IDH Mutant Modulators Targeting Alpha Hydroxyl Neoactivity

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Solution Overview

Problem

There is an ongoing need for modulators of IDH mutants with alpha hydroxyl neoactivity, as an imbalance in the production and elimination of neoactive products like 2HG is associated with diseases, particularly cancer, and existing treatments are inadequate in addressing this imbalance.

Innovation Solution

Development of compounds and compositions that modulate IDH mutants by inhibiting their alpha hydroxyl neoactivity, specifically targeting IDH1 and IDH2 mutants with mutations at residues such as R132H, R132C, V71I, R109, and others, to reduce the levels of 2HG and its associated neoactivity, thereby treating cancer characterized by these mutations.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If IDH mutants with alpha hydroxyl neoactivity are left unmodulated, then the neoactive product (2HG) accumulates to harmful levels, but existing treatments fail to specifically address this imbalance

Engineering Contradiction:
Improveaccumulation of neoactive product 2HGVSAvoideffectiveness of existing treatments
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The patent introduces compounds of formula (I) as intermediary substances that specifically bind to and modulate IDH mutants, blocking their neoactivity. These compounds act as mediators between the mutated enzyme and the neoactive product accumulation, preventing 2HG formation without affecting normal IDH function in healthy cells.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention changes the functional parameters of IDH mutants by introducing compounds that selectively alter the enzyme's catalytic activity. The compounds modify the neoactivity parameter (alpha hydroxyl activity) while preserving or selectively affecting the wild-type enzyme activity, thereby restoring metabolic balance in cancer cells.

Inventive Principle:
Principle #35Parameter changes

2Object-affected harmful factors

If compounds of formula (I) are used to inhibit IDH mutant neoactivity, then the levels of neoactive product 2HG are reduced, but the complexity of targeted therapy increases

Engineering Contradiction:
Improvelevels of neoactive product 2HGVSAvoidcomplexity of targeted therapy
Core Design Contradiction:
Object-affected harmful factorsVSDevice complexity

Solution Approach 1:

The patent describes a universal compound framework (formula I) with variable substituents that can target multiple IDH mutant variants (IDH1 and IDH2 with different mutations). This universal approach allows a single compound structure to address diverse neoactive mutations, reducing the need for multiple specialized treatments.

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

Solution Approach 2:

The compound structure is segmented into a core framework (formula I) with variable substituents (R1-R6, W-X-Y-Z, B-B1). This segmentation allows systematic optimization of compound properties while maintaining the core inhibitory mechanism, enabling tailored therapies for different mutant types without completely redesigning the molecule.

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

The compounds effectively lower the levels of neoactive products like 2HG, thereby addressing the imbalance and providing a therapeutic approach for cancers characterized by IDH mutations, potentially reducing side effects and improving treatment outcomes.

Implementation Method 1

Isocitrate dehydrogenase, also known as IDH, is an enzyme which participates in the citric acid cycle. It catalyzes the third step of the cycle: the oxidative decarboxylation of isocitrate, producing alpha-ketoglutarate (α-ketoglutarate or α-KG) and CO2 while converting NAD+ to NADH.

Methodology Applied
Scientific EffectEnzyme catalysis: Enzyme

Implementation Method 2

This is a two-step process, which involves oxidation of isocitrate (a secondary alcohol) to oxalosuccinate (a ketone), followed by the decarboxylation of the carboxyl group beta to the ketone, forming alpha-ketoglutarate.

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentEP2509600B1Therapeutically active compounds for use in the treatment of cancer characterized as having an IDH mutation
Publication Date: 2017.08.02 AGIOS PHARMACEUTICALS INC
  • EP2509600B1 patent drawingFigure 1
  • EP2509600B1 patent drawingFigure 1A
  • EP2509600B1 patent drawingFigure 1B

AI summary

Compounds and compositions comprising compounds useful in the treatment of cancer are described herein. The compounds and compositions can be used to modulate an isocitrate dehydrogenase (IDH) mutant (e.g., IDHIm or IDH2m) having alpha hydroxyl neoactivity.