85583-54-6

Usage

Chemical Properties

Pale Yellow Solid

Uses

Different sources of media describe the Uses of 85583-54-6 differently. You can refer to the following data:
1. Pioglitazone (P471000) impurity.
2. Pioglitazone

InChI:InChI=1/C15H16N2O3/c1-2-12-3-4-13(16-11-12)9-10-20-15-7-5-14(6-8-15)17(18)19/h3-8,11H,2,9-10H2,1H3

Upstream product

• 5223-06-3 5-ethyl-2-(2-hydroxyethyl)pyridine 
• 350-46-9 4-Fluoronitrobenzene 
• 824-78-2 4-nitrophenol sodium salt 
• 144809-27-8 toluene-4-sulfonic acid 2-(5-ethylpyridin-2-yl)ethyl ester 

Downstream Products

• 85583-40-0 4-[2-(5-ethylpyridin-2-yl)ethoxy]aniline 
• 105355-27-9 Pioglitazone 
• 112529-15-4 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride 
• 101931-09-3 methyl 3-{4-[2-acetoxy-2-(5-ethyl-2-pyridyl) ethoxy]phenyl}-2-bromopropionate 
• 145350-19-2 methyl 2-bromo-3-{4-[2-(5-ethyl-2-pyridyl)ethoxy]phenyl}propionate N-oxide 
• 101931-00-4 5-{4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione 
• 105355-26-8 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2-imino-4-thiazolidinone 
• 105355-25-7 methyl 2-bromo-3-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]phenyl}propionate 
• 669716-58-9 2-[2-(4-bromophenoxy)ethyl]-5-ethyl-pyridine 

Relevant academic research and scientific papers

Method for preparing 4-[2-(5-ethyl-2-pyridyl)ethyoxyl]nitrobenzene

The invention relates to a method for preparing 4-[2-(5-ethyl-2-pyridyl)ethyoxyl]nitrobenzene. The method is characterized by comprising the following steps: dissolving 2-(5-ethyl-2-pyridyl)ethyl alcohol in halohydrocarbon, adding inorganic alkali and a p

A PROCESS FOR THE PREPARATION OF 4-[2-(5-ETHYL-2-PYRIDYL)ETHOXY]NITROBENZENE AND PIOGLITAZONE

A process for the preparation of 4-[2-(5-ethyl-2-pyridyi)ethoxy]nitrobenzene is described, which comprises the step of reacting 2-(5-ethyl-2-pyridyl)ethanol with 1-fluoro-4-nitrobenzene in acetone in the presence of an alkali metal hydroxide. The intermediate 4-[2-(5-ethyl-2-pyridyI)ethoxy]nitrobenzene is used for the preparation of pioglitazone.

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.

AN IMPROVED PROCESS FOR THE PRODUCTION OF DERIVATIVES OF THIOZOLIDINEDIONES AND THEIR PRECURSORS

The invention provides a process for preparing derivatives of thiozolidinediones and their precursors comprising, (a) reacting a compound of general formula I wherein R1, R2 and R3 may be same or different and represent H, alkyl or alkoxy with C varying from 1 to 6, halogens, mono or di-substituted alkyl and aryl amines, and M represents hydrogen (H) or alkali metal selected from Na, K or Li with a compound of formula II, wherein R4 has the same meaning as R1 or R2 or R3 and X is halogen in presence or absence of solvent(s) under effective conditions to produce nitro ethers of general formula III, where in R1 to R4 has the same meaning as given above, provided when M is H and not its alkali metal salt, an alkali metal salt such as hydroxide or carbonate is required to be added while conducting the said reaction, (b) subjecting the said nitro ethers, with or without isolation, to Raney nickel-catalyzed reduction under conditions effective to produce corresponding nitro aniline ethers (c) coupling the said aniline ether with acrylates under Meerwein arylation conditions in presence of hydrobromic acid to produce α bromo substituted carboxylic acid derivatives followed by subjecting to solvent extractive purification (d) cyclising the purified derivative of α bromo substituted carboxylic acid as obtained in step (c) with thiourea to yield 2-imino -4-thiazolidinones then (e) hydrolyzing the said 2-imino-4-thiazolidinones to produce 2, 4-thiazolidinones and converting the same to its hydrochloride salts as white crystalline solids known to exhibit antidiabetic activity, by conventional methods.

