(4-piperidnyl)-1H-2-benzopyran derivatives useful as antipsychotic agents

A technology of benzopyran and piperidinyl, applied in the field of intermediates for the preparation of new compounds

Inactive Publication Date: 2000-03-08
AVENTISUB LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Of course, many of these drugs have undesirable side effects (eg, extra

Method used

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Experimental program
Comparison scheme
Effect test

Embodiment 1A

[0065] The abbreviations used in this paper have the following meanings: THF means tetrahydrofuran, CH 2 Cl 2 means dichloromethane, TLC means thin layer chromatography, EtOAC means ethyl acetate, Et 2 NH means diethylamine, IR means infrared spectrum, NMR means nuclear magnetic resonance spectrum, CHCl 3 means chloroform, CDCL 3 means deuterated chloroform, MS means mass spectrum, HCl means hydrochloric acid, EtOH means ethanol, NaBH 4 means sodium borohydride, NaOH means sodium hydroxide, mp means melting point, C means Celsius, MeOH means methanol, BF 3 O(Et) 2 Means boron trifluoride diethyl ether, Na 2 CO 3 means sodium carbonate, h means hour, BBr 3 Means boron tribromide, LAH means lithium aluminum hydride. Example 1A Intermediate: N-[2-(2,3-dimethoxyphenyl)-1-(4-pyridyl)vinyl]formamide

[0066] A solution of 4-(aminomethyl)pyridine (54.1 g, 0.5 mol) and ethyl formate (44.4 ml) was refluxed for 2 hours, then allowed to stand at room temperature for 16 hours. ...

Embodiment 2B

[0072] To a stirred dichloromethane solution (15 ml) of piperidinol (1.8 g, 6.8 mmol) from Example 1D was added Et under nitrogen. 3N (2.8ml, 20.4mmol). The reaction was cooled to about 5°C (ice bath) and trifluoroacetic anhydride (3.1 g, 2.1 ml, 15 mmol) was added dropwise. After 1.5 hours at room temperature, the reaction was concentrated to a yellow oil. It was diluted with water, with Et 2 O was subjected to extractive treatment to obtain a yellow oil. Example 2B Intermediate: 4-[2-(2,3-Dimethoxyphenyl)-1-hydroxyethyl]piperidine trifluoroacetamide

[0073] 4-[2-(2,3-dimethoxyphenyl)-1-(trifluoroacetoxy)ethyl]piperidine trifluoroacetamide compound (2.3g, 6.0mmol), K 2 CO 3 (crushed, 1.0 g, 6.6 mmol) and anhydrous methanol (15 ml) were stirred at room temperature for 3 hours. The reaction was filtered and the filtrate was concentrated to give 2.3 g of a thick yellow oil. The oil uses Et 2 O Trituration (obtained white solid). The solid was filtered and the filtrat...

Embodiment 18B

[0107] Example 18B Intermediate: spiro[(1,3-benzodioxole)-2,1-cyclohexane

[0108] A mixture of 1,2-dihydroxybenzene (2.72 mol), cyclohexanone (2.72 mol), toluene (2.3 L) and p-TsOH (0.55 g) was refluxed under nitrogen for 18 hours. A total of 48ml of water was collected with a Dean Stark trap. After cooling, the mixture was neutralized with 5% NaOH, washed with water, dried (magnesium sulfate) and filtered. The filtrate was concentrated to give a crude golden oil which solidified on standing. The crude solid was recrystallized from petroleum ether (400ml, boiling range 35-60°C) to give spirol ketal. Example 19 Intermediate: 2-(1-Benzyl-4-piperidinyl)-1-spiro(1,3-benzodioxole-2,1’-cyclohexane)-2-ethanol

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Abstract

The present invention comprises (4-Piperidinyl)-1H-2-Benzopyran derivatives useful as antipsychotic agents, their intermediates, pharmaceutical compositions and methods of making these compounds. These compounds are useful in treating psychosis.

Description

field of invention [0001] The present invention relates to intermediates useful in the preparation of novel compounds, novel compounds, methods of treating psychosis by administering the novel compounds, and processes for the preparation of these compounds. Background of the invention [0002] Psychosis is an illness that dramatically interferes with the ability to live a normal life. Conceptually, it is a loss of ego boundaries or a marked impairment of reality testing. The term psychosis includes: schizophrenia, schizophrenia-like disorder, schizoaffective disorder, delusional disorder, transient disorder, shared disorder, psychosis due to a general medical condition Disorder, substance-induced mental disorder, and mental disorder not otherwise specified, as defined by the American Psychiatric Association in the Diagnostic and Statistical Manual of Psychiatric Disorders, Fourth Edition, Washington, D.C., USA, 1994, which is incorporated herein by reference. [0003] Schi...

Claims

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Application Information

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IPC IPC(8): A61K31/453A61K31/4535A61P25/18C07D405/04C07D405/14C07D409/14C07D413/14C07D417/14C07D493/04C07D493/10
CPCC07D493/10C07D405/04A61P25/00A61P25/18A61K31/453
Inventor J·T·斯特拉普克泽乌斯基K·J·伯尔缔尤S·L·帕乌莱克
Owner AVENTISUB LLC
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