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(E)-3-heteroaromatic propyl-2-enoic acid derivative as well as preparation and application thereof

A technology of alkyl and medicine, which is applied in the field of (E)-3-aryl heterocyclyl prop-2-enoic acid derivatives and their preparation and application, and can solve any problems such as

Inactive Publication Date: 2020-08-25
MEDCURIUS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Alzheimer's disease (AD) and Parkinson's disease (PD) are the two most common neurodegenerative diseases. Currently, there is no drug that can cure AD and PD, or even delay the progress of AD and PD. Some drugs for the treatment of AD and PD can only improve the symptoms of AD and PD patients

Method used

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  • (E)-3-heteroaromatic propyl-2-enoic acid derivative as well as preparation and application thereof
  • (E)-3-heteroaromatic propyl-2-enoic acid derivative as well as preparation and application thereof
  • (E)-3-heteroaromatic propyl-2-enoic acid derivative as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046]

[0047] Steps: Put 0.298 g (2 mmol) of pyridine-2-acrylic acid (compound A) and 10 ml of methanol into the reaction flask, slowly add 0.03 g (0.3 mmol) of concentrated sulfuric acid dropwise, react at room temperature for 3 hours, add dropwise saturated carbonic acid Sodium hydrogen solution, adjust the pH to about 8, then extract with dichloromethane, dry over anhydrous magnesium sulfate, filter, concentrate, and dry to obtain 0.223 g of compound I-1, yield: 68%. 1 H NMR (CDCl 3 ): δ3.82(s, 3H), 6.95(d, 1H, J=16.0Hz), 7.28(m, 1H), 7.43(d, 1H, J=8.0Hz), 7.70(d, 1H, J= 16.0Hz), 7.73(m, 1H), 8.66(d, 1H, J=4.0Hz); MS(ESI): m / z 164[M+H] + .

Embodiment 2

[0049]

[0050] Steps: Put 0.298 g (2 mmol) of pyridine-2-acrylic acid (compound A) and 10 ml of ethanol into the reaction flask, slowly add 0.03 g (0.3 mmol) of concentrated sulfuric acid dropwise, react at room temperature for 3 hours, add saturated carbonic acid dropwise Sodium hydrogen solution, adjust the pH to about 8, then extract with dichloromethane, dry over anhydrous magnesium sulfate, filter, concentrate, and dry to obtain 0.249 g of compound I-2, yield: 72%. 1 H NMR (CDCl 3 ): δ1.34(t, 3H, J=8.0Hz), 4.28(q, 2H, J=8.0Hz), 6.93(d, 1H, J=16.0Hz), 7.28(m, 1H), 7.44(d , 1H, J=8.0Hz), 7.69(d, 1H, J=16.0Hz), 7.73(m, 1H), 8.66(d, 1H, J=4.0Hz); MS(ESI): m / z 178[ M+H] + .

Embodiment 3

[0052]

[0053] Steps: put 0.298 g (2 mmol) of pyridine-3-acrylic acid (compound A) and 10 ml of methanol into the reaction flask, slowly add 0.03 g (0.3 mmol) of concentrated sulfuric acid, react at room temperature for 3 hours, add dropwise saturated carbonic acid Sodium hydrogen solution, adjust the pH to about 8, then extract with dichloromethane, dry over anhydrous magnesium sulfate, filter, concentrate, and dry to obtain 0.233 g of compound I-3, yield: 71%. 1 H NMR (CDCl 3 ): δ3.75 (s, 3H), 6.44 (d, 1H, J = 16.0Hz), 7.27 (dd, 1H, J = 4.0, 8.0Hz), 7.61 (d, 1H, J = 16.0Hz), 7.77 (d, 1H, J=8.0Hz), 8.54(d, 1H, J=4.0Hz), 8.67(s, 1H); MS(ESI): m / z 164[M+H] + .

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Abstract

The invention relates to a (E)-3-heteroaromatic propyl-2-enoic acid derivative, and also relates to a preparation method and pharmaceutical application thereof. The compound is a novel Nrf2 activatorand has the effects of resisting oxidative stress, resisting neuritis and enhancing mitochondrial functions and biogenesis by effectively activating an Nrf2 signal path, so that nerve cells are protected, and the compound can be used for treating neurodegenerative diseases and cerebral apoplexy. In addition, the novel Nrf2 activator can also be used to treat autoimmune diseases, diabetes and nephropathy, and other chronic diseases.

Description

technical field [0001] The present invention relates to a new class of Nrf2 activators, which can protect nerve cells by effectively activating the Nrf2 signaling pathway to produce anti-oxidative stress, anti-neuritis, and enhance mitochondrial function and biogenesis. For the treatment of multiple sclerosis (MS), Alzheimer's disease (AD), Parkinson's disease (PD), Huntington's disease (HD), amyotrophic lateral sclerosis (ALS), Friedreich's Ataxia (FRDA), spinal muscular atrophy (SMA), neuromyelitis optica (NMO) and spinocerebellar ataxia (SCA), among other neurodegenerative diseases, may also be used in the treatment of stroke. In addition, this new class of Nrf2 activators could also be used to treat autoimmune diseases, diabetes and kidney disease, among other chronic diseases. The present invention also relates to processes for the preparation of such compounds. Background technique [0002] Neurodegenerative diseases are incurable diseases that cause progressive dege...

Claims

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Application Information

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IPC IPC(8): C07D213/55C07D213/56C07D213/57A61K31/4402A61K31/4406A61K31/4409A61P25/28A61P25/14A61P25/16A61P21/00A61P9/00A61P11/00A61P3/10A61P13/12A61P9/10A61P9/12A61P9/04A61P11/06A61P19/02A61P17/06A61P29/00A61P27/02A61P37/06A61P5/14A61P37/02
CPCC07D213/55C07D213/56C07D213/57A61P25/28A61P25/14A61P25/16A61P21/00A61P9/00A61P11/00A61P3/10A61P13/12A61P9/10A61P9/12A61P9/04A61P11/06A61P19/02A61P17/06A61P29/00A61P27/02A61P37/06A61P5/14A61P37/02A61K31/505A61K31/426A61K31/421A61K31/4402A61K31/4164A61K31/4409A61K31/4439A61K9/0019
Inventor 赵旭阳文军
Owner MEDCURIUS INC
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