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Pharmaceutical compositions comprising S-(-)-N-Propargyl-1-amino indan

A technology of aminoindan and propargyl, which is applied in the field of pharmaceutical compositions containing S-(-)-N-propargyl-1-aminoindan, and can solve the problem of reduced selectivity of MAO subtypes

Inactive Publication Date: 2004-05-19
TEVA PHARMA IND LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the MAO isoform selectivity of these agents measured under in vitro conditions tends to decrease dramatically when measured in vivo

Method used

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  • Pharmaceutical compositions comprising S-(-)-N-Propargyl-1-amino indan
  • Pharmaceutical compositions comprising S-(-)-N-Propargyl-1-amino indan

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Di-(S-(-)-N-propargyl-1-aminoindan) D-tartrate

[0038] a) racemic N-propargyl-1-aminoindan

[0039] To a mixture of racemic 1-aminoindan (64 g), 15% aqueous sodium hydroxide solution (141 g), water (107 mL) and toluene (192 mL) was added propargyl benzenesulfonate (94.3 mL) over 20 minutes at room temperature. g). The resulting mixture was heated to 45°C for 4 hours, at which point pH > 12 was confirmed (45% sodium hydroxide was added if necessary), and the phases were separated. Water (64 mL) was added to the organic phase and the pH was adjusted to 2 with 33% aqueous sulfuric acid. The aqueous phase was separated, diluted with water and mixed with toluene. The pH was adjusted to 6 with 25% aqueous sodium hydroxide solution and the phases were separated. The aqueous phase was extracted again with toluene to ensure pH=6. The combined organic layers were concentrated in vacuo to give 51 g of crude racemic N-propargyl-1-aminoindan as a yellow oil.

[0040] b)...

Embodiment 2

[0043] S-(-)-N-propargyl-1-aminoindan methanesulfonate

[0044] Di-(S-(-)-N-propargyl-1-aminoindan)D-tartrate (15 g) from Example 1 and methanesulfonic acid (6 g) were dissolved in isopropanol (150 mL) The solution was heated to reflux for 30 minutes. The reaction mixture was allowed to cool to room temperature and the resulting precipitate was isolated by suction filtration to give the title compound (11.1 g), m.p. 157°C, [α] D -22°. About C 13 h 17 NSO 3 Anal. Calcd.: C, 58.43; H, 6.37; N, 5.24; S, 11.98; Found: C, 58.70; H, 6.39; N, 5.20;

Embodiment 3

[0046] S-(-)-N-propargyl-1-aminoindan methanesulfonate

[0047] To a solution of sodium hydroxide (4.8 g) in water (80 mL) was added bis-(S-(-)-N-propargyl-1-aminoindan) D-tartrate from Example 1 and toluene ( 80mL). After stirring for 30 minutes, the mixture was filtered through celite with suction and the organic layer was separated and washed with water. The organic phase was concentrated in vacuo, diluted with isopropanol and concentrated. The residue was dissolved in isopropanol (125 mL) and treated with methanesulfonic acid (11.5 g). The resulting mixture was heated to reflux for 30 minutes, filtered (celite) and allowed to cool to room temperature. The resulting precipitate was collected by filtration and washed with isopropanol to give the title compound having the same physical and chemical properties as the product of Example 2.

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Abstract

Pharmaceutical compositions for the treatment of a neurological disorder of neurotrauma or for improving memory in a patient comprising a therapeutically effective amount of S-(-)-N-proparygl-1-aminoindan or a pharmaceutically acceptable salt thereof as active ingredient, and a pharmaceutically active carrier. The pharmaceutical compositions are adapted, in particular for treating a neurological hypoxia or anoxia, neurodegenerative diseases. Parkinson's Disease, Alzheimer's Disease, neurotoxic injury, head trauma injury, spinal trauma injury or any other form of nerve damage.

Description

technical field [0001] The present invention relates to the new therapeutic application of S-(-)-N-propargyl-1-aminoindan and pharmaceutically acceptable salts thereof in the treatment of neuropathy or neurotrauma and improvement of memory of patients. [0002] The term "neurotrauma" as used herein refers to central nervous system injury and / or peripheral nervous system injury due to ischemic injury such as stroke, hypoxia or hypoxia, neurodegenerative disease, Parkinson's disease, Alzheimer's disease , neurotoxic injury, head traumatic injury, spinal traumatic injury or any other form of nerve injury. Background technique [0003] It is well known that R(-) selegiline (also known as L-selegiline, N,α-dimethyl-N-2-propenylphenethylamine) is the B form of monoamine oxidase (hereinafter referred to as "MAO-B ") inhibitors. [0004] PCT International Application No. WO92 / 17169 describes the activity of R(-)selegiline in maintaining, preventing loss of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61P25/16A61K31/135A61P25/28C07C211/42
CPCY10S514/878Y10S514/879C07C2102/08A61K31/135C07C211/42Y10S514/903C07C2602/08A61P25/00A61P25/16A61P25/28A61P9/10
Inventor R·莱维M·B·H·尤狄姆J·P·M·芬伯格S·科翰J·斯特林格
Owner TEVA PHARMA IND LTD
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