CDB-4124 Crystalline Form A Purification via Phase Transition

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Solution Overview

Problem

The existing preparation processes for 17α-acetoxy-21-methoxy-11β-[4-N,N-dimethylaminophenyl]-19-norpregna-4,9-diene-3,20-dione (CDB-4124) result in amorphous forms that are difficult to crystallize, leading to expensive and inefficient purification, poor chemical stability, and challenging handling and storage, making them unsuitable for pharmaceutical use.

Innovation Solution

A chemically and physically stable crystalline form, known as anhydrate Form A, is produced by dissolving CDB-4124 in C1-C4 alcohols or open chain ethers, with or without water, and crystallizing between -20°C to 40°C, followed by filtration and drying, which allows for efficient purification and improved handling properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If chromatographic purification is used to purify the crude product, then purity is improved, but manufacturing cost and process complexity increase significantly

Engineering Contradiction:
ImprovepurityVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent changes the physical state parameter of the product from amorphous to crystalline form. This phase change enables the product to be purified by simple filtration and drying operations instead of requiring complex chromatographic purification, thereby resolving the contradiction between purity and process complexity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention utilizes the phase transition from amorphous to crystalline state of CDB-4124. The crystalline form exhibits superior filterability and drying characteristics, allowing purification through filtration and drying rather than chromatography, thus reducing process complexity while maintaining high purity

Inventive Principle:
Principle #36Phase transitions

2Ease of manufacture

If amorphous product is produced, then production cost is reduced, but chemical stability and storage ease deteriorate

Engineering Contradiction:
Improveproduction costVSAvoidchemical stability
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The patent changes the physical state parameter from amorphous to crystalline form. This transformation improves chemical stability and storage characteristics while maintaining ease of manufacture through simple filtration and drying operations, thereby resolving the contradiction between production cost and chemical stability

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If amorphous product with small grain size is produced, then production is simplified, but filtration difficulty and handling challenges increase

Engineering Contradiction:
Improveproduction simplicityVSAvoidfiltration ease
Core Design Contradiction:
Ease of manufactureVSEase of operation

Solution Approach 1:

The patent changes the physical state parameter from amorphous to crystalline form. The crystalline product exhibits large grain size and excellent filterability, allowing easy filtration and handling while maintaining production simplicity through straightforward crystallization, filtration, and drying operations

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention utilizes the phase transition from amorphous to crystalline state, which fundamentally improves the product's physical properties including grain size and filterability. This enables easy filtration and handling operations while keeping the manufacturing process simple and straightforward

Inventive Principle:
Principle #36Phase transitions

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 form achieves excellent purity and stability, enabling more economical large-scale production with rapid filtration and drying, and maintains stability under various humidity conditions, enhancing its pharmaceutical properties.

Implementation Method 1

dissolving CDB-4124 in C1-C4 alcohols or open chain ethers

Methodology Applied
Scientific EffectDissolution: Solvation

Implementation Method 2

crystallizing between -20°C to 40°C

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Implementation Method 3

A chemically and physically stable crystalline form, known as anhydrate Form A, is produced by dissolving CDB-4124

Methodology Applied
Scientific EffectPhase change: Phase Change

Data Source

PatentEP2408799B1Novel crystalline form of antiprogestin CDB-4124
Publication Date: 2015.07.01 RICHTER GEDEON NYRT
  • EP2408799B1 patent drawingFigure 1
  • EP2408799B1 patent drawingFigure 2
  • EP2408799B1 patent drawingFigure 3

AI summary

The present invention relates to novel crystalline Form A of 17a-acetoxy-21-methoxy- l lß-[4-N,N-dimethylaminophenyl]-19-norpregna-4,9-diene-3,20-dione, (also known as CDB-4124) and methods for the preparation of it in excellent purity.