Crystalline 5-cyclopropyl-2-((1-(3-fluorobenzyl)-1H-indol-5-yl)amino)nicotinic acid

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Solution Overview

Problem

The existing production method for 5-cyclopropyl-2-((1-(3-fluorobenzyl)-1H-indol-5-yl)amino)nicotinic acid results in an amorphous form that lacks stability and practicality as an active pharmaceutical ingredient.

Innovation Solution

The development of crystalline forms of the compound, specifically the α-form and β-form, which exhibit distinct diffraction peaks in powder x-ray diffraction and are produced through heat-dissolving and cooling processes using specific solvents, enhancing stability and handling properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If the compound is produced according to the production method described in Patent Document 1, then the compound can be obtained, but it exists in an amorphous form with poor stability

Engineering Contradiction:
ImprovestabilityVSAvoidamorphous form stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent applies parameter changes by modifying the crystallization conditions including solvent selection (water, alcohols, ethers, esters, ketones, or their mixtures), temperature parameters (cooling rates from room temperature to 0-4°C), and pH control during the crystallization process to transform the amorphous compound into stable crystalline forms with defined diffraction patterns

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent utilizes phase transitions by inducing crystallization from the amorphous state through controlled cooling of saturated solutions, transforming the compound into stable crystalline forms (α-form, β-form, or γ-form) with distinct powder diffraction patterns and improved stability properties

Inventive Principle:
Principle #36Phase transitions

2Ease of manufacture

If the compound is produced in amorphous form, then production is simpler, but handling and pharmaceutical application become difficult

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

Solution Approach 1:

The patent maintains production simplicity while improving handling ease by implementing a straightforward crystallization process involving dissolution in hot solvent followed by controlled cooling to 0-4°C, which transforms the amorphous compound into stable crystalline forms that are easier to handle, store, and apply pharmaceutically

Inventive Principle:
Principle #36Phase transitions

3Reliability

If crystalline forms are developed, then stability and handling improve, but the production process becomes more complex

Engineering Contradiction:
ImprovestabilityVSAvoidproduction process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent manages production process complexity by systematically optimizing parameters such as solvent selection, saturation temperature, cooling rate, and pH control to achieve stable crystalline forms through a controlled but manageable process that balances complexity with improved product stability

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 α-form and β-form crystals demonstrate improved stability and ease of handling, making them suitable as active pharmaceutical ingredients with enhanced solubility and physical stability.

Implementation Method 1

a step of heat-dissolving a suspension containing 5-cyclopropyl-2-((1-(3-fluorobenzyl)-1H-indol-5-yl)amino)nicotinic acid and at least one solvent selected from alcohols, ethers, ketones and esters

Methodology Applied
Scientific EffectDissolution: Solvation

Implementation Method 2

a step of cooling the solution obtained in (1), wherein the alcohols are methanol, ethanol, propanol, 2-propanol or butanol

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Data Source

PatentEP3345898B1Crystals of 5-cyclopropyl-2-((1-(3-fluorobenzyl)-1h-indol-5-yl)amino)nicotinic acid
Publication Date: 2020.05.06 FUJIFILM TOYAMA CHEMICAL CO LTD
  • EP3345898B1 patent drawingFigure 1~2
  • EP3345898B1 patent drawingFigure 3~4
  • EP3345898B1 patent drawingFigure 5~6

AI summary

Crystals of 5-cyclopropyl-2-((1-(3-fluorobenzyl)-1H-indol-5-yl)amino)nicotinic acid having diffraction peaks at diffraction angles (2θ) of 12.2±0.2, 17.2±0,2, 19.4±0.2, 24.1±0.2, and 27.1±0.2° or diffraction angles (2θ) of 12.9±0.2, 15.5±0.2, 21.2±0.2, 21.7±0.2, and 25.9±0.2° in powder x-ray diffraction have excellent stability, are easy to handle, and are useful as a drug substance of pharmaceuticals to be used in treatments such as the prevention or treatment of diseases involving keratinocyte hyperproliferation.