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WO1992006946A1 - Composes bicycliques a effet anti-seborrheique - Google Patents

Composes bicycliques a effet anti-seborrheique Download PDF

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Publication number
WO1992006946A1
WO1992006946A1 PCT/EP1991/001948 EP9101948W WO9206946A1 WO 1992006946 A1 WO1992006946 A1 WO 1992006946A1 EP 9101948 W EP9101948 W EP 9101948W WO 9206946 A1 WO9206946 A1 WO 9206946A1
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group
radicals
atoms
radical
hydrogen
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PCT/EP1991/001948
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German (de)
English (en)
Inventor
Hinrich Möller
Friedhelm Bartnik
Norbert Banduhn
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Henkel Kommanditgesellschaft Auf Aktien
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Publication of WO1992006946A1 publication Critical patent/WO1992006946A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C229/60—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in meta- or para- positions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
    • C07C65/26—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Definitions

  • the invention relates to bicyclic compounds of special structure, a process for the preparation of these compounds and their use as antiseborrheic agents for the production of topical, pharmaceutical or cosmetic preparations with sebosuppressive activity.
  • the invention therefore relates to bicyclic compounds of the general formula I.
  • A is a group -CHR 3 R 4 or an oxygen atom
  • radicals R 1 to R 5 are hydrogen or methyl groups
  • - n is the number 0 or 1
  • the radical R 6 is one of the groups -CH 2 OH, -CO 2 H, -CO 2 R 7 or -COR 7 ,
  • the radical R 7 is an alkyl group with 1 to 4 carbon atoms and
  • the six-membered ring formed from the atoms C-1 to C-6 contains one or two double bonds or represents an aromatic ring.
  • Preferred bicyclic compounds of the general formula I are those in which:
  • radicals R 1 to R 3 are methyl groups, the radical R 4 is a hydrogen atom and n is the number 0 and there is a double bond between the C atoms C-1 and C-2 or
  • radicals R 1 to R 4 are methyl groups
  • Y and the radical R 5 are hydrogen and n and m are the number 0 and the six-membered ring formed from the atoms C-1 to C-6 is an aromatic ring or
  • radicals R 1 to R 4 are methyl groups
  • Y and the radical R 5 are hydrogen
  • n is the number 1 and m is the number 0 and the six-membered ring formed from the atoms C-1 to C-6 is an aromatic ring
  • the radicals R 1 and R 2 are methyl groups
  • A is an oxygen atom
  • Y and the radical R 5 are hydrogen
  • n is the number 1 and m is the number 0 and the six-membered ring formed from the atoms C-1 to C-6 is an aromatic ring.
  • Another object of the invention is the preparation of the bicyclic compounds of general formula I.
  • A is a group -CHR 3 R 4 or an oxygen atom
  • radicals R 1 to R 5 are hydrogen or methyl groups
  • - n is the number 0 or 1
  • the radical R 6 is one of the groups -CH 2 OH, -CO 2 H, -CO 2 R 7 or -COR 7 ,
  • the radical R 7 is an alkyl group with 1 to 4 carbon atoms and
  • A is a group -CHR 3 R 4 or an oxygen atom
  • one of the radicals D or E represents a hydrogen atom and the other represents a group -CHR 5 -G,
  • radicals R 1 to R 5 are hydrogen or methyl groups
  • - n is the number 0 or 1
  • the six-membered ring formed from the atoms C-1 to C-6 can contain one or two double bonds or is an aromatic ring with a nucleophile of the general formula IIIa or IIIb,
  • HX-C 6 H 4 -COR 7 (Illb) where X is an oxygen or sulfur atom or a group NH and m is one of the numbers 0 or 1 and, if appropriate, further modification of the alkyl esters by hydrolysis to free acid, reduction to Alcohol and / or - if X represents a sulfur atom - its oxidation to the group SO or SO 2 and R 7 denotes an alkyl group with 1 to 4 carbon atoms.
