177948-39-9

Upstream product

• 56613-80-0 D-2-phenylglycinol 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 122-98-5 2-Anilinoethanol 

Downstream Products

• 1500113-89-2 (R)-tert-butyl 4-(3-(2,4-difluoro-5-(methoxycarbonyl)phenyl)-1-(2-hydroxy-1-phenylethyl)ureido)piperidine-1-carboxylate 
• 1500113-92-7 (R)-5-(3-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-oxo-4-phenylimidazolidin-1-yl)-2,4-difluorobenzoic acid 
• 1500113-90-5 (R)-tert-butyl 4-(3-(2,4-difluoro-5-(methoxycarbonyl)phenyl)-2-oxo-5-phenylimidazolidin-1-yl)piperidine-1-carboxylate 
• 1500113-91-6 (R,Z)-tert-butyl 4-(2-((2,4-difluoro-5-(methoxycarbonyl)phenyl)imino)-4-phenyloxazolidin-3-yl)piperidine-1-carboxylate 
• 926292-68-4 4-((R)-4-phenyl-2-thioxooxazolidin-3-yl)-piperidine-1-carboxylic acid tert-butyl ester 
• 177947-39-6 1-[3-(5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl)propyl]-4-[(R)-α-(hydroxymethyl)benzylamino]piperidine 
• 177948-38-8 (R)-2-phenyl-2-(piperidin-4-ylamino)ethanol 

Relevant academic research and scientific papers

Alkali carbonate effects on N-(2-hydroxyethyl)urea cyclization: Application to a 2-imidazolidinone scale-up

An imidazolidinone intermediate (3) used in the synthesis of novel HIV-entry inhibitors was prepared on multihundred gram scales in four steps and 40% overall yield. The penultimate step in the synthesis involved regioselective N-cyclization of N-(2-hydroxylethyl)urea (11) by in situ activation of the terminal hydroxyl group with p-TsCl in the presence of base. The ratio of N-cyclized to O-cyclized products followed a group IA periodic trend relative to the alkali carbonate base employed. The use of Cs2CO3 as base effected the desired N-cyclization with a high degree of regiocontrol (>98%).

CHEMOKINE RECEPTOR BINDING COMPOUNDS

The present invention relates to chemokine receptor binding compounds, pharmaceutical compositions and their use. More specifically, the present invention relates to modulators of chemokine receptor activity, preferably modulators of CCR4 or CCR5. In one aspect, these compounds demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

Azetidine, pyrrolidine and piperidine derivatives as 5HT1 receptor agonists

PCT No. PCT/GB95/02759 Sec. 371 Date Jul. 28, 1997 Sec. 102(e) Date Jul. 28, 1997 PCT Filed Nov. 27, 1995 PCT Pub. No. WO96/17842 PCT Pub. Date Jun. 13, 1996A class of substituted azetidine, pyrrolidine and piperidine derivatives are selective agonists of 5-HT1-like receptors, being potent agonists of the human 5-HT1D alpha receptor subtype whilst possessing at least a 10-fold selective affinity for the 5-HT1D alpha receptor subtype relative to the 5-HT1D beta subtype; they are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT1D receptors is indicated, whilst eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT1D receptor agonists.

3-[3-(piperidin-1-yl)propyl]indoles as highly selective h5-HT(1D) receptor agonists

Several 5-HT(ID/1B) receptor agonists are now entering the marketplace as treatments for migraine. This paper describes the development of selective h5-HT(1D)receptor agonists as potential antimigraine agents which may produce fewer side effects. A series of 3-[3-(piperidin-1-yl)propyl]indoles has been synthesized which has led to the identification of 80 (L-772,405), a high- affinity h5-HT(1D) receptor full agonist having 170-fold selectivity for h5- HT(1D) receptors over h5-HT(1B) receptors. L-772,405 also shows very good selectivity over a range of other serotonin and nonserotonin receptors and has excellent bioavailability following subcutaneous administration in rats. It therefore constitutes a valuable tool to delineate the role of h5-HT(1D) receptors in migraine. Molecular modeling and physical properties have been utilized to postulate the binding conformation of these compounds in the receptor cavity.

Azetidine, pyrrolidine and piperidine derivatives

A class of substituted azetidine, pyrrolidine and piperidine derivatives are selective agonists of 5-HT1 -like receptors, being potent agonists of the human 5-HT1Dα receptor subtype whilst possessing at least a 10-fold selective affinity for the 5-HT1Dα receptor subtype relative to the 5-HT1Dβ subtype; they are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT1D receptors is indicated, whilst eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT1D receptor agonists.