N-Substituted Isopropyldimethyl Azulene Sulfonamide Derivatives for Gastric Ulcer Treatment

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Solution Overview

Problem

Azulene sodium sulphonate exhibits poor light and heat stability, leading to increased storage and transportation costs due to decomposition and impurity generation, with no reported structural modifications to address these issues.

Innovation Solution

Development of N-substituted isopropyldimethyl azulene sulfonamide derivatives, specifically synthesized through acetyl chlorination and reaction with amine compounds, enhancing stability and therapeutic efficacy while maintaining gastric ulcer treatment effectiveness.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If azulene sodium sulphonate is used as the active ingredient, then excellent anti-inflammatory and wound healing properties are achieved, but poor light stability and heat stability cause decomposition and impurity generation

Engineering Contradiction:
ImprovestabilityVSAvoiddecomposition and impurity generation
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent modifies the chemical structure of azulene sodium sulphonate by introducing N-substituted isopropyldimethyl azulene sulfonamide derivatives, changing the molecular parameters to improve stability while maintaining therapeutic activity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite molecular structures by combining azulene core with sulfonamide groups and various substituent groups (R1-R6), forming stable conjugated structures that resist decomposition

Inventive Principle:
Principle #40Composite materials

2Reliability

If special storage conditions are implemented to prevent decomposition, then product safety is improved, but storage and transportation costs increase

Engineering Contradiction:
Improveproduct safetyVSAvoidstorage and transportation costs
Core Design Contradiction:
ReliabilityVSLoss of energy

Solution Approach 1:

The patent converts the harmful decomposition tendency of azulene sodium sulphonate into a benefit by structurally modifying it to create stable derivatives that naturally resist decomposition, eliminating the need for special storage conditions

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

3Reliability

If structural modification is performed to improve stability, then decomposition is reduced, but manufacturing complexity increases

Engineering Contradiction:
ImprovestabilityVSAvoidmanufacturing complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent segments the molecular structure into distinct functional groups (azulene core, sulfonamide group, and substituent groups R1-R6), allowing independent optimization of each part while maintaining overall stability

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent introduces different substituent groups at specific positions of the azulene molecule to locally improve stability at critical sites while maintaining the overall therapeutic activity of the compound

Inventive Principle:
Principle #3Local quality

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 N-substituted derivatives demonstrate improved stability and enhanced therapeutic activity for gastric ulcer treatment, reducing production costs and ensuring product safety without the need for special storage conditions.

Implementation Method 1

subjecting azulene sodium sulphonate to acetyl chlorination to generate azulene sulfonyl chloride

Methodology Applied
Scientific EffectAcetyl chlorination: Chemical Bonding

Implementation Method 2

reacting the azulene sulfonyl chloride with an amine compound to obtain said derivative

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentUS9376382B2N-substituted isopropyldimethyl azulene sulfonamide derivatives, and preparation method and use thereof
Publication Date: 2016.06.28 SICHUAN GUOKANG PHARMA

AI summary

The present invention provides an N-substituted isopropyldimethyl azulene sulfonamide derivative as represented by formula (I), and preparation method and uses thereof, wherein R1 is an alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, amino, or a substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, and amino. The N-substituted isopropyldimethyl azulene sulfonamide derivative can be used in treating gastric ulcer.