TDO IDO Inhibitor Compounds Selective Enzyme Binding

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Solution Overview

Problem

Current treatments for cancer, inflammatory conditions, infectious diseases, and central nervous system disorders often rely on tryptophan-2,3-dioxygenase (TDO) and indoleamine-2,3-dioxygenase (IDO) inhibitors, but there is a need for more effective compounds that can selectively inhibit these enzymes to modulate immune responses and neuroactive metabolite production.

Innovation Solution

Development of specific TDO and/or IDO inhibitor compounds with defined structural formulas, which can prevent or reduce the conversion of tryptophan into N-formylkynurenine, thereby modulating tryptophan catabolism and immune regulation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If TDO and IDO inhibitors are used to modulate immune responses, then therapeutic effectiveness is improved, but selectivity and specificity of enzyme inhibition remain challenging

Engineering Contradiction:
Improvetherapeutic effectivenessVSAvoidselectivity and specificity
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies local quality by designing inhibitors with specific structural features (substituted benzofuran, benzothiophene, or indazole cores with particular substituent patterns) that create localized interaction zones within the enzyme active site. This enables selective binding to TDO or IDO based on subtle differences in their active site architectures, achieving both therapeutic effectiveness and enzyme selectivity.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent employs parameter changes by systematically varying key molecular parameters of the inhibitor compounds including substituent types (R1-R6 groups), linkage structures (L1-L3), and core heterocyclic systems. These parameter variations allow optimization of binding affinity and selectivity for TDO versus IDO, resolving the contradiction between effectiveness and selectivity through structured molecular design.

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If broad-spectrum TDO/IDO inhibition is achieved, then versatility in treating multiple diseases is improved, but precision in targeting specific enzyme isoforms decreases

Engineering Contradiction:
Improveversatility in treating multiple diseasesVSAvoidprecision in targeting specific enzyme isoforms
Core Design Contradiction:
Adaptability or versatilityVSMeasurement precision

Solution Approach 1:

The patent applies universality by creating a platform of inhibitors with core structures that can bind to both TDO and IDO enzymes, while allowing substituent variations to fine-tune selectivity. The compounds of formula (1) and its variants serve multiple therapeutic purposes across different diseases (cancer, inflammatory conditions, infectious diseases, CNS disorders) while maintaining the ability to preferentially inhibit either TDO or IDO based on molecular design.

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

Solution Approach 2:

The patent uses segmentation by dividing the inhibitor molecule into distinct functional segments: a core heterocyclic system (benzofuran/benzothiophene/indazole), linking groups (L1-L3), and terminal substituents (R1-R6). This segmentation allows independent optimization of each segment to achieve both broad disease applicability and precise enzyme isoform targeting through combinatorial molecular design.

Inventive Principle:
Principle #1Segmentation

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 effectively inhibit TDO and/or IDO activity, potentially offering new therapeutic options for treating various diseases by modulating immune responses and neuroactive metabolite production, thereby providing a targeted approach to disease management.

Implementation Method 1

Both enzymes catalyze the oxidative cleavage of the 2,3 double bond in the indole ring, converting tryptophan to N-formylkynurenine.

Methodology Applied
Scientific EffectOxidative cleavage: Oxidation

Data Source

PatentEP3319606B1Pharmaceutical compound
Publication Date: 2020.12.09 IOMET PHARMA
  • EP3319606B1 patent drawingFigure 1
  • EP3319606B1 patent drawingFigure 2
  • EP3319606B1 patent drawing

AI summary

Provided is a tryptophan-2,3-dioxygenase (TDO) and/or indoleamine-2,3-dioxygenase (IDO) inhibitor compound for use in medicine, which compound comprises the general formula (I) detailed within.