105355-27-9

Usage

Clinical Use

Treatment of type 2 diabetes mellitus

Drug interactions

Potentially hazardous interactions with other drugs None known

Metabolism

Pioglitazone undergoes extensive hepatic metabolism by hydroxylation mainly via cytochrome P450 2C8 to form active and inactive metabolites. Three of the six identified metabolites are active (M-II, M-III, and M-IV). Following oral administration of radiolabelled pioglitazone to man, recovered label was mainly in faeces (55%) and a lesser amount in urine (45%).

InChI:InChI=1/C19H20N2O3S.ClH/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;/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23);1H

Upstream product

• 5223-06-3 5-ethyl-2-(2-hydroxyethyl)pyridine 
• 136401-69-9 5-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]benzylidene}-2,4-thiazolidinedione 
• 19842-08-1 2-bromo-5-ethylpyridine 
• 81675-78-7 4-(vinyloxy)benzaldehyde 
• 1574532-69-6 Sodium (4-(2-(5-ethylpyridin-2-yl)ethoxy)phenyl)(hydroxy)methanesulfonate 
• 144809-27-8 toluene-4-sulfonic acid 2-(5-ethylpyridin-2-yl)ethyl ester 
• 646519-82-6 5-ethyl-2-[2-oxo-(1,3,2)dioxathiolan-4-yl]pyridine 
• 90643-32-6 2-(5-ethyl-1-oxypyridin-2-yl)ethanol 
• 646519-94-0 5-{4-[2-chloro-2-(5-ethylpyridn-2-yl)ethoxy]benzylidene}-2,4-thiazolidene dione 
• 646519-92-8 5-{4-[2-(5-ethylpyridin-2-yl)-2-tosylethoxy]benzylidene}-2,4-thiazolidene dione 
• 646519-90-6 5-{4-[2-(5-ethylpyridin-2-yl)-2-mesylethoxy]benzylidene}-2,4-thiazolidene dione 
• 105355-25-7 methyl 2-bromo-3-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]phenyl}propionate 
• 17356-08-0 thiourea 
• 74772-78-4 5-(4-hydroxybenzyl)-2,4-thiazolidinedione 

Downstream Products

• 952188-00-0 5-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]benzyl}-3-[2-(5-ethyl-pyridin-2-yl)ethyl]-1,3-thiazolidine-2,4-dione 
• 16106-44-8 potassium tosylate 
• 1450912-73-8 C₂₆H₃₁F₂N₅O₃S 
• 1351955-20-8 (2-nitroxyethyl)carbamic acid 5-(4-[(2-ethylpyridin-2-yl)ethoxy]benzyl)-2,4-dioxothiazolidin-3-ylmethyl ester 

Relevant academic research and scientific papers

Practical synthesis of pioglitazone: Ligand substitution reaction with oxido vanadium(IV) and biological activity

The authors performed two types of experiments: the reduction of 5-{4-[2-(5-ethyl-2-pyridyl)etoxy]benzilidine}-2-4-thiazolidinedione to pioglitazone (5-{4-[2-(5-ethyl-2-pyridyl) etoxy]benzil}-2-4-thiazolidinedione) with magnesium/methanol and the synthesis of an oxidovanadium(IV) complex of pioglitazone in methanol under refluxing conditions. The structures of pioglitazone and its oxidovanadium(IV) complex were analyzed by using physicochemical and spectroscopic techniques. Comparisons of the spectral measurements of pioglitazone with those of its oxidovanadium(IV) ion complex are useful in determining the atoms of the ligand that are coordinated to the metal ion. In addition, antibacterial and antifungal activities of the complex were studied and the complex is screened against bacteria and fungi.

Hydrogenation of 5-alkylidene-2,4-thiazolidiones on Pd/C catalysts under mild conditions: An alternative synthesis route to pioglitazone

The hydrogenation of 5-alkylidene-2,4-thiazolidiones was studied using Pd/C to establish an alternative process for pioglitazone synthesis. The reportedly sluggish reactivity was due to the high reaction temperature in formic acid. The conditions were improved to 1 atm at 296 K, which results in a quantitative product with a smaller amount of the catalyst. Graphical Abstract: [Figure not available: see fulltext.]

