DE3825536A1 - USE OF HYDROPOXES FOR THE TREATMENT OF ACNE AND SEBORRHOE - Google Patents

Abstract

A hydroperoxide for use in the treatment of acne and seborrhoea has the general formula: <IMAGE> in which R1 and R2 are each a hydrogen atom or a C1-4 alkyl radical, and R3 is a linear or branched C1-21 alkyl radical, a linear or branched C2-17 alkenyl radical, a C4-17 alkadienyl radical, a C2-19 alkoxyalkyl radical, a C4-31 polyalkoxyalkyl radical, or a saturated or unsaturated C4-6, optionally substituted cycloalkyl radical, or R1 and R3, taken together with the carbon atom to which they are attached, form a saturated or unsaturated non-aromatic C4-6 ring, the sum of the carbon atoms of R1 + R2 + R3 being >/= 3.

Description

The subject of the present invention is the use a remedy for acne and seborrhea, which in a suitable carrier a hydroperoxide as contains active substance.

Acne as well as seborrhoea are the result of excessive Secretion of the sebaceous glands. As a result of seborrhoea the hair is usually fat, causing the aesthetic Sight of the hair is impaired. acne On the other hand, the face is relatively young, especially in the face Humans through the formation of characteristic lesions, namely, comedones noticeable.

These comedones are the result of a blockage of the Hair follicle canal as a result of dyskeratosis of the in fundibulum area of the canal. This will be a excessive proliferation of the remaining hair root enabled by the Propionibacterium acnes.

Consequence of this excessive bacterial proliferation is that in this milieu certain bacterial Pro teasen, which is a lysis of the follicle sack cause and in this way inflammatory substances in the interior of the skin on which the organism reacts with an inflammation.

The pathology of acne thus includes the following primers phenomena:

• - an increase in sebum secretion,
• - a disorder of keratosis of the hair follicle canal and
• - a bacterial hyperproliferation mainly by the Propionibacterium acnes.

A good remedy for acne, which treat acne effectively can, therefore, must have the following properties:

• a) It must be keratolytic and comedolytically effective be to prevent hyperkeratosis of the follicles and to allow the elimination of the comedone;
• b) It must act bacteriostatic to the activity of the Propionibacterien acnes to inhibit;
• c) It must have a sebostatic effect, a hypersecretion to inhibit borrhea.

Among the funds, which until now mainly as a means to serve against acne, the best known of these is undoubtedly Benzoyl peroxide, which is not only keratolytic, but also has comedolytic properties.

However, this peroxide always has certain side effects, often cause intolerance during treatment, such as As irritation lead; this is also the case when applied in relatively weak concentrations becomes.

The research carried out in this field have shown that certain hydroperoxides are replaced by a keratolytic, comedolytic and bacteriostatic Ak greater than that of benzoyl peroxide, without, however, the same disadvantages, as above all Irritation of the skin, to effect. Furthermore, it was found that the invention  used hydroperoxides a particularly pronounced have an anti-cellular effect without, however Intolerance effects, in particular itching the Scalp, trigger.

The subject of the present invention is thus the Ver use of at least one hydroperoxide of the following general formula

as an active substance for the preparation of an acne or Seborrhoea treatment for certain skin and hair remedies, wherein in the above-mentioned formula

R₁ and R₂ are the same or different and are a hydrogen atom or a lower alkyl radical, the sum of the carbon atoms of R₁ and R₂ being 8, and
R₃ is a straight or branched alkyl radical having 1 to 21 carbon atoms, a straight or branched alkenyl radical having 2 to 17 carbon atoms, an alka dienyl radical having 4 to 17 carbon atoms, an alkoxyalkyl radical having 2 to 19 carbon atoms, a polyalkoxyalkyl radical having 4 to 31 carbon atoms or an optionally substituted saturated or unsaturated cycloalkyl radical having 4 to 6 carbon atoms, or
R₁ and R₃ taken together form a non-aromatic, saturated or unsaturated ring having from 4 to 6 carbon atoms, the sum of the carbon atoms of R₁ + R₂ + R₃ being 3.