  • G preferably represents a chlorine, bromine, tosyl or mesyl radical.
  • Another object of the invention is the use of bicyclic compounds of general formula I as antiseborrheic agents for the production of topical, pharmaceutical and cosmetic preparations with sebosuppressive activity.
  • the bicyclic compounds of the formula I have a pronounced sebosuppressive effect, with many products having a noticeably sebostatic or antiseborrheic effect on the skin even at very low application concentrations. They also have good skin and mucous membrane tolerance.
  • the invention therefore furthermore relates to antiseborrheic preparations for topical use on the hair or on the skin, consisting of antiseborrheic active ingredients in a dermatologically tolerated cosmetic or pharmaceutical carrier, characterized in that at least one compound of the general formula I in an amount as the antiseborrheic active ingredient from 0.005 to 1.0 wt .-% based on the total preparation is included. They can be easily incorporated into various pharmaceutical and cosmetic carriers. Such preparations can also be used to advantage in the treatment of various forms of skin disorders such as acne, psoriosis or dandruff.
  • All preparations suitable for application to the hair or skin are suitable as carriers.
  • aqueous or alcoholic solutions, lotions containing surfactants, oils, ointments, emulsions, creams, gels and stick preparations are suitable for skin treatment.
  • Hair lotions, hair shampoos, hair treatments, hair rinses and hair sprays are particularly suitable for the hair treatment. Because of the special cosmetic problems caused by oily hair, the hair cosmetic accessories representations particularly preferred embodiments of the invention.
  • oil components e.g. Paraffin oil, vegetable oils, fatty acid esters, squalane, fatty alcohols, 2-octyldodecanol,
  • fats and waxes e.g. Whale, beeswax, montan wax, paraffin, cetyl stearyl alcohol,
  • emulsifiers e.g. Fatty acid partial glycerides, fatty acid sorbitan partial esters and their ethoxylates, soaps, fatty alcohol sulfates, fatty alcohol polyglycol ethers, alkyl phosphates,
  • detergent raw materials in particular anionic surfactants, for example fatty alcohol polyglycol ether sulfates, fatty alcohol sulfates, alpha olefin sulfonates, alkane sulfonates, sulfosuccinic acid esters, acyl taurides, acyl isethionates and acyl sarcosides, ampholytic surfactants, for example N-alkylglycine, N-alkylaminopropobutyl acid, N-alkylaminopropobutyl acid, N-alkylaminopropionic acid, N-alkylaminopropionic acid, N-alkylaminopropionic acid, N-alkylaminopropionic acid, N-alkylaminopropionic acid, N-alkylaminopropionic acid, N-alkylaminopropionic acid, N-alkylaminopropionic acid, N-alkylaminopropionic acid
  • polyhydric alcohols such as Ethylene glycol, propylene glycol, glycerin, g) water and auxiliaries such as e.g. Fragrances, preservatives, buffer substances, thickeners, dyes and opacifiers.
  • the keto group of the atrinone can be converted into a hydroxyl function by chemical reduction with, for example, sodium bis (2-methoxyethoxy) aluminum dihydride, Vitride R.
  • This hydroxyl function can be converted into a chloride function by methods known from the literature, for example using methanesulfonyl chloride and lithium chloride.
  • the chloride Ila thus prepared provides
  • Example 2-1 By reaction of the chloride Ila with the nucleophile 4-hydroxybenzoic acid methyl ester, the compound of Example 2-1 according to the invention was obtained, which can be converted into the compound according to the invention of Example 2-2 by converting its methyl ester group into a carboxyl group.
  • the compounds of Examples 2-3 to 2-5 were prepared analogously.
  • Example 2-1 4- ⁇ 1- [1,1,3 (1,3,3) -trimethyl-5,6,7,7a-tetrahydroindan-6 (7) -yl] -ethoxy ⁇ -benzoic acid methyl ester (1st ).
