495399-09-2

Basic information

• Product Name: Saroglitazar
• Synonyms: Saroglitazar
• CAS NO: 495399-09-2
• Molecular Formula: C25H29NO4S
• Molecular Weight: 439.56706
• Mol File: 495399-09-2.mol

Chemical Properties

• Boiling Point: 621.0±55.0 °C(Predicted)
• Appearance: /
• Density: 1.15±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 3.60±0.10(Predicted)
• CAS DataBase Reference: Saroglitazar(CAS DataBase Reference)
• NIST Chemistry Reference: Saroglitazar(495399-09-2)
• EPA Substance Registry System: Saroglitazar(495399-09-2)

Safety Data

• Hazardous Substances Data: 495399-09-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Saroglitazar is used as a therapeutic agent for the treatment of diabetic dyslipidemia and hypertriglyceridemia in patients with Type 2 diabetes mellitus not controlled by statin therapy. It improves insulin sensitivity, decreases serum triglyceride, free fatty acid, and glucose levels, and reduces LDL levels in various animal models.
Used in Research and Development:
Saroglitazar is used as a research compound for studying the effects of PPARα and PPARγ agonism on metabolic disorders and the development of new drugs targeting these pathways.
Used in Nonsteroidal Anti-inflammatory Drug (NSAID) Preparation:
Saroglitazar is used as a chemical intermediate in the synthesis of NSAIDs, contributing to the development of new anti-inflammatory medications.

Originator

Cadila Healthcare Ltd. (India)

Synthesis

The sequence began with a Paal–Knorr pyrrole synthesis starting from commercial 1-[4-(methylthio)phenyl]pentane-1,4-dione (148). Subjection of this diketone to ethanolamine in warm pivalic acid furnished pyrrole 149, which was taken forward as the crude product. Next, the alcohol was mesylated to afford 150, which was used without further purification. Williamson ether conditions were employed to convert mesylate 150 to the corresponding aryl ether 152 through the use of commercial phenol 151 and anhydrous potassium carbonate. This reaction proceeded in 80% yield. Saponification of the terminal ethyl ester using sodium hydroxide followed by acidic pH adjustment ultimately delivered the carboxylic acid drug saroglitazar (XX) in 98% yield from 152.

Upstream product

• 1392592-61-8 (S)-(-)α-1-phenylethylamine salt of (S)-α-ethoxy-4-[2-[-methyl-5-[4-(methylthio) phenyl]-1H-pyrrol-1-yl]ethoxy]benzene-propanoic acid 
• 222555-06-8 ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate 
• 494850-87-2 methanesulfonic acid 2-[2-methyl-5-(4-methylsulfanyl-phenyl)-pyrrol-1-yl]-ethyl ester 

Downstream Products

• 1064453-40-2 (S)-2-ethoxy-3-(4-(2-(2-methyl-5-(4-(methylthio)phenyl)-1H-pyrrol-1-yl)ethoxy)phenyl)propanoic acid sodium salt 
• 1392592-60-7 (S)-α-ethoxy-4-[2-[-methyl-5-[4-(methylthio)phenyl]-1H-pyrrol-1-yl]ethoxy]benzenepropanoic acid potassium salt 

Relevant articles and documents

NOVEL SALTS, CRYSTALLINE FORMS AND PREMIX OF HYPOLIPIDEMIC AGENT

Present invention relates to novel salts of saroglitazar and certain polymorphic forms of saroglitazar salts. Invention provides process for the preparation of novel salts and polymorphic forms of saroglitazar. Invention also provides novel co-precipitants or premixes of saroglitazar with pharmaceutically acceptable excipients/secondary therapeutic agent and process for the preparing same.

SYNERGISTIC COMPOSITIONS

The present invention describes a synergistic composition comprising of one or more statins, or one or more dipeptidyl peptidase IV (DPP IV) inhibitor or one or more biguanide antihyperglycaemic agent and a PPAR agonist of formula (la) for the treatment of diabetes, especially non-insulin dependent diabetes (NIDDM) or Type 2 diabetes and conditions associated with diabetes mellitus and to compositions suitable for use in such method. The invention also describes the preparation of such compositions. The present invention also relates to certain novel salts of the PPAR agonist of formula (I), processes for the preparation of : these novel salts and use thereof.

POLYMORPHIC FORM OF PYRROLE DERIVATIVE AND INTERMEDIATE THEREOF

The present invention relates to Saroglitazar free acid of Formula (IA) or its pharmaceutically acceptable salts, pharmaceutically acceptable solvates, pharmaceutically acceptable esters, stereoisomers, tautomers, analogs and derivatives thereof. The present invention also provides an amorphous form of saroglitazar free acid and processes of preparation thereof. The present invention also provides pharmaceutical composition comprising an amorphous form saroglitazar magnesium.

AN IMPROVED PROCESS FOR THE PREPARATION OF PYRROLE DERIVATIVES

The present invention relates to an improved process for the preparation of pyrroles derivatives having hypolipidemic and hypocholesteremic activities. In particular, the invention relates to an improved process for the preparation of 2- ethoxy-3-(4-(2-(2-methyl-5-(4-(methylthio)phenyl)-1H-pyrrol-1-yl)ethoxy) phenyl)propanoate and its pharmaceutically acceptable salts, hydrates, solvates, polymorphs or intermediates thereof. The invention also relates to an improved process for the preparation of mesylate compound (A1).

Novel heterocyclic compounds having hypolipidemic, hypocholesteremic activities process for their preparation and pharmaceutical compositions containing them and their use in medicine

Novel β-aryl-α-substituted propanoic acids having hypolipidemic and hypocholesteremic activities.