Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ketone doai
Patent
1999-09-29
2000-12-26
Padmanabhan, Sreeni
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ketone doai
514729, 426592, 426658, 568338, 568379, 568361, 568838, A61K 31122, C07C 49297
Patent
active
061660914
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to the hydroxycyclopentanone compounds useful in the field of pharmaceutical agents, food or beverage having a physiological activity such as anticancer action and also relates to manufacturing methods and uses thereof.
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 cyclopentanone compounds having physiological actions such as an anticancer action and to offer manufacturing methods for said compounds, pharmaceutical agents and food or beverage containing said compounds.
MEANS TO SOLVE THE PROBLEMS
The present inventors have found that a compound which is 2,3,4-trihydroxy-2-cyclopentanone (hereinafter, just referred to as "hydroxycyclopentanone") represented by a formula [I] is produced in a heat-treated products of at least one substance selected from uronic acid, uronic acid derivative(s), a saccharide compound containing uronic acid and/or uronic acid derivative(s) therein and a substance which contains a saccharide compound containing uronic acid and/or uronic acid derivative(s) therein and that said compound which is isolated from the heat-treated products has a physiological activity such as a anticancer action whereupon the present invention has been achieved.
Now the present invention will be summarized to be as follows. Thus, the first feature of the present invention relates to 2,3,4-trihydroxycyclopentanone represented by the following formula [I], its optically active substance or salt thereof. ##STR2##
The second feature of the present invention relates to a method for the manufacture of 2,3,4-trihydroxycyclopentanone represented by the formula [I], its optically active substance or salt thereof characterized in comprising the following steps. (b) and (c) is heated to produce 2,3,4-trihydroxycyclopentanone derivative(s) and/or uronic acid derivative(s) heat-treated product if necessary.
The third feature of the present invention relates to a method for the manufacture of 2,3,4-trihydroxycyclopentanone represented by the formula [I], its optically active substance or salt thereof characterized in comprising a step where 4,5-dihtydroxy-2-cyclopenten-1-one represented by the following formula [II] is converted to 2,3,4-trihydroxycyclopentanone represented by the formula [I]. ##STR3##
The fourth feature of the present invention relates to a pharmaceutical agent containing at least one compound selected from 2,3,4-trihydroxycyclopentanone, its optically active substance or salt thereof according to the first feature of the present invention as an effective component.
The fifth feature of the present invention relates to food or beverage containing at least one compound selected from 2,3,4-trihydroxycyclopentanone, its optically active substance or salt thereof according to the first feature of the present invention.
BRIEF EXPLANATION OF THE DRAWINGS
FIG. 1 shows the relation between the retention time and the output of the differential refractometer.
FIG. 2 shows a .sup.1 H-NMR spectrum of a mixture of cyclopentenone and hydroxycyclopentanone.
FIG. 3 shows a .sup.13 C-NMR spectrum of a mixture of cyclopentenone and hydroxycyclopentanone.
FIG. 4 shows a gas chromatogram of a mixture of trimethylsilylated cyclopentenone and hydroxycyclopentanone.
FIG. 5 shows a mass spectrum of the peak (1) of
REFERENCES:
patent: 3982996 (1976-09-01), Daum et al.
J. Elliott et al., Tetrahedron Letters, 24(9), 965-968 (1983).
Enoki Tatsuji
Ikai Katsushige
Kato Ikunoshin
Kojima Kaoru
Koyama Nobuto
Padmanabhan Sreeni
Takara Shuzo Co. Ltd.
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