Cyclohexene compounds and application thereof

A compound, cyclohexene technology, applied in the directions of organic chemistry, drug combination, medical preparations containing active ingredients, etc. Superior application prospects, the effect of inhibiting influenza virus

Active Publication Date: 2017-03-15
GUANGZHOU HENOVCOM BIOSCI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, given the variability of influe

Method used

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  • Cyclohexene compounds and application thereof
  • Cyclohexene compounds and application thereof
  • Cyclohexene compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] a) (3R, 4S, 5S)-4-acetylamino-5-azido-3-((3S)-3-(2-methoxyethoxy)piperidine)-1-cyclohexene-1 - Preparation of ethyl formate

[0059]

[0060] According to the above reaction formula, 20 mmol of (3R, 4R, 5S)-4-acetylamino-5-azido-3-acetoxy-1-cyclohexene-1-carboxylic acid ethyl ester and 1 mmol of tetratriphenyl The phosphine palladium was placed in a dry two-necked bottle, and after the air in the system was replaced twice with nitrogen, 40 mL of redistilled DMF (dimethylformamide) was added with a syringe and stirred evenly, and 40 mmol of DIPEA (N, N-dimethylformamide) was added. isopropylethylamine) and stirred and cooled to 0°C, slowly added dropwise a solution of (3S)-3-(2-methoxyethoxy)piperidine trifluoroacetate in DMF (40mL), and continued Stir at 0°C for 20 minutes, move to an oil bath at 70°C for 1 hour, thin layer chromatography TLC (DCM:MeOH=10:1, i.e. dichloromethane:methanol=10:1) shows that the reaction is complete, slowly cool to 0°C, slowly Slowly a...

Embodiment 2

[0082] a) (3R, 4S, 5S)-4-acetylamino-5-azido-3-((3R)-3-(2-methoxyethoxy)piperidine)-1-cyclohexene-1 - Preparation of ethyl formate

[0083]

[0084] (3R,4S,5S)-4-Acetamido-5-azido-3-((3R)-3-(2-methoxyethoxy)piperidine)-1-cyclohexene-1-carboxylic acid Ethyl ester was prepared with reference to Example 1a).

[0085] Product characterization: 1 H-NMR (400MHz, CDCl 3 ): δppm6.837 (s, 1H, N H ), 5.715-5.694 (dd, 1H, 2-C H ), 4.201-4.184 (q, 2H, C H 2 CH 3 ), 3.925-3.877 (dd, 1H, 4-C H ), 3.781-3.715 (dd, 1H, 3-C H ), 3.604-3.530 (t, 2H, OC H 2 CH 2 O), 3.502-3.491 (m, 1H, NCH 2 C H OCH 2 ), 3.490-3.451 (t, 2H, OCH 2 C H 2 O), 3.351(s, 3H, OC H 3 ), 3.282-3.239 (d, 1H, NC H 2 CHOCH 2 ), 3.016-2.991 (t, 1H, NC H 2 CH 2 ), 2.893-2.837 (t, 1H, NC H 2 CH 2 ), 2.529-2.516 (m, 2H, NC H 2 CHOCH 2 , 5-C H ), 2.352-2.285 (dd, 1H, 6-C H 2 ), 2.248-2.202 (m, 1H, NCH 2 CH 2 C H 2 ), 2.182-2.177 (dd, 1H, 6-C H 2 ), 2.061(s, 3H, COC H 3 ), 1.959-1.935...

Embodiment 3

[0106] a) (3R, 4S, 5S)-4-acetylamino-5-azido-3-((3S)-3-((2-hydroxyethoxy)piperidine)-1-cyclohexene-1- Preparation of ethyl formate

[0107]

[0108] (3R, 4S, 5S)-4-acetylamino-5-azido-3-((3S)-3-((2-hydroxyethoxy)piperidine)-1-cyclohexene-1-carboxylic acid ethyl Esters were prepared with reference to Example 1a).

[0109] Product characterization: 1 H-NMR (400MHz, CDCl 3 ): δppm6.869 (s, 1H, N H ), 5.561-5.539 (dd, 1H, 2-C H ), 4.255-4.193 (q, 2H, COOC H 2 CH 3 ), 4.014-3.940 (dd, 1H, 4-C H ), 3.834-3.193 (m, 2H, OCH 2 C H 2 OH), 3.702-3.635 (m, 2H, OC H 2 CH 2 OH), 3.419-3.395 (dd, 1H, 3-C H ), 2.958-2.943 (m, 1H, NCH 2 C H ), 2.914-2.900 (m, 1H, NC H 2 CH), 2.787-2.750 (m, 1H, NC H 2 CH 2 ), 2.711-2.661 (m, 1H, NC H 2 CH 2 ), 2.585-2.261 (m, 1H, NC H 2 CH), 2.554-2.534 (m, 1H, 5-C H ), 2.332-2.262 (m, 1H, 6-C H 2 ), 2.071(s, 3H, COC H 3 ), 1.846-1.811 (m, 2H, NCH 2 C H 2 C H 2 ), 1.507-1.466 (m, 2H, NCH 2 C H 2 C H 2 ), 1.329-1.295...

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Abstract

The invention discloses cyclohexene compounds and an application thereof, and belongs to the field of medicinal chemistry. The cyclohexene compounds are cyclohexene compounds having a structure characteristic represented by the formula I and pharmaceutically acceptable salts and ester prodrugs or stereoisomers thereof; the cyclohexene compounds are subjected to influenza virus neuraminidase activity detection and are confirmed to have good inhibition activity on both wild type and drug-resistant mutant type influenza viruses; a part of the compounds have the inhibition activity IC50 on the wild type and drug-resistant mutant type influenza virus neuraminidase of less than 5 nM, and have the effect for significantly inhibiting the influenza viruses; the cyclohexene compounds or the pharmaceutically acceptable salts or the stereoisomers thereof are showed to have a good application prospect in preparation of anti-influenza virus drugs, thereby providing a new drug choice for clinic treatment of influenza.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a cyclohexene compound and its application. Background technique [0002] Influenza is a common respiratory disease, which can lead to debilitating patients and cause various complications. In severe cases, they need to be admitted to hospital for treatment or even die. Influenza is highly contagious, and it is easy to spread among the elderly, weak and weak people. Infection between each other, and even cause a large-scale epidemic. According to the World Health Organization, during seasonal influenza outbreaks, about 5%-15% of people will be affected by respiratory infections, and it is estimated that there are as many as 600-1.2 billion influenza cases each year, of which 300,000-500,000 people Died from influenza virus infection. [0003] Human influenza viruses are divided into three types: A (A), B (B), and C (C), among which type A is the most harmful and has...

Claims

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Application Information

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IPC IPC(8): C07D211/42C07D211/22A61K31/451A61P11/00A61P31/16
CPCC07D211/22C07D211/42A61K31/451A61P11/00A61P31/16C07D211/32
Inventor 张建存王坤刘燕李德耀
Owner GUANGZHOU HENOVCOM BIOSCI CO LTD
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