Form I Crystalline Solid for Cystic Fibrosis CFTR Modulation

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Solution Overview

Problem

Current treatments for cystic fibrosis, particularly those targeting the ΔF508 mutation in the CFTR protein, face challenges in achieving stable solid forms suitable for pharmaceutical compositions that can effectively modulate CFTR activity for therapeutic use.

Innovation Solution

A solid dosage form of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid, characterized as Form I, is developed, which is a crystalline form with specific X-ray powder diffraction peaks and a monoclinic crystal system, suitable for oral administration and use in treating cystic fibrosis.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a solid dosage form is developed for oral administration, then the compound can be effectively administered for treating cystic fibrosis, but achieving stable solid forms suitable for pharmaceutical compositions is challenging

Engineering Contradiction:
Improvestability of solid formVSAvoiddifficulty in developing stable solid forms
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies parameter changes by developing multiple crystal forms (Form I, Form II, Form III) with different physical and chemical parameters. Each form has distinct X-ray diffraction patterns, melting points, and solubility characteristics. This allows selection of the most stable and manufacturable form for pharmaceutical use, resolving the contradiction between reliability and ease of manufacture.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite pharmaceutical compositions by combining the active compound in specific crystal forms with pharmaceutically acceptable excipients and carriers. This composite approach enables the development of stable solid dosage forms (tablets, capsules, granules) that are suitable for oral administration and manufacturing, while maintaining the therapeutic efficacy of the compound.

Inventive Principle:
Principle #40Composite materials

2Ease of operation

If the compound is formulated as a solid dosage form, then it is suitable for oral administration and therapeutic use, but the compound requires specific crystalline structures with defined X-ray diffraction patterns

Engineering Contradiction:
Improvesuitability for oral administrationVSAvoidspecific crystal structure requirements
Core Design Contradiction:
Ease of operationVSManufacturing precision

Solution Approach 1:

The patent segments the compound into distinct crystal forms (Form I, Form II, Form III), each with well-defined structural characteristics and X-ray diffraction patterns. This segmentation allows for standardized manufacturing processes tailored to each form, ensuring both oral suitability and structural precision without requiring a single complex formulation approach.

Inventive Principle:
Principle #1Segmentation

3Reliability

If multiple crystal forms are developed, then stable solid forms suitable for pharmaceutical use are achieved, but the complexity of characterizing and controlling crystal forms increases

Engineering Contradiction:
Improvestability for pharmaceutical useVSAvoidcomplexity of crystal form characterization
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent uses X-ray diffraction pattern characteristics as 'fingerprint' identifiers for each crystal form. Form I shows peaks at specific 2θ angles (12.8°, 14.3°, 15.9°, 17.2°), Form II at different angles (13.1°, 14.6°, 16.2°, 17.5°), and Form III with yet another distinct pattern. These characteristic diffraction patterns serve as simple, reliable markers for identifying and controlling the desired crystal form during manufacturing, reducing the complexity of characterization.

Inventive Principle:
Principle #32Color 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 solid dosage form of Form I provides a stable and effective means to modulate CFTR activity, potentially alleviating the severity of cystic fibrosis by enhancing anion transport and ion balance, thereby improving respiratory and digestive health in patients.

Implementation Method 1

3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid characterized as Form I... a solid dosage form comprising 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid characterized as Form I

Methodology Applied
Scientific EffectCrystallisation: Crystallisation

Implementation Method 2

characterized as a crystal form having a monoclinic crystal system... one or more peaks at 15.4 ± 0.2 degrees, 16.3 ± 0.2 degrees, and 14.5 ± 0.2 degrees in an X-ray powder diffraction

Methodology Applied
Scientific EffectX-Ray diffraction: X-Ray

Data Source

PatentEP3683218B1Solid forms of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl) benzoic acid
Publication Date: 2024.09.18 VERTEX PHARMACEUTICALS INC
  • EP3683218B1 patent drawingFigure 1
  • EP3683218B1 patent drawingFigure 2
  • EP3683218B1 patent drawingFigure 3

AI summary

The present invention relates to a substantially crystalline and free solid state form of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid (Form I), pharmaceutical compositions thereof, and methods of treatment therewith.