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A kind of 3,4-diarylmaleimide derivative and its preparation method and application

A technology of maleimide and derivatives, which is applied in the field of 3,4-diarylmaleimide derivatives and its preparation, and can solve problems such as safety risks and poor effects

Active Publication Date: 2019-10-29
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved in the present invention is to provide a kind of 3,4-diarylmaleimide derivatives, to solve problems such as poor effect and potential safety risks existing in the prior art

Method used

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  • A kind of 3,4-diarylmaleimide derivative and its preparation method and application
  • A kind of 3,4-diarylmaleimide derivative and its preparation method and application
  • A kind of 3,4-diarylmaleimide derivative and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0086] Embodiment 1: Preparation of 2-bromo-1-(4-fluorophenyl)ethanone

[0087]Dissolve 20g (144.7mmol) of p-fluoroacetophenone in 200mL of acetonitrile, slowly add 23.12g (144.7mmol) of Br 2 50 mL of acetonitrile solution, stirred overnight at room temperature. After the reaction was complete, the reaction solution was concentrated and removed, redissolved in ethyl acetate, washed three times with saturated brine, dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure to remove the solvent. 1 mL of ethyl acetate was slurried and filtered to obtain 28 g of white solid, yield: 89.2%, mp: 40-41°C.

[0088] 1 H-NMR (300M, CDCl 3 ):4.40(s,2H,-CH 2 -),7.17(m,2H,Ar-H),8.02(m,2H,Ar-H); MS:calcd.m / z[M]215.96,found m / z[M-H] - 215.0.

Embodiment 2

[0089] Example 2: Preparation of 2-azido-1-(4-fluorophenyl)ethanone

[0090] Dissolve 31.59g (146mmol) of 2-bromo-1-(4-fluorophenyl)ethanone in 150mL of methanol, and slowly add 50mL of 11.38g (175mmol) of NaN at 0°C 3 Aqueous solution, stirred overnight at room temperature. After the reaction was complete, 50 mL of water was slowly added dropwise at 0°C, a large amount of white solid precipitated, filtered and dried to obtain 25.25 g, yield: 96.6%.

[0091] 1 H-NMR (300M, CDCl 3 ):4.52(s,2H,-CH2-),7.17(m,2H,Ar-H),7.94(m,2H,Ar-H); MS:calcd.m / z[M]179.05,found m / z[M+H] + 180.0.

Embodiment 3

[0092] Embodiment 3: Preparation of 2-amino-1-(4-fluorophenyl)ethanone hydrochloride

[0093] Dissolve 25.25g (141mmol) of 2-azido-1-(4-fluorophenyl)ethanone in 100mL of methanol, slowly add 42.85g (423mmol) of concentrated hydrochloric acid (concentration 36%) dropwise, add 2g of Pd / C , catalytic hydrogenation at room temperature. After the reaction is complete, filter the Pd / C, distill off the solvent under reduced pressure, slurry with 50mL ether, and filter to obtain 22.72g of white solid, yield: 85%, mp: 213-215°C.

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Abstract

The invention discloses a 3,4-diaryl maleimide derivative represented by a general formula I and a pharmaceutical salt form thereof. The invention further discloses a preparation method for the 3,4-diaryl maleimide derivative and application of the 3,4-diaryl maleimide derivative in preparation of drugs for preventing or treating atherosclerosis and drugs for lowering plasma cholesterol level. Compared with the prior art, the 3,4-diaryl maleimide derivative can be applied to the treatment or prevention of atherosclerosis or the lowering of plasma cholesterol level and has higher plasma cholesterol lowering activity, so that the market prospect is more extensive.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and specifically relates to a 3,4-diarylmaleimide derivative, a preparation method and application thereof. Background technique [0002] Cardiovascular and cerebrovascular diseases are the number one killer that endangers human life and health today. Hyperlipidemia caused by blood lipid metabolism disorders is one of the important causes of cardiovascular and cerebrovascular diseases such as atherosclerosis, liver cirrhosis, and hypertension. Currently clinically used cholesterol-lowering drugs mainly include statins, fibrates, niacin derivatives and bile acid sequestrants, but the side effects of these drugs are also obvious, especially cerivastatin among statins There have been multiple clinical deaths due to side effects of rhabdomyolysis. (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)- 2-azetidinone (Ezetimibe, Ezetimibe, Zetia TM ) is a new ty...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/444A61K31/4015A61P3/06A61P9/10
CPCC07D207/444Y02P20/55
Inventor 王玉斌陈博伦袁新睿诸丽娟夏易能
Owner NANJING TECH UNIV
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