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Novel 5-hydroxytryptamine reuptake inhibitor compounds as well as preparation method and applications thereof in medicine

A serotonin reuptake and inhibitor technology, applied in the field of medicinal chemistry, can solve problems such as increased severe arrhythmia, extrapyramidal side effects, increased serum prolactin levels, etc., and achieve improved oral utilization and extended half-life Effect

Inactive Publication Date: 2018-01-09
HC SYNTHETIC PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Risperidone at high doses causes increased serum prolactin levels and extrapyramidal side effects
Ziprasidone increases the risk of severe arrhythmia due to cardio-QTC prolongation
In addition, clozapine induces agranulocytosis, so its clinical application is severely limited (van Kammen, D.P. (compiled under the supervision of Murasaki Mitsuroh), "RINSHOUSEISHINYAKURI", Vol. 4, pp. 483-492 (2001))

Method used

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  • Novel 5-hydroxytryptamine reuptake inhibitor compounds as well as preparation method and applications thereof in medicine
  • Novel 5-hydroxytryptamine reuptake inhibitor compounds as well as preparation method and applications thereof in medicine
  • Novel 5-hydroxytryptamine reuptake inhibitor compounds as well as preparation method and applications thereof in medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: Preparation of (S)-1-(3-fluorophenyl)-N,N-dimethyl-3-(naphthalene-4-yloxy)propan-1-amine (compound I-1)

[0037]

[0038] Compound I-1

[0039] Take (S)-1-(3-fluorophenyl)-3-(naphthalene-4-yloxy)propan-1-amine 10g, add it into acetonitrile and stir to dissolve. Then 0.48 g of dimethyl sulfate was added. Heat to reflux for 6 hours. Add 1% activated carbon in total volume to the reaction liquid, reflux for decolorization for 15 min, and filter. The filtrate was concentrated to dryness under reduced pressure, and the residue was separated by HPLC to obtain 3.3 g of compound I-1.

Embodiment 2

[0040] Example 2: (S)-N,N-Dimethyl-3-(naphthalen-4-yloxy)-1-(3-(trifluoromethyl)phenyl)propan-1-amine (Compound I -2) Preparation

[0041]

[0042] Compound I-2

[0043] Take 10.0 g of (S)-3-(naphthalene-4-yloxy)-1-(3-(trifluoromethyl)phenyl)propan-1-amine, add it into acetonitrile and stir to dissolve. Then 0.48 g of dimethyl sulfate was added. Heat to reflux for 6 hours. Add 1% activated carbon in total volume to the reaction liquid, reflux for decolorization for 15 min, and filter. The filtrate was concentrated to dryness under reduced pressure, and the residue was separated by HPLC to obtain compound I-24.5g.

Embodiment 3

[0044] Embodiment 3: Preparation of (S)-3-(1-fluoronaphthalen-5-yloxy)-N,N-dimethyl-1-phenylpropane-1-amine (compound I-7)

[0045]

[0046] Compound I-7

[0047] Prepared according to the method of Example 1, except that (S)-1-(3-fluorophenyl)-3-(naphthalene-4-yloxy)propan-1-amine is replaced by (S)-3- (1-fluoronaphthalen-5-yloxy)-1-phenylpropan-1-amine.

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PUM

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Abstract

The invention relates to novel 5-hydroxytryptamine reuptake inhibitor compounds as well as a preparation method and applications thereof in medicine, and concretely relates to the novel 5-hydroxytryptamine reuptake inhibitor compounds shown in a general formula (I), the preparation method thereof, pharmaceutical compositions containing the compounds, and the applications of the compounds as therapeutic agents, especially in preparation of drugs used for treatment or prevention of diseases associated with monoamine transporter function regulation, wherein definition of each substituent in the general formula (I) is identical to definition in the claims. (The structures of the compounds are shown in the description.)

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to novel serotonin reuptake inhibitor compounds, a preparation method, a pharmaceutical composition containing the compound, and preparations for treating or preventing diseases related to monoamine transporter function regulation by such compounds Uses in medicine. Background technique [0002] Due to many reasons such as social pressure, unemployment, illness and poverty, the number of people suffering from mood disorders such as major depressive disorder and exhibiting various depressive symptoms is increasing every year. Depression is a serious social problem worldwide. For example, in Japan, the incidence of depression, including major depressive disorder, is 5% or more among the generation older than 65 years old. In this population, some depressive disorders are associated with mental disturbances, which represent diseases of aging associated with dementia and neurosis. Ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/48C07C217/64C07C233/18A61K31/133A61K31/165A61P9/12A61P25/24A61P25/22A61P25/00A61P15/00A61P15/10A61P3/04A61P25/30A61P25/06A61P25/04A61P25/28A61P25/16A61P25/18A61P13/00A61P21/00A61P1/00A61P5/00
Inventor 陆华龙
Owner HC SYNTHETIC PHARMA CO LTD
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