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Derivate von dihydroxyphenylalanin

A technology of residues and compounds, applied in the field of dihydroxyphenylalanine derivatives, can solve problems such as the inability to ensure the formation of a sufficient amount of the chemical messenger dopamine

Inactive Publication Date: 2008-06-25
ELLNEUROXX LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the formation of sufficient amounts of the chemical messenger dopamine cannot be guaranteed

Method used

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  • Derivate von dihydroxyphenylalanin
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  • Derivate von dihydroxyphenylalanin

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0095] Example 1: Synthesis of O,O'-Diacetyl-L-DOPA-ethylene glycol lipoate (Diacetyl-DOPA-ethylene glycol lipoate; Compound 1)

[0096]

[0097] Lipoic acid is converted to lipoic acid monoethylene glycol ester using excess ethylene glycol and DCC. Conversion of L-DOPA to Fmoc-L-DOPA by Fmoc-succinimide, and acetylation of Fmoc-L-DOPA to N-Fmoc via acetic anhydride under Schotten-Baumann conditions -O,O'-diacetyl-L-DOPA. The coupling product N-Fmoc-O,O'-diacetyl-L-DOPA ethylene glycol-racemic (rac)-lipoate was obtained by converting the above lipoic acid monoethylene glycol ester with DDC. The Fmoc protecting group was cleaved via tetrabutylammonium fluoride in DMF.

[0098] Purity (HPLC): 81-85%, clear yellow oil

[0099] 13 C-NMR (100.6MHz, d 4 - Methanol), δ (ppm):

[0100] 20.47; 25.71; 29.74; 34.76; 35.68; 39.33; 41.07; 41.27; 57.51;

example 2

[0101] Example 2: Synthesis of O,O'-diacetyl-L-DOPA-(R,S)-lipoic acid amide (Diacetyl-DOPA-lipoic acid amide; Compound 2)

[0102]

[0103] O, O'-diacetyl-L-DOPA-rac-lipoic acid amide is obtained by reacting L-DOPA-rac-lipoic acid amide with acetic anhydride under mild alkaline reaction conditions.

[0104] Purity (HPLC)>95%, clear yellow oil

[0105] 13 C-NMR (100.6, CDCl 3 ), δ(ppm):

[0106] 20.65; 25.16; 28.67; 34.50; 35.99; 36.48; 38.43; 40.17; 52.74;

example 3

[0107] Example 3: Synthesis of L-DOPA-(D,L)-lipoic acid amide (DOPA-lipoic acid amide; compound 3)

[0108]

[0109] L-DOPA-rac-ac- Lipoic acid amide. Lipoyl chloride is obtained from lipoic acid and oxalyl chloride, and lipoic acid succinimide ester is obtained from lipoic acid, hydroxysuccinimide and DCC.

[0110] Purity (HPLC) 97%, yellow highly viscous oil

[0111] 13 C-NMR (100.6, d 4 - Methanol), δ (ppm):

[0112] 26.58; 29.60; 35.69; 36.60; 37.83; 39.31; 46.23; 55.00; 57.43;

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Abstract

The invention relates to dihydroxyphenylalanine derivatives, the production thereof, and pharmaceutical compositions containing said dihydroxyphenylalanine derivatives. The invention further relates to the use of said dihydroxyphenylalanine derivatives and pharmaceutical compositions for the treatment and prevention of movement disorders, neurodegenerative diseases, Alzheimer, Parkinson's disease, hemiatrophy hemiparkinsonism, Parkinson's syndrome, Lewy bodies disease, frontotemporal dementia, Lytico-Bodig disease (Parkinsonism-dementia-amyotrophic lateral sclerosis, striatonigral degeneration, Shy-Drager syndrome, sporadic olivopontocerebellar degeneration, progressive pallidal atrophy, progressive supranuclear palsy, Hallervorden-Spatz disease, Huntington's disease, X chromosome-linked dystonia (Morbus Lubag), mitochondrial cytopathy with striatal necrosis, neuroacanthocytosis, restless leg syndrome, Wilson's disease.

Description

technical field [0001] The present invention relates to a dihydroxyphenylalanine derivative, a synthesis method thereof, an application thereof and a pharmaceutical composition comprising the dihydroxyphenylalanine derivative. Background technique [0002] DOPA is named 2-amino-3-(3,4-dihydroxyphenyl)-propionic acid by the International Union of Pure and Applied Chemistry (IUPAC), commonly known as Levodopa and used especially in the treatment of Parkinson's sick. [0003] Parkinson's disease, also known as Parkinson's syndrome, is a chronic disease that still cannot be cured. The course of the disease is characterized by the slow death of nerve cells that do not contain the chemical messenger dopamine in the substantia nigra (black matter) of the brain. Therefore, sufficient amounts of the chemical messenger dopamine cannot be guaranteed to be formed. Mutations (eg, Lewy bodies) can also be found in other parts of the brain, such as the nucleus coeruleus, raphe nucleus, ...

Claims

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Application Information

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IPC IPC(8): C07D339/04C07D409/14C07C233/87C07C233/49A61K31/166A61K31/16A61K31/385A61P25/16
CPCC07D339/04A61P25/00A61P25/08A61P25/14A61P25/16A61P25/28A61P43/00A61P9/10
Inventor 吉塞拉·苏希洛
Owner ELLNEUROXX LTD
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