Substituted Cinnamoyl Anthranilate Compounds for Fibrosis

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Solution Overview

Problem

Current treatments for chronic heart failure and fibrotic disorders, such as those associated with diabetic cardiomyopathy, often progress despite neurohormonal modulation, and existing antifibrotic agents like tranilast have limitations due to side effects and genetic susceptibility issues, necessitating the development of alternative compounds with anti-fibrotic, anti-inflammatory, and anti-proliferative activities.

Innovation Solution

Development of specific compounds, as defined by Formula 2, which exhibit enhanced anti-fibrotic activity and are used in pharmaceutical compositions for treating focal segmental glomerulosclerosis, characterized by various alkyl, cycloalkyl, and heterocyclic substituents, to inhibit TGF-β-induced fibrosis and inflammation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If tranilast is used to treat fibrotic disorders, then anti-fibrotic activity is achieved, but hyperbilirubinemia and other adverse effects occur due to genetic susceptibility

Engineering Contradiction:
Improveanti-fibrotic activityVSAvoidhyperbilirubinemia and adverse effects
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent develops new compounds (Formula 1 and Formula 2) that replace tranilast as therapeutic agents. These new compounds are designed to provide the necessary anti-fibrotic activity without the problematic side effects, effectively disposing of the problematic drug and replacing it with improved alternatives

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent modifies the chemical structure of tranilast by changing parameters such as substituting the dimethoxycinnamoyl group with various acyl groups (Formula 1) and modifying the anthranilic acid core with different substituents (Formula 2). These parameter changes in molecular structure aim to preserve anti-fibrotic activity while eliminating hyperbilirubinemia and other adverse effects

Inventive Principle:
Principle #35Parameter changes

2Reliability

If existing antifibrotic agents are used, then some therapeutic effect is achieved, but treatment effectiveness is limited due to side effects and genetic susceptibility issues

Engineering Contradiction:
Improvetreatment effectivenessVSAvoidapplicability to different patients
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent develops compounds with broad applicability that can treat fibrotic disorders across different patient populations regardless of genetic susceptibility. The new compounds (Formula 1 and Formula 2) are designed to universally provide anti-fibrotic, anti-inflammatory, and anti-proliferative activities without being constrained by individual genetic variations that affect tranilast metabolism

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

3Reliability

If neurohormonal modulation is used for chronic heart failure, then some cardiac dysfunction is managed, but cardiac dysfunction continues to progress in the majority of patients

Engineering Contradiction:
Improvecardiac dysfunction managementVSAvoidduration of disease progression
Core Design Contradiction:
ReliabilityVSDuration of action of stationary object

Solution Approach 1:

The patent introduces new compounds (Formula 1 and Formula 2) as intermediary substances that mediate between the existing neurohormonal modulation therapy and the pathological fibrotic processes in the heart. These compounds provide additional anti-fibrotic, anti-inflammatory, and anti-proliferative mechanisms that complement neurohormonal modulation to better prevent cardiac dysfunction progression

Inventive Principle:
Principle #24Intermediary (Mediator)

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

These compounds demonstrate significant anti-fibrotic activity, potentially offering improved therapeutic outcomes for fibrotic disorders and reducing fibrosis-related complications in conditions like diabetic cardiomyopathy and glomerulosclerosis, with a reduced risk of adverse effects compared to existing agents.

Implementation Method 1

its ability to inhibit ERK phosphorylation, a major intermediate in the TGF-β signalling pathway, may underlie its antifibrotic effects

Methodology Applied
Scientific EffectTGF-β signaling inhibition:

Data Source

PatentEP2799427B1Therapeutic compounds
Publication Date: 2018.07.04 FIBROTECH THERAPEUTICS
  • EP2799427B1 patent drawingFigure 1
  • EP2799427B1 patent drawingFigure 2
  • EP2799427B1 patent drawingFigure 3

AI summary

The present invention provides substituted cinnamoyl anthranilate compounds exhibiting anti-fibrotic activity; or derivatives thereof, analogues thereof, pharmaceutically acceptable salts thereof, and metabolites thereof; with the proviso that the compound is not Tranilast.