Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1985-06-17
1987-11-03
Daus, Donald G.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
544313, A61K 3150, C07D23954
Patent
active
047043938
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to a 5-fluorouracil derivative and to medicinal preparations containing the same. More particularly, this invention relates to a 5-fluorouracil derivative as a novel compound and platelet aggregation inhibitor and an anticancer chemotherapeutic agent containing the same.
BACKGROUND ART
.alpha.-Linolenic acid and .gamma.-linolenic acid are essential fatty acids which are contained in vegetable oils and are known to possess a function of inhibiting platelet aggregation. In contrast, 5,8,11,14,15-eicosapentaenoic acid and 4,7,10,13,16,19-docosahexaenoic acid are essential fatty acids which are contained in fish oils and are known similarly to possess a function of inhibiting platelet aggregation. The functions which these fatty acids exhibit in inhibiting platelet aggregation, however, are not sufficient.
Incidentally, 5-fluorouracil is used clinically as a chemotherapeutic agent. This compound, however, has the disadvantage that because of its high toxicity, it has its effective concentration in blood only within a narrow range. For the purpose of eliminating this disadvance of 5-fluorouracil, 1,(2-acyloxyalkyl)-5-fluorouracil (Japanese Patent Laid-open No. SHO 51(1976)-98,280), a carboxylic acid derivative of 5-fluorouracil (Japanese Patent Laid-open No. SHO 58(1983)-77,871), etc. have been proposed.
These 5-fluorouracil derivatives, however, have virtually no function of inhibiting platelet aggregation and, worse still, have not been fully stabilized with respect to toxicity.
An object of this invention, therefore, is to provide a novel 5-fluorouracil derivative and medicinal preparations containing the same.
Another object of this invention is to provide a 5-fluorouracil derivative as a novel compound and a platelet aggregation inhibitor and an anticancer chemotherapeutic agent containing the same.
DISCLOSURE OF INVENTION
The objects described above are attained by a 5-fluorouracil derivative represented by the general formula I: ##STR2## wherein R denotes an acyl group derived from an unsaturated higher fatty acid selected from the group consisting of triene higher fatty acids, pentaene higher fatty acids, and hexaene higher fatty acids.
The objects are also attained by a platelet aggregation inhibitor which contains a 5-fluorouracil derivative represented by the general formula I as an effective component.
Further, the aforementioned objects are attained by a chemotherapeutic agent which contains a 5-fluorouracil derivative represented by the general formula I as an effective component.
The same objects are further attained by a medicinal composition comprising a 5-fluorouracil derivative represented by the general formula I and a pharmaceutically acceptable carrier or diluent.
BEST MODE OF CARRYING OUT THE INVENTION
The 5-fluorouracil derivative of the present invention is a compound which is represented by the aforementioned general formula I. In the general formula I, R denotes an acyl group derived from an unsaturated higher fatty acid having 16 to 22, preferably 18 to 22, carbon atoms. Of the acyl groups answering the definition, typical are those derived from .alpha.-linolenic acid, .gamma.-linolenic acid, 5,8,11,14,17-eicosapentaenoic acid, and 4,7,10,13,16,19-docosahexaenoic acid.
The 5-fluorouracil derivative represented by the general formula I is obtained by subjecting 5-fluorouracil to condensation with a compound represented by the general formula II, CClCH.sub.2 OR, wherein R has the same meaning as defined above, in the presence of a base. The proportion of the compound represented by the general formula II to 1 mol of 5-fluorouracil is in the range of 1 to 3 mols, preferably 1.1 to 2 mols.
Examples of the base advantageously used in the condensation include tertiary amines such as trimethylamine, triethylamine, triisopropylamine, tributylamines, and dimethylamino-pyridine. This base is used in an amount of 1 to 4 mols, preferably 1.2 to 2.5 mols, per mol of the 5-fluorouracil. The reaction is carried out desirably in an organic solvent suc
REFERENCES:
patent: 4267326 (1981-05-01), Ozaki et al.
Katayama Hajime
Takahashi Keiko
Wakabayashi Toshio
Daus Donald G.
Shen Cecilia
Terumo Kabushiki Kaisha
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