CA2011275A1 - Muramyl peptide derivatives and immunoregulating compositions containing them - Google Patents

Muramyl peptide derivatives and immunoregulating compositions containing them

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Publication number
CA2011275A1
CA2011275A1 CA002011275A CA2011275A CA2011275A1 CA 2011275 A1 CA2011275 A1 CA 2011275A1 CA 002011275 A CA002011275 A CA 002011275A CA 2011275 A CA2011275 A CA 2011275A CA 2011275 A1 CA2011275 A1 CA 2011275A1
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CA
Canada
Prior art keywords
alanyl
dideoxy
methylester
acetamido
lactoyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
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CA002011275A
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French (fr)
Inventor
Akira Hasegawa
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Individual
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Individual
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Publication of CA2011275A1 publication Critical patent/CA2011275A1/en
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
    • C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
    • C07K9/005—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure containing within the molecule the substructure with m, n > 0 and m+n > 0, A, B, D, E being heteroatoms; X being a bond or a chain, e.g. muramylpeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
    • A61K2039/55511—Organic adjuvants
    • A61K2039/5555—Muramyl dipeptides

Abstract

ABSTRACT OF THE DISCLOSURE

Muramyl peptide derivatives of the formula :

(I) wherein "Ala" is ; "isoGln" is ;
R1 is R3O- or R3S-[R3 is (k is an integer from 8 to 12; q is an integer from 10 to 22) or R3 is (m is an integer from 11 to 17; n is an integer from 11 to 17)]; and R2 is hydrogen atom or -CO-(CH2)p-CH3 (p is an integer from 8 to 22);

which act on in vivo immunomechanism of human beings and livestock (in particular cells relevant immue responses) and are useful as immunoregulating agents.

Description

2~ ~ 2~3 TITLE OF THE INVENTION

Muramyl pepti.de deriva-tives and immunoregulating compositions containing them BACKGROUND OF THE INVENTION
1. Field of the Invention The present invention relates to novel muramyl peptide derivatives. The muramyl peptide derivatives of the present invention acts on in vivo immunomechanism of human beings and livestock (in particular cells relevant to immune responses) and are useful as immunoregulating agents.
2. Description of the Pri.or Art Muramyl peptides are known to possess various biological activities. That is, they possess in vitro activities such as;
(1) the action on cells related to immune responses (for example, monocytes or macrophages, B cells, T
cells, natural killer (NK) cells and the like), (2~ the action on cells other than those mentioned above (for example, platelets, cndothel.i.a:L celLs, :Eibroblasts and thc like), and (3) the action which activates complement systems.
Further they show in vivo activities such as (1) immunoregulating action, and (2) enhancement of natural resistance [see Saishin Igaku, 43, No.
6, pp. 1268-1276 (1988) in Japan].

Known muramyl peptide derivatives are, for example, B30-muramyl dipeptide [Kusumoto et al;
Tetrahedron letters, 49 pp. 4899-4902(1978)], muramyl dipetide-lysine [Matsumoto et al, Immunostimulants, pp.
79-97 (1987)] and those discribed in Japanese Published Unexamined Patent Application Nos. 172399/1983, 20297/1984 and 275299/1986.
However, it is still desired to develop compounds other than the known muramyl dipeptide derivatives which have more excellent activity and less toxicity.

Sln~MARY OF THE INVENTION
According to the present inven-tion, a muramyl dipeptide derivative is provided, which is represented with the following formula (I):

~L
~ ~ H,~

CH3/CH li 3 C=O O
Ala-isoGln-OCH3 2 01~ 2 7 ~

CIH3 lONH2 wherein "Ala" is -NH-CH-CO-; "isoGln" is -NH-CH-CH2CH2CO-;
R1 is R30- or R3S- [R3 is -CO-CH -CH-(CH ) -CH

o CO (CH2)q~CH3 (k is an integer from 8 to 12; g is an integer from 10 to 22) or R3 is -CO-CH-(CH2)m-CH3 (m is an integer from (CH2)n-CH3 11 to 17; n is an integer from 11 to 17)]; and R2 is a hydrogen atom or-CO-(CH2)p-CH3 (p is an integer from 8 to 22).
The present inventi,on also provides an immunoregulating composition comprising a compound of the formula (I) and a pharmaceutically acceptable carrier.

DESCRIPTION OF THE PREFERRED EMBODIMENTS
In the formula (I), examples of the groups R3 in the group -OR3 or -SR3 include 3-dodecanoyloxy-dodecanoyl., 3-tridecanoyloxydodecanoyl., 3-t:etradccanoy-loxydodecanoyl, 3-pentadecanoyloxydodecanoyl, 3-hexa-decanoyloxydodecanoyl, 3-heptadecanoyloxydodecanoyl, 3-2 0 ~ 127 ~

octadecanoyloxydodecanoyl, 3-nonadecanoyloxydodecanoyl, 3-eicosanoyloxydodecanoyl, 3-docosanoyloxydodecanoyl, 3-heneicosanoyloxydodecanoyl, 3-tricosanoyloxydodeca-noyl, 3-tetracosanoyloxydodecanoyl, 3-dodecanoyloxy-tridecanoyl, 3-tridecanoyloxytridecanoyl, 3-tetradecanoyl.oxytridecanoyl, 3-pentadecanoyloxytri-decanoyl, 3-hexadecanoyloxytridecanoyl, 3-heptadecanoy-loxytridecanoyl, 3-octadecanoyloxytridecanoyl, 3-non-adecanoyloxytridecanoyl, 3-eicosanoyloxytridecanoyl, 3-docosanoyloxytridecanoyl, 3-heneicosanoyloxytrideca-noyl, 3-tricosanoyloxytridecanoyl, 3-tetracosanoyloxy-tridecanoyl, 3-dodecanoyloxytetradecanoyl, 3-trideca-noyloxytetradecanoyl, 3-tetradecanoyloxytetradecanoyl, 3-pentadecanoyloxytetradecanoyl, 3-hexadecanoyloxy-tetradecanoyl, 3-heptadecanoyloxytetradecanoyl, 3-octadecanoyloxytetradecanoyl, 3-nonadecanoyloxytetra-decanoyl, 3-eicosanoyloxytetradecanoyl, 3-docosanoy-loxytetradecanoyl, 3-heneicosanoyloxytetradecanoyl, 3-tricosanoyloxytetradecanoyl, 3-tetracosanoyloxytetra-decanoyl, 3-dodecanoyloxypentadecanoyl, 3-tridecanoy-loxypentadecanoyl, 3-tetradecanoyloxypentadecanoyl, 3-pentadecanoyloxypentadecanoyl, 3-hexadecanoyloxy-pentadecanoyl, 3-heptadecanoyloxypentadedanoyl, 3-octadecanoyloxypentadecanoyl, 3-nonadecanoyloxypenta-decanoyl, 3-eicosanoyloxypentadecanoyl, 3-docosanoy-2 ~

lo~ypentadecanoyl, 3-heneicosanoyloxypentadecanoyl, 3-tricosnoyloxypentadecanoyl, 3-tetracosanoyloxypenta-decanoyl, 3-dodecanoyloxyhexadecanoyl., 3-tridecanoy-loxyhexadecanoyl, 3-tetradecanoyloxyhexadecanoyl, 3-pentadecanoyloxyhexadecanoyl, 3-hexadecanoyloxyhexa-decanoyl, 3-heptadecanoyloxyhexadecanoyl, 3-octa-decanoyloxyhexadecanoyl, 3-nonadecanoyloxyhexadecanoyl, 3-eicosanoyloxyhexadecanoyl, 3-docosanoyloxyhexa-decanoyl, 3-heneicosanoyloxyhexad2canoyl, 3-tricosanoy-loxyhexadecanoyl, 3-tetracosanoyloxyhexadecanoyl, 2-dodecyltetradecanoyl, 2-tridecyltetradecanoyl, 2-tetradecyltetradecanoyl, 2-pentadecyltetradecanoyl, 2-hexadecyltetradecanoyl, 2-heptadecyltetradecanoyl, 2-octadecyltetradecanoyl, 2-tetradecylpentadecanoyl, 2-pentadecylpentadecanoyl, 2-hexadecylpentadecanoyl, 2-heptadecylpentadecanoyl, 2-octadecylpentadecanoyl, 2-dodecylhexadecanoyl, 2-tridecylhexadecanoyl, 2-tetra-decylhexadecanoyl, 2-pentadecylhexadecanoyl, 2-hexa-decylhexadecanoyl, 2-heptadecylhexadecanoyl, 2-octa-decylhexadecanoyl, 2-dodecylpentadecarloy.l., 2-tri.decylpcntadecanoyl, 2-tetradecylpentadccanoyl, 2-pentadecylpentadecanoyl, 2-hexadecylperltadecanoyl, 2-heptadecylpentadecanoyl, 2-octadecylpentadecanoyl, 2-dodecylhexadecanoyl, 2-tridecylhexadecanoyl, 2-tetradecylhexadecanoyl, 2-pentadecylhexadecanoyl, 2~27~3 2-hexadecylhexadecanoyl,2-heptadecylhexadecanoyl, 2-octadecylhexadecanoyl,2-dodecylheptadecanoyl, 2-tridecylheptadecanoyl,2-tetradecylheptadecanoyl, 2-pentadecylheptadecanoyl, 2-hexadecylheptadecanoyl, 2-octadecylheptadecanoyl, 2-dodecylocta- decanoyl, 2-tridecyloctadecanoyol, 2-tetradecylocta- decanoyl, 2-pentadecyloctadecanoyl, 2-hexadecylocta- decanoyl, 2-heptadecyloctadecanoyl, 2-octadecylocta- decanoyl, 2-dodecylnonadecanoyl, 2-tridecylnona- decanoyl, 2-tetradecylnonadecanoyl, 2-pentadecylnona- decanoyl, 2-hexadecylnonadecanoyl, 2-heptadecylnona- decanoyl, 2-octadecylnonadecanoyl, 2-dodecyleicosanoyl, 2-tridecyleicosanoyl, 2-tetradecyleicosanoyl, 2-penta-decyleicosanoyl, 2-hexadecyleicosanoyl, 2-heptadecyl-eicosanoyl and 2-octadecyleicosanoyl groups.
Preferred groups of R3 are 3-tetradecanoyloxy-tetradecanoyl, 3-hexadecanoyloxytetradecanoyl, 3-octadecanoyloxytetradecanoyl, 3-tetracosanoyloxy-tetradecanoyl and 2-tetradecylhexadecanoyl groups.
Examples of R2 include hydrogen atom, decanoyl, undecanoyl, dodecanoyl, tridecanoyl, tetradecanoyl, pentadecanoyl, hexadecanoyl, heptadecanoyl, octadeca-noyl, nonadecanoyl, eicosanoyl, docosanoyl, heneicosa-noyl, tricosanoyl and tetracosanoyl groups.

2~ ~27~

R2 is preferably hydrogen atom or tetradecanoyl group.
PreFerably, "Ala" is an L-alanine residue, and "isoGln" is a residue derivated from D-isoglutamine.
The compounds of the formula (I) of the present invention are basically muramyl dipeptide derivatives, in which the muramyl dipeptide moiety has preferably the same steric configuration as that of the muramyl dipeptide moiety in natural muramyl dipeptides.
Namely, the moieties oE muraminic acid and dipeptide in the present muramyl dipeptides have D-steric configu-ration and L-alanine-D-isoglutamine configuration, respectively. However, the muramyl dipeptides of the present invention may be those having other possible steric configurations.
The group -OR3 or -SR3 in the definition of the formula (I) preferably combines with the saccharide moiety in the form of a-bond and ~-bond, respectively.
The acyloxyacyl group in R3 has an asymmetric carbon atom and may be in the form of D- or L-isomer, or racemic mixture.
Intercsting compourl~s beloncling to the Eormula (I) in the present invention include:

N-~2-0-{2-Acetamido-2,3-dideoxy-1-0-(2-tetra~ecyl-hexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-0-(2-tetradecylhexadecanoyl)-a-D-glucopyranos-3-yl}-~-lactoyl]-L-alanyl-D-isoglutarnine methylester N-l2-0-{2-Acetamido-2,3-dideoxy-6-O-tetradeca3loyl-1-0-(2-tetradecylhexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-12-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-0-~2-tetradecylhexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-~cetamido-2,3-dideoxy-1-S-(2-tetradecyl-hexadecanoyl)-1-t~io-~-D-glucopyranos-3-yl3-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-(2-tetradecylhexadecanoyl)-1-thio-13-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-tetradecanoyl-1-S-(2-tetradecylhexadecanoyl)-1-thio-~-D-glucopyranos~
3-yl}-D-lactoyl]-L-alanyl-D-i.soglutamin~ mcthylcst~r N-[2-o-{2-Acetamido-2~3-td:Ldeoxy-6-o-octad~canc)yl-1-S--(2-tetradecylhexadecanoyl)-1-th:Lo-13~D-glucopyranos-3-yl}-D-lactoyl]-L.-alanyl-D-isoglutamine methylester 2 ~ 2 ~.5 N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-tetra-decanoyloxytetradecanoyl)--D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{~-Acetamido-2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-tetradecanolyloxytetradecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-~2-0-{2-Acetamido-2,3-dideoxy-6-0-tetradecanoyl-1-0-((3R)-3-tetradecanoyloxytetradecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-0-((3R)-3-tetradecanoyloxytetradecanoyl)--D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-1-S-((3R)-3-tetra-decanoyloxytetradecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-tetradecanoyloxytetradecanoyl)-:1-th.io-~-D-glucopyranos-3-yl}-D-lactoyL~-~.,-al.arlyl.-D-i.sog.Lutamine methylester 2 (~ 2 7 ~

N-~Z-0-{2-Acetamido-2,3-dideoxy-6-0-tetradecanoyl-1-S-((3R)-3-tetradecanoyloxytetradecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-S-((3R)-3-tetradecanoyloxytetradeeanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-hexa-decanoyloxytetradecanoyl)-a-D-glucopyranos-~-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-hexadecanoyloxytetradecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-~(3R)-3-hexa-decanoyloxytetradecanoyl-6-0-tetradecanoyl-a-D-glueopy-ranos-3-yl3-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-hexa-decanoyloxytetradecanoyl)-6-0-oetadecanoyl-a-D-glueo-pyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy-1-S-((3R)-3-hexa-decanoyloxytetradeeanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester 2~ ~27;~

~-~2-0-{2-Acetamido-2,3-dideoxy-6~0-decanoyl-1-S-(~3R)-3-hexadecanoyloxytetradecanoyl)-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1.-S-((3R)-3-hexa-decanoyloxytetradecanoyl)-6-0-tetradecanoyl-~--thio.-~-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-~(3R)-3-hexa-decanoyloxytetradecanoyl)-6-0-octadecanoyl-1-thio-B-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-~2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-octa-decanoyloxytetradecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl~-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-hexadecanoyloxytetradecanoyl)-a-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-octa-decanoyloxytetradecanoyl)-6-0-tetradecanoyl-a-D-gluco-pyranos-3-yll-D-lactoy:ll-L,-alanyl. ~:lsoglutallllne methylestcr N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-0-((3R)-3-octadecanoyloxytetradecanoyl)-a-D-gluco-2 ~3 ~

pyranos-3-yl}-D-lactoyl]-L-alanyl-D~-isoglutamine methylester N-[2-0-{2-Acetarnido-2,3-dideoY.y-1-S-((3R)-3-octa-decanoyloxytetradeeanoyl)-1-thio-~-D-gl~copyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutmine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-deeanoyl-1-S-((3R)-3-octadecanoyloxytetradeeanoyl)-l-thio-~-D-glueo-pyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy-1-S-((3R)-3-oeta-decanoyloxytetradeeanoyl)-6-0-tetradeeanoyl-1-thio-~-D-glueopyranos~3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy-6-0-oetadeeanoyl-1-S-((3R)-3-octadeeanoyloxytetradeeanoyl)-1-thio-B-D-glueopyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy-1-0-((3R)-3-tetra-eosanoyloxytetradeeanoyl)-a-D-glueopyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylest~r N-[2-0-{2-Aeetamido-~,3-d:idc~o~y~6-0-deeclnoyl-l-O-((3R)-3-tetraeosanoyloxytetrad~canoyl)-a-D-glueo-pyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester 2 '~ ~

