193204-22-7Relevant academic research and scientific papers
Chromatography-free stereoselective synthesis of (R)-3-benzylpiperidine
Sivák, Ivan,Berke?, Du?an,Ko?í?ek, Jozef,Kolarovi?, Andrej
supporting information, p. 1079 - 1082 (2018/03/26)
The present study describes aza-Michael addition reactions of 4-aroylpent-4-enoic acids with (R)-phenylglycinol. Subsequent spontaneous lactamization yielded the corresponding piperidin-2-ones, which can selectively crystallize in very high diastereomeric purity. These are useful intermediates in the stereoselective syntheses of diverse 3-benzylpiperidines, as herein demonstrated by a chromatography-free and straightforward Gram-scale synthesis of (R)-3-benzylpiperidine hydrochloride.
Discovery of N-propylurea 3-benzylpiperidines as selective CC chemokine receptor-3 (CCR3) antagonists
Varnes, Jeffrey G.,Gardner, Daniel S.,Santella III, Joseph B.,Duncia, John V.,Estrella, Melissa,Watson, Paul S.,Clark, Cheryl M.,Ko, Soo S.,Welch, Patricia,Covington, Maryanne,Stowell, Nicole,Wadman, Eric,Davies, Paul,Solomon, Kimberley,Newton, Robert C.,Trainor, George L.,Decicco, Carl P.,Wacker, Dean A.
, p. 1645 - 1649 (2007/10/03)
The discovery of novel and selective small molecule antagonists of the CC Chemokine Receptor-3 (CCR3) is presented. Simple conversion from a 4- to 3-benzylpiperidine gave improved selectivity for CCR3 over the serotonin 5HT2A receptor. Chiral resolution and exploration of mono- and disubstitution of the N-propylurea resulted in several 3-benzylpiperidine N-propylureas with CCR3 binding IC50s under 5 nM. Data from in vitro calcium mobilization and chemotaxis assays for these compounds ranged from high picomolar to low nanomolar EC50s and correlated well with antagonist binding IC50s.
N-ureidoalkyl-piperidines as modulators of chemokine receptor activity
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, (2008/06/13)
The present application describes modulators of CCR3 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.
N-ureidoalkyl-piperidines as modulators of chemokine receptor activity
-
, (2008/06/13)
The present application describes modulators of CCR3 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.
N-ureidoalkyl-piperidines as modulators of chemokine receptor activity
-
, (2008/06/13)
The present application describes modulators of CCR3 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.
