5-hydroxy indole derivative contain heterocyclic ring and applications thereof

Abstract

The invention relates to a 5-hydroxy indole derivative contain heterocyclic ring as shown in a general formula I. The 5-hydroxy indole derivative contains racemate, an optical isomer and salt and / or hydrate received on the pharmacy, wherein substituent groups R1, R2, X, Y and Z have meanings given in a specification. A compound of the formula I can be used for preparing medicine for curing and / or preventing viral infection and is particularly used for preparing anti-HBV medicine and anti-influenza medicine.

Description

technical field

[0001] The present invention relates to a series of heterocycle-containing 5-oxindole derivatives and uses thereof, as well as a pharmaceutical composition containing the compound as an active ingredient, and its preparation for treating and / or preventing viral infections, especially B Use in medicines for hepatitis virus and influenza virus infection. Background technique

[0002] Virus infection can cause a variety of diseases and seriously endanger human health and life. So far, more than 3,000 viruses have been discovered in the world, and new viruses are still being discovered. According to statistics, 60-65% of epidemic infectious diseases are caused by virus infection. Due to the complexity of the interaction between the virus and the host, most antiviral drugs have low toxicity to the human body or low antiviral effects when exerting therapeutic effects. This is also the reason for the slow development of antiviral drugs. As far as the current str...

Examples

Embodiment Construction

[0189] The examples are intended to illustrate, not limit, the scope of the invention. The H NMR spectra of the compounds were determined by Bruker ARX-300, and the mass spectra were determined by Agilent 1100 LC / MSD; the reagents used were analytical or chemically pure.

[0190] Preparation of thiol or thiophenol intermediates

[0191] Some mercaptans or thiophenols are commercially available; other mercaptans or thiophenols are prepared as follows:

[0192] method 1: preparation of

[0193] Add 100 mL (1.6 mole) of carbon disulfide into the three-neck flask, cool down to -5°C, add dropwise 300 mL of 15% ammonia-ethanol solution, and continue stirring at -5°C for 4 h. Suction filtration, washing with ether, and drying gave 152 g of ammonium dithiocarbamate as yellow crystals, with a yield of 86%.

[0194] Add 100 mL (0.85 mol) of acetophenone into 150 mL ethanol, keep the temperature not higher than -5°C, and add 320 g (0.85 mol) of phenyl trimethylammonium tribromide (P...

technical field

[0001] The present invention relates to a series of heterocycle-containing 5-oxindole derivatives and uses thereof, as well as a pharmaceutical composition containing the compound as an active ingredient, and its preparation for treating and / or preventing viral infections, especially B Use in medicines for hepatitis virus and influenza virus infection. Background technique

[0002] Virus infection can cause a variety of diseases and seriously endanger human health and life. So far, more than 3,000 viruses have been discovered in the world, and new viruses are still being discovered. According to statistics, 60-65% of epidemic infectious diseases are caused by virus infection. Due to the complexity of the interaction between the virus and the host, most antiviral drugs have low toxicity to the human body or low antiviral effects when exerting therapeutic effects. This is also the reason for the slow development of antiviral drugs. As far as the current str...

Examples

Embodiment Construction

[0189] The examples are intended to illustrate, not limit, the scope of the invention. The H NMR spectra of the compounds were determined by Bruker ARX-300, and the mass spectra were determined by Agilent 1100 LC / MSD; the reagents used were analytical or chemically pure.

[0190] Preparation of thiol or thiophenol intermediates

[0191] Some mercaptans or thiophenols are commercially available; other mercaptans or thiophenols are prepared as follows:

[0192] method 1: preparation of

[0193] Add 100 mL (1.6 mole) of carbon disulfide into the three-neck flask, cool down to -5°C, add dropwise 300 mL of 15% ammonia-ethanol solution, and continue stirring at -5°C for 4 h. Suction filtration, washing with ether, and drying gave 152 g of ammonium dithiocarbamate as yellow crystals, with a yield of 86%.

[0194] Add 100 mL (0.85 mol) of acetophenone into 150 mL ethanol, keep the temperature not higher than -5°C, and add 320 g (0.85 mol) of phenyl trimethylammonium tribromide (P...

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