Cabazitaxel Crystalline Form-1 Isolation via Anti-Solvent Precipitation

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Solution Overview

Problem

Current methods for preparing Cabazitaxel crystalline forms are complex and often require specific solvates or hydrates, limiting the direct isolation of novel polymorphic forms.

Innovation Solution

A process involving dissolving crude Cabazitaxel in a chlorinated hydrocarbon and adding an aliphatic hydrocarbon solvent to isolate a novel crystalline polymorph (Form-1), characterized by specific XRPD patterns and DSC curves, which can be further purified and formulated into pharmaceutical compositions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If current methods are used to prepare Cabazitaxel crystalline forms, then specific solvates or hydrates can be obtained, but the process becomes complex and direct isolation of novel polymorphic forms is limited

Engineering Contradiction:
Improvecrystalline form isolationVSAvoidpreparation process
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by modifying the solvent system from traditional acetone or ethanol solvates to a chlorinated hydrocarbon (dichloromethane) combined with an aliphatic hydrocarbon (n-heptane) anti-solvent system. This parameter change in solvent composition enables direct isolation of novel polymorphic Form-1 without requiring complex multi-step processes to obtain specific solvates or hydrates, thereby simplifying the preparation process while improving crystalline form isolation efficiency

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses n-heptane as an intermediary anti-solvent that mediates the crystallization process. By adding n-heptane to the dichloromethane solution of Cabazitaxel, it induces precipitation of the novel polymorphic Form-1. This intermediary substance facilitates the direct isolation of the desired crystalline form without requiring complex purification steps or specific solvate formation procedures

Inventive Principle:
Principle #24Intermediary (Mediator)

2Adaptability or versatility

If multiple solvate forms are prepared through complex processes, then various crystalline forms can be obtained, but the time and steps required increase

Engineering Contradiction:
Improvecrystalline form varietyVSAvoidpreparation time
Core Design Contradiction:
Adaptability or versatilityVSLoss of time

Solution Approach 1:

The patent applies preliminary action by pre-selecting the optimal solvent system (dichloromethane as solvent and n-heptane as anti-solvent) before the crystallization process. This preliminary optimization of solvent parameters enables direct formation of the desired polymorphic Form-1 in a single step, eliminating the need for time-consuming sequential preparation of multiple solvate forms through complex multi-step processes

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent extracts the essential crystallization function by using a simplified two-solvent system that directly yields the novel polymorphic Form-1. Instead of preparing multiple solvate forms (acetone solvate, ethanol solvates, hydrates) through separate complex processes, the method extracts and isolates the desired crystalline form directly through anti-solvent precipitation, significantly reducing preparation time while maintaining versatility

Inventive Principle:
Principle #2Taking out (Extraction)

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

This method allows for the efficient preparation of Cabazitaxel crystalline Form-1 with high purity and stability, suitable for pharmaceutical applications, including the treatment of hormone-refractory metastatic prostate cancer.

Implementation Method 1

dissolving crude Cabazitaxel in chlorinated hydrocarbon

Methodology Applied
Scientific EffectDissolution: Solvation

Implementation Method 2

adding aliphatic hydrocarbon solvent to the solution obtained in step (a)

Methodology Applied
Scientific EffectAnti-solvent precipitation: Precipitation

Implementation Method 3

drying the crystals in vacuum oven at ambient temperature

Methodology Applied
Scientific EffectEvaporation: Evaporation

Data Source

PatentEP2785701B1Crystalline form of carbazitaxel and process for preparation thereof
Publication Date: 2019.01.02 FRESENIUS KABI ONCOLOGY LTD
  • EP2785701B1 patent drawingFigure 1
  • EP2785701B1 patent drawingFigure 2
  • EP2785701B1 patent drawing

AI summary

The present invention discloses Crystalline Forms of 4-acetoxy-2alpha-benzoyIoxy- 5beta-20-epoxy-1-hydoxy-7beta, 10beta-dimethoxy-9-oxotan-11-en-13alpha-y1(2R,3S)-3-tert- butoxycarbony lamino-2-hydoxy-3-phenylpropionate, i.e Cabazitaxel, methods for its preparation and Pharmaceutical compositions thereof.