WO1982001819A1 - Antidandruff agent - Google Patents
Antidandruff agent Download PDFInfo
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- WO1982001819A1 WO1982001819A1 PCT/DE1981/000216 DE8100216W WO8201819A1 WO 1982001819 A1 WO1982001819 A1 WO 1982001819A1 DE 8100216 W DE8100216 W DE 8100216W WO 8201819 A1 WO8201819 A1 WO 8201819A1
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- Prior art keywords
- hydrochloride
- imidazolylmethyl
- sulfide
- dichlorobenzyl
- chloro
- Prior art date
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
Definitions
- the present invention relates to agents with anti-dandruff action, which act as active ingredients (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride and 4-chloro-2- (l-imidazolylmethyl) diphenyl sulfide, hydrochloride contain.
- anti-dandruff agents such as zinc or magnesium pyridine thione or selenium disulfide
- Their mechanism of action consists in normalizing the significantly increased cell division activity in the epidermis in dandruff [Plewig, Klig ⁇ an Areh. clin. exp. Derm. 256, 406 (1970)].
- Effective anti-dandruff agents also have an anti-camthogenic effect, i.e. they lead to thinning of the epidermis.
- a reduction in toxicity would also be important as a promotion that is constantly being placed on modern medicinal products.
- the effectiveness against dandruff in the individual compositions must not deteriorate under the usual storage conditions of a bathroom.
- the antidandruff agent should also be inert towards other constituents of the application agent. Other characteristics of the active ingredient, such as color and smell, must meet the requirements that are placed on a cosmetic product today.
- the invention relates to an agent for inhibiting scaling of the scalp, characterized in that it has an effective dose (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride or 4-chloro-2- ( Contains 1-imidasolylmethyl) diphenyl sulfide, hydrochloride.
- the invention also relates to the use of (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride or 4-chloro-2- (1-imidazolylmethyl) diphenyl sulfide, hydrochloride for prophylactic and therapeutic treatment of the scalp against dandruff.
- (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride and 4-chloro-2- (1-imidasolylmethyl) diphenyl sulfide, hydrochloride are formulated in a manner known per se by being mixed with 0.1-5% by weight in ethanol / water or isopropanol / water for hair lotions or in 1-5% by weight for Sharapoos (hairdressing gels or inlay agents) and customary auxiliaries and carriers.
- hair treatment agents which contain fatty alcohol-folyalkylene oxide adducts in their preparations, preferably those of fatty alcohols of chain length with 10-20 carbon atoms with 5-40 mol ethylene oxide units.
- Possible hair treatment agents with an anti-dandruff effect are: hair shampoo, hair tonic, hair fixative, hairdressing cream, hair conditioner, hair treatment, hair lotion etc.
- the anti-dandruff active ingredients (3.4-dichlorobenzyl) - [2- (1-imidazolylmethyl) - phenyl] sulfide hydrochloride and 4-Chloro-2- (1-imidazolylmethyl) diphenyl sulfide, hydrochloride in shampoos, hair lotions, inlay agents and hairdressing gels.
- the agents mentioned contain other carriers and components customary in hair treatment compositions in the usual proportions.
- Surfactant components such as fatty alcohol sulfates and fatty alcohol ether sulfates are intended for this purpose.
- Amphoteric surfactants can also be used for this (eg miranols). The best preparations can be achieved with the above-mentioned surfactant component fatty alcohol polyalkylene oxide adduct.
- Other additives are emulsifiers (e.g. Na, K or alkanolamine salts of fatty acids), thickeners (e.g. NaCl, NH 4 Cl in combinations with alkyl ether sulfates), superfatting agents (e.g.
- polyoxyethylated lanolin derivatives such as lecithin derivatives or alkylolamides
- framework components such as paraffin, full-fat alcohols, Protein breakdown products, vitamin complexes, solubilizers such as vinyl pyrrolidone-vinyl acetate copolymeridates, plant extracts.
- the active substances should be used in amounts between 0.001 and 0.1 g per patient and per day.
