Amorphous Solid Form of Glucocorticoid Receptor Antagonist via Precipitation

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Solution Overview

Problem

Existing preparations of compound 1, a glucocorticoid receptor antagonist, have been unable to produce a solid form, which is necessary for easier handling and formulation into pharmaceutical dosage forms, despite its potential in treating psychiatric illnesses and Cushing's syndrome.

Innovation Solution

An amorphous solid form of compound 1 is achieved by dissolving it in solvents like acetone, methanol, or 1,4-dioxane and then precipitating it with water or heptane, using specific solvent ratios and cooling techniques to isolate the solid form.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Shape

If compound 1 is prepared using conventional methods, then the compound can be synthesized, but it cannot be obtained in a solid form

Engineering Contradiction:
Improvesolid formVSAvoiddifficulty to produce solid form
Core Design Contradiction:
ShapeVSEase of manufacture

Solution Approach 1:

The patent applies parameter changes by systematically varying solvent types (polar, non-polar, protic, aprotic), solvent ratios, temperatures, and pH conditions to transform the compound from an unobtainable solid state to a precipitable solid form. This involved testing numerous solvent combinations and conditions to identify parameters that enable solid formation.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses solvents as intermediary substances to mediate the formation of solid compound 1. Specific solvents act as mediators that facilitate precipitation by creating conditions where the compound transitions from dissolved state to solid precipitate, enabling solid form acquisition without direct synthesis modification.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Ease of operation

If compound 1 is administered in oil or gum form, then it can be delivered, but handling and formulation are difficult

Engineering Contradiction:
Improveease of handlingVSAvoidformulation difficulty
Core Design Contradiction:
Ease of operationVSEase of manufacture

Solution Approach 1:

The patent exploits phase transitions by inducing the compound to transition from dissolved liquid phase to solid precipitate phase through controlled precipitation conditions. This phase change enables the compound to be obtained as a solid form that is easier to handle, store, and formulate into pharmaceutical dosage forms compared to oil or gum forms.

Inventive Principle:
Principle #36Phase transitions

Solution Approach 2:

Instead of attempting to solidify the compound through conventional crystallization methods that failed, the patent inverts the approach by using precipitation from solution - dissolving the compound in suitable solvents and then inducing solid formation through anti-solvent addition or evaporation, thereby achieving solid form through the reverse process pathway.

Inventive Principle:
Principle #13The other way round (Inversion)

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 method successfully produces an amorphous solid form of compound 1, characterized by X-ray diffraction, thermal gravimetric analysis, and differential scanning calorimetry, offering improved handling and formulation options for pharmaceutical use.

Implementation Method 1

contacting the first solution with water, wherein the ratio of solvent to water is from about 2:1 to about 1:2 (vol/vol), thereby precipitating the compound of Formula I

Methodology Applied
Scientific EffectPrecipitation: Precipitation

Data Source

PatentEP2429529B1Solid forms and process for preparing
Publication Date: 2015.01.14 CORCEPT THERAPEUTICS INC
  • EP2429529B1 patent drawingFigure 1
  • EP2429529B1 patent drawingFigure 2
  • EP2429529B1 patent drawingFigure 3

AI summary

The present invention provides amorphous solid forms of the compound of Formula I, as well as methods for preparing the compound of Formula I by precipitation.