Use of alkyl polyglycosides and/or of O-acylated derivatives...

Details Use of alkyl polyglycosides and/or of O-acylated derivatives... Use of alkyl polyglycosides and/or of O-acylated derivatives...

1996-09-09

2001-03-20

Criares, Theodore J. (Department: 1716)

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

Polymer containing

C424S070100, C514S023000, C514S025000, C514S053000

Reexamination Certificate

active

06203783

ABSTRACT:

The present invention relates to the use in cosmetics or in pharmacy of alkyl polyglycosides and/or of O-acylated derivatives of glucose for treating hair loss.
Hair growth and renewal are mainly determined by the activity of the hair follicles. Their activity is cyclic and essentially entails three phases, namely the anagen phase, the catagen phase and the telogen phase.
The active anagen phase, or growth phase, which lasts for several years during which the hair elongates, is succeeded by a very short and transient catagen phase and a rest phase, termed telogen phase, of a few months.
At the end of the rest period, the hair is shed and another cycle begins again. The head of hair is hence being constantly renewed in human beings and, of the approximately 150,000 hairs of which a head of hair is composed, approximately 10% are at rest at any instant and will hence be replaced in a few months.
In a large number of cases, early hair loss occurs in genetically predisposed subjects, and it affects men in particular. This applies, more especially, to androgenetic or androgenic or alternatively androgeno-genetic alopecia.
This alopecia is essentially due to a disturbance of hair renewal, which leads initially to an acceleration of the frequency of the cycles at the expense of the quality of the hairs, and then of their quantity. There is a gradual depletion of the head of hair through regression of so-called “terminal” hairs at the down stage. Some regions are affected preferentially, in particular the temporal or frontal areas in men, and a diffuse alopecia of the crown is observed in women.
Compositions that enable the effect of androgenetic alopecia to be abolished or reduced and, in particular, hair growth to be induced or stimulated or hair loss to be decreased have been sought for many years in the cosmetic or pharmaceutical industry.
In this connection, compounds such as 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine or Minoxidil as well as its derivatives, as described in U.S. Pat. No. 4,139,619, have already been proposed.
Oligosaccharides containing at least one disaccharide unit consisting of a uronic acid residue and a hexosamine residue have also been proposed. They are described in European Patent Application EP 0,211,610.
The Applicant has just discovered, surprisingly, that alkyl polyglycoside compounds and/or O-acylated derivatives of glucose enabled hair growth to be induced and stimulated and hair loss to be decreased effectively.
The Applicant found, moreover, that the compositions containing these particular compounds displayed good stability on storage and improved cosmetic properties, especially in regard to sheen of the hair and deposition of powder thereon, and did not cause irritation of the scalp even after prolonged contact without rinsing.
A subject of the invention hence consists of the use in cosmetics of alkyl polyglycosides and/or of O-acylated derivatives of glucose for treating hair loss.
Another subject consists of the use of these compounds for the preparation of pharmaceutical compositions based on these particular compounds for the treatment of hair loss.
The subject of the invention is also a process for the cosmetic treatment of the hair and scalp by means of these compounds.
Other subjects will become apparent on reading the description and the examples which follow.
The use according to the invention employs compounds corresponding to the formula (I):
R
1
(C
6
H
10
O
5
)
x
H  (I)
corresponding to the structural formula (II):
in which:
R
1
denotes an alkyl or alkenyl radical having an unbranched or branched C
8
-C
24
chain, or a mixture of such radicals;
x is a number between 1 and 15;
and/or compounds corresponding to the formula (III):
in which R
2
represents a saturated or unsaturated, linear hydrocarbon chain containing from 7 to 19 carbon atoms and R
3
represents hydrogen or a C
1
-C
4
lower alkyl group; with the proviso that the compounds of formula (I) are not used in combination with pyrimidine derivatives.
The alkyl polyglycoside compounds of formula (I) as defined above, used according to the invention, are preferably represented by the products sold by the company HENKEL under the name APG, such as the products APG 300, APG 350, APG 500, APG 550, APG 625, APG base 10-12; the products sold by the company SEPPIC under the names TRITON CG 110 (or ORAMIX CG 110) and TRITON CG 312 (or ORAMIX NS 10); and those sold by the company BASF under the name LUTENSOL GD 70.
The compounds of formula (III) are known compounds, a process for the preparation of which is described below, and they are chosen, in particular, in the group of those in which the acyl residue R
2
—CO— is an octanoyl, decanoyl, dodecanoyl, myristoyl, hexadecanoyl, stearoyl, oleoyl, linoleoyl or linolenoyl residue. By way of examples of compounds of formula (III), 6-O-oleoyl-D-glucose, 6-O-decanoyl-D-glucose, 6-O-dodecanoyl-D-glucose and 6-O-hexadecanoyl-D-glucose may be mentioned.
The general procedure for preparing D-glucose derivatives O-acylated at position 6, of formula (III), is as follows:
The synthesis is carried out using the chosen acid chloride and D-glucose according to the method described by E. REINEFELD et al., “Die Stärke”, no. 6, pages 181-189, 1968.
The compounds according to the invention of formula (I) or (III) may be combined with compounds that further improve their activity with respect to hair regrowth and/or to the halting of hair loss, such as, more especially, the following compounds:
nicotinic acid esters including, more especially, C
1
-C
6
alkyl nicotinates, and in particular methyl, hexyl and benzyl nicotinate, and the like;
steroidal and nonsteroidal anti-inflammatory agents which are well known in the prior art, and especially hydrocortisone, its salts and its derivatives, niflumic acid, and the like;
retinoids such as all-trans-retinoic acid also known as tretinoin, isotretinoin, retinol or vitamin A and its derivatives, for instance the acetate, palmitate or propionate, motretinide, etretinate and zinc all-trans-retinoate;
pyrimidine derivatives such as 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine, also known under the name “minoxidil”, as are described in U.S. Pat. No. 4,139,619, present only for the compounds of the formula (III);
antibacterial agents chosen from macrolides, pyranosides and tetracyclines, and erythromycin in particular;
calcium antagonists such as cinnarizine and diltiazem;
hormones such as estriol or analogs or thyroxine and its salts;
antiandrogens such as oxendolone, spironolactone and diethylstilbestrol;
OH radical trapping agents such as dimethyl sulfoxide.
It is also possible to combine with the compounds of the invention, optionally mixed with the others, compounds such as diazoxide corresponding to 3-methyl-7-chloro-[2H]-1,2,4-benzothiadiazine 1,1-dioxide; spiroxazone or 7-(acetylthio)-4′, 5′-dihydrospiro[4-androstene-17,2′(3′H)-furan]-3-one; phospholipids such as lecithin; linoleic and linolenic acids, salicylic acid and its derivatives described in French Patent 2,581,542, such as salicylic acid derivatives bearing an alkanoyl group having 2 to 12 carbon atoms at position 5 of the benzene ring; hydroxycarboxylic or ketocarboxylic acids and their esters; lactones and their corresponding salts; anthralin; carotenoids; and icosatetraynoic and icosatriynoic acids or their esters and amides.
The compositions according to the invention containing these compounds can take the form of lotions, emulsions, creams or gels, and can be pressurized, where appropriate, as an aerosol. They may be applied, in particular, in treatments employing a composition as is defined above, the application of which is or is not followed by a rinse, or alternatively in the form of a shampoo.
In the nonrinsed compositions, the compounds of formula (I) or the compounds of formula (III) are present in proportions of between 0.1 and 10% by weight relative to the total weight of the composition, and preferably between 0.25 and 5% by weight.
In the compo

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