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Carboxylic acid penicillin amine salt and application thereof in preparing high-purification sodium oxacillin salt

The technology of penicillin carboxylate and sodium salt is applied in the application field of preparing high-purity penicillin sodium salt.

Active Publication Date: 2012-05-02
QILU PHARMA HAINAN +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has the following disadvantages: 1) using a mixed solvent, the resulting product has no crystal form, high color grade, poor stability, and the product purity is only about 95%; 2) the yield of preparing sodium salt is only about 60%
This process has quality problems such as long production steps, low yield, and high product color grade.
[0017] The method for preparing penicillin carboxylate sodium salt in the above documents is not only limited in production scale, but also the obtained penicillin carboxylate sodium salt has high color grade, low specific rotation and poor purity, which cannot meet the requirements of the European Pharmacopoeia

Method used

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  • Carboxylic acid penicillin amine salt and application thereof in preparing high-purification sodium oxacillin salt
  • Carboxylic acid penicillin amine salt and application thereof in preparing high-purification sodium oxacillin salt
  • Carboxylic acid penicillin amine salt and application thereof in preparing high-purification sodium oxacillin salt

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Experimental program
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Effect test

Embodiment 1

[0064] The preparation of embodiment 1 ticarcillin dibenzylethylenediamine salt

[0065] Dissolve 21 g (0.05 mol) of ticarcillin sodium salt in 190 ml of water, add 200 ml of acetone to dilute, and filter after the solid is completely dissolved. Under rapid stirring of the obtained filtrate, N,N-dibenzylethylenediaminediacetic acid solution (18g (0.05mol) N,N-dibenzylethylenediaminediacetic acid dissolved in 150ml water) was added. A white crystalline solid precipitated out. After stirring for 1 hour, it was filtered and washed with water, and the obtained solid of ticarcillin dibenzylethylenediamine salt was dried at 35°C for 24 hours to obtain a solid weight of 30 g. Yield 86.9%. mp226~230°C (decomposition). High pressure liquid phase (HPLC) detection purity is 99.5% ( figure 2 ).

[0066] 1 HNMR analysis proves that the molar ratio of dibenzylethylenediamine and ticarcillin in the obtained ticarcillin dibenzylethylenediamine salt compound is dibenzylethylenediamine: ...

Embodiment 2

[0068] The preparation of embodiment 2 ticarcillin dibenzylethylenediamine salt

[0069] 4.2 g (0.01 mol) of ticarcillin sodium salt was dissolved in 40 ml of water, and a solution of 3.6 g of N,N-dibenzylethylenediamine diacetic acid and 40 ml of water was added to the feed solution. The ticarcillin benzylethylenediamine salt was precipitated immediately. After stirring for 2 hours, it was filtered, washed with water, and dried under vacuum at 35°C for 24 hours. 6 g of ticarcillin dibenzylethylenediamine salt was obtained with a yield of 79.5%. mp225~228°C, its purity is 99.7% by HPLC. Structure is identical with embodiment 1.

Embodiment 3

[0070] The preparation of embodiment 3 ticarcillin dibenzylethylenediamine salt

[0071] Dissolve 84 g (0.2 mol) of ticarcillin sodium in 420 ml of water, stir at room temperature until dissolved and filter. 61.5 g (0.2 mol) of N, N-dibenzylethylenediamine dihydrochloride was dissolved in 720 ml of water, and added to the ticarcillin sodium solution under rapid stirring. After adding, add 780ml acetone in feed liquid. Stir for 30 minutes, filter, wash with water, and vacuum-dry at 35° C. for 48 hours to obtain 130 g of ticarcillin dibenzylethylenediamine salt. Yield 97%. mp226~228°C, its purity is 99.2% by HPLC. Structure is identical with embodiment 1.

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Abstract

The invention relates to a carboxylic acid penicillin dibenzyl (substituting benzyl) ethylenediamine salt compound and an application thereof in preparing a high-purification sodium oxacillin salt. The carboxylic acid penicillin dibenzyl (substituting benzyl) ethylenediamine salt compound has a structure as the formula II, and carboxylic acid penicillin comprises ticacillin, carbenicillin and thelike, wherein R is thiofuran-3-group or phenyl; R1, R2 and R3 are respectively independent H, alkyls of C1-C5, halogens and nitryl; and substituent groups of the substituted alkyl are selected from the halogens and alkoxy groups of C1-C5.

Description

technical field [0001] The invention relates to a penicillin carboxylate dibenzyl (substituted benzyl) ethylenediamine salt compound and the application of the compound in the preparation of high-purity penicillin sodium salt. Background technique [0002] In the classification of penicillins, ticarcillin and carbenicillin are broad-spectrum semi-synthetic penicillin antibiotics, containing two carboxyl groups in the molecular structure, belonging to carboxylic acid penicillins, as shown in formula I, [0003] [0004] Among them, R is thiophen-3-yl or phenyl , M1 and M2 can be the same or different groups, such as sodium ions, potassium ions, amino groups, or appropriate amino groups, etc. [0005] Ticarcillin is a new thienyl carboxypenicillin developed by Beauchamp, which affects the synthesis of bacterial cell walls by interfering with mucopeptide cross-linking, resulting in defective or weak cell walls, deformed bacteria, and rapid dissolution and death. So as t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D499/72
Inventor 王树鹏于志海董廷华
Owner QILU PHARMA HAINAN
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