144809-28-9

Usage

Uses

Used in Pharmaceutical Industry:
5-4-[2-(5-Ethyl-2-pyridinyl)ethoxyl]benzyldene-2,4-thiazolidinedione is used as a novel intermediate for the synthesis of Pioglitazone (P471000), a medication prescribed for managing type 2 diabetes. Its role in the pharmaceutical industry is crucial, as it contributes to the development and production of an essential drug for diabetes treatment.
Used in Research and Development:
In addition to its application in the pharmaceutical industry, 5-4-[2-(5-Ethyl-2-pyridinyl)ethoxyl]benzyldene-2,4-thiazolidinedione is also utilized in research and development for exploring new therapeutic applications and potential improvements in drug design. Its unique chemical structure allows scientists to investigate its properties and interactions with biological systems, potentially leading to the discovery of new drugs or treatment methods.
Used in Quality Control and Impurity Profiling:
As Pioglitazone EP Impurity B, 5-{4-[2-(5-Ethyl-2-pyridinyl)ethoxyl]benzyldene}-2,4-thiazolidinedione is essential for quality control and impurity profiling in the manufacturing process of Pioglitazone. It helps ensure the safety, efficacy, and purity of the final drug product by monitoring and controlling the presence of impurities during production. This application is vital for maintaining the overall quality and reliability of the medication.

InChI:InChI=1/C19H18N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,11-12H,2,9-10H2,1H3,(H,21,22,23)/b17-11+

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 114393-97-4 4-[2-(5-ethylpyridyl)ethoxy]benzaldehyde 
• 110-89-4 piperidine 
• 646519-94-0 5-{4-[2-chloro-2-(5-ethylpyridn-2-yl)ethoxy]benzylidene}-2,4-thiazolidene dione 
• 5223-06-3 5-ethyl-2-(2-hydroxyethyl)pyridine 
• 90643-32-6 2-(5-ethyl-1-oxypyridin-2-yl)ethanol 
• 646519-82-6 5-ethyl-2-[2-oxo-(1,3,2)dioxathiolan-4-yl]pyridine 
• 123-08-0 4-hydroxy-benzaldehyde 
• 646519-88-2 5-{4-[2-chloro-2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-2,4-thiazolidene dione 
• 101931-00-4 5-{4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione 
• 646519-81-5 2-bromo-1-(5-ethylpyridin-2-yl)ethanol 
• 646519-84-8 5-{4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]benzylidene}-2,4-thiazolidene dione 
• 5408-74-2 5-ethyl-2-vinyl-pyridine 
• 471295-98-4 4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]benzaldehyde 

Downstream Products

• 105355-27-9 Pioglitazone 
• 112529-15-4 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride 

Relevant academic research and scientific papers

NOVEL PROCESS TO PREPARE PIOGLITAZONE VIA SEVERAL NOVEL INTERMEDIATES

A novel process for preparing thiazolidinediones, preferably Pioglitazone, as described. Also described are novel intermediates involved in its synthesis and process for their preparation and use in medicine.

An improved process for pioglitazone and its pharmaceutically acceptable salt

An improved process for pioglitazone (1) is described. The process features high-yielding transformations employing inexpensive reagents and recoverable solvents.

PROCESS FOR THE SYNTHESIS OF PIOGLITAZONE HYDROGEN CHLORIDE

The invention relates to a process for the synthesis of pioglitazone hydrogen chloride - which is an antidiabetic drug - via novel intermediates by reacting 4-[2-(5-ethyl-2-pyridinyl)-ethoxy]-benzaldehyde salt of formula (II), wherein HX is: HCI, CF3COOH, C4H4O4, (COOH)2 with a base and then thiazolidine-2,4-dione, and the obtained 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methylene]-2,4-thiazolidinedione base is treated with hydrochloric acid and the obtained 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl] methylene]-2,4-tiazolidinedione hydrogen chloride of formula(III) is hydrogenated in the presence of a catalyst. Further objects of the invention are the salts of general formula (II) and the benzylidene derivative of formula (III).

Method for producing ethers

A compound of the formula: [wherein A stands for an aromatic ring residue, a group shown by R1 --CO-- (wherein R1 stands for an aliphatic hydrocarbon residue, aromatic hydrocarbon residue, a heterocyclic residue, an aromatic alipahtic hydrocarbon residue or an alicyclic hydrocarbon residue) or R2 --CH=CH-- (wherein R2 stands for an aliphatic hydrocarbon residue an aromatic hydrocarbon residue a heterocyclic residue an aromatic aliphatic hydrocarbon residue or an alicyclic hydrocarbon residue), and B stands for an aromatic ring residue], can be obtained in high yield, at high purity level by short reaction time, by reacting a compound of the formula: (wherein A is of the same meaning as defined above, and X stands for a leaving group) with a compound represented by the general formula: (wherein M stands for an alkali metal atom or an alkaline earth metal atom and B is of the same meaning as defined above) in a non-aqueous solvent.

Method for producing thiazolidinedione derivatives

A compound of the formula: STR1 (wherein R1 is hydrogen or a lower alkyl) can be produced advantageously by (1) reacting a compound of the formula: STR2 (wherein R1 has a meaning given above) with a halogenating agent or sulfonyl halide to give a compound of the formula: STR3 (wherein R1 has a meaning given above and X is a halogen or an alkyl- or aryl-sulfonyloxy), (2) reacting the resulting compound with a compound of the formula: STR4 to give a compound of the formula: (wherein R1 has the meaning given above), (3) reacting the resulting compound with a compound of the formula: STR5 to give a compound of the formula: STR6 (wherein R1 has the meaning given above), and (4) subjecting the resulting compound to catalytic reduction.