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N-(3,5-dimethyladamantan-1-yl)-n'-substituted phenylurea compounds and their preparation methods and uses

A technology of dimethyladamantane and dimethylphenyl, used in pharmaceutical compositions as active ingredients, in the treatment of Alzheimer's disease, in the field of N--N'-substituted phenylurea compounds, Achieve the effect of good independence, simple operation and stable reaction process

Active Publication Date: 2020-02-07
沈阳海诺威医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there is no report on the treatment of Alzheimer's disease with N-(3,5-dimethyladamantan-1-yl)-N'-substituted phenylurea compounds

Method used

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  • N-(3,5-dimethyladamantan-1-yl)-n'-substituted phenylurea compounds and their preparation methods and uses
  • N-(3,5-dimethyladamantan-1-yl)-n'-substituted phenylurea compounds and their preparation methods and uses
  • N-(3,5-dimethyladamantan-1-yl)-n'-substituted phenylurea compounds and their preparation methods and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1: Synthesis of N-(3,5-dimethyladamantan-1-yl)-piperidine-1-carboxamide (ZCY-01):

[0057] Add d (2g, 0.0067mol), piperidine (1.0g), 4-dimethylaminopyridine (0.1g), ethanol (10ml) to a 50ml three-necked flask, reflux for 8 hours, TLC monitors that the reaction of the raw materials is complete, and the column layer Analysis gave 0.6 g of white solid, yield 29.0%. mp136.6-137.5℃; 1 H-NMR (400MHz, DMSO-d 6 )δ0.80(s,6H,CH 3 ), 1.07(s,2H,CH 2 ), 1.225-1.294 (m, 4H, CH 2 ),1.35-1.40(m,4H,CH 2 ), 1.46-1.60(m,6H,CH 2 ),1.74(s,2H,CH 2 ),2.09(s,1H,CH),3.18(t,4H,CH 2 ),5.55(s,1H,CONH); HR-ESIMS m / z 291.2431[M+H] + ,313.2249[M+Na] + .

Embodiment 2

[0058] Example 2: Synthesis of N-(3,5-dimethyladamantan-1-yl)-morpholine-4-carboxamide (ZCY-02)

[0059] Using morpholine as raw material, the synthesis method was the same as (ZCY-01), and 0.5 g of white solid was obtained with a yield of 25.6%. mp 134.8-135.3°C; 1 H-NMR (400MHz, DMSO-d 6 )δ0.80(s, 6H, CH 3 ),1.07(s,2H,CH 2 ), 1.212-1.286 (m, 4H, CH 2 ), 1.500-1.590(m,4H,CH 2 ),1.73-1.76(m,6H,CH 2 ),1.74(s,2H,CH 2 ), 2.04(s,1H,CH), 3.17(t,4H,CH 2 ),3.49(t,4H,CH 2 ),5.70(s,1H, CONH); HR-ESIMS m / z 293.2219[M+H] + ,315.2018[M+Na] + .

Embodiment 3

[0060] Example 3: Synthesis of N-(3,5-dimethyladamantan-1-yl)-pyrrolidine-1-carboxamide (ZCY-03)

[0061] Using pyrrolidine as raw material, the synthesis method is the same as (ZCY-01), and 0.3 g of white solid is obtained with a yield of 16.3%. mp127.1-127.8℃; 1 H-NMR (400MHz, DMSO-d 6 )δ0.80(s, 6H, CH 3 ),1.08(s,2H,CH 2 ),1.210-1.296(m,4H,CH 2 ), 1.508-1.622(m,4H,CH 2 ),1.73-1.76(m,6H,CH 2 ),2.05(s,1H,CH),3.15(t,4H,CH 2 ), 5.02(s,1H,CONH); HR-ESIMS m / z 299.2099[M+Na] + .

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Abstract

The invention belongs to the technical field of medicinal chemistry, in particular to N-(3,5-dimethyladamantane-1-yl)-N'-substituted phenylurea compounds as well as preparation methods and application thereof. The compounds have the structure shown in the formula I. The compounds are proved that the compounds can improve the image recognition memory, the working and learning memory, the spatial learning and memory ability of model rats and has good anti-alzheimer effects by the new object discrimination experiments, Y-maze experiments, positioning navigation and space exploration experiments in mats. The formula I is shown in the description.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to N-(3,5-dimethyladamantan-1-yl)-N'-substituted phenylurea compounds and pharmaceutical compositions as active ingredients, and their preparation Methods and their use in the treatment of Alzheimer's disease. Background technique [0002] Alzheimer's disease (Alzheimer's disease, AD) is a progressive and fatal neurodegenerative disease, clinically manifested as deteriorating cognitive and memory functions, progressive decline in daily life ability, and various neuropsychiatric symptoms and behavioral disturbances that prevent patients from living independently. According to incomplete statistics, by 2025, the number of people with Alzheimer's disease worldwide will reach 2.2 million. In my country, senile dementia mostly occurs in the elderly over the age of 65, accounting for about 4% to 5%, about 10% over the age of 75, and about 20% over the age of 85. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C275/26C07C275/28C07C275/30C07C275/34C07C275/42C07C273/18C07D295/215C07D213/75C07D277/48C07D277/82C07D239/42A61K31/4453A61K31/5375A61K31/40A61K31/4465A61K31/223A61K31/221A61K31/17A61K31/4406A61K31/4402A61K31/4409A61K31/426A61K31/428A61K31/506A61P25/28A61K9/36A61K9/48A61K47/36A61K47/38A61K47/26A61K47/10
CPCA61K9/2054A61K9/2059A61K9/2866A61K9/4858A61K9/4866C07C275/26C07C275/28C07C275/30C07C275/34C07C275/42C07D213/75C07D239/42C07D277/48C07D277/82C07D295/215
Inventor 王绍杰
Owner 沈阳海诺威医药科技有限公司
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