156334-89-3Relevant academic research and scientific papers
N-BENZYL-MORPHOLINE DERIVATIVES AS MODULATORS OF THE CHEMOKINE RECEPTOR
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Page/Page column 34, (2008/06/13)
The present invention provides a compound of a formula (I): wherein the variables are defined herein; to a process for preparing such a compound; and to the use of such a compound in the treatment of a chemokine (such as CCR3) mediated disease state.
ASYMMETRIC SYNTHESIS OF THE ENANTIOMERS OF 2-AMINOMETHYL-4-(4-FLUOROBENZYL)MORPHOLINE, AN INTERMEDIATE OF MOSAPRIDE, A GASTROPROKINETIC AGENT
Morie, Toshiya,Kato, Shiro,Harada, Hiroshi,Matsumoto, Jun-ichi
, p. 1033 - 1040 (2007/10/02)
An efficient asymmetric synthesis of the enantiomers of 2-aminomethyl-4-(4-fluorobenzyl)morpholine (3) which has served as an intermediate of mosapride (1), a potential gastroprokinetic agent, was achieved by the conversion of enantiomeric 3-chloro-1-(4-f
Synthesis and biological activities of the optical isomers of (±)-4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]me thyl]benzamide (Mosapride)
Morie,Kato,Harada,Yoshida,Matsumoto
, p. 877 - 882 (2007/10/02)
The enantiomers, (S)-(-)-1 and (R)-(+)-1, of (+)-4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]met hyl]benzamide (mosapride) [(+)-1], a new and selective gastroprokinetic agent, were prepared from optically active [4-(4-fluorobenzyl)-2-morpholinyl]methylamines (S)-(-)-4 and (R)-(+)-4, respectively. The requisite (S)-(-)-4 and (R)-(+)-4 were prepared by optical resolution of [4-(4-fluorobenzyl)-2-morpholinyl]methyl p-toluenesulfonate [(+)-5] using (-)- and (+)-N-(p-toluenesulfonyl)glutamic acids, followed by amination of the tosyloxy groupe of (R)-(-)-5 and (S)-(+)-5, respectively. The absolute configurations of (R)-(-)-5 and (S)-(+)-5 were determined on the basis of an asymmetric synthesis of (R)-(-)-5 from (S)-(+)-benzyl glycidyl ether [(S)-(+)-11]. Mosapride and its enantiomers, (S)-(-)-1 and (R)-(+)-1, were essentially equipotent in serotonin 5-HT4 receptor agonistic activity on the electrically evoked contractions in isolated guinea pig ileum.
