Compound for treating alzheimer's disease

A technology for Alzheimer's disease, compounds, applied in the field of medicine, which can solve the problems of lack of treatment, prevention or mitigation of Alzheimer's disease

Active Publication Date: 2021-08-06
XIAMEN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, there is currently a great lack of drugs with therapeutic, preventive or palliative effects on Alzheimer's disease

Method used

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  • Compound for treating alzheimer's disease
  • Compound for treating alzheimer's disease
  • Compound for treating alzheimer's disease

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0127] Example 1. Preparation of compound XMU1

[0128]

[0129] Step 1) Under nitrogen protection, potassium carbonate (2.93g, 21.22mmol), 4-(bromomethyl)-1-fluoro-2-(trifluoromethyl)benzene (3g, 11.67mmol) and 5-bromo -2-Hydroxybenzaldehyde (2.13g, 10.61mmol) was successively added to a 250ml three-neck flask, then 60ml DMF was added, and magnetically stirred at room temperature 25°C to obtain a suspension, which was stirred overnight at room temperature (about 15 hours), and TLC the next day Monitor the disappearance of starting material and terminate the reaction. The reaction solution was poured into 1.2L ice water, there was a white precipitate, the white solid obtained was filtered, washed with 3×500ml water, and dried in vacuo to obtain 5-bromo-2-(4-fluoro-3-(trifluoromethyl)benzyl oxy)benzaldehyde (3.5 g, 87.46%) as a white solid. The following reaction formula is shown:

[0130]

[0131] Step 2) Under nitrogen protection, add 5-bromo-2-(4-fluoro-3-(trifluoro...

Embodiment 2

[0134] Embodiment 2. Preparation of compound (2)

[0135]

[0136] Step 1) 3,5-bistrifluoromethylbenzyl bromide (0.22mL, 1.2mmol), 4-difluoromethoxy-3-hydroxybenzaldehyde (0.13g, 1mol), potassium carbonate (0.41g, 3mmol ), DMF (10 mL) were successively added into a 100 ml single-necked round bottom flask, reacted at room temperature for 6 h, extracted with ethyl acetate, combined the organic phases, concentrated under reduced pressure, and then purified on a silica gel column to obtain a white solid (0.37 g, 89.3%).

[0137] 1 H NMR (400MHz, CDCl 3 )δ9.95(s,1H),7.94(s,2H),7.88(s,1H),7.58(d,J=1.8Hz,1H),7.55(dd,J=8.1,1.8Hz,1H), 7.39(d, J=8.1Hz, 1H), 6.65(t, J=73.2Hz, 1H), 5.29(s, 2H).

[0138] MS(ESI):m / z 415.05[M+H] + ;

[0139] Step 2) 4-difluoromethoxy-3-(3,5-bistrifluoromethylbenzyl)benzaldehyde (0.21g, 0.5mmol), ethanolamine (0.09ml, 1.5mmol), acetic acid (0.17mL , 1.5mmol), THF (10mL) were sequentially added into a 100mL three-necked round-bottomed flask, protecte...

Embodiment 3

[0142] Embodiment 3. Preparation of compound (5)

[0143]

[0144] Step 1) 3,5-bistrifluoromethylbenzyl bromide (0.22mL, 1.2mmol), 4-difluoromethoxy-3-hydroxybenzaldehyde (0.13g, 1mol), potassium carbonate (0.41g, 3mmol ), DMF (10 mL) were successively added to a 100 ml single-necked round bottom flask, reacted at room temperature for 6 h, extracted with ethyl acetate, combined the organic phases, concentrated under reduced pressure, and then purified on a silica gel column to obtain a white solid (0.37 g, 89.3%).

[0145] 1 H NMR (400MHz, CDCl 3 )δ9.95(s,1H),7.94(s,2H),7.88(s,1H),7.58(d,J=1.8Hz,1H),7.55(dd,J=8.1,1.8Hz,1H), 7.39(d, J=8.1Hz, 1H), 6.65(t, J=73.2Hz, 1H), 5.29(s, 2H).

[0146] MS(ESI):m / z 415.05[M+H] + ;

[0147] Step 2) 4-difluoromethoxy-3-(3,5-bistrifluoromethylbenzyl)benzaldehyde (0.21g, 0.5mmol), N-methylpiperazine (0.17mL, 1.5mL) , acetic acid (0.17mL, 1.5mmol), THF (10mL) were sequentially added to a 100mL three-necked round-bottomed flask, protecte...

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PUM

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Abstract

The invention provides a compound as shown in a formula I, and various crystal forms, hydrates, solvates or pharmaceutically acceptable salts and pharmaceutical compositions thereof. The compound disclosed by the invention can be used for effectively treating the Alzheimer disease, especially cognitive function impairment caused by the Alzheimer disease.

Description

technical field [0001] The present invention relates to the field of medicine; specifically, the present invention relates to small molecular compounds for treating Alzheimer's disease and applications thereof. Background technique [0002] Alzheimer's disease (Alzheimer's disease, AD) is one of the most common degenerative diseases of the central nervous system in the elderly, clinically characterized by progressive memory, cognitive impairment and abnormal behavior, and the typical pathological manifestations Amyloid plaques, Neurofibrillary tangles (NFT). With the aging of the social population, the prevalence of Alzheimer's disease is gradually increasing: in the population aged 65-74, the incidence rate of AD is about 5%, and in the population over 85 years old , the incidence of AD is about 50%. AD has become a global public health problem. It is estimated that by 2020, there will be more than 40 million dementia patients in the world, and AD patients account for abo...

Claims

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Application Information

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IPC IPC(8): C07C217/58C07D295/096C07D209/14A61K31/137A61K31/495A61K31/4045A61P25/28
CPCC07C217/58C07D295/096C07D209/14A61K31/137A61K31/495A61K31/4045A61P25/28A61K38/17C07D213/74A61P43/00C07D211/26C07D217/20C07C47/575C07C43/23C07C43/295
Inventor 王鑫马磊付建军郑秋阳周立成邓青芳时夕蒙李桂林王世华
Owner XIAMEN UNIV
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