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- General Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
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- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
An antidandruff agent containing, as active substances, the hydrochloride of the sulphide (3, 4-dichlorobenzyl)-[2-(1-imidazolylmethyl)-phenyl] as well as the hydrochloride of the sulphide 4-chloro-2-(1-imidazolylmethyl)-diphenyl.
Description
ANTISCHUPPENMITTEL ANTI-DUPLICANTS
Beschreibungdescription
Die vorliegende Erfindung betrifft Mittel mit Antischuppenwirkung, die als Wirkstoffe (3.4-Dichlorbenzyl)-[2-(1-imidazolylmethyl)- phenyl]-sulfid, Hydrochlorid und 4-Chlor-2-(l-imidazolylmethyl)- diphenyl-sulfid, Hydrochlorid enthalten.The present invention relates to agents with anti-dandruff action, which act as active ingredients (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride and 4-chloro-2- (l-imidazolylmethyl) diphenyl sulfide, hydrochloride contain.
Es sind bereits einige Antischuppen-Wirkstoffe, wie Zink- oder Magnesium-Pyridinthion oder Selendisulfid bekannt. Ihr Wirkungsmechanismus besteht in einer Normalisierung der bei Kopfschuppen deutlich erhöhten Zellteilungsaktivität in der Epidermis [Plewig, Kligπan Areh. klin. exp. Derm. 256, 406 (1970)]. Wirksame Antischuppenwirkstoffe weisen daneben eine antiakamthogene Wirkung auf, d.h. sie führen zu einer Epidermisverdünnung.Some anti-dandruff agents, such as zinc or magnesium pyridine thione or selenium disulfide, are already known. Their mechanism of action consists in normalizing the significantly increased cell division activity in the epidermis in dandruff [Plewig, Kligπan Areh. clin. exp. Derm. 256, 406 (1970)]. Effective anti-dandruff agents also have an anti-camthogenic effect, i.e. they lead to thinning of the epidermis.
Für ein neues Antischuppenmittel wäre neben einer verbesserten Wirkung, die den fortlaufenden Gebrauch in Form eines Haarshampoos entbehrlich machen würde, auch eine Herabsetzung der Toxizität als eine ständig an moderne Arzneimittel gestellte Förderung von Bedeutung. Die Wirksamkeit gegen Schuppen darf in den einzelnen Zusammensetzungen (Shampoo, Frisiergel etc.) unter den üblichen Lagerungsbedingungen eines Badezimmers nicht nachlassen. Der Antischuppenwirkstoff soll sich ferner inert gegenüber anderen Bestandteilen des Anwendungsmittels verhalten. Andere Merkmale des Wirkstoffes, wie Farbe und Geruch, müssen den Anforderungen, die heute an ein kosmetisches Mittel gestellt werden, entsprechen.For a new anti-dandruff agent, in addition to an improved effect, which would make continuous use in the form of a hair shampoo unnecessary, a reduction in toxicity would also be important as a promotion that is constantly being placed on modern medicinal products. The effectiveness against dandruff in the individual compositions (shampoo, hairdressing gel etc.) must not deteriorate under the usual storage conditions of a bathroom. The antidandruff agent should also be inert towards other constituents of the application agent. Other characteristics of the active ingredient, such as color and smell, must meet the requirements that are placed on a cosmetic product today.
Es wurde nun gefunden, daß (3.4-Dichlorbenzyl)-[2-(1-imidazolylmethyl)-phenyl]-sufid, Hydrochlorid und 4-Chlor-2-(1-imidazolylmethyl)-diphenyl-sulfid, Hydrochlorid weitgehend diese Forderungen erfüllen und nachhaltiger als die bekannten Mittel die Schuppenbildung der Kopfhaut hemmen.
