Preparation method of mezlocillin sodium solvent crystal

A technology of mezlocillin sodium and mezlocillin acid, applied in the direction of effective components of heterocyclic compounds, organic chemistry, antibacterial drugs, etc., can solve the problems of low production efficiency, difficult recovery of reaction crystallization mixed solvent, low purity, etc. Achieve obvious implementation value and society, low production cost and high reaction yield

Active Publication Date: 2009-11-04
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In order to solve the shortcomings of low purity and low production efficiency of existing mezlocillin sodium products, and the use of reaction crystallization mixed solvents is difficul...

Method used

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  • Preparation method of mezlocillin sodium solvent crystal
  • Preparation method of mezlocillin sodium solvent crystal
  • Preparation method of mezlocillin sodium solvent crystal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The feed molar ratio is mezlocillin acid: sodium isooctanoate=1.0:1.2, the reaction solvent is acetone, and the poor solvent is isopropanol.

[0033] Weigh 53.9 g (0.1 mol) of mezlocillin acid, put it into a 250 ml beaker, add 118.6 g of acetone, and stir until completely dissolved. Then weigh 19.9 g (0.12 mol) of sodium isooctanoate, put it into a 2000 ml beaker, add 150.9 g of acetone, and stir. The acetone solution of mezlocillin acid was slowly added to the acetone solution of sodium isooctanoate at 20°C, and after 0.5 hours of reaction, 1500 g of isopropanol was slowly added. A white solid was continuously separated out, the addition of isopropanol was completed, and the mixture was stirred for 1 hour. After filtering, the filter cake was washed with 50 g×2 isopropanol, and dried with dry air at 60° C. for 6 hours to obtain 53.3 g of mezlocillin sodium white solid, with a yield of 95.0% and a content of 98.0% (HPLC). The acetone and isopropanol in the filtrate are sepa...

Embodiment 2

[0035] The feed molar ratio was changed to 1.0:2.0 of mezlocillin acid: sodium isooctanoate, the reaction solvent was acetone, and the poor solvent was isopropanol, and the dosage was 100 times the mass of mezlocillin acid. The actual dosage is 53.9 grams (0.1 mol) of mezlocillin acid, dissolved in 432 grams of acetone, 33.2 grams (0.2 mol) of sodium isooctanoate dissolved in 265 grams of acetone, and 5390 grams of isopropanol. The preparation steps under other conditions are the same as those in the example 1. Obtained 54.0 g of white solid of mezlocillin sodium, with a yield of 96.2% and a content of 98.1% (HPLC).

Embodiment 3

[0037] The feed molar ratio is mezlocillin acid: ethyl acetoacetate sodium 1.0:1.2, the reaction solvent is acetone, the poor solvent is isopropanol, and the dosage is 60 times the mass of mezlocillin acid. The actual dosage is 53.9 grams (0.1 mol) of mezlocillin acid, dissolved in 432 grams of acetone, 18.2 grams (0.12 mol) of ethyl acetoacetate dissolved in 146 grams of acetone, and 3234 grams of isopropanol. The preparation steps under other conditions are the same. Example 1. 51.2 g of mezlocillin sodium white solid was obtained, with a yield of 91.3% and a content of 97.4% (HPLC).

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Abstract

The invention discloses a preparation method of mezlocillin sodium solvent crystal, comprising the steps of (1) dissolving crude mezlocillin acid in a reaction solvent A to obtain solution A; (2) dissolving organic salt forming agent in a reaction solvent B to obtain solution B; (3) after adding the solution A into the solution B for sufficient reaction, slowly adding a poor solvent, separating out sodium solvent crystal, filtering, obtain filtrate and filter mass, drying the filter mass; the organic salt forming agent is sodium iso-octoate, ethyl acetoacetate or 2-ethyl sodium hexanoate; the reaction solvent A or B is independently acetone or ethyl acetate; the poor solvent is methanol, ethanol, propanol, isopropanol, aether, isopropyl ether, tetrahydrofuran, ethyl formate orbutyl acetate. The method is simple to operate, and has high stability, large yield, excellent product quality and few impurity contents; the reaction solvents and crystallizing solvent can be recycled, thus having low production cost, high reaction yield, excellent implementing value, and social and economic benefits.

Description

(1) Technical field [0001] The invention relates to a solvent crystal preparation method of the third generation semi-synthetic penicillin and mezlocillin sodium. (2) Background technology [0002] Mezlocillin sodium is a third-generation semi-synthetic penicillin antibacterial substance with a broad antibacterial spectrum and strong antibacterial activity. It has been included in the National Essential Drug List. Its chemical name is: (2S, 5R, 6R)-3,3-dimethyl-6-[(R)-2-{3-(methylsulfonyl-2-oxo-1-imidazolidine carboxamide) -2-Phenylacetamido}-7-oxo-4-thia-1-azabicyclo[3,2,0]heptane-2-sodium formate, the chemical structure is shown in the following formula: [0003] [0004] At present, there are mainly the following methods for the preparation of mezlocillin sodium: [0005] 1. Freeze drying method [0006] The freeze-drying method is to put the aqueous solution of mezlocillin acid and sodium alkaline compounds (such as sodium carbonate, sodium bicarbonate, etc.) directly into ...

Claims

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Application Information

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IPC IPC(8): C07D499/68C07D499/16A61K31/431A61P31/04
Inventor 李永曙谭成侠
Owner ZHEJIANG UNIV OF TECH
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