Cyclobutylidenemethyl Trimethoxybenzene Compound for Diffusion Depolarization

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Solution Overview

Problem

Existing drugs are ineffective in inhibiting diffusion depolarization in neurological disorders such as migraine aura, ischemic stroke, traumatic brain injury, and Parkinson's disease.

Innovation Solution

Development of a 1-(cyclobutylidenemethyl)-2, 4, 5-trimethoxybenzene compound through a specific synthesis process, which can be administered in various dosage forms to inhibit diffusion depolarization and treat associated neurological disorders.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If commercially available drugs are used, then treatment of neurological disorders is attempted, but they are ineffective in inhibiting diffusion depolarization

Engineering Contradiction:
Improveeffectiveness in inhibiting diffusion depolarizationVSAvoidapplicability to various neurological disorders
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure parameters of existing compounds to create new compounds with formula (I) that have enhanced ability to inhibit diffusion depolarization. The structural modifications include specific substitutions at positions 2, 4, and 5 of the benzene ring with methoxy groups and a cyclobutylidenemethyl group at position 1, which optimizes the compound's pharmacological properties for treating neurological disorders

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite materials principle by creating compounds that combine multiple functional groups (methoxy groups, cyclobutylidenemethyl group) on a benzene ring structure. This composite molecular structure integrates various pharmacophores that work synergistically to inhibit diffusion depolarization and treat multiple neurological disorders including epilepsy, stroke, and Parkinson's disease

Inventive Principle:
Principle #40Composite materials

2Reliability

If a new compound is developed to inhibit diffusion depolarization, then effectiveness in treating neurological disorders is improved, but the complexity of synthesis and development increases

Engineering Contradiction:
Improveneuroprotective effectVSAvoidsynthesis process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies segmentation by dividing the synthesis into distinct stages: first forming the core benzene ring structure with methoxy groups, then introducing the cyclobutylidenemethyl substituent. This segmented approach allows for systematic optimization of each synthesis step and facilitates the development of standardized protocols for producing compounds with formula (I)

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent utilizes parameter changes in the synthesis process by optimizing reaction conditions such as temperature, solvent selection, and catalyst types for each synthesis step. These parameter adjustments streamline the production process while maintaining high purity and yield of the final compound, reducing overall synthesis complexity

Inventive Principle:
Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The compound effectively reduces seizures, improves neurobehavioral function, restores motor and sense functions, enhances blood-brain barrier integrity, and reduces neuroinflammatory responses, demonstrating significant neuroprotective effects in animal models of epilepsy, stroke, and Parkinson's disease.

Implementation Method 1

mixing a compound 1a with dichloromethane to obtain a mixture, and adding a compound 1b to the mixture for reaction to obtain a compound 1c

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

mixing the compound 1c, compound 1d, and aluminum trichloride with methylene chloride in turn for reaction to obtain a compound 1e

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

mixing the compound 1e, sodium borohydride solution, and sodium hydroxide solution with tetrahydrofuran in turn for reaction to obtain a compound 1f

Methodology Applied
Scientific EffectReduction: Reduction

Implementation Method 4

mixing the compound 1f, sodium acetate, and acetic anhydride for reaction to obtain the 1-(cyclobutylidenemethyl)-2, 4, 5-trimethoxybenzene compound

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentEP4624448A11-(cyclobutylidenemethyl)-2,4,5-trimethoxybenzene compound, preparation method therefor and use thereof
Publication Date: 2025.10.01 CHENGDU XINRUI TAIKANG TECH CO LTD
  • EP4624448A1 patent drawingFigure 1~3
  • EP4624448A1 patent drawingFigure 4~6
  • EP4624448A1 patent drawingFigure 7~8

AI summary

A 1-(cyclobutylidenemethyl)-2, 4, 5-trimethoxybenzene compound and a preparation method and use thereof are provided, belonging to the field of drug development technology. The prepared 1-(cyclobutylidenemethyl)-2, 4, 5-trimethoxybenzene compound may be used for the preparation of an antiepileptic drug and drugs for treatment and/or prevention of traumatic craniocerebral injury disorders, ischemic stroke, hemorrhagic stroke, and Parkinson's disease.