Alkali metal salt compound of celastrol and preparation method thereof

A technology of celandine and alkali metal salts, which is applied in the fields of steroids, chemical recovery, organic chemistry, etc., can solve the problems of instability, weak carboxyl acidity, and inability to use the human body, etc., and achieves the advantages of convenient operation and reduced packaging conditions Requirements, the effect of reducing production costs

Inactive Publication Date: 2009-01-21
SHANGHAI QICHENG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This solvent is not for use in humans, only in animal studies
[0006] Preparing water-soluble salts is a conventional method to increase the solubility of organic acids in water, but ceredictine belongs to triterpenoid fat-soluble compounds, and the carboxyl group in the structure is weakly acidic and has a large steric hindrance; at the same time, the carbonyl α-position in the structure Hydroxyl, in the conjugated unsaturated ketone system, is very active, not only sensitive to acid, but also very unstable to alkali, and ordinary acid-base neutralization reaction cannot produce sherendin salt

Method used

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  • Alkali metal salt compound of celastrol and preparation method thereof
  • Alkali metal salt compound of celastrol and preparation method thereof
  • Alkali metal salt compound of celastrol and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Preparation of sherendin sodium salt compound.

[0025] After dissolving 101.5 mg of cerulein in 2-3 ml of ethanol, add 1 ml of aqueous sodium bicarbonate solution (containing 19.9 mg of sodium bicarbonate), mix well, add a small amount of water dropwise to clarify the solution, and stir at room temperature for 4 hours. Concentrate under reduced pressure at 40°C to dryness, add 4ml of absolute ethanol to the residue to dissolve, filter, add ethyl acetate dropwise to the filtrate until cloudy, refrigerate at 5°C for 12 hours, a dark red precipitate precipitates, filter it out, and dry under reduced pressure at 40°C for 3 hours, the product 92mg was obtained. Yield: 75.8%.

[0026] Analysis results:

[0027] The H-NMR spectrum data of ceherin sodium salt: 1 H NMR (DMSO, 300M), δ7.052 (2H, d, J=7.2Hz, H-6), 6.367 (1H, s, H-1), 6.315 (1H, d, J=7.2Hz, H- 7), 2.083 (3H, s, CH 3 -23), 1.362, 1.198, 1.016, 0.922, (each 3H, s, CH 3 -25,CH 3 -26,CH 3 -30,CH 3 ...

Embodiment 2

[0035] Example 2: Preparation of sherendin potassium salt compound.

[0036] After dissolving 100.9 mg of cerulein in 2-3 ml of methanol, add 1 ml of aqueous potassium bicarbonate solution (containing 23.5 mg of potassium bicarbonate), mix well, add a small amount of water dropwise to clarify the solution, and stir at room temperature for 4 hours. Concentrate to dryness under reduced pressure at 40°C, add 4ml of absolute ethanol to the residue to dissolve, filter, and concentrate the filtrate to dryness under reduced pressure at 35°C to obtain a dark red powder, dry under reduced pressure at 35°C for 3 hours to obtain 97mg of the product. Yield: 78.8%.

[0037] Analysis results:

[0038] The H-NMR spectrum data of ceherin potassium salt: 1H NMR (DMSO, 300M), δ7.053 (2H, d, J=7.2Hz, H-6), 6.373 (1H, s, H-1), 6.319 (1H, d, J=7.2Hz, H- 7), 2.085 (3H, s, CH 3 -23), 1.362, 1.194, 1.008, 0.872, (each 3H, s, CH 3 -25, CH3-26, CH 3 -30,CH 3 -28), 0.720 (3H, s, CH 3 -27).

[0...

Embodiment 3

[0040] Example 3: Preparation of ceherin sodium salt compound.

[0041] After dissolving 10.23g of shertenin in 200ml of methanol, add 100ml of aqueous sodium bicarbonate solution (containing 2.00g of sodium bicarbonate), mix well, add a small amount of water dropwise to clarify the solution, and stir at room temperature for 4 hours. Concentrate under reduced pressure at 40°C to dryness, add 200ml of isopropanol to the residue to dissolve, filter, add ethyl acetate dropwise to the filtrate until cloudy, refrigerate at 0°C for 12 hours, a deep red precipitate is obtained, filter it out, and dry under reduced pressure at 40°C After 5 hours, 10.52 g of the product was obtained. Yield: 86%.

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Abstract

The present invention discloses a water-soluble celastrin alkali metal salt compound its preparation method. The constitutional formula is indicated as formula I, in which M+ is respectively Na+ and K+. The inventive method doesn't use toxic organic solvent, and low toxicity or nontoxic solvent are all recovered and utilized.The inventive celastrin alkali metal salt compound (I) can be made into pharmaceutically formulation, including injection, tablet, capsule, granula and liniment especially for preparing powder injection formulation.

Description

technical field [0001] The invention relates to a celandine alkali metal salt compound and a preparation method thereof. Background technique [0002] Celastrol, also known as tripterygium, is an anticancer active ingredient present in Euonymus plants Tripterygium wilfordii and Celastrol. Document 1: Pristimerin.Spectroscopic properties of the dienone-phenol-type rearrangement products and other derivatives [KojiNakanishi, Yoshikazu Takahashi, et al.J.Org.Chem., 1965(30), 1729] Mentioned, earlier than 1960, That is to say, it has been found that this type of compound has antitumor activity, the latest literature 2: Celastrol, a Triterpene Extracted from the Chinese Thunder of God Vine Is a Potent Proteasome Inhibitor and Suppresses Human Prostate Cancer Growth in Nude Mice [Huanjie Yang, Di Chen, et al. Cancer Research, 2006 (66), 4758] confirmed that cereli is an effective proteasome inhibitor by inhibiting proteasome activity and then inducing cancer cell apoptosis. . T...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00
CPCY02P20/582
Inventor 曾佳烽潘俊芳李宝莹朱勤
Owner SHANGHAI QICHENG PHARMA CO LTD
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