Novel technique for synthesizing cefoselis sulfate

A cefotaxime sulfate, a new process technology, applied in the direction of organic chemistry, etc., can solve the problems of difficulty in purchasing cephalosporin nuclei raw materials, limited application prospects, harsh reaction conditions, etc., and achieve low cost, simple synthesis process route, and easy operation Effect

Inactive Publication Date: 2009-02-04
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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Problems solved by technology

[0003] So far, the synthesis of cefotaxime sulfate has 7-tert-butoxycarbonyl-amino-3 chloromethyl-3-cephem-4-carboxylic acid diphenylmethyl ester, ACLE, etc. as raw materials, respectively in C- The introduction of 5-amino-1-hydroxyethylpyrazole at the 3' position and the introduction of 2-cis-methoxyimino-2-(2-aminothiazolyl-4)-acetyl at the 7β position are realized. These methods The yields are not high, and the cephalosporin nuclei raw materials are difficult to purchase, and the reaction conditions are harsh, which limits its application prospects. Therefore, it is urgent to develop a synthetic route with low cost, simple operation, and easy-to-obtain raw materials to synthesize Cefotaxime Sulfate

Method used

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  • Novel technique for synthesizing cefoselis sulfate
  • Novel technique for synthesizing cefoselis sulfate
  • Novel technique for synthesizing cefoselis sulfate

Examples

Experimental program
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Embodiment 1

[0019] Embodiment 1, the synthesis of cefotaxime sulfate:

[0020] (1) Iodide 7β-phenylacetamido-3-[3-carboxamido-2-(2-formyloxyethyl)-pyrazolium]methyl-3-cephem-4-carboxylic acid pair Synthesis of Methoxybenzyl:

[0021] Dissolve 80 grams of GCLE and 30 grams of sodium iodide in 90 mL of DMF, stir and react at room temperature for 30 minutes in the dark under nitrogen protection, add 94 grams of 5-formamido-1-(2-formyloxyethyl)-pyrazole, and perform a high-efficiency liquid phase The reaction process was monitored by chromatography; after the reaction was complete, a small amount of acetone was added, and then added to stirred water to precipitate a precipitate, which was filtered and washed with water. vacuum drying;

[0022] (2) Synthesis of 7β-phenylacetamido-3-[3-carboxamido-2-(2-formyloxyethyl)-pyrazolium]methyl-ceph-3-ene-4-carboxylic acid :

[0023] Mix 80.0 g of the above-mentioned compound and 93.2 g of phenol and stir at 50° C., react, follow the reaction by hig...

Embodiment 2

[0030] Embodiment 2, cefotaxime sulfate analogue obtains synthesis:

[0031] (1) Synthesis of 7β-phenylacetamido-3-[1-(2-ethyl)-pyrazolium]methyl-ceph-3-ene-4-carboxylic acid:

[0032] Dissolve 3.3 grams of GCLE and 30.8 grams of sodium iodide in DMF90mL, stir and react at room temperature in the dark for 30 minutes, add 50 grams of ethylpyrazole, and monitor the reaction process by high performance liquid chromatography; after the reaction is complete, add a small amount of acetone, and then add to In the stirred water, a precipitate precipitated out, filtered and washed with water. vacuum drying;

[0033] (2) Synthesis of 7β-phenylacetamido-3-[1-(2-ethyl)-pyrazolium]methyl-ceph-3-ene-4-carboxylic acid:

[0034] Mix 43.5 grams of the above-mentioned compound and 60 grams of phenol and stir at 50°C, react, and follow the reaction with high performance liquid chromatography. After the reaction is complete, add acetone, and then add isopropyl ether to precipitate, filter, and ...

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Abstract

The invention discloses a new synthesis technology of cefoselis sulfate and analogues thereof. 7-phenylacetyl-3-chloromethyl cephalosporin p-methoxy benzylester (GCLE) is taken as raw material. The synthetic method has the advantages of cheap iodized agents, simple synthesis route, convenient operation, higher synthesis efficiency and low cost.

Description

technical field [0001] The invention relates to a medicine preparation process, in particular to a new synthesis process of the fourth-generation cephalosporin antibiotic cefotaxime sulfate and its analogues. technical background [0002] Cefoselis sulfate (Cefoselis sulfate) belongs to the fourth generation cephalosporin antibiotics. The drug was jointly developed by Fujisawa Pharmaceutical Company of Japan and Johnson Company of the United States, and was first listed in Japan in 1998. Its trade name is FK- 037, is a typical representative of the fourth-generation cephalosporin antibiotics. At present, the excellent antibacterial effect of the drug in vitro and in animal infection models has been confirmed by a large number of clinical experiment reports worldwide. It has been successfully applied at home and abroad: (1) surgical infection, (2) respiratory tract infection; (3) obstetric and gynecological infection; (4) ophthalmic infection, etc. [0003] So far, the synt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/46
Inventor 黄朋勉陈立功杨道武段学民陈平李浔
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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