Crystalline Form R for Stable Purification of Pyridazine Carboxamide

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Solution Overview

Problem

Existing methods for isolating and purifying 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)phenyl)amino)-N-(methyl-d3)pyridazine-3-carboxamide for pharmaceutical use face challenges in reproducibility, stability, and the ability to convert to other solid forms, with a need for a crystalline form that is physically and chemically stable and amenable to further processing.

Innovation Solution

The development of crystalline forms such as Form R, which are characterized by specific X-ray diffraction patterns and thermal properties, allowing for reproducible production and conversion to other solid forms, ensuring stability and suitability for pharmaceutical formulations.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional isolation and purification methods are used, then the compound can be obtained as a solid, but the yield loss is significant and reproducibility is poor

Engineering Contradiction:
Improveisolation and purification efficiencyVSAvoidyield loss
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent applies parameter changes by optimizing crystallization conditions including temperature gradients, solvent composition ratios, and pH levels to achieve reproducible formation of crystalline Form R with minimal yield loss during isolation and purification

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent utilizes phase transitions through controlled crystallization processes where the compound transitions from solution phase to solid crystalline phase (Form R), enabling efficient separation and purification with high recovery yields

Inventive Principle:
Principle #36Phase transitions

2Ease of manufacture

If the solid form is not stable, then processing is easier, but physical and chemical stability upon storage at different conditions is compromised

Engineering Contradiction:
Improveprocessing capabilityVSAvoidphysical and chemical stability
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The patent optimizes crystallization parameters including temperature, pressure, and solvent selection to produce crystalline Form R with enhanced physical and chemical stability while maintaining amenability to pharmaceutical processing operations

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent develops crystalline Form R as a stable solid form that can be combined with pharmaceutically acceptable excipients to create stable pharmaceutical compositions suitable for various storage conditions

Inventive Principle:
Principle #40Composite materials

3Ease of manufacture

If a single crystalline form is produced, then purification is simplified, but the ability to convert to other solid forms is limited

Engineering Contradiction:
Improvepurification simplicityVSAvoidconversion to other solid forms
Core Design Contradiction:
Ease of manufactureVSAdaptability or versatility

Solution Approach 1:

The patent produces crystalline Form R as a preliminary stable intermediate form that can be subsequently converted to other solid forms including amorphous forms or different crystalline polymorphs depending on the desired final product requirements

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent establishes crystalline Form R as a dynamic platform form that can be transformed into different solid states through controlled processing conditions, providing versatility for various pharmaceutical formulation needs

Inventive Principle:
Principle #15Dynamics

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 crystalline forms provide a stable and reproducible solid form of the compound, enabling efficient isolation and purification with minimal yield loss, and facilitating conversion to other forms, enhancing physiochemical properties and processing capabilities.

Implementation Method 1

characterized by a powder X-ray diffraction pattern comprising peaks at 2θ values of approximately 9.5, 10.0, 16.4, 17.2, 22.0, and 22.8 degrees

Methodology Applied
Scientific EffectX-ray diffraction: X-Ray

Implementation Method 2

The crystalline form is characterized by thermal analysis data showing specific melting and phase transition behaviors

Methodology Applied
Scientific EffectDifferential scanning calorimetry: Calorimetry

Data Source

PatentEP4387968B1Crystal forms of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1h-1,2,4-triazol-3-yl)phenyl)amino)-n-(methyl-d3)pyridazine-3-carboxamide
Publication Date: 2025.11.12 BRISTOL MYERS SQUIBB CO
  • EP4387968B1 patent drawingFigure 1
  • EP4387968B1 patent drawingFigure 2
  • EP4387968B1 patent drawingFigure 3

AI summary

Described herein are a number of crystalline forms of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)phenyl) amino)-N-(methyl-d3)pyridazine-3-carboxamide: Form L, Form M, Form N, Form O, Form P, Form Q, Form R, Form S, Form T, Form U, Form V, Form W, Form X, Form Y, Form Z, Form AA, Form AB, Form AC, Form AD, Form AE, Form AF, and Form AG, together with characterization data for each of these crystalline forms.