Amorphous Saroglitazar Magnesium Synthesis Process

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Solution Overview

Problem

Current methods for preparing saroglitazar are not efficient, economical, or environmentally friendly, and they often result in crystalline forms that have stability and bioavailability issues due to variations in physical properties among polymorphs, which can affect pharmaceutical parameters like storage, stability, and bioavailability.

Innovation Solution

A process involving the reaction of a hydroxy compound with a mesylate compound in the presence of a base and a phase transfer catalyst in a specific solvent mixture, followed by hydrolysis and conversion with a magnesium source to obtain a substantially amorphous form of saroglitazar magnesium, which is more stable and bioavailable.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional methods are used to prepare saroglitazar, then the synthesis process is established, but the process is not efficient, economical, or environmentally friendly and produces crystalline forms with stability and bioavailability issues

Engineering Contradiction:
Improvesynthesis efficiencyVSAvoidproduct stability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent changes the physical state parameter of the product from crystalline to amorphous form. This is achieved by modifying the synthesis process parameters including using a mixture of organic solvents (cyclohexane with alcohols, ketones, esters, chlorinated hydrocarbons, or ethers), controlling reaction temperature (35-85°C), and using specific bases and phase transfer catalysts. These parameter changes result in the formation of amorphous saroglitazar magnesium which has improved stability and bioavailability compared to conventional crystalline forms

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite system by forming a salt between saroglitazar and magnesium. This saroglitazar magnesium salt is prepared through reaction with a magnesium source and exhibits superior properties compared to the free acid form. The composite material approach addresses both the synthesis efficiency and product stability issues simultaneously

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If crystalline forms of saroglitazar are produced, then the product can be manufactured, but variations in physical properties among polymorphs affect storage, stability, and bioavailability

Engineering Contradiction:
ImprovemanufacturabilityVSAvoidphysical property consistency
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent fundamentally changes the physical state parameter from crystalline to amorphous, eliminating polymorphism issues. The amorphous form is achieved through specific process parameters including solvent selection (cyclohexane mixed with various organic solvents), temperature control (35-85°C), and the use of phase transfer catalysts. This parameter change ensures consistent physical properties and eliminates the variability associated with different crystal polymorphs while maintaining ease of manufacture

Inventive Principle:
Principle #35Parameter changes

3Productivity

If conventional synthesis processes are used, then saroglitazar can be produced, but the processes are not environmentally friendly and lack economy

Engineering Contradiction:
Improveproduction outputVSAvoidenvironmental impact
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent modifies process parameters to improve environmental performance including using environmentally benign organic solvents (avoiding highly toxic solvents), optimizing reaction temperature (35-85°C) to reduce energy consumption, and implementing a streamlined synthesis route. These changes maintain high productivity while reducing environmental impact and production costs

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs readily available and inexpensive reagents including common organic solvents, standard bases (such as sodium hydroxide, potassium hydroxide, lithium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate), and conventional phase transfer catalysts. This approach reduces material costs and makes the process more economical while maintaining high productivity

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

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 process yields a high-purity, amorphous form of saroglitazar magnesium with improved stability, solubility, and bioavailability, meeting regulatory requirements and ensuring consistent pharmaceutical performance.

Implementation Method 1

hydrolyzing the alkoxy ester compound of Formula (II) with a base to obtain saroglitazar

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 2

reacting a hydroxy compound (A) with a mesylate compound (A1) in a mixture of organic solvents in the presence of a base and a phase transfer catalyst

Methodology Applied
Scientific EffectPhase transfer catalysis:

Data Source

PatentEP3004053B1A process for preparation of pyrroles having hypolipidemic hypocholesteremic activities
Publication Date: 2021.03.24 ZYDUS LIFESCIENCES LTD
  • EP3004053B1 patent drawingFigure 1
  • EP3004053B1 patent drawingFigure 2
  • EP3004053B1 patent drawingFigure 3

AI summary

The present invention provides pyrroles having hypolipidemic hypocholesteremic activities. The invention provides saroglitazar and its pharmaceutically acceptable salts, hydrates, solvates, polymorphs or intermediates thereof. The invention also provides a process for the preparation of saroglitazar. The invention further provides intermediates as well process for preparation thereof.