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Heterocyclic acetic acid amide compound

A compound and pharmaceutical composition technology, applied in the field of heterocyclic acetamide compounds, can solve problems such as no specific disclosed compounds

Active Publication Date: 2015-12-02
ASTELLAS PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the compound of the invention is not specifically disclosed

Method used

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  • Heterocyclic acetic acid amide compound
  • Heterocyclic acetic acid amide compound
  • Heterocyclic acetic acid amide compound

Examples

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Effect test

Embodiment

[0240] Hereinafter, the method for producing the compound of formula (I) will be described in more detail based on examples. In addition, the present invention is not limited to the compounds described in the following Examples. In addition, the production method of the raw material compound is shown in the production example. In addition, the production method of the compound of formula (I) is not limited to the production method shown in the following specific examples, and the compound of formula (I) can also be produced by a combination of these production methods or by a method obvious to those skilled in the art .

[0241] The following abbreviations are sometimes used in Examples, Production Examples, and Tables described below.

[0242] PEx=production example number, Ex=example number, Syn=example number produced by the same method, PSyn=production example number produced by the same method, Str=structural formula, DAT=physicochemical data, APCI+=APCI- m / z value in ...

manufacture example 1

[0248] Under argon atmosphere, to 5-chloro-1,3-benzo To a mixture of oxazol-2(3H)-one (50.0 g) and acetone (750 mL) was added K at room temperature 2 CO 3 (61.1g) and tert-butyl bromoacetate (52.3mL), heated to reflux for 1.5 hours. The reaction mixture was filtered hot, washing with acetone. The filtrate and washings were combined and concentrated under reduced pressure. The resulting solid was stirred in a mixed solvent of Hex / EtOAc (6 / 1) and recovered by filtration, and further stirred in water and recovered by filtration to obtain (5-chloro-2-oxo-1,3-benzo tert-butyl azol-3(2H)-yl)acetate (81.1 g).

manufacture example 2

[0250] In (5-chloro-2-oxo-1,3-benzo TFA (67.4 mL) was added to a mixture of tert-butyl azol-3(2H)-acetate (50 g) and dichloromethane (250 mL), followed by stirring at room temperature overnight. After the reaction mixture was concentrated under reduced pressure, water was added to the residue. After the solid produced was recovered by filtration, it was washed with water to obtain (5-chloro-2-oxo-1,3-benzo Azol-3(2H)-yl)acetic acid (38.5 g).

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Abstract

[Problem] A compound which is useful as a dopamine D1 receptor positive allosteric modulator (D1 PAM) is provided. [Means for Solution] The present inventors have studied a compound which has a dopamine D1 receptor positive allosteric modulating activity and is useful as an active ingredient of a pharmaceutical composition for preventing and / or treating cognitive impairment, negative symptoms of schizophrenia, Parkinson's disease, Alzheimer's disease, Huntington's disease, drug addictions, or the like, and they have thus found that a heterocyclic acetamide compound has a dopamine D1 receptor positive allosteric modulating activity, thereby completing the present invention. The heterocyclic acetamide compound of the present invention has a dopamine D1 receptor positive allosteric modulating activity and can be used as an agent for preventing and / or treating cognitive impairment, negative symptoms of schizophrenia, Parkinson's disease, Alzheimer's disease, Huntington's disease, drug addictions, or the like.

Description

technical field [0001] The present invention relates to a pharmaceutical composition, in particular to a medicine for the prevention and / or treatment of cognitive dysfunction, negative symptoms of schizophrenia, Parkinson's disease, Alzheimer's disease, Huntington's disease, and drug dependence, etc. The active ingredient of the composition is a heterocyclic acetamide compound. Background technique [0002] Dopamine receptors are a type of G protein-coupled receptors present in the central nervous system. Dopamine receptors can be divided into the dopamine D1-like receptor family and the dopamine D2-like receptor family. Dopamine D1 and D5 receptors in dopamine receptors belong to the D1 receptor family. In addition, dopamine D2, D3, and D4 receptors belong to the dopamine D2-like receptor family. [0003] It has been reported that the dopamine D1 receptor exerts multiple functions: coupling with the promoting G protein, namely Gas, activates adenylate cyclase, increases ...

Claims

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Application Information

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IPC IPC(8): C07D413/12C07D403/12C07D417/12A61K31/423A61K31/428A61K31/498A61P25/14A61P25/16A61P25/28A61P25/36
CPCC07D413/12C07D417/12A61P25/00A61P25/14A61P25/16A61P25/18A61P25/28A61P25/36
Inventor 白木良太户部贵彦川上晋平森友博幸大宫诚
Owner ASTELLAS PHARMA INC
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