Oligosaccharide-containing 14-aminosteroid compounds and novel diastereoselective aminosteroid process chemistry

US5710259A · kind A · utility

Assignee

• The Procter & Gamble Company · US

Inventors

• Paul Michael Dybas · Port Crane, US
• Roland Norman Johnson · Cincinnati, US
• Randy Stuart Muth · Poolville, US
• Song Liu · San Jose, US

Key dates

• Filing date: Jun 2, 1995
• Grant date: Jan 20, 1998
• Expiry date: Jun 2, 2015

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07J41/0038
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention relates to oligosaccharide-containing 14-aminosteroid compounds and the pharmaceutically-acceptable acid salts or esters thereof of the general formula: ##STR1## wherein a) R.sub.1 is PA2 (i) COOR.sub.5, where PA3 R.sub.5 is hydrogen, a 1-6 carbon lower alkyl; a 1-6 carbon lower alkyl substituted by an amino group; an arylalkyl or heteroarylalkyl or a carbocyclic ring, or PA2 (ii) CHR.sub.6 OH, where PA3 R.sub.6 is a hydrogen atom or 1-6 carbon lower alkyl group, or PA2 (iii) COR'", where R'" is hydrogen; 1-6 carbon lower alkyl; 1-6 carbon lower alkyl substituted amino; amino or dialkylamino; and PA1 b) R.sub.2 is --NR.sub.7 R.sub.8, where PA2 R.sub.7 and R.sub.8, which may be the same or different, are hydrogen atoms or a 1-6 carbon lower alkyl; and PA1 c) R.sub.3 is an oligosaccharide sugar residue; and PA1 d) R.sub.4 is PA2 (i) OH, or PA2 (ii) H, or PA2 (iii) OR.sub.13, where PA3 R.sub.13 is a monosaccharide sugar residue; acetoxy; benzoxy; arylalkyl or heteroarylalkyl; and PA1 e) Z is PA2 (i) --CH--, where PA3 a and b are single bonds, or PA2 (ii) .dbd.C, where PA3 either a or b is a double bond. The present invention also relates to a process for introduc…