Heterocyclic compound, preparation method therefor and use of heterocyclic compound

A technology of heterocyclic compounds and heterocyclic groups, which is applied in the application field of preparing medicines for diseases of the central nervous system, and can solve problems such as side effects

Inactive Publication Date: 2016-10-05
SUZHOU VIGONVITA LIFE SCIENCES CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, pure D 2 Antagonist or D 2 Antagonist / 5-HT 2A Antagonists still have varying degrees of side effects

Method used

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  • Heterocyclic compound, preparation method therefor and use of heterocyclic compound
  • Heterocyclic compound, preparation method therefor and use of heterocyclic compound
  • Heterocyclic compound, preparation method therefor and use of heterocyclic compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0140] Preparation Example 1 Preparation of 1-(2-fluorobenzothiophen-4-yl)piperazine

[0141]

[0142] step 1:

[0143] Dissolve 2-chloro-6-fluorobenzaldehyde 1-a (500mg, 3.15mmol), N-tert-butoxycarbonylpiperazine (646mg, 3.47mmol) into N,N-dimethylformamide (5ml), Under nitrogen protection, potassium carbonate (2.18g, 15.77mmol) was added at room temperature, the mixture was stirred at 80°C for 4 hours, cooled and filtered, water (20ml) was added, extracted with ethyl acetate (5ml×3), and 1N hydrochloric acid (3ml) Washing, washing with saturated aqueous sodium bicarbonate, drying over anhydrous sodium sulfate, concentration to obtain a solid, beating with petroleum ether (50ml) for 1 hour, and filtering to obtain a light yellow solid 1-b (1.0g, yield 90%). 1 H-NMR (300Hz, DMSO-d 6 ): δppm10.19(s,1H),7.52(t,1H),7.18(d,2H),3.46(t,4H),2.94(t,4H),1.39(s,9H).

[0144] Step 2:

[0145] in N 2 Under protection, compound 1-b (5g, 15.3mmol), ethyl thioglycolate (1.8g, 15.3mmo...

preparation example 2

[0154] Preparation Example 2 Preparation of 1-(2-chlorobenzothiophen-4-yl)piperazine

[0155]

[0156] step 1:

[0157] Take compound 1-e (900mg, 2.83mmol) in a dry three-necked flask, add tetrahydrofuran (3ml) to dissolve it under nitrogen protection, cool down to -78°C, inject 2.5M n-butyllithium n-hexane solution (1.47ml , 3.67mmol), and maintained at -78°C for 3 hours. N-chlorosuccinimide (677mg, 5.09mmol) was dissolved in tetrahydrofuran (3ml), slowly injected into the reaction system, moved to room temperature and stirred overnight after half an hour. Add saturated ammonium chloride solution to quench the reaction, add water, extract with dichloromethane, wash the organic phase with saturated brine, dry over anhydrous sodium sulfate, concentrate, and column chromatography gives oil 2-a (540mg, yield 54% ).

[0158] Step 2:

[0159] Take compound 2-a (540mg, 1.53mmol), add dichloromethane (1ml) and trifluoroacetic acid (1ml), and stir at room temperature for 3 hour...

preparation example 3

[0160] Preparation Example 3 Preparation of 1-(2,3-dihydrobenzothiophen-4-yl)piperazine hydrochloride

[0161]

[0162] step 1:

[0163] Lithium aluminum hydride (4.6g, 121mmol) was added to a flask containing dry tetrahydrofuran (20ml), and a solution of compound 3-a (10g, 53.2mmol) dissolved in tetrahydrofuran (100ml) was added dropwise to To the above reaction solution, after the dropwise addition, stir at room temperature for 20 minutes, then heat to reflux, stop the reaction after 3 hours, slowly add sodium sulfate decahydrate until the bubbles are no longer released, filter with suction, dry the filtrate, concentrate and perform column chromatography The product 3-b (7.8 g, yield 85%) was obtained.

[0164] Step 2:

[0165] Compound 3-b (6.7g, 38.5mmol), triethylamine (4.66g, 46.2mmol) and dichloromethane (80ml) were added to the flask, and at room temperature, p-toluenesulfonyl chloride (7.34g, 38.5mmol) Dissolved in dichloromethane (20ml) and added dropwise to th...

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PUM

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Abstract

The invention provides a heterocyclic compound represented by a general formula (I) shown in the description, a stereoisomer or pharmaceutically acceptable salt thereof, a pharmaceutical composition of the heterocyclic compound or the stereoisomer or pharmaceutically acceptable salt thereof and an application of the heterocyclic compound or the stereoisomer or pharmaceutically acceptable salt thereof in preparation of drugs for preventing and / or treating central nervous system diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry. Specifically, the present invention relates to a class of heterocyclic compounds represented by general formula (I), their stereoisomers or pharmaceutically acceptable salts thereof, their preparation methods, pharmaceutical compositions and their use in the preparation of central nervous system diseases application in medicine. Background technique [0002] Mental illness is mainly a group of nervous system diseases mainly manifested in behavioral and mental activity disorders. barriers of varying degrees. [0003] Due to the complexity of the central nervous system, existing antipsychotic drugs still have their own limitations. For example, clinically used drugs for the treatment of major depressive disorder (MDD) and anxiety have slow onset and poor efficacy; existing anti-schizophrenia drugs still cannot improve negative symptoms and cognitive impairment, or have extrapyramidal reactions...

Claims

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Application Information

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IPC IPC(8): C07D409/12C07D409/14A61P25/24A61P25/22A61P25/18A61P25/28A61P25/16A61P25/14
Inventor 田广辉柳永建尹敬敬
Owner SUZHOU VIGONVITA LIFE SCIENCES CO LTD
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