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Tertiary amine derivatives and their uses for treating a viral infection

A technology of compounds and medicinal salts, which is applied in the medical field and can solve problems such as restrictions on the application of antiviral drugs

Active Publication Date: 2022-02-01
ENYO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Furthermore, the emergence of drug resistance has severely limited the availability of antiviral drugs and created an urgent need for the development of new antiviral drugs against resistant forms

Method used

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  • Tertiary amine derivatives and their uses for treating a viral infection
  • Tertiary amine derivatives and their uses for treating a viral infection
  • Tertiary amine derivatives and their uses for treating a viral infection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0220] According to a further specific embodiment of the present invention, B represents:

[0221]

[0222] in:

[0223] -n is 0 or 1,

[0224] -R 2’ selected from hydrogen, oxygen, (C 1 -C 3 ) Alkyl and (C 1 -C 3 ) alkoxy, the (C 1 -C 3 ) Alkyl and (C 1 -C 3 ) alkoxy is optionally substituted by at least one halogen or hydroxyl,

[0225] -R 3’ selected from hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 ) Alkyl and (C 1 -C 3 ) alkoxy, the (C 1 -C 3 ) Alkyl and (C 1 -C 3 ) alkoxy is optionally substituted by at least one halogen or hydroxy, and

[0226] -R 4’ is hydrogen or -CONHR 5’ group, where R 5 ’ is hydrogen or (C 1 -C 3 )alkyl.

[0227] Preferably, B means:

[0228]

[0229] in:

[0230] -n is 0 or 1, preferably 1,

[0231] -R 2’ selected from hydrogen, oxygen and (C 1 -C 3 ) alkyl, preferably methyl, said (C 1 -C 3 ) alkyl is optionally substituted by at least one hydroxy group, R 2’ More preferably hydrogen,

[0232] -R 3’ is hyd...

Embodiment A

[0311] Example A - Chemistry

[0312] General synthetic route:

[0313] 1. Benzylic and aromatic substitution

[0314] -Route A:

[0315] By 1) using K 2 CO 3 (potassium carbonate) and CH 3 CN (acetonitrile) for benzylic or aromatic substitution followed by 2) using a) LiOH (lithium hydroxide) and b) NH 3 (Ammonia) and HATU (azabenzotriazole tetramethyluronium hexafluorophosphate) form an amide to prepare B as A compound of formula (I).

[0316] -Route B:

[0317] By 1) using K 2 CO 3 (potassium carbonate), CH 3 CN (acetonitrile) and Wilkinson catalyst (RhCl(PPh 3 ) 3 ) for a ruthenium-catalyzed synthesis followed by 2) using NaBH 4 (sodium borohydride), AcOH (acetic acid) and MeOH (methanol) or NaBH (OAc) 3 (sodium triacetoxy borohydride), and DCE (dichloroethane) carry out benzylic or aromatic substitution, preparation B is A compound of formula (I).

[0318] 2. Aliphatic and Heterocycloalkylamides

[0319] By 1) using K 2 CO 3 (potassium carbonate) ...

Embodiment B

[0320] Example B - Biology

[0321] antiviral effect

[0322] Materials & Methods

[0323]

[0324] Cytopathic Effect (CPE) Determination Experimental Procedure:

[0325] RSV titer: 6.9x10 6 pfu / ml

[0326] MOI = Pfu / number of cells used for infection

[0327] 1) Seed HEp-2 cells at 5000 cells / well in 25 μl assay medium in a 384-well plate at 37°C in 5% CO 2 Incubate for 24 hours. Every well was seeded with cells except the first row which contained medium only (low control).

[0328] 2) Compounds were dispensed using an Echo550 liquid handler. All compounds were used at 10 mM stock concentration. The positive control ribavirin was included as a control compound in all assays.

[0329] 3) Cells are expected to double every 24 hours.

[0330] 4) The next day, cells were infected with RSV MOI 0.5, and 5 μl of virus diluted in assay medium was added.

[0331] 5) Treat uninfected cells (high control) with 5 μl of assay medium.

[0332] 6) Centrifuge the pla...

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PUM

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Abstract

The present invention relates to a new class of tertiary amine derivatives of formula (I) and their uses for treating viral infections, particularly viral respiratory infections. The present invention further relates to pharmaceutical compositions comprising compounds of formula (I).

Description

technical field [0001] The present invention relates to the field of medicine, in particular to tertiary amine derivatives and their use in treating viral infections, especially viral respiratory tract infections. Background technique [0002] A virus is a small infectious agent that replicates only within the living cells of other organisms. They can infect all types of life forms, from plants and animals to microorganisms, including bacteria and archaea. Of these, more than 400 viruses are known to cause disease in humans, many of which cause severe disease and eventual death. In particular, HIV was listed as the sixth leading cause of death worldwide in 2012, causing 1.5 million deaths per year (WHO, Fact sheet N° 310, 2014). Seasonal influenza viruses are responsible for influenza, which affects approximately 20% of the world's population each year and causes 250,000 to 500,000 deaths (WHO, Fact Sheet N° 211, 2014). Hepatitis B and C together kill around 1.4 million p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/09C07C233/65C07D211/26C07D231/56A61K31/44A61P31/12C07C237/30C07C237/32C07C237/42
CPCC07D211/26C07D231/56C07D207/09C07C237/30C07C237/42C07C237/32C07C237/28A61K31/166A61K31/416A61K31/40A61P31/12A61P31/14C07C237/44C07D211/34
Inventor 艾瑞克·梅尔德伦彼得·梅钦贝诺伊特·德沙塞大卫·考辛
Owner ENYO PHARMA
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