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

Oligosaccharide-containing 14-aminosteroid compounds and the pharmaceutically-acceptable acid salts or esters thereof of the formula:

• ##STR40## 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;
• c) R.sub.3 is
• (i) an oligosaccharide sugar residue having the following structure:
• ##STR41## where R.sub.9 is hydrogen;
• methyl;
• hydroxy;
• carboxy;
• acetoxy;
• arylalkyloxy;
• heteroarylalkyloxy;
• or benzoxy;
• R.sub.10 is hydrogen;
• methyl;
• carboxy;
• acetoxy;
• arylalkyloxy;
• heteroarylalkyloxy;
• benzoxy or hydroxy;
• R.sub.11 is oxygen;
• wherein further when R.sub.11 is a substituent on the terminal monosaccharide sugar residue;
• R.sub.11 is OH;
• methyl;
• acetoxy;
• heteroarylalkyloxy;
• arylalkyloxy;
• and R.sub.12 is a hydrogen;
• methyl;
• methylhydroxymethyl or acetoxymethyl;
• or
• (ii) an oligosaccharide sugar residue having the following structure:
• ##STR42## where R.sub.14 and R.sub.15, which may be the same or different, are hydrogen;
• 1-6 carbon lower alkyl;
• heteroarylalkyl;
• arylalkyl;
• heteroaryl or aryl;
• R.sub.17 can be hydrogen;
• hydroxy;
• acetoxy or benzoxy;
• R.sub.18 and R.sub.19 are hydroxy;
• acetoxy and benzoxy;
• or
• (iii) an oligosaccharide residue having the following structure:
• ##STR43## where R.sub.14 and R.sub.15, which may be the same or different, are hydrogen;
• 1-6 carbon lower alkyl;
• heteroarylalkyl;
• arylalkyl;
• heteroaryl or aryl;
• R.sub.14a is oxygen;
• wherein further when R.sub.14a is a substituent on the terminal monosaccharide sugar residue;
• R.sub.14a must be hydroxy;
• methyl;
• acetoxy;
• arylalkyloxy or heteroarylalkyloxy;
• 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.