Muramyldipeptide derivatives and influenza vaccine comprising the derivatives
AssigneesDaiichi Pharmaceutical Co., Ltd., The Chemo-Sero-Therapeutic Research Institute
InventorsMasaharu Oki, Hideya Tsuge, Kunio Ohkuma, Tetsuya Oka
Life of this patent
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Abstract
Novel muramyldipeptide derivatives such as [6-0-(2-tetradecylhexadecanoyl)-N-acetylmuramoyl]-L-alanyl-D-glutamamide and [6-0-(2-tetradecylhexadecanoyl)-N-acetylmuramoyl]-L-alanyl-N -methyl-D-glutamamide are provided. The muramyldipeptide derivatives are excellent compound as an adjuvant or a constituting component of virosome vaccine. An influenza vaccine comprises a complex of the muramyldipeptide derivative and an influenza virus antigen. The influenza vaccine has excellent antibody-producing capacity and safety.
Claims15
Muramyldipeptide derivatives of the following general formula (I) and salts thereof:
- ##STR4## wherein R represents an acyl group having 2 to 6 carbon atoms, X represents L-alanine residue, A represents a branched fatty acid residue having 20 to 60 carbon atoms, and R.sub.1 and R.sub.2 independently represent a hydrogen atom or a substituted or unsubstituted lower alkyl group.
A muramyldipeptide derivative selected from the group consisting of [6-0-(2-tetradecylhexadecanoyl)-N-acetylmuramoyl]-L-alanyl-D-glutamamide, [6-0-(2-tetradecylhexadecanoyl)-N-acetylmuramoyl]-L-alanyl-N-methyl-D-glut amamide and [6-0-(2-Tetradecylhexadecanoyl)-N-acetylmuramoyl]-L-alanyl-N-ethyl-D-gluta mamide.
An influenza vaccine comprising a complex of a compound of the general formula (I):
- ##STR5## wherein R represents an acyl group have 2 to 6 carbon atoms, X represent L-alanine residue, A represents a branched fatty acid residue having 20 to 60 carbon atoms, and R.sub.1 and R.sub.2 independently represent a hydrogen atom or a substituted or unsubstituted lower alkyl group or a salt thereof and influenza hemagglutinin neuraminidase antigen.
Dependencies are inferred from the claim text.