Synthesis of oleanolic acid saccinic acid monoester and its medicinal preparation for treating chronic and acute hepatitis

A technology of butyl butyl ester and medicine, which is applied in the modernization research of traditional Chinese medicine and the field of organic synthesis, and can solve problems such as unsatisfactory oral absorption, affecting dissolution and absorption, etc.

Inactive Publication Date: 2006-01-04
田振坤 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Oleanolic acid has antibacterial and anti-inflammatory properties, protects the liver and lowers enzymes, strengthens the heart and diuresis, enhances the immune function of the body, increases white blood cells, lowers blood lipids, lowers blood sugar and anti-cancer, etc. It has been used clinically for infectious acute jaundice Hepatitis and chronic persistent hepatitis can effectively improve clinical symptoms and signs, and become a more commonly used liver-protecting drug. However, due to the extremely difficult water-soluble characteristics of oleanolic acid, it affects its dissolution and absorption in the gastrointestinal tract. Therefore, oral absorption is not ideal. In order to increase its water solubility, enhance absorption, and improve bioavailability, we have modified the chemical structure of oleanolic acid, using pyridine as a catalyst to make the hydroxyl group at the 3-position of oleanolic acid and succinic anhydride The reaction is combined to form an ester, that is, oleanolic acid succinic acid monoester (referred to as butyl ester)

Method used

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  • Synthesis of oleanolic acid saccinic acid monoester and its medicinal preparation for treating chronic and acute hepatitis
  • Synthesis of oleanolic acid saccinic acid monoester and its medicinal preparation for treating chronic and acute hepatitis
  • Synthesis of oleanolic acid saccinic acid monoester and its medicinal preparation for treating chronic and acute hepatitis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Weigh 45.6g (0.1mol) of oleanolic acid, place it in a dry three-necked flask with a condenser, add 70g (0.7mol) of succinic anhydride, then add 180ml of pyridine, and react in a water bath at 100°C for 8 hours. , when the reaction solution is cooled, pour the reaction solution into large volume of cold water slowly, and keep stirring at the same time, so that the flocculent precipitate is gradually precipitated, filter the precipitate, wash repeatedly with distilled water until there is no pyridine smell, and dry the precipitate at 80°C , to obtain 53.5g of off-white powder, which is the crude product of oleanolic acid succinate, which can be recrystallized with ethanol to obtain the pure product of oleanolic acid succinic acid monoester.

[0026] 3. The pharmaceutical product of the present invention is used orally, and its dosage form can be capsules or tablets, etc. Relatively speaking, the preparation of capsules is more convenient in technology.

[0027] The follow...

Embodiment 2

[0028] Embodiment 2 capsules (Longya Gantai Capsules)

[0029] Prescription: 50g butyl ester, 22g starch, made into 1000 capsules

[0030] Preparation method: Mix the prescribed amount of butyl butyl ester and starch, pass through a No. 5 sieve, and pack into capsules.

[0031] 4. Zibutyl ester has the pharmacological effect of protecting the liver and reducing enzymes. The experiment and results are as follows:

[0032] 4.1 The effect of butyl ester on carbon tetrachloride-induced acute liver injury in mice

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Abstract

The present invention belongs to the field of Chinese medicine technology and organic synthesis technology. Oleanolic acid as one natural Chinese medicine component and succinic anhydride in the amount of 7 times produce esterification reaction under the catalysis of anhydrous pyridine in 4 times at 100 deg.c for 8 hr to produce succinyl oleanolic acid monoester with new chemical structure. After reaction, the product is water washed to eliminate residual succinic anhydride and pyridine and further purified through re-crystallization in anhydrous ethanol. The obtained new compound has molecular expression of C34H52O6, molecular weight of 556.77 and melting point of 256-258 deg c. By means of the structural modification, the present invention has raised water solubility and dispersivity and raised bioavailability. The product of the present invention is orally taken to treating acute and chronic liver damage, lower transaminase, reduce liver fibrosis and inhibit immunological liver pathologic changes.

Description

technical field [0001] This technical field belongs to the category of traditional Chinese medicine modernization research and organic synthesis technology. Background technique [0002] Oleanolic acid is a pentacyclic triterpenoid widely present in plants and Chinese herbal medicines, and is a very extensive secondary substance in plants. Oleanolic acid can be isolated from many plants such as Folium Folium, Ligustrum lucidum, Snow Gall, Aralia, Ginseng, Prunella, Forsythia, Hawthorn, Akebia, and Achyranthes bidentata. Oleanolic acid has antibacterial and anti-inflammatory properties, protects the liver and lowers enzymes, strengthens the heart and diuresis, enhances the immune function of the body, increases white blood cells, lowers blood lipids, lowers blood sugar and anti-cancer, etc. It has been used clinically for infectious acute jaundice Hepatitis and chronic persistent hepatitis can effectively improve clinical symptoms and signs, and become a more commonly used l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61K9/48A61P1/16A61P31/12
Inventor 田振坤
Owner 田振坤
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