~ 1-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-tetra-cosanoyloxytetradecanoyl)-5-0-tetradecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetarnido-2,3-dideoxy-6-0-octadecanoyl-1-0-((3R)-3-tetracosanoyloxytetradecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-tetra-cosanoyloxytetradecanoyl)-1-thio-L~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-tetracosanoyloxytetradeeanoyl)-1-thio-L~-D-gluco-pyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-tetra-cosanoyloxytetradeeanoyl)-6-0-tetradeeanoyl-1-thio-~-D-glueopyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy-6-0-oetadeeanoyl-1-S-((3R)-3-tetraeosanoyloxytetratlt-~eanoy:L)-1-l-.hio-B-L)-glueopyranos-3-yl}-D-laetoyl~-L-alallyl-:D-isoglutaloille methylester 2 ~

N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-0-(2-tetradecylhexadecanoyl)-a-D-glucopyranos-3-yl}-d-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadeca~oyl-1-0-(2-tetradecylllexadecanoyl)-a-D-glucpyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-~2-0-(2-Aeetamido-2,3-dideoxy-6-0-dodeeanoyl-1-S-(2-tetradecylhexadecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methyester N-[2-0-(2-Aeetamido-2,3-dideoxy-6-0-hyxadecanoyl-1-S-(2-tetradecylhexadecanoyl)-1-thio-~-D-glueopyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methyester N-[2-0-{2-Aeetamido~2,3-dideoxy-1-0-((3R)-3-dodecanoyloxytetradeeanoyl)-a-D-glueopyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy-6-0-deeanoyl-1-0-((3R)-3-dodeeanoyloxytetradeeanoyl)-~ D-glueopyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy-6-0-dodeeanoyl-1-0-((3R)-dodeeanoyloxytetradeeanoyl)-a-D-glueopy:ranos-3-yl}-D-lactoyl]-L-alanyl-D-i.so~:l.ut:ami.ne methy:Lc3~er N-[2-0-{2-Aeetamido-2,3-dideoxy-1-0-~3R)-3-dodeeanoyloxytetradeeanoyl)-6-0-tetradeeanoyl-~-D-glueopyranos-3-yl}-D-laetoyl]-L-alanyl-V-isoglutamine methylester 2 ~ 7 3 N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-dodecanoyloxytetradecanoyl)-6-0-hexadecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-~,-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-dodecanoyloxytetradecanoyl)-6-0-octadecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3--dideoxy-1-S-((3R)-3-dodecanoyloxytetradecnaoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-12-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-dodecanoyloxytetradecanoyl)-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-((3R)~3-dodecanoyloxytetradecanoyl)-1-thio-~-D-~luco-pyranos-3-yl}-D~-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-dodecanoyloxyte-tradecanoyl)-6-0-tet.radecanoy'l-~.~thio-~-D-glucopyranos-3-y'l}-D-lactoyl~-L-alarlyJ.-D-iso-glutamine methylester N-[2-0-{2-Acetamido-2,3-d,ideoxy-1-S-((3R)-3-dodecanoyloxytetradecanoyl)-6-0-hexadecarloyl-1-thio-~-2 ~

D-glucopyranos-3-yl.}-D-lactoyl]-L-alanyl.-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-dodecanoyloxytetradecanoyl-6-0-octadecanoyl-1-thi.o-~-D-glucopyranos-3-yl}-D-lactoyll-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-0-dodecanoyl-1-0-((3R)-3-tetradecanoyloxytetradecanoyl-a-D-glucopyranos-3-yl}-D-lactoyl}-L-alanyl-D-isogluta-mine methylester N-~2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-l-0-((3R)-3-tetradecanoyloxytetradecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-((3R)-3-tetradecanoyloxytetradecanoy].)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-~2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-1-$-((3R)-3-tetradecanoyloxytetradecanoyl)-1-thio-~-D-glucopyranos-3-yl)-D-lactoyl~-L-alallyl--D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1 20~ 1 2 ~3 0-((3R)-l-hexadecanoyloxytetradesanoyl)-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-is~glutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6--0-hexadecanoyl-1-0-((3R)-3-hexadecanoyloxytetradecanoyl)-a-D-gluco-pyranos-3-yl)-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2 0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-(~3R)-3-hexadecanoyloxytetradecanoyll ~-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-1-S-~(3R)-3-hexadecanoyloxytetradecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1 0-((3R)-3-hexadecanoyloxytetradecanoyl)-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-1-0-((3R)-3 octadecanoyloxyt~tradccarloyl)-~ D-gl~lco pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-((3R)-3-octadecanoyloxytetradecanoyl)-1-thio-~-D-2~ ~ 2~

glucopyranos-3~yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-l-S-(~3R)-3 o~tadecanoyloxytetradecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-~3R)-3-eicosa noyloxytetradecanoyl)--D-glucopyranos-3-yl}-D-lactoyl]- L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-eicosanoyloxytetradecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-0-l(3R)-3-eicosanoyloxytetradecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-~(3R)-3-eeicosanoyloxytetradecanoyl)-6-0-tetradecanoyl-a-D-glucopyranos-3-yl3-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-(~3R)-3-eicosanoyloxytetradecarloy:L)-~-O-h~xadccar~ 'L-a-D-g'luco-pyranos-3-yl3-D-Lactoyl]-L--alany:L-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-1-0-((3R)-3-eicosanoyloxytetrdecanoyl)-6-0-octadecanoyl-a-D-gluco-2~ ~ 27~3 pyrarlos-3~ }-D-lactoyl)-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamid~-2,3-dideoxy-1-S-((3R)-3-ei.cosanoyloxytetradecanoyl)-1-thio-B-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-eicosanoyloxytetradecanoyl)-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-eicosanoyloxytetradecanoyl)-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-I.-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-i-S-((3R)-3-eicosanoyloxytetradecanoyl)-6-0-tetradecanoyll-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-eicosanoyloxytetradecanoyl)-6-0-hexadecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-~ideoxy-1-S-t(3R)-3-eicosanoyloxytetradecanoyl)-6-0-octadecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester 2 ~ 7 ~

N-[2-0-{~-Acetamido-2,3-dideoxy-1-0-((3R)-3-docosanoyloxytetradecanoyl)-a-D-glucopyranos-3-yl}-D-l-actoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-docosanoyloxytetradecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-(~3R)-3-docosanoyloxytetradecanoyl)-6-0-decanoyl-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-docosanoyloxytetradecanoyl)-6-0-tetradecanoyl-a-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-docosanoyloxytetradecanoyl-6-0-hexadecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-docosanoyloxytetradecanoyl)-6-0-octadecanoyl-a-D-gluco-pyranos-3-yl3-D lactoyl~-L-alanyl-D-lsoglutamin~
methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-docosanoyloxytetradecanoyl)-1-thio-~-D-glucopyranos-~ 20 3--yl~-D-:Iactoyll-L,-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-docosanoyloxytetradeeanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-V-isoglutamine methylester N-[2-0-~2-~cetamido-2,3-dideoxy-1-S-((3R)-3-docosanoyloxytetradecanoy:L)-6-0-dodecanoyl-1-thio-~-D-glucopyranos-3-yl~-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-docosanoyloxytetradecanoyl)-6-0-tetradecanoyl-1-thio-B-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-12-Acetamido-2,3-dideoxy-1-S-((3R)-3-doeosanoyloxytetradeeanoyl)-6-0-hexadecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-¦2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-doeosanoyloxytetradeeanoyl)-6-0-octadecanoyl-1-thio-B-D-glucopyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Aeetalnido-7.,3-cliclcoxy-6~0-dc)deeanoyl.-1-O-((3R)-3-tetracosanoyloxytetLadecaoyl)-a-D-gluco-pyranos-3-yl}-D lactoyl~-L-alanyl-D-isoglutami.ne methylester 2 ~ 7 ~ ~

~ 1-[2-0-{2-Acetainido-2,3-dideoxy-6-0-hexadecanoyl-1-0-~(3R)-3-tetracosanoyloxytetradecanoyl)-a-D-gluco-pyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-((3R)-3-tetracosanoyloxytetradecanoyl) 1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-1-S-(13R)-3-tetracosanoyloxytetradecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-12-dodecyl-tetradecanoyl)-a-D-glucopyranos~3-yl3~D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-~cetamido-2,3-dideoxy-6-0-decanoyl-1 0-(2-dodecyltetradecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-0-(2-dodecyltetradecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine mcthylast~r N-[2-0-{2-Acctamido-~,3-dideoxy-1-0-~2-dodecyl-tetradecanoyl)-6-0-tetradecanoyl-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester 7 ~3 N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-(2-dodecyl-tetradecanoyl)-6-0-hexadecanoyl--D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-lsoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-(2-dodecyl-tetradecanoyl)-6-0-octadecanoyl-a-D-glucopyranos-3-yl}-D-lactoyl~-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-(2-dodecyl-tetradecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-(2-dodecyltetradecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-(2-dodecyltetradecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-l.-alanyl-D-isoglutamlne methylester N-[2-0-~2~Acetamido-2,3-dideoxy-1-S-(2-dodecyl-tetradecanoyl)-6-0-tetradecanoyl-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-~2-dodecyl-tetradecanoyl.)-6-0-hcxadecanoyL-l-thio-~-D g:Luco-pyranos-3-yl}-D-lactoyl~-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-~2-dodecyl-tetradecanoyl)-6-0-octadecanoyl-1-thio-~-D-gluco-2~ ~27~-j pyranos-3-yl)-D-iactoyl]-L-alanyl-D-isoglutamine methylester N-12-0-~2-Acetamido-2,3-dideoxy~1-0-~2-hexadecyl-octadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L
alanyl-D-isoglutamine methylester N-[2-0-{2-Acetami.do-2,3-dideoxy-6-0-decanoyl-1-0-(2-hexadecyloctadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acctamido-2,3-dideoxy-6-0-dodecanoyl-1-0~(2-hexadecyloctadecanoyl)-a-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-(2-hexadecyl-octadecanoyl)-6-0-tetradecanoyl-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-1-0-~2-hexadecyloctadecanoyl)-~-D--glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-(2-hexadecyl-octadecanoyl)-6-0-octadecanoyl-a-D-glucopyranos-3-yl}-D-lactoyl]-l.-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-d:idcoxy-1--S-(2-llcxadccyl-octadccanoyl)-:L-thio-B-D-glucopyrallos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester 2 ~ 7 ~

N-[2-0-~2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-~2-hexadecyl,octad~canoyl)-1-thio-13-D-c31ucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-(2-hexadecyLoctadecanoyl)-l-thio-B-D-glueopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-E2-0-{2-Aeetamido--2,3-dicleoxy-1-S-~2-hexadecyl-oetadeeanoyl)-6-0-tetradecanoyl-1-thio-~-D-glueo-pyranos-3-yl}-D-lactoyl~-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-l-S-(2-hexadecyloctadeeanoyl)-1-thio-~-D-glucopyranos-3-yl3-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy-1-S-~2-hexadeeyl-oetadeeanoyl)-6-0-oetadeeanoyl l-thio-~-D-glucopyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy-1-0-(2-oetadeeyl-eicosanoyl)-a-D--glueopyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy-6-0-deeanoyl-1-0-(2-oetadeeyleisoeanoyl)-a-D-cllueopyranos-3-y:L}-O-lactoyl]-L-alanyl-D-Lsogl.utclmine metlly:Lest.e:r N-[2-0-{2-Aeetamido-2,3--dideoxy-6-0-dodeeanoyl-1-0-(2-oetadeeyleieosanoyl)-a-D-glueopyrano.s-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester 2~ 2 ~J~1 N-[2-Q-~2-Acetamido-2,3-dideoxy-1-0-(2-octadecyl-eicosanoyl)-6-0-tetradecanoyl-a-D-glucopyranos-3-yl}-D-lactoyl]-~-alanyl-D-isoglutamine methylester N-[2-0-{2-~cetamido-2,3 dideoxy-6-0-hexadecanoyl-1-0-(2-octadecyleicosanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-0-(2-octadecy}eicosanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-1-S-(2-octadecyl-eicosanoyl)-1-thio-f~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-(2-octadecyleicosanoyl)-1-thio-f~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-(2-octadecyleicosanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-l,-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-(2-octadecyl-eicosanoyl)-6-0-tetradecanoyl-1-thio-Ç~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-].sog:lut:aminc mcthylc~ster N-[2-0-(2-Acctamido-Z,3-dideox~-6-0-h~xadecanoy:l-l-S-(2-octadecyleicosanoyl)-1-thio-r~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester 2 ~ 7 ~

N-~2-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-S-(2-octadecyleicosanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-(2-dodecyl-hexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dec~noyl-1-0-(2-dodecylhexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-0-(2-dodecylhexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-(2-dodecyl-hexadecanoyl)-6-0-tetradecanoyl-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-~2-0-{2-Acetamido-2,3-dideoxy-1-0-(2-dodecyl-hexadecanoyl)-6-0-hexadecanoyl-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-(2-dodecyl-hexadecanoyl)-6-0-octadecanoyl-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Ac~tamido-2,3-dideox~ (2-cloc~ecyl-hexadecanoyl)-1-thio-~-D-glucopyranos-3-yl)-D-lactoyll-L-alanyl-D-isoglutamine methylester 2 0 ~ l 2 1 ~ ~

N-[2-0-~2-Acetam~do-2,3-dideoxy-6-0-decanoyl-1-S-t2-dodecylhexadecanoyl)-1 thio-~-D-glucopyranos-3-yl}
D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-6-0-dodeeanoyl-1-S-(2-dodecylhexadecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy-1-S-(2-dodecyl-hexadecanoyl)-6-0-tetradecanoyl-1-thio-B-D-gluco-pyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Aeetamido-2,3-dideoxy-1-S-~2-dodeeyl-hexadeeanoyl)-6-0-hexadecanoyl-1-thio-~-D-gluco-pyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy-1-S-(2-dodeeyl-hexadeeanoyl)-6-0-oet.adeeanoyl-1-thio-~-D-glueo-pyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-~2-0-{2-Aeetamido-2,3-dideoxy-1-0-(2-dodeeyl-octadeeanoyl)-a-D-glueopyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-(2-Aeetamido-2,3-d~deoxy-6-~-tlecarloyl-1-0-(2-dodeeyloetadeeanoy:L)-a-D-glueopyranos-3-yl}-D-laeto-yl]-L- alanyl-D-isoglutamlne methylester 2 ~ 2 7 ~

N-[2-0-~2-Aceta~ido-2,3-dideoxy-6-0-dodecanoyl-1-0-(2~dodecyloctadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl.]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-1-0-(2-dod~cyl-octadecanoyl)-6-0-tetradecanoyl-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-(2-dodecyl-octadecanoyl)-6-0-hexadecanoyl-a-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-(2-dodecyl-octadecanoyl)-6-0-octadecanoyl-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-(2-dodecyl-octadecanoyl)-l-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-t2-dodecyloctadecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-docanoyl-1-S-(2-dodecyloctadecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3 dideoxy-1-S-(2-dodecyl-octadecanoyl)-6-0-tetradecanoyl-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester 2 7 ~j N-[2-0-~2-Acetamido-2,3-dideoxy-1-S-(2-dodecyl-octadecanoyl)-6-0-hexadecanoyl-1-thio-R-D-gluco-pyranos-3-yl)-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-(2-dodecyl-octadecanoyl)-6-0-octadecanoyl-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-(2-dodecyl-eicosanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-0-(2-dodecyleicosanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]
-L-alanyl- D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-0-(2-dodecyleicosanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2.,3-dideoxy-1-0-~2-dodecyl-eicosanoyl)-6-0-tetradecnaoyl-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-didcoxy~1-0-(2-dodecyl-eicosanoyl)-6-0-hexadecarloyl-a-D-glucopyrarlos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester 2 ~ 7 ~

