Cyclodextrin derivatives

Details Cyclodextrin derivatives Cyclodextrin derivatives

1997-12-01

2000-04-04

Kunz, Gary L.

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Cosmetic, antiperspirant, dentifrice

424 701, 514 58, 536103, 536124, A61K 600, A61K 700, A61K 31715, C08B 3700

Patent

active

060458127

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to novel cyclodextrin derivatives, to a process for their preparation and to their use in cosmetics.
Cyclodextrins are oligosaccharides of formula: ##STR1## in which x may be a number equal to 4 (which corresponds to .alpha.-cyclodextrin), 5 (.beta.-cyclodextrin) or 6 (.gamma.-cyclodextrin).
Cyclodextrins are compounds that are well known, in particular for their ability to form inclusion complexes with active substances.
Moreover, the possibility of substituting one or more hydroxyl groups of cyclodextrins in order to graft active substances has been studied. Thus the article by Berger, Journal of Organic Chemistry, 56, pages 3514-3520, 1991, describes .beta.-cyclodextrins grafted with a single graft of m,m'-disulphonylbenzophenone. The article by Tabushi in Tetrahedron Letters No. 29, pages 2503-2506, 1977, describes .beta.-cyclodextrins grafted with a benzophenone graft via an ester linkage.
However, these grafted compounds bear few active grafts, which limits their activity and their efficacy.
After various studies on cyclodextrins, the Applicant has observed, surprisingly, that it is possible to obtain cyclodextrins having screening and/or antioxidant activity, with a higher level of grafting, thereby making it possible to improve the activity and the efficacy of these compounds.
The subject of the present invention is thus novel cyclodextrin derivatives corresponding to the general formula (I) below: .gamma.-cyclodextrin without the hydroxyl groups, cyclodextrin, in which R.sub.1 represents a radical of formula (II), (III), (IV), (V) or (VI) below: ##STR2## or a mixture thereof, in which formulae R.sub.4, R.sub.6 and R.sub.7 represent a hydrogen atom or a C.sub.1 -C.sub.6 alkyl radical or a C.sub.1 -C.sub.12 alkoxy radical, integer equal to 0 or 1, -C.sub.4 alkoxy radical, s is an integer ranging from 0 to 4, cyclodextrin, in which R.sub.2 represents a linear or branched C.sub.1 -C.sub.4 alkyl radical or a C.sub.2 -C.sub.4 hydroxyalkyl radical, it being possible for the hydrogen of the hydroxyl group of the said hydroxyalkyl radical to be substituted with another C.sub.1 -C.sub.4 hydroxyalkyl group or with a radical R.sub.1 or a mixture thereof, groups OR.sub.1 attached directly to the basic skeleton of the cyclodextrin and is a statistical value other than 0, skeleton of the cyclodextrin and is a statistical value other than 0, on whether CD is the basic skeleton of .alpha.-, .beta.- or .gamma.-cyclodextrin respectively.
The compounds of formula (I) bearing radicals of formula (II) to (V) are active in screening out solar radiation and those bearing a radical of formula (VI) have antioxidant activity. The compounds of formula (I) bearing both at least one radical of formula (II) to (V) and at least one radical of formula (VI) have screening and antioxidant activity.
R.sub.2 preferably denotes a methyl or hydroxypropyl radical, it being possible for the hydrogen of the hydroxyl group of the hydroxypropyl radical to be substituted with another hydroxypropyl group or with a radical R.sub.1.
When CD represents the basic skeleton of .alpha.-cyclodextrin, n is preferably a value ranging from 3 to 5 and the total number m of groups R.sub.1 ranges from 2.5 to 14.
When CD represents the basic skeleton of .beta.-cyclodextrin, n is preferably a value ranging from 3 to 8 and in particular a value equal to 4.2 or 6.3, and the total number m of groups R.sub.1 ranges from 2.5 to 16.
When CD represents the basic skeleton of .gamma.-cyclodextrin, n is preferably a value ranging from 4 to 8, and the total number m of groups R.sub.1 ranges from 2.5 to 18.
The value of m may be determined by the saponification number or by the NMR spectrum.
CD is preferably .beta.-cyclodextrin.
n is preferably a statistical value ranging from 4 to 7.
The compounds according to the invention are virtually insoluble in water, the solubility decreasing as a function of the number of groups OR.sub.2. They are slightly soluble in oils such as diisopropyl adipate, but more soluble in alcohols such as ethanol or

REFERENCES:
patent: 5447920 (1995-09-01), Matsuda et al.
Chem. Pharm. Bull., vol. 23, No. 7, issued 1975, Uekam et al., "Inclusion Complexes of Cinnamic Acids with Cyclodextrin Mode of Inclusion in Aqueous Solution," pp. 1421-1430, 1975.

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