Glycomimetics as selectin antagonists and pharmaceuticals having antiinflammatory activity prepared therefrom

US6197752A · kind A · utility

Assignee

• GLYCOREX AB · SE

Inventors

• Wolfgang Schmidt · Frankfurt, DE
• Ulrich Sprengard · Gustavsburg, DE
• Gerhard Kretzschmar · Eschborn, DE
• Horst Kunz · Mainz, DE

Key dates

• Filing date: Sep 5, 1996
• Grant date: Mar 6, 2001
• Expiry date: Sep 5, 2016

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D307/20
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The invention relates to novel mimetics of the tetrasaccharides sialyl- Lewis-X (SLeX) and sialyl- Lewis-A (SLeA) having an improved action as inhibitors of cell adhesion, specifically a compound of the formula I ##STR1## in which PA1 R.sup.1 is --H, --CH.sub.3 or --CH.sub.2 OH, PA1 R.sup.2 is --H or --OH, PA1 R.sup.3, R.sup.4 and R.sup.5 independently of one another are --H, C.sub.1 -C.sub.4 -alkyl or --OH, PA1 R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 independently of one another are --H or C.sub.1 -C.sub.4 -alkyl PA1 D is --O--C(O)--, --C(O)--or --NR.sup.6 --C(O)--, PA1 E is --CR.sup.7 R.sup.8 --, --NR.sup.7 --, or a nitrogen heterocycle of the formula ##STR2## PA1 n is 1 or 2, PA1 m is 0 or 1, PA1 p is an integer from 0 to 10, PA1 q is 1 or 2 and PA1 X.sup.1 and X.sup.2 independently of one another are --H, --COOR.sup.9, --NR.sup.9 R.sup.10, --OH, --OSO.sub.3 H, --CH.sub.2 COOR.sup.9 or --CH.sub.2 OSO.sub.3 H or together are .dbd.O, to a process for preparing these compounds and to their use as pharmacological active compounds and diagnostic agents.