Preparation method of cefpirome hydriodate

A technology for cefpirome hydroiodide and cephalosporin, which is applied in the field of preparation of cefpirome hydroiodide, can solve the problems of unqualified product quality, high hydroiodide, and high residue of finished products, and achieves energy saving and mild reaction conditions. , the effect of reducing costs

Inactive Publication Date: 2014-02-26
HARBIN PHARMA GRP CO LTD GENERAL PHARMA FACTORY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Cefpirome hydroiodide is an important intermediate product in the process of synthesizing cefpirome sulfate, but in the step of preparing cefpirome hydroiodide, the prior art is to add the mixed solution of potassium iodide and hydrochloric acid (or bromide Mixed solution of potassium and hydrochloric acid) to crystallize, so that there is a small amount of potassium iodide residue in cefpirome hydroiodide, resulting in high residue of hydroiodide, mostly more than 10%, and it is difficult to effectively remove it through refining, resulting in the finished product The residue is high, exceeds the pharmacopoeia standard, and the product quality is unqualified

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Add 3000ml of dichloromethane to a 5000ml four-neck bottle, cool down in an ice bath to below 5°C, add 670g of iodotrimethylsilane under nitrogen protection, and then add dropwise a mixture of 510g of 2,3-cyclopentenopyridine and 500ml of dichloromethane , the process temperature does not exceed 10°C. After the dropwise addition is completed, stir in an ice bath for 30 minutes, add 200 g of cefotaxime acid, remove the ice bath, stir at room temperature for 30 minutes, heat to 35 ° C for 2 hours, stop heating, cool the ice bath to below 5 ° C, add 1200 ml of 4N hydrochloric acid, Stir for about 5 minutes, stop stirring, and put it in the refrigerator to grow crystals overnight. The next day, filter with suction, wash the material three times with 500ml acetone, and dry it under vacuum at 30°C for 10 hours. Finally, 240 g of cefpirome hydroiodide was obtained with a molar yield of 85% and no residue.

Embodiment 2

[0018] Add 3000ml of dichloromethane to a 5000ml four-neck bottle, cool down in an ice-water bath to below 5°C, add 600g of iodotrimethylsilane under nitrogen protection, and then add dropwise a mixture of 510g of 2,3-cyclopentenopyridine and 500ml of dichloromethane , the process temperature does not exceed 10°C. After the dropwise addition, stir in the ice bath for 30 minutes, add 200g of cefotaxime acid, remove the ice bath, stir at room temperature for 30 minutes, heat to 35°C for 2 hours, stop heating, cool down in the ice bath to below 5°C, add 1200ml of 4N hydrochloric acid, and stir After about 5 minutes, stop stirring and put it in the refrigerator to grow crystals overnight. The next day, filter with suction, wash the material three times with 500ml acetone, and dry it under vacuum at 30°C for 10 hours. Finally, 230 g of cefpirome hydroiodide was obtained with a molar yield of 81.4% and no residue.

Embodiment 3

[0020] Add 3000ml of dichloromethane to a 5000ml four-neck bottle, cool down in an ice-water bath to below 5°C, add 600g of iodotrimethylsilane under nitrogen protection, and then add dropwise a mixture of 500g of 2,3-cyclopentenopyridine and 500ml of dichloromethane , the process temperature does not exceed 10°C. After the dropwise addition, stir in the ice bath for 30 minutes, add 200g of cefotaxime acid, remove the ice bath, stir at room temperature for 30 minutes, heat to 35°C for 2 hours, stop heating, cool down in the ice bath to below 5°C, add 1200ml of 4N hydrochloric acid, and stir After about 5 minutes, stop stirring and put it in the refrigerator to grow crystals overnight. The next day, filter with suction, wash the material three times with 500ml acetone, and dry it under vacuum at 30°C for 10 hours. Finally, 220 g of cefpirome hydroiodide was obtained with a molar yield of 77.9% and no residue.

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PUM

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Abstract

The invention discloses a preparation method of cefpirome hydriodate. According to the method, under a condition of the presence of excess trimethyliodosilane in a reaction system, dilute hydrochloric acid is used for replacing a mixed liquid of potassium iodide and hydrochloric acid in the prior art for crystallization, thus cefpirome hydriodate residues are reduced to zero, and at the same time, the product yield is ensured.

Description

technical field [0001] The invention relates to the preparation of a cephalosporin medicine, in particular to the preparation of cefpirome hydroiodide. Background technique [0002] Cefpirome is an excellent new variety among the fourth-generation cephalosporins. It has strong antibacterial effect and wide antibacterial spectrum. Lanella, Pseudomonas) and anaerobic bacteria have a broad antibacterial spectrum and strong bactericidal effect. Cefpirome has been successfully used in hospital and community-acquired severe lower respiratory tract infections; infections in leukopenia patients; severe infections in intensive care patients; sepsis / bacteremia; skin and soft tissue infections; complicated upper and lower urinary tract infections ; Treatment of meningitis, etc. Cefpirome sulfate can be well absorbed in the stomach, so cefpirome is usually made into cefpirome sulfate, the chemical name is 1-[[(6R,7R)-7-[(2Z)-( 2-aminothiazol-4-yl)(methoxyimino)acetamido]-2-carboxy-8-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/46C07D501/04
CPCC07D501/04C07D501/46
Inventor 刘占滨王喜军王硕冰高晶
Owner HARBIN PHARMA GRP CO LTD GENERAL PHARMA FACTORY
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