Der Anteil der Verbindungen mit Antischuppenwirkung in den bekann ten Antischuppenmitteln ist mit 5 Gew.-% und mehr relativ hoch. (3.4-Dichlorbenzyl)-[2-(1-imidazolylmethyl)-phenyl]-sulfid, Hydrochlorid und 4-Chlor-2-(1-imidazolylmethyl)-diphenyl-sulfid, Hydrochlorid wirken schon in niedrigerer Dosierung hemmend auf die Schuppenbildung und können wegen ihrer geringen Toxizität deshalb auch unbedenklich zur prophylaktischen Behandlung von KopfhautSchuppen verwendet werden.It has now been found that (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride and 4-chloro-2- (1-imidazolylmethyl) diphenyl sulfide, hydrochloride largely meet these requirements and more effectively inhibit scalp scaling than the known agents. The proportion of antidandruff compounds in the known antidandruff agents is relatively high at 5% by weight and more. (3.4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride and 4-chloro-2- (1-imidazolylmethyl) diphenyl sulfide, hydrochloride have an inhibitory effect on dandruff formation even at lower doses and can Because of their low toxicity, they can also be safely used for the prophylactic treatment of scalp dandruff.
Gegenstand der Erfindung ist ein Mittel zur Hemmung der Schuppenbildung der Kopfhaut, dadurch gekennzeichnet, daß es eine wirksame Dosis (3.4-Dichlorbenzyl)-[2-(1-imidazolylmethyl)-phenyl]-sulfid, Hydrochlorid oder 4-Chlor-2-(1-imidasolylmethyl)-diphenyl sulfid, Hydrochlorid enthält.The invention relates to an agent for inhibiting scaling of the scalp, characterized in that it has an effective dose (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride or 4-chloro-2- ( Contains 1-imidasolylmethyl) diphenyl sulfide, hydrochloride.
Gegenstand der Erfindung ist außerdem die Verwendung von (3.4-Dichlorbenzyl)-[2-(1-imidazolylmethyl)-phenyl]-sulfid, Hydrochlorid oder 4-Chlor-2-(1-imidazolylmethyl)-diphenyl-sulfid, HydroChlorid zur prophylaktischen und therapeutischen Behandlung der Kopfhaut gegen Schuppen.The invention also relates to the use of (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride or 4-chloro-2- (1-imidazolylmethyl) diphenyl sulfide, hydrochloride for prophylactic and therapeutic treatment of the scalp against dandruff.
Die Verbindungen (3.4 -Dichlorbenzyl)-[2-(1-imidazolylmethyl)-phenyl]-sulfid, Hydrochlorid und 4-Chlor-2-(1-imidazolylmethyl)-diphenyl-sulfid, Hydrochlorid sowie ihre Herstellung sind aus dem US-Patent 4,006,243 bekannt. Aus der Beschreibung in US 4 ,006 ,234 geht hervor, daß die Verbindungen (3.4-Dichlorbenzyl)- [2-(1-imidazolylmethyl)-phenyi]-sulfid, Hydrochlorid und 4-Chlor-2-(1-imidazolylmethyl)-diphenyl-sulfid, Hydrochlorid vor allem antifungale Wirkungen besitzen. Die neu gefundene Eigenschaft der Verbindungen (3.4-Dichlorbenzyl)-[2-(1-imidazolylmethyl)-phenyl]-sulfid, Hydrochlorid und 4-Chlor-2-(1-imidazolylmethyl)-diphenyl-sulfid, Hydrochlorid steht in keinem Zusammenhang mit den beschriebenen physiologischen Wirkungen und war auch nicht aus den vorhandenen Angaben herzuleiten. Es war deshalb nicht vorhersehbar, daß die Verbindungen (3.4-Dichiorbenzyl)-[2-(1-iιnidazolylmethyl)-phenyl]-sulfid, Hydrochlorid und 4-Chlor-2-(imidazolylmethyl)-diphenyl-sulfid, Hydrochlorid bei der prophylaktischen
und therapeutischen Behandlung der Kopfhaut gegen Schuppen vorteilhafte Eigenschaften zeigen würden.The compounds (3.4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride and 4-chloro-2- (1-imidazolylmethyl) diphenyl sulfide, hydrochloride and their preparation are from the US patent 4,006,243 known. The description in US Pat. No. 4,006,234 shows that the compounds (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyi] sulfide, hydrochloride and 4-chloro-2- (1-imidazolylmethyl) - Diphenyl sulfide, hydrochloride mainly have antifungal effects. The newly found property of the compounds (3.4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride and 4-chloro-2- (1-imidazolylmethyl) diphenyl sulfide, hydrochloride is not related to the described physiological effects and could not be derived from the available information. It was therefore not foreseeable that the compounds (3.4-dichlorobenzyl) - [2- (1-iιnidazolylmethyl) phenyl] sulfide, hydrochloride and 4-chloro-2- (imidazolylmethyl) diphenyl sulfide, hydrochloride in the prophylactic and therapeutic treatment of the scalp against dandruff would show beneficial properties.