N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-(2-dodecyl-eicosanoyl)-6-0-octadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl~-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-(2-dodecyl-eicosanoyl)-l-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-(2-dodecyleicosanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-(2-dodecyleicosanoyl)-1-thio-B-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-(2-dodecyl-eicosanoyl)-6-0-tetradecanoyl-1-thio-B-D-glucopyranos-3-yl}-D-lactoyl¦-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-(2-dodecyl-eicosanoyl)-6-0-hexadecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl.-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-(2-dodecyl-eicosanoyl)-6-0-octadecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-h-alclnyl-D-isc)gïutaln~ e Illet~y,L(3~!t,e:r N-[2-0-~2-Acet.amiclo-2,3~dideoxy-1.-0 ((3R) 3-dodecanoyloxydodecanoyl)-cl-D-glucopyranos-3-yl}-D-lactoyl]-I.-alanyl-D-isoglutamine methylester 2~ '3 N-[2-0--~2-Acetamido-2,3-dideoxy~6-0-docanoyl-1-0-~3R)-3-dodecanoyloxydodecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl] L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-0-(~3R)-3-dodecanoyloxydodecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-dodecanoyloxydodecanoyl)-6-0-tetradecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-dodecanoyloxydodecanoyl)-6-0-hexadecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-dodecanoyloxydoclecanoyl)-6-0-octadecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-dodecanoyloxydodecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamlrle methy:l.estel N-[2-0-{2-Acctamido-2,3-dideoxy-~-0-docalloyl-1-S-((3R)-3-dodecanoyloxydodecanoyl)-1-thio-~-D-gluco-pyranos-3-yl} D-l.actoyl]-L-alanyl-D-isoglutamine methylester 2 ~

N [ ?.- O - { 2 -Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-((3R~-3-dodecanoyloxydodecanoyl)-l-thio-G-D-gluco-pyranos-3-yl3-D-lactoyl]~ alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-dodecanoyloxydodecanoy].)-6-0-tetradecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methy~.ester N- E 2-0-{2-Acetamido-2,3-dideoxy-1-S-(~3R)-3-dodecanoyloxydodecanoyl)-6-0-hexadecanoyl-1-thio-~-D-gl~copyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{Z-Acetami.do-2,3-dideoxy-1-S-((3R)-3-dodecanoyloxydodecanoyl)-6-0-octadecanoyl-1.-thio-~D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N- E 2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-tetra-decanoyloxydodecanoyl)~a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Ace-tam.ido-2,3-dideoxy-6-0-dodecanoyl-1-0-((3R)-3-t~tadecanoyl.oxydodecarloyl)-a-D-gl.ucopyrallo-s-3- yl3-~-lactoyll-L-alanyl-D-.i.sogllltamirlc methylester N-[2-0-{2-Acetamido-2,3-dldeoxy-6-0-dodecanoyl-1-0-((3R)-3-tetradecanoyloxydodecanoyl)-a-D-c31ucopyranos-3-y]}-D-lactoyl]-L-alanyl-D-isoglutamine methylester 2 ~ 3 N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-tetradecanoyl-1-0-(~3R)-3-ttradecanoy`loxydodecanoyl)-a~D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-1-0-((3R)-3-tetradecanoyloxydodecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-0-(~3R)-3-te-tradecanoyloxydodecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetam~do-2,3-dideoxy-1-S-((3R)-3-tetra-decanoyloxydodecanoyl)-1-thio-B-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-tetradecanoyloxydodecanoyl)-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-((3R)-3-tetradecanoyloxydodecanoyl)-1-~hio-~-D-gluco-pyranos-3-y:l} D-lactoy:L~-L-alany:L-D-i~ogl.utallli.ne methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-tetradecanoyl-2 ~

1-~,-((3R)-3-tetradecanoyloxydodecanoyl)-1-thio-~-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl.-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-1-S-~(3R)-3-tetradecanoyloxydodecanoyl)-1-thio-~-D-glucopyranos-3-yl3-D-lactoyl~-L-alanyl-D-lsoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-S-((3R)-3-tetradecanoyloxydodecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-~2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-hexa-decanoyloxydodecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-hexadecanoyloxydodecanoyl-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-0-((3R)-3-hexadecanoyloxydodecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-hexa-decanoyloxydodecanoyl)-6-0-tetradecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-~-alanyl-D-isoglutami.ne methylester 2~ ~2~

~ '-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl 1-0-((3R)-3-hexadecanoyloxydodecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-hexa-decanoyloxydodecanoyl)-6-0-octadecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl~-L-alanyl-D-~soglutamine methylester N-L2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-hexa-decanoyloxydodecanoyl)-1-thio-B-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-hexadecanoyloxydodecanoyl)-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-((3R)-3-hexadecanoyloxydodecanoyl)-1-thio-~-D-gluco-pyxanos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2,Acetamido-2,3-dideoxy-1-S-((3R)-3-hexa-decanoyloxydodecanoyl)-6-0-tetradccanoyl-1-th.io-~-D-glucopyranos-3-y:l.}-1)-1actoyl]-1.-alanyL-D-:Lso~lutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-1-S-((3R)-3-hexadecanoyloxydodecanoyl)-1-thio-~-D--2~ 2~

glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-~(3R)-3-hexa-decanoyloxydodecanoyl)-6-0-octadecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl~-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-octa~
decanoyloxydodecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl~-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-octadecanoyloxydodecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-0-((3R)-3-octadecanoyloxydodecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-octa-decanoyloxydodecanoyl)-6-0-tetradecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-1-0-((3R)-3-octadecanoyloxydodecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl~-L-alanyl-D-isoglutamine methyl~ster N-[2-0-{2-Acetamido--2,3-dideoxy-6-0-octadecanoyl-1-0-((3R)-3-octadecanoyloxydodecanoyl)-a-D-gluco-d ~ ) pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isogiutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-octa-decanoyl.oxydodecanoyl)-1-thio-~-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester ~ -12-0 {2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-octadecanoyloxydodecanoyl)-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-((3R)-3-octadecanoyloxydodecanoyl)-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R~-3-octa-decanoyloxydodecanoyl)-6-0-tetradecanoyl-1-thio-B-~-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-1-S-((3R)-3-octadecanoyloxydodecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-didcoxy-6-0-octadccanoyl-1-S-(~3R)-3-octadecanoyloxydodecanoyl)-1-thio-~-D-gLucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine me thylester ~ 3 N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-i(3R)-3-eicosanoyloxydodecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido 2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-eicosanoyloxydodecanoyl)-a-D--glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-0-((3R)-3-~icosanoyloxydodecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D isoglutamine methyl.ester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-eicosanoyloxydodecanoyl)-6-0-tetradecanoyl-a-D gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-eicosanoyloxydodecanoyl)-6-0-hexadecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetam.ido-2,3-dideoxy-1-0-((3R)-3-eicosanoyloxydodecanoyl)-6-0-octadecanoyl~a-D-gluco-pyranos-3-yl}-D lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Ac~tamlAo-2,3-didcox~ S-((3R)-3-eicosanoyloxydodecanoyl)-l-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester ~ 3 N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-eicosanoyloxydodecanoyl)-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isogl~tamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-((3R)-3-eicosanoyloxydodecanoyl)-1-thio-B-D-gluco-pyranos-3-yl)-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-eicosanoyloxydodecanoyl)-6-0-tetradecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-eicosanoyloxydodecanoly)-6-0-hexadecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-(~3R)-3-eicosanoyloxydodecanoyl)-6-0-octadecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-didcoxy-1-0 ((31l)-3-docosanoyloxydodecanol)-a-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutarnine methylester N-[2-0-{2-Acetamido-2,3-dideoxy--6-0-decanoyl-2 ~ 7 ~3 -1-0-((3R)-3-docosanoyloxydodecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl~-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-docosanoyloxydodecanoyl)-6-0-dodeeanoyl-a-D-glueo-pyranos-3-yl3-D-lactoyl]-L-alanyl-D-isoglutamine-methylester N- [ 2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-docosanoyloxydodecanoyl)-6-0-tetradecanoyl-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-docosanoyloxydodeeanoyl)-6-0-hexadecanoyl-a-D-gluco-pyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N - [ 2-0-{2-Aeetamido-2,3-dideoxy-1-0-((3R)-3-docosanoyloxydodecanoyl)-6-0-oetadeeanoyl-a-D-glueo-pyranos-3-yl}-D laetoyl]-L-alanyl-D-isogluta~ine methylester N - [ 2-0-{2-Aeetamido-2,3-dideoxy-1-S-((3R)-3-doeosanoyloxydodeeanoyl)-1-thio-~-D-glueopyranos-3-yl}-D-laetoyl~-L-alanyl-D-.~soglutamine methylester N- [ 2-~-(2-Acetamido-2,3-dideoxy-6-0-deeanoyl-1-S-((3R)-3-docosanoyloxydodecanoyl)-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-~2-0~{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-docosanoyloxydodecanoyl)-6-0-dodecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl~D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-docosanoyloxydodecanoyl)-6-0-tetradecanoyl-1-thio-B-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N- E 2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-docosanoyloxydodecanoyl)-6-0-hexadecanoyl-1-thio-~-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-1-S-((3R)-3-docosanoyloxydodecanoyl)-6-0-octadecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-tetracosanoyloxydodecanoyl)-a-D-glucopyranos-3-yll-D-lactoylJ-L-alanyl-D-lsc)glutamine methyLester N-[2-0-{2-Acctarnido-2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-tetracosanoyloxydodecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester 2~ 3 N-[2-0-~2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-0-((3R)-3-tetracosanoyloxydodecanoyl)-a-D-~lucopyranos--3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R~-3-tetracosanoyloxydodecanoyl)-6--0-tetradecanoyl-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-1-0-((3R)-3-tetracosanoyloxydodecanoyl~-a-D-gluco-pyranos-3-yl3-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-~2-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-0-((3R)-3-tetracosanoyloxydodecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-did~oxy-1-S-((3R)-3-tetracosanoyloxydodecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methyles-ter N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-tetracosanoyloxydodecanoyl)-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl~-]:. alany:l D-isog~utan)lr methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-2~ 3 1-S-((3R)-3-tetracosanoyloxydodecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-~-alanyl-D-isoglutamine methylester N-~2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-tetracosanoyloxydodecanoyl)-6-0-tetradecanoyl-1-thio-~-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-1-S-((3R)-tetracosanoyloxydodecanoyl)-l-thio-B-D-gluco-pyranos-3-yl}-D-lactoyl.]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-S-((3R)-3-tetracosanoyloxydodecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-dodecanoyloxyhexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methyl.ester N-[2-0-{2-~cetamido-2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-dodecanoyloxyhexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine mcthylester N-[2-0-{2-Acetamiclo-2,3-dideoxy 6-0-clodecanoyl-1-0-((3R)-3-dodecanoyloxyhexadecanoyl)-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-(~3R)-3-2~Lil2~9 dodecanoyloxyhexadecanoyl)-6-0-tetradecanoyl-a-D-~luco-pyranos-3-yl}-D-lactoyl]-L-alarlyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-dodecanoyloxyhexadecanoyl)-6-0-hexadecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-t(3R)-3-dodecanoyloxyhexadecanoyl)-6-0-octadecanoyl-a-D-gluco~
pyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-1-S-((3R)-3-dodecanoyloxyhexadecanoyl)-1-thio-~-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoylutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-dodecanoyloxyhexadecanoyl)-1-thi.o-~-D-gluco-pyranos-3-yl~-D-lactoyl]-T,-alanyl-D-isoglutamine methylester N-~2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-((3R)-3-dodecanoyloxyhexadecanoyl)-1-th.io-~-D-gluco-pyranos-3-yl~-D-lactoyl]-l.-al.any:L-t)-:lsocJ:I.utaminc methylestcr N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-(~3R)-3-dodecanoyloxyhexadecanoyl)-6-0-tetradecanoyl-1-thio-~-2 ~

D-glucopyLanos-3-yl`~-D-lactoyl]-L.-alanyl-D-isoglutamine mcthylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-dodccanoyloxyhexadecanoyl)-6-0-hexadecanoyl-1-thio-~-D-gl-lcopyranos-3-yl}-D-lactoyl]-L-Alanyl-D-.isoglutamine methylester N-[2-0-f2-Ace-tamido-2,3-dideoY~y-1-S-((3R)-3-dodecanoyloxyhexadecanoyl)-6-0-octadecanoyl-1-thio-B-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-1-0-((3R)-3-tetradecanoyloxyhexadccanoyl)-a-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2 Acetamido-2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-tetradecanoyloxyhexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-i.soglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-0-((3R)-3-tetradecanoyloxyhexadecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine rnethylester N-[2-0-{2-Acetamido-2,3-did~oxy-6-0-t.~trad~carloyl-1-0-((3R)-3-tetradecanoyloxyhexad~carloyl)-a-D-gluco-pyranos-3-yl}-:D-lactoyl]-L-alanyl-D-isogllltamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-2 ~ 7 ~

1- n - ( ( 3R)-3-tetradecanoyloxyhexadecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-(2-Acetamido-2,3-dideoxy~6-0-octadecanoyl-1-0-((3R)-3-tetradecanoyloxyhexadecanoyl)-a-~-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isog].utamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-(~3R)-3-tetradecanoyloxyhexadecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-tetradecanoyloxyhexadecanoyl)-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-((3R)-3-tetradecanoyloxyhexadecanoyl)-1-thio-13-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-(2-Acetamido-2,3-dideoxy-6-0-tetradecanoyl-l-S-((3R)-tetradecanoyloxyhexadecanoyl)-1-thio-B-D-glucopyranos-3-yl}-'D-l.actoylJ-~ a'l.anyl-D-i,socJlul:alllirle methylestcr N-[2-0-~2-Acetarnido-2,3-dideoxy-6-0-hexadecanoyl-2~ J

l-.S-~(3R)-3-t~-~tradecanoyloxyhexadecanoyl)-1-thio-3-D-glucopyranos-3-yl~-D-lactoyl]-~-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-S-~(3R)-3-tetradecanoyloxyhexadecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl~-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-hexadecanoyloxyhexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-~2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-hexadecanoyloxyhexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6~0-dodecanoyl-1-0-((3R)-3-hexadecanoyloxyhexadecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-hexadecanoyloxyhexadecanoyl)-6-0-tetradecanoyl-a-D-glucopyranos-3~yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-[2-Acetamido-2,3-dideoxy-6-0-h~xadecanoyl-4~

