Crystalline Salt Forms for Stable Pharmaceutical Dosage

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Solution Overview

Problem

Current pharmaceutical formulations of 8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one lack stable crystalline forms suitable for solid dosage forms, leading to challenges in bioavailability, stability, and manufacturability.

Innovation Solution

Development of novel crystalline salt forms, such as maleate and camsylate salts, which are physically stable and less susceptible to hydration, allowing for controlled crystallization and improved properties in solid dosage forms, including specific polymorphic forms like maleate polymorph Form A and camsylate polymorph Form A.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If amorphous or non-crystalline forms of Compound 1 are used, then flexibility in formulation is maintained, but stability and bioavailability are compromised

Engineering Contradiction:
ImprovestabilityVSAvoidformulation complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by transforming the physical state of Compound 1 from amorphous to crystalline forms through controlled crystallization processes. Specific parameters such as temperature, solvent composition, and crystallization rate are modified to produce stable crystalline polymorphs (Forms I-IV) and solvates that exhibit improved stability and bioavailability while maintaining formulation feasibility

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite materials by forming crystalline complexes of Compound 1 with co-formers such as cyclic carbonates (ethylene carbonate, propylene carbonate) and other solvents. These composite crystalline structures combine the properties of both compounds, resulting in enhanced stability and controlled release characteristics while providing well-defined crystal lattices suitable for solid dosage forms

Inventive Principle:
Principle #40Composite materials

2Productivity

If conventional non-crystalline formulations are used, then manufacturing simplicity is maintained, but bioavailability and stability are reduced

Engineering Contradiction:
ImprovebioavailabilityVSAvoidmanufacturability
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent applies preliminary action by pre-establishing well-defined crystalline structures and polymorphic forms of Compound 1 before final formulation. The controlled crystallization process creates stable, reproducible crystal forms with predictable dissolution and bioavailability characteristics, eliminating the need for complex post-processing or stabilization steps during manufacturing

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent utilizes phase transitions by controlling the transition from liquid/solution phase to solid crystalline phase through controlled crystallization. This phase transition allows Compound 1 to form stable crystalline polymorphs and solvates with specific melting points, densities, and dissolution rates that enhance bioavailability while providing robust solid-state properties for easy manufacturing

Inventive Principle:
Principle #36Phase transitions

3Reliability

If stable crystalline forms are developed, then stability and bioavailability improve, but crystal structure control becomes more challenging

Engineering Contradiction:
ImprovestabilityVSAvoidcrystal structure control
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The patent uses co-formers such as cyclic carbonates (ethylene carbonate, propylene carbonate) and other solvents as intermediaries to mediate the crystallization of Compound 1. These intermediary substances facilitate the formation of specific polymorphic forms and solvates by acting as template molecules during crystallization, thereby controlling crystal structure while enhancing stability. The co-formers become integral parts of the crystal lattice, providing structural stability and reproducible physical properties

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent applies parameter changes by systematically varying crystallization conditions including temperature profiles, solvent composition ratios, cooling rates, and supersaturation levels to control which polymorphic form crystallizes. By adjusting these parameters, the process selectively produces desired crystal forms (Forms I-IV) with specific stabilities and dissolution rates, achieving both stability and manufacturability

Inventive Principle:
Principle #35Parameter 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 novel crystalline salt forms enhance bioavailability, stability, and manufacturability, making them suitable for bulk preparation and handling, particularly in solid dosage forms, while maintaining non-hygroscopic properties.

Implementation Method 1

controlled crystallization and improved properties in solid dosage forms

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Data Source

PatentEP2534153B2Salts and polymorphs of 8-fluoro-2-{4-[(methylamino}methyl]phenyl}-1,3,4,5-tetrahydro-6h-azepino[5,4,3-cd]indol-6-one
Publication Date: 2024.05.22 PFIZER INC
  • EP2534153B2 patent drawingFigure 1
  • EP2534153B2 patent drawingFigure 2
  • EP2534153B2 patent drawingFigure 3

AI summary

The present invention relates to novel polymorphic forms of 8-fluoro-2-{4- [(methylamino)methyl]phenyf}-1,3,4,5-tetrahydro-6H-azepino(5,4,3-cd]indol-6-one;(I), and to processes for their preparation. Such polymorphic forms may be a component of a pharmaceutical composition and may be used to treat a mammalian disease condition mediated by poly(ADP-ribose) polymerase activity including the disease condition such as cancer.