure was 500g / L, cooled to 10°C, and added 300ml of methanol to obtain the compound containing the formula (III) structure The solution of the c...

Embodiment 2

[0055] Preparation method as described in Example 1, the difference is that,

[0056] In step (3), directly filter without adding ethyl acetate 600ml.

[0057] The weight of the obtained cefminox sodium heptahydrate is 53.5g, the yield is 79.5%, the product content is 99.1%, the HPLC purity is 99.5%, and the specific impurity IMP is 0.04%.

[0058] The obtained product was confirmed for its structure, and the data result was the same as the structure confirmed data of Example 1.

Embodiment 3

[0060] Preparation method as described in Example 1, the difference is that,

[0061] Methanol in the step (1) and step (2) is replaced by dimethyl sulfoxide.

[0062] The weight of the obtained cefminox sodium heptahydrate is 58.6g, the molar yield is 86.8%, the product content is 98.9%, the HPLC purity is 99.2%, and the specific impurity IMP is 0.07%.

[0063] The obtained product was confirmed for its structure, and the data result was the same as the structure confirmed data of Example 1.

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Abstract

The invention relates to a preparation method of cefminox sodium, which comprises the following steps of: (1) dispersing a compound with a structure shown in formula (V) in specific organic solvent, and then adding sodium methoxide; (2) replacing the solvent in ethyl acetate I containing a compound with a structure shown in formula (III) with specific organic solvent by a reduced-pressure concentration manner; (3) mixing a solution or suspension containing the compound with the structure shown in formula (IV) with a solution containing the compound with the structure shown in the formula (III), carrying out condensation reaction and separating to obtain anhydrous cefminox sodium with the structure shown in formula (II); and (4) transforming anhydrous cefminox sodium into cefminox sodium heptahydrate crystal in the presence of water. Compared with the traditional condensation reaction in an aqueous solution, the method is more favorable to reducing specific impurity in the product and improving product purity and yield.

Description

technical field [0001] The invention relates to a preparation method of cefminox sodium, which belongs to the technical field of medicinal chemical synthesis. Background technique [0002] Cefminox sodium, its English name is Cefminox Sodium, its chemical name is: (6R, 7S)-7-[(S)-2-(2-amino-2-carboxyethylmercapto) acetamido]-7-methoxy Base-3-[[(1-methyl-1H-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene -2-Sodium carboxylate, generally exists in the form of heptahydrate crystals, molecular formula: C 16 h 20 N 7 NaO 7 S 3 ·7H 2 O, molecular weight 667.67, structural formula: [0003] [0004] Cefminox sodium is a third-generation cephalosporin antibiotic, which is a semi-synthetic cephamycin derivative. There is a trans-methoxyl group at the 7-position of the β-lactam ring of cefminox sodium, which makes cefminox sodium highly stable to β-lactamase, so it has the same effect on β-lactamase-producing bacteria as non-producing β-lactamase - Effect of la...

Claims

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Application Information

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IPC IPC(8): C07D501/57C07D501/04
Inventor 符淙淙许洪飞汤沸王勇进
Owner 山东安弘制药有限公司
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