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3, 5-disubstituted hydantoin compound as well as preparation method and application thereof

A compound, hydrate technology, applied in the field of medicine, to achieve the effect of high safety

Active Publication Date: 2018-10-02
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Based on this hypothesis, pharmaceutical companies have developed various vaccines against the Abeta protein and phosphorylation inhibitors of various enzymes involved in the protein's formation, but so far these efforts have been unsuccessful

Method used

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  • 3, 5-disubstituted hydantoin compound as well as preparation method and application thereof
  • 3, 5-disubstituted hydantoin compound as well as preparation method and application thereof
  • 3, 5-disubstituted hydantoin compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Example 1: preparation of

[0082] Intermediate 3 (190mg, 1.0mmol) was dissolved in 4mL DMF, potassium carbonate (207mg, 1.5mmol) and benzyl bromide (205mg, 1.2mmol) were added successively, and the reaction was stirred at room temperature for 5 hours. After the reaction was completed, the reaction solution was poured into 100 mL of ethyl acetate, washed three times with water and once with saturated brine. The solvent was evaporated to dryness under reduced pressure and purified by silica gel column chromatography to obtain product 50661, a white solid, 220 mg, with a yield of 79%. 1 H NMR (400MHz, CDCl 3 )δ7.24(m,8H),7.13(m,2H),5.90(s,1H),4.56(m,2H),4.24(dd,J=8.3,3.9Hz,1H),3.23(dd,J =14.0,3.9Hz,1H),2.87(dd,J=14.0,8.2Hz,1H).

Embodiment 2

[0083] Example 2: preparation of

[0084] Using the same method as in Example 1, substituting o-fluorobenzyl bromide for benzyl bromide, compound 51231 was prepared as a white solid, 213 mg, with a yield of 71%. 1 H NMR (400MHz, CDCl 3 )δ7.23(m,4H),7.14(m,2H),6.99(m,2H),6.82(m,2H),6.57(s,1H),4.65(m,2H),4.28(dd,J =7.4,3.9Hz,1H),3.18(dd,J=14.1,4.0Hz,1H),2.95(dd,J=14.0,7.2Hz,1H).

Embodiment 3

[0085] Embodiment 3: preparation of

[0086] Using the same method as in Example 1, m-fluorobenzyl bromide was used instead of benzyl bromide to prepare compound 51241, a white solid, 205 mg, with a yield of 69%. 1 H NMR (400MHz, CDCl 3 )δ7.22(m,4H),7.12(m,2H),6.92(m,3H),6.36(s,1H),4.52(m,2H),4.27(dd,J=7.6,4.0Hz,1H ),3.19(dd,J=14.0,4.0Hz,1H),2.92(dd,J=14.0,7.5Hz,1H).

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PUM

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Abstract

The invention provides a 3, 5-disubstituted hydantoin compound as well as a preparation method and an application thereof. The structure of the compound is shown in formula I in the description. The application of the 3, 5-disubstituted hydantoin compound shown in the formula I or solvates, hydrates or salts of the compound in preparation of medicines for treating Alzheimer's disease, vascular dementia and other dementia diseases with memory impairment also belongs to the protection scope. Animal experiments prove that the compound has the effect of saving memory of animal models, has high safety, does not have mutagenicity, can stay in blood for several hours after oral administration and intravenous injection, and can enter the brain.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a class of 3,5-disubstituted hydantoin compounds and a preparation method and application thereof. Background technique [0002] Alzheimer's disease (Alzihemer's disease) is a common neurodegenerative disease, accompanied by memory loss, neuron death and other symptoms, the main clinical signs are senile plaques and nerve fiber tangles. Currently, there is a lack of treatments for this disease. More than ten years ago, the US FDA approved a total of five therapeutic compounds in two categories, including cholinesterase inhibitors and NMDA receptor antagonists, but all of them can only temporarily improve the symptoms of the disease, but cannot prevent the course of the disease. As a result, both the scientific and business communities are actively involved in the understanding of disease mechanisms and the development of related drugs. In order to understand diseases and develop drugs, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/74C07D409/06C07D401/06C07D233/76C07D233/78A61K31/4166A61K31/4174A61K31/4439A61K31/4178A61P25/28
CPCA61P25/28C07D233/74C07D233/76C07D233/78C07D401/06C07D409/06
Inventor 汪舰郎明钟毅马伟伟杜书文
Owner TSINGHUA UNIV
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