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Fenofibric urethan, preparation method and application thereof

A technology of amino acid ethyl ester salt and fenofibric acid, which is applied in the field of medicine, can solve the problems of affecting drug efficacy and poor water solubility, and achieve the effects of small side effects, high bioavailability, and good water solubility

Active Publication Date: 2012-10-31
TETRANOV PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Fenofibrate products currently on the market are packaged in powder form in capsules or made into tablets, but their poor water solubility affects their efficacy in the organism

Method used

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  • Fenofibric urethan, preparation method and application thereof
  • Fenofibric urethan, preparation method and application thereof
  • Fenofibric urethan, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] The fenofibric acid amino acid ethyl ester salt provided in this embodiment is:

[0022]

[0023] The preparation method is as follows: add 0.8g fenofibrate acid (2.5mmol) into 20ml ethyl acetate, stir at room temperature, add 5ml ethyl acetate solution containing 0.38g L-valine ethyl ester (2.6mmol), Wash with 3ml of ethyl acetate and add to the reaction system, the reaction system gradually becomes clear, and then a white precipitate gradually precipitates, the reaction system is heated to 50°C and kept for 20min, adding diethyl ether dropwise to make the reaction system clear, and slowly lowered to room temperature, about It takes 1.5 hours, and it is stirred at room temperature for 1 hour, filtered, the filter cake is washed with ether, and dried to obtain 0.35 g of a white solid, with a yield of 29%. The solubility of this compound in 1ml of pure water is about 3mg, which is slightly soluble. The nuclear magnetic analysis data of this compound are as follows: ...

Embodiment 2

[0025] The fenofibric acid amino acid ethyl ester salt provided in this embodiment is:

[0026]

[0027] Its preparation method is: add 0.9g fenofibric acid (2.8mmol) into 20ml ethyl acetate, under stirring at room temperature, add 5ml of ethyl acetate solution containing 0.34g L-alanine ethyl ester (2.9mmol), Wash with 3ml of ethyl acetate and add to the reaction system, the reaction system gradually becomes clear, and then a white precipitate gradually precipitates, the reaction system is heated to 50°C and kept for 20min, adding diethyl ether dropwise to make the reaction system clear, and slowly lowered to room temperature, about 1.5 hours, and stirred at room temperature for 1 hour, filtered, the filter cake was washed with ether, and dried to obtain 0.50 g of white solid, yield 40%. The solubility of this compound in 1ml of pure water is greater than 100mg, which is easily soluble. The nuclear magnetic analysis data of this compound are as follows: 1 H-NMR (D 2 O):...

Embodiment 3

[0029] The fenofibric acid amino acid ethyl ester salt provided in this embodiment is:

[0030]

[0031] Its preparation method is: add 0.9g fenofibric acid (2.8mmol) into 20ml ethyl acetate, under normal temperature stirring, add 5ml ethyl acetate solution containing 0.30g glycine ethyl ester (2.8mmol), and add 3ml ethyl acetate After washing the ester, add the reaction system, the reaction system gradually becomes clear, and then gradually precipitates a white precipitate, the reaction system is heated to 50 degrees and kept for 20 minutes, and diethyl ether is added dropwise to make the reaction system clear, slowly lowered to room temperature, about 1.5 hours, and Stir at room temperature for 1 hour, filter, wash the filter cake with ether, and dry to obtain 0.52 g of white solid, yield 43%. The solubility of this compound in 1ml of pure water is greater than 100mg, which is easily soluble. The nuclear magnetic analysis data of this compound are as follows: 1 H-NMR (D...

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Abstract

The invention relates to the technical field of medicines, particularly discloses fenofibric urethan, and meanwhile relates to a preparation method and application of fenofibric urethan. The fenofibric urethan is prepared by the reaction between fenofibric acid and urethan. The preparation method comprises the steps of adding fenofibric acid and urethan into a solvent, then reacting at room temperature until white precipitate is dissolved out, then heating to 45 DEG C-60 DEG C, keeping the temperature and reacting for 15-30min, dropwise adding diethyl ether into a reaction system until the reaction system is clear, then cooling to the room temperature, continuously reacting for 50-100min, filtering, washing a filter cake with diethyl ether, and drying to obtain fenofibric urethan. The fenofibric urethan provided by the invention can be used for effectively treating hyperlipidemia, fatty liver, hyperlipidemia and hyperglycemia disease and is good in water solubility, high in bioavailability and small in side effect.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a fenofibric acid amino acid ethyl ester salt, and also relates to a preparation method and application thereof. Background technique [0002] Hyperlipidemia is a type of disease that seriously threatens human health, including high cholesterol, high triglycerides, high low-density lipoprotein, etc. These three diseases cause a series of common clinical diseases, such as coronary heart disease, angina pectoris, myocardial infarction Wait. Hyperlipidemia is a common and frequently-occurring disease. With the aging population in China, hyperlipidemia will increase year by year. [0003] Fenofibrate tablets have been recorded in the Chinese Pharmacopoeia and are currently the drug of choice for the treatment of hyperlipidemia. Fenofibrate drugs can effectively reduce low-density lipoprotein and ultra-low-density lipoprotein levels, increase high-density lipoprotein levels, and re...

Claims

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Application Information

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IPC IPC(8): C07C59/90C07C51/41C07C229/08C07C229/22C07C229/26C07C227/18A61K31/205A61P3/06A61P3/10
Inventor 吴豫生牛成山邹大鹏李敬亚郭瑞云
Owner TETRANOV PHARMA CO LTD
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