172648-06-5

Basic information

• Product Name: Acetic acid, [4-[(2,4-dioxo-5-thiazolidinyl)methyl]phenoxy]-, ethyl ester
• Synonyms: Acetic acid, [4-[(2,4-dioxo-5-thiazolidinyl)methyl]phenoxy]-, ethyl ester;Acetic acid, [4-[(2,4-dioxo-5-thiazolidinyl)methyl]phenoxy]-, ethyl ester (9CI);2-[4-[(2,4-dioxo-5-thiazolidinyl)methyl]phenoxy]Acetic acid ethyl ester
• CAS NO: 172648-06-5
• Molecular Formula: C₁₄H₁₅NO₅S
• Molecular Weight: 309.34
• Product Categories: Drug Intermediates
• Mol File: 172648-06-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Acetic acid, [4-[(2,4-dioxo-5-thiazolidinyl)methyl]phenoxy]-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, [4-[(2,4-dioxo-5-thiazolidinyl)methyl]phenoxy]-, ethyl ester(172648-06-5)
• EPA Substance Registry System: Acetic acid, [4-[(2,4-dioxo-5-thiazolidinyl)methyl]phenoxy]-, ethyl ester(172648-06-5)

Safety Data

• Hazardous Substances Data: 172648-06-5(Hazardous Substances Data)

Upstream product

• 172648-05-4 methyl 4-(2-bromo-2-n-butoxycarbonylethyl)phenoxyacetate 
• 199113-88-7 5-[4-[[3-methyl-4-oxo-3,4-dihydro-2-quinazolinyl]methoxy]phenyl methylene]thiazolidine-2,4,-dione 
• 59954-04-0 methyl 4-aminophenoxyacetate 
• 19786-48-2 methyl 2-(4-nitrophenoxy)acetate 
• 100-02-7 4-nitro-phenol 

Downstream Products

• 179087-93-5 [4-[[2,4-dioxo-1,3-thiazolidine-5-yl]methyl]phenoxy]acetic acid 

Relevant articles and documents

Process for the preparation of thiazolidine-2,4-dione derivatives

An improved process for the preparation of 5-[4-[[3-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl]methoxy]benzyl]thiazolidine-2,4-dione of formula (1) which comprises: reducing the compound of formula (2′) where R represents a (C1-C4)alkyl

Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases

The present invention relates to novel antidiabetic compounds, their tautomeric forms, their derivatives, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically accep

Molecular design, synthesis, and hypoglycemic activity of a series of thiazolidine-2,4-diones

A series of imidazopyridine thiazolidine-2,4-diones were designed and synthesized from their corresponding pyridines. These compounds represent conformationally restricted analogues of the novel hypoglycemic compound rosiglitazone (5). The series was evaluated for its effect on insulin-induced 3T3-L1 adipocyte differentiation in vitro and its hypoglycemic activity in the genetically diabetic KK mouse in vivo. The structure-activity relationships are discussed. On the basis of the in vivo potency, 5-[4-(5-methoxy-3-methyl-3H-imidazo[4,5-b]pyridin-2-ylmethoxy)ben zyl]thiazolidine-2,4-dione (19a) was selected as the candidate for further studies in a clinical setting.

Benzimidazole derivatives, their preparation and their therapeutic use

Compounds of formula (I): STR1 [wherein: X represents an optionally substituted benzimidazole group; Y represents an oxygen or sulfur atom; Z represents a 2,4-dioxothiazolidin-5-ylidenylmethyl, 2,4-dioxothiazolidin-5-ylmethyl, 2,4-dioxooxazolidin-5-ylmethyl, 3,5-dioxooxadiazolidin-2-ylmethyl or N-hydroxyureidomethlyl group; R represents hydrogen, alkyl, alkoxy, halogen, hydroxy, nitro, amino or aralkyl; and m is an integer from 1 to 5]; have valuable activity for the treatment and/or prophylaxis of a variety of disorders, including one or more of: hyperlipemia, hyperglycemia, obesity, impaired glucose tolerance (IGT), insulin resistance and diabetic complications.

Treatment of arteriosclerosis and xanthoma

A combination of one or more HMG-CoA reductase inhibitors (for example pravastatin, lovastatin, simvastatin, fluvastatin, rivastatin or atorvastatin) with one or more insulin sensitizers (for example troglitazone, pioglitazone, englitazone, BRL-49653, 5-(4-{2-?1-(4-2'-pyridylphenyl)ethylideneaminooxy!-ethoxy}benzyl)thiazolidine-2,4-dione, 5-{4-(5-methoxy-3-methylimidazo?5,4-b!pyridin-2-yl-methoxy)benzyl}thiazolidine-2,4-dione or its hydrochloride, 5-?4-(6-methoxy-l-methylbenzimidazol-2-ylmethoxy)benzyl!thiazolidine-2,4-dione, 5-?4-(l-methylbenzimidazol-2-ylmethoxy)benzyl!-thiazolidine-2,4-dione and 5-?4-(5-hydroxy-1,4,6,7-tetramethylbenzimidazol-2-ylmethoxy) benzyllthiazolidine-2,4-dione) exhibits a synergistic effect and is significantly better at preventing and/or treating arteriosclerosis and/or xanthoma than is either of the components of the combination alone.

Heterocyclic compounds having anti-diabetic activity and their use

Compounds of formula (I): STR1 [wherein: X represents an unsubstituted or substituted indolyl, indolinyl, azaindolyl, azaindolinyl, imidazopyridyl or imidazopyrimidinyl group; Y represents an oxygen or sulfur atom; Z represents a 2,4-dioxothiazolidin-5-ylidenylmethyl, 2,4-dioxothiazolidin-5-ylmethyl, 2,4-dioxooxazolidin-5-ylmethyl, 3,5-dioxooxadiazolidin-2-ylmethyl or N-hydroxyureidomethyl group; R represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a hydroxy group, a nitro group, an aralkyl group or a unsubstituted or substituted amino group; and m is an integer of from 1 to 5] have hypoglycemic and anti-diabetic activities.

Benzimidazole derivatives, their preparation and their therapeutic use

Compounds of formula (I): [in which: X represents an optionally substituted benzimidazole group; Y represents an oxygen or sulphur atom; Z represents a 2,4-dioxothiazolidin-5-ylidenylmethyl, 2,4-dioxothiazolidin-5-ylmethyl, 2,4-dioxo-oxazolidin-5-ylmethyl, 3,5-dioxooxadiazolidin-2-ylmethyl or N-hydroxyureidomethyl group; R represents hydrogen, alkyl, alkoxy, halogen, hydroxy, nitro, amino or aralkyl; and mis an integer from 1 to 5]; have valuable activity for the treatment and/or prophylaxis of a variety of disorders, including one or more of: hyperlipemia, hyperglycemia, obesity, impaired glucose tolerance (IGT), insulin resistance and diabetic complications.