Hydrobromide Salt Crystal Form for Stable Cancer Formulation

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Solution Overview

Problem

Existing gamma-secretase inhibitors face challenges in achieving optimal characteristics for therapeutic use, including high affinity, duration of gamma-secretase deactivation, oral bioavailability, tissue distribution, and stability, while the isolation and formulation of solid state forms of hydrobromide salts of Compound 1 present issues with chemical and physical properties such as solubility, hygroscopicity, and manufacturability.

Innovation Solution

Development of crystalline forms of hydrobromide salts of Compound 1, specifically crystalline Form A, characterized by distinct XRPD patterns and thermal stability, which addresses the balance of properties for pharmaceutical formulations, including anhydrous Form A with a melting point of about 254 °C and specific XRPD peaks.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If crystalline forms of hydrobromide salts of Compound 1 are developed to improve chemical and physical stability, then formulation feasibility and shelf life are improved, but the complexity of isolation and commercial-scale preparation increases

Engineering Contradiction:
Improvechemical and physical stabilityVSAvoidcomplexity of isolation and preparation
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The patent segments the compound into multiple distinct crystalline forms (Form A, Form B, Form C, etc.), each with unique properties optimized for different aspects of stability and manufacturability. This segmentation allows selection of the most appropriate form for specific formulation needs, resolving the contradiction between stability and preparation complexity.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent utilizes parameter changes in the crystalline structure (polymorphism) to achieve different stability profiles. By varying the crystal packing arrangement while maintaining the same chemical composition, the patent optimizes chemical stability, physical stability, solubility, and manufacturability parameters simultaneously.

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If solid state forms with acceptable solubility and hygroscopicity are isolated, then formulation feasibility is improved, but manufacturing yield and impurity rejection during crystallization are compromised

Engineering Contradiction:
Improveformulation feasibilityVSAvoidmanufacturing yield and impurity rejection
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

The patent performs preliminary action by pre-characterizing multiple crystalline forms with their respective solubility, hygroscopicity, and crystallization properties. This allows selection of the optimal form that balances formulation feasibility with manufacturing efficiency, avoiding the need to optimize for conflicting properties simultaneously.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent identifies crystalline forms that can be prepared through simple, scalable crystallization processes with acceptable yield, even if not all properties are optimal. The focus is on finding forms that are sufficiently stable and formulable without requiring complex, low-yield purification steps.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

3Adaptability or versatility

If multiple crystalline forms are characterized to find the optimal balance of properties, then formulation feasibility is improved, but the time and resources required for characterization increase

Engineering Contradiction:
Improveformulation feasibilityVSAvoidtime for characterization
Core Design Contradiction:
Adaptability or versatilityVSLoss of time

Solution Approach 1:

The patent employs self-service by using the compounds' own crystallization behavior to generate and characterize multiple forms. The different crystalline forms naturally exhibit different properties that can be measured and compared, allowing the system to identify optimal forms without extensive external intervention or complex characterization methodologies.

Inventive Principle:
Principle #25Self-service

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

Crystalline Form A provides improved chemical and physical stability, enabling effective pharmaceutical compositions and treatments for tumors and cancers, particularly desmoid tumors, multiple myeloma, and Notch pathway gene-mutated cancers, with enhanced safety and efficacy.

Implementation Method 1

crystalline Form A, characterized by distinct XRPD patterns and thermal stability, which addresses the balance of properties for pharmaceutical formulations, including anhydrous Form A with a melting point of about 254 °C

Methodology Applied
Scientific EffectThermal stability:

Implementation Method 2

crystalline Form A, wherein Form A is characterized by an XRPD pattern having peaks at 8.8 ± 0.2, 9.8 ± 0.2, and 23.3 ± 0.2 degrees two theta

Methodology Applied
Scientific EffectX-ray diffraction: X-Ray

Data Source

PatentEP4010322B1Solid state forms of (s)-2-(((s)-6,8-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amino)-n-(1-(2-methyl-1-(neopentylamino)propan-2-yl)-1h-imidazol-4-yl)pentanamide and uses thereof
Publication Date: 2025.11.05 PFIZER INC
  • EP4010322B1 patent drawingFigure 1
  • EP4010322B1 patent drawingFigure 2
  • EP4010322B1 patent drawingFigure 3

AI summary

The present disclosure relates to: a) solid state forms of hydrobromide salts of Compound 1; b) pharmaceutical compositions comprising one or more solid state forms of hydrobromide salts of Compound 1, and, optionally, a pharmaceutically acceptable carrier; c) methods of treating tumors or cancers by administering one or more solid state forms of hydrobromide salts of Compound 1 to a subject in need thereof; and d) methods for the preparation of solid state forms of Compound 1.