(+)-Norcisapride
OwnerJozef Jan Pieter Heykants, Antonius Adrianus Hendrikus Petrus Megens +3inventors
InventorsJozef Jan Pieter Heykants, Antonius Adrianus Hendrikus Petrus Megens, Willem Emiel Gustaaf Meuldermans, Joannes Adrianus Jacobus Schuurkes, Jean-Paul Rene Marie Andre Bosmans
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Abstract
The present invention concerns (+)-norcisapride, and its pharmaceutically acceptable acid additions salts, a process for preparing said compound, and its use for the manufacture of a medicament for treating gastro-intestinal disorders while avoiding central nervous system effects. Also provided are method of treating gastro-intestinal disorders.
Claims32
A process for preparing (+)-norcisapride base of formula
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- characterized by
- a) separating the enantiomers of cis-ethyl 4-(4-amino-5-chloro-2-methoxy-benzoylamino)-3-methoxy-1-piperidine carboxylate by liquid chromatography over a chiral stationary phase, and
- b) isolating the fraction having a specific rotation [α]D20 in methanol that is dextrorotatory, and
- c) solvolysing said fraction to (+)-norcisapride.
(+)-Norcisapride having a specific rotation [α]D20 in methanol that is dextrorotatory
(+)-Norcisapride having a specific optical rotation [α]D20 of about +5.60° (c=1% w/v in methanol).
(+)-Norcisapride having the absolute configuration of (3S,4R)
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- (3S,4R)-cis-4-amino-5-chloro-2-methoxy-N-(3-methoxy-4-piperidinyl)benzamide.
Compounds of formula (V) wherein the piperidine ring has the absolute configuration (3S,4R) and PG is methyloxycarbonyl, ethyloxycarbonyl, tert-butyloxycarbonyl or phenylmethyl.
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Dependencies are inferred from the claim text.