Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1994-10-07
1996-12-17
Ivy, C. Warren
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546220, 546221, A61K 31445, C07D21142
Patent
active
055853870
ABSTRACT:
Cisapride, i.e. cis-4-amino-5-chloro-N-[1-[3-(4 fluoro-phenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxy-benzamide, and similar benzamide derivatives, are prepared from novel 1-aryloxyalkyl- or 1-aralkyl-3-arylcarbonyloxy-4-oxo-piperidines, by nuclear substituent re arrangement involving acyl transfer under animal forming conditions, to give the corresponding 1-aryloxyalkyl- or 1-aralkyl-3-hydroxy-4-lower alkoxy-4-arylamido piperidine. This in turn is readily converted to the corresponding 3-oxo-4-arylamido-piperidine by reaction with strong organic acid, which can then be reduced, deprotected and 3-methylated to give the final compound, e.g. cisapride.
REFERENCES:
patent: 4745192 (1988-05-01), Ertl
G. Hofle, W. Steglich and H. Vorbruggen Angew, Chem. Int. Ed. Engl 569-583 (1978) "4-Dialkylaminopyridines as Highly Active Acylation Catalysts".
H. Hiemstra and W. Nico Speckamp, Tet. Lett. vol. 24, 1407-1410 (1983) "Completely Regioselective .alpha.-acyliminium Ion Cyclizations With Allyl and Propargyl Silanes".
C. A. Grob and C. Wagner, Hel. Chi. Acta, 1699-1707 (1955) "Die konkurrierende 1,2-und 1,3-acylwanderung".
G. Godor & J. Kiss, JACS vol. 72, 3495-3497 (1950) "Acyl Migration O-N in the Diasteromeric 2-aminocyclohexyl Benzoate".
J. H. Dodd, J. Guan and C. F. Schwender, Syn. Comm., vol. 23, 1003-1008 (1993) "A Mildl, Nonacidic Method for the Conversion of Carboxylic Esters into Oxazolines".
R. O. Hutchis, W-Y Su, R. Sivakamar, F. Cistone and Y. P. Stercho, J.O.C., vol. 48, 3412-3422 (1983) "Stereoselective Reductions of Substituted Cyclohexyl and Cyclopentyl . . . ".
H. C. Brown and S. Krishnamurthy, Tetrahedron, vol. 35, 567-607 (1979) "Tetrahedron Report Number 64" Forty Years of Hydride Reductions.
Czarkic, D. et al. Tetrahedron, 1985, 41(6), 1049-1056.
Grob, C. et al Hel. Chi, Acta 1955, 1699-707.
Lu Yee-Fung
Ngooi Teng-Ko
Oudenes Jan
Slemon Clarke
So Raymond
Dahlen Garth M.
Ivy C. Warren
Torcan Chemical Ltd.
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