2 ~ ~j l-O~ R) 3-hexadecarloyloxyhexadecanoyl~-a-D-gluco-pyranos-3-yl}-D-lactoyl)-L.-alanyl-D-isoglutamine methylester N-[~-O-~-Acetamido-2,3-dideoxy-1-0-((3R)-3-hexadecanoyloxyhexadecanoyl)-6-0-octadecanoyl-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-12-0-{2-Acetamldo-2,3-dideoxy-l-S-((3R)-3-hexadecarloyloxyhexadecanoyl)-1-thio-B-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-hexadecanoyloxyhexadecanoyl)-1-thio~13-D-glucopyranos-3-yl)-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-((3R)-3-hexadecanoyloxyhexadecanoyl)-1-thio-B-D-glucopyranos-3-yl}-D-]actoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-hexa-decanoyloxyhexadecanoyl)-6-0-tetradecanoy~ thio-r~-D-glucopyranos-3~yl}-D-lactoy~ -L-cl:Lallyl-l~-isoc3:Lutamin~
methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-1-S-((3R)-3-hexadecanoyloxyhexadecanoyl)-1-thio-13-D-2 1~ .5 glilcopyranos-3-yl}-D-lactoyl]-~-alanyl-D-isoylutamine rnethylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-hexa-decanoyloxyhexadecanoyl)-6 0-octadeeanoyl-1-thio-~-D-glucopyranos-3-yl~-D-lactoyl~-L-alanyl-D-isoglutamlne methylester N-[2-0-~2-Acetamido-2,3-dideoxy-1-0-((3R)-3-octa-deeanoyloxyhexadeeanoyl)-a-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy-6-0-decanoyl-1-0-(~3R)-3-oetadeeanoyloxyhexadeeanoyl)-a-D-glueopyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy~6-0-dodeeanoyl-1-0-((3R)-3-oetadeeanoyloxyhexadeeanoyl)-a-D-glueo-pyranos-3-yl}-D-laetoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-1-0-((3R)-3-octa-decanoyloxyhexadecanoyl)-6-0-tetradecanoyl-a-D-glueo-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isog:Lutamine methylester N-[2-0-{2-Aeetamido-2,3-d.ideoxy-6-0-hexad~eanoyl-1-0-((3R)-3-oetadeearloyloxyh~xadeeatloyL)-a-D-glueo-pyranos-3-yl}-D-laetoyll-L-alanyl-D-isoylutamine methylester 2 ~ 2 ~ .~

N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-0-((3R)-3-octadecanoyloxyhexadecanoyl)-a-D-gluco-pyranos-3-yl.~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-octa-decanoyloxyhexadecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-octadecanoyloxyhexadecanoyl)-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-((3R)-3-octadecanoyloxyhexadecanoyl)-1-thio~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-~-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-octa-decanoyloxyhexadecanoyl)-6-0-te-tradecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-~2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-l-S-((3R)-3-octadecanoyloxyhexadecanoyl)-1--th:i.o-~
glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-.isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-octaflecanoyl-l-S-((3R)-3-octadecanoyloxyhexadecanoyl)-1-thio-~-D-2 ~

glucop~ranos-3-yl~-D-lactoyl~-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-1-0-(~3R)-3-eicosanoyloxyhexadecanoyl)-a-D-glucopyranos-3-yl}-D-lacto-yl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-eicosanoyloxyhexadecanoyl-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-0-((3R)-3-eicosanoyloxyhexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D isoglutamine methylester N- E 2 -o- { 2-Acetamido-2,3-dideoxy-1-0-((3R)-3-eicosanoyloxyhexadecanoyl)-6-0-tetradecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-1-0-((3R)-3-eicosanoyloxyhexadecanoyl)-6-0-hexadecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3--dideoxy-1-0-((3R)-3-eicosanoyloxyhexadecanoyl)-6-0-octad~cano~l-a-~-g:Luco-pyranos-3-yl.}-D-lactoyl]-L-alarlyL-D-i.sog:Lutam:i.ne methylester 2~ ~27.`3 N-~2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-eicosanoyloxy~exadecanoyl)-1 thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-eicosanoyloxyhexadecanoyl) 1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-S-((3R)-3-eicosanoyloxyhexadecanoyl)-1-thio-~-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-eicosanoyloxyhexadecanoyl)-6-0-tetradecanoyl-1-thio-~-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2~Acetamido-2,3-dideoxy-1-5-((3R)-3-eicosanoyloxyhexadecanoyl)-6-0-hexadecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-(~3~)-3-eicosanoyloxyhexadecanoyl)-6-0-octadccanoyl-1-thio-~-D-gl.ucopyranos-3-yl~-D-lactoy~ -L-alanyl-l)-isoglutamine methyl.ester 20~ 27~3 N-[2-0-~2-AcetamidQ-2,3-dideoxy-1-0-((3R)-3-docosanoyloxyhexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-~2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-0-~(3R)-3-docosanoyloxyhexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-docosanoyloxyhexadecanoyl)-6-0-dodecanoyl-a-D-gluco-pyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-docosanoyloxyhexadecanoyl)-6-0-tetradecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-docosanoyloxyhexadecanoyl)-6-0-hexadecanoyl-a-D-gluco-pyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-docosanoyloxyhexadecanoyl)-6-0-octadecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-iso~lutamine methylester N-[2-0-{2-Acetamido-2,3-d:i.deoxy-1-S-((3~)-3-docosanoyloxyhexadecanoyl)-l-thio-B-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester 2 ~ 7 e.3 N-[2-0-~2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-docosanoyloxyhexadecanoyl)-1--thio-B-D-gluco-pyranos-3-yl}-D-lactoy]]-L-alanyl-D-isoglutamine rnethyles~er N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-docosanoyloxyhexadecanoyl)-6-0-~odecanoyl-l~thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-docosanoyloxyhexadecanoyl)-6-0-tetradecanoyl-1-thio-B-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy-1-S-((3R)-3-docosanoyloxyhexadeeanoyl)-6-0-hexadecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Aeetamido-2,3-dideoxy-1-S-((3R)-3-docosanoyloxyhexadeeanoyl)-6-0-octadecanoyl-1-thio-~-D-glueopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetami..do-2,3-dideoxy~1-0-((3R)-3-t~tra-cosanoyloxyhexadecanoyl)-a-D-ylucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester 2 ~ 2 rl ~

N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-tetracosanoyloxyhexadecanoyl)-a-D glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-~2-Acetamido-2,3-dideoxy-6-0-dodecanoyl-1-0-((3R)-3-tetracosanoyloxyhexadecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-tetra-cosanoyloxyhexadecanoyl)-6-0-tetradecanoyl-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-(2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-1-0-~(3R)-3-tetracosanoyloxyhexadecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-0-((3R)-3-tetracosanoyloxyhexadecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-tetra-cosanoyloxyhexadccanoyl)-1.-thio-~-J)-c):Lucopyranos-3-y:l}-D-lactoyl]-L-alany:l-D-isot~:Lutamine mettlylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-tetracosanoyloxyhexadecanoyl)-1-thio-~-D-gluco-2 7 ;~3 pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-12-Ace-tamido-2,3-dideoxy-6-0-dodecanoyl-1-S-((3R)-3-tetracosanoyloxyhexadecanoyl)-1-thio-B-D-glucopyranos-3-yl)-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Ace-tamido-2,3-dideoxy-1-S-~(3R)-3-tetra-cosanoyloxyhexadecanoyl)-6-0-tetradecanoyl-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-hexadecanoyl-1-S-((3R)-3-tetracosanoyloxyhexadecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester and N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-S-((3R)-3-tetracosanoyloxyhexadecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester.
The compounds of the present invention can be basically prepared by the following process.

2 ~ 2 7 ~3 /
C ~- o / \ ~ O ~ H,X acylation >
CH3 /~1 ~ ~

CO
Ala isoGln-OCH3 (II) \ /

C ~ - - ~ H,R1 deacetonation CH3 O / ~

CO
Ala-isoGln-OCH3 (III) 2~ ~27~) HO~ R201 / ~ o acylation , ~ O

HO~_~H ~ Rl H~H ~ R
CH3C~NHCOCH3 CH CH NHCOCH

CO CO
Ala-isoGln-OCH3 Ala-i.soGln-OCH3 (I') (I) In the formulae, X is OH or SH; Rl and R2 are defined as above.

The above mentioned process consists of two acylation steps (the acylationsat 6th and 1st positions of the glucopyranose moiety3 and one deacetonation step.
The two acylation steps can be conducted by reacting a compound of the formula (II) or ~I') with a specific acylating agent (R2H, R3H or its reactive derivative). These steps are ~encrally carliod out in an anhydrous organic solvent (Eor example, 2 ~ 7 ~

dimethylformamide or dioxane) and at room temperature or a slightly elevated temperature. When R2H or R3H ~a free acid) is used, it is conducted in the presence of an appropriate condensing agent (for example, dicyclo-hexylcarbodiimide, N-cyclohexyl-N'-morpholinoethyl-carbodiimide, N-cyclohexyl-N'-~4-diethylaminocyclo-hexyl)-carbodiimide or N,N'-diethylcarbodiimide).
Examples of reactive derivatives of R2H or R3H are conventional reactive derivatives used in acylation, such as mixed acid anhydrides, active esters, acid halides and the like. The deacetonating step can be readily conducted under an acid hydrolysis condition ~e.g., using 80~. acetic acid aqueous solution~ at a slightly elevated temperature.
The compounds of the formula (II) are known or can be readily prepared by known methods.
The compounds obtained by the above process may be purified by a conventional method such as a column chromatography using almina or silica gel, recrystallization and the like.
The compounds of thc formula (I) oE the present invention have an action for enhancing function of cells relevant to in vivo immune response and an action for increasing the number of said cells, and hence they 2 ~ i ~ 2 7 3 are useful as an immunor~gulating agent. The immunoregulating agent of the present invention can be used to enhance in vivo activities of vaccines such as ~CG vaccine, hepatitis vaccine, influenza virus vaccine or the like, various antibacterial agents or anti-tumor agents.
The immunoregula~ing composition of the present invention comprises a compound of the formula (I) and a pharmaceutically acceptable carrier. The composition may be any dosage form for oral and parenteral administrations.
The compositions for oral administration are generally dosage forms such AS powders, tablets, emulsions,capsules, granules and liquid prepartions (including liquid extracts, syrups and the like).
Examples of carriers for powders or other orally administrable solid preparations include lactose, starch, dextrin, calcium phosphate, calcium carbonate, synthetic or natural aluminium silicate, magnesium oxide, dried aluminium hydroxide, magnesium stearate, sodium bicarbonate, dried yeast and the li~, and ~hose for liquid preparations ;incllldc water, glycexine, propylene glycol, simple syrup, ethanoL, fatty oil, ethylene glycol, polyethylene glycol, sorbitol and the like. A typical example of the composition for 2 ~ 2 7 3 parenteral administratioll ls an injection. Liquid carriers for the injection include sterile distilled water. When a compound of the formul.a (I) is less soluble in water, an appropriate solubilizer is used.
Each of the above preparations can be prepared by conventional methods.
When the compounds of the formula (II) of the present invention are used for enhancement of antitumor agents, they may be orally or parenterally administered to an adult human in an amount of 150 to 250~g/day in one dose. When used for enhancement of vaccines, they may be administered to an adult human in an amount of 0.5 to 2.Omg/1 to 2 weeks in one dose. For treatment of hepatitis, they may be orally or parenterally admini.stered to an adult human 1 to 3 tirnes for 3 months in an arnount of 0.5 to 2.Omg in one dose. For enhancement of antibacterial agents, they may be used to an adult hurnan in an amount 20 to lOO~g/day in one dose.
The immunoregulating agents of the present invention may be generall~ uscd by Eormulat.i.ng thcmselves only as dcscr:i.bed abovo. BUt tlley may be formul.ated togct.ller wlt.l-~ an agent ~.o be ellhanced its action .

2 ~ 7 ~

Further, the immunoregulating agents of the ~resent invention can be used for not only humans but also other mammals such as pigs, bovines, sheeps, dogs, and cats.
The present invention is illustrated with following examples.
Example 1 N-[2-0-{2-Acetamido-2,3-dideoxY-1-0-(2-tetra-decYlhex_decanoyl)-a-D-~lucopy~a~nos-3-yl}-D-lactoy~l-L
-alanyl-D-isoqlutamine methYlester The compound of the formula ~III) wherein R1 is 2-tetradecylhexadecanoyloxy group (279.4mg, 0.281mmol) was dissolved in 80% acetic acid aqueous solution ~8ml) and the resultant was allowed to stand for 2 hours at 45C. After confirming the completion of the reaction with T.L.C.~CH2Cl2 : MeOH = 10 : 1), the resultant was concentrated under reduced pressure to obtain quantitatively the title compound ~266.2mg).
mp : 147.0-148.0C
[a]D5: +44.38~c=1.050, CH2Cl : MeOH=1 : 1) IR ~max~KBr)cm 1 : 3350, 2930, 2350, 17~10, 1650, 1520 NMR~CD3OD-CHCl3)~ppm) : 0.88(t,6H,J=6.6Hz), 1.26(s,48H), 1.38-1.43(m,6H), 2 01 ~ 2 r~ ~

1.51-1.62(m,4H), l.93(s,3H), 3.70(s,3H), 6.16(d,lH,J=4.OHz) Example 2 N-{2-0-~2-Acetamido-2,3-dideo_y-1-S-(2-tetra-decYlhexadecanoyl)-1-thio-~-D-qlucopyranos-3-yl]-D-lactoyl}-L-alanyl D-isoqlutamine methylester The compound of the formula (TII) wherein R1 is 2-tetradecylhexadecanoylthio group (133.7mg) was dissolved in 80% ace'cic acid aqueous solution (15ml), wllich was allowed to react for 2 hours at 45C. After confirming the completion of the reaction with T.L.C., the resultant was concentrated under reduced pressure and crystallizecl from ether to obtain quantitatively the title compound (127.Omg, crystals).
mp : 130.0-131.0C
~a~D5: +46.79(c=1,201, CH2Cl2 : MeOH=1 : 1) IRy max(KBr)cm 1 : 3300, 2920, 2850, 1720, 1630, 1530 Example 3 N-[2-0-~2-Acctam~do-2,3-dideoxy-1-0-t(3R)-3-2 ~ ~L 1 2 r7 ~J

tetradecanoyloxvtetradecanoyl)-a-D-qlucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester The compound of the formula (III) wherein R1 is 3-tetradecanoyloxytetradecanoyloxy group (409.lmg, 0.411mmol) was dissolved in 80% acetic acid aqueous solution (15ml) and allowed to stand for an hour at 45C. In the same manner as that in Example 1, the title compound was quantitatively obtained (386.9mg).
mp : 133.8-134.6DC
[a]D5: +44.74 (c=1.180, CHCl3 : MeOH=1 : 1) IR Ymax(RBr)cm 1 : 3700-3140, 2930, 2850, 1740, 1250, 1630, 1540 NMR(CDCl3)~ : 0.89t-t,6H,J=2.2Hz), 1.27(m,36H), 1.43(rn,6H), 1.60(m,4H), 2.00(s,3H), 2.10-2.30(m,4H), 2.44-2.67(m,6H), 3.68(s,3H), 5.31(m,1H), 6.05(d,1H) 2 ~ 7.3 Example 4 N-(2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-tetradecanoyloxytetradecanoyl)~ hio~-D-qluco-pyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoqlutamine methYl_ester The compound of the ~ormula (III) wherein Rl is 3-tetradecanoyloxytetradecanoylthio group (580.lmg, 0.5808mmol) was dissolved in 80% acetic acid aqueous solution (12ml) and allowed to stand for an hour at 45C. After confirming the completion of the raction with T.L.C. (CH2Cl2: MeOH=10 : 1), the resultant was concentrated under reduced pressure. The resulting syrup was lyophilized to obtain quantitatively the title compound (555.2mg, crystals).
mp : 110-111C
~a]D5: +26.68(c=0.787, CH2Cl2 : MeOH=2 : 1) IR ~max(KBr)cm 1 : 3650-3130, 3300, 2940, 2860, 1740, 1650, 1550, NMR(CDC13-CD3OD)~ : 0.88 (t,6H,J=6.6Hz), 1.25 (m,36H), 1.35 (d,3H,J-7.0Hz), 1.39 (d,3H,J~7.J~lz), 1.43-1.58 (m,4H), 1.93(s,3H), 1.93-2.04 (rn,2H), 2.09-2.87(m,6H), 3.71(s,3H), 4.05(t,1H,J=

