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Cefminox sodium compound of new route

A technology of cefminox sodium and its compound, which is applied in the field of drug synthesis, can solve the problems of large related impurities, small toxic and side effects, and large drug toxic and side effects, and achieve the effect of improving yield and purity

Inactive Publication Date: 2011-02-02
HAINAN LINGKANG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] At present, the raw materials of cefminox sodium have always had the problem of low purity and large related impurities. my country's pharmaceutical research and development institutions have not made breakthroughs in this regard, resulting in relatively large toxic and side effects of clinically applied drugs. The production method of the small cefminox sodium compound has become a new hot spot in the current medical research

Method used

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  • Cefminox sodium compound of new route
  • Cefminox sodium compound of new route
  • Cefminox sodium compound of new route

Examples

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Effect test

Embodiment 1

[0030] Example 1 Synthesis of 7β-bromoacetamido-7a-methoxy-3-(1-methyl-1H-tetrazolium-5-thiomethyl)-3-cephem-4-carboxylic acid

[0031]262 grams (0.5mol) of 7-MAC were dissolved in a solvent of 2 liters of acetone, and the reaction solution was cooled to 10°C, while 101 grams (0.5mol) of bromoacetyl bromide was dissolved in 800ml of acetone solution and 70ml of triethylamine. Add 800ml of acetone solution to the above reaction solution dropwise at the same time to keep the pH of the reaction system = 8. After the addition, keep the reaction at 10°C for 1 hour. This reaction is distilled off under reduced pressure at no more than 25°C. solvent, then the residue was added to 3 liters of ethyl acetate and stirred, then washed with 0.1mol / L hydrochloric acid, water, and 5% aqueous solution of sodium bicarbonate, dried with anhydrous sodium sulfate, filtered, and decompressed Concentrate to give 7β-bromoacetamido-7a-methoxyl group-3-(1-methyl-1H-tetrazolium-5-thiomethyl)-3-cephem-4...

Embodiment 2

[0032] The synthesis of embodiment 2 cefminox sodium

[0033] 200 grams (0.42mol) of 7β-bromoacetamido-7a-methoxyl group-3-(1-methyl-1H-tetrazolium-5-thiomethyl)-3-cephem- 4-Carboxylic acid is suspended in water, adjust the pH=7.8 of reaction system with 10% sodium bicarbonate, add 5 grams of sodium iodide and 51 grams (0.42mol) of D-cysteine ​​hydrochloride to this reaction solution , adjust the pH of the reaction system to 7.6 with 10% sodium bicarbonate, while heating, make the reaction react at 30°C for 1.5 hours, cool to room temperature, add 2L isopropanol, precipitate crystals, filter, and freeze-dry to obtain 193 grams of product , the yield was 85%; the purity detected by HPLC method was 99.8%.

[0034] Elemental Analysis C 16 h 20 N 7 NaO 7 S 3

[0035] Theoretical value C: 35.48%, H: 3.72%, N: 18.10%, O: 20.68%, S: 17.75%,

[0036] Experimental values ​​C: 35.52%, H: 4.69%, N: 18.11%, O: 20.74%, S: 17.72%.

[0037] Through the chromatographic control test c...

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Abstract

The invention provides a cefminox sodium compound of a new route, in particular a method for producing the cefminox sodium compound. The method comprises a step of generating cefminox sodium through the reaction between 7beta-bromoacetamido-7a-methoxyl-3-(1-methyl-1H-tetrazole-5-S-methyl)-3-cephem-4-carboxylic acid and D-cysteine hydrochloride, and is characterized in that: the reaction conditionof the step is that the reaction is performed in aqueous solution, sodium iodide is used as a catalyst, the pH value of the reaction system is between 7.5 and 8.0, and the reaction temperature is kept at 30+ / -5 DEG C. Compared with the method for producing the cefminox sodium compound in the prior art, the method of the invention for producing the cefminox sodium compound greatly improves the product yield and the purity, and solves the problem that a cefminox sodium bulk drug always has a low purity in the prior art.

Description

technical field [0001] The invention relates to a production method of cephalosporin compounds, in particular to a production method of a new route of cefminox sodium compound, which belongs to the technical field of drug synthesis. Background technique [0002] Cefminox sodium, its chemical name is: (6R, 7S)-7-[(S)-2-(2-amino-2-carboxyethylmercapto)acetamido]-7-methoxy-3-[ [(1-Methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2 -Carboxylic acid sodium salt, molecular formula: C 16 h 20 N 7 NaO 7 S 3 , molecular weight: 541.56, structural formula: [0003] [0004] It is a third-generation cephalosporin antibiotic, which has good antibacterial effect on Gram-negative and positive bacteria, especially Escherichia coli, Klebsiella, Haemophilus influenzae, Proteus and Bacteroides fragilis Strong antibacterial effect. Its mechanism of action is that it has a strong affinity for the penicillin-binding protein at the usual site of action of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/36C07D501/04C07D501/12B01J27/138A61P31/04
Inventor 邱民
Owner HAINAN LINGKANG PHARMA CO LTD
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