As the lower alkyl radical is a radical having 1 to 4 Koh lenstoffatomen, such as a methyl, ethyl, propyl, i-propyl or butyl radical, into consideration.

In a preferred embodiment of the invention Hydroperoxides of the primary type (R₁ = R₂ = H) before, wherein R₃ for a straight or branched fatty chain with 7 to 17 carbon atoms.

The various pharmacological investigations of Hydroperoxides of the agents according to the invention were able to show that these are due to their pronounced lipophilic nature penetrate well as well as keratolytic and comedolytic act, but without the known disadvantages of benzoyl peroxide.

The investigations also showed that they are effective against seborrhoea.

The hydroperoxides defined above are chemical more stable and pharmacologically more effective than the peroxides in general and as benzoyl peroxide in particular.

The hydroperoxides of the formula (I) include:

1-t-butyl hydroperoxide
1-pentyl
1-hexyl hydroperoxide
2-hexyl hydroperoxide
3-hexyl hydroperoxide
1-Heptylhydroperoxid
1-octyl
2-octyl
1-decyl hydroperoxide
1-Dodecylhydroperoxid
2-Dodecylhydroperoxid
1-Tetradecylhydroperoxid
2-Tetradecylhydroperoxid
1-Pentadecylhydroperoxid
1-Hexadecylhydroperoxid
4-Hexadecylhydroperoxid
1-Octadecylhydroperoxid
1-methylhexyl-1-hydroperoxide
2-ethylhexyl-1-hydroperoxide
1,1-dimethyloctyl-1-hydroperoxide
1,1-dimethylnonyl-1-hydroperoxide
2,6,10,14-Tetramethylpentadecyl-1-hydroperoxide
4-hexen-1-hydroperoxide
6-nonene-1-hydroperoxide
9-decen-1-hydroperoxide
10-undecen-1-hydroperoxide
11-tetradecen-1-hydroperoxide
11-hexadecene-1-hydroperoxide
9-octadecene-1-hydroperoxide
3,7-dimethyl-6-octen-1-hydroperoxide
3,5-hexadiene-1-hydroperoxide
4,8-undecadien-1-hydroperoxide
8,10-dodecadien-1-hydroperoxide
2-methoxyethyl-1-hydroperoxide
2-ethoxyethyl-1-hydroperoxide
2- (2-methoxyethoxy) ethyl-1-hydroperoxide
2- (2-ethoxyethoxy) ethyl-1-hydroperoxide
2- (2-Butyloxyethoxy) ethyl-1-hydroperoxide
cyclohexylhydroperoxide
1-i-propylcyclohexyl-1-hydroperoxide
2-methyl-2-cyclobutene-1-hydroperoxide
2-cyclopenten-1-hydroperoxide
3-cyclohexene-1-hydroperoxide
8-methylhydroperoxide
1-menthene-9-hydroperoxide

Among the most preferred hydroperoxides, both to satisfactory results against acne as well have led to seborrhoea, can be the following call:

1-t-butyl hydroperoxide
1-hexyl hydroperoxide
1-octyl
2-octyl
1-decyl hydroperoxide
1-Dodecylhydroperoxid
2-Dodecylhydroperoxid
1-Tetradecylhydroperoxid
1-Hexadecylhydroperoxid
2-ethylhexyl-1-hydroperoxide
6-nonene-1-hydroperoxide
9-decen-1-hydroperoxide
10-undecen-1-hydroperoxide
11-tetradecen-1-hydroperoxide
11-hexadecene-1-hydroperoxide
9-octadecene-1-hydroperoxide
3,7-dimethyl-6-octen-1-hydroperoxide
8,10-dodecadien-1-hydroperoxide
2- (2-ethoxyethoxy) ethyl-1-hydroperoxide
1-menthene-9-hydroperoxide

The above-mentioned hydroperoxides of the formula (I) are z. T. already described in the literature.

