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Piperazine-substituted benzothiophenes for treatment of mental disorders

A technology of substituents and representatives, applied in the field of new heterocyclic compounds, can solve problems such as not explicitly disclosing compounds

Active Publication Date: 2008-04-02
OTSUKA PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, WO2005 / 019215 A1 does not explicitly disclose the compounds of the present invention

Method used

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  • Piperazine-substituted benzothiophenes for treatment of mental disorders
  • Piperazine-substituted benzothiophenes for treatment of mental disorders
  • Piperazine-substituted benzothiophenes for treatment of mental disorders

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0358] Preparation of 7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butoxy]-1H-quinolin-2-one

[0359] 9.0g 7-(4-chlorobutoxy)-1H-quinolin-2-one, 10g 1-benzo[b]thiophen-4-yl-piperazine hydrochloride, 14g potassium carbonate, 6g sodium iodide and 90 ml of dimethylformamide were stirred at 80°C for 2 hours. Water was added to the reaction solution, and the precipitated crystals were separated by filtration. The crystals were dissolved in a mixed solvent of dichloromethane and methanol, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=100:3). Recrystallization in ethanol prepared 13.6 g of 7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butoxy]-1H-quinoline-2 in the form of a white powder -ketone.

[0360] The melting point is 183.5-184.5°C

[0361] 1 H-NMR (DMSO-d 6 )δppm:

[0362] 1.6-1.75(2H, m), 1.75-1.9(2H, m), 2.44(2H, t, J=7Hz), 2.5-2.8(4H, m), 2.9...

Embodiment 2

[0364] Preparation of 3-[2-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)ethoxy]-1H-quinolin-2-one

[0365] Using a method similar to that in Example 1, 3-[2-(4-benzo[b]thiophen-4-yl- piperazin-1-yl)ethoxy]-1H-quinolin-2-one.

[0366] white powder (chloroform)

[0367] The melting point is 201.9-204.5°C

[0368] 1 H-NMR (CDCl 3 )δppm:

[0369] 2.90-2.95(4H, m), 3.10(2H, t, J=5.9Hz), 3.23-3.27(4H, m), 4.30(2H, t, J=5.9Hz), 6.9O(1H, d, J =7.7Hz), 7.08(1H, s), 7.15-7.32(2H, m), 7.37-7.41(4H, m), 7.47-7.49(1H, m), 7.55(1H, d, J=8.1Hz) , 11.33(1H,br).

Embodiment 3

[0371] Preparation of 7-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-4-methyl-1H-quinolin-2-one

[0372] Using a method similar to that in Example 1, 7-[3-(4-benzo[b]thiophene was prepared from 7-(3-chloropropoxy)-4-methyl-1H-quinolin-2-one -4-yl-piperazin-1-yl)propoxy]-4-methyl-1H-quinolin-2-one.

[0373] Light brown powder (ethyl acetate)

[0374] The melting point is 202-208°C

[0375] 1 H-NMR (DMSO-d 6 )δppm:

[0376] 1.95-2.0(2H, m), 2.37(3H, s), 2.55(2H, t, J=7Hz), 2.6-2.7(4H, m), 3.05-3.2(4H, m), 4.09(2H, t , J=6.5Hz), 6.21(1H, bs), 6.8-6.85(2H, m), 6.90(1H, d, J=7.5Hz), 7.28(1H, dd, J=8Hz, 8Hz), 7.41( 1H, d, J=5.5Hz), 7.6-7.7(2H, m), 7.69(1H, d, J=5.5Hz), 11.41(1H, bs).

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Abstract

The present invention provides a heterocyclic compound represented by the general formula (1): The compound of the present invention has a wide treatment spectrum for mental disorders including central nervous system disorders, no side effects and high safety.

Description

technical field [0001] The present invention relates to a novel heterocyclic compound. Background technique [0002] Due to the different causes of schizophrenia and bipolar disorder, mood disorders and affective disorders, there is a need for a drug with multiple pharmacological effects in order to expand the therapeutic spectrum. [0003] A kind of quinolone derivative disclosed in WO2004 / 026864A1, its general formula is: [0004] [0005] (Wherein, A' represents -(CH 2 ) m CH 2 -, -(CH 2 ) m O- etc.; m represents an integer from 1 to 4; and R 4 C representing a hydrogen atom, which may be substituted by 1 to 3 fluorine atoms 1-4 alkyl, etc.). The derivative has D 2 Receptor antagonist activity and serotonin 2A (5-HT 2A ) receptor antagonist activity for the treatment of schizophrenia and other central nervous system diseases). [0006] However, it is not stated in WO2004 / 026864A1: the quinolone derivatives described in the document also have D 2 Receptor pa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/12A61K31/435A61P25/00
CPCC07D409/12C07D409/14C07D405/12A61K31/496A61P25/00A61P25/14A61P25/16A61P25/18A61P25/22A61P25/24A61P25/28A61P25/32A61K9/2054A61K9/2059C07D409/04
Inventor 山下博司松原淳大岛邦生黑田英明伊藤展明宫村伸清水聪田中达义高桥永
Owner OTSUKA PHARM CO LTD
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