204589-58-2

Usage

Uses

Used in Pharmaceutical Industry:
EzetiMibe Dehydoxy IMpurity is used as an active pharmaceutical ingredient (API) for the development of medications aimed at reducing cholesterol levels in patients with hyperlipidemia. Its application is crucial in the treatment of conditions associated with high cholesterol, such as atherosclerosis, coronary artery disease, and other cardiovascular diseases.
Used in Research and Development:
EzetiMibe Dehydoxy IMpurity serves as a valuable compound in the field of research and development, particularly in the study of cholesterol metabolism and the development of novel therapeutic strategies for managing hyperlipidemia and related health issues. Its use in research contributes to the advancement of medical knowledge and the discovery of new treatment options for patients.
Used in Quality Control and Regulatory Compliance:
EzetiMibe Dehydoxy IMpurity is utilized in the quality control processes of pharmaceutical manufacturing, ensuring the safety, efficacy, and purity of Ezetimibe-based medications. It is also essential in meeting regulatory requirements and guidelines for the approval and marketing of cholesterol-lowering drugs.

Upstream product

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• 204589-96-8 (3R,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-propyl]-azetidin-2-one 

Relevant academic research and scientific papers

Synthesis of 3-arylpropenyl, 3-arylpropynyl and 3-arylpropyl 2-azetidinones as cholesterol absorption inhibitors: Application of the palladium-catalyzed arylation of alkenes and alkynes

A series of 3-(3'-arylpropenyl)-2-azetidinones 8a-8k and 3-(3'-arylpropynyl)-2-azetidinones 16m-16p were prepared by the palladium-catalyzed arylation of 3-(3'-propenyl)-2-azetidinone 7, or by arylation of 4-pentenoic acid, or via ethyl 4-pentynoate followed by 2-azetidinone ring construction. The unsaturated 2-azetidinones were transformed to their saturated analogs 9a-9p by catalytic hydrogenation. Azetidinones 8a-8k, 9a-9p, and 16m-16p were evaluated for their biological activity as cholesterol absorption inhibitors in hamsters. (C) 2000 Elsevier Science Ltd.

First synthesis of N-(4-fluorophenyl)-5-(4-fluorophenyl)-2(4- hydroxybenzyl)pentanamide, a new potential cholesterol absorption inhibitor

The first synthesis of N-(4-fluorophenyl)-5-(4-fluorophenyl)-2-(4- hydroxybenzyl)pentanamide and a new synthesis of 1-(4-fluorophenyl)-3-[(4- fluorophenyl)propyl]-4-(4-hydroxyphenyl)-2-azetidinone starting from 4- fluorobenzaldehyde are described. This new amide could represent a potential new cholesterol absorption inhibitor.

Discovery of 1-(4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)- hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235): A designed, potent, orally active inhibitor of cholesterol absorption

(3R)-(3-Phenylpropyl)-1,(4S)-bis(4-methoxyphenyl)-2-azetidinone (2, SCH 48461), a novel inhibitor of intestinal cholesterol absorption, has recently been described by Burnett et al. and has been demonstrated to lower total plasma cholesterol in man. The potential sites of metabolism of 2 were considered, and the most probable metabolites were prepared. The oral cholesterol-lowering efficacy of the putative metabolites was evaluated in a 7-day cholesterol-fed hamster model for the reduction of serum total cholesterol and liver cholesteryl esters versus control. On the basis of our analysis of the putative metabolite structure-activity relationship (SAR), SCH 58235 (1, 1-4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]- (4S)-(4-hydroxyphenyl)-2-azetidinone) was designed to exploit activity enhancing oxidation and to block sites of potential detrimental metabolic oxidation. Additionally, a series of congeners of 2 were prepared incorporating strategically placed hydroxyl groups and fluorine atoms to further probe the SAR of 2-azetidinone cholesterol absorption inhibitors. Through the SAR analysis of a series of putative metabolites of 2, compound 1 was targeted and found to exhibit remarkable efficacy with an ED50 of 0.04 mg/kg/day for the reduction of liver cholesteryl esters in a 7-day cholesterol-fed hamster model.