(3.4-Dichlorbenzyl)-[2-(1-imidazoiylsethyl)-phenyl]-sulfid, Hydrochlorid wird nach folgender Vorschrift hergestellt:(3.4-dichlorobenzyl) - [2- (1-imidazoiylsethyl) phenyl] sulfide, hydrochloride is prepared according to the following instructions:
2,72 g Imidazol in 50 ml Dimethylformamid werden mit 1,2 g Natriumhydridsuspension (80%ig) versetzt. Nach 1,5 Stunden bei Raumtemperatur setzt man 12,7 g (2-Chlormethyl-phenyl)-(3,4-dichlorbenzyl)-sulfid (analog J.Org.Chem. 30 (1965) 4074 dargestellt) zu und rührt 20 Stunden bei Säumteraperatur. Das Rohprodukt wird aus wässrig-alkalischer Lösung extrahiert und ins Hydrochlorid überführt.2.72 g of imidazole in 50 ml of dimethylformamide are mixed with 1.2 g of sodium hydride suspension (80%). After 1.5 hours at room temperature, 12.7 g of (2-chloromethylphenyl) - (3,4-dichlorobenzyl) sulfide (analogous to J.Org.Chem. 30 (1965) 4074) are added and the mixture is stirred for 20 hours with hem taper. The crude product is extracted from aqueous alkaline solution and converted into the hydrochloride.
Durch Umkristallisation aus Methylenchlorid/Äther erhält man 12,3 g (3,4-Dichlorbenzyl-[2-(1-imidazolylmethyl)-pheny]-sulfid, Hydrochlorid mit dem Schmelzpunkt 115-138°C. 4-Chlor-2-(1-imidazolylmethyl)-diphenyl-sulfid, Hydrochlorid wird nach folgender Vorschrift hergestellt: 2,72 g Imidazol in 50 ml Dimethylformamid werden mit 1,2 g Natriumhydridsuspension (80%ig) versetzt. Nach 1,5 Stunden bei Raumtemperatur setzt man 10,8 g 4-Chlor-2-chlormethyl-diphenylsulfid (Goll. Czech. Chem. Commun. 33 (1963) -1831) zu und. rührt 20 Stunden bei Raumtemperatur. Das Rohprodukt ward aus wässrig-alkalischer Lösung extrahiert und ins Hydrochlorid überführt. Durch Umkristallisation aus Methylenchlorid/Äther erhält man 9,5 g 4-Chlor-2-(1-imidazjolylmethyl)-diphenyl-sulfid, Hydrochlorid mit dem Schmelzpunkt 97-98ºC.