The new hydroperoxides can be prepared by known methods especially by passing through in two stages feeding method described in "Organic Peroxydes", Vol. 2, Pages 1-151, ed. v. Swern (Interscience Publishers, New York 1971).

After this method, in a first step, a re active sulfonate, preferably a brosylate, of the ent speaking alcohol.

The brosylate is obtained by the action of 4-bromine Benzenesulfonyl chloride on the corresponding alcohol in Presence of pyridine. The process is characterized by the following Equation described:

By nucleophilic substitution of the brosylate with the HO₂ anion, which is in situ by the action of Forming potassium hydroxide to hydrogen peroxide, you get the desired hydroperoxide:

This last reaction is preferably in a mixture from water / methanol or water / methanol / t-butanol carried out.

The yield of hydroperoxide varies, because it depends on the type of starting alcohol.

Those intended for the treatment of acne or seborrhoea Agents may be in various forms all in the form of a pomade, a gel, an emulsion, a lotion or a stick.

The term "pomade" refers to formulations such as Creams containing absorbable lipophilic raw materials such. As Vaseline, lanolin, polyethylene glycols as well Mixtures thereof, included.

The emulsions are oil-in-water or water-in-oil emulsions; they are made, by the hydroperoxide in the aqueous phase before the Emulsifying is dispersed.

The weight ratio of the fatty phase to the water phase is generally between 95: 5 and 25: 75.

Among the various oils that are suitable to to form the fat phase, can be different products use, like

• - animal oils, such as Lanolin, perhydrosqualene,
• - vegetable fats, such as sweet almond oil, avocado oil, Castor oil, olive oil, grapeseed oil, poppy seed oil, rapeseed oil, Peanut oil, corn oil, sunflower oil, nut oil, jojoba oil, Safflower oil, wheat germ oil, karit 'butter and Shorea robusta fat,
• - mineral oils, such. As paraffin oil and in others  Oils soluble silicone oils.

It is also possible to use fatty alcohols, such as cetyl alcohol, or certain synthetic products, such as. Saturated or unsaturated esters and especially i-propyl palmitate, i-propyl, butyl or cetyl myristate, hexadecyl, glycerol and polyethylene glycol stearate, ethyl palmitate, decyl oleate and the triglycerides of C₈-C₁₂ acids and cetyl ricinoleate, purcelin oil and hydrogenated polyisobutylene.

In the fat phase can also be certain waxes, as before all carnauba wax, beeswax, ozokerite wax, Can dellila wax or polyethylene wax.

The emulsion agents can also be other Ingredients, such as preservatives, sequestration medium, pigments, perfumes, sun filters, dyes, Emulsion stabilizers, such as magnesium sulfate, fillers, such as talc, and nylon, starch or polyethylene powder contain.

It goes without saying that the excipients and Ingredients should be selected so that they do not react with the hydroperoxides.

The gels are semi-solid preparations which are replaced by Ge lation of a hydroperoxide suspension using a gel-forming agent are obtained. Such gel Artists are z. B. "Bentone gel" for the fat or water phase, which was distributed by the company N. L. INDUSTRIES is crosslinked polyacrylic acid, such as the one from the Company GOODRICH under the name CARBOPOL 940 and 941 sold and used in neutralized form, or cellulose derivatives.  

On request, the gel can also be a non-ionic border containing surfactant, such as a polyoxy ethylenated alcohol with 4 to 20 ethylene oxide units or sorbitol esters, which gives a better dispersion and availability of the hydroperoxide.

You can also a solvent, for. B. a lower one aliphatic alcohol, such as ethanol, in a ratio from 0.5 to 30% by weight, a preservative Add perfume and a dye.

The agents can also be a humectant, such as. B. Glycerol, sorbitol or propylene glycol, in a ratio from 1 to 20%.

