Amphiphilic Additives for Statin Crystallization Control

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Solution Overview

Problem

Current crystallization processes for statin intermediates face challenges in achieving high purity and acceptable filtration properties, particularly with the formation of small particles and low yields due to rapid cooling rates and high solvent consumption, which are not industrially viable.

Innovation Solution

The use of amphiphilic additives, specifically custom-made quarternary amine salts like cetyltrimethylammonium bromide (CTABr), during the crystallization process to control cooling rates and promote larger particle formation, improving filterability and purity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If rapid cooling rates are used during crystallization, then crystallization speed is improved, but particle size becomes small and filtration properties deteriorate

Engineering Contradiction:
Improvecrystallization speedVSAvoidfiltration properties
Core Design Contradiction:
ProductivityVSEase of operation

Solution Approach 1:

An amphiphilic compound is introduced as an intermediary substance during crystallization. This compound has both hydrophilic and hydrophobic regions that allow it to interact with both the statin intermediate molecules and the aqueous solvent system, mediating the crystallization process to produce larger particles with better filtration properties while maintaining high crystallization speed

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention changes the chemical composition parameter of the crystallization system by adding amphiphilic compounds. This alters the interfacial properties and nucleation behavior of the system, enabling controlled crystallization that produces larger particles suitable for filtration while maintaining high productivity

Inventive Principle:
Principle #35Parameter changes

2Device complexity

If standard crystallization procedures are applied to amorphous active compounds, then process simplicity is maintained, but purification efficiency deteriorates

Engineering Contradiction:
Improveprocess simplicityVSAvoidpurification efficiency
Core Design Contradiction:
Device complexityVSManufacturing precision

Solution Approach 1:

The invention modifies the chemical environment parameter by introducing amphiphilic compounds that selectively interact with impurities versus the desired statin intermediate. This creates a differentiated crystallization behavior where pure product crystallizes while impurities remain in solution or form separate phases, achieving high purification efficiency within the existing process framework

Inventive Principle:
Principle #35Parameter changes

3Quantity of substance

If high solvent consumption is used to achieve acceptable crystallization, then dissolution completeness is improved, but cost-effectiveness and industrial viability deteriorate

Engineering Contradiction:
Improvedissolution completenessVSAvoidindustrial viability
Core Design Contradiction:
Quantity of substanceVSEase of manufacture

Solution Approach 1:

The amphiphilic compound acts as a mediator that enhances the solubility and dissolution behavior of the statin intermediate in the solvent system. This allows for more efficient use of the solvent, achieving complete dissolution and high crystallization yields with reduced solvent consumption, thereby improving cost-effectiveness and industrial viability

Inventive Principle:
Principle #24Intermediary (Mediator)

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 approach enables the production of high-purity statin intermediates with improved filtration properties and reduced solvent consumption, making the process more industrially acceptable and cost-effective.

Implementation Method 1

a) dissolving at ambient temperature a rosuvastatin calcium or a hydrate thereof in water containing an anionic surfactant; b) removing water at ambient temperature to reduce the volume of water by 30% or more, relative to the volume used to dissolve rosuvastatin; c) stirring the obtained suspension at ambient temperature for a time sufficient to produce said form B; and d) filtering off the solid.

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Data Source

PatentEP2373609B1Use of amphiphilic compounds for controlled crystallization of statins and statin intermediates
Publication Date: 2013.10.16 KRKA D D NOVO MESTO
  • EP2373609B1 patent drawingFigure 1
  • EP2373609B1 patent drawingFigure 2
  • EP2373609B1 patent drawingFigure 3

AI summary

The invention relates to an improved process comprising amphiphilic compounds for the crystallization of an intermediate used in the process for the preparation of statins and statin intermediates.