Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Patent
1988-01-07
1991-06-11
Griffin, Ronald W.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
536 5, 536 179, 536 187, 536 53, 536 553, A61K 31705, C07H 1524
Patent
active
050232398
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to sialosyl cholesterol, in particular sialosyl cholesterol which is useful as an agent for curing various diseases derived from lesions of peripheral nerves and central nerves.
BACKGROUND OF THE INVENTION
So far, it has been known in the art that sialic acid is present in many animal bodies and on the cell surface of several bacteria as a sialylated molecular complex, for example, glycoprotein, glycolipid, oligosaccharide or polysaccharide.
Recently, this compound has been thought to be important medicinally and pharmaceutically for nerve function, cancer, inflamation, immunity, viral infection, differentiation, hormone receptor, and others. Further, much attention has been paid to this compound as a peculiar active substance located on the cell surface. However, the role of sialic acid in the sialylated molecular complex has not yet been ascertained.
Furthermore, this compound has been studied by many natural organic chemists and many kinds of derivatives thereof have been obtained. However, no derivatives having a remarkable physiological activity have been obtained yet.
Further, the average span of human life has been indeed extended by various improvements in medical treatment of malignant tumor of hematopoietic organ, many kinds of cancers, and collagen disease. However, these improvements have inevitably increased use of medicines such as adrenal cortical hormone, immunosuppressant, etc. Therefore, a number of undersirable side effects such as decrease in immunological competence have arisen.
The present inventors have paid special attention to sialic acid which is a bio-inherent component and have made intensive studies on immuno-controlling agents which have substantially no side effects and exhibit a controlling activity for immunological surveillance and are obtained by chemically modifying sialic acid. As a result, the present inventors have prepared sialosyl cholesterol which is useful as a neuropathy remedy. This is based on the finding that the present sialosyl cholesterol promotes growth of the neurites of neuroblastoma cells derived from mouse (Neuro 2a), when the activity of the sialosyl cholesterol is examined by adding it to the culture of Neuro 2a.
The object of the present invention is to provide a new sialosyl cholesterol.
Another object of the present invention is to provide a new process for producing sialosyl cholesterol.
Another object of the present invention is to a new neuropathy remedy.
Incidentally, since the present sialosyl cholesterol is present in an Na salt form, the cholesterol has an excellent water-solubility and makes the utility of the cholesterol wider.
DISCLOSURE OF THE INVENTION
The present invention relates to the compound having the following general formula (4): ##STR1## or the formula (5): ##STR2##
The present invention also relates to a process for producing the compound (4) or (5), which comprising reacting a compound (1) having a general formula (1): ##STR3## with cholesterol, to produce a compound having a general formula (2): ##STR4## or the formula (3): ##STR5## and then hydrolyzing the compound (2) or (3).
Further, the present invention relates to a neuropathy remedy containing the compound (4) or (5).
The present invention will be explained in detail below
First, a process for producing the compound (4) or (5) will be summarized by the following scheme: ##STR6##
The compound (1) to be used in the present invention is a known compound, and is commercially available.
In the above reaction, the compound (1) is reacted with cholesterol in the presence of a Koenigs-Knorr catalyst at about 20.degree. to 25.degree. C. under a normal pressure for about 1 to 7 days. In this case, cholesterol is reacted with the compound (1) at a molar ratio of about one to 5 moles of cholesterol to 1 mole of the compound (1).
The catalyst covers mercuric bromide, mercuric cyanide, silver perchlorate, silver trifluoromethanesulfonate, silver trifluoroacetate, and others. The catalyst is used in an amount of about 1.0 to 1.2
REFERENCES:
patent: 4461762 (1984-07-01), Malinow
patent: 4691012 (1987-09-01), Ogura et al.
patent: 4707469 (1987-11-01), Della Valle et al.
patent: 4797477 (1989-01-01), Yoshimura et al.
The Merck Manual; 15th Edition Berkow et al. Eds. pp. 1443-1445, (1987).
Kato et al; Brain Research 438:277-285 (1988).
Ito et al; Brain Research 481:335-343 (1989).
Kogura et al; "Summary of Proceedings of the 105th Annual Seminar of the Japanese Academy of Medicine", p. 633, Abstract 5Q9-8 (3-1985).
Chemistry Letters, No. 9, 1986, pp. 1449-1452, The Chemical Society of Japan, Tokyo, "A Stereospecific Synthesis of . . . ", Okamoto et al.
Furuhata Kimio
Ito Masayoshi
Nagai Yoshitaka
Ogura Haruo
Sato Shingo
Carson Nancy S.
Griffin Ronald W.
Mect Corporation
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