Solid State Forms of N-((S)-2,3-Dihydroxy-Propyl) Isonicotinamide

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Solution Overview

Problem

There is a lack of publicly disclosed solid state forms of N-((S)-2,3-Dihydroxy-propyl)-3-(2-fluoro-4-iodo-phenylamino)-isonicotinamide, which hinders its development as a pharmaceutical drug substance, particularly in tablet form due to manufacturing, stability, and packaging challenges.

Innovation Solution

Stable crystalline solid state forms (A1, A2, B1, and B2) of the compound are developed, characterized by x-ray powder diffractometry, single crystal diffractometry, FT IR spectroscopy, FT Raman spectroscopy, differential scanning calorimetry, and thermogravimetric analysis, exhibiting high crystallinity, thermal stability, and varying solubility profiles.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If no solid state form is provided, then the compound cannot be formulated into tablets, but manufacturing and stability challenges arise without a stable solid state form

Engineering Contradiction:
Improvetablet manufacturingVSAvoidstability
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent applies parameter changes by discovering and characterizing multiple crystalline forms (A1, A2, B1, B2) of the compound, each with distinct physical properties including solubility, dissolution rate, and stability characteristics. This allows selection of the optimal crystalline form for tablet manufacturing while ensuring stability requirements are met.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent develops pharmaceutical compositions that combine the active compound in specific crystalline forms with pharmaceutically acceptable carriers and excipients. This composite approach enables tablet formulation by integrating the active ingredient with materials that provide manufacturing ease, stability, and desired release characteristics.

Inventive Principle:
Principle #40Composite materials

2Reliability

If crystalline forms are developed to improve stability, then manufacturing and packaging become feasible, but solubility and dissolution kinetics may be compromised

Engineering Contradiction:
ImprovestabilityVSAvoidsolubility and dissolution kinetics
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent resolves this contradiction by identifying and characterizing multiple crystalline forms with different physical properties. Specifically, Form A1 exhibits high solubility and fast dissolution kinetics while maintaining stability, whereas other forms like B1 and B2 offer different stability profiles. This allows optimization based on therapeutic requirements.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies local quality by selecting specific crystalline forms for specific applications. For instance, Form A1 may be selected when rapid dissolution is critical, while other forms may be chosen when maximum stability is the priority. Each crystalline form has localized optimal properties for different therapeutic scenarios.

Inventive Principle:
Principle #3Local quality

3Adaptability or versatility

If multiple solid state forms are developed with varying solubility profiles, then optimal formulation can be selected, but characterization and development complexity increases

Engineering Contradiction:
Improveformulation selectionVSAvoidcharacterization and development
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent systematically characterizes multiple crystalline forms by varying physical and chemical parameters such as solvent systems, temperature, and pH during crystallization. Each form is fully characterized using techniques like XRD, DSC, and solubility measurements, creating a comprehensive database that guides formulation selection while managing development complexity through structured methodology.

Inventive Principle:
Principle #35Parameter changes

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 developed solid state forms provide a stable and effective pharmaceutical dosage form for cancer treatment, offering improved solubility and dissolution kinetics, enabling their use in various cancer therapies and pharmaceutical compositions.

Implementation Method 1

characterized, e.g., by x-ray powder diffractometry

Methodology Applied
Scientific EffectX-ray diffraction: X-Ray

Implementation Method 2

x-ray powder diffractometry

Methodology Applied
Scientific EffectDiffraction: Diffraction

Implementation Method 3

differential scanning calorimetry (DSC)

Methodology Applied
Scientific EffectCalorimetry: Calorimetry

Implementation Method 4

thermogravimetric analysis (TGA)

Methodology Applied
Scientific EffectThermogravimetric analysis:

Data Source

PatentEP2855434B1Solid state forms of n-((s)-2,3-dihydroxy-propyl)-3-(2-fluoro-4-iodo-phenylamino)-isonicotinamide
Publication Date: 2016.06.22 MERCK PATENT GMBH
  • EP2855434B1 patent drawingFigure 1~2
  • EP2855434B1 patent drawingFigure 3~4
  • EP2855434B1 patent drawingFigure 5~6

AI summary

The invention relates to solid state forms of N-((S)-2,3-Dihydroxy- propyl)-3-(2-fluoro-4-iodo-phenylamino)-isonicotinamide or its pharmaceutically acceptable salts, processes for their preparation, e.g. formula (I) and medical uses thereof.