Compound I Salts Enhance STING Pathway Stability

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Solution Overview

Problem

Current pharmaceutical compounds for cancer treatment, specifically targeting STING signaling, face challenges in bioavailability and stability, which affect their efficacy as drug substances.

Innovation Solution

Development of salts and crystals of Compound (I), such as di-ammonium and mono-ammonium salts, which exhibit specific diffraction peaks in powder X-ray diffraction, enhancing their potential as pharmaceutical agents by improving hygroscopicity and stability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If Compound (I) is used as a pharmaceutical compound for cancer treatment, then it can activate the STING pathway and show antitumor activity, but its bioavailability and stability are insufficient

Engineering Contradiction:
ImprovestabilityVSAvoidbioavailability
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent applies parameter changes by converting Compound (I) into different salt forms (ammonium salt, sodium salt, potassium salt) to modify its physical and chemical properties. This transformation changes the solubility, stability, and bioavailability parameters of the compound without altering its core STING pathway activation capability, thereby resolving the contradiction between stability and bioavailability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite material systems by forming salts of Compound (I) with various counterions (ammonium, sodium, potassium). These composite salt forms combine the active pharmacological compound with stabilizing counterions, improving overall stability while maintaining or enhancing bioavailability compared to the free acid form

Inventive Principle:
Principle #40Composite materials

2Reliability

If salts of Compound (I) are developed to improve bioavailability and stability, then their potential as pharmaceutical agents is enhanced, but the complexity of salt selection and characterization increases

Engineering Contradiction:
ImprovestabilityVSAvoidsalt selection complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies local quality by selecting specific counterions (ammonium, sodium, potassium) that provide localized improvements in desired properties. Each salt form is optimized for specific characteristics - ammonium salt for enhanced solubility, sodium/potassium salts for improved stability - allowing selection based on specific pharmaceutical needs without overwhelming complexity

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent uses common inorganic bases (ammonia, sodium hydroxide, potassium hydroxide) as intermediaries to convert Compound (I) into stable salt forms. These intermediary substances facilitate the salt formation process and provide a systematic approach to generating pharmaceutically acceptable salts, reducing the complexity of salt selection

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

The salts and crystals of Compound (I) demonstrate enhanced bioavailability and stability, potentially leading to effective activation of the STING pathway and potent antitumor activities, making them suitable for treating various cancers like glioma, melanoma, and colon cancer.

Implementation Method 1

which exhibit specific diffraction peaks in powder X-ray diffraction

Methodology Applied
Scientific EffectX-ray diffraction: X-Ray

Data Source

PatentEP3837268B1Salts of compounds and crystals thereof
Publication Date: 2025.01.15 EISAI R&D MANAGEMENT CO LTD
  • EP3837268B1 patent drawingFigure 1
  • EP3837268B1 patent drawingFigure 2A
  • EP3837268B1 patent drawingFigure 2B

AI summary

The present invention provides crystals of (1R,3R,15E,28R,29R,30R,31R,34R,36R,39S,41R)-29,41-Difluoro-34,39-bis(sulfanyl)-2,33,35,38,40,42-hexaoxa-4,6,9,11,13,18,20,22,25,27-decaaza-34λ5,39λ5-diphosphaoctacyclo[28.6.4.13,36.128,31.04,8.07,12.019,24.023,27]dotetraconta-5,7,9,11,15,19,21,23,25-nonaene-34,39-dione (Compound (I)) ammonium salts, Compound (I) sodium salts, or Compound (I), possessing a potential to be used as drug substance in pharmaceuticals.