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Tocopherol derivatives with a long hydroxylated chain, which can be used as neurotrophics

A hydroxyl and compound technology, applied in the application field of compounds of general formula and pharmaceutical compositions, can solve the problems of efficiency and application limitations, the inability of protein growth factors to penetrate various biological barriers, and low bioavailability

Inactive Publication Date: 2006-10-18
CENT NAT DE LA RECHERCHE SCI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] However, based on their molecular size and their physicochemical properties, protein growth factors cannot penetrate many biological barriers, especially the blood-brain barrier
so they don't get into the brain in sufficient quantities to have their beneficial effects
Also, their bioavailability is low, so their efficiency and applications are limited

Method used

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  • Tocopherol derivatives with a long hydroxylated chain, which can be used as neurotrophics
  • Tocopherol derivatives with a long hydroxylated chain, which can be used as neurotrophics
  • Tocopherol derivatives with a long hydroxylated chain, which can be used as neurotrophics

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Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0062] A. Preparation of Compounds of Structural Formula (I)

[0063] 1. Preparation of N-methoxy-N-methyl-16-hydroxyhexadecanoamide

[0064] 1.78 g of dimethylhydroxylamine (17.687 mmol; 3 eq.; molecular weight 97.55) were dissolved in 10 ml of dichloromethane which had been distilled under argon and cooled to -78°C. At -78°C, 8.8 ml of 2M trimethylaluminum in hexane (17.687 mmol; 3 eq.; molecular weight 72.09) was added dropwise, and the reaction mixture was stirred at room temperature for half an hour. The solution was then cooled to 0° C. and 1.55 g of oxacycloheptadecan-2-one (5.895 mmol, 1 equiv; molecular weight 254.42) dissolved in 5 ml of distilled dichloromethane was added dropwise. The reaction mixture was stirred at room temperature. TLC analysis indicated complete reaction after 1.5 hours. The solution was added dropwise to 60 mL of a 2:1 ether / methanol mixture cooled to -78°C and filtered through celite. 100 ml of saturated aqueous sodium bicarbonate was adde...

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Abstract

The present invention relates to any isolated or synthetic compound, in particular a compound of general formula (I), which is capable of modulating the cellular specialization of neural stem cells, favoring the differentiation and subsequent survival of neurons and glial cells during differentiation. and differentiation of oligodendrocyte precursor cells into mature oligodendrocytes. In addition, the compounds according to the invention are able to reduce inflammatory substances in diseases affecting the nervous system, in particular by reducing the activation of microglia and / or astrocytes and / or by reducing reactive gliosis. The present invention also relates to a method for preparing the compound and the use of the compound in the preparation of a pharmaceutical composition for the prevention or treatment of diseases affecting the nervous system. More specifically, the compounds of the present invention have the following general formula (I).

Description

technical field [0001] The present invention relates to any isolated or synthetic compound, especially a compound of general formula (I), capable of regulating the cell specialization of neural stem cells (regulation of neuron / glial cell ratio), promoting neuronal and glial cell differentiation during differentiation. Glial cell differentiation and subsequent survival and differentiation of oligodendrocyte precursor cells to mature oligodendrocytes. In addition, the compounds according to the invention are able to reduce inflammatory substances in diseases affecting the nervous system, in particular by reducing the activation of microglia and / or astrocytes and / or by reducing reactive gliosis. The invention also relates to compositions comprising these compounds as well as processes for their preparation and their use in the preparation of pharmaceutical compositions for the prevention or treatment of diseases affecting the nervous system. Background technique [0002] The c...

Claims

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Application Information

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IPC IPC(8): C07D311/72A61K31/335A61K31/355A61P25/16A61P25/28C07D307/80C07D313/08
CPCC07D307/80C07D311/72A61P21/04A61P25/00A61P25/16A61P25/28A61P43/00A61P9/10
Inventor 刘鹏保罗·霍伊施林蒂埃里·穆勒埃莱奥诺拉·莫尔加
Owner CENT NAT DE LA RECHERCHE SCI
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