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New compound Malabemide, preparation method and uses thereof

A molarabemide and compound technology, which is applied in the field of new compound morapemide, can solve the problems of difficulty in purification, toxicity, low yield and the like, and achieves the effects of simple operation, high yield and good product purity

Pending Publication Date: 2018-10-16
CHONGQING NORMAL UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] It has been proved by pharmaceutical tests that moclobemide has the same activity as moclobemide, but the synthetic route of moclobemide involves toxic intermediates, and there are disadvantages such as low yield and difficult purification.

Method used

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  • New compound Malabemide, preparation method and uses thereof
  • New compound Malabemide, preparation method and uses thereof
  • New compound Malabemide, preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The synthesis of embodiment 1 2-bromoethylamine hydrobromide (b)

[0026] At 0-10°C, add ethanolamine dropwise to 40% hydrobromic acid with a molar ratio of 1:9, stir magnetically, control the temperature of the reaction system at no more than 10°C, and control the time of dropping ethanolamine at 25-30min. After the dropwise addition, the solvent xylene was added to the reaction system, and the temperature was raised to separate the water for 12 hours, and the temperature of the water separation was 135-145°C. After the water separation is completed, cool, filter to remove the solvent, and wash the filter residue three times with cold acetone to obtain the white crystalline product 2-bromoethylamine hydrobromide. The yield is 99%, the purity is 99.5%, and the melting point is 172-174°C.

Embodiment 2

[0027] Example 2 Synthesis of 5-chloro-2-pyridinecarbonyl chloride (e)

[0028] At 0-10°C, first add 5-chloro-2-pyridinecarboxylic acid into the solvent dichloromethane, stir evenly with a magnetic force, then add thionyl chloride dropwise, the molar ratio is 1:4, and the temperature of the reaction system is controlled at The temperature does not exceed 10°C, and the time for dropping thionyl chloride is controlled within 15-20 minutes. After the dropwise addition, heat up and reflux for 7-8 hours. The reflux temperature is 40-45°C. After the reflux is completed, the solvent dichloromethane is removed under normal pressure, cooled, and dried in vacuum to obtain white crystals of 5-chloro-2-pyridinecarbonyl chloride . The yield is 92%, the purity is 99.4%, and the melting point is 218-220°C.

Embodiment 3

[0029] Example 3 Synthesis of 5-chloro-N-(2-bromoethyl)-2-pyridinecarboxamide (f)

[0030] First add 2-bromoethylamine hydrobromide into distilled water, and stir to dissolve with magnetic force. The sodium hydroxide solution was added dropwise to neutralize the reaction, and after the dropwise addition was completed, the solvent toluene was added, and the temperature was raised to separate water. After the water separation is completed, cool, filter, and collect the filtrate. Then add 5-chloro-2-pyridinecarbonyl chloride to the filtrate, the molar ratio is 2:1, heat up and reflux for 8-10 hours, and the reflux temperature is 115-125°C. After the reaction is completed, cool, filter with suction, and recrystallize from toluene to obtain 5-chloro-N-(2-bromoethyl)-2-pyridinecarboxamide as white crystals. The yield is 93%, the purity is 99.5%, and the melting point is 201-203°C.

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Abstract

The invention discloses a new compound Malabemide with a molecule formula represented by a formula h, a preparation method and pharmaceutical applications thereof, wherein ethanolamine and 5-chloro-2-pyridinecarboxylic acid are used as starting raw materials, corresponding intermediates 2-bromoethylamine hydrobromide and 5-chloro-2-pyridinecarbonyl chloride are respectively synthesized, and are subjected to a reaction to generate 5-chloro-N-(2-bromoethyl)-2-pyridinecarboxamide, and the 5-chloro-N-(2-bromoethyl)-2-pyridinecarboxamide and morpholine are subjected to condensation to generate Malabemide h. According to the present invention, the preparation method has characteristics of easily available raw materials, simple operation, good product purity and high yield, and is suitable for industrial production. The formula h is defined in the specification.

Description

technical field [0001] The present invention relates to a new compound morabemide, its preparation method and application. Background technique [0002] The chemical name of morabemide is 5-chloro-N-[2-(4-morpholinyl)ethyl]-2-pyridinecarboxamide, and its molecular formula is C 12 h 17 ClN 3 o 2 , with a relative molecular weight of 268.72 and a melting point of 162-164°C, it is a white crystal. Morabemide is a newly designed and synthesized new compound, and there is no related report at home and abroad. [0003] The molecular design of morabemide uses moclobemide and lazabemide as the lead compounds, and adopts the principle of bioelectronic isosteres and combination principles to design a new compound. Replace the carbon atom in the 2-position on the benzene ring of moclobemide with a nitrogen atom by using the bioisosteric principle to design moclobemide; or use the combination principle to combine the morpholine group of moclobemide with the The pyridine groups of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/81A61K31/5377A61P25/24
CPCC07D213/81A61P25/24
Inventor 杨善彬周石洋杨大坚
Owner CHONGQING NORMAL UNIVERSITY
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