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Ezetimibe analogue and preparation method thereof

A technology for ezetimibe and analogs, applied in the field of ezetimibe analogs and their preparation, to achieve the effects of inhibiting absorption and increasing permeability

Inactive Publication Date: 2013-08-21
DONGHUA UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The benzene ring and the branched chain benzene ring on the N of the lactam are pharmacophore, the substitution of the benzene ring on the N has no great influence, but the substitution of the branched chain benzene ring is specific, only the unsubstituted or the C-4 position is replaced F replaces with effect

Method used

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  • Ezetimibe analogue and preparation method thereof
  • Ezetimibe analogue and preparation method thereof
  • Ezetimibe analogue and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 1. Synthesis of intermediate 3d (2,2,2-trifluoro-N-(4-fluorophenyl)acetimidoyl chloride):

[0038]

[0039] Add Ph 3 P (33mmol, 8.655g), Et 3 N (13.2mmol, 1.825mL), CCl 4 (55mmol, 5.275mL) and trifluoroacetic acid (11mmol, 1.254g), after the reaction bottle was stirred in an ice bath for 10 minutes, p-fluoroaniline (11mmol, 1.221g) was added to the reaction bottle with CCl 4 (55mmol, 5.275mL) solution, the mixture was reacted under reflux for 3h, the solvent was spin-off under reduced pressure, the solid mixture obtained was washed with n-hexane and filtered, and the filtrate was concentrated and distilled under reduced pressure to obtain product 3d, ((E) -4-fluoro-N-trifluoroacetal) aniline, the NMR data of this compound are consistent with those reported in the literature (J.Org.Chem.1993, 58, 32).

[0040] 2. Synthesis of intermediate 5d:

[0041] (S,Z)-4-benzyl-3-(4,4,4-trifluoro-3-(4-fluorophenylamino)but-2-enoyl)oxazolidin-2-one(5d).

[0042]

[0043]A...

Embodiment 2

[0071] 1. Inhibitory activity of Ezetimibe analogues on the absorption of exogenous cholesterol at the cellular level.

[0072] Tested cells: Caco-2

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PUM

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Abstract

The invention relates to an ezetimibe analogue and a preparation method thereof. The structure general formula of the ezetimibe analogue is shown in a structural formula, wherein in the formula, R1, R2 and R3 are selected from fluorine atom, hydroxyl, hydrogen atom and methoxy independently. The ezetimibe analogue is an ideal inhibitor for sucking cholesterol, and the cholesterol inhibitor can obviously prevent Caco-2 cells from sucking the cholesterol, so that the ezetimibe analogue has the prospect of becoming the inhibitor for sucking the cholesterol.

Description

technical field [0001] The invention belongs to the field of cholesterol absorption inhibitors and preparation thereof, in particular to an ezetimibe analogue and a preparation method thereof. Background technique [0002] A major risk factor for atherosclerosis and coronary heart disease is hypercholesterolemia. Although diet adjustment has a certain control effect on hyperlipidemia, most patients still need drug treatment in the end. A large number of clinical studies have confirmed that statin lipid-lowering drugs can significantly improve blood lipid disorders, and can reduce the morbidity and mortality of cardiovascular diseases, but due to the adverse reactions of large doses of statin drugs or differences in patient sensitivity, many patients fail to reach the goal. to the ideal lipid-lowering target. In 2002, Ezetimibe (SCH58235) was officially launched in the United States as a new type of cholesterol absorption inhibitor. It can be used alone or in combination wi...

Claims

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Application Information

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IPC IPC(8): C07D205/08A61P3/06
Inventor 卿凤翎刘应乐黄焰根
Owner DONGHUA UNIV
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