2~127.~

10.4Hz), 4.28-4.~3(m,1H), 4.31(~,1H,J=7.0Hæ), 4.38-4.43 (o,lH), 5.12~d,1H,J=ll.OHz) 5.17-5.26(m,lM) Example 5 l~-[2-0-~2-Acetamido-2,3-dideoxy-6-0-decanoYl-l-O-(2-tetradecylhexadecanovl)-a-D-~lucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester The compound of the formula (I) wherein R1 is 2-tetradecylhexadecanoyloxy group (143.3my, 0.150mmol) was dissolved in a mixture of dry dioxane (1.3ml) and dry N,N-dime-thylformamide IDMF, 1.3ml). To the solution were added decanoic acid (29.6mg, 0.180mmol), dicyclohexylcarbodiimide (DCC, 61.7mg, 0.300mmol~ and dimethylaminopyridine (DMAP, 9.1mg, 0.075mmol), and the resultant was stirred for 14 hours at room temperature.
After the compLetion of the reaction, -the reaction rnixture was concentrated under reduced pressure. The resulting syrup was subjected to i a column chromatography [Wakogel~ C-200 eluted with CH2Cl2/MeOH
((a) 150 : 1 and (b) 20 : 1)l and t.l-~o OLurlt.e ol.ut-oct with the eluerlt: (b) was concentrated undcL reduced pressure. The resultant syrup was subjected to a column chromatography [active alumina 90 eluted with 2~3~7 CH2C12/l~eOH ((a') 150 : i and (b') 20 : 1)], to remove DMAP and the eluate eluted with the eluent (b') gave the title compound (121.3mg, yield: 72.6%).
mp : 116.3-117.0~C
[a]D : +42.S6(C=0.726, CHCl3 : MeOH-2 : 1) IR ymax(XBr)cm 1 : 3650-3150, 2940, 2870, l740, 1650, 1540 NMR(CDCl3)o : 0.88(t,6H,J=6.8Hz), 0.92(t,3H,J=7.1Hz), 1.25(ml62~l), 1.39(d,3H,J=6.6Hz), 1.41(d,3H,J=6.6Hæ), l.51-1.60(m,6H), 1.90-2.23(m,2H), ~.9~(s,3~1~, 2.33(t,2~-l,J-7.5~z), 2.39-2.50(m,3H), 3.69(s,3H), 6.18(d,1H,J=3.7Hz) Example 6 N-[2-0-~2-Acetamido-2,3-d eoxy-6-0-tetra-decanoYL-l-o-(2-t-tradecylhexadecanovl)-a-D-g Pyranos-3-Yl}-D-lactoyl]-L-alanyl-D-iso~lutalrl.ine methY Lestel Thc compound of thc ormu.Lel (:C') where.in Rl is 2-tetradecylhexadecanoyloxy group (:L39.7mg, 0.1~7mmol) is dissolved in a mixture of dry dioxanc (2ml) and dry DMF (2ml). To the solution were added tetradecanoic ~ Q~ ~ ) acid (40.0mg, 0.176~mol), DCC(60.2mg, 0.2.94mmol) and DMAP(8.9mg, 0.074mmol). The resultant was stirred for 12 hours at room temperature and then treated in the same manner as that in Example 5 to obtain the title compound (105.4mg, yield: 61.7%).
mp : 116.8-117.7~C
[a]2D5: ~29.22~(C=1-054, CH2C12) IR Ymax(KBr)cm 1 : 3700-3100, 2940, 2860, 1740, 1660, 1540 NMR(CDCl3)~ : 0.88(t,9H,J=6.4Hz), 1.25(m,7H), 1.38(d,3H, J--6.6Hz), 1.41(d,3H, J=7.3Hz), .49-1.60(m,6H), 1.93(s,3H), 2.03-2.21(m,2~1), 2.32(t,2H,J=7.7Hz), 7.38-2.74(m,3H), 3.68(s,3H), 6.17(d,1H,J=3.7Hz) EsamPle 7 N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-0-(2-tetradecylhexadecanoyl)-~-D-~ copyrano~
D-lactoyl]-L-alanyl-D-iso~Llutamine methyL_ster ___~__ The compound o~ the Eormula (I') wherein R1 is 2-tetradecylhexadecanoyloxy group (122.7mg, 0.129mmol) was dissolved in a mixture of dry dioxane (1.5ml) and 2 ~ 3 dly DMF(0.5ml). To the solution were added octadecanoic acid ~44.5mg, 0.155mmol), DCC(53.7mg, 0.258mmol) and DMAP(7.9mg, 0.065mmol). The resultant was stirred fol- 14 hours and then treated in the same manner as that in Example 5 to obtain the title compound(ll9.Omg, yield: 75.6%).
mp : 118.7~120.0~C
[a]D5: ~39.45(c=0.621, CHCl3 : MeOH=2 : 1) IR ~max(KBr)cm : 3650-3150, 2930, 2860, 1740, 1650, 1540 NMR(CDCl3)~ : 0.88tt,9H,J=6.6Hz), 1.25(m,78H), 1.39~d,3H,J=6.6Hz), 1.41(d,3H,J=6.6Hz), 1.49-1.60(m,6H), 1.94(s,3H), 1.90-2.26(m,2H), 2.32(t,2H,J=7.3Hz), 2.39-2.50(m,3H), 3.69(s,3H), 6.18(d,1H,J=3.7Hz) Example 8 N-[2-0-{2-Acetasnido-2,3-dideoxy~6-0-deca ~
S-(2-tetradecylhexad~canoyl~ 1-thio-~-D-~luc~eyra s 3--yl}-D-lactoylJ-L-alanyl-D-isoqlutamlne methylester The compound of the formula (I') wherein R1 is 2-tetradecylhexadecanoylthio (128.4mg, 0.134mmol) was 2 ~

dissolvcd in a mlxtule of dry dioxane (1.5ml~ and dry DM~` (l.Oml). To the solution were added decanoic acid (27.4mg, 0.161mmol), DCC(54.6mg, 0.268mmol) and DMAP(8.]mg, 0.067mmol!. The resultant was stirred for 6.5 hours at room temperature. After confirming the completion oE the reaciton with T.L.C. (10 : 1), the resultant was lyophilized and subjected to a column chromatography [Wakogel~ C-200 eluted with CH2Cl2/MeOH
((a) 150 : 1 and (b) 50 : 1)]. The eluate eluted with the eluent (b) gave the title compound (99.6mg, yield:
66.8%).
mp : 98.6-99.4DC
~a]2D5: ~17.69(c=0.797, CH2C12: MeOH=2 : 1) IE~ ~max(~Br)cm : 3500-3200, 2950, 2880, 1750, 1640, 1560 NMR(CDC13-CD30D)~ : 0.88(t,6H,J=6.6Hz), 0.92(t,3H,J=7.lHz), 1.25(m,56H), 1.34(d,3H,J=6.6Hz), 1.40(d,3H,J=7.0Hz), ].58-1.71(m,6H), l.90(s,3~1), 1..9~-2.2 2~33(t~2H~J~ 5Hæ)~
2.42-2.52(m,3H), 3.69(s,3H), 5.11(d/lE-l,J=10.6Hz) 2~ 3 Example 9 N-[2-0 {2-Acetamido-2,3-dideoxy-6-0-tetra-decanoyl-l-S-(2-tetradcylhexadecanoyl)-1-thio-~-D-glucopyranos-3-yl~-D-lactoyl]-L-alanyl-D-isoglutamine methYlester The compound of the formula (I') wherein Rl is 2-tetradecylhexadecanoylthio group (125.0mg, 0.131mmol) was dissolved in a mixture of dry dioxane ~1.5ml) and dry DMF (l.Oml). To the solution were added tetradecanoic acid (35.3mg, 0.157mmol), DCC(53.lmg, 0.262mmol) and DMAP (7.9mg, 0.066mmol). The resultant was stirred for 3 hours at room temperature and then treated in the same manner as that in Example 8 to obtain the title compound (125.8mg, yield: 82.5~).
mp : 99.0-100.4C
[a]D : +2.13(c=2.16, CH2C12) IX ~max(KBr)cm 1 : 3650-3200, 2930, 2860, 17~0, 1650, 1550 NMR(CDC13)~ : 0.85-0.95(m,9H), 1.25(m,68H), 1.36(d,3H,J=6.6Hz), 1.41(d,3H,J=7.3Hz), 1.47-1.76(m,6ll), l.83-2.32 (m~ 2H) 1.94(s,311), 2.35(t,2il,J=7.9~1z), 2.47-2.53(m,3H), 3.70(s,3H), 5.12(d,1H,J=10.3Hz) 20~27~

Example 10 N-[2-0-{2-Acetamido-2,3-dideoxy-6-O-octadecanoy l-S-(2-tetradecylhexadecanoy~ -thio-~-D-qlucopyran 3-y~}-D-lactoyl]-L-alanYl-D-isoglutamine methylester The compound of the formula (I') wherein Rl is 2-tetradecylhexadecanoylthio (122.4mg, 0.128mmol) was dissolved in a mixture of dry dioxane (1.5ml) and dry DMF (l.Oml). To the solution were added octadecanoic acid (43.Omg, 0.145mmol), DCC(52.Omg, 0.245mmol) and DMAP (7~7mg, 0.064mmol). The resultant was stirred for 4 hours at room temperature and treated in the same manner as that in Example 8 to obtain the title compound (102.7mg, yield : 65.6%).
mp : 99.3-101.0C
~a]D5: +2.06D (c=0.376, CH2Cl2 : MeOH=2 : 1) IR ~max(KBr)cm 1 : 3600-3150, 2920, 2840, 1740, 1640, 1540 NMR(CDCl3-CD30D)~ : 0.88(t,9H,J=6.6Hz), 1.26(m,76H), 1.35(d,3H,J=6.6Hz), 1.40(d,3H,J=7.3Hz), 1.S~-1.61(m,6H), 1.88(s,3H), 1.92-2.26(m,2~1), 2.33(t,2H,J=7.7Hz), 2.41-2.55(m,3H), 3.69(s,3H), 2~ ~27c?

4.40(q,lH), 5.10(d,1H,J=ll.OHz) Example 11 N-~2-0-{2-Acetamido-2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-tetradecanoyloxytetradecanoyl)-a-D-qluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoc31utamine methylester The compound of the formula (I') wherein R1 is 3-tetradecanoyloxytetradecanoyloxy group (116.9mg, 0.121mmol) was dissolved in a mixture of dioxane (1.5ml) and dry DMF (0.5ml). To the solution were added decanoic acid (24.3mg, 0.145mmol), DCC (48.4mg, 0.242mmol) and DMAP (7.2mg, 0.161mmol). The resultant was stirred for 8 hours at room temeperature. After confirming, the completion of the reaction wlth T.L.C.
(CH2Cl2: MeOH=10 : 1), the resultant was concentrated under reduced pressure. The resulting syrup was subjected to a column chromatography [Wakogel~ C-200 eluted with CH2Cl2/MeOH ((a) 150 : 1 and (b) 35 : 1)].
I`he eluate eluted with thc ~lucnt (b) gav~ th~ title compound (80.4mcJ, yieJ.d : 59.6~,).
mp : 72.0-72.8C
[a]25 : +27.86(c=0.804, CH2Cl2) IR ~max¦Film)crn : 3700-3100, 2930, 2850, 2~2'~ 3 1740, 1650, 1540 NMR(CDCl3)~ : 0.88(t,9H,J=6.6Hz), l.25-1.27(m,48H), 1.43(d,3H, J=6.6Hz), l.45(d,3H,J=7.0Hz~, 1.61(m,6H), 2.00(s,3H), 2.04-2.24(m,2H), 2.30(t,2H, J=7.5Hz), 2.32-2.67(m,6H), 3.69(s,3H), 4.21(q,1H,J=6.6Hz), 5.29(m,1H), 6.05(d,1H,J=3~3Hz) Example 12 N-[2-0-{2-Acetamido- ~ tetradecanoyl-1-0-((3R)-3-tetradec~ y___ytetradecanoyl)-a-D
pyranos-3-yl}-D-lactoYl]-L-alanyl-D-i.soglutamine methylester The compourld of the formula (I') wherein R1 is 3-tetradecanoyloxytetradecanoyloxy (108.6mg, 0.~15mmol) was dissolved in a mixture of dry dioxane (1.5ml) and dry DMF (0.5ml). To the solution were added tetradecanoic acid (30.]mg, 0.137mmol), DCC(45.3mg, 0.228n~ol) and DMAP (6.7lng, 0.057mmol.). The mixture was allowed to react Eor 14 hours at room temperature.
The resultant was treated in the same manner as that in 2 ~ 7 .~

Example 11 to obtain the title compound (99.lmg, yield:
7~i.6~).
mp : 72.5-73.6C
[~]2~5: +26.51(c=1.38~,C~l2C12) IR ~max(film)cm 1 : 3700-3150, 2930, 2850, 1740, 1660, 1540 NMR(CDC13~ : 0.88(t,9H,J=6.6Hz), 1.25-1.38(m,56H), 1.43(d,3H,J=6.6Hz), 1.45(d,3H,J=7.0Hz), 1.60(m,6H), l.99(s,3H), 2.06-2.24(m,2H), 2.30(t,2H,J=7.5Hz), 2.32-2.66(m,6H), 3.69(s,3H), 4.21(q,1H,J=7.0Hz), 5.30(m,1H), 6.05(d,1H,J=3.3Hz) Example_13 N-[2-0-{2-Acetamido-2l3-dideoxy-6-0-octadecanoyl-1-0-((3R)-3-tetradecanoyloxytetradecanoyl)-a-D-qluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester The compound of the formula (I') wherein Rl is 3-tetradecanoyloxytetradecanoyl group (108.8mg, 0.114mmol) was dissolved i.n a mixture oE d]Ay dioxane (1.5ml) and dry DMF (0.5ml). To the solution were 7 ~

added octadecanoic acid (37.6mg, 0.137mmol). DCC
(45.4mg, 0.228mmol) and DMAP (6.7mg, 0.057mmol~. The resultant was stirred for 14 hours at room temperature and then treated in the same manner as that in Example 11 to obtain the title compound (95.6mg, yield: 63.5~).
mp : 68.1-69.0C
[a]25: +26.15(c=1-333, CH2Cl2) IR Ymax(film)cm 1 : 3700-3150, 2930, 2850, 1740, 1650, 1540 NMR(CDCl3)~ : 0.88(t,9H,J=6.6Hz), 1.25-1.39(m,64H), 1.43(d,3H,J=6.6Hz), 1.44(d,3H,J=7.0Hz), 1.58-1.60(m,6H), l.99(s,3H), 2.02-2.22(m,2H), 2.30(t,2H,J=7.5Hz), 2.32-2.67(m,6H), 3.69(s,3H), 4.21(~,1H,J=6.6Hz), 5.30(m,1H), 6.05(d,1H,J=3.3Hz) RxamPle 14 N-[2-0-~2-Acetamido-2,3-dideoxy-6-0-decanoyl-L-S-((3R)-R-tetradecanoyloxy__tradccclnoy~ -th:io ~-D-y~ ala~l D-isoglutamine ethylester 2 ~ ~ ~ 2 ~ ~3 T he compound of the formula ~I) wherein R~ is 3-tetradecanoyloxytetradecanoylthio (239.2mg, 0.250mmol) was dissolved in a mixture of dry dioxane (0.5ml) and dry DMF (0.5ml). To the solution were added decanoic acid (51.6ml, 0.300mmol), DCC (102.9mg, 0.50mmol) and DMAP (15.2mg, 0.499mmol), and the resultant was stirred for 2 hours at room temperature.
After confirming the completion of the reaction with T.L.C. (CH2C12: MeOH=10 : 1), DC urea of a reaction by-product was filtered off and washed with dioxane.
The filtrate and washings were combined and then lyophilized. The amorphous material thus obtained was subjected to a column chromatography [Wakogel~ C-200 eluted with CH2C12/MeOH ((a) 200 : 1, (b) 70 : 1, (c) 60 : 1 and (d) 40 : 1)]. The eluate eluted with the eluent (c) gave the title compound (111.6mg, yield:
40.2%).
mp : 138.6 - 139.9DC
la ~ : +17.09 (c=0.702, CH2C12:MeOH = 2:1) IR~max(film)cm 1 : 3650-3020, 3250, 2930, 2850, 1740, 1660, 1540 NMR(CDC13)fi: 0.87(t,91l,.J=5.7Hz), 1.25(m,52H), 1.39(d,3H,J=6.6Hz), 1.58(m,6H), 1.95(s,3H), 2.10-2.28(m,2H), 2.34(6,2H r J=7.7Hz), ,.J

