Agence Nationale De Valorisation De La Recherche (anvar)

Agence Nationale De Valorisation De La Recherche

Vacsyn S.a.

Agence Nationale De Valorisation

Univ. of Tennessee Research Corp.

Francoise Marguerite Audibert

Louis A Chedid

Pierre Lefrancier

Jean Choay

Edgar Lederer

Monique Parant

Pierre G Sinay

Jean-Francois Petit

Arlette Adam

Rita Ciorbaru

Claude Merser

Fabrielle Ellouz

Dominique Juy

Edgar Sache

Michel Level

Michael Sela

Edwin H Beachey

Andre Tartar

Helene Gras-Masse

Claude Carelli

Nigel Phillips

Marcel Derrien

Pierre Le Francier

Jean-Marie Bernard

Michel Jolivet

Enhanced immunogenic vaccine

The invention relates to muramyleptide derivatives resulting essentially from the conjugation or the coupling, as the case may require, through an arm, between a muramylpeptide and a group containing two atoms contiguous with one another to each of which is attached a lipophile chain comprising from 8 to 100 carbon atoms, preferably from 14 to 24 carbon atoms. The derivatives according to the invention are endowed with remarkable stimulating properties with respect to the activation of macrophages, of which they amplify the tumoricidal properties.

Lipophile derivatives of muramylpeptides having properties of activating

Peptide fragment of M protein of S. pyrogenes elecit opsonic antibodies which are type-specific for type 24 streptococci.

Synthetic peptide compounds

The compounds have the structure 2-(2-amino or alkyl-amido-2-desoxy-3-O-D-glucopyranosyl)-alkanyl-dipeptide, possibly substituted on the saccharide residue the amino acid residue at the end of the peptide chain being a D-glutamyl residue whose .alpha.-carboxy function is esterified and .gamma.-carboxyl function amidated. The compounds are valuable as immunological medicaments.

Novel compounds of the muramyl peptide

The invention relates to an immunogenic principle containing a specific antigen determinant of a predetermined native antigen. This immunogenic principle is constituted by a conjugate between a hapten bearing said antigenic site and a muramyl-peptide, essentially in the absence of supporting macromolecules, this conjugate having an immunogenic effect not only against itself, but also with respect to the native antigen carrying said antigenic site.

Conjugates of haptenes and muramyl-peptides, endowed with immunogenic

The novel products are water-soluble oligomers, free of N-acetyl-glucosamine units, and of which the monomer elements include a group derived from muramic acid on which is fixed a chain of the peptide type including at least two aminoacyl residues, the first being selected from among: L-alanyl, L-arginyl, L-asparagyl, L-histidyl, L-hydroxyprolyl, L-isoleucyl, L-leucyl, L-methionyl, L-phenylalanyl, L-prolyl, L-seryl, L-threonyl, L-tryptophanyl, L-valyl, and the second aminoacyl is D-glutamyl or D-isoglutaminyl. They are useful for their immunoregulator properties and for the preparation of pharmaceutical compositions.

Oligomers of compounds of the muramyl-peptide type and medicaments

The invention relates to novel compounds of the muramyl-peptide type and to their uses. The muramyl-peptides according to the invention comprise at least two aminoacyl residues in the peptide chain, the second of these aminoacyl residues being D-glutamyl, and they are characterized in that the nitrogen of the first amino-acyl, and forming part of the pepetide linkage connecting the muramyl group to the peptide residue, is substituted by an alkyl group. These compounds are useful notably for the preparation of pharmaceutical compositions, in particular by reason of their regulatory properties on the immune responses of the organism.

Muramyl peptide substituted on a peptide nitrogen and medicaments

A polymer of peptidic type formed by a chain formed from aminoacyl residues preferably derived of at least one of the amino-acid residues selected from the class consisting of .alpha.,.gamma.-diaminobutyric acid, ornithine, lysine, homo-lysine, of which the lateral amino functions portionally carry peptide branches of which the aminoacyl residues are preferably derived of those selected from the class consisting of alanine, glycine, .alpha.-aminobutyric acid, valine, leucine and proline, the above-said peptide polymer having an average molecular weight comprised between about 50,000 and 250,000, and to which are bound covalently, muramyl-peptide units of which the two first aminoacid residues bound to the muramyl group are stereoisomers of the D series, the second aminoacid residue having the structure of the glutamic acid. This product is useful as anti-infectious agent.

Muramyl-peptides fixed to peptide-polymers and pharmaceutical

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.

Muramyl peptide derivatives and pharmaceutical compositions

Water soluble agents effective as immunological adjuvants for stimulating in the host the immune response to various antigens, comprising an acyl-muramic acid group, wherein acyl means acetyl or glycolyl, and a short peptide chain linked to said acyl-muramic acid group, the first and second amino acids of said peptide chain being preferentially alanine and glutamic acid respectively.

Water soluble agents effective as immunological adjuvants for

The invention relates to water-soluble biologically active agents, having anti-infectious and adjuvant properties. They have the general formula ##STR1## wherein X, Y, Z, R.sub.2, R.sub.4 and R.sub.6 have the meanings defined in claim 1. The invention also relates to pharmaceutical compositions containing these compounds in association with a pharmaceutical vehicle, particularly an oil-free one.

Biologically active compositions and methods of use

Compounds derived from N-acetyl-nor-muramyl-L-alanyl-D-isoglutamic acid

The invention relates more particularly to the diamide of the 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-glutam ic acid, to the pharmaceutical compositions containing said compound in association with a pharmaceutical vehicle. Of particular interest are the oil-free compositions containing said compound, particularly the oil-free aqueous sterile isotonic injectable solutions. These compositions are useful as adjuvants for enhancing the immune response to vaccinant antigens, particularly weak immunogens.

Growing community of inventors

Neuilly-sur-Seine, France

Francoise Marguerite Audibert