WO1983002891A1 - Uracil derivatives as anti-seborrheic additives for cosmetic products - Google Patents

Uracil derivatives as anti-seborrheic additives for cosmetic products Download PDF

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Publication number
WO1983002891A1
WO1983002891A1 PCT/EP1983/000033 EP8300033W WO8302891A1 WO 1983002891 A1 WO1983002891 A1 WO 1983002891A1 EP 8300033 W EP8300033 W EP 8300033W WO 8302891 A1 WO8302891 A1 WO 8302891A1
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group
carbon atoms
orotic acid
uracil
topical
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PCT/EP1983/000033
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German (de)
French (fr)
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Kommanditgesellschaft Auf Aktien Henkel
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Möller, Hinrich
Wallat, Siegfried
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    • 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
    • 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
    • A61K8/4953—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 containing pyrimidine ring derivatives, e.g. minoxidil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • A61Q5/008—Preparations for oily hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/008—Preparations for oily skin

Definitions

  • the invention relates to topical, cosmetic preparations for improving the greasy and unsightly appearance of the hair and skin, in particular for the treatment of heavily greasy hair.
  • Shampoos with sulfur, mercury or tar additives were used to combat seborrhea on the hairy head. It has been shown that these known agents often lead to side effects with prolonged use, without really satisfactory results in terms of effectiveness or application properties.
  • DE-OS 19 06 665 was finally for the treatment of dandruff caused by seborrhea N, N-diethyl-m-toluamide proposed as an active ingredient.
  • DE-AS 2.102.172 describes agents with a sebum-gland-inhibiting effect due to the content of long-chain alkyl esters of 5-pyrrolidone- (2) -carboxylic acid. However, it has been shown that neither
  • N, N-diethyl-m-toluamide and 5-pyrrolidone- (2) -carboxylic acid esters show satisfactory antiseborrheic effects.
  • R 1 is an alkyl group having 1 to 18 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxymethyl group having 1 to 18 carbon atoms, a halogenomethyl or an arylalkyl group, a fluorine atom, an ester group -CO 2 R 2 , where R 2 represents an alkyl radical having 1-18 carbon atoms, or an amide group CONR 3 R 4 , where R 3 and R 4 are hydrogen, an alkyl group having 1-18 carbon atoms, an aryl or aralkyl group or together with the nitrogen atom a heterocyclic group Forming a ring, has a particularly high effectiveness in the treatment of seborrheic skin and very greasy hair.
  • the rest R 1 can take positions 5 or 6, The following are examples of the compounds to be used according to the invention:
  • the uracils with a lower alkyl or hydroxyalkyl group in 5- or 6-position are preferred, as are the orotic acid esters and amides.
  • the cosmetic compositions according to the invention are solutions of the active compounds of formula (I) to be used in water, in alcohol, in aqueous-alcoholic mixtures, in oils, suspensions, gels, emulsions, ointments, pastes or aerosols
  • Antiseborrheic uracil derivatives can be incorporated into almost all cosmetic products that are customary for the treatment of skin and hair, such as in hair lotions, hair shampoos, hair treatments, hair rinses or also in skin lotions and shake mixtures.
  • the preparations according to the invention contain known carriers and auxiliaries such as water, organic solvents, surface-active compounds, oils and fats, waxes, perfume oils, dyes, preservatives and the like.
  • Such shampoos can contain, in addition to the sebosuppressive active ingredient, anionic, cationic, nonionic or amphoteric surfactants, dyes, fragrances, thickeners or conditioning agents.
  • the cosmetic preparations according to the invention contain the uracil derivatives of the formula (I) in an amount of from 0.01 to 20 percent by weight, preferably 0.1 to 2 percent by weight, based on the weight of the entire preparation.
  • the agents according to the invention can be used daily; however, satisfactory results are achieved with a single weekly application.
  • the individual dose that should be used with each treatment is not critical. Adverse side effects were not observed. The greasy appearance of the hair is reduced and the re-greasing is delayed, which means that normal hair care is possible.
  • the agents according to the invention in the form of skin creams, milk preparations or shake mixtures It is possible to permanently improve the appearance of the skin through regular use.
  • Orotic acid was reacted with n-hexanol under the conditions of Example 1.
  • the compound had a melting point of 171-172 ° C.
  • Example 4 Orotic acid was reacted with n-octanol under the conditions of Example 1.
  • the orotic acid noctyl ester obtained had a melting point of 163-164 ° C.
  • Example 4
  • Orotic acid was reacted with n-decanol under the conditions of Example 1.
  • the orotic acid decyl ester obtained had a melting point of 158 ° C.
  • Orotic acid n-butyl ester (Example 1) Orotic acid ethyl ester, produced according to J.Am.Chem. Soc.
  • test substances in the form of a 1% strength solution in ethanol or ethanol / acetone (1: 1) were each brushed onto the back of the back of 6 rats. The other side was only treated with the solvent without active substance (control side).
  • the first criterion was assessed as to whether the majority of the assessors correctly recognized the treated page, differentiating as follows:
  • the second criterion was the difference between the right and left side, whereby 1 point was to be awarded for each judge and animal, in such a way that the darker side with 1 and the lighter side with 0 and, in the case of equality, both sides with 0 , 5 were graded.
