Diastereomers of 1-(isopropoxycarbonyloxy)ethyl 3-cephem-4-carboxylate

US5461043A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Gerd Fischer · Limburg, DE
• Elisabeth Defossa · Idstein, DE
• Uwe Gerlach · Hattersheim, DE
• Rolf Horlein · Frankfurt am Main, DE
• Norbert Krass · Frankfurt am Main, DE
• Rudolf Lattrell · Königstein, DE
• Ulrich Stache
• Theodor Wollmann · Hofheim, DE
• Dieter Isert · Eschborn, DE

Key dates

• Filing date: Sep 3, 1992
• Grant date: Oct 24, 1995
• Expiry date: Sep 3, 2012

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P31/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Enterally absorbable diastereomers of 1-(isopropoxycarbonyloxy)ethyl (6R,7R)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino)acetamido]-3-(metho xymethyl)-3-cephem-4-carboxylate of the formula I ##STR1## and their physiologically acceptable salts and also diastereomerically pure salts of the compounds of the formula II ##STR2## where HX is a mono- or polybasic acid and where X is an inorganic or organic physiologically acceptable anion, and a process for the preparation of these compounds of the formula I or II, which comprises first precipitating the more sparingly soluble diastereomer of the formula IV in the mixing together of 1 equivalent of a solution of the diastereomer mixture of the formula III with 0.2-2 equivalents of a solution of the acid component HY and separating it off by filtration, then precipitating the more readily soluble diastereomer of the formula IV from the filtration solution, it being possible for the acid component HY to be identical or different in the consecutive partial steps and any desired sequence of addition of different acid components HY being possible, and optionally further purifying the obtained salts by crystallization, are described.