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5-HT2A receptor inhibitor, preparation method and applications thereof

A technology that accepts salts and stereoisomers, applied in the field of drug development, can solve the problems of unavoidable side effects of extrapyramidal tract and weight gain

Active Publication Date: 2019-01-01
SHANGHAI HANSOH BIOMEDICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the second-generation antipsychotic drugs still have D2 receptor inhibitory activity, extrapyramidal side effects are inevitable, and these drugs have side effects of weight gain in varying degrees

Method used

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  • 5-HT2A receptor inhibitor, preparation method and applications thereof
  • 5-HT2A receptor inhibitor, preparation method and applications thereof
  • 5-HT2A receptor inhibitor, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0145] 1-(4-fluorobenzyl)-3-(4-isobutoxybenzyl)-1-((1-isopropylazetidin-3-yl)methyl)urea

[0146]

[0147] The first step: the synthesis of benzyl (1-isopropyl azetidin-3-yl) methyl carbamate

[0148]

[0149] At room temperature, dissolve benzyl (azetidin-3-ylmethyl) carbamate (0.4g, 1.82mmol) and acetone (0.16g, 2.72mmol) in DCE (10mL), stir for one hour, then add in portions Sodium triacetylborohydride (0.58g, 102.9mmol), stirred at room temperature for 18 hours, then washed with CH 2 Cl 2 (50mL), diluted with diatomaceous earth, the organic phase was washed with water (10mL) and saturated brine (15mL) successively, and dried with anhydrous sodium sulfate, column chromatography after concentration gave compound benzyl (1-isopropylacridine Butidin-3-yl)methylcarbamate (0.21 g, 44%).

[0150] MS m / z(ESI):263.2[M+H] + .

[0151] The second step: the synthesis of (1-isopropylazetidin-3-yl)methanamine

[0152]

[0153] To a solution of benzyl(1-isopropylazetidin-3...

Embodiment 2

[0165] 1-((1-ethylazetidin-3-yl)methyl)-1-(4-fluorobenzyl)-3-(4-isobutoxybenzyl)urea

[0166]

[0167] The preparation method of 1-((1-ethylazetidin-3-yl)methyl)-1-(4-fluorobenzyl)-3-(4-isobutoxybenzyl)urea refers to the implementation example 1.

[0168] 1 H NMR (400MHz, CDCl 3 )δ7.24-7.08(m,4H),7.03-6.94(m,2H),6.84-6.74(m,2H),4.43(s,2H),4.34(d,J=4.34Hz,2H),3.84 (m,2H),3.69(m,6H),3.04-2.84(m,3H),2.13-1.96(m,1H),1.24-1.15(t,J=14.5Hz,3H),1.01(d,J =6.7Hz,6H);

[0169] MS m / z(ESI):428.2[M+H] + .

Embodiment 3

[0171] 1-(4-fluorobenzyl)-3-(4-isobutoxybenzyl)-1-((1-methylazetidin-3-yl)methyl)urea

[0172]

[0173] The preparation method of 1-(4-fluorobenzyl)-3-(4-isobutoxybenzyl)-1-((1-methylazetidin-3-yl)methyl)urea refers to the implementation example 1.

[0174] 1 H NMR (400MHz, CDCl 3 )δ7.18-7.13(m,4H),7.03-6.96(m,2H),6.85-6.79(m,2H),5.30-5.19(m,1H),4.44(s,2H),4.34(d, J=5.4Hz, 2H), 3.69(d, J=6.6Hz, 2H), 3.50(d, J=7.7Hz, 2H), 3.29-3.24(m, 2H), 3.02-2.96(m, 2H), 2.65-2.57(m,1H),2.28(s,3H),2.09-2.03(m,1H),1.01(d,J=6.7Hz,6H);

[0175] MS m / z(ESI):414.3[M+H] + .

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PUM

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Abstract

The invention relates to a 5-HT2A receptor inhibitor, a preparation method and applications thereof, particularly to a compound represented by a general formula (I), and a preparation method thereof,a pharmaceutical composition containing the compound, and uses of the compound as a 5-HT2A receptor inhibitor in preparation of related drugs for prevention and / or treatment of psychogenic diseases and neurodegenerative diseases, wherein each substituent in the formula (I) is defined in the specification. The formula (I) is defined in the specification.

Description

technical field [0001] The invention belongs to the field of drug development, in particular to a selective 5-HT 2A Receptor inhibitor and its preparation method and application. Background technique [0002] Schizophrenia is one of the most prevalent mental illnesses, with an incidence of about 1% worldwide. In our country, the prevalence rate is 7.11‰ in urban areas and 4.26‰ in rural areas. Cities are significantly higher than rural areas. The prevalence is roughly equal in both sexes. The disease mostly occurs in young adults, the most common in 15 to 35 years old, 50% of the patients are 20 to 30 years old, and it is rare before the age of 10 (children's schizophrenia) and after 40 to 50 years of age (late onset schizophrenia). disease). Most epidemiological data in my country suggest that the prevalence rate of females is higher than that of males. The gender difference is more obvious in the age group over 35 years old; the prevalence rate in urban areas is high...

Claims

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Application Information

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IPC IPC(8): C07D205/04C07D207/14C07D207/09C07D207/10C07D211/26C07D211/58C07D221/20C07D405/12A61K31/397A61K31/40A61K31/445A61K31/4525A61K31/438A61P25/18A61P25/24A61P25/22A61P25/28A61P25/20A61P25/06A61P25/00A61P9/10A61P29/00A61P25/16A61P25/14
CPCA61P9/10A61P25/00A61P25/06A61P25/14A61P25/16A61P25/18A61P25/20A61P25/22A61P25/24A61P25/28A61P29/00C07D205/04C07D207/09C07D207/10C07D207/14C07D211/26C07D211/58C07D221/20C07D405/12
Inventor 高鹏修文华王少宝谭松良孙广俊张福军包如迪
Owner SHANGHAI HANSOH BIOMEDICAL