Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Patent
1995-04-21
1998-12-15
Fonda, Kathleen K.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
536 41, 536 179, 536 187, 536 185, 536 186, 536 53, 536124, 424520, A61K 3170, C07H 1500
Patent
active
058497161
DESCRIPTION:
BRIEF SUMMARY
This application is the U.S. national stage entry under 35 U.S.C. 371 of PCT/JP93/01523, filed Oct. 22, 1993.
TECHNICAL FIELD
The present invention relates to a novel sphingoglycolipid which is useful as an anti-tumor agent and an immunostimulating agent in the field of medicine.
BACKGROUND ART
The sphingoglycolipid is a complex glycolipid comprising as a lipid component a ceramide which is formed by an amide bond of a fatty acid with a long chain base, a monosaccharide or an oligosaccharide being bonded to the primary alcohol of the ceramide via glycoside bond. The review of the sphigoglycolipid including the history of its discovery, the components of the complex glycolipid and its preparation methods has been described in SHIN-SEIKAGAKU JIKKEN KOZA NO. 4, LIPIDS III, GLYCOLIPIDS, 1990, TOKYO KAGAKU DOJIN.
A sphingoglycolipid which is recognized to have an anti-tumor or immunostimulating effects includes sphingoglycolipids which have been extracted and isolated from a poriferan, Agelas mauritianus, by the present inventors (Japanese Patent Laid-Open Publication Nos. 303314/1990, 244385/1991 and 244384/1991, and PCT/JP92/00561).
In addition to the sphingoglycolipids described above, there has been described only one sphingoglycolipid in Japanese Patent Laid-Open Publication No. 93562/1989 to the best of the knowledge of the present inventors. The sphingoglycolipid however must be administered at a very large amount of 0.5-2 mg/mouse, and thus has not been put to the practical use.
A variety of anti-tumor agents and immunostimulating agents have hitherto been developed, but none of these agents were satisfactory from the aspect of their effects or side-effects. The object of the present invention is to provide an anti-tumor and immunostimulating agent which is effective at a small dose and has little side-effect.
DISCLOSURE OF THE INVENTION
The present inventors have created a process for synthesizing an aldopyranosyl- or aldofuranosyl-sphingoglycolipid and found that the compound exhibits an anti-tumor activity and an immunostimulating effect. Thus, they have accomplished the present invention on the basis of this information.
That is, the compound according to the present invention is the sphingoglycolipid represented by the following formula (I): ##STR2## wherein X denotes an integer from 10 to 24, Y denotes an integer from 9 to 13, N-acetylaminohexosyl or a halide thereof or a sialic acid, or a galactosyl or glucosyl group, or a galactosyl or glucosyl group, the two carbon atoms to which R.sub.6 and R.sub.7 are attached, represents H, and the following compounds (i)-(viii): 1-(2-acetamino-2-deoxy-.alpha.-D-galactopyranosyloxy)-2-octadecanoylamino- 3-octadecanol; 1-(2-acetamino-2-deoxy-.alpha.-D-glucopyranosyloxy)-2-octadecanoylamino-3- octadecanol; yranosyloxy!-2-octadecanoylamino-3-octadecanol; yranosyloxy!-2-octadecanoylamino-4-octadecen-3-ol; (2S,3R,4E)-1-.beta.-D-glucopyranosyloxy-2-hexadecanoylamino-4-eicosen-3-ol ; (2S,3R,4E)-1-.beta.-D-glucopyranosyloxy-2-hexadecanoylamino-4-octadecen-3- ol; 5-acetamido-3,5-dideoxy-D-glycero-.beta.-D-galacto-2-nonulopyranosylonate) -2-tetracosanamido-4-octadecene-1,3-diol; and -glycero-.alpha.-D-galacto-2-nonulopyranosylonate)-2-tetracosanamido-4-oct adecene-1,3-diol.
The present invention also relates to the use of the compound.
That is to say, the anti-tumor agent and the immunostimulating agent according to the present invention contain the compound represented by the formula (I) as an effective ingredient.
BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 shows a reaction scheme of the synthetic route A,
FIG. 2 shows a reaction scheme of the synthetic route B,
FIGS. 3(a) and (b) show a reaction scheme of the synthetic route C, and
FIGS. 4(a), (b) and (c) show a reaction scheme of the synthetic route D.
BEST MODE FOR CARRYING OUT THE INVENTION
The sphingoglycolipid according to the present invention is, as described above, the compound represented by the formula (I) and has the structure formed by the glycosyl bond of a ceramide with a monosaccharide (a
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Akimoto Koji
Koezuka Yasuhiko
Fonda Kathleen K.
Kirin Beer Kabushiki Kaisha
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