Semisynthetic diastereomerically pure N-glycidylanthracyclines, a process for the stereoselective preparation thereof as the use thereof as cytostatics

US5602108A · kind A · utility

Assignee

• Behringwerke Aktiengesellschaft · DE

Inventors

• Manfred Gerken · Marburg, DE
• Monika Grimm · Biebertal, DE
• Ernst Raab · Lahntal, DE
• Dieter Hoffmann · Marburg, DE
• Reiner Straub · Marburg, DE

Key dates

• Filing date: Jun 5, 1995
• Grant date: Feb 11, 1997
• Expiry date: Jun 5, 2015

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07H15/252
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Semisynthetic diastereomerically pure N-glycidylanthracyclines, a process for the stereoselective preparation thereof and the use thereof as cytostatics. The invention relates to anthracyclines having cytostatic activity and the formula I, which are, where appropriate, in the form of a salt with an inorganic or organic acid, ##STR1## in which R.sup.1 is hydrogen or a hydroxyl group, PA1 R.sup.2 is hydrogen, a hydroxyl group or an alkyloxy group (C.sub.1 -C.sub.4), PA1 R.sup.3 is hydrogen, a hydroxyl group or a structure of the formula II ##STR2## R.sup.4 is CH.sub.2 CH.sub.3, COCH.sub.3, COCH.sub.2 OH, CHOHCH.sub.3 or CHOHCH.sub.2 OH, PA1 R.sup.5 is hydrogen, a hydroxyl group, a methoxycarbonyl group or a structure of the formula II, PA1 R.sup.6 is hydrogen, an alkyl group (C.sub.1 -C.sub.4), an allyl group, a benzyl group or mono- or di-methyloxy-substituted benzyl group, a tetrahydropyranyl group, PA1 R.sup.7 is hydrogen, an alkyl group (C.sub.1 -C.sub.4), an allyl group, a benzyl group or mono- or di-methyloxy-substituted benzyl group and PA1 R.sup.8 is a structure of the formula III or IV ##STR3## and to a process for the preparation of these compounds, which comprises reacting…