76713-26-3

Upstream product

• 50541-93-0 4-amino-1-benzylpiperidine 
• 4461-33-0 benzoyl isocyanate 

Downstream Products

• 164393-22-0 1-[1-(3-cyanobenzyl)piperidin-4-yl]-5-methyl-4-phenyl-1,3-dihydroimidazol-2-one 
• 164393-09-3 1-(1-benzylpiperidin-4-yl)-5-methyl-4-phenyl-1,3-dihydroimidazol-2-one 
• 164393-32-2 1,3-dihydro-5-methyl-4-phenyl-1-(4-piperidinyl)-2H-imidazol-2-one 
• 61220-35-7 4-<(aminocarbonyl)amino>-1-benzylpiperidine 

Relevant academic research and scientific papers

1-(3-Cyanobenzylpiperidin-4-yl)-5-methyl-4-phenyl-1,3-dihydroimidazol- 2-one: A selective high-affinity antagonist for the human dopamine D4 receptor with excellent selectivity over ion channels

After the requirement of pseudocycle formation in the ureas 3 and 7 for hD4 binding and selectivity was confirmed, structural hybridization with the known hD4 ligand 2 led to the design and identification of the lead 4-(2- oxo-1,3-dihydroimidazol-2-yl)piperidine 8. Optimization studies were carried out on 8 with the aim of achieving 1000-fold selectivity for hD4 over all other receptors while retaining the good pharmacokinetic properties of the lead. After initial preparation of 8 as a minor component in a low-yielding reaction, a novel and regioselective 'four-step/one-pot' procedure was developed which proved to be applicable to rapid investigation of the SAR of the 1,3-dihydroimidazol-2-one ring. Various changes to substituents attached to the 3-, 4-, or 5-position of the 1,3-dihydroimidazol-2-one core of 8 did not significantly improve selectivity for hD4 over hD2 and hD3. Greater selectivity (> 1000-fold) was ultimately achieved by meta substitution of the benzyl group of 8 with various substituents. Compounds 28, 31, and 32 all possess the required selectivity for hD4 over the other dopamine subtypes, but only 32 has > 1000-fold selectivity over all the key counterscreens we tested against. Compound 32 is an antagonist at hD4 and has a good pharmacokinetic profile in the rat, with excellent estimated in vivo receptor occupancy, thus making it a potentially useful pharmacological tool to investigate the role of the D4 receptor.

IMIDAZOLONE AND OXAZOLONE DERIVATIVES AS DOPAMINE ANTAGONISTS

A class of imidazolone and oxazolone derivatives of Structure I, STR1 wherein X represents oxygen or N--R 1 ; Q represents a substituted five-, six-or seven-membered monocyclic heteroaliphatic ring which contains one nitrogen atom as the sole hetero