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Compound with liver-protecting activity

A compound and drug technology, applied in the field of compounds with hepatoprotective activity, can solve problems such as difficult to remove viruses, liver tissue damage, abnormal liver function, etc.

Active Publication Date: 2012-05-30
弘和制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, α-interferon and lamivudine are internationally recognized anti-hepatitis B virus drugs with good curative effect, but more than half of the patients do not heal for a long time after treatment, and immunomodulatory drugs are also difficult to clear the virus, resulting in the virus in the liver cells. Long-term replication activity, persistent damage to liver tissue, persistent abnormal liver function

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13

[0146] Example 13 Preparation of β-hydroxy-9-fluoro-11-oxo-18β, 20β-oleanane-12-enoic acid

[0147] 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%.

[0148] Step 2: Add 4.0 g (7.4 mmol) of 3β-acetoxy-11-oxid...

Embodiment 2

[0150] Example 2 Preparation of 3β-hydroxy-9-chloro-11-oxo-18β, 20β-oleanane-12-enoic acid

[0151] Step 1: Same as Step 1 in Example 1.

[0152] 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 solid was precipi...

Embodiment 3

[0154] Example 3 3-(β-2-O-β-D-glucopyranuronyl-α-D-glucopyranuronic acid)-9-fluoro-11-oxo Preparation of -18β, 20β-oleanane-12-enoic acid

[0155]Referring to the preparation method in Example 1, 3β-hydroxy-11-oxidized-18β,20β-oleanane-12-enoic acid was replaced with 3-(β-2-O-β-D-glucopyranoside Aldo-α-D-glucopyranurosidic acid)-11-oxo-18β, 20β-oleanane-12-enoic acid, yielding 3-(β-2-O-β-D- Glucopyranurosidyl-α-D-glucopyranuronic acid)-9-fluoro-11-oxo-18β, 20β-oleanane-12-enoic acid 2.8g, yield: 55.1% .

[0156] Elemental analysis (C 42 h 61 FO 16 ): C: 59.85%, H: 7.42%, F: 2.15% (theoretical: C: 59.99%, H: 7.31%, F: 2.26%)

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Abstract

The invention pertains to the technical field of medicine, relating to new compounds which have hepatoprotective activity or stereoisomer and salt thereof, the preparation methods of the compounds or the stereoisomer thereof, medical compositions 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 medicine to cure and / or prevent hepatopathy and inflammatorydisease. The compounds or the stereoisomer and salt thereof of the invention have prominent functions of resisting acute and chronic hepatic injury and good function of antivirus at the same time, as well as prominent anti-inflammatory activity.

Description

1. Technical field [0001] The present invention relates to novel compounds having hepatoprotective activity or their stereoisomers and salts thereof, processes for the preparation of these compounds or their stereoisomers, and compounds containing these compounds or their stereoisomers and their salts as essential active ingredients The pharmaceutical composition and the application of these compounds or their stereoisomers and their salts in the preparation of medicines for treating and / or preventing liver diseases and inflammatory 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 mill...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61K31/704A61P29/00A61P1/16A61P31/12
Inventor 黄振华
Owner 弘和制药有限公司
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