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Synthetic method of nifuratel

A synthetic method, the technology of nifuratel, applied in the field of drug synthesis, can solve the problems of low reaction rate and yield, many impurities in the product, explosion hazard, etc., and achieve the effect of easy control of the process, easy availability of raw materials, and reduction of pollution

Active Publication Date: 2014-05-28
SHANDONG LUOXIN PARMACEUTICAL GROUP STOCK CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But above-mentioned synthesis method is all carried out in the alkaline environment of methyl alcohol-sodium methylate, and in the production of industrial scale, owing to using metal sodium, can bring the danger of explosion
In addition, the reaction rate and yield of above-mentioned synthetic method are all lower, and product impurity is many, purity is low

Method used

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  • Synthetic method of nifuratel
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  • Synthetic method of nifuratel

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Embodiment 1: the process condition optimization of the synthetic method step 1 of nifuratel

[0029] During the synthesis process of nifuratel, the present invention investigates the effect of the temperature of the substitution reaction described in step 1 of the synthesis method of nifuratel on the color of the reaction solution and the yield of 2-(methylthiomethyl)-oxirane The results are shown in Table 1.

[0030] Table 1 Process conditions of step 1

[0031] temperature reflex

[0032] As can be seen from the results in Table 1, in the synthetic process of nifuratel, the higher the substitution reaction temperature described in step 1, the more yellow impurities generated, and the yield of intermediate 2-(methylthiomethyl)-oxirane lower. Therefore, the reaction temperature is determined to be 0-10°C. Further detection of the reaction product between the residual liquid and sodium methylmercaptide after distillation showed that no 2-(methylthiomethyl)...

Embodiment 2

[0033] Embodiment 2: the process condition optimization of the synthetic method step 2 of nifuratel

[0034] During the synthesis of nifuratel, the post-treatment method of the intermediate 3-methylthio-2-hydroxyl-propylhydrazine further prepared by the present invention was studied, and the results are shown in Table 2.

[0035] Table 2 The post-treatment process conditions of 3-methylthio-2-hydroxyl-propylhydrazine

[0036]

[0037] As can be seen from the results in Table 2, in the synthetic process of nifuratel, if the reaction solution is not subjected to high vacuum distillation, the quality of the final nifuratel product will be more affected. Therefore, it is determined that the reaction solution is first evaporated to remove hydrazine hydrate and water at a lower temperature and vacuum, and then distills high-purity 3-methylthio-2-hydroxyl-propylhydrazine under high vacuum.

Embodiment 4

[0038] Embodiment 4: the process condition optimization of the synthetic method step 3 of nifuratel

[0039] During the synthesis process of nifuratel, the present invention investigated the influence of different hydrolysis solvents on the preparation of intermediate 5-nitrofurfural and the final product, and the results are shown in Table 3.

[0040] The influence of table 3 different solvents on the preparation of intermediate 5-nitrofurfural

[0041] Hydrolysis solvent

[0042] As can be seen from the results in Table 3, compared with dilute hydrochloric acid, 5-nitrofurfural diethyl ester was refluxed in dilute sulfuric acid and hydrolyzed for 30 minutes to easily obtain 5-nitrofurfural solution, and the final nifuratel product quality was also qualified Therefore, it is determined to use the process of hydrolyzing 5-nitrofurfural diethyl ester in dilute sulfuric acid.

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Abstract

The invention belongs to the field of medicine synthesis, and discloses a synthetic method of nifuratel. The synthetic method of nifuratel is to carry out ring closing reaction under the alkaline condition of sodium methoxide, therefore, the metallic sodium can be avoided being used, and the safety in production can be ensured; meanwhile, the reaction is easy to generate, the process is easy to control, high yield of the synthesized nifuratel is achieved, few impurities are generated, and the quality is stable; and moreover, the synthetic method of nifuratel is simple in operation, and the raw material is easy to obtain; the used solvent and the raw material out of the reaction can be recycled along with low cost; no waste liquid is generated in each step of the reaction; the pollution is greatly reduced; and the synthetic method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a method for synthesizing nifuratel. Background technique [0002] Nifuratel (Cefditoren Pivoxil) chemical name: 5-[(methylthio)methyl]-3-[[(5-nitro-2-furan)methylene]amino]-2-oxazolidine Ketone, the molecular formula is C10H11N3O5S, the molecular weight is 285.28, and the chemical structure formula is as follows: [0003] [0004] Nifuratel was developed and marketed by Poli Industria Chimica S.p.A in Italy in the 1960s. It is a nitrofuran antibiotic drug that has a significant effect on treating mixed vaginal infections. Its trichomonadicidal activity is equivalent to that of metronidazole. It has antibacterial effect and can effectively kill Chlamydia trachomatis and Mycoplasma, and has certain activity on Candida. Oral and vaginal administration of nifuratel shows that it is well tolerated and has no drug resistance. The cure rate for bacterial vaginosis is equivalent to th...

Claims

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Application Information

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IPC IPC(8): C07D413/12
Inventor 刘新泉王平刘明霞李晓峰
Owner SHANDONG LUOXIN PARMACEUTICAL GROUP STOCK CO LTD
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