The means described above generally include between 0.01 and 20% by weight of hydroperoxide of the formula (I), preferably between 0.05 and 10 wt .-%, based on the total weight of the agent.

According to a particular embodiment, the hydro peroxide together with a topical to use Active ingredient for acne or with an antibiotic Active substance, such as erythromycin, clindamycin or lincomycin, Esters and salts thereof are used.

In another embodiment, the hydroperoxide of formula (I) together with a keratolytic agent, such as Salicylic acid, an antiseptic agent, an antifungoid agent, such as imidazole derivatives, especially miconazole, or even an anti-inflammatory Means are used.

Serve the hydroperoxides of the formula (I) especially for Be The treatment of seborrhoea is preferred  in the form of a lotion or a shampoo before and included at least one anionic, cationic, non- ionic or amphoteric detergent. Anionic detergents include: alkyl sulfates, Alkyl ether sulfates, alkyl polyether sulfates, alkyl sulfonates (wherein the alkyl radicals have 8 to 18 carbon atoms), sulfated monoglycerides, sulfonated monoglycerides, sulfated alkanolamides, sulfonated alkanolamides, Fatty acid soaps, monosulfosuccinates of fatty alcohols, Condensation products of fatty acids with isethionic acid, Condensation products of fatty acids with methyl taurine, Kon condensation products of fatty acids with sarcosine and Kon condensation products of fatty acids with a protein hydrolyzate.

The cationic detergents include above all quaternary long chain ammonium compounds, esters of Fatty acids and aminoalcohols as well as polyetheramines.

Nonionic detergents include esters Polyols and sugars, condensation products of ethylene oxide with fatty acids, fatty alcohols, long-chain alkyl phenols, long-chain amides or polyglycerinated ones Fatty alcohols.

The amphoteric detergents mainly include Aspara derivatives of gins, condensation products of monochloroacetic acid with imidazolines or alkylaminopropionates.

In this embodiment, the concentration of the surfactant in general between 3 and 50% by weight, preferably between 5 and 25% by weight, based on the total weight of the agent.

The shampoos can also be thickening agents, like fat  acid alkanolamides, cellulose derivatives such as carboxy methylcellulose or hydroxymethylcellulose, or also contain natural rubber.

In the treatment of acne, those on the hydro peroxide of the formula (I) based agent at least once a day on the lesions in an amount of 0.5 to 10 mg / cm² applied; depending on the severity of the Skin affection may be the duration of treatment 2 to 14 Weeks.

In the treatment of seborrhoea used before preferably hydroperoxides in the form of lotions or Shampoos, which at least twice a week the entire hair are applied; the treatment must continue for a few weeks.

The following examples for the preparation of hydro peroxides as well as the examples of remedies against Acne and Seborrhoea serve to further explain the Invention.  

Preparation Examples Example 1 Preparation of 3,7-dimethyl-6-octene-1-hydroperoxide a) Preparation of 3,7-dimethyl-6-octene-1-ol-brosylate

In a three-necked flask equipped with a mechanical stirrer, a thermometer and a reflux condenser with calcium chloride tube, 9.5 g (6.09 10 ^-2 mol) of 3,7-dimethyl-6-octene-1-ol in 80 ml solubilized with potassium hydroxide dried pyridine.

The reaction mixture is cooled to 0 ° C. in an ice bath. Add 15.56 g (6.09 10 ^-2 mol) of brosyl chloride in small portions, keeping the temperature in the reaction mixture at 0 ° C. The mixture is then allowed to come to room temperature in 4 hours.

The reaction mixture is poured onto a hydrochloric acid solution (150 ml of 36% HCl in 300 ml H₂O). After Ex Traction with dichloromethane (2 × 100 ml) washes The organic phase with water until the pH is neutral is, dries over sodium sulfate and evaporated Solvent to give a colorless crude oil.