Structural characterization of impurities in pioglitazone

In the pioglitazone bulk drug three prominent impurities I-III were detected up to concentrations of 0.1% (ranging from 0.05-0.1%) by reversed phase HPLC. These impurities were isolated from enriched mother liquor samples and characterized as 5-(4-hydroxybenzyl)-1,3-thiazolidine-2,4-dione (I) 5-(4-fluorobenzyl)-1,3-thiazolidine-2,4-dione (II), 2-[2-(4-bromophenoxy) ethyl-5-ethyl pyridine (III) based on their 1H, and 13C NMR, DEPT, Mass and IR spectral data. Structure elucidation and synthesis of these impurities is discussed.

PROCESS FOR THE PREPARATION OF 5-[[4-[2-(5-ETHYL-2-PYRIDINYL)ETHOXY]PHENYL] METHYL]-2,4-THIAZOLIDINEDIONE

A process for the preparation of 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione (formula 1) comprising a. reacting diazonium salt of 4-[2-(5-Ethyl-2-pyridyl) ethoxy] amino- benzene, compound of formula 2, with acrylamide, aqueous HX (wherein X is Br or Cl), under meerwein arylation conditions to yield compound of formula 3; b. condensing compound of formula 3 with thiourea to obtain compound of formula 4; and c. converting compound of formula 4 to compound of formula 1.

Ether and amide compounds and preparation of thereof as antidiadetics.

Ether and amide derivatives are disclosed, which are represented by the following formula (I) and its pharmaceutical acceptable salt, and which are useful for the treatment of diabetes. 1(with the provisos that (i) when A is —O—, then n is 2 or 3 (ii) when A is 2then n is 1 or 2. R3 is OH—, CH3SO2NH—, CF3SO2NH—, CH3SO2NHCH2—, CF3SO2NHCH2—, HOOC—, CH3OOC—, 3HOOC—CH2SO2NH—, CF3—CH2SO2NH—, 4R8—NHSO2—, R8—NHSO2—CH2—, HOOC—CH2—O—, HSO3N=CH—, or R9—SO2NHCO—; R4 is H, OH, O-alkyl or O—CH2OCH3; R5 is H, halogen atom, —CH2COOH or OH; R6 and R7 are hydrogen, t-butyl or pyrolidyl; R8 is hydrogen or lower alkyl; R9 is alkyl or thienyl; R10 is lower alkyl) or a pharmaceutically acceptable salt.

Studies on antidiabetic agents. Synthesis and hypoglycemic activity of 5-[4-(pyridylalkoxy)benzyl]-2,4-thiazolidinediones

The synthesis of a series of 5-[4-(pyridylalkoxy)benzyl]-2,4-thiazolidinediones is described. These compounds were evaluated for hypoglycemic and hypolipidemic activities in genetically obese and diabetic mice, yellow KK. 2-(2-Pyridyl)alkoxy derivatives were found to have much better hypoglycemic and hypolipidemic activities than 2-(3-pyridyl)- and 2-(4-pyridyl)alkoxy derivatives or even the previously reported compound, ciglitazone. The introduction of a hydroxyl group at the 2-position of the ethoxy chain potentiated the activities. Among the potent compounds, pioglitazone (AD-4833) was selected as a candidate compound.

Thiazolidinedione derivatives, useful as antidiabetic agents

Thiazolidinedione derivatives of the formula: STR1 and pharmacologically acceptable salts thereof are novel compounds, which exhibit in mammals blood sugar- and lipid-lowering activity, and are of value as a therapeutic agent for treatment of diabetes and hyperlipemia.