Amide compound for prevention and treatment of mental disorders

A compound and solvate technology, which is applied in the field of amide compounds for the prevention and treatment of mental disorders, can solve problems such as slow onset of action, onset of toxic and side effects, and effects on post-synaptic membrane function

Active Publication Date: 2018-12-18
SHAOXING ZEROIN BIOMEDICINES CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the research and development and clinical application of antidepressant drugs have made great progress in the past few decades, these drugs will affect the function of receptors on the postsynaptic membrane to varying degrees, thus showing obvious toxic side effects And defects such as slow onset (Vaswani, M., Linda, F.K.&Ramesh, S.Role ofselective serotonin reuptake inhibitors in psychiatric disorders: a comprehensive review.Prog Neuropsychopharmacol Biol Psychiatry27,85-102(2003

Method used

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  • Amide compound for prevention and treatment of mental disorders
  • Amide compound for prevention and treatment of mental disorders
  • Amide compound for prevention and treatment of mental disorders

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0128] Example 1 2-(2-((2-(3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl)amino)phenyl)acetic acid Preparation of methyl ester (compound 1)

[0129]

[0130] Step 1. 2-Bromo-1-(3,4-dihydroisoquinolin-2(1H)-yl)ethanone

[0131] Dissolve tetrahydroisoquinoline (5.0g, 37.54mmol), N,N-dimethylaniline (5.3mL, 41.29mmol) in dichloromethane (80mL), bromoacetyl bromide (3.6mL, 41.29mmol) in Add dropwise to the reaction solution at 0-5°C. After the dropwise addition was completed, the stirring was continued for 30 min, and the reaction was monitored by TLC to end. The reaction solution was poured into ice water, the organic phase was separated, and the aqueous phase was extracted with dichloromethane. The combined organic phases were washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by silica gel column chromatography (petroleum ether / ethyl acetate=7 / 1) to obtain 2-bromo-1-(3,4-dihydroisoquinolin-2...

Embodiment 2-15

[0135] Example 2-15 Synthesized Example 2-15 with reference to the method of Example 1

[0136]

[0137]

[0138]

Embodiment 16

[0139] Example 16 2-(3-(N-(2-(3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl)methylsulfonamide base) phenyl) methyl acetate

[0140]

[0141] Step 1. Methyl 2-(3-(methylsulfonylamino)phenyl)acetate

[0142] 2-(3-Aminophenyl)methyl acetate (300mg, 1.82mmol), pyridine (160mg, 2.00mmol) were dissolved in dichloromethane (10mL), and methylsulfonyl chloride (230mg, 2.00 mmol) was slowly added dropwise into the reaction solution. After 1 hour, TLC monitored the completion of the reaction. The reaction solution was poured into ice water, the organic phase was separated, the aqueous phase was extracted with dichloromethane, the combined organic phase was washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain 2-(3-(methylsulfonylamino )phenyl)methyl acetate (450 mg, crude) as a pale yellow oil.

[0143] Step 2. 2-(3-(N-(2-(3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl)methylsulfonylamino)benzene base) methyl acetate

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Abstract

The present invention relates to an amide compound for prevention and treatment of mental disorders, which is shown as a formula (I), a pharmaceutically acceptable salt thereof, a prodrug thereof, a solvate thereof, a deuterated substance or a stereoisomer thereof. Wherein R1, R2, R3, R4, R5, Ar1, Ar2, p and q are as defined in the specification. The invention also relates to a preparation methodof the amide compound, a pharmaceutical composition and a pharmaceutical preparation containing the amide compound, and an application of the compound in preparation of a drug for prevention or treatment of mental disorders such as depression, depression and anxiety, and schizophrenia.

Description

1. Technical field [0001] The present invention belongs to the technical field of medicine, and relates to amide compounds, pharmaceutically acceptable salts, prodrugs, solvates, deuteriums, or stereoisomers thereof for the prevention and treatment of mental disorders. The present invention also relates to the The preparation method of the compound, the pharmaceutical composition and pharmaceutical preparation containing the compound, and the application of the compound in the medicine for preventing or treating depression, depression and anxiety, schizophrenia and other mental disorders in mammals. 2. Background technology [0002] Depression is a common mental illness. Depressed patients often present with depressed mood, loss of interest or enjoyment, feelings of guilt or low self-esteem, sleep and appetite disturbances, physical fatigue, and difficulty concentrating. Depression can be chronic or recurring frequently, seriously affecting an individual's daily life. When ...

Claims

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Application Information

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IPC IPC(8): C07D217/06C07D209/44C07D401/12C07D405/12C07D413/12C07D471/04A61K31/472A61K31/4725A61K31/4375A61K31/4035A61K31/5377A61K31/496A61K45/06A61P25/18A61P25/22A61P25/24
CPCA61K45/06A61P25/18A61P25/22A61P25/24C07D209/44C07D217/06C07D401/12C07D405/12C07D413/12C07D471/04
Inventor 阳怀宇
Owner SHAOXING ZEROIN BIOMEDICINES CO LTD
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