Pridopidine Hydrochloride Form II Crystallization

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Solution Overview

Problem

Current development of Pridopidine for Huntington's disease is limited by the availability of only one crystalline form, Form I, which restricts optimization of pharmaceutical properties such as solubility, stability, and manufacturing characteristics, as no new polymorphic forms were discovered during initial synthesis and screening processes.

Innovation Solution

Identification and characterization of a new crystalline form, Form II of Pridopidine hydrochloride, along with a process for its preparation, which involves heating Form I to 203°C for re-crystallization, and the use of seed crystals to stabilize and produce Form II, resulting in distinct X-ray diffraction patterns, thermal profiles, and solubility characteristics.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Device complexity

If only Form I is available for development, then the development process is simpler with fewer forms to screen, but the optimization of pharmaceutical properties such as solubility, stability, and manufacturing characteristics is restricted

Engineering Contradiction:
Improvecomplexity of polymorph screeningVSAvoidoptimization of pharmaceutical properties
Core Design Contradiction:
Device complexityVSAdaptability or versatility

Solution Approach 1:

The patent applies parameter changes by modifying crystallization conditions including solvent selection (ethanol, isopropanol, acetone, toluene, dichloromethane), temperature variations (room temperature, 0°C, 40°C), and saturation levels to discover and characterize Form II, which exhibits different pharmaceutical properties such as improved bulk density (0.382 g/ml vs 0.212 g/ml) and particle shape (less needle-shaped) compared to Form I

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If Form II is used for pharmaceutical processing, then bulk density and particle shape are improved for enhanced processing, but the form transforms rapidly to Form I at ambient conditions

Engineering Contradiction:
Improvepharmaceutical processingVSAvoidstability at ambient conditions
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The patent applies preliminary action by preparing Form II immediately before use through controlled crystallization from hot saturated solutions, filtering while hot, and using the form directly for pharmaceutical processing without prolonged storage at ambient conditions, thereby utilizing its superior bulk density and particle shape properties before transformation to Form I occurs

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent utilizes phase transitions by controlling the crystallization process through temperature changes (heating to dissolve, cooling to crystallize), and by applying seeding techniques where small amounts of Form II crystals are introduced to induce and maintain the desired polymorphic form during the phase transition from solution to solid state

Inventive Principle:
Principle #36Phase transitions

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 II exhibits improved bulk density and particle shape, allowing for enhanced pharmaceutical processing and potentially more stable formulations at elevated temperatures, although it transforms rapidly to Form I at ambient conditions, indicating Form I's stability at room temperature.

Implementation Method 1

heating Form I to 203°C for re-crystallization

Methodology Applied
Scientific EffectRe-crystallization: Crystallisation

Implementation Method 2

heating Form I to 203°C for re-crystallization

Methodology Applied
Scientific EffectPhase transition: Phase Change

Implementation Method 3

the use of seed crystals to stabilize and produce Form II

Methodology Applied
Scientific EffectNucleation: Nucleation

Implementation Method 4

distinct X-ray diffraction patterns

Methodology Applied
Scientific EffectX-ray diffraction: X-Ray

Implementation Method 5

distinct X-ray diffraction patterns

Methodology Applied
Scientific EffectDiffraction: Diffraction

Implementation Method 6

thermal profiles

Methodology Applied
Scientific EffectThermal analysis: Calorimetry

Data Source

PatentEP2753603B1Polymorphic form of pridopidine hydrochloride
Publication Date: 2017.06.21 TEVA PHARMACEUTICALS INTERNATIONAL GMBH
  • EP2753603B1 patent drawingFigure 1
  • EP2753603B1 patent drawingFigure 2
  • EP2753603B1 patent drawingFigure 3

AI summary

This invention relates to a new crystalline form of Pridopidine, a drug substance currently in development for the treatment of Huntington's disease. More specifically the invention provides polymorphic Form II of the Pridopidine hydrochloride salt, a process for the preparation this polymorphic form, pharmaceutical compositions comprising polymorphic Form II, and methods of uses of this polymorphic form.