Entrectinib Crystal Forms for Stable, Free-Flowing Drug Production

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Solution Overview

Problem

Existing crystal forms of entrectinib face challenges such as instability, poor solubility, large particle size, static electricity, and poor fluidity, making large-scale production difficult and affecting formulation quality.

Innovation Solution

Development of novel crystal forms A and B of entrectinib with specific X-ray diffraction peaks and preparation methods using solvents like acetone, water, and dioxane, ensuring stability and solubility, and eliminating the need for micronization and crushing.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If entrectinib is stored in conventional crystal forms (Form A, B, C, or D), then it can be stored and handled, but it exhibits poor chemical stability and converts to other crystal forms or amorphous material over time

Engineering Contradiction:
Improvechemical stabilityVSAvoidcrystal form stability
Core Design Contradiction:
Stability of the object's compositionVSReliability

Solution Approach 1:

The patent changes the physical and chemical parameters of entrectinib by introducing a specific solvate structure with dimethyl sulfoxide (DMSO) molecules in a 1:1 ratio, which fundamentally alters the crystal lattice stability and resistance to polymorphic conversion

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite crystalline structure where entrectinib molecules are combined with DMSO solvent molecules in a specific stoichiometric ratio, forming a stable solvate that prevents conversion to other polymorphic forms

Inventive Principle:
Principle #40Composite materials

2Reliability

If entrectinib is administered to achieve effective plasma concentrations, then therapeutic effect is achieved, but the drug exhibits high inter-subject variability in plasma concentrations

Engineering Contradiction:
Improvetherapeutic effectivenessVSAvoidinter-subject variability
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent changes the dissolution and absorption parameters by using the DMSO solvate form, which provides more consistent bioavailability across different subjects compared to conventional crystal forms, thereby reducing inter-subject variability

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If conventional crystal forms of entrectinib are used, then manufacturing is straightforward, but the drug exhibits variable dissolution rates and poor chemical stability

Engineering Contradiction:
Improvemanufacturing simplicityVSAvoiddissolution rate control
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The invention changes the crystalline state parameters by forming a specific solvate with DMSO, which provides more consistent dissolution characteristics and can be manufactured using standard crystallization techniques from DMSO solutions

Inventive Principle:
Principle #35Parameter changes

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 new crystal forms exhibit high purity, stability, and improved solubility, facilitating large-scale production with better fluidity and no static electricity, enhancing drug preparation and formulation processes.

Implementation Method 1

Crystal form of entrectinib and preparation method therefor

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Data Source

PatentEP4273144B1Crystal form of entrectinib and preparation method therefor
Publication Date: 2026.05.06 QILU PHARMA CO LTD
  • EP4273144B1 patent drawingFigure 1~2
  • EP4273144B1 patent drawingFigure 3~4
  • EP4273144B1 patent drawingFigure 5~6

AI summary

The present invention relates to a crystal form of Entrectinib and a preparation method therefor, and specifically relates to a crystal form A and crystal form B of Entrectinib. Compared with existing crystal forms of Entrectinib, the crystal form has better solubility, chemical and crystal form stability, is free of static electricity, has good fluidity, is easy for large-scale preparation, can be better suitable for preparing pharmaceutical formulations and large-scale production, and has a wide application prospect.