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Novel 5-hydroxy-3-carboxylate indoles derivant and method for preparing the same

A derivative and indole technology, applied in the field of novel 5-hydroxy 3-carboxylate indole derivatives and its preparation, can solve the problems of influenza vaccine failure, drug tolerance and side effects, and anti-influenza drug types and limited number of issues

Inactive Publication Date: 2004-03-17
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Due to the virus variability and multi-drug resistance of influenza virus strains, the originally effective influenza vaccine failed quickly; the types and quantities of existing anti-influenza drugs are limited, and usually have drug resistance and toxic side effects

Method used

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  • Novel 5-hydroxy-3-carboxylate indoles derivant and method for preparing the same
  • Novel 5-hydroxy-3-carboxylate indoles derivant and method for preparing the same
  • Novel 5-hydroxy-3-carboxylate indoles derivant and method for preparing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095] 6-Bromo-4-(diethylamino)methyl-5-hydroxy-1-methyl-2-[(phenyl)thio]methyl-1H-indole-3-carboxylic acid ethyl ester salt salt

[0096] Step A: Preparation of ethyl 3-methylamino-3-butenoate (1)

[0097] Under stirring with slight heat, 274ml (1.4mol) of methylamine solution was added dropwise to 300ml of 50% sodium hydroxide solution, and the generated methylamine gas was introduced into 169ml (1.3mol) of ethyl acetoacetate, the reaction was exothermic, and stirred , cooling the reaction solution in a water bath, and maintaining the reaction temperature at 35-40° C. until the reaction solution becomes cloudy to obtain a light green turbid solution, stop aeration, and stir overnight at room temperature. The next day, stir and pump air for 2 hours, add 300ml of diethyl ether to separate layers, wash the organic layer with water until the pH is 8, dry over anhydrous sodium sulfate, and concentrate the organic layer under reduced pressure to obtain 180.6g of transparent liqui...

Embodiment 2

[0109] 6-Bromo-4-(dimethylamino)methyl-5-hydroxy-1-ethyl-2-[(4-isopropylphenyl)thio]methyl-1H-indole-3- ethyl carboxylate phosphate

[0110] 1 H-NMR (DMSO): 1.25~1.38(m, 12H), 2.49(s, 6H), 2.95(m, 1H), 4.18~4.34(s, m, 6H), 4.69(s, 2H), 7.26( d, 2H), 7.36(d, 2H), 7.38(s, 1H), 7.89(s, 1H)

Embodiment 3

[0112] 6-Bromo-4-(dimethylamino)methyl-5-hydroxy-1-ethyl-2-[(4-fluorophenyl)thio]methyl-1H-indole-3-carboxylic acid Ethyl phosphate

[0113] 1 H-NMR(DMSO): 1.23(t, 3H), 1.29(t, 3H), 2.38(s, 6H), 4.11(q, 2H), 4.20~4.24(m, 4H), 4.60(s, 2H) , 7.16(m, 2H), 7.35(m, 2H), 8.01(s, 1H)

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PUM

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Abstract

The present invention is one novel 5-hydroxyl-3-carboxylic ester indole derivative and its preparation process. It provides one new kind of efficient influenza virus resisting medicine, and also relates to its medicinal acceptable salt and medicinal composition with the compound as active component. As an antiviral agent, the present invention has obvious inhibition to influenza virus and respiratory track virus. The present invention also relates to the application of the derivative in preparing influenza virus resisting agent and medicine for preventing acute viral respiratory track infection.

Description

Technical field: [0001] The invention relates to the technical field of medicine, in particular to novel 5-hydroxyl 3-carboxylate indole derivatives and a preparation method thereof. Background technique: [0002] Influenza is an acute viral respiratory infectious disease caused by influenza virus, mainly affecting the elderly and people with compromised immune systems. Influenza viruses belong to the Orthomyxoviridae family. According to different antigens, they are divided into three types: A, B, and C. Type A often appears in an epidemic form and can cause a worldwide pandemic. Type B often causes local outbreaks. Mainly occurs in distributed form. In the epidemic of influenza, A virus plays a major role, which is the main cause of influenza epidemic at present. [0003] Due to the virus variability and multi-drug resistance of influenza virus strains, the originally effective influenza vaccine failed quickly; the types and quantities of existing anti-influenza drugs ar...

Claims

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Application Information

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IPC IPC(8): A61K31/405A61P31/16C07D209/42
CPCC07D209/42A61K31/405A61P11/00A61P31/12A61P31/16
Inventor 宫平
Owner SHENYANG PHARMA UNIVERSITY
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