  • the following table shows the evaluation results according to the aforementioned scheme for the substances examined.
  • Emulgade A (R) (mixture of
  • Cetylstearyl alcohol with non-ionic emulsifiers 8.0

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Les composés répondent à la formule (I):$(8,)$dans laquelle R1 représente un groupe alkyle ayant de 1 à 18 atomes de carbone, un groupe hydroxyalkyle ayant de 1 à 4 atomes de carbone, un groupe alkoxyméthyle ayant de 1 à 18 atomes de carbone, un groupe halogénométhyle ou arylalkyle, un atome de fluor, un groupe ester CO2 R2, dans lequel R2 représente un reste alkyle ayant de 1 à 18 atomes de carbone, ou un reste amide CONR3 R4, dans lequel R3 et R4 sont l'hydrogène, un groupe alkyle de 1 à 18 atomes de carbone, un groupe aryl ou aralkyle ou forment avec l'atome d'azote un anneau hétérocyclique. Les composés antiséborrhéiques sont utilisés à raison de 0,01 à 20 % en poids, de préférence 0,1 à 2 % en poids, rapporté au poids total de la composition.The compounds correspond to formula (I): $ (8,) $ in which R1 represents an alkyl group having from 1 to 18 carbon atoms, a hydroxyalkyl group having from 1 to 4 carbon atoms, an alkoxymethyl group having from 1 with 18 carbon atoms, a halomethyl or arylalkyl group, a fluorine atom, a CO2 ester group R2, in which R2 represents an alkyl residue having from 1 to 18 carbon atoms, or an amide residue CONR3 R4, in which R3 and R4 are hydrogen, an alkyl group of 1 to 18 carbon atoms, an aryl or aralkyl group or form with the nitrogen atom a heterocyclic ring. The antiseborrheic compounds are used in an amount of 0.01 to 20% by weight, preferably 0.1 to 2% by weight, based on the total weight of the composition.

Description

"Uracil-Derivate als antiseborrhoische Zusätze für kosmetische Mittel" "Uracil derivatives as anti-seborrheic additives for cosmetic products"
Gegenstand der Erfindung sind topische, kosmetische Zubereitungen zur Verbesserung des fettigen und unästhetischen Aussehens der Haare und der Haut, insbesondere zur Behandlung von stark fettendem Haar.The invention relates to topical, cosmetic preparations for improving the greasy and unsightly appearance of the hair and skin, in particular for the treatment of heavily greasy hair.
Die übermäßig starke Absonderung der Talgdrüsen der Kopfhaut verleiht dem Haar ein fettiges Aussehen, das im allgemeinen als wenig ästhetisch angesehen wird. Es ist daher vielfach versucht worden, durch geeignete Mittel die Sekretion der Talgdrüsen zu normalisieren, um dem Haar wieder sein gesundes Aussehen zu geben. Zur Therapie der Seborrhoe wurden in derThe excessive secretion of the sebaceous glands of the scalp gives the hair a greasy appearance, which is generally considered to be less aesthetic. Many attempts have therefore been made to normalize the secretion of the sebaceous glands by means of suitable means in order to give the hair its healthy appearance again. For the treatment of seborrhea in the
DE-OS 16 67 902 peroral verabreichbare Zubereitungen, welche Cysteamin-Derivate enthalten, vorgeschlagen. Es wurden zur Bekämpfung der Seborrhoe des behaarten Kopfes Shampoos mit Schwefel, Quecksilber oder Teerzusatz verwendet. Dabei hat sich gezeigt, daß diese bekannten Mittel bei längerer Anwendung häufig zu Nebenwirkungen führen, ohne daß wirklich befriedigende Ergebnisse im Hinblick auf Wirksamkeit oder anwendungstechnische Eigenschaften erzielt werden konnten. in der DE-OS 19 06 665 wurde schließlich zur Behandlung der durch Seborrhoe verursachten Schuppenbildung N,N-Diethyl-m-Toluamid als Wirkstoff vorgeschlagen. In der DE-AS 2.102.172 werden Mittel mit einer talgdrüsenhemmenden Wirkung durch einen Gehalt an lang- kettigen Alkylestern der 5-Pyrrolidon-(2)-carbonsäure beschrieben. Es hat sich jedoch gezeigt, daß wederDE-OS 16 67 902 orally administrable preparations containing cysteamine derivatives proposed. Shampoos with sulfur, mercury or tar additives were used to combat seborrhea on the hairy head. It has been shown that these known agents often lead to side effects with prolonged use, without really satisfactory results in terms of effectiveness or application properties. in DE-OS 19 06 665 was finally for the treatment of dandruff caused by seborrhea N, N-diethyl-m-toluamide proposed as an active ingredient. DE-AS 2.102.172 describes agents with a sebum-gland-inhibiting effect due to the content of long-chain alkyl esters of 5-pyrrolidone- (2) -carboxylic acid. However, it has been shown that neither
N,N-Diethyl-m-Toluamid noch 5-Pyrrolidon-(2)-carbonsäureester zufriedenstellende antiseborrhoische Wirkungen zeigen.N, N-diethyl-m-toluamide and 5-pyrrolidone- (2) -carboxylic acid esters show satisfactory antiseborrheic effects.
