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Method for preparing rasagiline mesylate

A technology of rasagiline mesylate and methanesulfonic acid, which is applied in the preparation of sulfonate, preparation of amino-substituted functional groups, organic chemistry, etc., can solve the health hazards of production operators and the working environment, and the additional cost of methanesulfonic acid , Increase the process and cost, etc., to save the salt-forming process and solvent consumption, reduce the production process and solvent usage, and simplify the production steps

Inactive Publication Date: 2012-11-21
TOPHARMAN SHANGHAI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In the prior art, it is necessary to separate rasagiline basic, and then enter the following salt-forming process, that is, additionally use a solvent and add methanesulfonic acid in the last step of the salt-forming reaction, thereby increasing the process and cost
In addition, due to the strong corrosiveness of methanesulfonic acid, it is highly irritating to human mucous membranes, upper respiratory tract, eyes and skin, and is harmful to the health of production operators and the working environment.
At the same time, transportation, storage, and use of methanesulfonic acid may increase additional costs

Method used

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  • Method for preparing rasagiline mesylate
  • Method for preparing rasagiline mesylate
  • Method for preparing rasagiline mesylate

Examples

Experimental program
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Effect test

preparation example 1

[0023] Preparation example 1 propynyl alcohol methanesulfonate

[0024] Mix propynyl alcohol (2g, 35.7mmol), dichloromethane (20ml), and triethylamine (7.5ml, 53.7mmol), cool to 0°C, add methanesulfonyl chloride (3.3ml, 42mmol), after addition, the reaction solution Continue stirring at room temperature for 1 hour, quench the reaction with aqueous sodium bicarbonate, extract with dichloromethane (30ml×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, filter off the desiccant, and concentrate to obtain 4.2 g of propynyl alcohol methanesulfonate, yield: 88%. 1 HNMR (400MHz, CDCl 3 ): δ 4.85 (2H, d), 3.13 (3H, s), 2.73 (1H, t).

Embodiment 1

[0025] The preparation of embodiment 1 rasagiline mesylate

[0026] (R)-2,3-dihydro-1H-inden-1-amine (commercially purchased) (13.3g, 0.1mol), propynyl mesylate (26.83g, 0.2mol), acetonitrile (100ml) mixed , stirred and reacted at 45~50°C for 12 hours, stopped heating, naturally cooled to room temperature, filtered, the solid was washed with isopropanol (15ml×3), and dried to obtain 26.1g of white solid rasagiline mesylate, yield : 97.8%.

[0027] mp: 156-158°C; [α] D =+22.3° (c=2, EtOH);

[0028] 1 HNMR (400MHz, DMSO-d 6 ): δ9.50 (2H, br), 7.61 (1H, d), 7.42-7.29 (3H, m), 4.82 (1H, s), 4.02 (2H, s), 3.81 (1H, t), 3.17- 3.06 (1H, m), 2.94-2.84 (1H, m), 2.50-2.39 (1H, m), 2.32 (3H, s), 2.25-2.15 (1H, m).

Embodiment 2

[0029] The preparation of embodiment 2 rasagiline mesylate

[0030] (R)-2,3-dihydro-1H-indene-1-amine (35g, 0.26mol), propynol methanesulfonate (35.3g, 0.26mol), toluene (200ml) were mixed, and refluxed for 30 minutes , static, cooled to room temperature, a white precipitate precipitated, filtered by suction, and dried to obtain 64 g of white crystals, yield: 92%.

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Abstract

The invention relates to an improved method for preparing rasagiline mesylate. According to the method, (R)-2,3-dihydro-N-2-propargyl-1H-indenyl-1-amine mesylate which is rasagiline mesylate is prepared by reacting (R)-2,3-dihydro-1H-indenyl-1-amine with propargyl mesylate through a one-step process.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to an improved method for preparing rasagiline mesylate, which uses (R)-2,3-dihydro-1H-indene-1-amine and propynyl mesylate Reaction, a method for preparing (R)-2,3-dihydro-N-2-propargyl-1H-indene-1-amine mesylate in one step, namely rasagiline mesylate. Background technique [0002] Rasagiline mesylate, the chemical name is (R)-2,3-dihydro-N-2-propargyl-1H-indene-1-amine mesylate, and its structure is as follows: As shown in I), jointly developed by Teva Company of Israel and Lundbeck Company of Denmark, the drug has been approved by the European Union and the US FDA for the initial monotherapy of early Parkinson's disease, and can be used as a supplement to levodopa for treatment of late-stage patients medication. Rasagiline is an irreversible selective monoamine oxidase-B (MAO-B) inhibitor, which can enhance the signal transmission of dopamine, block the decomposition of dopa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/42C07C209/22C07C309/04C07C303/32
Inventor 张容霞刘正杨小军陈伟铭王震索瑾朱富强赵显国沈敬山
Owner TOPHARMAN SHANGHAI
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