','.~'7-2.91(1n,6H), 3.6g(~,3H), 5 13(d,l}l,J=11.0Hz), 5.]1-5.21(m,1H) xample 15 N-[2-0 {2-Acetamido-2~3-dideoxY-6-o-tetradecan ~-S-((3R)-3-tetradecanoyloxytetradecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyI-D-isoglutamine methylester The compound of the formula (I') wherein R1 is 3-tetradecanoyloxytetradecanoylthio (206.5mg, 0.215 mmol) was dissolved in dry dioxane (0.5ml) and dry DMF
(0.5ml). To the solution were added tetradecanoic acid (59.Omg, 0.259 mmol), DCC (88.9mg, 0.431 mmol) and DMAP
(13.1mg, 9.1077 mmo]). The resultant was stirred for 2.5 hours at room temperature and then treated in the same manner as that in Example 14 to obtain the title compound (95.6mg, yield: 38.0%).
mp : 136.1 - ~37.7C
[a ~ : -tl7.57(c=0.956, CH2Cl2:MeOH = 2:1) IR rmax (film)cm : 3650-3120, 3300, 2930, 2El60, 17~n, ~i40, l5~0 NMR(CDCl3)~: ().8El(t,9EI,J=6.6~lz), l.25(m,56}1), 1.39(d,3~1,J-7.0Hz), 1.42(d,3~1,J=7.0Hz), :l.57(m,6H), 2~l27~3 l.97(s,3~), 2.01-2.28(m,2H) t 2.34(t,2H,J=7.7Hz), 3.71(s,3H), 5.~3(d,lH,J=ll.OHz), 5.11-5.23(m,1H) Rxample 16 N-[2-0-~2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-]-S-((3R~-3-tetradecanoyloxytetradecanoyl)-1-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-iso~lutamine methylester The compound of the formula (I') wherein R1 is 3-tetradecanoyloxytetradecanoylthio (203.2mg, 0.212 mmol) was dissolved in a mixture of dry dioxane (0.5ml) and dry DMF (0.5ml). To the solu-tion were added octa-decanoic acid (63.1mg, 0.254 mmol), DCC (87.5mg, 0.424 mmol) and DMAP (12.9mg, 0.106 mmol). The resultant was stirred for 3 hours at room temperature and then treated in the same manner as that in Example 14 to obtain the title compound (112.2mg, yield: 43.2%).
mp : 133.7 - 134.5C
[a]2D5: +17.46 (c=1.122, CH2Cl2:MeOH = 2:1) IR yma~(film)cm : 3700-3150, 3320, 2960, 2900, ~750, ~.~80, ~580 NMR(CDCl3)~: 0.87(6,9H,J=5.5Hz), 1.25~m,6.6H), 1.39(d,311,J=5.9Hz), 1.57(m,6H), 1.95(s,3H), 1.95-2.18~m,2H), 8~

2 ~ 7 2.25-2.9n~m,6H), ?.38(t,2H,J=7.1Hz), 3.69(s,3H), 5.~3(d,1~1,J=ll.O~z), 5.11-5.20(m,1H) Example 17 _l2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-hexa-decanoyloxytetradecanoyl)-a-D-~lucopyranos-3-Yl} D-lactoyl]----alanyl-D-isoglutamine methylester The compound of the formula (III) wherein R1 is 3-hexadecanoyloxytetradecanoyloxy (408.lmg, 0.410 mmol) was dissolved in 80% acetic acid aqueous solution (15ml), which was allowed to stand for 1.5 hours at 45'~C. In the same manner as that in Example 4, the title compound (391.7mg) was quantitatively obtained from the above solution.
m.p. : 134.2 - 135.5C
[a]D5: +47.38 (c=0.878, CH2Cl2:MeOH = 1:1) IR ~max ~cm) 1 : 3700-3100(0H), 3300(NH) 29~0, 2850(C~I) J740(ester) 1650, 1530(amido) NMR(CDCl3)~ : 0.88(t,9H,JMeCH26llz,3MeCH2), 1.25(m,40H,20CHz), 1.-12(d,3H,J~IecH7.3Hz,MeC of Ala), 1 2 7 ~3 1.45(d,3H,JMecll7.3Hz,HeC of Lac), l.57-].60(m,6~1,3MeCh~), 1.95-2.17(m,2H,CH2CH of G]n), 2.00(S,3H,AcN), 2.30(t,2H,JC112CH27.5Hz,CH2CO of Gln), 2.37-2.66(m,6H,3CH~CO), 3.68(S,3~1,COOMe), s.30-5.42(m,1H,~-3 of C17--C16)' 6.03(d,1H,J1 2,3.3HZ,H-l), xample 18 N-l2-0-~2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-1-0-(~3R)-3-hexadecanoYloxytetradecanoyl)-a-D-~luco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D~isoglutamine methylester The compound of the formula (I') wherein R1 is 3-hexadecanoyloxytetradecanoyloxy (l91.lmg, 0.200mmol) was dissolved in a mixture of dry dioxane (3.Oml) and dry DMF (1.0ml). To the solution were added octadecanoic acid (74.Omg, 0.260mmol), DDC(82.5mg, 0.400mmol) and DMAP (12.2mg, 0.100mmol). Thc resu1tant was stirred for 16 hours at room tcmpcLature. In the same manner as that in F.xample 11, the title compound (193.1mg, yield : 78.9%) was obtained.

2 0 ~ ~ 2 ~) r3 mp : 69.5-71.0C
[~]2~5: -~0.69(C=1.504, CH2C12 : MeOH=2 : 1) IR ymax(cm ) : 3700-313010H), 3300(NH), 2930, 2860(C~I), 1740(ester), 1660, 15~0(amido), NMR(CDC13~ : 0.38(t,9H,JMeCH26.6Hz,3MeCH2), 1.25(m,68H,34CH~), 1.~3(d,3H,JMeCH5.9Hz,MeC of Ala), 1.45(d,3H,JMeCH5.9Hz,MeC oE Lac), l.60(m,6H,3MeCH2), l.99(s,3H,AcN), 2.1g-2.66(m,8H,C~12CH of Gln,3CH2CO), 2.35(t,2H,JCH2CH27.7HZ,CH2CO of Gln), 3.69(s,3H,COOMe), 5.30(m,1H,H-3 oi C14OC16), 6.05(d,1H,J1 2,2.9Hæ,H-l) Example 19 N- E 2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-hexadecaonyloxytetradecanoyl)-l-thio-~-D-~lucop~ranos-3-yl}-D-lactoyl]-L-alanyl-D-lsoqlutamine methylester Thc compound oE thc Eormu:La (III) whcrcin ~1 is 3-hcxadccanoyloxytctradecanoyl-thio (586.,6mg, 0.580mmol) was dissolved in 30~ acetic acid aqueous solution 2 0 ~

(12ml), which was allowed to stand for an hour at 45C.
In the same manner as that in Example 4, the title compound (563.4mg) was quantitatively obtained.
mp : 94.6-95.8~C
[a]D : +28.06~C=1.112, CEI2C12- : MeOH=1 : 1) IR ~max(cm 1) : 3680-3130(0H), 3300~NH), 2940, 2870(CH), 1740(ester), 1650, 1550(amido) NMR(CDCl3) : 0.88(t,6H,JMeCH26.4Hz,2MeCH2), 1.27(m,40H,20CH2), 1.37(d,3H,JMeCH7.OHz,MeC of Lac), 1.41(d,3H,JMeCH7.0Hz,MeC of Ala), 1.60(m,4H,2MeCH2), l.91(s,3H,AcN~, 1.91-2.02(m,1H,CHCH2 of Gln), 2.21-2.90(m,6H,CH2CO of Gln,2CH2CO), 3.70(s,3H,COOMe), 4-05(t,1H,J6a 6b,10.3Hz,H-6a), 4.22-4.26(m,2H,CH of Lac and Ala), 4.34-4.39(m,1H,CEI oE G:l.n), 5.13(d,1M,;J1 210.6Hz,M-l), 5.21-$.25(m,1H,H-3 of C1~OC16) 2~ 2~ 3 Example 20 N-~2-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl 1-S-((3R)-3-hexadecanoyloxytetradecanoyl)-1-thio-B-D-gluco~yranos-3-yl}-D-l~ctoy:L]-L-alanyl-D _soglutamine methylester The compound of the formu1a (l'~ wherein R1 is 3-hexadecanoyloxytetradecanoylthio(340.0mg, 0.350mmol) was dissolved in a mixture of dry dioxane (4.Oml) and dry DMF(1.5ml). To the solution were added octadecanoic acid(129.4mg, 0.455mmol), DCC(144.4mg, O.700mmol) and DMAP~21.4mg, 0.175mmol). The resultant was stirred ~or 3 hours at room temperature. In the same manner as that in Example 14, the title compound (203.lmg, yield : 46.8%) was ob-tained.
mp : 171.2-172.8C
[a]D : +17. OlD ( C=O . 723, CH2C12 : MeOH=2 : 1) IR rmax(cm ) : 3320, 3270(NH, OH), G920, 2850(CH), 1740(ester), 1650, 1540(amido) NMR(CDC13) : 0.87(t,9H,JMeCH5.3Hz,3MeCH2), 1..25(ln,10}1,35CII~), L.39(d,311,.lMcCI-l6.611z,MeC Or Ala), 1.58(m,6H,3MeCH2), 1.94(s,3H,AcN), 2.22~2.91(m,2H,CH2CO of Gln), 2.32(t,2H,JCH2CH27.7Hz,CH2CO of Gln), 3.~9(s,3H,COOMe), 5.13(d,1H,J1 211.0Hz,H-l), 5.11-5.20(m,1H,H-3 o~ C]4-O-C16) Example 21 N-~2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-octadecanoyloxytetradecanoyl)-a-D-glucopvranos-3-Yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester The compound of the formula (III) wherein R1 is 3-octadecanoyloxytetradecanoyloxy(388.9mg, 0.380mmol) was dissolved in 80% acetic acid aqueous solution(15ml), which was allowed to stand for 2 hours at 45DC. In the same manner as that in ~xample 4, the title compound (3-73.7m~) was ~uantitatively obtained(373.7mg).
mp : 187-188.5C
[a]2D5: +47~11(C=0.900, CH2C12 : MeOH=1 : 1) IR Ymax(cm l) : 37n0-3100(0H), 3300(NH), 2910, 2850(C~), 1740(ester), l650, 1540(amido) NMR(CDCl3) : 0.88(t,9H,.IMelC~]77.0~1z,3MeCi-12), 1.25(m,44H,22C~12), 1.41(d,311,JMeCH7.8Hz,MeC of Ala), ~6 2 ~J '3 1.44~d,3~l,JMeCH7.8Hz,MeC of Lac), 1.99(s,3H,AcN), 1.94-2.04(m,?ll,CH2CH of Gln), .30(t,2~1,Jc~l2cl-128~ n z, cH2Co 0~ Gln), 2.27-2.46(m,6H,3CH2CO), 3.70(s,3EI,COOMe), 5.30(m,lH,H-3 of C14OC18), 6.05(d,1H,J127.8HZ,H-l) ExamE~
N-[2-0-{2-~cetamido-2,3-dideoxy-6-0-octadecanoyl-1-0-(~3R~-3-octadecanoyloxytetradecanoyl)-a-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoqlutamine methylester The compound of the formula (I') wherein R1 is 3-octadecanoyloxytetradecanoyloxy(177,Omg, 0.18mmol) was in a mixture of dry dioxane(3.Oml) and dry DMF(l.Oml).
To the solution were added octadecanoic acid~66.6mg, 0.234mmol), DCC(74.3mg, 0.36Ommol) and DMAP(ll.Omg, 0.090mmol). The resultant was stirred for 16 hours at room temperature. In thc same manllcl a.s that in Examplc 11, the t:Ltle compollnd (164.0mg, 72.3'-'~,) was obtained.
mp : 106-108.5~C
[a]2D5: ~38.46(C=0.62~, CH2Cl2 : MeOH=1 : 1) 2~ ,J.-3 IR Ym~x(cm 1) : 3700-3150(H), 3300(NH), 2930, 2860(CH), 1740(ester), 1660, 1540(amido) NMR(CDC13) : 0.88(t,9H,JCH2CH266Hz,3MeCH2), 1.25(m,72EI,36CH2), 1.43(d,3H,JMeCH6.2Hz,MeC of Lac), 1.59(m,6H,3MeCH2), l.99(s,3H,AcN), 2.01-2.20(m,8H,CH2CH of Gln,3CH2CO), 2.30(t,2H,JCH2C~27.7Hz,CH2CO of Gln), 3.69(s,3H,COOMe), 5.30(m lH H-3 of C OC
6.05(d,1H,J1 23.0Hz,H-l.) Example 23 N-~2-0-{2-Acetamido-2,3-dideoxy-1-S-((3R)-3-octadecanoyloxytetradecanoyl)-l-thio-~-D-~luco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoqlutamine methylester The compound of the formula (III) wherein Rl is 3-octadecanoyloxytetradecanoylthio(634.11l~cJ, 0~610mmol) was dissolv~d in 80'-~, acetic acid acqueous solution(15ml), which was allowed to stand for an hour 2~1~.2 t,l~

