Amphiphilic compounds derived from amino acids or peptides, their methods of synthesis and their application as drug delivery systems

An amphiphilic compound derived from an amino acid or a peptide and having the formula:

• ##STR35## wherein a. X is a polyhydroxylated hydrophilic moiety selected from the group consisting of a sugar, a polyol, an aminopolyol or an oligosaccharide;
• b. R.sup.1 represents a bivalent radical derived from a monosaccharide in an open form and having the formula:
• ##STR36## c. AA is an amino acid or peptide moiety;
• d. Y.sup.1 is --NH--, --S--, --CO--, --C(O)--(CH.sub.2).sub.L --, wherein L is 1 or 2, or --O--;
• e. R.sup.2 and R.sup.3, which can be identical or different, are H;
• a linear or branched, saturated or unsaturated C.sub.5-20 hydrocarbon;
• or a linear or branched, saturated or unsaturated C.sub.5-20 fluorinated hydrocarbon or fluorocarbon radical wherein 50 to 100% of the hydrogen atoms have been replaced by fluorine atoms, said hydrocarbon, fluorinated hydrocarbon or fluorocarbon radical optionally having one or more O and S atoms within the C chain, and optionally having the hydrogen atoms of said radical replaced by one or more chlorine or bromine atoms;
• and
• an unsaturated terminal group having the formula:
• CH.dbd.CH.sub.2
• --O--CH.dbd.CH.sub.2 ;
• --OC(O)CR.sub.5 .dbd.CH.sub.2 ;
• --C(O)--CR.sub.5 .dbd.CH.sub.2 ;
• or
• --NHC(O)CR.sub.5 .dbd.CH.sub.2
• in which R.sup.5 is H or CH.sub.3, provided that R.sup.2 and R.sup.3 do not both represent H;
• f. R.sup.4 represents
• --CO(CH.sub.2).sub.m -- with O.ltoreq.m.ltoreq.2;
• --NH(CH.sub.2).sub.n -- with O.ltoreq.n.ltoreq.4;
• --O--CH.sub.2-- ;
• ##STR37## wherein AA is an amino acid or peptide;
• g. Y.sup.2 and Y.sup.3, which are different, are
• --(CH.sub.2).sub.m C(O)--NH-- with O.ltoreq.m.ltoreq.2;
• --(CH.sub.2).sub.m C(S)--NH-- with O.ltoreq.m.ltoreq.2;
• --(CH.sub.2).sub.p OC(O);
• --(CH.sub.2)2.sub.p OC(O)-- with O.ltoreq.p.ltoreq.2;
• --(CH.sub.2)S--;
• --C(O)O--;
• --C(O)S--;
• --(CH.sub.2).sub.n NHC(O)-- with O.ltoreq.n.ltoreq.4;
• --(CH.sub.2).sub.2 --CH(OH)--CH.sub.2 --NH--C(O)--;
• ##STR38## provided that at least one of the Y.sup.2 and Y.sup.3 represent --NH--C(O)-- or --C(O)--NH--.