Oligosaccharide-containing 14-aminosteroid compounds and novel diastereoselective aminosteroid process 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 (i) COOR.sub.5, where 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 (ii) CHR.sub.6 OH, where R.sub.6 is a hydrogen atom or 1-6 carbon lower alkyl group, or (iii) COR'", where R'" is hydrogen; 1-6 carbon lower alkyl; 1-6 carbon lower alkyl substituted amino; amino or dialkylamino; and b) R.sub.2 is --NR.sub.7 R.sub.8, where 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 c) R.sub.3 is an oligosaccharide sugar residue; and d) R.sub.4 is (i) OH, or (ii) H, or (iii) OR.sub.13, where R.sub.13 is a monosaccharide sugar residue; acetoxy; benzoxy; arylalkyl or heteroarylalkyl; and e) Z is (i) --CH--, where a and b are single bonds, or (ii) .dbd.C, where either a or b is a double bond. The present invention also relates to a process for introducing an amino group at the 14-position on a steroid nucleus wherein said amino group is diasteroselectively introduced onto the 14-position of the steroid nucleus via an iodoisocyanate addition comprising the steps of: a) adding the iodoisocyanate to the 14-15 position double bond on the steroid nucleus; and b) dehalogenation; and c) isocyanate conversion to the amine moiety on the 14-position of the steroid nucleus.

Dependencies are inferred from the claim text.