Microbicidal active ingredients

Details Microbicidal active ingredients Microbicidal active ingredients

2000-08-01

2002-02-12

Aulakh, Charanjit S. (Department: 1625)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Wearing apparel, fabric, or cloth

C546S315000, C568S331000, C568S337000, C544S224000

Reexamination Certificate

active

06346260

ABSTRACT:

The present invention relates to the use of hydroxyphenyl-1,3-propanediones in the anti-microbial treatment of surfaces.
The hydroxyphenyl-1,3-propanediones used according to the invention correspond to formula:
R
1
and R
2
are each independently of the other hydrogen, C
1
-C
12
alkyl, C
1
-C
12
alkoxy, trifluoro-C
1
-C
3
alkyl, phenyl or halogen;
R
3
is a 5- or 6-membered heteroaromatic radical; thiophenyl; or a radical of formula:
R
4
, R
5
, R
6
and R
7
are each independently of the other hydrogen, halogen, C
1
-C
12
alkyl, C
1
-C
12
alkoxy, carboxy or trifluoro-C
1
-C
3
alkyl.
C
1
-C
12
Alkyl and C
1
-C
12
alkoxy are straight-chain or branched alkyl and alkoxy radicals, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl and dodecyl, and methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, amyloxy, isoamyloxy or tert-amyloxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy, decyloxy, undecyloxy and dodecyloxy.
Preferred 6-membered heteroaromatic radicals are pyrazinyl, pyrimidinyl and pyridazinyl and especially pyridyl.
Examples of 5-membered heteroaromatic radicals are thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, isoxazolyl and furazanyl.
The 5- or 6-membered heteroaromatic radicals may be unsubstituted or substituted by halogen, such as chlorine or bromine, by nitro, by C
1
-C
5
alkyl or by C
1
-C
5
alkoxy.
There are preferably used also compounds of formula:
wherein
R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
are as defined for formula (1).
Examples of compounds that can be used according to the invention correspond to formulae:
The preparation of the compounds of formula (1) is carried out in a manner known per se in analogy to K. A. Thakar, D. D. Goswami , G. G. Pachpor , J.Ind.Chem.Soc. (I) (1973), 420-423 in a two-step reaction in accordance with the following scheme:
1st Step
2nd Step
The invention relates also to the process for the preparation of the compounds according to formula (1).
The process is carried out in a suitable solvent, usually at a temperature of from 0 to 50° C. (1st step).
Preferably, pyridine is used as solvent at a temperature of 25° C.
In a 2nd step the ester of formula (10) is rearranged to form the corresponding target compound of formula (1) by reaction with KOH powder in a suitable solvent, preferably pyridine, at a temperature of from 40 to 80° C., preferably 50° C.
A further process for the preparation of the compounds of formula (1) is solid phase synthesis on polymeric supports.
For that purpose, R
1
- and R
2
-substituted hydroxyacetophenones of formula (9) are immobilised on a polystyrene-trityl chloride resin using suitable solvents, bases and catalysts, preferably dimethylformamide, N,N-diisopropylethylamine and 4-(N,N-dimethylamino)pyridine.
R
3
-Substituted esters are then heated with the polystyrene resin using suitable bases and solvents at temperatures of from 40 to 100° C.
Preferably, sodium tert-butanolate and N,N-dimethylacetamide are used at a temperature of 80° C.
For the removal of the compounds according to formula (1), the resins are treated with 5% trifluoroacetic acid in dichloromethane.
Some of the hydroxyphenyl-1,3-propanediones used according to the invention are known compounds, while some are new compounds.
The new compounds correspond to formula:
The hydroxyphenyl-1,3-propanediones 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, deodorisation and general antimicrobial treatment of the skin and mucosa and of integumentary appendages (hair), more especially in the disinfection of the hands and of wounds.
They are therefore suitable as antimicrobial active ingredients 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 0.5 to 10% by weight, based on the total weight of the composition, of the hydroxyphenyl-1,3-propanedione compound of formula (1) and cosmetically tolerable adjuvants.
Depending upon the form of the personal care preparation, it will comprise, in addition to the hydroxyphenyl-1,3-propanedione compound of formula (1), further constituents, for example sequestering agents, colourings, perfume oils, thickening or solidifying (consistency regulator) agents, emolients, 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 additional preservatives and antimicrobial active ingredients.
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.
A water-in-oil or oil-in-water emulsion containing the hydroxyphenyl-1,3-propanedione compound of formula (1) comprises as cosmetically tolerable adjuvants 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.
Compounds 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 nail hardener 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 callous-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 peelin

Affiliated with

Also associated with

Rating

Microbicidal active ingredients does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Microbicidal active ingredients, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Microbicidal active ingredients will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2971676