After filtration through silica gel (eluent: pentane / Dichloromethane 60/40) and evaporation of the solution This gives 7.07 g of brosylate (yield: 31%).

b) 3,7-dimethyl-6-octen-1-hydroperoxide

Dissolve 6.63 g (1.77.10 ^-2 mol) of 3,7-dimethyl-6-octene-1-ol-brosylate in 68 ml of methanol.

The reaction mixture is added at 35 ° C 7.2 ml (= 4 equivalents) (110 vol.) Of hydrogen peroxide (33%) too.

During 2 hours, 4.95 ml of a 20% aqueous Potassium hydroxide solution (= 1 equivalent) in 4 equal parts added.

After the addition of the potassium hydroxide, the reaction Mixture stirred for 12 hours.

The cooled solution is poured onto a hydrochloric acid solution (10 ml of 36% HCl in 100 ml of water).

After extraction with dichloromethane (3 × 100 cm 3) washes the organic phase with water until neutral and dried over sodium sulfate.

After evaporation of the solvent in the cold and Under vacuum, the crude oil is removed using the silica gel Chromatography (solvent: pentane / dichloromethane 60/40) cleaned.

After evaporation of the solvent in the cold and under vacuum, 1.63 g of pure hydroperoxide are obtained (Yield: 48%).

1 H NMR spectrum (250 MHz): corresponds to the structure;
Peroxide index: 98.5%;
TLC: silica gel
Eluent: CH₂Cl₂
a single pink spot - characteristic of hydroperoxides (E. Knappe, D. Peteri, Z. Anal. Chem. 190, 386, (1962)).

example 2 Preparation of 6-nonene-1-hydroperoxide a) Preparation of 6-nonene-1-ol-brosylate

The brosylate is made as in Example 1a above 6-Nonen-1-ol produced in a yield of 50%.

b) 6-nonene-1-hydroperoxide

According to the method described in Example 1b 4 g of brosylate give 920 mg of a colorless oil (Yield: 54%).

1 H NMR spectrum (250 MHz): corresponds to the structure;
Peroxide content: 95.9%
TLC: silica gel
Eluent: CH₂Cl₂
single pink spot - characteristic of hydro peroxides;

example 3 Preparation of 9-decene-1-hydroperoxide a) 9-decen-1-ol-brosylate

The brosylate will be as in the example described above 1a from 9-decene-1-ol with a yield of 35% manufactured.

b) 9-decen-1-hydroperoxide

According to the method described in Example 1b from 5 g of brosylate is obtained 1.64 g of a colorless  Oils (Yield: 59%).

1 H NMR spectrum (90 MHz): corresponds to the structure;
Peroxide content: 97%
TLC: silica gel
Eluent: CH₂Cl₂
single pink spot - characteristic of hydro peroxides;

example 4 Preparation of 10-undecene-1-hydroperoxide a) 10-undecene-1-ol-brosylate

The brosylate will be as in the example described above 1a from Undecylenalkohol with a yield of 43% made.

b) 10-undecene-1-hydroperoxide

According to the method described in Example 1b From 19.6 g of brosylate, 3.9 g of a colorless product are obtained Oils (yield: 42%).

1 H NMR spectrum (90 MHz): corresponds to the structure;
TLC: silica gel
Eluent: CH₂Cl₂
single pink spot - characteristic of hydro peroxides;

example 5 Preparation of 11-tetradecene-1-hydroperoxide a) 11-tetradecen-1-ol-brosylate

The brosylate will be as in the example described above  1a from 11-tetradecen-1-ol with a yield of 50% made.

b) 11-tetradecen-1-hydroperoxide

According to the method described in Example 1b From 4.75 g of brosylate, 1.35 g of a colorless product are obtained Oils (yield: 54%).

1 H NMR spectrum (250 MHz): corresponds to the structure;
Peroxide content: 98%
TLC: silica gel
Eluent: CH₂Cl₂
single pink spot - characteristic of hydro peroxides;

example 6 Preparation of 11-hexadecene-1-hydroperoxide a) 11-hexadecene-1-ol-brosylate

The brosylate will be as in the example described above 1a from 11-hexadecene-1-ol with a yield of 83% made.

b) 11-hexadecene-1-hydroperoxide

According to the method described in Example 1b From 4.35 g of brosylate, 1.2 g of a colorless product are obtained Oils (yield: 50%).

