Process for the preparation of a nitric oxide donating prostaglandin analogue

The present invention relates to a process for preparing hexanoic acid, 6-(nitrooxy)-, (1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxo-2-hepten-1-yl]-3,5-dihydroxycyclopentyl]-1-(2-phenylethyl)-2-propen-1-yl ester of formula (I). In accordance with the present invention, the compound (I) can b...

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Bibliographische Detailangaben
Hauptverfasser:	COUSIN, JONATHAN, DIKER, KHALID, ALMIRANTE, NICOLETTA, RONSIN, GAEL, GORINS, GILLES, BRUNEAU, AUDREY
Format:	Patent
Sprache:	chi ; eng
Schlagworte:	ACYCLIC OR CARBOCYCLIC COMPOUNDS CHEMISTRY HUMAN NECESSITIES HYGIENE MEDICAL OR VETERINARY SCIENCE METALLURGY ORGANIC CHEMISTRY PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS
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Beschreibung
Zusammenfassung:	The present invention relates to a process for preparing hexanoic acid, 6-(nitrooxy)-, (1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxo-2-hepten-1-yl]-3,5-dihydroxycyclopentyl]-1-(2-phenylethyl)-2-propen-1-yl ester of formula (I). In accordance with the present invention, the compound (I) can be efficiently prepared with high purity by coupling bimatoprost in a boronate protected form with 6-(nitrooxy)hexanoyl chloride and removing the boronate protecting group. The invention also relates to a process for the preparation of 6-(nitrooxy) hexanoic acid having a HPLC purity equal to or greater than 99% and containing an amount of 6-{[6-(nitrooxy)hexanoyl]oxy}hexanoic acid (compound(IXa)) equal to or lower than 0.2%.