Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ketone doai
Patent
1999-02-02
2000-07-11
Reamer, James H.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ketone doai
568346, 568379, A61K 3112
Patent
active
060874015
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to cyclopetenones having a physiological activity such as anticancer action and having a high safety and, more particularly, it relates to manufacturing methods of said compounds and also to pharmaceuticals containing said compounds as effective components. The present invention also relates to a series of inventions useful in the fields of food, beverage, etc.
PRIOR ART
Pharmaceuticals which have been used in clinical therapy include many agents such as anticancer agents, antibiotic substances, immunopotentiators, immunomodulators, etc. (such as alkylating agents, antimetabolites and plant alkaloids) but it is hardly said that such a drug therapy has been completely established already.
Among those agents, prostaglandin A and J having a cyclopentenone ring among the prostaglandins derived from natural substances have been reported to have a possibility of being used as highly-safe anticancer agents due to their inhibition of DNA synthesis and various derivatives of them have been synthesized (refer to the Japanese Laid-Open Patent Publication Sho-62/96438).
PROBLEMS TO BE SOLVED BY THE INVENTION
An object of the present invention is to develop highly-safe cyclopentenone compounds having physiological actions such as an anticancer action and to offer manufacturing methods for said compounds, pharmaceuticals having said compounds as effective components and food or beverage containing said compounds. Another object of the present invention is to offer a method of use of said compounds and also other compounds, etc. which are related to said compounds.
MEANS TO SOLVE THE PROBLEMS
The present invention will be summarized to be as follows. Thus, the first feature of the present invention relates to a method of manufacturing 4,5-dihydroxy-2-cyclopenten-1-one represented by the following formula [1] which is characterized in that at least one substance selected from the following (a), (b) and (c) is heated. derivative(s); and acid and/or uronic acid derivative(s). ##STR2##
The second feature of the present invention relates to a method of manufacturing 4,5-dihydroxy-2-cyclopenten-1-one which is characterized in that at least one substance selected from the following (a), (b) and (c) is heated and the 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] is collected from the above heat-treated product. derivative(s); and acid and/or uronic acid derivative(s).
The third feature of the present invention relates to a method of manufacturing an optically active compound of 4,5-dihydroxy-2-cyclopenten-1-one which is characterized in including the following steps. (b) and (c) is heated to produce 4,5-dihydroxy- 2-cyclopenten-1-one. derivative(s), and acid and/or uronic acid derivative(s); from the resulting heat-treated product; and optical resolution.
The fourth feature of the present invention relates to (-)-4,5-dihydroxy-2-cyclopenten-1-one having an optical rotation [.alpha]sub.D.sup.20 -105.degree. (c=0.30, ethanol).
The fifth feature of the present invention relates to (+)-4,5-dihydroxy-2-cyclopenten-1-one having an optical rotation [.alpha]sub.D.sup.20 +104.degree. (c=0.53, ethanol).
The sixth feature of the present invention relates to an anticancer agent which is characterized in containing 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] and/or an optically active compound thereof.
The seventh feature of the present invention relates to a cancer cell differentiation inducer which is characterized in containing 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] and/or an optically active compound thereof.
The eighth feature of the present invention relates to an apoptosis inducer which is characterized in containing 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] and/or an optically active compound thereof.
The ninth feature of the present invention relates to an antibacterial agent which is characterized in containing 4,5-dihydroxy-2-cyclopenten-1-one represented by the formula [1] and/or an opti
REFERENCES:
patent: 5116869 (1992-05-01), Sugiura et al.
patent: 5149711 (1992-09-01), Hazato et al.
Ahmad et al., "The formation of reductic acid from pentoses or hexuronic acids", Carbohydr. Res. (1993), 247, pp. 217-222.
Cocu et al., "Cyclitols. XLIV. Synthesis of cycloses derived from cyclopentane", Helv. Chim. Acta (1972), 55(8), pp. 2838-2844.
Langenfeld, et al., "D-Moenuronic acid (4-methyl-D-glucuronic acid), a new building block for the antibiotic meonomycin A", Tetrahedron Lett. (1978), (21), pp. 1833-1836.
Enoki Tatsuji
Ikai Katsushige
Kato Ikunoshin
Kobayashi Eiji
Koyama Nobuto
Reamer James H.
Takara Shuzo Co. Ltd.
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