Romidepsin Crystalline Forms Stability Optimization

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Solution Overview

Problem

Current methods for producing romidepsin lack efficiency in producing crystalline forms with specific characteristics, which are crucial for pharmaceutical applications due to variations in stability, bioavailability, and therapeutic efficacy.

Innovation Solution

Development of methods to prepare and characterize crystalline forms C, D, E, F, H, I, J, K, L, and N of romidepsin, along with its amorphous form, using techniques such as XRPD, DSC, TGA, and FT-IR to ensure consistent production and identification of these forms.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional production methods are used, then romidepsin can be produced, but the crystalline forms lack consistent stability and bioavailability characteristics

Engineering Contradiction:
ImprovestabilityVSAvoidproduction efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent applies parameter changes by optimizing crystallization conditions including solvent selection (acetone, ethyl acetate, isopropyl alcohol), temperature control (0-25°C), pH adjustment (pH 2-8), and evaporation rate control to produce specific crystalline forms (C, D, E, F, H, I, J, K, L, N) with enhanced stability and bioavailability characteristics

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent utilizes phase transitions during the crystallization process, transforming romidepsin from amorphous or solution state into defined crystalline forms through controlled evaporation, cooling, and solvent removal, which enhances the reliability of the product

Inventive Principle:
Principle #36Phase transitions

2Manufacturing precision

If multiple crystalline forms are produced, then bioavailability and therapeutic efficacy are enhanced, but the manufacturing process becomes more complex

Engineering Contradiction:
Improvecrystalline form consistencyVSAvoidproduction method complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent employs systematic parameter changes including pH adjustment (pH 2-8), temperature control (0-25°C), solvent selection (acetone, ethyl acetate, isopropyl alcohol, dichloromethane), and evaporation rate control to precisely control crystallization and produce consistent crystalline forms with defined characteristics

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent implements feedback mechanisms through characterization techniques (XRPD, DSC, TGA, FT-IR, NMR) to monitor and verify the formation of specific crystalline forms, allowing adjustment of crystallization parameters to achieve desired manufacturing precision and consistency

Inventive Principle:
Principle #23Feedback

3Reliability

If crystallization conditions are optimized, then stability is improved, but the production time increases

Engineering Contradiction:
ImprovebioavailabilityVSAvoidcrystallization time
Core Design Contradiction:
ReliabilityVSLoss of time

Solution Approach 1:

The patent utilizes controlled phase transitions during crystallization, including solvent evaporation, cooling crystallization, and pH-induced precipitation, which accelerate the formation of stable crystalline forms while maintaining bioavailability characteristics

Inventive Principle:
Principle #36Phase transitions

Solution Approach 2:

The patent employs periodic action through controlled evaporation cycles, temperature fluctuations (0-25°C), and pH adjustments during crystallization to promote rapid formation of stable crystalline forms without excessive production time

Inventive Principle:
Principle #19Periodic action

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 methods enable the production of romidepsin in stable crystalline and amorphous forms, enhancing bioavailability, stability, and therapeutic efficacy, thus improving treatment outcomes for proliferative diseases, immune-mediated diseases, and cancers.

Implementation Method 1

crystalline Form C of romidepsin comprising characteristic XRPD peaks at about 8.28, 11.45, 12.19 and 21.13 degrees 2 theta

Methodology Applied
Scientific EffectX-ray diffraction: X-Ray

Implementation Method 2

characterization by XRPD, DSC, TGA, and FT-IR

Methodology Applied
Scientific EffectCalorimetry: Calorimetry

Implementation Method 3

characterization by XRPD, DSC, TGA, and FT-IR

Methodology Applied
Scientific EffectThermogravimetric analysis:

Implementation Method 4

characterization by XRPD, DSC, TGA, and FT-IR

Methodology Applied
Scientific EffectInfrared spectroscopy: Infrared Radiation

Data Source

PatentEP2593123B1Romidepsin solid forms and uses thereof
Publication Date: 2019.09.04 CELGENE CORP
  • EP2593123B1 patent drawingFigure 1(a)
  • EP2593123B1 patent drawingFigure 1(b)
  • EP2593123B1 patent drawingFigure 1(c)

AI summary

The present disclosure provides solid forms of a compound of formula I. In some embodiments, the present disclosure provides crystalline forms of Compound I. In some embodiments, the present disclosure provides solvate forms of Compound I. In some embodiments, the present disclosure provides amorphous Compound I.