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Novel piperazine salts as d3/d2 antagonists

A kind of technology of piperazine and solvate, applied in the field of novel piperazine salt as D3/D2 antagonist

Active Publication Date: 2010-03-24
RICHTER GEDEON NYRT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Another very important issue is the stability of the form of the active agent used

Method used

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  • Novel piperazine salts as d3/d2 antagonists
  • Novel piperazine salts as d3/d2 antagonists
  • Novel piperazine salts as d3/d2 antagonists

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] trans 4-{2-[4-(2,3-dichlorophenyl)-piperazin-1-yl]ethyl}-N,N-dimethylcarbamoyl-cyclohexylamine mesylate

[0038] 3.0g (0.007mol) of trans 4-{2-[4-(2,3-dichlorophenyl)-piperazin-1-yl]ethyl}-N,N-dimethylcarbamoyl - Cyclohexylamine and 0.46 ml (0.007 mol) of methanesulfonic acid are mixed in a mixture of 10 ml methanol and 80 ml acetonitrile. The reaction mixture was heated to boiling temperature, and the homogeneous solution obtained was concentrated to 25 ml by distillation. The resulting suspension was then stirred at a temperature of 0-5°C for 2 hours and the product was isolated by filtration.

[0039] In this way, 3.1 g of the title compound were obtained.

[0040] Yield: 84%.

[0041] Melting point: 225-229°C.

Embodiment 2

[0043] trans 4-{2-[4-(2,3-dichlorophenyl)-piperazin-1-yl]ethyl}-N,N-dimethylcarbamoyl-cyclohexylamine maleate

[0044] 3.0g (0.007mol) of trans 4-{2-[4-(2,3-dichlorophenyl-piperazin-1-yl]ethyl}-N,N-dimethylcarbamoyl- Cyclohexylamine and 0.83g (0.007mol) of maleic acid are suspended in 150ml acetone.The reaction mixture is heated to boiling temperature and stirred for half an hour, then distillation is concentrated to 25ml.Then the suspension obtained is at 0-5 The temperature was stirred for 2 hours at a temperature of °C, and the product was isolated by filtration.

[0045] In this way, 3.14 g of the title compound were obtained.

[0046] Yield: 82%.

[0047] Melting point: 173-177°C.

Embodiment 3

[0049] trans 4-{2-[4-(2,3-dichlorophenyl)-piperazin-1-yl]ethyl}-N,N-dimethylcarbamoyl-cyclohexylamine monohydrobromide Salt

[0050] 3.0g (0.007mol) of trans 4-{2-[4-(2,3-dichlorophenyl-piperazin-1-yl]ethyl}-N,N-dimethylcarbamoyl- Cyclohexylamine is suspended in the mixture of 12ml methyl alcohol and 38ml (1.5%) hydrobromic acid solution.Reaction mixture is heated to boiling point temperature and the homogeneous solution that obtains is cooled to the temperature of 0-5 ℃ and lasted 1 hour, then in After stirring at the same temperature for 2 hours, the product was isolated by filtration.

[0051] In this way, 3.0 g of the title compound were obtained.

[0052] Yield: 85%.

[0053] Melting point: 248-252°C.

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Abstract

The present invention relates to novel monohydrochloride, dihydrochloride, monohydrobromide, maleate and methanesulphonate salts of trans 4-(2-(4-(2,3-dichlorophenyl)-piperazine-1-yl)-ethyl)-N,N-dimethylcarbamoyl-cyclohexylamine and / or their hydrates and / or solvates. Moreover, the invention relates to the process for preparing the salts and their hydrates and / or solvates, to their use in the treatment and / or prevention of conditions which require modulation of dopamine receptor and to pharmaceutical compositions containing them.

Description

technical field [0001] The present invention relates to novel trans 4-{2-[4-(2,3-dichlorophenyl)-piperazin-1-yl]-ethyl}-N,N-dimethylcarbamoyl-cyclo Salts of hexylamine, processes for their preparation, and their use in the treatment and / or prevention of diseases requiring modulation of dopamine receptors, and pharmaceutical compositions containing them. Background technique [0002] Hungarian Patent Specification No.P0302451 discloses (thio)-carbamoyl-cyclohexane derivatives, which are D 3 / D 2 Preferred ligand for dopamine receptor subtypes. A specific compound disclosed therein is trans 4-{2-[4-(2,3-dichlorophenyl)-piperazin-1-yl]-ethyl}-N,N-dimethylaminomethanol Acyl-cyclohexylamines useful as dopamine receptor antagonists, especially as D 3 / D 2 Receptor antagonists and can be used in the treatment and prevention of pathological diseases requiring modulation of dopamine receptors. [0003] A general requirement for a pharmaceutical composition is that the active ag...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/04A61K31/495A61P25/00
CPCC07D241/04A61P1/08A61P15/10A61P25/00A61P25/16A61P25/18A61P25/20A61P25/22A61P25/24A61P25/28A61P25/30A61P43/00A61K31/495C07B2200/13
Inventor E·阿高内琼戈尔L·齐布拉F·塞伯克G·多马尼I·格赖纳
Owner RICHTER GEDEON NYRT
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