Pyrazole Derivative Tau Aggregation Inhibition

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Solution Overview

Problem

Current treatments for Alzheimer's disease, such as Aricept, primarily offer symptomatic relief and do not address the underlying causes of amyloid β-protein and tau aggregation, which are central to the disease's progression.

Innovation Solution

A novel curcumin derivative is synthesized by replacing the 1,3-dicarbonyl moiety with a pyrazole ring and modifying the 4-hydroxy-3-methoxyphenyl groups with substituents, resulting in a compound with potent tau aggregation inhibitory, β-secretase inhibitory, and amyloid β-protein aggregation inhibitory activities, enhancing brain penetration.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If curcumin and its derivatives are used to inhibit Aβ aggregation and secretase activity, then therapeutic potential for Alzheimer's disease is improved, but the compounds suffer from poor brain penetration and insufficient potency

Engineering Contradiction:
Improvetherapeutic potentialVSAvoidpoor brain penetration
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies parameter changes by systematically modifying the chemical structure of curcumin derivatives, specifically replacing the 1,3-dicarbonyl moiety with a pyrazole ring and substituting the 4-hydroxy-3-methoxyphenyl groups with various substituents (R1, R2, R3). These structural parameter changes result in compounds with enhanced brain penetration capability and improved pharmacological potency, directly resolving the contradiction between therapeutic potential and brain penetration.

Inventive Principle:
Principle #35Parameter changes

2Ease of operation

If existing Alzheimer's disease drugs like Aricept are used for symptomatic therapy, then patient symptoms are relieved, but the underlying causes of amyloid β-protein and tau aggregation are not addressed

Engineering Contradiction:
Improvesymptomatic reliefVSAvoidfundamental therapy
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent applies multi-functionality by designing compound (I) that simultaneously performs multiple therapeutic functions: it inhibits tau aggregation, inhibits Aβ aggregation, and inhibits β-secretase activity. This multi-functional approach allows the single compound to address multiple pathological mechanisms of Alzheimer's disease (protein aggregation and enzyme activity) concurrently, providing both symptomatic relief and fundamental therapy, thereby resolving the contradiction between ease of symptomatic treatment and reliability of fundamental therapy.

Inventive Principle:
Principle #6Universality (Multi-functionality)

Data Source

PatentEP3323816B1Novel pyrazole derivative
Publication Date: 2019.07.03 GREEN TECH CO LTD
  • EP3323816B1 patent drawingFigure 1~2
  • EP3323816B1 patent drawingFigure 3~4
  • EP3323816B1 patent drawing

AI summary

Provided is a novel therapeutic means for Alzheimer's disease. In particular, provided is a compound represented by the following general formula (I): [wherein Ar1 represents 2-methoxy-4-(2-pyridylmethoxy)phenyl etc. and Ar2 represents a 1H-indol-6-yl group etc.] or a salt thereof.