Hydroxystilbene compounds used as microbicidal active...

Details Hydroxystilbene compounds used as microbicidal active... Hydroxystilbene compounds used as microbicidal active...

2001-04-05

2004-11-09

McKane, Elizabeth (Department: 1744)

Drug, bio-affecting and body treating compositions

Anti-perspirants or perspiration deodorants

C424S070100, C514S733000, C568S744000

Reexamination Certificate

active

06814960

ABSTRACT:

The present invention relates to the use of hydroxystilbene compounds in the antimicrobial treatment of surfaces.
The hydroxystilbene compounds used according to the invention correspond to formula
wherein
A is a radical of formula
or a radical of formula
and
R
1
, R
2
, R
3
, R
4
and R
5
are each independently of the others hydrogen, halogen, hydroxy, C
1
-C
16
alkyl, C
1
-C
16
alkoxy, phenyl; C
1
-C
3
phenylalkyl; C
6
-C
10
aryloxy, amino, mono-C
1
-C
5
alkylamino, di-C
1
-C
5
alkylamino, or —NO
2
.
C
1
-C
16
Alkyl are straight-chain or branched alkyl radicals, e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl or hexadecyl.
C
1
-C
16
Alkoxy is e.g. methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, amyloxy, isoamyloxy or tert-amyloxy, hexyloxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tetradecyloxy, pentadecyloxy or hexadecyloxy.
C
6
-C
10
Aryloxy is phenoxy or naphthyloxy.
Halogen is fluorine, chlorine, bromine or iodine.
The hydroxystilbenes used according to the invention can be in the form of E- or Z-isomers.
They are preferably in the form of E-isomers.
Interesting compounds that are used according to the invention are dihydroxystilbenes, that is to say compounds of formula (1) wherein
R
1
and R
2
are hydroxy.
Very special preference is given to the use of compounds of formula
wherein
R
3
, R
4
and R
5
are as defined for formula (1), and more especially those compounds of formula (2) wherein R
3
, R
4
and R
5
are hydrogen.
Also preferred are compounds of formula
wherein
R
5
is as defined for formula (1) and is especially hydrogen.
The compounds of formula (3) are novel and the invention relates also thereto.
The preparation of the compounds of formula (1) is carried out in accordance with processes known per se by reaction of an alkyl phosphite, e.g. triethyl phosphite, with a benzyl halide, preferably benzyl bromide. The phosphonate intermediate is obtained (1st step).
The phosphonate intermediate is then reacted with an alkoxybenzaldehyde (2nd step). The subsequent dealkylation (3rd step) is carried out in accordance with customary methods.
The entire reaction sequence can be illustrated as follows:
1st Step
2nd Step
3rd Step
More details relating to this reaction can be found in Can. J. Chem. 48, 1554 (1970).
In a further variant, the hydroxystilbene compounds according to the invention can be prepared in a solid-phase synthesis using a trityl resin. The preparation is carried out in accordance with the following scheme:
wherein R
1
, R
2
and A are as defined for formula (1).
The method of synthesis is based on the literature procedure of R. Willard et al., Chemistry & Biology, 2, 1995, 45-51. The distinguishing feature of the preparation process according to the invention lies in the use of the trityl resin and the different method used for loading the resin.
More details relating to the preparation process according to the invention can be found in the corresponding Examples.
The hydroxystilbene compounds used according to the invention exhibit a pronounced antimicrobial action, especially against pathogenic gram-positive and gram-negative bacteria and also against bacteria of skin flora, e.g. Corynebacterium xerosis (bacteria that cause body odour), and also against yeasts and moulds. They are therefore especially suitable in the disinfection of the skin and mucosa and also of integumentary appendages (hair), more especially in the disinfection of the hands and of wounds.
They are therefore suitable as antimicrobial active ingredients and preservatives in personal care preparations, for example shampoos, bath additives, hair-care products, liquid and solid soaps (based on synthetic surfactants and salts of saturated and/or unsaturated fatty acids), lotions and creams, deodorants, other aqueous or alcoholic solutions, e.g. cleansing solutions for the skin, moist cleansing cloths, oils or powders.
