Crystalline CFTR Modulator Stabilization via X-ray Diffraction Control

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Solution Overview

Problem

Current treatments for CFTR-mediated diseases, such as cystic fibrosis, lack effective modulators that can stabilize and enhance CFTR activity in the cell membrane, leading to inadequate ion and fluid transport, resulting in severe respiratory and digestive issues.

Innovation Solution

Development of a crystalline form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide with specific X-ray powder diffraction patterns and a monoclinic crystal system, which forms amorphous or solid dispersions to improve physical and chemical stability, allowing for enhanced CFTR modulation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If crystalline form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is developed with specific X-ray powder diffraction patterns, then physical and chemical stability is improved, but manufacturing complexity increases

Engineering Contradiction:
Improvephysical and chemical stabilityVSAvoidmanufacturing complexity
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by establishing specific crystalline form with defined X-ray powder diffraction patterns (peaks at 6.2±0.2, 7.6±0.2, 12.3±0.2, and 18.0±0.2 degrees) and monoclinic crystal system parameters. By controlling and specifying these physical parameters, the invention achieves improved physical and chemical stability while providing clear manufacturing criteria.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses X-ray diffraction analysis to characterize the crystalline form, replacing complex mechanical characterization methods with a more precise and reliable X-ray-based approach. This substitution enables better control and verification of the crystalline structure without requiring complex mechanical testing procedures.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

2Reliability

If amorphous or solid dispersions are formed to improve stability, then CFTR modulation is enhanced, but manufacturing precision requirements increase

Engineering Contradiction:
ImproveCFTR modulation effectivenessVSAvoiddispersion formation precision
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The patent utilizes parameter changes by defining specific physical characteristics of the crystalline form including unit cell dimensions (a=11.8011(7) Å, b=5.9819(3) Å, c=14.7974(8) Å) and crystal system parameters. These precise parameter specifications enable controlled formation of amorphous or solid dispersions with reproducible properties, balancing manufacturing precision requirements with reliable CFTR modulation.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP3708564B1A solid form of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
Publication Date: 2024.10.09 VERTEX PHARMACEUTICALS INC
  • EP3708564B1 patent drawingFigure 1~2
  • EP3708564B1 patent drawingFigure 3
  • EP3708564B1 patent drawingFigure 4

AI summary

The present invention relates to solid state forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide (Compound 1), pharmaceutical compositions thereof and methods therewith.