Recoverable, Reusable, Highly Active, and Sulfur-Tolerant Polymer Incarcerated Palladium for Hydrogenation

A new type of immobilized palladium, PI (polymer incarcerated) Pd (2b), from Pd(PPh3)4 and copolymer (1b) has been developed. The excellent activity of PI Pd has been demonstrated in hydrogenation of various olefins, benzyl ethers, and nitro and aromatic compounds. PI Pd is tolerant under high pressure and high temperature and can be recovered and reused several times without loss of activity even under harsh conditions. Moreover, PI Pd is highly resistant to poisoning by sulfur.

Radical Hydroarylation of Functionalized Olefins and Mechanistic Investigation of Photocatalytic Pyridyl Radical Reactions

We report the photoredox alkylation of halopyridines using functionalized alkene and alkyne building blocks. Selective single-electron reduction of the halogenated pyridines provides the corresponding heteroaryl radicals, which undergo anti-Markovnikov addition to the alkene substrates. The system is shown to be mild and tolerant of a variety of alkene and alkyne subtypes. A combination of computational and experimental studies support a mechanism involving proton-coupled electron transfer followed by medium-dependent alkene addition and rapid hydrogen atom transfer mediated by a polarity-reversal catalyst.

Phosphoryl chloride mediated synthesis of 5-arylidene-2,4- thiazolidinediones derivatives via aromatic bisulfite adducts

The carbon-carbon bond formation by the condensation of bisulfite adduct of aromatic aldehydes with thiazolidine-2, 4-dione to furnish 5-arylidene-2,4- thiazolidinedione's has been investigated. This novel methodology was applied to convert substituted aryl bisulfite adducts to corresponding 5-arylidene-2,4-thiazolidinedione's with POCl3 in less-polar solvents such as toluene, chlorobenzene and o-xylene. 5-(4-methoxybenzylidene) thiazolidine-2,4-dione and 5-(4-ethoxybenzylidene)thiazolidine-2,4-dione were obtained in good yields.

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.

Glycation Cross-link Breakers to Increase Resistance to Enzymatic Degradation

The present invention relates to a method to treat a grafts, implant, scaffold, and constructs, including allografts, xenografts, autografts, and prosthetics comprising collagen, with an inhibitor of collagen cross-links and/or advanced glycation endproducts (AGE), in order to alleviate the mechanical weakness induced by the cross-links The invention also provides for kits for use in the operating theater during autograft, allograft or xenograft procedures, or for preparing allograft, xenografts or prosthetics that have not been already treated prior to packaging. The kit comprises a first agent or agents that inhibit collagen cross-links and/or advanced glycation endproducts, instructions for use, optionally a wash or rinse agent, and a device for containing the graft and first agent.

PHARMACEUTICAL COMPOSITIONS CONTAINING A BIGUANIDE AND A THIAZOLIDINEDIONE

The present invention relates to pharmaceutical compositions that include a combination of a biguanide present in an extended-release form and a thiazolidinedione present in an immediate-release form. The present invention further relates to the processes for preparing such compositions.

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.

5-(4-HYDROXYBENZYL)THIAZOLIDINE-2,4-DIONE AS INTERMEDIATE FOR SYNTHESIS OF THIAZOLIDINEDIONE BASED COMPOUNDS AND PROCESS FOR PREPARING THE SAME

The present invention relates to 5-(4-hydroxybenzyl)thiazolidine-2,4-dione represented by the following Chemical Formula [1], which is useful as an intermediate for synthesis of thiazolidinedione based compounds, a method for preparing the compound, and a method for preparing pioglitazone or pioglitazone hydrochloride, which is a thiazolidinedione based drug and useful in treating and preventing diabetes, using the 5-(4-hydroxybenzyl)thiazolidine-2,4-dione represented by Chemical Formula [1] as an intermediate: