163380-20-9

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Chemical Properties

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Uses

Protected Ezetimibe derivative.

Upstream product

• 204589-80-0 methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate 
• 204589-84-4 3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride 
• 204589-82-2 (3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone 
• 219653-96-0 (Z)-1-(4-(benzyloxy)phenyl)-N-(4-fluorophenyl)methaneimine 
• 75-36-5 acetyl chloride 
• 163222-33-1 ezetemibe 
• 108-24-7 acetic anhydride 
• 163222-32-0 (3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone 
• 190595-65-4 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one 

Downstream Products

• 190448-46-5 (1S)-1-(4-fluorophenyl)-3-[(2S,3R)-1-(4-fluorophenyl)-2-(4-hydroxyphenyl)-4-oxoazetidin-3-yl]propyl acetate 

Relevant academic research and scientific papers

An in vitro assay for evaluation of small-molecule inhibitors of cholesterol absorption

Giving cholesterol the brush off: An intestinal brush border membrane vesicle assay has been devised for the convenient in vitro testing of small molecules for inhibition of cholesterol absorption. The assay was used to identify new nonhydrolyzable glycosides as potent cholesterol-absorption inhibitors and an oxazolidinone as an effective replacement of the β-lactam scaffold of ezetimibe (1).

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.

Sugar-Substituted 2-Azetidinone Cholesterol Absorption Inhibitors: Enhanced Potency by Modification of the Sugar

A glucuronide conjugate of the potent 2-azetidinone cholesterol absorbtion inhibitor Sch 58235 was synthesized to confirm the structure of a metabolite isolated from in vivo sources.A series of 2-azetidinone glycosides was prepared via Schmidt trichloroim

HYDROXY-SUBSTITUTED AZETIDINONE COMPOUNDS USEFUL AS HYPOCHOLESTEROLEMIC AGENTS

Hydroxy-substituted azetidinone hypocholesterolemic agents of the formula or a pharmaceutically acceptable salt thereof, wherein: Ar1 and Ar2 are aryl or R4 -substituted aryl; Ar3 is aryl or R5-substituted aryl; X, Y and Z are -CH2 -, -CH(lower alkyl)- or

Combinations of hydroxy-substituted azetidinone compounds and HMG CoA Reductase Inhibitors

Hydroxy-substituted azetidinone hypocholesterolemic agents of the formula STR1 or a pharmaceutically acceptable salt thereof, wherein: Ar1 and Ar2 are aryl or R4 -substituted aryl; Ar3 is aryl or R5 -