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Substituted imidazolium compounds, and preparation method, pharmaceutical compositions and application thereof

A technology of compounds and substituents, applied in the fields of substituted imidazolium salt compounds, their preparation, pharmaceutical compositions and their applications, which can solve the problems of non-cell permeability and limited application

Inactive Publication Date: 2018-10-23
XIAMEN VIVOHEALTHS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, none of these inhibitors has good cell permeability and cannot enter the interior of the cell to play a role, which greatly limits their application
The only reported aldolase inhibitor that is effective at the physiological level is TDZD-8 (Cancer Res. 2016, 76, 4259-4269.), but the inhibitor has a clear non-aldolase target - the kinase GSK3

Method used

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  • Substituted imidazolium compounds, and preparation method, pharmaceutical compositions and application thereof
  • Substituted imidazolium compounds, and preparation method, pharmaceutical compositions and application thereof
  • Substituted imidazolium compounds, and preparation method, pharmaceutical compositions and application thereof

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0194] In another aspect, the present invention also provides a method for preparing the compound described in any of the above technical schemes, comprising the following steps:

[0195]

[0196] Reaction conditions: (a) substitution reaction of brominated hydrocarbons; (b) substitution reaction of brominated hydrocarbons or

[0197]

[0198] Reaction conditions: (a) substitution reaction of brominated hydrocarbons under alkaline conditions (such as sodium hydride, sodium tert-butyl alkoxide, etc.); (b) substitution reaction of brominated hydrocarbons.

[0199] On the other hand, the present invention also provides the compound described in any of the above-mentioned technical schemes, its stereoisomer, its prodrug, or its pharmaceutically acceptable salt or pharmaceutically acceptable solvate and the compound containing the compound The pharmaceutical composition is used in the preparation of drugs for inhibiting cholesterol synthesis, drugs for reducing fatty acid syn...

specific Embodiment approach

[0208] The implementation of the present invention will be described in detail below through specific examples, but they should not be construed as limiting the present invention in any case.

[0209]

[0210] The compounds of the above general formula are divided into two types of synthetic preparation.

[0211] The general formula of compound I

[0212]

[0213] in,

[0214] The synthetic method of compound IA-general formula

[0215]

[0216] Preparation of Compound 1

[0217]

[0218] The compound 2-methylimidazole (821mg, 10mmol) was dissolved in 10mL of ethanol, and bromoalkane (12mmol) was added to the solution and stirred in an oil bath at 70°C until the reaction of 2-methylimidazole was complete (LC-MS track). Stop the reaction, concentrate the system, and perform silica gel column chromatography (dichloromethane / methanol) to obtain compound 1-alkyl-2-methylimidazole (1).

[0219] Preparation of Compound IA

[0220]

[0221] Multi-substituted benz...

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PUM

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Abstract

The invention relates to compounds with selective inhibitory activity against aldolase and a preparation method thereof, pharmaceutical compositions containing the compounds, and application of the compounds to preparation of drugs for inhibiting the synthesis of triglyceride and cholesterol, drugs for reducing the synthesis of fatty acid, drugs for preventing and / or treating obesity and type 2 diabetes, drugs for preventing and / or treating tumors, drugs for preventing and / or treating Parkinson's disease, drugs for preventing and / or treating Alzheimer's disease, or drugs for prolonging the life of mammals. The general structure of the compounds is as described in the specification.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, in particular to a class of compounds with selective aldolase inhibitory activity, a preparation method thereof, a pharmaceutical composition comprising the compound, and the preparation of these compounds for reducing fatty acid synthesis Drugs, drugs that inhibit triglyceride and cholesterol synthesis, drugs that prevent and / or treat obesity and type II diabetes, drugs that prevent and / or treat tumors, drugs that prevent and / or treat Parkinson's disease, prevent and / or treat Use in a medicament for Alzheimer's disease or a medicament for extending the lifespan of a mammal. Background technique [0002] 5'-adenosine monophosphate-activated protein kinase (AMPK) is an important molecule that regulates the energy balance of cells and the body (Nat. Rev. Mol. Cell Biol. 2012, 13, 251-262.). Because AMPK has multifunctional effects on carbohydrate, fat and cholesterol metabolism and biosy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/60C07D233/56C07D233/61C07D233/58C07D235/10C07D235/12A61P3/04A61P3/10A61P35/00A61P25/16A61P25/28A61P39/06
CPCC07D233/56C07D233/58C07D233/60C07D233/61C07D235/10C07D235/12A61P1/16A61P3/04A61P3/06A61P3/10A61P25/16A61P25/28A61P35/00A61P39/06C07D235/08
Inventor 邓贤明林圣彩张宸崧
Owner XIAMEN VIVOHEALTHS TECH CO LTD
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