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Method of making cefquinome particles

A technology of cefquinome and splequinme, which is applied in the field of production of cefquinome acid addition salt granules, and can solve the problems of reducing particle size and the like

Active Publication Date: 2012-05-23
INTERVET INT BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Currently, the above sterile cefquinome sulfate granules prepared according to EP280157 or US2006 / 0100424 are too coarse and must be reduced in size by high energy particle size reduction methods, typically by grinding or micronization

Method used

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  • Method of making cefquinome particles
  • Method of making cefquinome particles
  • Method of making cefquinome particles

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Suspend 250.3 g of cefquinome sulfate in 740 ml of water at a temperature below 10 °C, then add 150 ml of 16.3% NaOH, followed by 1020 ml of acetone to precipitate sodium sulfate (Na 2 SO 4 ). After filtering and washing the salt with 375 ml of a mixture of acetone / water=1.27 / 1, the combined liquid was decolorized by treatment with 21 g of charcoal. After washing the charcoal with 150 ml of acetone / water=2 / 1, the combined liquid mixture was heated to 19° C., and then 388 ml of 15.1% sulfuric acid were added within 5 minutes. Stirring of the reaction mixture was continued at 19-21 °C for 35 min, then 1200 ml of acetone were added. With stirring, the suspension was poured into 12400 ml of acetone. After filtration and washing twice with 2500 ml of acetone, the precipitate was dried overnight at 32°C to yield 225 g of material for the preparation of ethyl oleate formulations A, B or C. The material was sampled for particle size distribution (PSD) measurements after add...

Embodiment 2

[0062] Corresponding to the method described in Example 1, 1200ml of water and 500g of cefquinome sulfate were reacted with 350g of 16.3% NaOH and 1325ml of acetone at 5°C. Both the salt and 15 g of charcoal were washed with 300 ml of acetone / water=3 / 1 each, followed by an additional charcoal wash with 215 ml of acetone / water=3.3 / 1, resulting in 3472 g of combined liquid, which was Used as stock solution. This stock solution was divided into three equal portions and used in Examples 2-1, 2-2 and 2-3.

Embodiment 2-1

[0064] A portion of 1158 g of the stock solution was heated to 18°C. 334 ml of acetone were added, followed by 286 g of a 15.1% dose of sulfuric acid within 5 minutes. The reaction mixture was stirred and then diluted with 800 ml of acetone with continuous stirring. The material was sampled for particle size distribution (PSD) measurements after addition of sulfuric acid and immediately before addition of acetone. Ultrasound is applied for 60 seconds.

[0065] PSD: D(100)=104.71 μm; D(90)=36.24 μm; D(50)=9.67 μm.

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Abstract

Disclosed is a process for the production of particles of a cefquinome acid addition salt, preferably cefquinome sulfate particles, by precipitation of cefquinome acid addition salt, preferably the sulfate, from a cefquinome betaine solution, wherein acid, preferably sulfuric acid, is added to the betaine solution. According to the invention the acid, preferably sulfuric acid, is added quickly in a single shot, in a molar excess of 40% to less than 100%. As a result, particles are formed that comprise agglomerates of microscale primary crystalline particles. This enables providing particles of cefquinome acid addition salt, preferably cefquinome sulfate, in particle sizes commensurate with micronized material, but with improved stability.

Description

field of invention [0001] The present invention relates to the production of granules of the acid addition salt of cefquinome. In particular, the present invention relates to a method of producing cefquinome sulfate crystals with a desired particle size range without high energy particle size reduction, such as milling or micronization. Background of the invention [0002] Cefquinome (cefquinome) is an antibiotic for humans and animals, especially for the treatment of bovine respiratory diseases, Pasteurella suis ( Pasteurella ) infection, and many other applications where high antimicrobial activity is expected. Cefquinome usually occurs as an acid addition salt, preferably sulfate. Cefquinome sulfate has the chemical structure of the following formula: [0003] [0004] The chemical name for this structure is 1-[[6R,7R)-7-[2-(2-Amino-4-thiazolyl)glyoxalamido]-2-carboxy-8-oxo-5-thio- 1-oxazolbicyclo[4.2.0]oct-2-en-3-yl]methyl]-5,6,7,8-tetrahydroquinoline Hydroxide,...

Claims

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Application Information

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IPC IPC(8): C07D501/46A61K31/545
CPCA61K31/545C07D501/46A61P31/04Y10T428/2982
Inventor H.P.尼德曼H.博特
Owner INTERVET INT BV
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