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Compound used for viral infect

A compound and stereoisomer technology, applied in steroids, antiviral agents, digestive system, etc., can solve problems such as abnormal liver function, liver tissue damage, and difficulty in clearing viruses

Active Publication Date: 2008-06-04
吉林津升制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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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  • Compound used for viral infect
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0129] Example 1 Hydroxy-11′-oxo-18′β, 20′β-oleanane-12′-enoic acid-3′β-O-[2-[(adenine)-9-yl]B Oxygen]- Preparation of Methyl Phosphate Monoester

[0130] Suspend 27.3 g (0.1 mol) of 9-(phosphonomethoxy-ethyl) adenine in 100 mL of DMF, add 50 g of triethylamine, raise the temperature to 50°C and slowly add 3β-hydroxyl-11-oxygen in batches while stirring Dai-18β, 20β-oleanane-12-enoic acid 47.1g (0.1mol), stirred for 12h, the reaction solution was cooled, added 300ml of deionized water, after stirring, a solid precipitated, filtered, and the filter cake was washed with 200ml of ethyl acetate After dissolving, transfer it to a separatory funnel, wash with 20ml×3 water, then extract the organic layer with 1mol / l HCl50ml×3, combine the acidic water layer, and wash with saturated Na 2 CO 3 After adjusting the pH of the solution to 6, extract with 60ml × 3 ethyl acetate, combine the ethyl acetate layers and wash with saturated sodium chloride solution, dry the organic layer, f...

Embodiment 2

[0132] Example 2 11'-oxo-18'β, 20'β-oleanane-12'-enoic acid-3'β-O-[2-[(adenin)-9-yl]propoxy ]-Methylphosphonium Preparation of Acid Monoesters

[0133] Referring to the preparation method in Example 1, 9-(2-phosphonomethoxy-ethyl)adenine was replaced by 9-(2-phosphonomethoxy-propyl)adenine to obtain 11′-oxo Generation-18′β,20′β-Oleanane-12′-enoic acid-3′β-O-[2-[(Adenin)-9-yl]propoxy]-methylphosphonic acid monoester 34.9 g, yield: 47.1%.

[0134] Elemental analysis (C 39 h 58 N 5 o 7 P): C: 63.19%, H: 7.98%, N: 9.41%, P: 4.12% (theoretical: C: 63.31%, H: 7.90%, N: 9.47%, P: 4.19%).

Embodiment 3

[0135] Example 3 18'β, 20'β-Oleanane-12'-enoic acid-3'β-O-[2-[(Adenin)-9-yl]ethoxy]-methylphosphonic acid mono ester preparation of

[0136] Referring to the preparation method in Example 1, replace 3β-hydroxy-11-oxo-18β, 20β-oleanane-12-enoic acid with 3β-hydroxy-18β, 20β-oleanane-12-ene Acid to give 18′β, 20′β-oleanane-12′-enoic acid-3′β-O-[2-[(adenin)-9-yl]ethoxy]-methylphosphonic acid mono 32.2 g of ester, yield: 45.4%.

[0137] Elemental analysis (C 38 h 58 N 5 o 6 P): C: 64.02%, H: 8.28%, N: 9.81%, P: 4.30% (theoretical: C: 64.11%, H: 8.21%, N: 9.84%, P: 4.35%).

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Abstract

The invention pertains to the technical field of medicine, relating to new compounds, which have the activity of antivirus, etc., or stereoisomer and salt thereof, the preparation methods of the compounds or stereoisomer and salt thereof, medical compositions which comprise the compounds or stereoisomer and salt thereof as necessary active ingredients, and the application of the compounds or stereoisomer and salt thereof in the preparation of medicines to cure and / or prevent viral infection and hepatopathy. The compounds or stereoisomer thereof of the invention have prominent functions of antivirus, in particular to hepatitis B virus and human immunodeficiency virus, and have prominent activity to resist acute and chronic hepatic injury at the same time.

Description

1. Technical field [0001] The present invention relates to novel compounds or their stereoisomers and their salts having antiviral activity, etc., and methods for preparing these compounds or their stereoisomers, which contain 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 viral infections and liver diseases belong to the technical field of medicine. 2. Background technology [0002] Virus infection can cause various diseases and seriously endanger human health and life. According to incomplete statistics, about 60% of epidemic infectious diseases are caused by viruses. It has been found that there are more than 1,200 kinds of viruses that are pathogenic to humans, among which the AIDS (AIDS) and hepatitis B virus caused by the human immunodeficiency virus (HIV) di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/662A61P1/16A61P31/12
Inventor 黄振华
Owner 吉林津升制药有限公司
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