1 H NMR spectrum (80 MHz): corresponds to the structure;
Peroxide content: 97.8%
TLC: silica gel
Eluent: CH₂Cl₂
single pink spot - characteristic of hydro peroxides;

example 7 Preparation of 8,10-dodecadiene-1-hydroperoxide a) 8,10-dodecadien-1-ol

The brosylate will be as in the example described above 1a from 8,10-dodecadien-1-ol with a yield made of 67%.

b) 8,10-dodecadien-1-hydroperoxide

According to the method described in Example 1b from 6.36 g of brosylate is obtained 550 mg of a colorless Oils (yield: 10%).

1 H NMR spectrum (90 MHz): corresponds to the structure;
Peroxide content: 97%
TLC: silica gel
Eluent: CH₂Cl₂
single pink spot - specific for hydroperoxides;

example 8 Preparation of 1-Menthene-9-hydroperoxide a) 1-menthene-9-ol brosylate

The brosylate will be as in the example described above 1a from 1-menthene-9-ol with a yield of 42% manufactured.

b) 1-menthene-9-hydroperoxide

According to the method described in Example 1b  from 6.3 g of brosylate is obtained 890 mg of a colorless Oils (Yield: 31%).

1 H NMR spectrum (250 MHz): corresponds to the structure;
Peroxide content: 90.9%
TLC: silica gel
Eluent: CH₂Cl₂
pink spot - characteristic of hydroperoxides;

example 9 Preparation of 2- (2-ethoxy-ethoxy) -ethyl-1-hydro peroxide a) monoethyl ether bromoylate from diethylene glycol

The brosylate will be as in the example described above 1a from the monoethyl ether of diethylene glycol produced with a yield of 83%.

b) 2- (2-ethoxy-ethoxy) ethyl-1-hydroperoxide

According to the method described in Example 1b from 20 g of brosylate is obtained 3.82 g of a colorless Oils (yield: 45%).

1 H NMR spectrum (250 MHz): corresponds to the structure;
Peroxide content: 95%
TLC: silica gel
Eluent: dichloromethane / methanol (95/5)
single pink spot - characteristic of hydro peroxides;

example 10 Preparation of 2-dodecyl hydroperoxide a) 2-Dodecanolbrosylat

The brosylate will be as in the example described above 1a from 2-dodecanol with a yield of 60.5% manufactured.

b) 2-Dodecylhydroperoxid

According to the method described in Example 1b From 12 g of brosylate, 1.05 g of a colorless product are obtained Oils (yield: 18%).

1 H NMR spectrum (250 MHz): corresponds to the structure;
Peroxide content: 98%
TLC: silica gel
Eluent: CH₂Cl₂
single pink spot - characteristic of hydro peroxides;

Examples of the means Example 1: Gel for acne Carboxyvinyl polymer, sold under the name "CARBOPOL 940" by GOODRICH | 1 g - Diethylene glycol ethyl ether 20 g Polyethylene glycol 400 5 g - diisopropanolamine 0.1 g - Ethylenediaminetetraacetic acid 0.05 g 3,7-dimethyl-6-octene-1-hydroperoxide 0.15 g - Water 10 g - 90% ethanol 100 g

Example 2: Gel for acne - Polyethylene glycol 400 | 10 g - Hydroxypropylcellulose 1.5 g - i-propanol 60 g - Ethylenediaminetetraacetic acid 0.05 g 1-Dodecyl hydroperoxide 1 g - Octyl dodecanol 20 g - citric acid 0.05 g - 90% ethanol 100 g

