Novel compound with antiviral activity

A compound, methyl technology, applied in the field of medicine, can solve the problems of narrow activity range, increased drug resistance, high price, etc.

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 the variability of influenza virus antigens and the multiplicity of acute respiratory virus infections, the vaccine is ineffective; interferon has limited its application due to reasons such as source, dosage, and side effects; antiviral chemotherapy drugs, such as nucleosides, Amantadines,

Method used

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  • Novel compound with antiviral activity
  • Novel compound with antiviral activity
  • Novel compound with antiviral activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0185] Example 1 6-bromo-4-dimethylaminomethyl-5-hydroxyl-1-methyl-2-(4-methyl-2-thiomethyl-5-carboxymethyl-thiazole)-1H- Preparation of ethyl indole-3-carboxylate hydrochloride

[0186] (1) 6-Bromo-5-hydroxy-1-methyl-2-(4-methyl-2-thiomethyl-5-carboxymethyl-thiazole)-1H-indole-3-carboxylic acid ethyl ester preparation of

[0187] In the dry reaction bottle, add methanol 300ml, potassium hydroxide 13g (0.23mol), after stirring and dissolving, add 27g (0.23mol) 4-methyl-2-thiomethyl-5-carboxymethyl-thiazole in batches, Stir at room temperature for 10 min. Then 90 g (0.23 mol) of ethyl 5-acetoxy-6-bromo-2-bromomethyl-1-methyl-1H-indole-3-carboxylate was added, stirred for 12 hours, and the reaction was completed. Pour the reaction solution into ice water under stirring, adjust the pH to about 2 with dilute hydrochloric acid, precipitate out, filter with suction, wash the filter cake with water and dry to obtain 74.6 g of light yellow solid, namely 6-bromo-5-hydroxy-1-methy...

Embodiment 2

[0193] Example 2 6-bromo-4-dimethylaminomethyl-5-hydroxy-1-methyl-2-(2-thiomethyl-thiazole)-1H-indole-3-carboxylic acid ethyl ester Preparation of hydrochloride

[0194] (1) Preparation of 6-bromo-5-hydroxyl-1-methyl-2-(2-thiomethyl-thiazole)-1H-indole-3-carboxylic acid ethyl ester

[0195] In the dry reaction bottle, add 300ml of methanol and 13g (0.23mol) of potassium hydroxide, stir and dissolve, add 27g (0.23mol) of 2-mercaptothiazole in batches, and stir at room temperature for 10min. Then 90 g (0.23 mol) of ethyl 5-acetoxy-6-bromo-2-bromomethyl-1-methyl-1H-indole-3-carboxylate was added, stirred for 12 hours, and the reaction was completed. Pour the reaction solution into ice water under stirring, adjust the pH to about 2 with dilute hydrochloric acid, precipitate out, filter with suction, wash the filter cake with water and dry to obtain 74.6 g of light yellow solid, namely 6-bromo-5-hydroxy-1-methyl Ethyl-2-(2-thiomethyl-thiazole)-1H-indole-3-carboxylate, yield: 7...

Embodiment 3

[0201] Example 3 6-bromo-4-dimethylaminomethyl-5-hydroxyl-1-methyl-2-(4-methyl-2-thiomethyl-thiazole)-1H-indole-3- Preparation of ethyl carboxylate hydrochloride

[0202] (1) Preparation of 6-bromo-5-hydroxyl-1-methyl-2-(4-methyl-2-thiomethyl-thiazole)-1H-indole-3-carboxylic acid ethyl ester

[0203] In a dry reaction flask, add 300ml of methanol and 13g (0.23mol) of potassium hydroxide, stir to dissolve, add 27g (0.23mol) of 4-methyl-2-thiomethyl-thiazole in batches, and stir at room temperature for 10min. Then 90 g (0.23 mol) of ethyl 5-acetoxy-6-bromo-2-bromomethyl-1-methyl-1H-indole-3-carboxylate was added, stirred for 12 hours, and the reaction was completed. Pour the reaction solution into ice water under stirring, adjust the pH to about 2 with dilute hydrochloric acid, precipitate out, filter with suction, wash the filter cake with water and dry to obtain 74.6 g of light yellow solid, namely 6-bromo-5-hydroxy-1-methyl Ethyl-2-(4-methyl-2-thiomethyl-thiazole)-1H-ind...

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PUM

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Abstract

The invention pertains to the field of medical technology and relates to compounds with antiviral activity and pharmaceutically acceptable salts thereof, preparation methods of the compounds and the application of the compounds in preparation of drugs, which are used for curing and/or preventing diseases caused by viral infection. The compounds of the invention have broad-spectrum antiviral activity and good clinical application value to the treatment of the viral infection, in particular the treatment of influenza.

Description

1. Technical field [0001] The invention relates to compounds with antiviral activity, pharmaceutically acceptable salts thereof, preparation methods of these compounds, and application of these compounds in the preparation of medicines for treating and / or preventing viral infection diseases, belonging to the technical field of medicine. 2. Background technology [0002] Influenza and acute respiratory viral infections are diseases with high clinical morbidity and wide range of diseases. Influenza is an acute respiratory infectious disease caused by influenza virus that seriously endangers human health. Its incidence ranks first among all respiratory infectious diseases and often causes seasonal global or local pandemics. According to statistics, 10% of the world's population, or about 500 million people, are infected by influenza virus every year. It occurs mostly in autumn and winter and winter and spring alternate seasons, often causing seasonal pandemics, and is one of t...

Claims

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Application Information

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IPC IPC(8): C07D417/12A61K31/427A61P31/12
Inventor 黄振华
Owner SHANDONG XUANZHU PHARMA TECH CO LTD
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