Es wurde nun gefunden, daß topische, kosmetische Zu bereitungen mit einem Gehalt an üracil-Derivaten der allgemeinen Formel:It has now been found that topical, cosmetic preparations containing uracil derivatives of the general formula:
Figure imgf000004_0001
Figure imgf000004_0001
in der R1 für eine Alkylgruppe mit 1 - 18 Kohlenstoffatomen, eine Hydroxyalkylgruppe mit 1 - 4 Kohlenstoff atomen, eine Alkoxymethylgruppe mit 1 - 18 Kohlen stoffatomen, eine Halogenmethyl- oder eine Arylalkyl gruppe, ein Fluoratom, eine Estergruppe-CO2R 2, wobei R2 füreinen Alkylrest mit 1 - 18 Kohlenstoffatomen steht, oder eine Amidgruppe CONR3R4, wobei R3 und R4 Wasser stoff, eine Alkylgruppe mit 1 - 18 Kohlenstoffatomen, eine Aryl- oder Aralkylgruppe bedeuten oder zusammen mit dem Stickstoffatom einen heterocyclischen Ring bilden, steht, eine besonders hohe Wirksamkeit bei der Behandlung von seborrhoischerHaut und von stark fettendem Haar aufweisen. Der Rest R 1 kann die Posi tionen 5 oder 6 einnehmen, Als Beispiel für die erfindungsgemäß einzusetzenden Verbindungen sind zu nennen:in which R 1 is an alkyl group having 1 to 18 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxymethyl group having 1 to 18 carbon atoms, a halogenomethyl or an arylalkyl group, a fluorine atom, an ester group -CO 2 R 2 , where R 2 represents an alkyl radical having 1-18 carbon atoms, or an amide group CONR 3 R 4 , where R 3 and R 4 are hydrogen, an alkyl group having 1-18 carbon atoms, an aryl or aralkyl group or together with the nitrogen atom a heterocyclic group Forming a ring, has a particularly high effectiveness in the treatment of seborrheic skin and very greasy hair. The rest R 1 can take positions 5 or 6, The following are examples of the compounds to be used according to the invention:
5-, β-Methyl-, -Ethyl-, -Propyl-, -Butyl-, -Octyl-, -Decyl-, -Dodecyl-, -Tetradecyl-, -Octadecyl-, 6-Meth oxymethyl-, -Butoxymethyl-, -Octyloxymethyl-, -Dodecyl oxymethyl-, -Hexadecyloxymethyl-, 6-Chlor-methyl-,5-, β-methyl, ethyl, propyl, butyl, octyl, decyl, dodecyl, tetradecyl, octadecyl, 6-meth oxymethyl, butoxymethyl, -Octyloxymethyl-, -Dodecyl oxymethyl-, -Hexadecyloxymethyl-, 6-chloro-methyl-,
5-, 6-Fluor-uracil, Orot- bzw. Isoorotsaure-methyl-, -ethyl-, -propyl-, -isopropyl-, -butyl-, -hexyl-, -octyl-,5-, 6-fluoro-uracil, orot- or isoorotoyl-methyl-, -ethyl-, -propyl-, -isopropyl-, -butyl-, -hexyl-, -ctyl-,
-decyl-, -dodecyl-, -hexadecyl-ester, sowie -dimethyl-, -diethyl-, -dibutyl-, -dihexyl-, -butyl-, -hexyl-,-decyl-, -dodecyl-, -hexadecyl-esters, and -dimethyl-, -diethyl-, -dibutyl-, -dihexyl-, -butyl-, -hexyl-,
-decyl-, -hexadecyl-amid, -anilid, -N-methylanilid,-decyl-, -hexadecyl-amide, -anilide, -N-methylanilide,
-morpholid und -piperidid.-morpholide and -piperidide.
Bevorzugt werden vor allem die Uracile mit einer niederen Alkyl- oder Hydroxyalkylgruppe in 5- oder 6-Po sition, sowie die Orotsäureester und Amide.The uracils with a lower alkyl or hydroxyalkyl group in 5- or 6-position are preferred, as are the orotic acid esters and amides.
Die meisten Verbindungen gemäß Formel (I) sind literaturbekannt und zum großen Teil im Handel erhältlich. Sie sind nach an sich bekannten Methoden der organischen Chemie herstellbar. Die Verbindungen Orotsäure octylester und -decylester sowie 6-Butoxy-methyl uracil stellen einen weiteren Gegenstand der vorliegenden Erfindung dar.Most of the compounds according to formula (I) are known from the literature and a large part of them are commercially available. They can be produced according to known methods of organic chemistry. The compounds orotic acid octyl ester and decyl ester and 6-butoxymethyl uracil represent a further subject of the present invention.