Example 3: Gel for acne Diethylene glycol ethyl ether | 20 g - Ethylenediaminetetraacetic acid 0.01 g 9-octadecene-1-hydroperoxide 0.05 g - Hydroxyethyl cellulose 1 g - citric acid 0.05 g - Water 40 g - 90% ethanol 100 g

Example 4 Cream for Acne of the Oil-in-Water Type Mixture of glycerol monostearate and polyethylene glycol monostearate sold under the name "ARLATONE 983 S" by ATLAS | 5 g - Cetyl alcohol 3 g - perhydrosqualene 10 g - glycerol monostearate 2.5 g - butylhydroxyanisole 0.05 g - butylhydroxytoluene 0.05 g Triglycerides of caprylic and capric acid, sold under the name "MIGLYOL 812" by DYNAMIT NOBEL 10 g - glycerin 5 g - citric acid 0.02 g 1-octyl hydroperoxide 1 g - water on 100 g

Example 5: Cream for acne of the water-in-oil type Mixture of fatty acid salts and esters sold under the name "DEHYMULS F" by HENKEL | 8 g - Decyl oleate 8 g - Vaseline oil 5 g - white Vaseline 20 g - triglycerides of caprylic and capric acid 15 g - glycerin 5 g - Magnesium sulfate, 7 H₂O 0.5 g - preservative 0.05 g - Perfume 0.1 g 1-Menthene-9-hydroperoxide 1 g - water on 100 g

Example 6: Anhydrous ointment for acne - viscose Vaseline | 29.5 g - low-viscosity Vaseline oil 25 g Polyoxyethylenated lauryl alcohol with 4 moles of ethylene oxide, sold under the name "BRIJ 30" by the company. ICI 5 g - Polyethylene wax 10 g - triglycerides of caprylic and capric acid 30 g 1-hexadecyl hydroperoxide 0.5 g

Example 7: Lotion for acne - Polyethylene glycol 400 | 40 g - i-propanol 30 g - citric acid 0.1 g 5-phenylpentyl-1-hydroperoxide 0.2 g - Octyldodecanol on 100 g

Example 8: Alcoholic lotion against seborrhoea i-propanol | 74.8 g Triglycerides of caprylic and capric acid, sold under the name "MIGLYOL 812" by DYNAMIT NOBEL 10 g - Compound of the formula sold under the name "CYCLOMETHICONE 7207" by the company UNION CARBIDE 15 g 1-Dodecyl hydroperoxide 0.2 g

Example 9: Shampoo against seborrhoea - Lauryl ether ammonium sulfate (30% active substance) | 55 g - Polyoxyethylenated with 20 moles of ethylene oxide sorbitol monolaureate, sold under the name "TWEEN 20" from the company. ICI 4.5 g - Sorbitol laureate, sold under the name "SPAN 20" from the company. ICI 2 g - Glycerincocoat with 7 moles of ethylene oxide, sold under the name "CETIOL HE" by the company HENKEL 2.5 g - Diethanolamide of copra fatty acids, sold under the name "COMPERLAN KD" by the company HENKEL 2 g 1-octyl hydroperoxide 0.1 g - water on 100 g

Claims (7)

