Preparation method for L-ornithine phenylacetate

A technology of ornithine phenylacetic acid and phenylacetic acid salt, applied in the field of medicine and chemical industry, can solve the problems of influence on the clinical effect of drugs, cumbersome research routes, large toxic and side effects, etc., and achieves low product toxic and side effects, high product purity, and low cost. Effect

Active Publication Date: 2013-03-27
NANJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The preparation method of L-ornithine phenylacetate reported abroad at present is: start with L-ornithine hydrochloride, first add silver benzoate to separate silver chloride and precipitate to obtain L-ornithine benzoic acid, then add Sodium phenylacetate produces L-orn

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Dissolve 16.8g of L-ornithine hydrochloride (containing 13.2g of free L-ornithine) in 500mL of water, adjust the pH to 2, and flow through the column filled with JK006 cation exchange resin. Rinse the column with 300mL of water to remove impurities such as chloride ions, then elute L-ornithine with 400mL of 2mol / L ammonia water, and concentrate the eluate to 200mL under reduced pressure to obtain free L-ornithine Aqueous solution (containing L-ornithine 0.1mol). Dissolve 6.8g of phenylacetic acid in 400mL of water at 75°C in a water bath, control the stirring rate at 80rpm in the aqueous solution of phenylacetic acid at 75°C, and add the above-mentioned free L-ornithine aqueous solution (L-ornithine) while stirring Acid to phenylacetic acid molar ratio is 2:1), after stirring for 20 minutes, evaporate and concentrate to 24mL, while stirring at room temperature, slowly add acetone 56mL, so that the volume ratio of acetone to the above mixed aqueous solution is 7:3, stir ...

Embodiment 2

[0025] Dissolve 20g of L-ornithine hydrochloride (containing 15.7g of free L-ornithine) in 500mL of water, adjust the pH to 2, and flow through the column filled with JK006 cation exchange resin. Rinse the column with 300mL of water to remove impurities such as chloride ions, then elute L-ornithine with 400mL of 2mol / L ammonia water, and concentrate the eluate to 200mL under reduced pressure to obtain free L-ornithine Aqueous solution (containing L-ornithine 0.119mol). Add 16.2g of phenylacetic acid (the molar ratio of L-ornithine to phenylacetic acid is 1:1) into 100mL of ethanol, and stir to dissolve. Add the ethanol solution of phenylacetic acid to the aqueous solution of L-ornithine at room temperature and control the stirring speed at 140 rpm, and stir for 20 min. Concentrate the stirred mixed solution to about 55mL under reduced pressure, and slowly add 220mL of isopropanol while stirring at room temperature, so that the volume ratio of isopropanol to the above mixed aq...

Embodiment 3

[0027] Dissolve 20g of L-ornithine nitrate (containing 13.5g of free L-ornithine) in 500mL of water, adjust the pH to 2, and flow through the column filled with JK006 type cation exchange resin to wash away impurities such as nitrate ions , and then 400 mL of 2 mol / L ammonia water was used to elute L-ornithine, and the eluate was concentrated to 200 mL under reduced pressure to obtain free L-ornithine aqueous solution (containing 0.102 mol of L-ornithine). Add 27.9g of phenylacetic acid (the molar ratio of L-ornithine to phenylacetic acid is 1:2) into 100mL of methanol, and stir to dissolve. The methanol solution of phenylacetic acid was added into the L-ornithine aqueous solution while stirring at room temperature under a controlled stirring rate of 200 rpm, and stirred for 20 min. Concentrate the stirred mixed solution to about 50ml under reduced pressure, and slowly add 250mL dimethyl sulfoxide while stirring at room temperature, so that the volume ratio of dimethyl sulfoxi...

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Abstract

The invention belongs to the field of pharmaceutical chemicals and relates to a preparation method for L-ornithine phenylacetate. The preparation method comprises the following steps of: mixing L-ornithine aqueous solution with phenylacetic acid solution; stirring and reacting the mixture; and crystallizing the obtained L-ornithine phenylacetate solution to separate out L-ornithine phenylacetate in the form of crystal. The preparation method is a one-step reaction, has a simple and gentle process, provides effective reference for the high purity and industrialization of the L-ornithine and phenylacetic acid, has a low toxic and side effect of the product, and ensures the safety of clinical medication. Compared with the prior art, the preparation method provided by the invention has low cost, high yield, and high product purity, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and relates to a preparation method of L-ornithine phenylacetate. Background technique [0002] Hepatic encephalopathy is a central nervous system dysfunction syndrome based on metabolic disorders caused by various subspecies of liver diseases clinically. It is caused by liver detoxification insufficiency and failure. Its clinical manifestations include disturbance of consciousness, abnormal behavior, coma, and elevated blood ammonia. When the liver fails, the ability of the liver to synthesize urea and remove ammonia decreases or even disappears, so that the ammonia from the intestinal tract directly enters the human circulation without detoxification by the liver, increasing blood ammonia, and high blood ammonia is toxic to the central nervous system Therefore, reducing blood ammonia is one of the effective measures for the treatment of hepatic encephalopathy. [0003] L-ornithin...

Claims

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Application Information

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IPC IPC(8): C07C229/26C07C227/18
Inventor 万红贵朱超
Owner NANJING UNIV OF TECH
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