Die erfindungsgemäßen kosmetischen Mittel stellen Lösungen der einzusetzenden wirksamen Verbindungen der Formel (I) in Wasser, in Alkohol, in wäßrig-alko holischen Mischungen, in ölen, Suspensionen, Gelen, Emulsionen, Salben, Pasten oder Aerosolen dar. Die antiseborrhoischen Uracil - Derivate können in fast alle zur Behandlung von Haut und Haaren üblichen kosmetischen Mittel, eingearbeitet werden, wie zum Beispiel in Haarwässern, Haarshampoos, Haarkuren, Haarspülungen oder auch in Hautlotionen und Schüttelmixturen. Neben den Verbindungen der Formel (I) enthalten die erfindungsgemäßen Zubereitungen bekannte Träger und Hilfsstoffe wie Wasser, organische Lösungsmittel, oberflächenaktive Verbindungen, Öle und Fette, Wachse, Parfümöle, Farbstoffe, Konservierungsmittel und dergleichen. Eine vorteilhafte Anwendungsform zur Behandlung von stark fettendem Haar ist das Shampoo. Derartige Shampoos können neben dem sebosuppressiven wir.kstoff anionische, kationische, nichtionische oder amphotere Tenside, Farbstoffe, Duftstoffe, Verdickungsmittel oder Konditionierungsmittel enthalten.The cosmetic compositions according to the invention are solutions of the active compounds of formula (I) to be used in water, in alcohol, in aqueous-alcoholic mixtures, in oils, suspensions, gels, emulsions, ointments, pastes or aerosols Antiseborrheic uracil derivatives can be incorporated into almost all cosmetic products that are customary for the treatment of skin and hair, such as in hair lotions, hair shampoos, hair treatments, hair rinses or also in skin lotions and shake mixtures. In addition to the compounds of the formula (I), the preparations according to the invention contain known carriers and auxiliaries such as water, organic solvents, surface-active compounds, oils and fats, waxes, perfume oils, dyes, preservatives and the like. An advantageous form of application for the treatment of greasy hair is the shampoo. Such shampoos can contain, in addition to the sebosuppressive active ingredient, anionic, cationic, nonionic or amphoteric surfactants, dyes, fragrances, thickeners or conditioning agents.
Die erfindungsgemäßen kosmetischen Zubereitungen enthalten die Uracil-Derivate der Formel (I) in einer Menge- von 0,01 bis 20 Gewichtsprozent, vorzugsweise 0,1 - 2 Gewichtsprozent, bezogen auf das Gewicht der gesamten Zubereitung. Die erfindungsgemäßen Mittel können täglich angewendet werden; es werden jedoch bereits bei einmaliger wöchentlicher Anwendung zufriedenstellende Ergebnisse erzielt. Die individuelle Dosis, die bei jeder Behandlung angewendet werden sollte, ist nicht kritisch. Nachteilige Nebeneffekte wurden nicht beobachtet. Das fettige Aussehen des Haares wird vermindert und das Nachfetten verzögert, wodurch die Möglichkeit einer normalen Haarpflege gegeben ist. Bei Einsatz der erfindungsgemäßen Mittel in Form von Hautcremes Milchpräparaten oder Schüttelmixturen gelingt es, durch regelmäßige Anwendung auf der Haut deren Aussehen dauerhaft zu verbessern.The cosmetic preparations according to the invention contain the uracil derivatives of the formula (I) in an amount of from 0.01 to 20 percent by weight, preferably 0.1 to 2 percent by weight, based on the weight of the entire preparation. The agents according to the invention can be used daily; however, satisfactory results are achieved with a single weekly application. The individual dose that should be used with each treatment is not critical. Adverse side effects were not observed. The greasy appearance of the hair is reduced and the re-greasing is delayed, which means that normal hair care is possible. When using the agents according to the invention in the form of skin creams, milk preparations or shake mixtures It is possible to permanently improve the appearance of the skin through regular use.
Die nachfolgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern. The following examples are intended to explain the subject matter of the invention in more detail.
Beispiel 1example 1
Herstellung von Orotsäure-n-butylesterProduction of n-butyl orotic acid
Die Mischung von 100 g (0,64 Mol) Orotsaure, 10 1 n-Butanol, 100 ml konz. Schwefelsäure und 150 ml Toluol wurde 12 Stunden am Wasserabscheider zum Sieden erhitzt, wonach eine klare Lösung entstanden war. Nach dem Erhalten und Waschen des Niederschlags mit Butaήol wurden 76 g (56 % d.Th.) Orotsäure-butylester vom Schmelzpunkt : 179 - 180°C erhalten. Nach dem Umkristallisieren aus Wasser steigt der Schmp. auf 182°C. Durch Konzentrieren der Mutterlauge kann die Ausbeute auf 80 % d.Th. gesteigert werden.The mixture of 100 g (0.64 mol) orotic acid, 10 1 n-butanol, 100 ml conc. Sulfuric acid and 150 ml of toluene were boiled for 12 hours on a water separator, after which a clear solution had formed. After obtaining and washing the precipitate with butaήol, 76 g (56% of theory) of butyl orotate were obtained with a melting point of 179-180 ° C. After recrystallization from water, the melting point rises to 182 ° C. By concentrating the mother liquor, the yield can be increased to 80% of theory be increased.
Beispiel 2Example 2
Herstellung von Orotsäure-n-hexylesterProduction of n-hexyl orotic acid
Unter den Bedingungen von Beispiel 1 wurde Orotsäure mit n-Hexanol umgesetzt. Die Verbindung hatte einen Schmp. von 171 - 172°C.Orotic acid was reacted with n-hexanol under the conditions of Example 1. The compound had a melting point of 171-172 ° C.
