Flavanonol derivatives and hair-nourishing, hair growing composi

Details Flavanonol derivatives and hair-nourishing, hair growing composi Flavanonol derivatives and hair-nourishing, hair growing composi

1996-09-16

1997-12-30

Dees, Jose' G.

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

Polymer containing

424195, 424405, 549400, 514456, A61K 706, C07D31132

Patent

active

057026912

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP95/02433 filed Nov. 29, 1995.


TECHNICAL FIELD

The present invention relates to flavanonol derivatives and to hair-nourishing and hair-growing compositions containing the derivatives.


BACKGROUND ART

Hitherto, synthetic chemicals and natural extracts performing a variety of actions have been used as pharmaceuticals or medicated cosmetics which are intended to be used for hair nourishing and hair growing. Neither of these chemicals nor extracts exhibits sufficient effects if used in small amounts. Particularly, natural extracts have drawbacks that they give uncomfortable stimulation to portions of application if they are used in large amounts; that inflammation of the skin may be caused when they are used continuously; and that they may not be used in large amounts due to their color and odor.
Moreover, these conventional hair-nourishing and hair-growing agents do not directly act on differentiation and proliferation of hair matrix cells but exhibit their effects through normalizing the conditions of the scalp. Even in cases where they act on hair matrix cells, they do not exhibit satisfactory nourishing and growing effects on human hair.
Accordingly, it is still desired to develop hair-nourishing and hair-growing agents which exhibit remarkable hair-nourishing and hair-growing effects as well as hair loss-preventing effects through acting directly on differentiation and proliferation of hair matrix cells, and which are quite safe when used over long periods.


DISCLOSURE OF THE INVENTION

In view of the foregoing, the present inventors conducted careful studies, and as a result, they found that flavanonol derivatives represented by formula (1) described below act directly on differentiation and proliferation of hair matrix cells to exhibit remarkable hair-nourishing and hair-growing effects, and maintain high levels of safety over long periods of use. The present invention was accomplished based on these findings.
Accordingly, the present invention provides a hair-nourishing and hair-growing agent comprising a flavanonol derivative represented by the following formula (1): ##STR2## wherein R.sup.1 represents an alkyl group, and each of R.sup.2 and R.sup.3 represents a hydrogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, a hydroxyl group, a cyano group, or a halogen atom.
The present invention also provides use of a flavanonol derivative represented by the above-described formula (1) as a hair-nourishing and hair-growing agent.
The present invention further provides a method of nourishing and growing the hair, characterized by administering an effective amount of a flavanonol derivative represented by the above-described formula (1).
Of all the compounds of formula (1), those excepting the compounds in which R.sup.1 is a methyl group and R.sup.2 and R.sup.3 are both hydrogen atoms are novel compounds which have not yet appeared in literature. Therefore, the present invention also provides a flavanonol derivative represented by the following formula (1a): ##STR3## wherein R.sup.1a represents a C1-C12 alkyl group, and each of R.sup.2a and R.sup.3a represents a hydrogen atom, a C1-C12 alkyl group which may be substituted by a halogen atom, a C1-C12 alkoxyl group which may be substituted by a C1-C12 alkoxyl group, a hydroxyl group, a cyano group, or a halogen atom; provided that R.sup.la is not a methyl group when R.sup.2a and R.sup.3a are both hydrogen atoms.


BEST MODE FOR CARRYING OUT THE INVENTION

In the compounds of formula (1), synthesis examples have been reported with respect to each of a compound in which R.sup.2 and R.sup.3 are hydrogen atoms and R.sup.1 is a methyl group, and the other compound in which R.sup.1 is a methyl group, R.sup.2 is a hydrogen atom, and a methoxy group Tetrahedron Lett., 1023, 1967; W. P. Cullen, et al., J. Chem. Soc. (C), 2848, 1971!. However, it is not known as to whether these compounds have hair-nourishing or hair-growing effects.
In the above formula (1) representing the flavan

REFERENCES:
patent: 3689663 (1972-09-01), Kramer et al.
Journal of the Chemical Society, Section C: Organic Chemistry, vol. 17, pp. 2848-2855, 1971, W. P. Cullen et al., "The Algar-Flynn-Oyamada Oxidation of .alpha.-Substituted Chalcones.alpha.".
Tetrahedron Letters, No. 11, pp. 1023-1027, 1967, D.M.X. Donnelly, et al., "Oxidation of .alpha.-Methylchalcones".

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