GEMCITABINE PRODUCTION PROCESS

Provided is a process for preparing gemcitabine or a salt thereof, which preferably includes selectively precipitating the β-anomer of a 3', 5'-di-O-protected-N-trimethylsilyl-2'-deoxy-2', 2'-difluorocytidine, removing the protecting groups to produce gemcitabine, and, optio...

Ausführliche Beschreibung

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Bibliographische Detailangaben
Hauptverfasser:	FIZITZKY TAMIR, ZELIKOVITCH LIOR, FRIEDMAN ODED, MANASCU JOSEF
Format:	Patent
Sprache:	eng
Schlagworte:	CHEMISTRY DERIVATIVES THEREOF HUMAN NECESSITIES HYGIENE MEDICAL OR VETERINARY SCIENCE METALLURGY NUCLEIC ACIDS NUCLEOSIDES NUCLEOTIDES ORGANIC CHEMISTRY PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS SUGARS
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Beschreibung
Zusammenfassung:	Provided is a process for preparing gemcitabine or a salt thereof, which preferably includes selectively precipitating the β-anomer of a 3', 5'-di-O-protected-N-trimethylsilyl-2'-deoxy-2', 2'-difluorocytidine, removing the protecting groups to produce gemcitabine, and, optionally, converting the gemcitabine into a salt. Preferably, the 3' and 5' protecting groups are the same or different, and at least one of the 3' and 5' protecting groups is cinnamoyl, naphthoyl, naphthylmethylcarbonyl, 2-methylbenzylcarbonyl, 4-methylbenzylcarbonyl or 9-fluorenylmethyloxycarbonyl. Also provided are methods for enriching the β-anomer from an anomeric mixture of a 3', 5'-di-O-protected-N-trimethylsilyl-2'-deoxy-2', 2'-difluorocytidine, e.g., a N-trimethylsilyl-2'-deoxy-2', 2'-difluoro-cytidine-3', 5'-diester, e.g., 3', 5'-dicinnamoyl-N-trimethylsilyl-2'-deoxy-2', 2'-difluorocytidine, using a slurrying process, and methods for converting the β-anomer-enriched product into gemcitabine or a salt thereof.