Macrocyclic Compounds for Tumor Vascular Remodeling

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Solution Overview

Problem

Current anti-cancer drugs lack effective tumor vascular remodeling effects and anti-CAF (Cancer Associated Fibroblast) activity, which are crucial for improving the cancer microenvironment and inhibiting tumor growth.

Innovation Solution

Development of macrocyclic compounds, such as those represented by Formula (I), which exhibit tumor vascular remodeling effects and anti-CAF activity, potentially used in treating various cancers by inhibiting mitosis and tumor growth.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional anti-cancer drugs are used, then tumor growth inhibition is achieved, but tumor vascular remodeling effects and anti-CAF activity are insufficient

Engineering Contradiction:
Improvetumor vascular remodeling effectsVSAvoidinsufficient anti-CAF activity
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent applies parameter changes by systematically modifying the chemical structure of macrocyclic compounds (Formula I) through variations in ring size, substituent groups, and stereochemistry to optimize both tumor vascular remodeling effects and anti-CAF activity. This involves changing molecular parameters such as ring chain length, functional group positions, and spatial configuration to achieve the desired dual therapeutic effect.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If macrocyclic compounds with dual activity are developed, then tumor vascular remodeling and anti-CAF effects are improved, but drug complexity increases

Engineering Contradiction:
Improveanti-CAF activityVSAvoidcompound structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent implements universality by designing macrocyclic compounds that simultaneously perform multiple functions: inhibiting tumor growth, remodeling tumor vasculature, and suppressing CAF activity. The compounds of Formula (I) are structured to interact with multiple biological targets (tubulin, vascular endothelial cells, and fibroblasts) through their macrocyclic core and strategically positioned functional groups, achieving multi-functionality in a single molecular entity.

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

3Productivity

If tubulin polymerization inhibition is enhanced, then mitosis inhibition is improved, but vascular remodeling effects may be compromised

Engineering Contradiction:
Improvemitosis inhibition efficiencyVSAvoidvascular remodeling effects
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent applies local quality by differentiating the functional roles of specific regions within the macrocyclic molecule. The macrocyclic core structure (Formula I) provides the primary tubulin-binding activity for mitosis inhibition, while specific substituent groups at defined positions (R1-R6 groups) are optimized to confer vascular remodeling and anti-CAF properties. This spatial differentiation of functional qualities within the single molecule allows simultaneous optimization of multiple therapeutic effects.

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 macrocyclic compounds demonstrate significant antitumor effects by remodeling tumor vasculature and reducing CAF activity, thereby enhancing the cancer microenvironment and inhibiting tumor growth, as shown in preclinical models.

Implementation Method 1

Halichondrin B has demonstrated in vitro inhibition of tubulin polymerization, microtubule assembly, beta 5-tubulin crosslinking, GTP and vinblastine binding to tubulin, and tubulin-dependent GTP hydrolysis

Methodology Applied
Scientific EffectTubulin polymerization inhibition:

Implementation Method 2

Eribulin-induced remodeling of abnormal tumor vasculature leads to a more functional microenvironment that may reduce the aggressiveness of tumors due to the elimination of inner tumor hypoxia

Methodology Applied
Scientific EffectVascular remodeling:

Implementation Method 3

Cancer associated fibroblasts (CAFs), which are widely found in a variety of solid tumors, are stromal cells. It is well known that CAFs play an important role in angiogenesis, invasion, and metastasis

Methodology Applied
Scientific EffectAnti-CAF activity:

Data Source

PatentEP3710454B1Macrocyclic compounds and uses thereof
Publication Date: 2024.01.03 EISAI R&D MANAGEMENT CO LTD
  • EP3710454B1 patent drawingFigure 1
  • EP3710454B1 patent drawingFigure 2
  • EP3710454B1 patent drawingFigure 3

AI summary

The present invention provides novel compounds (e.g., compounds of Formulae (I), (II), (III), (IV)) having tumor vascular remodeling effect and/or anti-CAF (Cancer Associated Fibroblasts) activity, or pharmaceutically acceptable salts thereof, optionally in a pharmaceutically acceptable carrier, and a medical uses thereof.