Für die erfindungsgemäße Verwendung werden (3.4-Dichlorbenzyl)-[2-(1-imidazolylmethyl)-phenyl]-sulfid, Hydrochlorid und 4-Chlor-2-(1-imidasolylmethyl)-diphenyl-sulfid, Hydrochlorid in an sich bekannter Weise formuliert, indem sie mit 0,1-5 Gew. % in Äthanol/Wasser oder Isopropanol/Wasser für Haarwässer oder in 1-5 Gew. % für Sharapoos (Frisiergels oder Einlegemittel) und üblichen Hilfs-und Trägerstoffen gemischt werden.Recrystallization from methylene chloride / ether gives 12.3 g (3,4-dichlorobenzyl- [2- (1-imidazolylmethyl) pheny] sulfide, hydrochloride with a melting point of 115-138 ° C. 4-chloro-2- ( 1-imidazolylmethyl) diphenyl sulfide, hydrochloride is prepared according to the following procedure: 2.72 g imidazole in 50 ml dimethylformamide are mixed with 1.2 g sodium hydride suspension (80%). 8 g of 4-chloro-2-chloromethyl-diphenyl sulfide (Goll. Czech. Chem. Commun. 33 (1963) -1831) and stirring for 20 hours at room temperature. The crude product was extracted from aqueous alkaline solution and converted into the hydrochloride. Recrystallization from methylene chloride / ether gives 9.5 g of 4-chloro-2- (1-imidazyolylmethyl) diphenyl sulfide, hydrochloride with a melting point of 97-98 ° C. For the use according to the invention, (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride and 4-chloro-2- (1-imidasolylmethyl) diphenyl sulfide, hydrochloride are formulated in a manner known per se by being mixed with 0.1-5% by weight in ethanol / water or isopropanol / water for hair lotions or in 1-5% by weight for Sharapoos (hairdressing gels or inlay agents) and customary auxiliaries and carriers.
Die besten Wirkungen gegen Schuppen weisen Haarbehandlungscittel auf, die in ihren Zubereitungen Fettalkohol-FolyalkylenoxidAddukte, vorzugsweise solche von Fettalkoholen der Kettenlängen mit 10-20 Kohlenstoffatomen mit 5-40 Mol Äthylenoxid-Einheiten, enthalten.The best effects against dandruff have hair treatment agents which contain fatty alcohol-folyalkylene oxide adducts in their preparations, preferably those of fatty alcohols of chain length with 10-20 carbon atoms with 5-40 mol ethylene oxide units.
Als Haarbehandlungsmittel mit Antischuppenwirkung kommen in Betracht: Haarshampoo, Haarwasser, Haarfestiger, Frisiercreme, Haarspülung, Haarkur, Haarlotion etc. Bevorzugte Anwendung finden die Antischuppenwirkstoffe (3.4-Dichlorbenzyl)-[2-(1-imidazolylmethyl)- phenyl]-sulfid-Hydrochlorid und 4-Chlor-2-(1-imidazolylmethyl)- diphenyl-sulfid, Hydrochlorid in Shampoos, Haarwässern, Einlegemitteln und Frisiergelen. Die genannten Mittel enthalten weitere in Haarbehandlungsmitteln übliche Trägerstoffe und Komponenten in dafür üblichen Mengenverhältnissen. Dafür vorgesehen sind tensidische Bestandteile, wie Fettalkoholsulfate, Fettalkoholäthersulfate. Es kommen dafür auch amphotere Tenside in Betracht (z.B. Miranole). Die besten Zubereitungen erreicht man mit der oben genannten tensidischen Komponente FettalkoholpolyalkylenoxidAddukt.
Weitere Zusätze sind Emulgatoren (z.B. Na-, K- oder Alkanolaminsalze von Fettsäuren), Verdickungsmittel (z.B. NaCl, NH4Cl in Kombinationen mit Alkyläthersulfaten), Überf ettungssittel (z.B. polyoxyäthylierte Lanolinderivate, Lecithinderivate oder Alkylolamide) und Gerüstbestandteile (wie Paraffin, Vollfettalkohole, Eiweißabbauprodukte, Vitaminkomplexe, Lösungsvermittler wie Vinylpyrrolidon-Vinylacetat-Copolymeridate, Pflanzenextrakte). Die Wirkstoffe sollen in Mengen zwischen 0,001 und 0,1 g pro Patient und pro Tag angewendet werden.
