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1,2,4‑Triazine derivatives for the treatment of viral infections

A compound and alkyl technology, applied in antiviral agents, drug combinations, allergic diseases, etc., can solve problems such as the complexity of innate immune model methods

Active Publication Date: 2017-03-08
CENT NAT DE LA RECHERCHE SCI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This could complicate the approach of using experimental animals as models of human innate immunity

Method used

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  • 1,2,4‑Triazine derivatives for the treatment of viral infections
  • 1,2,4‑Triazine derivatives for the treatment of viral infections
  • 1,2,4‑Triazine derivatives for the treatment of viral infections

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Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0043] The preparation of formula (I) compound

[0044] Experimental part

[0045] 2 Preparation

[0046]

[0047] At room temperature, to 1 (20g, 176.9mmol, 1eq.) of H 2 Add Br to O (320mL) solution 2 (24mL, 466.8mmol, 2.6eq.). The mixture was stirred at 60 °C for 15 h, then NH 4 OH (50 mL). Then HCl (6N aq.) was added slowly until pH = 5, and the mixture was extracted with ethyl acetate (3 x 800 mL). The combined organic layers were washed with water and brine, dried (MgSO 4 ), the solids were removed by filtration, and the solvent of the filtrate was concentrated under reduced pressure to obtain 2 (16 g).

[0048] 1 H NMR (400MHz, DMSO-d 6 ): δppm 12.56(m,1H),12.31(m,1H)

[0049] 3 preparation

[0050]

[0051] At room temperature, to 2 (16g, 83.3mmol) of POCl 3 (80mL) solution was added PCl 5 (36.1 g, 173.4 mmol) and N,N-diethylaniline (35 mL, 221.7 mmol). The mixture was stirred at 120°C for 5 hours, then excess solvent was removed under reduced pressu...

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Abstract

The present invention relates to 1,2,4-triazine derivatives, their preparation methods, pharmaceutical compositions, and their use in treating viral infections.

Description

technical field [0001] The present invention relates to 1,2,4-triazine derivatives, their preparation methods, pharmaceutical compositions, and their use in treating viral infections. Background technique [0002] The present invention relates to the use of 1,2,4-triazine derivatives in the treatment of viral infections, immune or inflammatory diseases, thereby involving the modulation or agonism of toll-like receptors (TLRs). Toll-like receptors are fundamental transmembrane proteins characterized by an extracellular leucine-rich domain and a cytoplasmic extension containing a conserved region. The innate immune system is able to recognize pathogen-associated molecular patterns through these TLRs expressed on the cell surface of certain types of immune cells. Recognition of a foreign pathogen activates cytokine production and co-stimulates the upregulation of molecules on phagocytes. This results in modulation of T cell behavior. [0003] It is estimated that most mammal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12C07D253/07A61K31/53A61P31/12
CPCC07D253/07C07D401/12C07D253/075A61P29/00A61P31/12A61P37/00
Inventor V·跟巴斯P·朱博C·瓦罗V·勒瓦谢J-F·邦凡蒂D·G·麦克格文J·E·G·吉耶蒙
Owner CENT NAT DE LA RECHERCHE SCI