Beispiel 3Example 3
Herstellung von Orotsäure-.n-octylesterProduction of orotic acid .n-octyl ester
Unter den Bedingungen von Beispiel 1 wurde Orotsäure mit n-Octanol umgesetzt. Der erhaltene Orotsäure-noctylester hatte einen Schmelzpunkt von 163 - 164°C. Beispiel 4Orotic acid was reacted with n-octanol under the conditions of Example 1. The orotic acid noctyl ester obtained had a melting point of 163-164 ° C. Example 4
Herstellung von Orotsäure-n-decylesterProduction of n-decyl orotic acid
Unter den Bedingungen von Beispiel 1 wurde Orotsäure mit n-Decanol umgesetzt. Der erhaltene Orotsäure-ndecylester hatte einen Schmelzpunkt von 158ºC.Orotic acid was reacted with n-decanol under the conditions of Example 1. The orotic acid decyl ester obtained had a melting point of 158 ° C.
Beispiel 5Example 5
Herstellung von Orotsäure-isobutylesterProduction of isobutyl orotic acid
Unter den Bedingungen von Beispiel 1 wurde Orotsäure it Isobutanol umgesetzt. Der erhaltene Orotsäureisobutylester hatte einen Schmelzpunkt von 235 236ºC. Orotic acid was reacted with isobutanol under the conditions of Example 1. The isobutyl orotic acid obtained had a melting point of 235-236 ° C.
Beispiel 6Example 6
Herstellung von 6-Butoxymethyl-uracilProduction of 6-butoxymethyl-uracil
Zu der Lösung von 17,2 g (0,75 Mol) Natrium in 400 ml Butanol wurden 30 g (0,19 Mol) 6-Chlormethyluracil gegeben und die Mischung 19 Stunden zum Sieden erhitzt. Nach dem Abkühlen wurde soviel Wasser zugesetzt, bis sich der Niederschlag gelöst hatte. Dann wurde mit konz. H2SO4 ein PH- Wert von 6 eingestellt.30 g (0.19 mol) of 6-chloromethyluracil were added to the solution of 17.2 g (0.75 mol) of sodium in 400 ml of butanol and the mixture was heated to boiling for 19 hours. After cooling, enough water was added until the precipitate had dissolved. Then with conc. H 2 SO 4 has a pH value of 6.
Von neu gebildetem Niederschlag wurde abfiltriert, die wäßrige Phase abgetrennt und diese mit Butanol ausgewaschen. Die vereinigten Butanolphasen wurden eingedampft, der Rückstand mehrmals mit Acetonitril heiß extrahiert, das Acetonitril abdestilliert und der Rückstand aus Acetonitril umkristallisiert. Es wurden 12 g (33 %) 6-Butoxymethyl-uracil vom Schmp.159162° C erhalten.The newly formed precipitate was filtered off, the aqueous phase was separated off and washed with butanol. The combined butanol phases were evaporated, the residue was extracted several times with hot acetonitrile, the acetonitrile was distilled off and the residue was recrystallized from acetonitrile. 12 g (33%) of 6-butoxymethyl-uracil with a melting point of 159162 ° C. were obtained.
Beispiel 7Example 7
Die sebosuppressive Wirkung der in den erfindungsgemäßen kosmetischen Zubereitungen eingesetzten Verbindungen wurde durch nachfolgend beschriebene Tierversuche näher untersucht.The sebosuppressive effect of the compounds used in the cosmetic preparations according to the invention was investigated in more detail by animal experiments described below.
Als Versuchstiere dienten männliche Wistar-Ratten von 220 - 230 g Körpergewicht. Beurteilt wurde visuell der Bräunungsgrad auf dem Rücken der dort geschorenen Ratten. Die Bräunung wird durch das braune Hautober flächenlipid der Ratten hervorgerufen. Dieser Test geht von der Beobachtung aus, daß junge weibliche Ratten sowie männliche Ratten nach dem Waschen mit Tensid lösung bzw. einem Lipidlösungsmittel und auch männli- ehe Ratten, die systematisch mit östrogen behandelt wurden, nur die normale helle, rosafarbene Haut nach dem Scheren aufweisen; parallel dazu sind aus den abgeschnittenen Haaren nur noch vergleichsweise sehr geringe Lipidmengen zu extrahieren. Es wurden die VerbindungenMale Wistar rats of 220-230 g body weight were used as test animals. The degree of browning on the back of the shaved rats was assessed visually. The tan is through the brown skin areal lipid of the rats. This test is based on the observation that young female rats and male rats after washing with a surfactant solution or a lipid solvent and also male rats which have been systematically treated with estrogen have only the normal light pink skin after shearing ; in parallel, only comparatively very small amounts of lipid can be extracted from the cut hair. There were connections
Orotsäure-n-butylester (Beispiel 1 ) Orotsäure-ethylester, hergestellt nach J.Am.Chem. Soc.Orotic acid n-butyl ester (Example 1) Orotic acid ethyl ester, produced according to J.Am.Chem. Soc.
