Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Peptide containing doai
Patent
1991-12-13
1993-08-03
Lee, Lester L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Peptide containing doai
514 19, 530331, C07K 506
Patent
active
052329135
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to an antihepatopathic composition containing a novel and useful glutathione-S-lower fatty acid derivative.
BACKGROUND ART
There are known several glutathione-S-lower fatty acid derivatives. Among them, S-(2-carboxypropyl)glutathione has been isolated from onion and garlic (Virtanen and Matikkala, Hoppe-Seylers Z. Physiol. Chem., Bd 322, pages 8-20, 1960; Suzuki et al., Chem. Pharm. Bull., Vol. 9, pages 77-78, 1961) but there is little information on its pharmacologic activity.
The inventors of the present invention previously found that glutathione-S-succinic acid derivatives have platelet aggregation-inhibitory, antiinflammatory, antiallergic, antitumoral and hepatic impairment-protective activities (Japanese Kokai Patent Application No. 63-8337 and Japanese Patent Application No. 1-79956, No. 1-183484, No. 1-256370 and No. 2-36745).
In search of still more pharmacologically active compounds, the inventors of the present invention synthesized a variety of novel glutathione derivatives and screened them, as well as said S-(2-carboxypropyl)glutathione, for their pharmacologic activities. As a consequence, they found that S-(2-carboxypropyl)glutathione and a series of compounds which can be synthesized by reacting glutathione or an ester thereof with an .alpha., .beta.-unsaturated fatty acid, such as acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, etc., or an .alpha. (or .beta.)-halogenated organic monocarboxylic acid, such as monochloroacetic acid, or an ester or amide thereof have excellent antihepatopathic efficacy. The present invention has been attained based on this finding.
DISCLOSURE OF THE INVENTION
The present invention relates to an antihepatopathic composition comprising a compound of the formula ##STR2## wherein R.sub.1 and R.sub.3 are the same or different and respectively mean a hydrogen atom or a lower alkyl group which may be substituted; R.sub.4 is a hydroxyl group, a lower alkoxy group which may be substituted or an amino group which may be substituted; n means 0 or 1 and when n=1, R.sub.2 is a hydrogen atom, a lower alkyl group which may be substituted or a phenyl group which may be substituted or a salt thereof as an active ingredient.
Where R.sub.1, R.sub.3 in the above formula means a lower alkyl group, such alkyl group preferably has 1 to 10 carbon atoms. This alkyl group may be straight-chain, branched or cyclic or contain a cyclic moiety. Thus, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, 1-ethylpropyl, isopentyl and benzyl may be mentioned by way of example.
Referring, further, to the above formula, where n is equal to 1, R.sub.2 is a hydrogen atom, a lower alkyl group or a pheyl group. The lower alkyl group is as previously defined, and the phenyl group may be substituted with an alkyl group and so on.
Further in the formula, R.sub.4 is a hydroxyl group, a lower alkoxy group or an amino group. The lower alkoxy group includes, among others, methoxy, ethoxy, propoxy, isopropoxy, n-pentyloxy, isopentyloxy, tert-pentyloxy, n-pentyloxy, isopentyloxy, tert-pentyloxy, neopentyloxy, 2-methylbutoxy, 1,2-dimethylpropoxy, 1-ethylpropoxy and so on. The lower alkoxy group may have a hydroxyl group or a cyclic group such as pehnyl. The hydrogen atom or atoms of said amino group may be substituted by, for example, alkyl.
In the antihepatopathic composition of the invention, the above compound can occur as the free acid or as a pharmaceutically acceptable salt thereof, for instance an alkali metal salt thereof, e.g. the sodium salt, potassium salt, etc., or an alkaline earth metal salt, e.g. the calcium salt, magnesium salt and so on. Regarding the salt, any or all of the carboxyl functions available in the compound may have been converted to such salt or salts. Any of these salts can be used advantageously in the manufacture of the antihepatopathic composition of the present invention.
This antihepatopathic composition effectively inhibits the onset of acute and chronic hepatic disor
REFERENCES:
patent: 4879370 (1989-11-01), Meister
patent: 4927808 (1990-05-01), Kitahara et al.
patent: 5081149 (1992-01-01), Ohmori et al.
patent: 5093478 (1992-03-01), Griffith et al.
patent: 5102871 (1992-04-01), Furukawa et al.
Virtanen et al., Hoppe-Seyler's Z. Physiol. Chem., Bd. 322, pp. 8-20, 1960.
Suzuki et al., Chem. Pharm. Bull., vol. 9, pp. 77-78.
Ogata Kazumi
Ohmori Shinji
Sakaue Takahiro
Lee Lester L.
Senju Pharmaceutical Co. Ltd.
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