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Phenylacrylate compound as well as preparation method and application thereof

A technology of phenylacrylate and compound, applied in the field of phenylacrylate compound and preparation thereof, can solve the problems such as not being able to show ideal medicinal effect and the like

Active Publication Date: 2018-05-29
SUZHOU PHARMAVAN CANCER RES CENT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the process of treating stroke, the drug also needs to pass through the blood-brain barrier and reach the effective concentration before it can work. Most of the drug molecules cannot penetrate the blood-brain barrier to reach the brain. Therefore, many drugs for the treatment of brain diseases Some drugs can show good drug-target binding activity in in vitro tests, but they can't show ideal drug effects in animal tests

Method used

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  • Phenylacrylate compound as well as preparation method and application thereof
  • Phenylacrylate compound as well as preparation method and application thereof
  • Phenylacrylate compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Synthesis of Compound A: Under nitrogen protection, malonic acid mono(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol ester (11.5g, 47.9 mmol), 3-fluoro-4-hydroxyl-5-methoxybenzaldehyde (7.3g, 42.9mmol) were added in toluene (100ml), added pyridine (7.6g, 95.8mmol), piperidine (0.4g, 4.7 mmol), the temperature was raised to 120°C for 5 hours. After the reaction was completed, the reaction solution was allowed to cool, and 1N hydrochloric acid solution, saturated NaHCO 3 solution, washed with saturated NaCl solution, dried over anhydrous sodium sulfate for 4 h, concentrated to dryness, and recrystallized from ethyl acetate / petroleum ether to obtain 10.2 g of white powder solid with a yield of 68.5%. EI-MS M / Z349.2[M + ], 347.3[M - ].

[0088] 1 H-NMR (CDCl 3 ,500MHz) 0.88, 0.90, 0.94 (each 3H, s, H-8, 9, 10), 1.05 (1H, dd, J=17.2, 4.3Hz, H-3b), 1.25 (2H, m, H-5b , H-6b), 1.70(1H,m,H-4),1.78(1H,m,H-5a),2.01(1H,m,H-6a),2.41(1H,m,H-3a), 3.96 (3H, s, -OMe), 5.01 (...

Embodiment 2

[0090] Synthesis of Compound A: Under nitrogen protection, malonic acid mono(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol ester (5.3g, 22.1 mmol), 3-fluoro-4-hydroxyl-5-methoxybenzaldehyde (3.0g, 17.6mmol) were added in toluene (50ml), piperidine (0.38g, 4.4mmol), acetic acid (0.26g, 4.4 mmol), the temperature was raised to 120°C for 5 hours. After the reaction was completed, the reaction solution was allowed to cool, and 1N hydrochloric acid solution, saturated NaHCO 3 solution, washed with saturated NaCl solution, dried over anhydrous sodium sulfate for 4 h, concentrated to dryness, and recrystallized from ethyl acetate / petroleum ether to obtain 4.3 g of white powder solid, with a yield of 70.5%.

Embodiment 3

[0092] Synthesis of Compound B: Under nitrogen protection, malonic acid mono(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol ester (11.5g, 47.9 mmol), 3,4-dihydroxy-5-methoxybenzaldehyde (7.2g, 42.9mmol) were added to toluene (100ml), and pyridine (7.6g, 95.8mmol), piperidine (0.4g, 4.7mmol) were added ), heated up to 120°C for 5 hours, after the reaction was over, let the reaction liquid cool down, and washed with 1N hydrochloric acid solution, saturated NaHCO 3 solution and saturated NaCl solution, dried over anhydrous sodium sulfate for 4 h, concentrated to dryness, and recrystallized from ethyl acetate / petroleum ether to obtain 8.3 g of white powder solid, with a yield of 55.8%. EI-MS M / Z347.2[M + ], 345.2[M - ].

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PUM

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Abstract

The invention provides a phenylacrylate compound as well as a preparation method and application thereof. The phenylacrylate compound has the structure shown in a formula I. The phenylacrylate compound and pharmaceutically acceptable salt, solvent compound, predrug, tautomer or stereoisomer or medicinal composition thereof have good anti-inflammatory and antiplatelet effects, have a long treatmenttime window, do not have remarkable side effect, is safe and effective, can serve as antithrombus, anti-inflammatory and stroke-treating medicines and have wide application prospects.

Description

technical field [0001] The invention belongs to the technical field of chemistry and medicine, and relates to a phenylacrylate compound and its preparation method and application. Background technique [0002] Stroke is a disease in which brain tissue is damaged due to sudden rupture of blood vessels in the brain or blood circulation disorder caused by blood vessel blockage. Ischemic stroke refers to the necrosis of local brain tissue including nerve cells, glial cells and blood vessels due to lack of blood supply. [0003] According to the "China Cardiovascular Disease Report 2013", the prevalence of cerebrovascular diseases in my country is on the rise. According to the 2010 Global Burden of Disease Study, stroke is the third leading cause of disability-adjusted life years (DALYs). At the same time, stroke is the second leading cause of death among people over 60 years old, and it is one of the neurological diseases with the highest fatality rate. In my country, stroke ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/734A61K31/216A61P7/02A61P29/00A61P9/10
CPCC07B2200/07C07C69/734
Inventor 刘乾李云森邓世平高原娄山宁俞云会江传亮
Owner SUZHOU PHARMAVAN CANCER RES CENT CO LTD
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