53 (1931), Seite 1989 5-Fluor-uracil, Handelsprodukt und zum Vergleich 5-Pyrrolidon-(2)-carbonsäure hexadecylester (DE-AS 2.102.172) getestet.53 (1931), page 1989 5-fluoro-uracil, commercial product and for comparison 5-pyrrolidone- (2) -carboxylic acid hexadecyl ester (DE-AS 2.102.172) tested.
Zur Beurteilung der sebosuppressiven Wirksamkeit wurden die PrüfSubstanzen in Form einer 1 %igert Lösung in Ethanol oder Ethanol/Aceton (1 : 1) jeweils 6 Ratten halbseitig auf das Rückenfell gepinselt. Die andere Seite wurde nur mit dem Lösungsmittel ohne Wirksubstanz behandelt (Kontrollseite).To assess the sebosuppressive efficacy, the test substances in the form of a 1% strength solution in ethanol or ethanol / acetone (1: 1) were each brushed onto the back of the back of 6 rats. The other side was only treated with the solvent without active substance (control side).
Während der Versuchsdauer von 14 Tagen wurde an insgesamt 9 Tagen einmal appliziert. Zur weiteren Kontrolle diente eine Gruppe von 6 Ratten, die völlig unbehandelt blieben. Am Ende des Versuchs wurden die Tiere am Rücken und an den Flanken geschoren und von einem Beurteilerpanel (6 Personen) unabhängig unter Doppelblindbedingungen visuell abgemustert.During the test period of 14 days, application was carried out once on a total of 9 days. A group of 6 rats, which remained completely untreated, served for further control. At the end of the experiment, the animals were shorn on the back and on the flanks and by a panel of judges (6 people) independently visually inspected under double-blind conditions.
Als 1. Kriterium wurde bewertet, ob die Mehrheit der Beurteiler richtig die behandelte Seite erkannt haben, wobei wie folgt differenziert wurde:The first criterion was assessed as to whether the majority of the assessors correctly recognized the treated page, differentiating as follows:
Figure imgf000012_0001
Figure imgf000012_0001
Als 2. Kriterium wurde der Unterschied zwischen rechter und linker Seite gewertet, wobei pro Beurteiler und Tier jeweils 1 Punkt zu vergeben war, und zwar in der Weise, daß die dunklere Seite mit 1 und die hellere mit 0 und bei Gleichheit beide Seiten mit 0,5 benotet wurden.The second criterion was the difference between the right and left side, whereby 1 point was to be awarded for each judge and animal, in such a way that the darker side with 1 and the lighter side with 0 and, in the case of equality, both sides with 0 , 5 were graded.
Als 3. Kriterium wurden außerdem noch die Intensitätsunterschiede der Brauntöne nach folgender Skala bewertet:As a third criterion, the differences in intensity of the brown tones were also rated on the following scale:
3 Punkte stark braun3 points strong brown
2 Punkte mittel braun2 points medium brown
1 Punkt schwach braun1 point light brown
0 Punkte keine Braunfärbung0 points no brown color
Signifikante Differenzen zwischen unbehandelter und behandelter Seite nach der zweiten Bewertungs methode zeigen die lokale Wirksamkeit einer Substanz an. Nach der dritten Bewertungsmethode werden die Punktsummendifferenzen zwischen den unbehandelten Kontrolltieren und jeweils den behandelten und unbe handelten Seiten der Versuchstiergruppe gebildet, wobei wiederum signifikante Differenzen zwischen Kontrolltieren und der behandelten Seite der Versuchstiere die Wirkung einer Substanz deutlich machen.Significant differences between untreated and treated side after the second evaluation method indicate the local effectiveness of a substance. According to the third evaluation method, the point total differences between the untreated control animals and in each case the treated and untreated sides of the experimental animal group are formed, again significant differences between control animals and the treated side of the experimental animals making clear the effect of a substance.
Parallel dazu ist in der Regel auch ein deutlicher Unterschied zwischen der unbehandelten und der behandelten Seite der Versuchstiergruppen zu sehen. Dieser ist aber nicht immer so deutlich wie der zwischen Kontrolltieren und behandelter Seite, wo für es verschiedene Gründe geben kann, wie zum Beispiel mechanische Substanzübertragung von einer auf die andere Seite oder Lösungsmitteleinfluß. Zur Differenzierung der Effekte gemäß Beurteilungsmethode 2 und 3 wurde das .folgende Schema verwendet:At the same time, there is usually a clear difference between the untreated and the treated side of the experimental animal groups. However, this is not always as clear as that between the control animals and the treated side, where there can be various reasons, such as mechanical substance transfer from one side to the other or the influence of solvents. The following scheme was used to differentiate the effects according to assessment methods 2 and 3:
Figure imgf000013_0001
Figure imgf000013_0001
Die nachfolgende Tabelle zeigt die Bewertungsergebnisse nach vorgenanntem Schema für die untersuchten Substanzen.
Figure imgf000014_0001
The following table shows the evaluation results according to the aforementioned scheme for the substances examined.