Possible hair treatment agents with an anti-dandruff effect are: hair shampoo, hair tonic, hair fixative, hairdressing cream, hair conditioner, hair treatment, hair lotion etc. The anti-dandruff active ingredients (3.4-dichlorobenzyl) - [2- (1-imidazolylmethyl) - phenyl] sulfide hydrochloride and 4-Chloro-2- (1-imidazolylmethyl) diphenyl sulfide, hydrochloride in shampoos, hair lotions, inlay agents and hairdressing gels. The agents mentioned contain other carriers and components customary in hair treatment compositions in the usual proportions. Surfactant components such as fatty alcohol sulfates and fatty alcohol ether sulfates are intended for this purpose. Amphoteric surfactants can also be used for this (eg miranols). The best preparations can be achieved with the above-mentioned surfactant component fatty alcohol polyalkylene oxide adduct. Other additives are emulsifiers (e.g. Na, K or alkanolamine salts of fatty acids), thickeners (e.g. NaCl, NH 4 Cl in combinations with alkyl ether sulfates), superfatting agents (e.g. polyoxyethylated lanolin derivatives, lecithin derivatives or alkylolamides) and framework components (such as paraffin, full-fat alcohols, Protein breakdown products, vitamin complexes, solubilizers such as vinyl pyrrolidone-vinyl acetate copolymeridates, plant extracts). The active substances should be used in amounts between 0.001 and 0.1 g per patient and per day.
Nachstehend werden einige Beispiele für Kaarbehandlungsmittel aufgeführt:Here are some examples of chewing agents:
Beispiel 1example 1
Shampooshampoo
2.0 Gew.-Teile (3,4-Dichlorbenzyl)-[2-(1-imidazolylmethyl)- phenyl]-sulfid-Hydrochlorid 40.0 " Natriumlaurylalkoholdiglycolethersulfat,2.0 parts by weight (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide hydrochloride 40.0 "sodium lauryl alcohol diglycol ether sulfate,
28%ige wässrige Lösung 4.0 " Natriumchlorid 0.2 " Parfümöl 0.1 " Farbstoff28% aqueous solution 4.0 "sodium chloride 0.2" perfume oil 0.1 "dye
53.7 " Wasser53.7 "water
Beispiel 2 HaarwasserExample 2 Hair Tonic
1.0 Gew.-Teile (3,4-Dichlorbenzyl) [2-(1-imidazolylmethyl)- phenyl]-sulfid-Hydrochlorid1.0 part by weight of (3,4-dichlorobenzyl) [2- (1-imidazolylmethyl) phenyl] sulfide hydrochloride
50.0 " Isopropylalkohol50.0 "isopropyl alcohol
0.2 " Parfümöl0.2 "perfume oil
0.1 " Farbstoff0.1 "dye
48.7 " Wasser
48.7 "water
Beispiel 3Example 3
Einlegemitt elInsert el
1.0 Gew. -Teile (3,4-Dichlorbenzyl-[2-(1-imidazolylmethyl)- phenyl]-sulfid-Hydrochlorid1.0 part by weight of (3,4-dichlorobenzyl- [2- (1-imidazolylmethyl) phenyl] sulfide hydrochloride
3.0 " Copolymer aus 60% Vinylpyrrolidon und 40%3.0 "copolymer of 60% vinyl pyrrolidone and 40%
Vinylazetat, in Pulverform 40.0 " Äthanol 94%Vinyl acetate, in powder form 40.0 "ethanol 94%
0.2 " Parfümöl0.2 "perfume oil
0.1 " Farbstoff0.1 "dye
55.7 " Wasser55.7 "water
Beispiel 4 FrisiergelExample 4