dt ~5~C. In the same manner as that in Example 4, the title compound (609.6mg) was quantitatively obtained.
mp : 112.5-113.8C
La]2D5 ~24.62(C=0.600, Ch2Cl2 : MeOH-1 : 1) IR Ymax(cm ) : 3400-3100(0H), 3260(NH), 2910, 2850(C~
1740(ester), 1640, 1530(amido) NMR(CDCl3) : 0.88(t,6H,JMeCH2,4.0Hz,2MeCH2), 1.25(m,44H,22CH2), 1.33(d,3H,JMeCH7.3Hz,MeC of L.ac), 1.36(d,3H,JMeCH7.3Hz,MeC of Ala), 1.58(m,4H,2MeCH2), 1.92(s,3H,AcN), 1.91-2.04(m,2H,CHCH2 of Gln), 2.26(m,6H,CH2CO of Gln,2CH2CO), 3.69(s,3H,COOMe), 4 02~4 09(t lH J6a 6b8 7HZ'H-6a) 4.28(m,1H,CH of Gln), 5.08~d,:1.11,J1 2'1.011Z,H-L), 5.21(m,LII,~l-3 oE cl4-o-cl~3) Rxample 24 _~2-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-2~ ~ 273 1-S-((3R)-3-octadecanoylox~tetradecanoyl)-1-thio-~-D-~_ucopYranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester The compound of the formula (I') wherein R1 is 3-octadecanoyloxytetradecanoylthio(400.Omg, 0.400mmol) was dissolved in a mixture of dry dioxane (4.Oml) and dry DMF(1.5ml). To thc solution were added octadecanoic acid(147.9mg, 0.520mmol), DCC(165.lmg, 0.800mmol) and DMAP(24.4mg, 0.200mmol), and the resultant was stirred for 3.5 hours at room temperature. In the same manner as that in Example 14, the title compound (258.6mg, yield : 51.0~) was obtained.
mp : 123.1-124.5~C
[a]D : ~17.01(C-0.723, CH2C12 : MeOH=2 : 1) IR Ymax(cm 1) : 3650-3150(0H), 3300(NH), 2930, 2850(CH), 1730(ester), 1650, 1550(amido) NMR(CDCl3) : 0.88(t,9H,JMeCH25.5Hz,3MeCH2), 1.25lm,7~l1,37CH2), 1.34(~,3H,JMeCH6.6Hz,MeC of Ala), 1.44-1.67(m,6H,3MeCH2), 1.85(s,31-1,AcN), ~0 2~ ~2 ~r) 2.17-2.79(m,2H,CH~CHof Gln), 2~31~t,2H,JCHh?CH?8.4Hz,CH2CO of Cln), 3.70(s,3H,COOMe), 5.10(d,lH,J1 210.6Hz,ll-l), 5.14(m,1H,H-3 of Cl4OC18) Example 25 N-[2-0-{2-Acetamido-2,3-dideoxy-1-0-((3R)-3-tetracosanoyloxytetradecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester The compound of the formula (III) wherein Rl is 3-tetracosanoyloxytetradecanoyloxy(465.2mg, 0.420mmol) was dissolved in 80% acetic acid aqueous solution (15ml), which was allowed to stand for an hour at 45C.
In the same manner as that in Example 4, the title compound(448.3mg) was quantitatively obtained.
mp : 183.5-185C
[a]2D5: +34.13~ (C=0.920, CH2Cl2 : MeOH=2 : 1) IR Ymax(cm 1) : 3700-3120(0H), 3300(NH), 2930, 2850(CI~I), l140(est~r), 166(), 1540(amldo) NMR~CDCl3) : 0.89(t,9H,JMeCH26.6Hæ,3MeCH2), ~1 2~2~.9 l.25(m,56H,28CH2), 1.41(d,3H,JMeCH6.9Hz,MeC of Ala), 1.44(d,3H,JMeCfl6.9Hz,MeC of Lac), l.60(m,6H,3MeCH2), l.99(s,3H,AcN), 1.94-2.01(m,2H,C~2CHof Gln), 2.20-2.39(m,6H,3CH2CO), 2.2g(t,2H,JCH2CH213Hz,CH200 of Gln), 3.69(s,3H,COOMe), 5.30(m,lH,H-3 oE Cl40C24), 6.05(d,1H,J1 22.9Hz,H-l) Example 26 N-[2-0-{2-Acetamido-2 3-dideoxY-6-0-octadecanoyl-1-0-((3R)-3-tetracosanoylo_y etradecanoyl)-a-D-gluco-pyra-no-s---3-yl~-D-lactoyl]-L-alanyl-D-isoqlutamine methylester The compound of the formula (I') wherein R1 is 3-tetracosanoyloxytetradecanoyloxy (234.8mg, 0.220mmol) was dissolved in a mixture of dry dioxane t3.Oml) and dry DMF(l.Oml). To the solution were added octadecanoic acid (81.3mg, 0.286mmol), DCC (90.8mg, 0.440mmol) and DMAP~13.4mg, O.llOmmol), and the resultant was stirred for 12 hours at room temperature.
In the same manner as that in Example 11, the title compound (200.7mg, yield : 68.3%) was obtained.

s ~p : 66.5 68C
~a]25: +34.11~ (c=0.680, CH2C12 : MeOH=l : ll IR ~max(cm ) : 3700-3100(0H), 3300(NH), 2930, 2850(CH), 1760(ester), 1660, 1540(amido) NMR(CDCl3) : 0.88~t,9H,JCH2CH26.6Hz,3MeCH2), ].25(m,88H,44CH2), 1.43(d,3H,JMeOH6.6Hz,MeC of Ala3, 1.44(d,3H,JMeOH7.0Hz,MeC of Lac), 1.61(m,6H,3MeCH2), 2.00(m,8H,CH2CH of Gln,3CH2CO3, 1.99(s,3H,AcN), 2.33(t,2H,JCH2CH24.2Hz,CH2CO of Gln).
3.65(s,3H,COOMe), 4.20(q,1H,JMelCH,Hz,MeCH of Ala), 5.29(m,1H,H-3 oE C OC
6.04(d,1H,J1 233HZ,l-H) Example 27 N-[2-0-{2-Acetamido-2,3-di eoxy-l-S- ~ ~-3-tetracosanoyloxytetradec~ l)-l-thio-~-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoqlutamine methYlester 9~

2 7 `~3 Thc compound of the formula (III) wherein R~ 1s 3-tctracosanoyloxytetradecanoylthio (617.9mg, 0.550mmol) was dissolved in 80~ acetic acid aqueous solution (12ml), which was allowed to stand for an hour at 45C.
In the same manner as that in Example 4, the title compound (595.9mg) was quantitatively obtained.
mp : 168.5-170.1C
[~]D5: +5.18~ ~ C=0.772, CH2Cl2 : MeOH=1 : 1) IR ymax(cm ) : 3500-3200(0H), 3280~NH), 2910, 2850(CH), 1720~ester), 1630, 1540~amido) NMR~CDCl3) : 0.88(t,6H,JMe1CH2 Hz,2MeCH2) 1.25(m,56H,28CH2), 1.30(d,3H,JMeCH8.3Hz,MeC of l.ac), 1.34(d,3H,JMeCH7.5Hz,MeC of Ala), 1.58(m,4H,2MeCH2), 1.97-l.91(m,2H,2MeCH2), 1.94(s,3H,AcN), 2.25(m,6M,CHCH2 oE Gl :l.69(s,3ll,COOMe), ' ' 6a,6b ' )' 4.24-4.28(m,1H,CH of Gln), 5.09(d,1~1,J~ 210.8Hz,H~
5.13-5.19trn,1H,H-3 of C14-O-C24) Example 28 N-[2-0-{2-Acetamido-2,3-dideoxy-6-0-octadecanoyl-l-S-((3R)-3-tetracosanoyloxy~etradecanoyl)-1-thio-~-D-qlucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester The comp~und of the formula ~I') wherien Rl is 3-tetracosanoyloxytetradecanoylthio (411.amg, 0.380mmol) was dissolved in a mixture of dry dioxane (4.Oml) and dry DMF (1.5ml). To the solution were added octadeconoic acid (140.5mg, 0.494mmol), DCC~156.8mg, 0.76Ommol) and DMAP (23.2mg, O.l90mmol~, and the resultant was stirred ~or 3 hours at room temperature. In the same manner as that in Example 14, the title compound (223.5mg, yield:43.5~) was obtained.
mp : 147.5-149.0~C
[a]D +17.40 ( C=0.632,CH2C12 : MeOH=l : 1) IR y max~cm l) : 3600-3200(OH), 3300(NH), 295~, 28~0(C~I), 1750(ester), 1660, 1560(amido) NMR(CDC13) : 0.88(t,9H,JMeCH5.5Hz,3MeCH~), , 7 3 1.25(m,86H,43CH2), 1.35¦d,3H,JMeCH6.3Hz,MeC of Ala), 1.57(m,6H,3MeCH2), 1.90(s,3H,AcN), 2.05-2.90(m,2H,CH2CH of Gln), 2.35(t,2H,JCH2CH27.8Hz,CH2CO of Gln), 3.68(s,3H,COOMe), 5.13(d,1H,J1 211.0Hz,H-l), 5.15(m,1H H-3 of C OC

Pharmacological activities of the compounds of the present invention are shown as follows.
(1) Hepatitis-vaccine enhancing activity (adjuvant activity) A compound of the present invneiton was dissolved in lipidmicrosphere llmg/ml). On the other hand, a solution of hepatitis B virus surface antigen ¦HBs) in physiological saline was prepared 150~g/ml). The above solutions in equal amounts were mixed to prepare a test solution. A control solution was prepared by the exclusion of the compound of the present invention from said test solution. A mixture of a suspensLon of aluminium hydroxldc gel in phys:iolog1cal sal:ine (lmg/ml) and said hepatitis vaccine preparation in equal amounts was prepared as another control solution.
The test solution (0.2ml) was intraperitoneally 2 ~1 ~3. 2 ~J~1 administered to each mouse in one group consisting of seven female CDF'l mice.
Blood samples were collected from the fundus ocluli vein of each mouse every week after the administration and then centrifuged to obtain serums.
Three weeks after the administration, 0.2ml of the test liquid was intraperitoneally administered again to each mouse for secondary stimulation. Then blood collecting was conducted every week to obtain serums after the application of the secondary stimulation, in the same manner as that described above.
The amount of the IgG antibodies against the hepatitis B virus surface antigens (HBs) in the serums thus obtained was determined with an ELISA method. The results are shown in Table l.

Tl ~ 3 A(l i uv lll t ~c C iv i ~ i e~; on llep t.l t i .s 13 Vil~ '.UI-t~Ce <'Illl-ij~`ll~'`. - i',XI)el:inlell~ I
. _ _ _ _ . _ _ _ . _ . _ _ _ _ _ _ . _ _ . _ . _ _ _ _ _ _ . . . _ . _ . . _ _ _ _ . _ _ _ _ _ _ . _ . _ . _ . _ . _ . _ _ _ _ _ . . . _ . _ _ _ _ . _ _ _ . _ _ _ _ _ _ . _ _ _ Auti 1113; ~erulTI uu Lif!eu vllue (clverage vllue t S. D .) re~:L __ __ _ _ _ __ __ 0.1)_115ll~ 5000-tc)l~i ~iiLu~:ion materia I
____ 1 ~ l ___: ___ _ --- 3-- ~ W _ __ 5 W___ Lx~ml~le ] 0.001-~-0.0()1 0.018-1-0.()00 0.074-iO.002 0.815-10.01 L 0.843-1-0.005 ~ __.__ I _~ _ _____~_ . __ . _ __ _ _ . ~_ _._.
2 O 0.0231().()0() ().()76-1-().0()1 0.975_().0()~3 0.93()_0.00~1 _ _ ____ _ __ ___ I __ _ . __ _~. _ _ _ ____ ____ _ _ 3 O ().027+0.001 0.064-!-0.003 0.6:31+0.006 ().692_0.()09 _~_.__ _ ___ ___ ___ _ _ __.___. _ _ _. _ I_ _.. _ ___ ._ _ ___ . _ 4 O 0.073_0.001 0.111_0.007 0.8~18-~-0.009 0.935_0.022 _ _____ _ __. I _______ 50.~)01-tO.001 0.021-tO.001 0.04~3-tO.001 0.643-1-0.()13 0.490_0.009 __ __ . _.___ _ I- .____ __. ___ 6 O () .020_0.002 O .069_0.001 O .477-'0. ()()5 ().529_0.005 _ ~____ ___ _ __ __ __ 7 O ().0]6-1-0.()03 0.071-tO.004 0.42(1-10.000 O.ll7o-!-().olo ~ ._ __ . _ ________._ __ __ _ .. __ .. _ .__ ___ .____ _. . __. _.___ _ ~3 () O.()67L().()()3 ().1~4_0.002 0.897+0.012 0.845_0.0~6 _____ ___ _ _ ___ _.. _ ~__ __ ____ . ___ 90.014_().002 0.()921-0.003 ().14(~_0.001 ().~181 0.012 0.702LO.006 . ._______ ._ _ ____ I_ . _ _ 10O 0.0611-0.002 0.114_0.003 0.778_0.02~ 0.87~3_0.009 _ _ ___ .__ .___ _ ~_____ _____ __ _____ _ _._ 110.010_0.002 () .083 '0.0()2 0.124+() . ()03 () . G02-l~o . ()()9 () .7 L 6-'0.020 _ __ _. _.. ____ _ _._ _ _ _ __ __ _____ _ .. _ _.
120.007-~-0.()03 ().109_0.002 O. Lll ~O.OOl 0.60-3+0.021 ().695-~0.021 __ ~ _ __ _ ___ _____ I _=_ _ __._--13O () .0-31 -J () . ()03 () . ] 26-1 () .003 0.635 0. () 11 () .7/~21 () . () I ~) _ . __ __~ _ _.__ . .. .. .___ __. __ .. _ .. ... _ .. . .
lll (~ () . ()71 -1 () . (~()(I () . 1 ()~l;! () . ()() ~ () . 71~ () ~IG ! () ()~l ______~. _. ._.. __ .. _.. __. ~ .. __ ._ . f.~.~.. _.. ~. ._.. .. . _ .. _ .. . _ .. _.. __.__.. ._.. _ . _ . _.. .. . ., _ .. ...... ___.. __ _ .. ~_ . __._ _ .
~; () () . ()~IS 1-() . ()()~ () .12() 1 () . ()() I () .7~ 3 ().9iJS I-() . ()~() _ _._ .. _ _.. _... _ ...... _. _ _ _ _ _ . . _ . _ _ . _ __ . ....... ._ _ _ __ . _. _.. ..
1 (~ () () . ()79-L() . ()()4 () .103 ~() . ()()l~ () . f3 jO-1-() . ()08 () 9()31-() .021 A.i~ T~Il _________ _____ ___ . ___ __ _ . ._ . __ .. _ __~ _____ ..... . _ .
Il~ OX i ~le O () () () .027-.'0. ()() ~ () .04()-1-0. O() I
( Olltl-o ~ () () O () .097-'0.006 ).123.'() . ()O
_____ ___.. _ . _ . _ _ ._ _ _ _ .. _ ___._ _ _ _ __ _. ._ _ _ __ .___ _ _. _ __ _ _ _ __ _ '1',11! I r I ( ( ol t~

A~ v~ c~t ivitirs oll llel-tal:is 1 Vil-U.~ ~lrl~nce clntigcll~ xlerilllel~t 2 _ _ _ _ _ _ . . . _ _ . _ .. _ _ . _ _ . _ _ _ . _ .. _ _, . . _ _ .. _ . . _ . . , . .. . . , . . , _ _ _ _ .
Alri ill~ er~lm ;Illtlprll vnllle ~nv(r;~e v.ll~le -1- S~1).5 Ic~c O.i) ~llSIllll 2()~()()-r~ lLLl~Ll . _ __ __ _ _ _ _ _ .__, __ __ _,__ _ _ _ __ _ . _ ___ _. _, , _ _ _ _ _,, __ _._ _, _, __ . _ _ . _ _, _ _ _ . . _ _. . _ . .. _ _ _ _ . . ., _, . _ . : ., __ _ _ _ , _ . .
, _ ___ m(~teria L I W 2 W 3 W 4 W 5 W
__ __ _ __._ _________ _____ _ ,__________. ,._ _ ____ Ex~ml le 17 O.001 i-0.004 0.o26-to ool 0.051 ~0.001 0.642-~().021 O.6l5~0.021 ~ . ,__ ___ __ ___ _____ . _ I _. . ___ .. _ ., ___ __.__ 18 () 0.03510.0()7 0.050~().004 0.481~().00~ ().375~0.0()8 . _ ,_ _ _ __ , _ . .. _ _ ____ _ ___ _ _ ___~ __ _ .__. _ ____ ,___--. ___ _ ______ _____ _ _ 0.023-1-0.000 0.~ .OOl ().536-~0.011 ().5Z~ i-0.012 20 0.002-iO.O()1 O.()~ 0.005 0.056iO.0()3 0.81~ ().018 0.7()810.0()2 ,______ _ ___ ____ ,_ _ ._ __ _.,_____, ._ ___ _ _ _ 21 0.0(16-~1).00~i 0.033_0.000 0.058~-0.007 0.5]7~).006 0.~19~ O.Oll 22 0.005 ~0.004 0.036-~-0.00 ().053-1-0.001 0.29~ 06 ().25~110.002 _ _~_ _ O . (iO~I l O . ()01 () . ()5110 ()03 0.09210.004 () .6391 () . ()03 O . (2610. ()()8 __~__ 0.()()71-().001 0.()34-10.001 0.050-1-0.0()0 0.579H).()07 ¦ ().513-1-0.011 0.004-1-0.002 0.021~0.001 0.031-~0.004 0.402+0.011 0.434+0.021 .. .__._._ __ . -- 1- ----- - ~
26 0.001-~0.006 0.015+0.006 0.032-L-().0()8 0.192-~0.002 O. lfi3-iO.OO~
_ _ ___.__ __ . __,._,___. _.._ ._. ,_.__, _ . __ ___, 27 0.0031-0.0()3 0.031 i-0.002 ().()52-1-().()()() 0.58()-1-0.()1~) ().573-~0.013 ~_ _ ___, _.__ ___ ,______.____ __ _ _____._, _, __ ___ 2# () .0()51-0.003 () . OG21-0.004 O . ()86 ~0. no4 () .61 L-l-() .018 0.543-1-() . ()29 _ ,._ ._ .,__ _ . . .___ . _ _ __ _ __ __.
A Lulr:i num llydroxi(le () 0.002+0.002 0.006-i 0.0()4 () . L 96-1 () . ()03 0.2 ? 71-() . ()() I
~el ___ _____ __ ___ _ __ .

