Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Patent
1994-11-09
1997-07-08
Conrad, Joseph
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
514568, 514622, 560 43, 560 61, 562433, 562471, 564163, 564167, 564170, 564176, 564177, A61K 31235, A61K 3119, A61K 31165
Patent
active
056461844
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This application is a 371 of PCT/JP94/00477 filed Mar. 25, 1994.
This invention relates to a preparation for external application to the skin containing a benzoic acid derivative having sebaceous secretion inhibitory activity with high safety for human body and to novel benzoic acid derivatives.
BACKGROUND OF THE INVENTION
Known sebaceous secretion inhibiting agents include anti-male sex hormone agents, vitamin A acid, royal jelly acid [Nichihi Kaishi, Vol. 98, No. 4, pp. 469-475 (1988)], and p-hydroxybenzoic acid derivatives (Japanese Patent Public Disclosure No. 153616/89).
The anti-male sex hormone agent is a substance relative to hormone metabolism, and vitamin A acid also has a hormone-like action. Exerting their action on not only sebaceous glands but other organs, these agents give rise to a great problem of systemic side effects rather than producing topical effects. Royal jelly acid and the conventional p-hydroxybenzoic acid derivatives were insufficient in their effects.
Accordingly, a primary object of the present invention is to provide a preparation for external application to the skin which exhibits sufficient inhibitory activity on sebaceous secretion and is of high safety for human body causing no side effects.
A secondary object of the present invention is to provide a novel benzoic acid derivative which is useful as an active ingredient of the above-mentioned preparation.
DISCLOSURE OF THE INVENTION
The present inventors have conducted extensive investigations into sebaceous secretion inhibiting agents by which the above objects of the present invention can be accomplished. As a result, they have found that specific benzoic acid derivatives have a high sebaceous secretion inhibitory effect and also discovered novel benzoic acid derivatives. The present invention has been completed based on these findings.
The present invention provides a preparation for external application to the skin characterized by containing at least one of benzoic acid derivatives represented by general formula (I) shown below or pharmacologically acceptable salts thereof as an active ingredient: ##STR3## wherein R.sup.1 represents --OH, --OR.sup.3 or --NHR.sup.3 ; R.sup.2 represents a hydrogen atom, a lower alkyl group or a lower acyl group; R represents --O--R.sup.4 or ##STR4## R.sup.3 represents an alkyl group, an alkenyl group or a hydroxyalkyl group; R.sup.4 represents a straight-chain or branched, saturated or mono-unsaturated alkyl group or cycloalkylalkyl group having from 4 to 10 carbon atoms; X represents --O-- or --NH--; and n represents 1 or 2.
The present invention also provides a novel benzoic acid derivative represented by formula (II) shown below and a pharmacologically acceptable salt thereof: ##STR5## wherein R.sup.5 represents --OH, --OR.sup.8 or --NHR.sup.8 ; R.sup.6 represents a hydrogen atom, a lower alkyl group or a lower acyl group; R.sup.7 represents a branched saturated or mono-unsaturated alkyl group or cycloalkylalkyl group having from 6 to 10 carbon atoms; and R.sup.8 represents an alkyl group or a hydroxyalkyl group.
The present invention further provides a novel benzoic acid derivative represented by formula (III) shown below and a pharmacologically acceptable salt thereof: ##STR6## wherein R.sup.9 represents --OH, --OR.sup.11 or --NHR.sup.11 ; R.sup.10 represents a hydrogen atom, a lower alkyl group or a lower acyl group; R.sup.11 represents an alkyl group, an alkenyl group or a hydroxyalkyl group; X represents --O-- or --NH--; and n represents 1 or 2.
BEST EMBODIMENT FOR CARRYING OUT THE INVENTION
The preparation for external application to the skin according to the present invention will be illustrated in more detail.
The benzoic acid derivative which can be used as an active ingredient of the preparation is represented by formula (I).
In formula (I), the lower alkyl group as represented by R.sup.2 preferably includes those having 1 to 5 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, a butyl group, and a pentyl group. The l
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Maeda, T. et al., Effects of royal jelly and 10-hydroxydecenoic acid on the sebaceous glands of hamster ear, Hifuka Gakkai Zasshi 1988, 98 (4), pp. 469-475 (Japan) and English Abstract.
Hori Kimihiko
Kitahara Takashi
Koizumi Keiko
Sakaguchi Akira
Sato Noriko
Conrad Joseph
Kao Corporation
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