Glycosylated steroid derivatives for transport across biological membranes and process for making and using same

A compound having the formula (III):

• ##STR45## wherein A is H, O, OH, OR.sup.6, NR.sup.7 R.sup.8, N.sub.3, NHCOR.sup.7, OCOAr, O--CO--OR.sup.9, O--CO--R.sup.9, NCH.sub.2 C.sub.6 H.sub.5, and in which Ar is phenyl or phenyl substituted with 1-3 groups selected from the group consisting of halogen, C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.3 alkoxy;
• "a" is a single bond in the alpha or beta configuration with the proviso that when A.dbd.O, "a" is a double bond;
• R.sup.3 is H, OH or OR.sup.6 ;
• R.sup.4 is H, OH or OR.sup.6 ;
• R.sup.5 is CO.sub.2 R.sup.10, CH.sub.2 OR.sup.9, CONH.sub.2, CONHR.sup.7, CONR.sup.7 R.sup.8, CO--S--R.sup.10, CH.sub.2 S(O).sub.p --S--R.sup.10, CH.sub.2 NH.sub.2, CH.sub.2 NHR.sup.7, CH.sub.2 NR.sup.7 R.sup.8, CH.sub.2 --S(O).sub.p --S--R.sup.10 ;
• R.sup.6 is glycosyl moiety comprising 1-10 monosaccharide units in which the glycosidic linkage at the anomeric carbon atom of each monosaccharide unit is independently alpha or beta;
• R.sup.7 and R.sup.8, independently are H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.10 alkylcycloalkyl, phenyl, benzyl, or, taken together are (CH.sub.2).sub.f, where f=3-6;
• R.sup.9 is H or C.sub.1 -C.sub.3 alkyl;
• R.sup.10 is H, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkenyl, C.sub.1 -C.sub.10 alkynyl, C.sub.6 H.sub.5 or CH.sub.2 C.sub.6 H.sub.5 ;
• p is 0, 1 or 2;
• n is 0, 1 or 2;
• u is 0, 1, 2, 3, 4 or 5;
• v is 0, 1, 2, 3, 4 or 5, so long as u and v are not both 0;
• Oligo represents an oligonucleotide covalently attached to the group A or R.sup.5 either directly or via a linker group;
• or a salt thereof.