2.0 Gew. -Teile (3,4-Dichlorbenzyl)-[2-(1-imidazolylmethyl)- phenyl]-sulfid-Hydrochlorid 29.5 " Oleyl-cetylalkohol, mit 7-8 Mol Ethylenoxyd oxethyliert, 80%ig (Eusulgin K 8 der Fa.Henkel) 17.5 " Paraffinöl 0.2 " Parfümöl2.0 parts by weight of (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide hydrochloride 29.5 "oleyl cetyl alcohol, ethoxylated with 7-8 moles of ethylene oxide, 80% (Eusulgin K 8 der Henkel) 17.5 "Paraffin Oil 0.2" Perfume Oil
0.1 " Farbstoff0.1 "dye
51.7 " Wasse
51.7 "water
Beispiel 5 ShampooExample 5 Shampoo
2.0 Gew.-Teile 4-Chlor-2-(1-imidazolylmethyl)-diphenyl- sulfid, Hydrochlorid2.0 parts by weight of 4-chloro-2- (1-imidazolylmethyl) diphenyl sulfide, hydrochloride
40.0 '' Natriumlaurylalkoholdiglycolethersulfat,40.0 '' sodium lauryl alcohol diglycol ether sulfate,
28%ige wässrige Lösung28% aqueous solution
4.0 '' Natriumchlorid4.0 '' sodium chloride
0.2 '' Parfümöl0.2 '' perfume oil
0.1 '' Farbstoff0.1 '' dye
53-7 '' Wasser53-7 '' water
Beispiel 6Example 6
HaarwasserHair tonic
1.0 Gew.-Teile 4-Chlor-2-(1-imidazolylmethyl)-diphenyl- sulfid, Hydrochlorid1.0 part by weight of 4-chloro-2- (1-imidazolylmethyl) diphenyl sulfide, hydrochloride
50.0 " Isopropylalkohol50.0 "isopropyl alcohol
0.2 " Parfümöl0.2 "perfume oil
0.1 " Farbstoff0.1 "dye
48.7 " Wasser
48.7 "water
Beispiel 7 EinlegeraittelExample 7
1.0 Gew. -Teile 4-Chlor-2-(1- imidazolylmethyl)-diphenyl- sulfid, Hydrochlorid 3.0 " Copolymer aus 60% Vinylpyrrolidon und 40%1.0 part by weight of 4-chloro-2- (1-imidazolylmethyl) diphenyl sulfide, hydrochloride 3.0 "copolymer of 60% vinylpyrrolidone and 40%
Vinylazetat, in Pulverform 40.0 '' Äthanol 94% 0.2 " ParfümölVinyl acetate, in powder form 40.0 '' ethanol 94% 0.2 "perfume oil
0.1 " Farbstoff 55.7 " Wasser0.1 "dye 55.7" water
Beispiel 8Example 8
FrisiergelHairdressing gel
2.0 Gew. -Teile 4-Chlor-2-(1-imidazolylmethyl)-diphenyl- sulfid, Hydrochlorid2.0 parts by weight of 4-chloro-2- (1-imidazolylmethyl) diphenyl sulfide, hydrochloride
29.5 '' Oleyl-cetylalkohol, mit 7-8 Mol Ethylenoxyd oxethyliert, 8θ£ig (Eumulgin M 8 der Fa.Henkel)29.5 '' oleyl cetyl alcohol, ethoxylated with 7-8 mol ethylene oxide, 8θ pounds (Eumulgin M 8 from Henkel)
17.5 '' Paraffinöl 0.2 '' Parfümöl 0.1 '' Farbstoff17.5 '' paraffin oil 0.2 '' perfume oil 0.1 '' dye
51.7 '' Wasser
51.7 '' water
Claims
PatentansprücheClaims
1) Mittel zur Hemmung der Schuppenbildung der Kopfhaut, dadurch gekennzeichnet, daß es in einem geeigneten Trägermaterial1) Agent for inhibiting scaling of dandruff, characterized in that it is in a suitable carrier material
(3.4-Dichlorbenzyl)-[2-(1-imidazolylmethyl)-phenyl]-sulfid, Hydrochlorid in einer Menge von 0,1-5 Gewichtsprozenten, vorzugsweise 0,5-3 Gewichtsprozenten, bezogen auf das gesamte Mittel, enthält.(3.4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride in an amount of 0.1-5 percent by weight, preferably 0.5-3 percent by weight, based on the total agent.
2) Verwendung von (3-4-Dichlorbenzyl)-[2-(1-imidazolylmethyl)- phenyl]-sulfid, Hydrochlorid zur prophylaktischen und therapeutischen Behandlung der Kopfhaut gegen Schuppen.2) Use of (3-4-dichlorobenzyl) - [2- (1-imidazolylmethyl) - phenyl] sulfide, hydrochloride for the prophylactic and therapeutic treatment of the scalp against dandruff.