Figure imgf000014_0001
Beispiel 6Example 6
Nachfolgend werden für die erfindungsgemäßen topischen Mittel zur Behandlung von stark fettendem Haar und seborrhoischer Haut Rezepturen gegeben:In the following, formulations are given for the topical agents according to the invention for the treatment of strongly oily hair and seborrheic skin:
Figure imgf000014_0002
Haarkur Gewichtsteile
Figure imgf000014_0002
Hair treatment parts by weight
Glycerinmono-distearat (Tegin M(R)) 0,7 kationisches Tensid 2,0 Cholesterin 0,2Glycerol monodistearate (Tegin M (R) ) 0.7 cationic surfactant 2.0 cholesterol 0.2
Sojalecithin 0,3Soy Lecithin 0.3
Emulgade A (R) (Gemisch vonEmulgade A (R) (mixture of
Cetylstearylalkohol mit nicht ionogenen Emulgatoren) 8,0Cetylstearyl alcohol with non-ionic emulsifiers) 8.0
Parfümöl 0,3Perfume oil 0.3
Orotsaure-n-hexylester 7,0Orotic acid n-hexyl ester 7.0
Wasser, vollentsalzt 81,5Water, fully desalinated 81.5
HautcremeSkin cream
Selbstemulgierendes Gemisch aus Mono/Diglyceriden höherer gesättigter Fettsäuren mit Kalium stearat (Cutina KD 16 (R) ) 16,0 Cetylstearylalkohol mit ca. 12 MolSelf-emulsifying mixture of mono / diglycerides of higher saturated fatty acids with potassium stearate (Cutina KD 16 (R) ) 16.0 cetylstearyl alcohol with approx. 12 mol
Ethylenoxid (Eumulgin B 1 (R)) 1,0Ethylene oxide (Eumulgin B 1 (R) ) 1.0
2-Octyldodecanol 6,02-octyldodecanol 6.0
Isopropylmyristat 4,0Isopropyl myristate 4.0
Glycerin 6,0Glycerin 6.0
5-Fluor-uracil 7,05-fluoro-uracil 7.0
Wasser 60,0Water 60.0
Bezugsquellen für die genannten Handelsprodukte:Sources of supply for the named commercial products:
Texapon(R)A Henkel KGaATexapon (R) A Henkel KGaA
Comperlan(R)KD Henkel KGaAComperlan (R) KD Henkel KGaA
Cutina(R)KD 16 Henkel KGaA Eumulgin(R)B 1 Henkel KGaA Tegin (R)M Atlas-Chemie Cutina (R) KD 16 Henkel KGaA Eumulgin (R) B 1 Henkel KGaA Tegin (R) M Atlas-Chemie

Claims

P a t e n t a n p r ü c h e Patent claims
1. Topische, kosmetische Zubereitungen, enthaltend eine Uracil-Verbindung der allgemeinen Formel (I)1. Topical cosmetic preparations containing an uracil compound of the general formula (I)
Figure imgf000016_0001
in der R1 für eine Alkylgruppe mit 1 - 18 Kohlenstoffatomen, eine Hydroxyalkylgruppe mit 1 - 4 Kohlenstoffatomen, eine Alkoxymethylgruppe mit 1 18 Kohlenstoffatomen, eine Halogenmethyl- oder eine Arylalkylgruppe, ein Fluoratem, eine Estergruppe CO2R2, wobei R2 für einen Älkylrest mit 1 - 18 Koh lenstoffatomen steht, oder eine Amidgruppe CONR 3R4, wobei R3 und R4 Wasserstoff, eine Alkylgruppe mit
Figure imgf000016_0001
in which R 1 is an alkyl group with 1 to 18 carbon atoms, a hydroxyalkyl group with 1 to 4 carbon atoms, an alkoxymethyl group with 1 to 18 carbon atoms, a halomethyl or an arylalkyl group, a fluorine atom, an ester group CO 2 R 2 , where R 2 is for one Alkyl radical with 1-18 carbon atoms, or an amide group CONR 3 R 4 , where R 3 and R 4 are hydrogen, an alkyl group with
1 - 18 Kohlenstoffatomen, eine Aryl- oder Araikyl gruppe bedeuten oder zusammen mit dem Stickstoff atom einen heteroeyclischen Ring bilden, steht, als antiseborrhoischen Wirkstoff neben üblichen1 to 18 carbon atoms, an aryl or araikyl group or together with the nitrogen atom form a heteroeyclic ring, is, as an antiseborrheic active ingredient, in addition to conventional ones
Träger- und Hilfsstoffen.Carriers and auxiliaries.
2. Topische, kosmetische Zubereitungen nach Anspruch 1, dadurch gekennzeichnet, daß sie eine Verbindung der allgemeinen Formel (I), in einer Menge von2. Topical, cosmetic preparations according to claim 1, characterized in that they are a compound of general formula (I), in an amount of
0,01 - 20 Gewichtsprozent, verzugsweise 0,1 - 2 Gewichtsprozent, bezogen auf die gesamter.. Zubereitungen, enthalten. 0.01 - 20 percent by weight, preferably 0.1 - 2 percent by weight, based on the total .. preparations.
3. Topische, kosmetische Zubereitungen nach Anspruch 1 und 2, dadurch gekennzeichnet, daß sie Orotsäure hexylester als antiseborrhoischen Wirkstoff neben üblichen Träger- und Hilfsstoffen enthalten.3. Topical, cosmetic preparations according to claim 1 and 2, characterized in that they contain orotic acid hexyl ester as an antiseborrheic active ingredient in addition to conventional carriers and auxiliaries.
