Polymorphic Forms of PI3K Inhibitor for Stability

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Solution Overview

Problem

Current compounds for inhibiting phosphatidylinositol 3-kinase (PI3K) activity, such as (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one, face challenges in bioavailability and stability, particularly in the treatment of hematologic malignancies like leukemia and lymphoma, where specific polymorphic forms are needed for effective pharmaceutical compositions.

Innovation Solution

Development of polymorphic forms (Forms I, II, III, IV, V, VI, and VII) of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one, characterized by specific X-ray powder diffraction patterns and differential scanning calorimetry, which are bioavailable and stable, and their use in pharmaceutical compositions for treating hematologic malignancies.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional compounds are used to inhibit PI3K activity, then the compound structure is simple and easy to manufacture, but the bioavailability and stability are insufficient

Engineering Contradiction:
Improvebioavailability and stabilityVSAvoidcompound structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by modifying the physical and chemical parameters of the compound through polymorphic form selection. Different polymorphic forms (Form I, Form II, Form III, etc.) exhibit different solubility, bioavailability, and stability characteristics. By selecting and controlling specific polymorphic forms, the patent optimizes the bioavailability and stability parameters without changing the fundamental chemical structure of the PI3K inhibitor compound.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite material strategies by creating pharmaceutical compositions that combine the PI3K inhibitor compound with specific excipients and carriers. These compositions are formulated to enhance the bioavailability and stability of the active compound while maintaining manufacturability. The composite formulation approach allows optimization of drug delivery properties without requiring complex structural modifications of the parent compound.

Inventive Principle:
Principle #40Composite materials

2Reliability

If polymorphic forms are developed to improve bioavailability and stability, then the pharmaceutical efficacy is enhanced, but the manufacturing and characterization processes become more complex

Engineering Contradiction:
Improvepharmaceutical efficacyVSAvoidmanufacturing process complexity
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies preliminary action by pre-characterizing and establishing the properties of different polymorphic forms during the drug development phase. The patent provides detailed characterization data for each polymorphic form (Forms I-VII) including X-ray diffraction patterns, melting points, solubility, and stability profiles. This preliminary characterization work is completed before manufacturing scale-up, allowing for informed selection of the most suitable polymorphic form and simplifying subsequent manufacturing processes by having all necessary data ready in advance.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent utilizes parameter changes to control polymorphic form formation during manufacturing. By adjusting parameters such as solvent selection, temperature, pH, and crystallization conditions, the patent enables controlled production of specific polymorphic forms. This approach allows manufacturers to selectively produce the desired polymorphic form (e.g., Form I or Form II) with optimized efficacy while maintaining manageable manufacturing processes through parameter control rather than complex procedural steps.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If specific polymorphic forms are used for treating hematologic malignancies, then the treatment effectiveness is improved, but the identification and selection of appropriate forms becomes more difficult

Engineering Contradiction:
Improvetreatment effectivenessVSAvoidpolymorph identification difficulty
Core Design Contradiction:
ReliabilityVSDifficulty of detecting and measuring

Solution Approach 1:

The patent applies physical property changes (analogous to color changes principle) by utilizing distinct and measurable physical characteristics of each polymorphic form for easy identification. Each polymorphic form (Forms I-VII) possesses unique X-ray diffraction patterns with characteristic peak positions and intensities, distinct melting points, and specific solubility profiles. These physically distinct and easily measurable properties serve as fingerprints for rapid identification and selection of the appropriate polymorphic form for treatment, eliminating the need for complex analytical procedures.

Inventive Principle:
Principle #32Color changes

Solution Approach 2:

The patent implements feedback mechanisms by establishing clear characterization criteria and reference data for each polymorphic form. The patent provides detailed X-ray diffraction patterns, thermal analysis data, and solubility measurements that serve as reference feedback for quality control and form identification. This feedback system allows manufacturers and researchers to quickly determine which polymorphic form is present by comparing measured properties against the established reference data, facilitating rapid and accurate form selection for treatment.

Inventive Principle:
Principle #23Feedback

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 polymorphic forms enhance bioavailability and stability, allowing for effective treatment of hematologic malignancies like leukemia and lymphoma by providing a stable and bioavailable pharmaceutical composition that can target PI3K activity.

Implementation Method 1

having an X-ray powder diffraction pattern comprising characteristic peaks at, plus or minus 0.2 degrees 2θ, 17.7 degrees 2θ and 24.9 degrees 2θ, as determined by using a Cu anode and Kα1/Kα2 radiation

Methodology Applied
Scientific EffectX-ray diffraction: X-Ray

Implementation Method 2

characterized by specific X-ray powder diffraction patterns and differential scanning calorimetry

Methodology Applied
Scientific EffectDifferential scanning calorimetry: Calorimetry

Data Source

PatentEP2834241B1Polymorphic forms of (s)-2-(1-(9h-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one
Publication Date: 2020.11.18 GILEAD CALISTOGA LLC
  • EP2834241B1 patent drawingFigure 1A
  • EP2834241B1 patent drawingFigure 1B
  • EP2834241B1 patent drawingFigure 2A

AI summary

Polymorphs of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin- 4(3H)-one, compositions thereof, methods for their preparation, and methods for their use are disclosed.