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Preparation method of cefixime delta 3 isomer impurity

A technology of cefixime and isomers, which is applied in the field of preparation of cefixime △3 isomer impurities, achieves the effects of low requirements for reaction equipment, mild reaction conditions, and cost reduction

Inactive Publication Date: 2020-09-01
心邀(深圳)生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, since the △3 isomer impurity of cefixime is a specific impurity, and this impurity is rarely sold in the market, the specific impurity is of great value to the quality control and safety assessment of cefixime drugs, so the study of cefixime The synthesis of oxime △3 isomer impurity has very important practical significance

Method used

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  • Preparation method of cefixime delta 3 isomer impurity
  • Preparation method of cefixime delta 3 isomer impurity
  • Preparation method of cefixime delta 3 isomer impurity

Examples

Experimental program
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Embodiment 1

[0044] As attached figure 1 The reaction scheme shown in the reaction scheme for the preparation of cefixime △3 isomer impurities includes the following specific steps:

[0045] a: (6R, 7R)-methyl 7-((Z)-2-(2-aminothiazol-4-yl)-2-((2-2-methoxy-2-oxyethoxy) sub Synthesis of amino)acetamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (Intermediate 1).

[0046] Add cefixime 9.06g (20mmol) and 35mL of anhydrous methanol to a dry 100mL single-necked flask. Add 4.55g (45mmol) of triethylamine slowly with stirring in an ice bath, and then slowly add 5.35g (45mmol) of thionyl chloride. ), after dropping, the temperature is controlled at 65°C and the reaction is refluxed and stirred for 4 hours, and the solvent is removed by rotary evaporation at 40°C. 25mL of dichloromethane is added. After stirring to clear, 50mL of methyl tert-butyl ether is slowly added dropwise to the reaction solution. Become turbid, slowly stir for 20 minutes under temperature control in an ice ...

Embodiment 2

[0052] The hydrogen spectrum and carbon spectrum of the cefixime Δ3 isomer impurities prepared in Example 1 were analyzed to further confirm its structure.

[0053] 1. Hydrogen spectrum analysis

[0054] The number of the impurity hydrogen atom of cefixime △3 isomer is as follows:

[0055]

[0056] The analysis results of the hydrogen spectrum of cefixime △3 isomer impurities are shown in Table 1 below:

[0057] Table 1: Analytical results of hydrogen spectrum of cefixime delta 3 isomer impurities.

[0058] H serial number H type H number chemical shift 1 =CH-16.66 2 =CH-1 6.30~6.37 3=CH 2

[0059] 2. Carbon spectrum analysis

[0060] The number of carbon atoms of cefixime △3 isomer impurity is as follows:

[0061]

[0062] The carbon spectrum analysis results of cefixime △3 isomer impurities are shown in Table 2 below:

[0063] Table 2: Results of carbon spectrum analysis of cefixime delta 3 isomer impurities.

[0064] C serial number Type C chemical shift 1＝C-122.51 2 =C123.62 3＝...

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Abstract

The invention relates to the technical field of organic synthesis, and provides a preparation method of a cefixime delta 3 isomer impurity. The preparation method comprises the following steps: a, catalyzing esterification of cefixime and methanol by using sulfoxide chloride to obtain an intermediate 1; b, performing high-temperature reaction on the intermediate 1 under the catalysis of an alkali,and performing column chromatography purification to obtain an intermediate 2; and c, hydrolyzing the intermediate 2 with an alkali at low temperature to obtain the cefixime delta 3 isomer impurity.The synthesis method provided by the invention can realize synthesis of the cefixime impurity, and can be used for further researching cefixime-related quality and improving the medication safety, reliability and stability of related preparations. And the method has a great promotion effect on the quality control of the production process of crude drugs and related preparations.

Description

Technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for preparing cefixime delta 3 isomer impurities. Background technique [0002] Cefixime is a broad-spectrum, high-efficiency and enzyme-resistant third-generation oral cephalosporin developed by Japan's Fujisawa Pharmaceutical Co., Ltd. After being marketed in Japan and the United States in 1987 and 1989, respectively, it has been widely used in clinical practice in more than 80 countries in 1999. Cefixime binds to penicillin-binding proteins (PBPs) to inhibit the cell wall synthesis of the dividing cells of bacteria, thereby causing excessive growth and expansion of cell contents to rupture, causing leakage of cell contents and killing cells. It has the characteristics of wide antibacterial spectrum, strong bactericidal power, acid resistance, and high stability to β-lactamase. Clinically, it is mainly used for respiratory infections, urinary system infections, ...

Claims

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Application Information

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IPC IPC(8): C07D501/04C07D501/60
CPCC07D501/04C07D501/60
Inventor 翁韶潮陈帮昱
Owner 心邀(深圳)生物科技有限公司
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