Anticancer agents, perfumes or foods and drinks

Details Anticancer agents, perfumes or foods and drinks Anticancer agents, perfumes or foods and drinks

2002-07-02

2003-10-28

Carr, Deborah D. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

C554S213000, C514S400000, C514S557000, C514S675000, C514S680000, C514S685000

Reexamination Certificate

active

06639089

ABSTRACT:

TECHNICAL FIELD
The present invention relates to drugs and, particularly, to anticancer agents. More particularly, the present invention relates to an anticancer agents containing, as an active ingredient, at least one compound selected from the group consisting of &ohgr;-hydroxy fatty acids and salts or esters thereof, hydroxy oxo-fatty acids and salts or esters thereof, lactones, macrocyclic ketones, and macrocyclic diesters.
BACKGROUND ART
Many anticancer agents, including bleomycin, Pepleostatin, and Mitomycin (registered trade name), have been developed. However, these agents have strong side effects, such as cytotoxicity, and moreover, in order to exert a satisfactory action of inhibiting metastasis, they must be administered in large quantities, which may prove to be fatal.
Under the circumstances, attention has been given to the development of compounds having decreased side effects. As a result, antitumor agents containing carbon, hydrogen, and oxygen only have been proposed, for example, antitumor agents containing unsaturated fatty acids, such as linoleic acid and oleic acid (disclosed in JP-A-Syouwa62-12716, etc.), ketol-type unsaturated fatty acids (disclosed in JP-A-Heisei5-279252), hydroxylinoleic acid (disclosed in JP-A-Heisei7-291862), and 10-oxo-11(E)-octadecen-13-olide, which is a new macrolide compound (disclosed in JP-A-Heisei6-220037).
However, in these antitumor agents, merely the action of killing tumors is demonstrated, and since known antitumor agents use natural extracts as raw materials, in order to ensure purities necessary for antitumor agents, extremely complex purifying processes must be performed, resulting in production difficulty on an industrial scale.
Accordingly, it is an object of the present invention to provide an anticancer agents which is easily produced, which has an activity of inhibiting cancer metastasis in addition to an activity of killing cancer, and which also has decreased side effects.
DISCLOSURE OF THE INVENTION
“Anticancer agents” in the present invention mean agents which are used for the purpose of killing cancer, inhibiting the metastasis of cancer, preventing the recurrence of cancer, preventing cancer, or the like.
The present inventors have carried out thorough research on substances which can be mass-produced in high purities on an industrial scale, which are highly safe, and which exhibit satisfactory absorption into cells, and found that &ohgr;-hydroxy fatty acids and salts or esters thereof, hydroxy oxo-fatty acids and salts or esters thereof, lactones, macrocyclic ketones, and macrocyclic diesters having specific chemical structures are anticancer agents which have significantly high activities of killing cancer and inhibiting the metastasis of cancer, and thus the present invention has been achieved.
In one aspect of the present invention, the anticancer agents contain, as an active ingredient, at least one compound selected from the group consisting of:
an &ohgr;-hydroxy fatty acid represented by general formula (1) or a salt or ester thereof:
HO—R
1
—COOH  (1)
 wherein R
1
is a straight carbon chain having 10 to 25 carbon atoms, with no or one double bond, where an alkyl or alkylene group having 1 to 4 carbon atoms or a hydroxyl group may be linked to any position as a side chain;
a hydroxy oxo-fatty acid represented by general formula (2) or a salt or ester thereof:
R
2
—COOH  (2)
 wherein R
2
is a saturated straight carbon chain having 9 to 25 carbon atoms, with at least one carbonyl group and at least one hydroxyl group, where an alkyl or alkylene group having 1 to 4 carbon atoms may be linked to any position as a side chain;
a lactone represented by general formula (3):
 wherein R
3
is a carbon chain having 2 to 24 carbon atoms which is saturated or unsaturated by including at least one carbon-carbon double bond in any position, or a carbon chain having 8 to 24 carbon atoms with at least one oxygen atom in any position which is saturated or unsaturated by including at least one carbon-carbon double bond in any position, where an alkyl or alkylene group having 1 to 4 carbon atoms may be linked to any position as a side chain; R
4
is hydrogen, a hydroxyl group, or a carbon chain having 1 to 30 carbon atoms which is saturated or unsaturated by including at least one carbon-carbon double bond in any position, where an alkyl or alkylene group having 1 to 4 carbon atoms may be linked to any position; and the dashed line represents a single bond or a double bond;
a macrocyclic ketone represented by general formula (4):
 wherein R
5
is hydrogen or an alkyl or alkylene group having 1 to 4 carbon atoms; R
6
is a carbon chain having 7 to 17 carbon atoms which is saturated or unsaturated by including at least one carbon-carbon double bond in any position, where an alkyl or alkylene group having 1 to 4 carbon atoms may be linked to any position as a side chain; R
7
is hydrogen or an alkyl group or an alkylene group having 1 to 4 carbon atoms; and the dashed line represents a single bond or a double bond; and
a macrocyclic diester represented by general formula (5)
 wherein R
8
is a carbon chain having 2 to 10 carbon atoms which is saturated or unsaturated by including at least one carbon-carbon double bond in any position, where an alkyl or alkylene group having 1 to 4 carbon atoms may be linked to any position; and R
9
is a carbon chain having 8 to 20 carbon atoms which is saturated or unsaturated by including at least one carbon-carbon double bond in any position.
That is, as described above, the anticancer agents of the present invention contains, as an active ingredient, at least one compound selected from the group consisting of &ohgr;-hydroxy fatty acids and salts or esters thereof, hydroxy oxo-fatty acids and salts or esters thereof, lactones, macrocyclic ketones, and macrocyclic diesters. These compounds used in the present invention can be combined with the existing anticancer agents.
In the meantime, although various methods for making &ohgr;-hydroxy fatty acids are known, since many types of impurities are produced due to various side reactions in all of the methods, in order to highly purify the resultant &ohgr;-hydroxy fatty acids, complex purification processes must be performed. However, as a result of thorough research carried out by the present inventors, it has been found that by opening the ring of the lactone of the present invention by hydrolysis, an &ohgr;-hydroxy fatty acid can be obtained in high purities in a significantly simple way, and thus the present invention has been achieved.
All of the &ohgr;-hydroxy fatty acids and salts or esters thereof, hydroxy oxo-fatty acids and salts or esters thereof, lactones, macrocyclic ketones, and macrocyclic diesters used in the present invention, as compounds themselves, include known compounds, and have been industrially mass-produced mainly as raw materials for perfume compounds and as perfume compounds.
That is, with respect to the compounds used in the present invention, the industrial production methods therefor have been established and they have previously been used for fragrance materials rather than anticancer agents, i.e., they are readily available compounds with high purities.
As the &ohgr;-hydroxy fatty acid or a salt or ester thereof used in the present invention, any compound represented by the following general formula (1) may be used:
HO—R
1
—COOH  (1)
wherein R
1
is a straight carbon chain having 10 to 25 carbon atoms, with no or one double bond, where an alkyl or alkylene group having 1 to 4 carbon atoms or a hydroxyl group may be linked to any position as a side chain. Preferably, R
1
is a straight carbon chain which is saturated or which has one double bond, in which a hydroxyl group is linked to the &ohgr; position. Preferred examples of &ohgr;-hydroxy fatty acids include 12-hydroxydodecanoic acid, 14-hydroxytetradodecanoic acid, 15-hydroxypentadecanoic acid, 16-hydroxyhexadecanoic acid, 17-hydroxyheptadecanoic acid, 18-hydroxyoctadecanoic acid, 15-hydroxy-11-pen

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