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Pharmaceutical application of (E)-3-aromatic heterocyclic propyl-2-olefine acid derivative
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A pharmacy, alkyl technology, applied in the field of pharmaceutical use of (E)-3-arylheterocyclylprop-2-enoic acid derivatives, can solve any problems such as
Active Publication Date: 2021-07-23
MEDCURIUS INC
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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
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Embodiment 1
[0062]
[0063] Steps: 0.298 g (2 mmol) pyridin-2-acrylic acid (compound a) and 10 ml of methanol in the reaction flask, slowly added 0.03 g (0.3 mmol) concentrated sulfuric acid, and the room temperature was reacted for 3 hours, and saturated saturated carbonated. The hydrogensodiumhydrogen solution regulates about 8, then extracted with dichloromethane, dried off anhydroussulfate, filtered, concentrated, dried, 0.223 g of compound I-1, yield: 68%. 1 H NMR (CDCL 3 : Δ3.82 (S, 3H), 6.95 (D, 1H, J = 16.0 Hz), 7.28 (m, 1H), 7.43 (D, 1H, J = 8.0 Hz), 7.70 (D, 1H, J = 16.0Hz), 7.73 (m, 1H), 8.66 (D, 1H, J = 4.0 Hz); MS (ESI): M / Z 164 [M + H] + .
Embodiment 2
[0065]
[0066]Steps: 0.298 g (2 mmol) pyridine-2-acrylic acid (Compound A) and 10 ml of ethanol, slowly added 0.03 g (0.3 mmol) concentrated sulfuric acid, and saturated saturated carbonated at room temperature. The hydrogensodium hydrogen solution is adjusted to be about 8, then extracted with dichloromethane, dried off anhydroussulfate, filtered, concentrated, dried to give 0.249 grams of compound I-2, yield: 72%. 1 H NMR (CDCL 3 : Δ1.34 (T, 3H, J = 8.0 Hz), 4.28 (Q, 2H, J = 8.0 Hz), 6.93 (D, 1H, J = 16.0 Hz), 7.28 (M, 1H), 7.44 (D 1H, J = 8.0 Hz), 7.69 (D, 1H, J = 16.0 Hz), 7.73 (m, 1H), 8.66 (D, 1H, J = 4.0 Hz); MS (ESI): M / Z 178 [ M + h] + .
Embodiment 3
[0068]
[0069] Steps: 0.298 g (2 mmol) pyridine-3-acrylic acid (Compound A) and 10 ml of methanol in the reaction bottle, slowly drop 0.03 g (0.3 mmol) concentrated sulfuric acid, room temperature for 3 hours, drop saturated carbonated The hydrogen sodium hydrogen solution is adjusted to be about 8, then extracted with dichloromethane, dried with no water sulfate, filtrate, concentrated, dried, 0.233 g of compound I-3, yield: 71%. 1 H NMR (CDCL 3 : Δ3.75 (S, 3H), 6.44 (D, 1H, J = 16.0 Hz), 7.27 (DD, 1H, J = 4.0, 8.0 Hz), 7.61 (D, 1H, J = 16.0 Hz), 7.77 (D, 1H, J = 8.0 Hz), 8.54 (D, 1H, J = 4.0 Hz), 8.67 (S, 1H); MS (ESI): M / Z 164 [M + H] + .
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Abstract
The invention relates to a pharmaceutical application of (E)-3-aromatic heterocyclic propyl-2-olefine acid derivatives. The compound is a novel Nrf2 activator, and has the effects of resisting oxidative stress, resisting neuritis and enhancing mitochondrial function and biogenesis by effectively activating an Nrf2 signal channel, so that nerve cells are protected, and the compound can be used for treating neurodegenerative diseases and cerebral apoplexy. In addition, such novel Nrf2 activators can also be used for the treatment of autoimmune diseases, diabetes and nephropathy as well as other chronic diseases.
Description
Technical field [0001] The present application relates to a new type of NRF2 activator, which produces anti-oxidation stress, antioxmonitis, and enhanced mitochondrial function and biological occurrence by effectively activating NRF2 signaling pathways, thereby protecting nerve cells, so it can be used In the treatment of multiple sclerosis (MS), Alzheimer's disease (AD), Parkinson Disease (PD), Huntington (HD), Myocytreatry (ALS), Friedry Complementary disorders (FRDA), spinal cordmuscleatrophy (SMA), optic nerve spinalin (NMO) and spinal cortex (SCA) and other neurodegenerative diseases can also be used to treat stroke. In addition, such new NRF2 activators can also be used to treat autoimmune diseases, diabetes and nephropathy, and other chronic diseases. The present application also relates to the preparation of such compounds. Background technique [0002] Neurodegenerative disease is a disease that is still unable to cure, which causes nerve cells to perform sexual degene...
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Application Information
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