Muramyl peptide derivatives and pharmaceutical compositions
AssigneeAgence Nationale de Valorisation de la Recherche (ANVAR)
InventorsPierre Lefrancier, Monique Parant, Francoise Audibert, Edgar Sache, Louis Chedid, Jean Choay, Edgar Lederer
Life of this patent
Estimating the term…
Abstract
The invention relates to new compounds useful notably as regulator of immune responses and which are derivatives of muramyl peptides substituted at the end of the peptide chain by a group containing at least four carbon atoms.
Claims49
A compound which is an immunological adjuvant and effective against Klebsiella, which compound has the formula:
- ##STR18## in which the substituents R, R.sub.1, R.sub.2, R.sub.4, R.sub.6, X, Y and Z has the following definition:
- R is hydrogen or an alkyl group having 1 to 4 carbon atoms,
- R.sub.1 is hydrogen hydroxyl or phenylamino,
- R.sub.2 is hydrogen or methyl,
- R.sub.4 is hydrogen or acyl group having 1 to 4 carbon atoms,
- R.sub.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.sub.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.sub.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.sub.2 -CH.sub.2 O-COR' or -OCH.sub.2 -CHOH-CH.sub.2 O-R.degree., wherein
- R.degree. 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.
A compound which has anti-Listeria activity, which compound has the formula ##STR19## wherein Y is selected from the group consisting of hydroxy, amino and alkoxy of 1 to 10 carbon atoms, and
- R.sup.1 is a linear or branched alkyl group having 4 to 20 carbon atoms or -OCH.sub.2 -OCHOH-CH.sub.2 O-R.degree., wherein R.degree. a mycolic acid group having from 80 to 90 carbon atoms.
Dependencies are inferred from the claim text.