A kind of rosuvastatin amino acid salt and its preparation method and application

A technology of rosuvastatin and amino acid salt, which is applied in the field of cardiovascular medicine, can solve liver problems and other problems, and achieve the effects of improving water solubility, preferential price and increasing utilization rate

Active Publication Date: 2016-04-06
SHANGHAI KECHOW PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, long-term use of it can also cause liver problems

Method used

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  • A kind of rosuvastatin amino acid salt and its preparation method and application
  • A kind of rosuvastatin amino acid salt and its preparation method and application
  • A kind of rosuvastatin amino acid salt and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] A kind of rosuvastatin arginine salt, the structural formula after its salification is as follows:

[0078]

[0079] or

[0080]

[0081] or

[0082]

[0083] A preparation method of rosuvastatin arginine salt, the steps are as follows:

[0084] (1) Weigh 2g of rosuvastatin tert-butyl ester (3.46mmol), dissolve in a solvent of 20ml of methanol and 5ml of tetrahydrofuran, and stir to dissolve;

[0085] (2) Add 4ml of 1mol / L hydrochloric acid (4mmol) to the solution in step (1), stir at 30-35°C for 2h, and TLC detects that the reaction is complete;

[0086] (3) Add 1.4ml of 3mol / L sodium hydroxide (4.2mmol) to the solution in step (2), stir and react at room temperature for 1h, evaporate the solvent of the reaction solution to dryness; add water to it, and extract with methyl tert-butyl ether to remove impurities ;

[0087] (4) Adjust the aqueous phase in the solution in step (3) to neutral or weakly acidic with 2mol / L hydrochloric acid, extract with ethyl ac...

Embodiment 2

[0093] A kind of rosuvastatin lysine salt, the structural formula after its salification is as follows:

[0094]

[0095] or

[0096]

[0097] or

[0098]

[0099] A preparation method of rosuvastatin lysine salt, the steps are as follows:

[0100] (1) Weigh 2g of rosuvastatin tert-butyl ester (3.46mmol), dissolve in a solvent of 20ml of methanol and 5ml of tetrahydrofuran, and stir to dissolve;

[0101] (2) Add 4ml of 1mol / L hydrochloric acid (4mmol) to the solution in step (1), stir at 30-35°C for 2h, and TLC detects that the reaction is complete;

[0102] (3) Add 1.4ml of 3mol / L sodium hydroxide (4.2mmol) to the solution in step (2), stir and react at room temperature for 1h, evaporate the solvent of the reaction solution to dryness; add water to it, and extract with methyl tert-butyl ether to remove impurities ;

[0103] (4) Adjust the aqueous phase in the solution in step (3) to neutral or weakly acidic with 2mol / L hydrochloric acid, extract with ethyl acetat...

Embodiment 3

[0109] A kind of rosuvastatin histidine salt, the structural formula after its salification is as follows:

[0110]

[0111] or

[0112]

[0113] or

[0114]

[0115] A preparation method of rosuvastatin histidine salt, the steps are as follows:

[0116] (1) Weigh 2g of rosuvastatin tert-butyl ester (3.46mmol), dissolve it in a solvent of 20ml of methanol and 5ml of tetrahydrofuran, and stir to dissolve;

[0117] (2) Add 4ml of 1mol / L hydrochloric acid (4mmol) to the solution in step (1), stir at 30-35°C for 2h, and TLC detects that the reaction is complete;

[0118](3) Add 1.4ml of 3mol / L sodium hydroxide (4.2mmol) to the solution in step (2), stir and react at room temperature for 1h, evaporate the solvent of the reaction solution to dryness; add water to it, and extract with methyl tert-butyl ether to remove impurities ;

[0119] (4) Adjust the aqueous phase in the solution in step (3) to neutral or weakly acidic with 2mol / L hydrochloric acid, extract with ethy...

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PUM

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Abstract

The invention relates to a rosuvastatin amino acid salt as well as a preparation method of the rosuvastatin amino acid salt. Such a compound, namely, amino acid salt, is prepared through the reaction between rosuvastatin acid and basic amino acid. The preparation method comprises the following steps of: (1) weighing rosuvastatin acid, and dissolving into C1-C6 alcohol solvents, water or a halohydrocarbon solution to obtain a solution A; (2) weighing basic amino acid, and dissolving into C1-C6 alcohol solvents or water to obtain a solution B; (3) adding the solution B to the solution A, stirring and remaining overnight, cooling the reaction liquid to reach room temperature, and then vaporizing and eliminating the solvents; (4) adding methanol, separating and filtering to remove excessive basic amino acid; and (5) concentrating, refluxing, cooling, filtering and drying to obtain the amino acid salt of the rosuvastatin. The rosuvastatin amino acid salt prepared by the preparation method not only has the effect of treating high cholesterol blood lipid and combined hyperlipidemia, and also gains the function of amino acid, thus the salt effectively fills in gaps due to the known side effects of hurt of calcium salt, sylvite and sodium salt and the like to the liver.

Description

technical field [0001] The invention belongs to the field of cardiovascular disease medicine, and relates to rosuvastatin salt, in particular to rosuvastatin amino acid salt and its preparation method and application. Background technique [0002] Cardiovascular disease seriously endangers human health and affects the quality of life of human beings. Crestor, also known as Rosuvastatin, is a statin blood lipid regulating drug and belongs to HMG-CoA reductase inhibitor. The main one used is rosuvastatin calcium salt. [0003] Rosuvastatin calcium salt itself is inactive, and its main active ingredient is the hydrolyzate after oral absorption. It competitively inhibits the rate-limiting enzyme hydroxymethylglutaryl-CoA reductase in the process of cholesterol synthesis in vivo, thereby reducing the synthesis of cholesterol and increasing the synthesis of low-density lipoprotein receptors. Its main action site is in the liver. As a result, blood cholesterol and low-density lip...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/42C07C279/14C07C277/08C07C229/26C07C227/18C07D233/64A61P3/06A61P1/16A61P37/04A61P13/12
Inventor 田红旗程瑛
Owner SHANGHAI KECHOW PHARMA
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