4. Topische, kosmetische Zubereitungen nach Anspruch 1 und 2, dadurch gekennzeichnet, daß sie 6-Butoxy methyl-uracil als antiseborrhoischen Wirkstoff neben üblichen Träger- und Hilfsstoffen enthalten.4. Topical, cosmetic preparations according to claim 1 and 2, characterized in that they contain 6-butoxy methyl uracil as an antiseborrheic active ingredient in addition to conventional carriers and auxiliaries.
5. Orotsäure-octylester5. Octotic orotic acid
6. Orotsäure-decylester6. Orotic acid decyl ester
7. 6-Butoxymethyl-uracil 7. 6-butoxymethyl uracil
PCT/EP1983/000033 1982-02-20 1983-02-12 Uracil derivatives as anti-seborrheic additives for cosmetic products WO1983002891A1 (en)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2212395A (en) * 1987-11-19 1989-07-26 Sidney Hart Treatment of baldness in humans
EP0420763A2 (en) * 1989-09-29 1991-04-03 Mitsubishi Chemical Corporation 6-Substituted acyclopyrimidine nucleoside derivatives and antiviral agent containing the same as active ingredient thereof
US5461060A (en) * 1989-09-29 1995-10-24 Mitsubishi Kasei Corporation Pyrimidine derivatives and anti-viral agent containing the same as active ingredient thereof
USRE37979E1 (en) * 1989-09-29 2003-02-04 Mitsubishi Chemical Corporation Pyrimidine derivatives and anti-viral agent containing the same as active ingredient thereof
EP2221305A1 (en) 2005-07-22 2010-08-25 Mitsubishi Tanabe Pharma Corporation Method for synthesizing intermediate compound for synthesizing a pharmaceutical agent
WO2013183016A1 (en) * 2012-06-06 2013-12-12 L'oreal Active compounds for combating greasy skin
FR2991577A1 (en) * 2012-06-06 2013-12-13 Oreal Use of pyrimidine compounds as agent for preventing and/or treating greasy skin or greasy-prone skin and/or aesthetic associated skin disorder such as skin imperfections caused by hyperseborrhea and thick skin grain

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3544684A (en) * 1966-12-31 1970-12-01 Arthur Scherm Cosmetic composition containing uracil-4-carboxylic acid
US3966924A (en) * 1974-11-13 1976-06-29 Allergan Pharmaceuticals Composition and method for treating psoriasis

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3544684A (en) * 1966-12-31 1970-12-01 Arthur Scherm Cosmetic composition containing uracil-4-carboxylic acid
US3966924A (en) * 1974-11-13 1976-06-29 Allergan Pharmaceuticals Composition and method for treating psoriasis

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2212395A (en) * 1987-11-19 1989-07-26 Sidney Hart Treatment of baldness in humans
EP0420763A2 (en) * 1989-09-29 1991-04-03 Mitsubishi Chemical Corporation 6-Substituted acyclopyrimidine nucleoside derivatives and antiviral agent containing the same as active ingredient thereof
EP0420763A3 (en) * 1989-09-29 1991-09-18 Mitsubishi Kasei Corporation 6-substituted acyclopyrimidine nucleoside derivatives and antiviral agent containing the same as active ingredient thereof
AU642906B2 (en) * 1989-09-29 1993-11-04 Mitsubishi Chemical Corporation 6-substituted acyclopyrimidine nucleoside derivatives and antiviral agent containing the same as active ingredient thereof
US5461060A (en) * 1989-09-29 1995-10-24 Mitsubishi Kasei Corporation Pyrimidine derivatives and anti-viral agent containing the same as active ingredient thereof
EP0829476A2 (en) * 1989-09-29 1998-03-18 Mitsubishi Chemical Corporation 6-Substituted acyclopyrimidine nucleoside derivatives and antiviral agent containing the same as active ingredient thereof
EP0829476A3 (en) * 1989-09-29 1999-02-24 Mitsubishi Chemical Corporation 6-Substituted acyclopyrimidine nucleoside derivatives and antiviral agent containing the same as active ingredient thereof
USRE37979E1 (en) * 1989-09-29 2003-02-04 Mitsubishi Chemical Corporation Pyrimidine derivatives and anti-viral agent containing the same as active ingredient thereof
EP2221305A1 (en) 2005-07-22 2010-08-25 Mitsubishi Tanabe Pharma Corporation Method for synthesizing intermediate compound for synthesizing a pharmaceutical agent
US7994315B2 (en) 2005-07-22 2011-08-09 Mitsubishi Tanabe Pharma Corporation Intermediate compound for synthesizing pharmaceutical agent and production method thereof
WO2013183016A1 (en) * 2012-06-06 2013-12-12 L'oreal Active compounds for combating greasy skin
FR2991577A1 (en) * 2012-06-06 2013-12-13 Oreal Use of pyrimidine compounds as agent for preventing and/or treating greasy skin or greasy-prone skin and/or aesthetic associated skin disorder such as skin imperfections caused by hyperseborrhea and thick skin grain

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