1. Use of at least one hydroperoxide of the following general formula as the active substance for the treatment of acne or seborrhea, wherein in the above-mentioned formula, R₁ and R₂ are the same or different and represent a hydrogen atom or a lower alkyl group, wherein the sum of the carbon atoms of R₁ + R₂ is 8, and
R₃ is a straight or branched alkyl radical having 1 to 21 carbon atoms, a straight or branched alkenyl radical having 2 to 17 carbon atoms, an alkadienyl radical having 4 to 17 carbon atoms, an alkoxyalkyl radical having 2 to 19 carbon atoms, a polyalkoxyalkyl radical having 4 to 31 carbon atoms or an optionally substituted saturated or unsaturated cycloalkyl radical having 4 to 6 carbon atoms, or
R₁ and R₃, taken together, form a non-aromatic saturated or unsaturated ring having from 4 to 6 carbon atoms, the sum of the carbon atoms of R₁ + R₂ + R₃ being 3. 2. Use according to claim 1, characterized ge indicates that R₁ and R₂ in the formula (I) for a hydrogen atom and R₃ for a straight or branched fatty chain of 7 to 17 carbon atoms stand. 3. Use according to any one of claims 1 or 2, characterized in that the hydroperoxide is selected from 1-t-butyl hydroperoxide
1-pentyl
1-hexyl hydroperoxide
2-hexyl hydroperoxide
3-hexyl hydroperoxide
1-Heptylhydroperoxid
1-octyl
2-octyl
1-decyl hydroperoxide
1-Dodecylhydroperoxid
2-Dodecylhydroperoxid
1-Tetradecylhydroperoxid
2-Tetradecylhydroperoxid
1-Pentadecylhydroperoxid
1-Hexadecylhydroperoxid
4-Hexadecylhydroperoxid
1-Octadecylhydroperoxid
1-methylhexyl-1-hydroperoxide
2-ethylhexyl-1-hydroperoxide
1,1-dimethyloctyl-1-hydroperoxide
1,1-dimethylnonyl-1-hydroperoxide
2,6,10,14-Tetramethylpentadecyl-1-hydroperoxide
4-hexen-1-hydroperoxide
6-nonene-1-hydroperoxide
9-decen-1-hydroperoxide
10-undecen-1-hydroperoxide
11-tetradecen-1-hydroperoxide
11-hexadecene-1-hydroperoxide
9-octadecene-1-hydroperoxide
3,7-dimethyl-6-octen-1-hydroperoxide
3,5-hexadiene-1-hydroperoxide
4,8-undecadien-1-hydroperoxide
8,10-dodecadien-1-hydroperoxide
2-methoxyethyl-1-hydroperoxide
2-ethoxyethyl-1-hydroperoxide
2- (2-methoxyethoxy) ethyl-1-hydroperoxide
2- (2-ethoxyethoxy) ethyl-1-hydroperoxide
2- (2-Butyloxyethoxy) ethyl-1-hydroperoxide
cyclohexylhydroperoxide
1-i-propylcyclohexyl-1-hydroperoxide
2-methyl-2-cyclobutene-1-hydroperoxide
2-cyclopenten-1-hydroperoxide
3-cyclohexene-1-hydroperoxide
8-menthyl hydroperoxide and
1-menthene-9-hydroperoxide. 4. Use according to claim 3, characterized in that the hydroperoxide is preferably selected from 1-t-butyl hydroperoxide
1-hexyl hydroperoxide
1-octyl
2-octyl
1-decyl hydroperoxide
1-Dodecylhydroperoxid
2-Dodecylhydroperoxid
1-Tetradecylhydroperoxid
1-Hexadecylhydroperoxid
2-ethylhexyl-1-hydroperoxide
6-nonene-1-hydroperoxide
9-decen-1-hydroperoxide
10-undecen-1-hydroperoxide
11-tetradecen-1-hydroperoxide
11-hexadecene-1-hydroperoxide
9-octadecene-1-hydroperoxide
3,7-dimethyl-6-octen-1-hydroperoxide
8,10-dodecadien-1-hydroperoxide
2- (2-ethoxyethoxy) ethyl-1-hydroperoxide
1-menthene-9-hydroperoxide. 5. Use according to one of the preceding claims, characterized in that the Hydroperoxide in a concentration between 0.01 and 20 wt .-%, preferably between 0.05 and 10 wt .-%, based on the total weight of the remedy, on average is. 6. Use according to one of the preceding claims, characterized in that the Means in the form of a pomade, a gel, an emulsion, a lotion or a stick. 7. Use according to one of claims 1 to 5, since characterized in that the  Agent in the form of a shampoo and in addition 3-50 wt .-%, preferably 5-25 wt .-% at least an anionic, cationic, nonionic or contains amphoteric surfactant.