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Cefpodoxime proxetil impurity cefpodoxime dipivoxil and preparation method thereof

A technology of cefpodoxime axetil and cefpodoxime, which is applied in the field of drug impurity synthesis, can solve the problems that the structure is not listed in the Pharmacopoeia, and achieve the effects of simplified operation, high yield, and improved purity and quality

Pending Publication Date: 2022-02-01
浙江东邦药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] For cefpodoxime axetil, there are also some impurities in the process of synthesis. With our in-depth research on the preparation process and product quality of cefpodoxime axetil for many years, it is also of great significance to find new cefpodoxime axetil impurities. Wherein cefpodoxime dipivoxil (its chemical structural formula is shown in structural formula Ⅱ, and its molecular formula: C 27 h 37 N 5 o 12 S 2 , molecular weight: 687.74) as one of the impurities in the quality control of cefpodoxime axetil, its structure is not listed in the Pharmacopoeia, and there is no relevant report of this impurity in other documents

Method used

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  • Cefpodoxime proxetil impurity cefpodoxime dipivoxil and preparation method thereof
  • Cefpodoxime proxetil impurity cefpodoxime dipivoxil and preparation method thereof
  • Cefpodoxime proxetil impurity cefpodoxime dipivoxil and preparation method thereof

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Embodiment 1

[0028] The structural formula of this cefpodoxime dipivoxil is shown in the following formula I compound:

[0029]

[0030] The concrete preparation method of above-mentioned new impurity cefpodoxime dipivoxil can adopt following method to obtain:

[0031] In a clean reaction flask, 5.58g (0.01mol, 1eq) of cefpodoxime axetil shown in formula II was dissolved in 72g of dichloromethane, and then 6.45g (0.025mol, 2.5eq) of 1-iodoethyliso Propyl carbonate, after stirring evenly, heat up and control the temperature at 30°C to 35°C, add 3.54g (0.035mol, 3.5eq) triethylamine dropwise, the pH of the system is about 9.0, and keep the temperature at 30°C to 35°C Condensation reaction was carried out at 0.5 ℃ for 0.5 hours. After the reaction, the temperature of the reaction solution was lowered and controlled at 5-15°C, and 40mL of dilute hydrochloric acid aqueous solution with a mass percentage of 10% was added to make the pH value about 3.4. Stirring was continued for 15 minutes, a...

Embodiment 2

[0037] The structural formula of this cefpodoxime dipivoxil is shown in the following formula I compound:

[0038]

[0039] The concrete preparation method of above-mentioned new impurity cefpodoxime dipivoxil can adopt following method to obtain:

[0040] In a clean reaction flask, 5.58g (0.01mol, 1eq) of raw material cefpodoxime axetil as shown in formula II was dissolved in 67g of toluene, and then 5.16g (0.02mol, 2.0eq) of 1-iodoethyl isopropyl was added After stirring evenly, heat up and control the temperature at 36°C to 39°C, add 2.77g (0.038mol, 3.8eq) diethylamine dropwise, the pH value is about 9.3, and keep the temperature at 36°C to 39°C Carry out the condensation reaction for 1 hour. After the reaction is over, lower the temperature of the reaction solution and control the temperature at 0-10°C, add 60 mL of 8% by mass percent dilute hydrochloric acid aqueous solution, the pH value is about 3.5, stir for 15 minutes, and let stand to separate layers. Carry out ...

Embodiment 3

[0043] In a clean reaction flask, 5.58g (0.01mol, 1eq) of raw material cefpodoxime axetil shown in formula II was dissolved in 78g of ethyl acetate, and then 6.45g (0.025mol, 2.5eq) of 1-iodoethyl Isopropyl carbonate, after stirring evenly, raise the temperature and control the temperature at 38°C, add 3.84g (0.038mol, 3.8eq) diisopropylamine dropwise, the pH value is about 9.2, and keep the temperature at 38°C ~ 40°C The condensation reaction was carried out at 0.5 hours for 0.5 hours. After the reaction, the temperature of the reaction solution was lowered and controlled at 15°C, and the pH value of the reaction solution was adjusted to about 3.0 by adding 8% by mass percent of dilute hydrochloric acid aqueous solution, stirred for 15 minutes, and allowed to stand for stratification. , perform liquid separation and discard the water layer, then add 8% dilute hydrochloric acid aqueous solution to the organic layer to adjust the pH value of the system to about 3.5, control the ...

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Abstract

The invention relates to a cefpodoxime proxetil impurity, namely cefpodoxime dipivoxil and a preparation method thereof, belonging to the technical field of drug impurity synthesis. The invention aims to provide a novel impurity with high purity and quality. According to the invention, the method comprises the following steps: adding raw materials including cefpodoxime proxetil and 1-iodoethyl isopropyl carbonate into a non-water-soluble benign organic solvent, adding organic alkali to control the pH value of the system to be 8.0-10, carrying out condensation reaction under the condition that a temperature is controlled to be 20-45 DEG C, and obtaining the corresponding product cefpodoxime proxetil impurity, namely cefpodoxime dipivoxil after the reaction is ended. The novel impurity provided by the invention can be used for impurity control of cefpodoxime proxetil synthesis, and has the advantages of high yield and product purity of 93% or more.

Description

technical field [0001] The invention relates to a cefpodoxime axetil impurity cefpodoxime dipivoxil and a preparation method thereof, belonging to the technical field of drug impurity synthesis. Background technique [0002] Cefpodoxime axetil, chemical name is (6R,7R)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino)-acetamido]-3- Methoxymethyl-8-oxo-5-thio-1-azabicyclo-[4,2,0]oct-2-ene-2-carboxylate isopropoxycarbonyloxyethyl ester, developed by Sankyo Corporation of Japan The third-generation oral broad-spectrum cephalosporin has a broad antibacterial spectrum and strong antibacterial effect, and the dosage is small, and the frequency of administration is small, thereby improving the patient's medication compliance. Its molecular formula: C 21 h 27 N 5 o 9 S 2 , Molecular weight: 557.60, the chemical structural formula is shown in structural formula Ⅱ: [0003] [0004] For the process of drug research and development, the quality of drugs is an important criterio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/04C07D501/34C07D501/12
CPCC07D501/04C07D501/34C07D501/12
Inventor 周军荣李日生王胜池骋芮立涛王干高扬
Owner 浙江东邦药业有限公司
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