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Preparation of arginine acetylsalicylate

An aspirin arginine salt and aspirin technology are applied in the field of preparation of aspirin arginine salt, can solve the problems of unfavorable industrialized production, complicated operation process and high equipment requirements, achieve good water solubility, simple reaction conditions and wide application range Effect

Inactive Publication Date: 2009-07-22
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because arginine hydrochloride contains excessive chloride ions, patients are prone to hyperchloric acidosis, which limits its application in medicine.
[0004] So far, only one patent about the preparation of aspirin arginine salt has been found - US Patent Publication US 3487103, which proposes the method of using ion exchange resin to prepare aspirin arginine salt, but this method has a complicated operation process , high equipment requirements, large amount of solvent, and relatively low yield, which are not conducive to industrial production

Method used

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  • Preparation of arginine acetylsalicylate
  • Preparation of arginine acetylsalicylate
  • Preparation of arginine acetylsalicylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Dissolve 5 grams of aspirin in 30ml of 95% ethanol, suspend 4.85 grams of arginine in 15ml of 80% ethanol, add dropwise at a rate of 10mL / min, and add the aspirin solution dropwise to the essence at 60°C. In the amino acid suspension, after the dropwise addition, the arginine solid disappears, the reaction solution is clear, and cooled under stirring. After 10 minutes, the aspirin arginine salt precipitates, and the stirring is continued until about 30°C to stop. Place in the refrigerator overnight, filter with suction, collect the product, wash with 95% ethanol three times, each time the amount of 95% ethanol is 20 mL, and dry at 40°C. 7.6 g of product were obtained. Product yield calculated as aspirin: 77.2%, percent content: aspirin 53.58%, arginine 46.36%.

Embodiment 2

[0035] Dissolve 10 grams of aspirin in 45 ml of 95% ethanol, suspend 10.6 grams of arginine in 30 ml of 90% ethanol, add dropwise at a rate of 10 ml / min, add the aspirin solution dropwise to arginine at 63°C In the acid suspension, after the dropwise addition, the arginine solid disappears, the reaction solution is clear, and cooled under stirring. When the temperature drops to 42°C, aspirin arginine salt precipitates, continue to stir until about 30°C and stop. Place in a refrigerator at 0°C overnight, filter with suction, collect the product, wash with 95% ethanol three times, each 95% ethanol dosage is 30 mL, and dry at 40°C. 15.8 g of product were obtained. Product yield calculated as aspirin: 80.3%, percent content: aspirin 53.67%, arginine 46.13%.

[0036] Table 1 List of aspirin arginine salts prepared under different conditions

[0037]

[0038] * It is the product of free salicylic acid exceeding the standard

[0039] Table 1 is the aspirin arginine salt prepar...

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Abstract

The invention relates to a preparation method of aspirin arginine. The method is characterized in that: aspirin and arginine as reactants respectively dissolve in linear chain or branched aliphatic alcohol solvents with 1 to 4 carbon atoms, under two-phase stirring, the aspirin alcoholic solution is dripped into the arginine alcoholic suspension, at room temperature and under normal pressure, the reaction takes place to generate aspirin arginine crystals; the aspirin arginine is obtained through the filtration and drying of the crystals; and the molar ratio is as follows: aspirin: arginine is 1:1 to 1.1. The method has simple and feasible production technique, short flow, low cost, high yield and good product quality.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, and more specifically relates to a preparation method of aspirin arginine salt. Background technique [0002] Aspirin is an antipyretic, analgesic and anti-inflammatory drug commonly used in clinic. Due to its poor water solubility and strong irritation to the gastrointestinal mucosa after oral administration, it often causes adverse reactions such as nausea, vomiting, upper abdominal discomfort and anorexia, and can induce and aggravate gastric ulcer and cause gastric bleeding. For the above reasons, the application of aspirin has been greatly restricted. [0003] Arginine (Arginine) is a "semi-essential" amino acid for the human body. It has a low synthesis ability in the human body and needs to be partially supplemented from food, but it is an essential amino acid for maintaining the growth and development of infants. In the body, it is an intermediate metabolite of the ornithine cycle, wh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/157C07C279/14
Inventor 李有桂陈天云
Owner HEFEI UNIV OF TECH
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