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Compound used for liver disease

A technology for compounds and stereoisomers, applied in the field of pharmaceutical compositions, can solve problems such as poor hydrophilicity and poor oral bioavailability

Inactive Publication Date: 2008-06-04
SHANDONG XUANZHU PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its poor hydrophilicity and poor oral bioavailability, it cannot meet the clinical needs

Method used

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  • Compound used for liver disease
  • Compound used for liver disease
  • Compound used for liver disease

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13

[0124] The preparation of embodiment 13-(2-mercapto-propionyl)-11-oxo-18β, 20β-oleanane-12-enoic acid

[0125] In a dry reaction flask, add 50ml of acetonitrile, 5g (10.6mmol) of 3β-hydroxy-11-oxidized-18β,20β-oleanane-12-enoic acid, and then add 5ml of triethylamine, stir to dissolve and heat up to reflux , and then drop 2-mercapto-propionyl chloride 1.9g (15mmol) / 20ml acetonitrile solution, continue to stir and reflux for 10h after the dropwise addition, recover the solvent, add an appropriate amount of ice water to the residue and extract it with ethyl acetate 50ml×2, organic The layer was dried, and the solvent was recovered to obtain 4.8 g of 3-(2-mercapto-propionyl)-11-oxo-18β,20β-oleanane-12-enoic acid, yield: 81.2%.

[0126] Elemental analysis (C 33 h 50 o 5 S):

[0127] C: 70.74%, H: 9.09%, S: 5.69%

[0128] Theoretical: C: 70.93%, H: 9.02%, S: 5.74%.

Embodiment 2

[0129] Example 2 Preparation of 3-(2-mercapto-propionyl)-9-fluoro-11-oxo-18β,20β-oleanane-12-enoic acid

[0130] Step 1: In a dry reaction flask, add 30ml each of acetic anhydride and pyridine, add 4.7g (10mmol) 3β-hydroxyl-11-oxidation-18β, 20β-oleanane-12-enoic acid after stirring, at 60 Stir the reaction at ℃ for 10 h, after the reaction is completed, pour the reaction solution into ice water under vigorous stirring, and a yellow solid precipitates, dry at 60 °C and then add it to the reaction flask, add 50 ml of absolute ethanol and 1 ml of concentrated sulfuric acid, heat and stir to reflux for 5 h, After the reaction is completed, the solvent is recovered, the residue is added with an appropriate amount of ice water and extracted with ethyl acetate 50ml×2, the organic layers are combined and dried, and the solvent is recovered to obtain 3β-acetoxy-11-oxidized-18β,20β-oleanane -12-enoic acid ethyl ester 4.1g, yield: 75.9%.

[0131] Step 2: Add 4.0 g (7.4 mmol) of 3β-ac...

Embodiment 3

[0136] Example 3 Preparation of 3-(2-mercapto-propionyl)-9-chloro-11-oxo-18β,20β-oleanane-12-enoic acid

[0137] Step 1: Same as Step 1 in Example 2.

[0138] Step 2: Add 4.0g (7.4mmol) of ethyl 3β-acetoxy-11-oxidation-18β,20β-oleanane-12-enoate and carbon tetrachloride to a dry reaction flask under a nitrogen atmosphere 50ml, 10mlSO 2 Cl 2 / carbon tetrachloride 50ml, heat up to 60°C and stir for 3h, evaporate the solvent under reduced pressure; after cooling down to room temperature, add 50ml of water, then extract with 30ml×3 ethyl acetate, combine the organic phases and wash with saturated sodium bicarbonate solution , dried and filtered, concentrated under reduced pressure, the residue was dissolved in 95% ethanol, 0.9g of sodium hydroxide was added, and after reflux and stirring for 1h, the solvent was recovered under reduced pressure at 50°C, the residue was added with 50ml of water, and the pH was adjusted to 4 with dilute hydrochloric acid. ~6, a light yellow soli...

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Abstract

The invention pertains to the technical field of medicine, and relates to a compound which is applied in hepatopathy, stereoisomer and salt thereof, shown in the formula as follows, the preparation methods of the compounds or the stereoisomer and salt thereof, medical combinations which comprise the compounds or the stereoisomer and salt thereof as necessary active ingredients, and the application of the compounds or the stereoisomer and salt thereof in the preparation of medicines to cure and / or prevent hepatopathy, wherein, R<1>, R<2>, R<3>, R<4>, R<5> are defined as the specification.

Description

1. Technical field [0001] The present invention relates to novel compounds having hepatoprotective activity, their stereoisomers and salts thereof, processes for the preparation of these compounds, their stereoisomers and their salts, containing these compounds or their stereoisomers and their salts as essential The pharmaceutical composition of active ingredients, and the application of these compounds or their stereoisomers and their salts in the preparation of medicines for treating and / or preventing liver diseases belong to the technical field of medicine. 2. Background technology [0002] According to the statistics of the World Health Organization, in 2000, about 350 million people in the world were chronic hepatitis patients or hepatitis B virus (HBV) carriers, and more than 1 million people died of diseases related to hepatitis, cirrhosis, and liver cancer every year. my country is a high-incidence area of ​​viral hepatitis. There are 120 million HBV carriers, accoun...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/56A61P1/16A61P31/12
Inventor 黄振华
Owner SHANDONG XUANZHU PHARMA TECH CO LTD
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