ABT-888 Crystalline Form 2 X-ray Diffraction Characterization

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Solution Overview

Problem

There is a need for the identification and reproducible manufacture of crystalline forms of ABT-888, as the crystallinity of 2-((R)-2-methylpyrrolidin-2-yl)-1H-benzimidazole-4-carboxamide affects its stability, solubility, dissolution rate, hardness, and melting point, which are crucial for ease of manufacture and formulation in the chemical and therapeutic arts.

Innovation Solution

Characterization and production of 2-((R)-2-methylpyrrolidin-2-yl)-1H-benzimidazole-4-carboxamide Crystalline Form 2, specifically in the trigonal crystal system with defined lattice parameters and diffraction patterns, and its formulation with excipients for therapeutic use, including methods for nucleation and crystal growth to achieve a stable form suitable for cancer treatment.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If crystalline forms of ABT-888 are identified and characterized, then stability, solubility, dissolution rate, hardness, and compressability are improved, but the complexity of characterization and identification processes increases

Engineering Contradiction:
ImprovestabilityVSAvoidcharacterization process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent uses X-ray diffraction patterns (analogous to color changes in optical properties) as unique fingerprints to identify and characterize different crystalline forms of ABT-888. Each crystalline form has a distinct diffraction pattern that serves as a reliable identifier, enabling straightforward characterization without complex analytical procedures.

Inventive Principle:
Principle #32Color changes

Solution Approach 2:

The patent creates reference diffraction patterns for each crystalline form that can be copied and compared against experimental data. This allows for simple identification by pattern matching rather than complex structural analysis, reducing the complexity of characterization while maintaining high reliability.

Inventive Principle:
Principle #26Copying

2Reliability

If crystalline forms of ABT-888 are identified and characterized, then solubility and dissolution rate are improved, but the complexity of formulation processes increases

Engineering Contradiction:
ImprovesolubilityVSAvoidformulation process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent identifies specific crystalline forms with optimized solubility and dissolution rate parameters. By selecting the appropriate crystalline form based on its diffraction pattern, formulators can achieve desired solubility characteristics without complex formulation adjustments, as the crystalline structure itself provides the necessary parameter optimization.

Inventive Principle:
Principle #35Parameter changes

3Manufacturing precision

If specific crystalline forms are produced with defined lattice parameters, then manufacturing precision is improved, but the complexity of production processes increases

Engineering Contradiction:
Improvelattice parameter precisionVSAvoidproduction process complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent performs preliminary identification and characterization of crystalline forms using X-ray diffraction before final production. By establishing the correct diffraction pattern and lattice parameters in advance, the production process can be optimized to consistently produce the desired crystalline form, achieving high manufacturing precision without overly complex real-time control mechanisms.

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

The characterization and formulation of ABT-888 Crystalline Form 2 provide a stable and effective form for cancer treatment, enhancing its therapeutic efficacy when administered alone or with other anticancer drugs, with specific diffraction patterns and lattice parameters ensuring consistent performance.

Implementation Method 1

which, when measured at about 25°C with radiation at 1.54178 Å, is characterized by a powder diffraction pattern having at least three respective 2θ values of about 13.4°, 17.1°, 21.6°, 21.9°, 24.1°, 24.7°, 26.9°, 27.3°, 27.8°, 30.3°, 32.4° and 34.2°

Methodology Applied
Scientific EffectX-ray diffraction: Bragg Diffraction

Implementation Method 2

when measured at about -100°C in the trigonal crystal system and P3 2 space group with radiation at 0.7107 Å, is characterized by respective lattice parameter values a, b and c of 8.599Å ± 0.002Å, 8.599Å ± 0.002 Å and 14.526Å ± 0.006 Å and respective α, β and γ values of 90°, 90° and 120°

Methodology Applied
Scientific EffectX-ray crystallography: Bragg Diffraction

Data Source

PatentEP2727921B12-((R)-2-methylpyrrolidin-2-YL)-1H-benzimidazole-4-carboxamide crystalline form 2
Publication Date: 2017.04.19 ABBVIE IRELAND UNLIMITED CO
  • EP2727921B1 patent drawingFigure 1
  • EP2727921B1 patent drawingFigure 2
  • EP2727921B1 patent drawingFigure 3

AI summary

2-((R)-2-Methylpyrrolidin-2-yl)-1H-benzimidazole-4-carboxamide Crystalline Form 2, ways to make it, compositions comprising it and made using it, and methods of treating patients having disease using it are disclosed.