Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Reexamination Certificate
1999-07-16
2001-01-23
Killos, Paul J. (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
Reexamination Certificate
active
06177592
ABSTRACT:
TECHNICAL FIELD
The present invention relates to the compounds useful in the field of pharmaceuticals having a physiological activity such as anticancer action and also relates to a method for the manufacture of said compounds.
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 can be hardly said that such a drug therapy has been completely established already.
Among those agents, prostaglandin A and J having an &agr;, &bgr;-unsaturated carbonyl in a five-membered 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 the compounds having a physiological action such as anticancer action and to offer a method for the manufacture of said compounds and pharmaceuticals containing said compounds.
MEANS TO SOLVE THE PROBLEMS
The present inventors have conducted an intensive study for achieving said object and have found that the compound represented by the formula [I] (hereinafter, referred to as “compound of the present invention”) is produced by the reaction of 4,5-dihydroxy-2-cyclopenten-1-one (hereinafter, referred to as just “cyclopentenone”) represented by the formula [IV] with a compound containing an SH group and that said compound of the present invention has various strong physiological activity and is useful for therapy and/or prevention of diseases being sensitive to said compound whereby the present invention has been achieved.
The present invention will be summarized to be as follows. Thus, the first feature of the present invention relates to a compound represented by the following formula [I] or an optically active substance or a salt thereof.
(In the formula, a bond shown by a dotted line in the five-membered ring means that said five-membered ring may be any of a cyclopentene ring having a double bond and a cyclopentane ring where said bond is saturated and, in the case of a cyclopentene ring, X is OH, Y is ═O and Z is H while, in the case of a cyclopentane ring, X is ═O, Y is OH and Z is OH. R is a residue after removal of an SH group from the SH-containing compound.)
An embodiment of the first feature of the present invention is a compound represented by the following formula [II] or an optically active substance or a salt thereof.
(In the formula, R is a residue after removing an SH group from the SH-containing compound.)
Another embodiment of the first feature of the present invention is a compound represented by the following formula [III] or an optically active substance or a salt thereof.
(In the formula, R is a residue after removing an SH group from the SE-containing compound.) The second feature of the present invention is a method for the manufacture of the compound represented by the formula [I] or an optically active substance or a salt thereof in the first feature of the present invention, characterized in that, a compound selected from 4,5-dihydroxy-2-cyclopenten-1-one represented by the following formula [IV] or an optically active substance or a salt thereof is made to react with a compound containing an SH group.
In a preferred embodiment of the first and the second features of the present invention, the compound containing an SH group is an SH-containing amino acid or a derivative thereof.
The third feature of the present invention is a pharmaceutical agent which is characterized in containing at least one compound selected from a compound represented by the formula [I] in the first feature of the present invention or an optically active substance or a salt thereof as an effective component.
In a preferred embodiment of the third feature of the present invention, said pharmaceutical agent is a biophylactic agent (such as immunomodulator, antiallergic agent or antirheumatic agent), remedy for diabetes mellitus, anticancer agent, apoptosis inducer or an agent against pathogenic microbes (such as antiviral agent or antibacterial agent).
REFERENCES:
patent: 4180672 (1979-12-01), Kurozumi et al.
patent: 53-111037 (1978-09-01), None
Chono Hideto
Enoki Tatsuji
Hagiya Michio
Ikai Katsushige
Kato Ikunoshin
Killos Paul J.
Rhodes & Mason PLLC
Takara Shuzo Co. Ltd.
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