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WO1983002891A1 - Derives d'uracile comme additif anti-seborrheique pour produits cosmetiques - Google Patents

Derives d'uracile comme additif anti-seborrheique pour produits cosmetiques 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
Authority
WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
orotic acid
uracil
topical
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1983/000033
Other languages
German (de)
English (en)
Inventor
Kommanditgesellschaft Auf Aktien Henkel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of WO1983002891A1 publication Critical patent/WO1983002891A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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

Landscapes

  • 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.
PCT/EP1983/000033 1982-02-20 1983-02-12 Derives d'uracile comme additif anti-seborrheique pour produits cosmetiques Ceased WO1983002891A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP3206197.8820220 1982-02-20
DE19823206197 DE3206197A1 (de) 1982-02-20 1982-02-20 Uracil-derivate als antiseborrhoische zusaetze fuer kosmetische mittel

Publications (1)

Publication Number Publication Date
WO1983002891A1 true WO1983002891A1 (fr) 1983-09-01

Family

ID=6156296

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1983/000033 Ceased WO1983002891A1 (fr) 1982-02-20 1983-02-12 Derives d'uracile comme additif anti-seborrheique pour produits cosmetiques

Country Status (3)

Country Link
DE (1) DE3206197A1 (fr)
IT (1) IT8319631A0 (fr)
WO (1) WO1983002891A1 (fr)

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
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
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 (fr) 2005-07-22 2010-08-25 Mitsubishi Tanabe Pharma Corporation Procédé pour synthétiser un composant intermédiaire afin de synthétiser un agent pharmaceutique
WO2013183016A1 (fr) * 2012-06-06 2013-12-12 L'oreal Composés actifs pour combattre la peau grasse
FR2991577A1 (fr) * 2012-06-06 2013-12-13 Oreal Composes actifs contre la peau grasse

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3181979B2 (ja) 1992-04-30 2001-07-03 科学技術振興事業団 オロチン酸誘導体含有組成物並びに機能薄膜

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 (10)

* 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
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
EP0829476A3 (fr) * 1989-09-29 1999-02-24 Mitsubishi Chemical Corporation Dérivés de nucléoside acylopyrimidine 6-substitués et agent antiviral les contenant comme ingrédient actif
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 (fr) 2005-07-22 2010-08-25 Mitsubishi Tanabe Pharma Corporation Procédé pour synthétiser un composant intermédiaire afin de synthétiser un agent pharmaceutique
US7994315B2 (en) 2005-07-22 2011-08-09 Mitsubishi Tanabe Pharma Corporation Intermediate compound for synthesizing pharmaceutical agent and production method thereof
WO2013183016A1 (fr) * 2012-06-06 2013-12-12 L'oreal Composés actifs pour combattre la peau grasse
FR2991577A1 (fr) * 2012-06-06 2013-12-13 Oreal Composes actifs contre la peau grasse

Also Published As

Publication number Publication date
IT8319631A0 (it) 1983-02-17
DE3206197A1 (de) 1983-09-01

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