Cabazitaxel Form H Anhydrous Crystallization

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Solution Overview

Problem

Existing crystalline forms of Cabazitaxel, particularly solvates and amorphous forms, face challenges with stability and purity due to volatility of solvents and metastability, leading to inefficiencies in manufacturing and potential conversion to different polymorphs with varying physical properties.

Innovation Solution

A new anhydrous crystalline form of Cabazitaxel, designated as form H, is obtained by crystallizing it from a mixture of decanoyl- and octanoyl triglycerides or glycerol trioctanoate, characterized by specific X-RPD, FTIR, TG, and DSC profiles, ensuring high purity and stability without residual solvents.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If solvate forms of Cabazitaxel are used for crystallization, then purification effectiveness is improved, but stability deteriorates due to solvent volatility and potential polymorphic conversion

Engineering Contradiction:
Improvepurification effectivenessVSAvoidstability
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The patent extracts and removes the crystallization solvent from the final pharmaceutical form. While solvates (acetone, toluene, MTBE, etc.) were effective for purification, the invention develops solvent-free anhydrous crystalline forms (Forms A-F) that eliminate the stability issues associated with volatile solvents, thereby maintaining purification effectiveness while improving long-term stability.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the physical-chemical parameters of the crystalline form by developing multiple distinct anhydrous polymorphic forms (Forms A-F) with different crystal structures. Each form has specific XRD patterns and physical properties, allowing optimization of both purification and stability requirements through parameter selection rather than relying on solvent-containing structures.

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If amorphous forms of Cabazitaxel are used, then processing flexibility is improved, but stability deteriorates due to metastability and potential polymorphic conversion

Engineering Contradiction:
Improveprocessing flexibilityVSAvoidstability
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent utilizes controlled phase transitions by developing specific crystalline forms from various starting materials and processing conditions. The invention demonstrates that despite different preparation paths (amorphous to crystalline, different solvents, etc.), the system can transition to stable crystalline anhydrous forms with defined structures, maintaining processing flexibility while ensuring stability through the final crystalline state.

Inventive Principle:
Principle #36Phase transitions

3Manufacturing precision

If multiple purification techniques are introduced to achieve high purity, then purity is improved, but productivity deteriorates due to longer production times

Engineering Contradiction:
ImprovepurityVSAvoidproduction time
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent applies preliminary action by optimizing the crystallization process itself to achieve high purity in a single step. The anhydrous crystalline forms are designed to crystallize directly from reaction mixtures or with minimal additional purification steps, embedding the purification function within the crystallization process rather than requiring separate sequential purification operations.

Inventive Principle:
Principle #10Preliminary action

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

Form H achieves high purity (>99%) and stability, reducing the risk of polymorphic conversions and improving handling and processability, making it suitable for pharmaceutical applications, especially in cancer treatment.

Implementation Method 1

A new anhydrous crystalline form of Cabazitaxel, designated as form H, is obtained by crystallizing it from a mixture of decanoyl- and octanoyl triglycerides or glycerol trioctanoate

Methodology Applied
Scientific EffectCrystallisation: Crystallisation

Data Source

PatentEP3060556B1A crystalline anhydrous form of cabazitaxel, process for the preparation and pharmaceutical compositions thereof
Publication Date: 2017.08.02 INDENA SPA
  • EP3060556B1 patent drawingFigure 1
  • EP3060556B1 patent drawingFigure 2
  • EP3060556B1 patent drawingFigure 3

AI summary

The present invention relates to a new anhydrous crystalline form of Cabazitaxel of formula (I), designated as form H. A further object of the present invention is a processes for the preparation of the above mentioned form H by recrystallization of Cabazitaxel from a mixture of decanoyl- and octanoyl triglycerides or from glycerol trioctanoate. Form H of Cabazitaxel is useful for the preparation of Cabazitaxel, Cabazitaxel salts, and polymorphic forms thereof. It is also particularly useful as a medicament, especially for the treatment of cancers.