Formula I Crystalline Forms for Stability and Low Water Adsorption

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Solution Overview

Problem

There is a need for improved forms of thyroid hormone receptor β (TRβ) agonists to facilitate pharmaceutical development and address conditions such as adrenoleukodystrophy (ALD) and lipid disorders like hypercholesterolemia and fatty liver diseases.

Innovation Solution

The development of crystalline forms of a compound of Formula I, including solvates and unsolvated Form C, which exhibit specific X-ray powder diffraction peaks and provide improved stability, processability, and low water adsorption, achieved through controlled crystallization methods.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If amorphous form of compound is used, then ease of manufacture is improved, but stability and water adsorption properties deteriorate

Engineering Contradiction:
Improveease of manufactureVSAvoidstability
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The patent applies parameter changes by transforming the physical state of the compound from amorphous to crystalline form. This phase transition fundamentally alters the molecular arrangement and intermolecular forces, resulting in improved stability and controlled water adsorption properties while maintaining manufacturability through the described crystallization processes.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent directly utilizes phase transitions by converting the amorphous compound into crystalline forms through controlled crystallization. The phase change from disordered amorphous state to ordered crystalline state provides the desired improvement in stability and water vapor adsorption characteristics, resolving the technical contradiction between ease of manufacture and stability.

Inventive Principle:
Principle #36Phase transitions

2Ease of manufacture

If amorphous form of compound is used, then ease of manufacture is improved, but water adsorption properties deteriorate

Engineering Contradiction:
Improveease of manufactureVSAvoidwater adsorption
Core Design Contradiction:
Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The patent applies parameter changes by transforming the physical state of the compound from amorphous to crystalline form. This phase transition fundamentally alters the molecular arrangement and intermolecular forces, resulting in improved stability and controlled water adsorption properties while maintaining manufacturability through the described crystallization processes.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent directly utilizes phase transitions by converting the amorphous compound into crystalline forms through controlled crystallization. The phase change from disordered amorphous state to ordered crystalline state provides the desired improvement in stability and water vapor adsorption characteristics, resolving the technical contradiction between ease of manufacture and stability.

Inventive Principle:
Principle #36Phase transitions

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 crystalline forms, particularly Form C, offer long-term stability and low water vapor adsorption, enhancing clinical efficacy for treating ALD and lipid disorders.

Implementation Method 1

the crystalline form exhibits an X-ray powder diffraction pattern comprising at least one characteristic peak

Methodology Applied
Scientific EffectX-ray powder diffraction: X-Ray

Implementation Method 2

X-ray powder diffraction pattern comprising at least one characteristic peak

Methodology Applied
Scientific EffectDiffraction: Diffraction

Implementation Method 3

isolating a crystalline form of a compound of Formula I from the second mixture

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Implementation Method 4

isolating a crystalline form of a compound of Formula I from the second mixture

Methodology Applied
Scientific EffectPrecipitation: Precipitation

Implementation Method 5

low water adsorption, achieving long-term stability and low water vapor adsorption

Methodology Applied
Scientific EffectAdsorption: Adsorption

Data Source

PatentEP3768690B1Crystalline forms and methods of producing crystalline forms of a compound
Publication Date: 2025.08.27 VIKING THERAPEUTICS INC
  • EP3768690B1 patent drawingFigure 1
  • EP3768690B1 patent drawingFigure 2
  • EP3768690B1 patent drawingFigure 3

AI summary

Disclosed herein are methods of crystallizing the compound of Formula I, as well as crystalline forms thereof. Crystalline forms of Formula I disclosed include the TBME solvate crystalline form, toluene solvate crystalline form, ethanol solvate crystalline form, THF solvate crystalline form, EtOAc solvate crystalline form, acetone solvate crystalline form and crystalline Form C.