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Compound, composition and method for preventing neurodegeneration in acute and chronic injury of central nervous system

A technology of compounds and compositions, applied in the field of neurological diseases

Inactive Publication Date: 2007-01-31
NEUROTECH SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the pathogenesis of ALS has not been elucidated, excitotoxicity is thought to be involved in the ALS process

Method used

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  • Compound, composition and method for preventing neurodegeneration in acute and chronic injury of central nervous system
  • Compound, composition and method for preventing neurodegeneration in acute and chronic injury of central nervous system
  • Compound, composition and method for preventing neurodegeneration in acute and chronic injury of central nervous system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 5

[0057]

[0058] Reagent (a) N,N-methylformamide (DMF), triethylamine, room temperature, 4 hours.

[0059] The specific compounds of interest in formula (I) are as follows:

[0060] 5-benzylaminosalicylic acid

[0061] 5-(4-Nitrobenzyl)aminosalicylic acid (NBAS)

[0062] 5-(4-Chlorobenzyl)aminosalicylic acid (CBAS)

[0063] 5-(4-Trifluoromethyl)aminosalicylic acid (TBAS)

[0064] 5-(4-fluorobenzyl)aminosalicylic acid (FBAS)

[0065] 5-(4-Methoxybenzyl)aminosalicylic acid (MBAS)

[0066] 5-(Pentafluorobenzyl)aminosalicylic acid (PBAS)

[0067] Ethyl 5-(4-nitrobenzyl)amino-2-hydroxybenzoate (NAHE)

[0068] 5-(4-Nitrobenzyl)-N-acetamido-2-hydroxybenzoic acid ethyl ester (NNAHE)

[0069] 5-(4-Nitrobenzyl)-N-acetamido-2-acetoxy-benzoic acid ethyl ester (NNAAE)

[0070] 5-(4-Nitrobenzoyl)aminosalicylic acid (NBAA)

[0071] 5-(4-Nitrobenzenesulfonyl)aminosalicylic acid (NBSAA)

[0072] 5-[2-(4-nitrophenyl)-ethyl]aminosalicylic acid (NPAA)

[0073] 5-[3-(4-nitrophenyl)n-propyl]aminosalic...

experiment Embodiment 1

[0123] Experimental Example 1: Antioxidant effect of 5-aminosalicylic acid

[0124] The neuroprotective effect of 5-aminosalicylic acid (AS) was tested in primary cortical cell cultures. Within 24 hours, AS containing 10-300 micromolar did not reduce neuronal death caused by exposure to 300 micromolar NMDA for 10 minutes (Fig. 1.a). Interestingly, increasing AS by 10-100 micromolar dose-dependently prevented the neurotoxicity of free radicals caused by exposure to ferrous ions for 24 hours (Fig. 1b). During and after zinc ion treatment, continuous addition of AS did not reduce neuronal death after 24 hours. These neurons were exposed to 300 micromole zinc ions for 30 minutes. The neuroprotective effect of AS against free radical neurotoxicity is attributed to the direct antioxidant properties of compound AS which reduces the level of DPPH (a stable free radical). Compared with trolox (a membrane-permeable vitamin E), AS is a weak oxidant.

[0125] Reactant

Concentr...

experiment Embodiment 2

[0128] Experimental Example 2: Neuroprotective effects of 5-benzylaminosalicylic acid and its derivatives

[0129] Neuroprotective effects of 1.5-benzylaminosalicylic acid

[0130] Synthesize BAS and test its ability to resist nerve damage, which is induced in cortical cell culture. At the same time, the addition of 300 micromoles of 5-benzylaminosalicylic acid (BAS) approximately reduced NMDA-induced neuronal death by 50% (Figure 2a). In the presence of 1 micromole of BAS, contact with 50 micromole of ferrous ions (Figure. 2b) or 10 millimole of BSO (Figure. 2c) caused a considerable reduction in neuronal death. Add 3 micromole With Moore BAS, neuronal death is basically completely blocked. Adding 30-300 micromolar BAS will dose-dependently reduce neuronal death caused by contact with 300 micromole zinc ions for 30 minutes in 24 hours. Like AS or trolox, BAS is a direct antioxidant (Table 2). The antioxidant properties of BAS can be observed at a dose as low as 1 micromolar.

[0...

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Abstract

The present invention provides a compound capable of preventing and curing nervous system diseases due to neuronal death and its method. Said invention includes synthesis of 5-benzyl aminosalicylic acid (BAS) and its derivative. The BAS and its derivative can protect cortical neuron from toxic injury of N-methyl-D-aspartate, zinc ion and active oxygen cluster, so that said invention provides compound and method for curing the diseases of apoplexy, cerebral trauma, epilepsy, spinal cord injury and neurodegenerative disease, etc.

Description

Technical field [0001] The present invention relates to new salicylic acid compounds, compositions, and methods. The compounds, compositions and methods are intended to prevent and prevent neurological diseases accompanied by neuronal death. Background technique [0002] Excitotoxicity and brain disease [0003] Excessive activation of ionized glutamate receptors that are sensitive to N-methyl-D-aspartate (NMDA receptors) can cause neuronal death, and it is known to mediate a variety of neurological diseases [Choi , Neuron 1:623-634 (1988)]. Glutamate is an excitatory neurotransmitter. It accumulates in a large amount in the brain and is susceptible to hypoxic-ischemic damage. Hypoxic-ischemic damage activates ionized glutamate receptors, making them resistant to calcium and sodium ions. Infiltration, subsequently causing neuronal death [Choi and Rothman, Annu Rev Neurosci: 13: 171-182 (1990)]. NMDA receptor orange antagonists significantly reduced hypoglycemia, hypoxia, hypoxia ...

Claims

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Application Information

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IPC IPC(8): C07C229/64C07C311/21A61K31/606A61P25/00A61P25/14A61P25/16A61P25/28
Inventor 郭秉周李英爱柳宝凛尹性和文镐相
Owner NEUROTECH SA
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