IDO Inhibitor Salt Forms for Solubility and Stability

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Solution Overview

Problem

Existing IDO inhibitors face challenges in solubility and stability, limiting their effectiveness in pharmaceutical applications, particularly in treating diseases associated with IDO such as cancer and infectious diseases.

Innovation Solution

Development of specific salt forms of Compound 1, including HCl, HBr, potassium, and sodium salts, which exhibit enhanced solubility and stability, allowing for more effective pharmaceutical compositions and treatments.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If free acid Compound 1 is used, then the compound can be incorporated into pharmaceutical compositions, but the solubility is insufficient for effective pharmaceutical application

Engineering Contradiction:

ImprovesolubilityVSAvoidpharmaceutical effectiveness

Core Design Contradiction:

Quantity of substanceVSReliability

Solution Approach 1:

The patent applies parameter changes by converting the free acid Compound 1 into different salt forms (HCl, HBr, potassium, and sodium salts). This chemical modification changes the physical and chemical parameters of the compound, specifically improving its solubility in aqueous solutions while maintaining its biological activity as an IDO inhibitor, thereby resolving the contradiction between solubility and pharmaceutical effectiveness

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent creates composite material forms by combining Compound 1 with different counterions to form salt compounds. Each salt form represents a composite material that integrates the parent compound with a specific ion, optimizing the balance between solubility and stability for different pharmaceutical applications

Inventive Principle:

Principle #40Composite materials

2Stability of the object's composition

If free acid Compound 1 is used, then the compound structure is simple, but the stability is insufficient for pharmaceutical storage and application

Engineering Contradiction:

ImprovestabilityVSAvoidcompound structure complexity

Core Design Contradiction:

Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The patent modifies the chemical parameter of Compound 1 by forming salts with different counterions. This changes the chemical stability parameter without significantly altering the core molecular structure responsible for biological activity, thus improving stability while maintaining structural simplicity

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The counterions (HCl, HBr, potassium, sodium) act as intermediaries that stabilize the Compound 1 molecule. These intermediary substances form ionic bonds with the carboxylic acid group of Compound 1, protecting it from degradation while allowing the core structure to remain intact for pharmaceutical use

Inventive Principle:

Principle #24Intermediary (Mediator)

Data Source

PatentUS12509448B2Salts of indoleamine 2,3-dioxygenase inhibitors

Publication Date: 2025.12.30 INVENTISBIO CO LTD

AI summary

Provided herein are compounds, salts, crystalline forms, and pharmaceutical compositions that are related to IDO inhibitors, in particular, Compound 1,1-(5-((4-chlorophenyl)amino)-6-(ethyl(tetrahydro-2H-pyran-4-yl)amino)pyridin-3-yl)cyclobutane-1-carboxylic acid. Also provided are methods of treating a disease or disorder such as a cancer or infectious disease that comprises administering to a subject in need thereof one or more of the compounds or compositions of the present disclosure.