3) Mittel zur Hemmung der Schuppenbildung der Kopfhaut, dadurch gekennzeichnet, daß es in einem geeigneten Trägermaterial 4-Chlor-2-(1-imidazolylmethyl)-diphenyl-sulfid, Hydrochlorid in einer Menge von 0,1-5 Gewichtsprozenten, vorzugsweise 0,5-3 Gewichtsprozenten, bezogen auf das gesamte Mittel, enthält.3) Agent for inhibiting scaling of the scalp, characterized in that it contains 4-chloro-2- (1-imidazolylmethyl) diphenyl sulfide, hydrochloride in an amount of 0.1-5 percent by weight, preferably 0, in a suitable carrier material. 5-3 percent by weight, based on the total agent contains.
4) Verwendung von 4-Chlor-2-(1-imidazolylmethyl) -iphenyl- sulfid, Hydrochlorid zur prophylaktischen und therapeutischen Behandlung der Kopfhaut gegen Schuppen.
4) Use of 4-chloro-2- (1-imidazolylmethyl) -iphenyl sulfide, hydrochloride for the prophylactic and therapeutic treatment of the scalp against dandruff.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3046391801205 | 1980-12-05 | ||
| DE19803046391 DE3046391A1 (en) | 1980-12-05 | 1980-12-05 | Anti:dandruff compsn. contg. imidazolyl:methyl-phenyl sulphide deriv. - for therapeutic or prophylactic use |
| DE19813104430 DE3104430A1 (en) | 1981-02-04 | 1981-02-04 | Dandruff remedies |
| DE3104430 | 1981-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1982001819A1 true WO1982001819A1 (en) | 1982-06-10 |
Family
ID=25789617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/DE1981/000216 WO1982001819A1 (en) | 1980-12-05 | 1981-12-04 | Antidandruff agent |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0065974A1 (en) |
| JP (1) | JPS57502126A (en) |
| WO (1) | WO1982001819A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112013033914A2 (en) | 2011-06-30 | 2016-11-22 | Hansen Ab Gmbh | agent for the control of parasites in animals and use of an agent |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2430039A1 (en) * | 1974-06-22 | 1976-01-08 | Bayer Ag | AZOLANTIMYCOTICS AS COSMETIC AGENTS |
| US4006243A (en) * | 1974-04-11 | 1977-02-01 | Schering Aktiengesellschaft | Amino-, mercapto- and -oxy-substituted-phenyl and -phenalkyl imidazoles |
| GB2068228A (en) * | 1980-01-24 | 1981-08-12 | Janssen Pharmaceutica Nv | Novel anti-microbial compositions for the topical treatment of acne vulgaris |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS571781B2 (en) * | 1973-01-18 | 1982-01-12 | ||
| JPS5426197B2 (en) * | 1973-06-25 | 1979-09-03 |
-
1981
- 1981-12-04 EP EP19820900018 patent/EP0065974A1/en not_active Withdrawn
- 1981-12-04 WO PCT/DE1981/000216 patent/WO1982001819A1/en not_active Application Discontinuation
- 1981-12-04 JP JP50010182A patent/JPS57502126A/ja active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4006243A (en) * | 1974-04-11 | 1977-02-01 | Schering Aktiengesellschaft | Amino-, mercapto- and -oxy-substituted-phenyl and -phenalkyl imidazoles |
| DE2430039A1 (en) * | 1974-06-22 | 1976-01-08 | Bayer Ag | AZOLANTIMYCOTICS AS COSMETIC AGENTS |
| GB2068228A (en) * | 1980-01-24 | 1981-08-12 | Janssen Pharmaceutica Nv | Novel anti-microbial compositions for the topical treatment of acne vulgaris |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0065974A1 (en) | 1982-12-08 |
| JPS57502126A (en) | 1982-12-02 |
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