Crystal Form D of Pyrazine-2(1H)-ketone for FGFR Selectivity

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Solution Overview

Problem

Current therapies targeting fibroblast growth factor receptors (FGFR) lack specificity and stability, particularly in inhibiting FGFR2 and FGFR3 while minimizing effects on FGFR1 and FGFR4, which is crucial for treating associated diseases effectively.

Innovation Solution

A crystal form D of a pyrazine-2(1H)-ketone compound with specific X-ray powder diffraction peaks and thermal analysis profiles, exhibiting good stability and selective inhibitory activity against FGFR2 and FGFR3, is developed, along with a method for its formulation and synthesis.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If current FGFR therapies are used, then FGFR inhibition is achieved, but selectivity between FGFR2/3 and FGFR1/4 is insufficient

Engineering Contradiction:
ImproveselectivityVSAvoidoff-target effects
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent modifies the chemical structure parameters of the pyrazine-2(1H)-ketone compound to achieve differential binding affinity. Specifically, the compound structure (formula I) with particular substituent groups at defined positions creates selective interaction with FGFR2 and FGFR3 binding pockets while minimizing interaction with FGFR1 and FGFR4, thereby resolving the selectivity contradiction through precise molecular parameter optimization

Inventive Principle:
Principle #35Parameter changes

2Stability of the object's composition

If crystal form D is used, then stability and formulation ease are improved, but additional characterization and validation steps are required

Engineering Contradiction:
Improvecrystal stabilityVSAvoidcharacterization complexity
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The patent identifies and characterizes specific local properties of crystal form D through distinctive XRPD peaks at defined 2θ angles. By establishing these specific diffraction patterns as identification markers, the patent enables targeted quality control that focuses on critical stability-related characteristics rather than comprehensive analysis, thereby managing complexity while ensuring stability

Inventive Principle:
Principle #3Local quality

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 crystal form D demonstrates high selectivity and inhibitory activity against FGFR2 and FGFR3, with good pharmacokinetic profiles, enhancing therapeutic efficacy while maintaining stability for drug formulation.

Implementation Method 1

The X-ray powder diffraction pattern thereof has characteristic diffraction peaks at the following 2θ angles: 9.42 ± 0.20°, 26.28 ± 0.20°, and 27.72 ± 0.20°

Methodology Applied
Scientific EffectX-ray powder diffraction: X-Ray

Implementation Method 2

The X-ray powder diffraction pattern of the crystal form D of compound of formula (II) has characteristic diffraction peaks

Methodology Applied
Scientific EffectBragg diffraction: Bragg Diffraction

Implementation Method 3

the differential scanning calorimetry curve of the crystal form D of the compound of formula (II) has an endothermic peak with an onset at 179.1 °C ± 2.0 °C

Methodology Applied
Scientific EffectDifferential scanning calorimetry: Calorimetry

Implementation Method 4

the thermogravimetric analysis curve of the crystal form D of the compound of formula (II) shows a weight loss of 7.11% at 190.0 °C ± 3.0 °C

Methodology Applied
Scientific EffectThermogravimetric analysis: Thermal Expansion

Data Source

PatentEP4011869B1Crystal form d of pyrazine-2(1H)-ketone compound and preparation method therefor
Publication Date: 2023.11.15 ZHANGZHOU PIEN TZE HUANG PHARM
  • EP4011869B1 patent drawingFigure 1~2
  • EP4011869B1 patent drawingFigure 3
  • EP4011869B1 patent drawing

AI summary

Disclosed are a crystal form of pyrazine-2(1H)-ketone compound and a preparation method therefor. Specifically disclosed is a method for preparing a compound of formula (II) and a crystal form thereof.