Dainippon Ink and Chemicals, Incorporated

Nahoko Takahashi

Tadao Shoji

Naoya Ikushima

Takashi Yoshida

Naoki Yamamoto

Hideki Nakashima

Toshiyuki Uryu

Kaname Katsuraya

Koichiro Adachi

Osamu Misumi

Kazuhiko Inazawa

Fusayo Kobayashi

Akira Kasai

Fusayo Kataoka

Oligosaccharide aromatic glycoside sulfates and physiologically acceptable salts thereof, are disclosed. Further, antiviral agents having these sulfate compounds as the active components, and particularly an antiviral agent, wherein the virus is one which causes AIDS (Acquired Immune Deficiency Syndrome), are disclosed. The active components or the glycoside sulfates, and the salts thereof, are characterized by an oligosaccharide aromatic glycoside sulfate in which the hydrogen of the position-1 hydroxyl group of the terminal sugar of an oligosaccharide is substituted with a specified formula having an alkyl group consisting of 1 to 18 carbons, an oxygen or no oxygen, and an allylene group. The number of constituent monosaccharides in the oligosaccharide portion is preferably within a range of 2 to 20. Further, 10% or more of the remaining hydroxyl groups of the sugar subunits are subjected to sulfated esterification. In addition the antiviral agent exhibits low toxicity and is useful in the treatment of AIDS. Furthermore, an oligosaccharide is also disclosed as described above with the exception that it is the hydrogen atom of the position 1 hydrogen group at the terminal sugar residue which is substituted with the specified formula, also described above. However, in addition the remaining hydroxyl groups of the sugar portion of this oligosaccharide are protected by acyl groups or are present in an unprotected form. Also disclosed is a method for the production of an oligosaccharide aromatic glycoside sulfate synthesized by sulfation using a sulfating agent.

Oligosaccharide aromatic glycoside and sulfate thereof

A sulfated oligoglycoside acylate comprising monosaccharides of a single or two kinds as the constituents, wherein the hydrogen in the hydroxyl group at the 1-position of a reducing end sugar of the oligosaccharide formed via the glycoside bond of these monosaccharides has been substituted with an aglycon selected from a group consisting of alkyl groups, aromatic alkyl groups, aromatic alkoxy groups and tocopheryl groups; from 12 to 80% of the residual hydroxyl groups have been acylated with an acyl group selected from a group consisting of aliphatic acyl groups and aromatic acyl groups; and 88 to 20% thereof have been sulfated; or a physiologically acceptable salt thereof provided that compounds wherein the aglycon is an alkyl group and the acyl group is an aliphatic acyl group are excluded is disclosed. Further, an antiviral agent, which exerts a long-lasting antiviral action particularly on HIV, containing said compound as an active ingredient is disclosed.

Sulfated oligoglycoside acylate and antiviral agent containing the same

The present invention relates to novel tocopheryl oligosaccharides, acylated tocopheryl oligosaccharides, sulfated tocopheryl oligosaccharides, and antiviral agents including the sulfated tocopheryl oligosaccharides as active ingredients. In the tocopheryl oligosaccharide, the hydrogen atom of the hydroxy group at the 1-position in the terminal sugar moiety of an oligosaccharide which consists of 3.about.20 of identical or different repeating monosaccharide units selected from the group consisting of glucose, galactose, mannose, talose, idose, altrose, allose, glucose, xylose, arabinose, rhamnose, fucose, and fructose, which are glycoside-linked, is substituted by a tocopherol group. In the acylated tocopheryl oligosaccharides, each of any hydroxy group of the sugar moiety, other than the hydroxy group at the 1-position in the terminal sugar moiety of the oligosaccharide described above, is protected by an acyl group. The antiviral agents including the sulfated tocopheryl oligosaccharides or the biologically acceptable salt of the same as active ingredients have low toxicities and exhibit improved antiviral action, especially against the Human Immunodeficiency Virus.

Sulfated tocopheryl oligosaccharides and antiviral agents including the

Alkylated oligosaccharides and acetyl derivatives of the same

Growing community of inventors

Chiba, Japan

Nahoko Takahashi