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Novel method for removing methyl impurity in preparation of asenapine

A technology of asenapine maleate and demethylation, which is applied in the field of new process synthesis to achieve the effect of simple process, high quality and easy access to raw materials

Inactive Publication Date: 2016-05-11
AVENTIS PHARMA HAINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology describes an improved way to make certain chemicals called amiscippride that can be used safely without causing harm or even killing people around them. It involves reacting two different substances together at high temperatures under specific conditions. These reactions produce desired products while minimizing any unwanted side effectes such as decomposition or contamination from other components within their molecules themselves.

Problems solved by technology

This patented technical problem addressed in this patents relates to developing new drugs called asenspone (also known as 4'-chloperiden-5 '-azepan-2' -ziprene) which have potential use against neurologically relevant diseases such as Alzheimer disease and Parkinson syndrome caused by excessive levels of certain chemical substances like amphetimide used during therapy.

Method used

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  • Novel method for removing methyl impurity in preparation of asenapine
  • Novel method for removing methyl impurity in preparation of asenapine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 15.0 g of asenapine maleate (compound ASP) and 15.8 g of sodium carbonate into the reaction flask, then add 250 ml of EA to dissolve, and stir until completely dissolved. The liquid was washed with water for 2 hours, and the filtrate was spin-dried to obtain 11.15 g of a light yellow solid, namely asenapine (compound ASP-1), with a yield of 98%.

Embodiment 2

[0022] Asenapine (Compound ASP-4) 11.15g was dissolved in 350mL of toluene, 25.1g of ethyl chloroformate was added, stirred and heated to reflux, monitored by TLC. After the reaction was complete, the temperature was lowered, washed with water and saturated saline, separated, and the organic phase was spin-dried to obtain an oily substance, stirred with n-hexane to precipitate a solid, filtered with suction, and the filter cake was dried to obtain 10.33g, ASP-C-1, with a yield of 77.1% .

Embodiment 3

[0024] Dissolve 10.33g of ASP-C-1 in 25mL of DMF, add 500mL of 40% hydrobromic acid, heat up to 120°C, and react for 4 hours. TLC monitors that the raw material point disappears. After the reaction was completed, the heating was stopped. During the cooling and stirring process, an off-white solid gradually precipitated. After cooling down to room temperature, it was suction filtered, the filter cake was washed twice with methanol, and dried to obtain 8.52 g of an off-white solid, which was 1-[2-(2,4- Dimethylphenylsulfanyl)-phenyl]methylpiperazine (compound III), yield 80.1%.

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Abstract

The invention relates to a novel method for removing the methyl impurity in the preparation of asenapine. According to the method, asenapine maleate is taken as the raw material, then asenapine maleate is decomposed, the free alkalis and ethyl chloroformate are refluxed in toluene, and the product reacts with hydrobromic acid under reflux to obtain the methyl-free asenapine product. The method has the advantages of high yield and simple and convenient operation.

Description

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Claims

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Application Information

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Owner AVENTIS PHARMA HAINAN
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