L-ornithine glutamic acid double salt and preparation method and application thereof

A technology of ornithine glutamic acid and ornithine, which is applied in the fields of medicinal chemistry, biochemistry and medicine, can solve the problem of no L-ornithine glutamic acid double salt crystals, etc., to improve production efficiency and equipment utilization High efficiency, perfect crystal form, good stability and water solubility

Active Publication Date: 2014-06-04
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there is no L-ornithine glutamic acid double salt in the market for the treatment of hyperammonemia caused by acute and chronic liver diseases such as liver cirrhosis, fatty liver and hepatitis, especially for the treatment of central nervous system diseases caused by liver diseases. Relief of nervous system symptoms and rescue of hepatic coma, there is no method suitable for industrialized production of L-ornithine glutamic acid double salt crystals

Method used

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  • L-ornithine glutamic acid double salt and preparation method and application thereof
  • L-ornithine glutamic acid double salt and preparation method and application thereof
  • L-ornithine glutamic acid double salt and preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0041] First, the L-ornithine fermentation liquid (such as the fermentation liquid obtained according to the method of Example 1 or 2 in the document CN101955901A) is pretreated by membrane filtration, continuous separation, decolorization and other processes to obtain a free L-ornithine aqueous solution , and concentrate it to a concentration of 48g / L, take 100ml and pour it into a reaction crystallizer (such as Figure 5 shown, the same below), then put 5.31g of glutamic acid powder into it, stir at 25°C for 25 minutes to complete the reaction, add 0.1g of L-ornithine glutamic acid double salt seed crystal, stir for 30 minutes to grow the crystal, drop 150ml ethanol. Then lower the temperature to 10°C and keep the temperature constant for 0.5h. The obtained suspension was suction-filtered, washed, and dried for 5 hours at 20° C. under a vacuum of 0.08 MPa to obtain white columnar crystals of L-ornithine glutamic acid double salt. Its purity was determined to be 99.2%, and ...

Embodiment 2

[0043] L-ornithine hydrochloride was dechlorinated to obtain free L-ornithine aqueous solution, concentrated under reduced pressure until the concentration of free L-ornithine was 46g / L, took 100ml and poured it into a reaction crystallizer, and then put 5.14g into it Glutamic acid powder, stirred at 22°C for 30 minutes to complete the reaction, added 0.08 g of L-ornithine glutamic acid double salt seed crystal, stirred for 45 minutes, and added dropwise 200 ml of methanol. Then lower the temperature to 8°C and keep the temperature constant for 0.5h. The obtained suspension was suction-filtered, washed, and dried at 30° C. under a vacuum of 0.08 MPa for 4 hours to obtain white columnar crystals of L-ornithine glutamic acid double salt. Its purity was determined to be 99.3%, and the yield was 95.6%.

Embodiment 3

[0045] First, pretreat the L-ornithine fermentation liquid (such as the fermentation liquid obtained according to the method of Example 1 or 2 in the document CN101955901A) (the pretreatment method is the same as in Example 1) to obtain a free L-ornithine aqueous solution, and Concentrate it to a concentration of 46g / L, take 150ml and pour it into a reaction crystallizer, then put 7.1g of glutamic acid powder into it, stir at a constant temperature of 20°C for 20min to complete the reaction, add L-ornithine glutamic acid double salt crystal Seed 0.2g, stir and grow the crystal for 45min, and add 300ml of acetone dropwise. Then lower the temperature to 10°C and keep the temperature constant for 0.5h. The obtained suspension was suction-filtered, washed, and dried for 3 hours at 20° C. under a vacuum of 0.08 MPa to obtain white columnar crystals of L-ornithine glutamic acid double salt. Its purity was determined to be 99.4%, and the yield was 94.8%.

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Abstract

The invention belongs to the field of medicinal chemistry, biochemistry and medicines, and discloses an L-ornithine glutamic acid double salt and a preparation method and an application thereof. The structural formula of the L-ornithine glutamic acid double salt is shown as the formula (I) described in the specification. The L-ornithine glutamic acid double salt can be used for preparing a medicament for treating hyperammonemia caused by acute and chronic liver diseases, and particularly for medicaments for removing symptoms of the central nervous system caused by liver diseases and salvaging hepatic coma. The preparation method provided by the invention is simple, easy to operate, high in yield, low in cost, small in environmental pollution and convenient for industrialized production, and the double salt is perfect in crystalline form, greater in granularity and good in crystallization effect.

Description

technical field [0001] The invention belongs to the fields of medicinal chemistry, biochemistry and medicine, and relates to L-ornithine glutamic acid double salt and its preparation method and application. It specifically relates to the preparation method of L-ornithine glutamic acid double salt and its crystal, and the application of L-ornithine glutamic acid double salt in the preparation of drugs for the relief of central nervous system symptoms caused by liver diseases and rescue drugs for hepatic coma. application. Background technique [0002] The liver is the largest gland in the human body and has functions such as metabolism, blood coagulation, immunity, and bile production. Human liver function damage can lead to the disorder of ammonia metabolism in the body, resulting in a state of high blood ammonia in the body. Ammonia is a toxic substance to organisms, especially the brains of higher animals are extremely sensitive to ammonia. 1% ammonia in the blood can cau...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/24C07C229/26C07C227/18C07C227/42A61K31/198A61P1/16A61P3/00A61P25/00
Inventor 万红贵黄志旭石楠
Owner NANJING UNIV OF TECH
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