Muramyl peptide derivatives and pharmaceutical compositions

Claim 1

A compound which is an immunological adjuvant and effective against Klebsiella, which compound has the formula: ##STR18## in which the substituents R, R 1 , R 2 , R 4 , R 6 , X, Y and Z has the following definition: R is hydrogen or an alkyl group having 1 to 4 carbon atoms, R 1 is hydrogen hydroxyl or phenylamino, R 2 is hydrogen or methyl, R 4 is hydrogen or acyl group having 1 to 4 carbon atoms, R 6 is hydrogen, saturated or unsaturated acyl having from 1 to about 4 carbon atoms, mycolyl group having 80 to 90 carbon atoms or corynomycoyl, X is L-alanyl, L-seryl, L-valyl, or glycyl, Y is -OH, an alkoxy radical having from 1 to 10 carbon atoms, or -NH 2 , the hydrogens of the amino group being optionally substituted by alkyl residues having 1 to 10 carbon atoms, or an aminoacyl residue, A is an aminoacyl residue selected from the group consisting of L-alanyl, L-arginyl, L-asparagyl, L-aspartyl, L-cystenyl, L-glutaminyl, L-glutamyl, glycyl, L-histidyl, L-hydroxyprolyl, L-isoleucyl, L-leucyl, L-lysyl, L-methionyl, L-orinthyl, L-phenylalanyl, L-prolyl, L-seryl, L-threonyl, L-tryptophanyl, L-tyrosyl and L-valyl or an aminoalcohol residue (-NH-CH-CH 2 -O-) corresponding to these aminoacyls (-NH-CH-CO-), wherein when the A groups are present in the same compound they may be identical or different, n is zero or 1, Z is selected from the group consisting of -OR', -NHR', -OCH 2 -CH 2 O-COR' or -OCH 2 -CHOH-CH 2 O-R°, wherein R° is a mycolic acid group having from 80 to 90 carbon atoms, or corynomycoyl and R' is a linear or branched alkyl group having 4 to 20 carbon atoms.