7.`~

(~.) Influenza HA vaccine enhancing activity (adjuvant activity) ~ compound of the present invention was dissolved in lipidmicrosphere (lmg/ml). On the other hand, a solution of influenza HA vaccine (B/nagasaki/1/87 strain) in physiological saline was prepared (100 ccA/ml). The above solutions in equal amounts were mixed to prepare a test solution. A control solution was made by the exclusion of the compound of the present inveniton from said test liquid. A mixture of a suspension of aluminium hydroxide gel in physiological saline(lmg/ml) and said influenza HA
vaccine preparation in equal amounts was prepared as another control liquid. The test solution (0.2ml) was intraperitoneally administered to each mouse in one group consisting of seven fema]e CDF1 mice.
Blood samples were collected from the fundus oculi vein of each mouse every week after the administration and then centrifuged to obtain serums.
Three weeks after the aministration, 0.2ml of thc test liquid was intraperitoneally adminlstercd again to each mouse for secondary stimulation. Thcn, blood collecting was conducted every week to obtain serums after the 2 ~ 7 ~

application of the secondary stimulation, in the same manner as that described above.
The amount of the IgG antibodies against the influenza HA vaccine (B/Nagasaki/1~87 strain) i.n the serums thus obtained was determined with an ELISA
mehtod. The results are shown in Table 2.

lO1 2 ~ 7 3 '1 .11) 1 ~ 2 Acl j~lv~nt aeLivltie~; o~ rlue~ a IIA
v~ccine~q - l xi-er.illlent I

~ e~~ F~ell -v~T-llc ~lvern~ v.1IIIe~~~.lS~l -'re.st ____ _ _ O.D 415nll1 5000-r~-ld dil.lJt:i.o m.~ t e r icl I ~

_ ~ . __________ _. __ _ _____. ___.__ __ ____ Ex~mple I 0.007-tO . ()03 0.174~0.003 0.232+0.003 L .2431-0.036 1.201+0.002 - ------1- ---- I -------------- ----------- --- ~
2 0.003+0.()(1l0.172+0.004 0.420-~U.005 1.447-to.029 1.418~0.035 _ __ _ _ __ _ _ 3 0.009~~0.000 0.182+0.003 0.292~0.004 1.12~+0.020 1.1~0~0.013 -- ---- 1- _ . ._ ~ 0.004+0.001 0.215-~0.0010.381-~0.004 1.20~1l0.012 1.150-~0.016 _ ~ _ _ __ ~ _ ...... _.
O 0.091+0.002 0.377+0.001 1.037.tO .027 1.068+0.004 I . _ __ _ _ __ ___ __ 6 0.001+0.001 0.013+().002 0.259+0.004 1.025-~0.013 1.159~-0.013 _ _ , _ .... . _ 7 0.001-tO.001 0.112+0.003 0.286+0.001 1.039-tO.OlO 1.128+0.026 l . ~_ _ __ . . I
8 0.0()1-1-0.001 O. L()5-1-().005 0.24G-~().004 L.246-1-O.OL9 1.2fi7-1-0.023 ._ _ __ __ __ ' . - ___ 9 0.019+0.002 0.168+().005 0.392+0.006 1.342-~0.005 1.329+0.026 . 1- -- . _ 0.005+0.001 0.153+0.003 0.280+0.000 1.149+0.018 1.203+0.014 . ._ I __ _ ,__ .__ _ 11 O 0.073+0.000 0.160~0.005 L.059-~0.OlG L .050-1-0.003 _ _ __ .. _ .__ __ 12 0 0.105+0.00~1 0.176+0.002 1.039 ~0.015 1.050 ~0.008 I _ . _ _ . _ _ . . _ _ 13 0 0.088-~0.004 0.140-~0.001 0.868+0.010 0.824-~0.002 . _. _ ._____ ___ 14 0 () . l l()t 0.003 0.186 ~0.007 0.974 ~(~ .006 () ,95~ 0.0() 2 (),0()71(),0()() ().1191(),()()5 ().?181-().()()fi 1.2491-().()13 1.2fi?1().()17 ___ __._ .. _ _ _. .. ~ ..... _.. .... ~ ~...... .... _.. ~ .. _ ._. __ .. _. _ lG 0.001~-O.001 ().1451-().004 0.257-1-0.01() 1.25110.010 1.262i0.026 '~T---r--- '--~--'----. _ I~lUmlnUIIl --- --- ~ ~ ~
~e 1 O O ~ O 0.162-10. ()04 0.263 t0.007 _ _ . ... _.... ... __ ____ _______._ ____ .
Cotltro l. 0 O _ O . ~110-l-0.004 () .502+0.0n8 _ ___ .__ _ _ ____ _ __ 2~2~'3 * Ad; UVtlllt ac t; v i t i e~ oll i ll r l uen7~a IIA
v a c c i n e e. - I' x 1~ e r i me n t ?
___ ___ ~-Ai~i`L~ilA-seruiii .lni l~geiï vtilue T~ernPe vnluie ~ S.i).~
I ~ ~ t _ _ ___ __ _ _ _ ___ __ 0.1) ~ l SIllll 80000- f o ~ _1_cl L~ iOIl_ mtlter i n i I W 2 W 3 W ~ 5 W
____ _ .. ___ ._____ __ . . _.. __ . .. __ _ __ __ ~_ _ __ _ _ _ __ L.xall?i le 17 ().010+0.002 O. L22-1-0.0()6 U.19110.00L 0.611 i-0.017 0.696-iO 014 18 O 0.05Z ~0.004 0.075+0.001 0.370+0.005 0.360-iO.0()1 __ ___ _ ___ ----- 1-` ---- -~ -~
19 O () .125 i 0 003 O .187-~0.001 O .872 i-O .002 O .936-~0.006 _ __ _. _ _ _ 20O.t;OI i-O.OOI 0.071-iO.OOI O. l`l"O-iO.008 0.840i-0.011 0.857-iO.023 21 O O.Ofi()-l().OOl 0.097~0.002 0.7~8+0.003 0.758iO.012 _ ~ _ . _ 22O . OOl-i-0.004 O .065-i-0.00 L 0.100+0.003 0.411+0.009 () .492+0.002 _ __ ~ _ __ ~.___ 230.008-~-0.005 0.096-i-0. no I o . 183 i 0.004 0.9~ 9 i 0.006 1.030 ~0. ()03 ___ ____ __. __ _____ __ ~ ____ __ 24 O . O()G-I-O . ()() 1 () .0~510. ()()5 O .113-~-0. ~)07 () .771-1-() .003 O .791 -i-O .00~
_ _ _ _ _. ~ 1- 1 __ 0.009i-0.001 0.109-iO.002 0.149i-0.004 0.623-io.oL9 0.719+0.021 - - 1- - ----- ------- '-- - ~
26 0.004_0.003 0.038-~0.001 1 0.054-i-0.001 U .208 ~0.001 O .206 i 0.0()2 27 O 0.110_0.003 0.161_().003 O.7511-0.004 0.805 ~0.008 ___~_ _. _______ __ ____ 28 O.OO#i-().Ool~ ().041_0.0()~ 0.061_0.001 0.787_0.018 0.779+0.02~
__ ___ __ _ _ _ ___ ____ /~] umillum hydroxide O O O O .152_O .008 0.18 L i 0.0()8 ge l l _ _ _. __ ~ _ .. _ _ _ .
Contro1 () ().()46-1-().()()1 ().()711().()()/1 ().'18t)1~().()()4 ().'lil81().()() .. .. .

2 ~ r~ r~

(3j Activation of macrophages (an effect which inhibits the growth of tumor cells) A compound of the present invention was dissolved in lipidmicrosphere to obtain a solution in a concentration of 500~g/ml, and 0.2ml of such solution was intraperitoneally administered to each mouse in one group consisting of seven female CDFl mice.
Intraperitoneal macrophages obtained three days after the administration and L-1210 mouse leukemia cells were mixed in the ratio of cell numbers of 20 : 1, respectively. Two hundred ~1 of the mixture was placed in each well of one sheet of 96 well microtiter plate.
After 72 hours, the increase oE the cell number in each well was determined by a MTT assay method. The ratio of the cell number for the mixture of the L-1210 cells and the macrophage relative to the cell number for the L-1210 cells only(growth inhibi-tory ratio) was determined, and the results are shown in Table 3.
10~

~ 3 Table 3 _________________________________ ______________ Test Growth inhibitory ratio o-E
m~terial L-1210 mouse leukemia cells~%) ____________________ .___________________________ Example 1 40.0 2 41.3 3 42.6 4 45.2 57.8 6 63.0 7 90.2 g 57.9 9 58.5 76.6 11 59.7 12 79.0 l3 39.7 1~ 96.4 ].5 87.5 16 76.3 Control 9.L
____________________________________________

Claims (13)

1. A muramyl dipeptide derivative of the following formula (I):
(I) wherein "Ala" is "isoGln" is ;
R1 is R30- or R3S-[R3 is (k is an integer from 8 to 12; q is an integer from 10 to 22) or R3 is (m is an integer from 11 to 17; n is an integer from 11 to 17)]; and R2 is hydrogen atom or -CO-(CH2)p-CH3 (p is an integer from 8 to 22)
2. A compound of claim 1 wherein R3 is 2-tetradecylhexadecanoyl.
3. A compound of claim 1 wherein R3 is (3R)-3-tetradecanoyloxytetradecanoyl.
4. A compound of claim 1 wherein R3 is (3R)-3-hexadecanoyloxytetradecanoyl.
5. A compound of claim 1 wherein R2 is hydrogen atom.
6. A compound of claim 1 wherein R2 is tetradecanoyl.
7. A compound of claim 1 wherein "Ala" is L-alanine residue, and "isoGln" is D-isoglutamine residue.
8. A compound of claim 1 which is N-[2-0-{2-acetamido-2,3-dideoxy-1-0-(2-tetradecyl-hexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L--alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-6-0-decanoyl-1-0-(2-tetradecylhexadecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-6-0-tetradecanoyl-1-0-(2 tetradecylhexadecarloyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-6-0-octadecanoyl-1-0-(2-tetradecylhexadecanoyl) .alpha.-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-1-S-(2-tetradecyl-hexadecanoyl) 1-thio-.beta.-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido 2,3-dideoxy-6-0-decanoyl-1-S-(2-tetradecylhexadecanoyl)-1-thio-.beta.-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-6-0-tetradecanoyl-1-S-(2-tetradecylhexadecanoyl)-1-thio-.beta.-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamlne methylester, N-[2-0-{2-acetamido-2,3-dideoxy-6-0-octadecanoyl-1-S-(2-tetradecylhexadecanoyl)-1-thio-.beta.-D-glucopyranos-3-yl}-D-lactoyl}-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-1-0-((3R)-3-tetra-decanoyloxytetradecanoyl)-.alpha.-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-6-0-decanoyl-1-0-((3R)-3-tetradecanolyloxytetradecanoyl)-.alpha.-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-(2-acetamido-2,3-dideoxy-6-0-tetradecanoyl-1-0-((3R)-3-tetradecanoyloxytetradecanoyl)-.alpha.-D-gluco-pyranos-3-yl}-D-lactoylJ-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-6-0-octadecanoyl-1-0 ((3R)-3-tetradecanoyloxytetradecanoyl)-.alpha.-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methyl.ester, N-[2-0-{2-acetamido-2,3-dideoxy-1-S-((3R)-3-tetra-decanoyloxytetradecanoyl)-1-thio-.beta.-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-6-0-decanoyl-1-S-((3R)-3-tetradecanoyloxytetradecanoyl)-1-thio-.beta.-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-6-0-tetradecanoyl-1-S-((3R)-3-tetradecanoyloxytetradecanoyl)-1-thio-.beta.-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-6-0-octadecanoyl-1-S-((3R)-3-tetradecanoyloxytetradecanoyl)-1-thio-.beta.-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-didcoxy-l.-0 ((3R) 3-hexa-decanoyloxy-tetradecanoyl)-a-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0 {2-acetamido-2,3-dideoxy-1-0-((3R)-3-hexa-decanoyloxytetradecanoyl)-6-0-octadecanoyl-.alpha.-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamlne methylester, N-[2-0-{2-acetamido-2,3-dideoxy-1-S-((3R)-3-hexa-decanoyloxytetradecanoyl)-l-thio-.beta.-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-1-S-((3R)-3-hexa-decanoyloxytetradecanoyl)-6-0-octadecanoyl-1-thio-.beta.-D-glueopyranos-3-yl}-D-lactoyll-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-1-0-((3R)-3-octa-decanoyloxytetradecanoyl)-.alpha.-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester , N-[2-0-{2-acetamido-2,3-dideoxy-6-0-octadecanoyl-1-0-((3R)-3-octadeeanoyloxytetradecanoyl)-.alpha.-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-1-S-((3R)-3-octa-decanoyloxytetradecanoyl)-l-thio-.beta.-D-glueopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutmine methylester, N-[2-0-{2-acetamido-2,3 dideoxy-6-0-octadectlnoyl-1-S-((3R)-3-octadecanoyloxytetradecanoyl)-1-thio-.beta.-D-glueopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-1-0-((3R)-3-tetra-cosanoyloxytetradecanoyl)-.alpha.-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-6-0-octadecanoyl-1-0-((3R)-3-tetracosanoyloxytetradecanoyl)-.alpha.-D-gluco-pyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, N-[2-0-{2-acetamido-2,3-dideoxy-1-S-((3R)-3-tetra-cosanoyloxytetradecanoyl)-1-thio-.beta.-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester, or N-[2-0-{2-acetamido-2,3-dideoxy-6-0-octadecanoyl-1-S-((3R)-3-tetracosanoyloxytetradecanoyl)-1-thio-.beta.-D-glucopyranos-3-yl}-D-lactoyl]-L-alanyl-D-isoglutamine methylester.
9. An immunoregulating composition comprising a muramyl dipeptide derivative of the formula (I) as defined in claim 1 and a pharmaceutically acceptable carrier.
10. An immunoregulating composition of claim 9 in which the muramyl dipeptide derivative (I) is a compound in accordance with any one of claims 2 to 8.
11. An immunoregulating composition of claim 9 which is used for enhancing in vivo activity of a BCG, hepatitis or influenza virus vaccines.
12. An immunoregulating composition of claim 9 which is used for enhancing in vivo activity of antibacterial agents.
13. An immunoregulating composition of claim 9 which is used for enhancing in vivo activity of antitumor agents.
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