The invention therefore relates also to a personal care preparation comprising at least one compound of formula (1) as well as cosmetically tolerable carriers or adjuvants.
The personal care preparation according to the invention comprises from 0.01 to 15% by weight, preferably from 0.1 to 10% by weight, based on the total weight of the composition, of the hydroxystilbene compound of formula (1), and cosmetically tolerable adjuvants.
Depending upon the form of the personal care preparation, it will comprise, in addition to the stilbene compound of formula (1), further constituents, for example sequestering agents, colourings, perfume oils, thickening or solidifying agents (consistency regulators), emollients, UV absorbers, skin-protective agents, antioxidants, additives that improve mechanical properties, such as dicarboxylic acids and/or Al, Zn, Ca and Mg salts of C
14
-C
22
fatty acids, and optionally preservatives.
The personal care preparation according to the invention may be formulated as a water-in-oil or oil-in-water emulsion, as an alcoholic or alcohol-containing formulation, as a vesicular dispersion of an ionic or non-ionic amphiphilic lipid, as a gel, a solid stick or as an aerosol formulation.
As a water-in-oil or oil-in-water emulsion, the cosmetically tolerable adjuvant contains preferably from 5 to 50% of an oily phase, from 5 to 20% of an emulsifier and from 30 to 90% water. The oily phase may contain any oil suitable for cosmetic formulations, e.g. one or more hydrocarbon oils, a wax, a natural oil, a silicone oil, a fatty acid ester or a fatty alcohol. Preferred mono- or poly-ols are ethanol, isopropanol, propylene glycol, hexylene glycol, glycerol and sorbitol.
Cosmetic formulations according to the invention may be contained in a variety of cosmetic preparations. Especially the following preparations, for example, come into consideration:
skin-care preparations, e.g. skin-washing and cleansing preparations in the form of tablet-form or liquid soaps, soapless detergents or washing pastes;
bath preparations, e.g. liquid (foam baths, milks, shower preparations) or solid bath preparations, e.g. bath cubes and bath salts;
skin-care preparations, e.g. skin emulsions, multi-emulsions or skin oils;
cosmetic personal care preparations, e.g. facial make-up in the form of day creams or powder creams, face powder (loose or pressed), rouge or cream make-up, eye-care preparations, e.g. eyeshadow preparations, mascara, eyeliner, eye creams or eye-fix creams; lip-care preparations, e.g. lipsticks, lip gloss, lip contour pencils, nail-care preparations, such as nail varnish, nail varnish removers, nail hardeners or cuticle removers;
intimate hygiene preparations, e.g. intimate washing lotions or intimate sprays;
foot-care preparations, e.g. foot baths, foot powders, foot creams or foot balsams, special deodorants and antiperspirants or callus-removing preparations;
light-protective preparations, such as sun milks, lotions, creams and oils, sun blocks or tropicals, pre-tanning preparations or after-sun preparations;
skin-tanning preparations, e.g. self-tanning creams;
depigmenting preparations, e.g. preparations for bleaching the skin or skin-lightening preparations;
insect-repellents, e.g. insect-repellent oils, lotions, sprays or sticks;
deodorants, such as deodorant sprays, pump-action sprays, deodorant gels, sticks or roll-ons;
antiperspirants, e.g. antiperspirant sticks, creams or roll-ons;
preparations for cleansing and caring for blemished skin, e.g. soapless detergents (solid or liquid), peeling or scrub preparations or peeling masks;
hair-removal preparations in chemical form (depilation), e.g. hair-removing powders, liquid hair-removing preparations, cream- or paste-form hair-removing preparations, hair-removing preparations in gel form or aerosol foams;
shaving preparations, e.g. shaving soap, foaming shaving creams, non-foaming shaving creams, foams and gels, preshave preparations for dry shaving, aftershaves or after-shave lotions;
fragrance prepara

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