204589-68-4

Usage

Uses

Used in Pharmaceutical Industry:
Ezetimibe Related Impurity 7 is used as a reference standard for the quality control and assurance of Ezetimibe, an antihyperlipoproteinemic drug. It helps in the identification, quantification, and assessment of the purity of Ezetimibe in the manufacturing process, ensuring the drug's safety and efficacy.
Used in Research and Development:
Ezetimibe Related Impurity 7 serves as an essential compound in the research and development of new drugs and therapies related to cholesterol absorption inhibition. It aids in understanding the metabolic pathways and potential side effects of Ezetimibe, contributing to the development of safer and more effective treatments for hyperlipidemia.
Used in Regulatory Compliance:
Ezetimibe Related Impurity 7 is utilized in the regulatory compliance process to ensure that the manufacturing and distribution of Ezetimibe meet the required standards and guidelines. It helps in the evaluation of the drug's quality, safety, and efficacy, ensuring that it adheres to the regulatory requirements set by various health authorities.

Upstream product

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• 204589-82-2 (3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone 
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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.

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.