70028-85-2

Usage

InChI:InChI=1/C15H10F2N2O2/c16-11-5-1-9(2-6-11)15(13(20)18-14(21)19-15)10-3-7-12(17)8-4-10/h1-8H,(H2,18,19,20,21)

Upstream product

• 579-39-5 1,2-bis(4-fluorophenyl)ethane-1,2-dione 
• 57-13-6 urea 
• 120-89-8 parabanic acid 
• 462-06-6 fluorobenzene 
• 144461-86-9 2-(4-fluorophenyl)-2-(α-hydroxy-4-fluorobenzyl)-1,3-dithiane 

Downstream Products

• 895148-88-6 5,5-bis-(4-fluoro-phenyl)-3-((R)-1-methyl-pyrrolidin-3-yl)-imidazolidine-2,4-dione 
• 895149-07-2 1-(1-benzyl-piperidin-4-yl)-4,4-bis-(4-fluoro-phenyl)-imidazolidin-2-one 
• 895150-81-9 4,4-di-(4-fluorophenyl)-1-(piperidin-4-yl)-imidazolidin-2-one 
• 895149-18-5 4,4-bis-(4-fluoro-phenyl)-1-((R)-1-methyl-pyrrolidin-3-yl)-imidazolidin-2-one 
• 895148-79-5 3-(1-benzylpiperidin-4-yl)-5,5-di-(4-fluorophenyl)-imidazolidine-2,4-dione 

Relevant academic research and scientific papers

Discovery of diaryl imidazolidin-2-one derivatives, a novel class of muscarinic M3 selective antagonists (Part 1)

Pharmacophore-based structural identification, synthesis, and structure-activity relationships of a new class of muscarinic M3 receptor antagonists, the diaryl imidazolidin-2-one derivatives, are described. The versatility of the discovered scaffold allowed for several structural modifications that resulted in the discovery of two distinct classes of compounds, specifically a class of tertiary amine derivatives (potentially useful for the treatment of overactive bladder by oral administration) and a class of quaternary ammonium salt derivatives (potentially useful for the treatment of respiratory diseases by the inhalation route of administration). In this paper, we describe the synthesis and biological activity of tertiary amine derivatives. For these compounds, selectivity for the M3 receptor toward the M2 receptor was crucial, because the M2 receptor subtype is mainly responsible for adverse systemic side effects of currently marketed muscarinic antagonists. Compound 50 showed the highest selectivity versus M2 receptor, with binding affinity for M3 receptor Ki = 4.8 nM and for M2 receptor K i = 1141 nM. Functional in vitro studies on selected compounds confirmed the antagonist activity toward the M3 receptor and functional selectivity toward the M2 receptor.

AZOLE DERIVATIVES WITH ANTIMUSCARINIC ACTIVITY

The present invention relates to compounds of formula (I) wherein R1, R2, x, X, Y and B are as defined in the description for the treatment of muscarinic acetylcholine receptor mediated diseases, in particular M3 muscarinic receptor mediated diseases.

3-alkyl-(5,5'-diphenyl)imidazolidinediones as new cannabinoid receptor ligands

Twenty-four 3-alkyl-(5,5'-diphenyl)imidazolidinediones were synthesized and evaluated as new cannabinoid receptor ligands. Three compounds exhibited a Ki value around 100 nM against [3H]-SR 141716A binding obtained from human CB1 transfected CHO cells membranes. The lack of change of affinity in the presence of a non hydrolyzable GTP analogue seems to indicate they are cannabinoid antagonists.

Superacid Activated Condensation of Parabanic Acid and Derivatives with Arenes. A New Synthesis of Phenytoin and 5,5-Diarylhydantoins

A new synthetic route to phenytoin and 5,5-diarylhydantoins is repoted.Parabanic acid is converted to the 5,5-diarylhydantoins (65-98percent yield) from CF3SO3H and arenes.Deuterium substituted products are prepared in high yield from parabanic acid, CF3SO3D, and deuterated arenes.

A convenient preparation of symmetrical and unsymmetrical 1,2-diketones: Application to fluorinated phenytoin synthesis

1,2-Diketones are efficiently produced in two steps by reaction of aldehydes with anions derived from 2-substituted dithianes followed by treatment of the resulting alcoholis with NBS in aqueous acetone; phenytoin derivatives were prepared from these diketones by a standard method involving treatment with urea and potassium hydroxide under reflux.

Fluorinated phenytoin anticonvulsant analogs

Six ring-fluorinated phenytoin analogs were synthesized, and their anticonvulsant activity in the maximal electroshock seizure and subcutaneous pentylenetetrazol assays was determined. 5-(4-Fluorophenyl)-5-phenylhydantoin, 5-(3-fluorophenyl)-5-phenylhydan