  • Example 2-2 4- ⁇ 1- [1,1,3 (1,3,3) -trimethyl-5,6,7,7a-tetrahydroindan-6 (7) -yl] -ethoxy ⁇ -benzoic acid (2nd )
  • Example 2-3 4- ⁇ 1- [1,1,3 (1,3,3) trimethyl-5,6,7,7a-tetrahydroindan-6 (7) -yl] ethoxy ⁇ cinnamic acid (3)
  • Example 2-4 3- ⁇ 1- [1,1,3 (1,3,3) trimethyl-5,6,7,7a-tetrahydroindan-6 (7) -yl] -methoxy ⁇ -benzoic acid (4th )
  • Example 2-5 4- ⁇ 1- [1,1,3 (1,3,3) trimethyl-5,6,7,7a-tetrahydroindan-6 (7) -yl] methoxy ⁇ cinnamic acid (5th )
  • Example 2-6 4- (1,1,3,3-Tetramethylindan-5-yImethoxy) benzoic acid methyl ester (6)
  • Example 2-7 4- (1,1,3,3-Tetramethylindan-5-yImethoxy) benzoic acid
  • Example 2-8 4- (1,1,3,3-Tetramethylindan-5-yImethoxy) benzyl alcohol (8)
  • Example 2-9 4- (1,1,4,4-Tetramethyltetralin-6-ylmethoxy) -benzoic acid methyl ester (9)
  • the halogen compound being 6-bromomethyl-1,1,4,4-tetramethyltetralin (boiling point: 104 ° C./0.1 mbar), which is obtained by free radical bromination of 1,1,4,4 , 6-Pentamethyltetralin (melting point: 32 - 33 ° C) accessible with N-bromosuccinimide was used.
  • Example 2-10 4- (1,1,4,4-Tetramethyltetralin-6-yImethoxy) benzoic acid (10)
  • Example 2-11 4- (1,1,4,4-tetramethyltetralin-6-yImethoxy) benzyl alcohol (11)
  • Example 2-12 4- (1,1,4,4-tetramethyltetralin-6-ylmethoxy) acetophenone (12)
  • Example 2-13 4- (1,1,4,4-tetramethyltetralin-6-ylmethylamino) methyl benzoate (13)
  • Example 2-16 4- (1,1,4,4-tetramethyltetralin-6-ylmethylsulfinyl) methyl benzoate (16)
  • Example 2-2 The methyl ester was obtained analogously to Example 2-1, 6 (7) -chloromethyl-4,4-dimethylchroman being used as the halogen compound, which was obtained by chloromethylation of 4,4-dimethylchromane in benzene with hydrogen chloride and paraformaldehyde.
  • the test is based on the observation that male rats secrete a brownish skin fat, so that the more or less severe oiliness of the skin can be assessed visually as a tan.
  • the fact that the tanning is skin surface fat can be seen from the fact that young female rats and male rats after washing with surfactant solutions or with lipid solvents or male rats which have been systematically treated with estrogen, only after the normal light pink skin have the scissors. At the same time, only very small amounts of lipid can be extracted from the cut hair (see also J. Soc. Cosmet. Chem. 1983 (34) 127).
  • test substances in the concentrations given in Table 1 in ethanol / acetone (1: 1) were brushed on each side of 6 rats on the back skin. The other side was only treated with the solvent.
  • the sebum reduction is calculated from the point difference in such a way that the quotient of the point difference ⁇ P and the number of points for the control group P k is formed and the value obtained is given in%.
  • the inhibitory effect of a test substance on the enzymes GDH, G6-PDH and GPT can therefore be regarded as a measure of the sebostatic activity of a substance.
  • GDH G6-PDH, GPT, tris (hydroxymethyl) aminomethane, triethanolamine hydrochloride, dihydroxyacetone phosphate dimethyl ketal, ß-nicotonamide adenine dinucleotide (NADH), ß-nicotinamide adenine dinucleotide phosphate
  • the ion exchanger used was: DOWEX 50 WX8, from Serva / Heidelberg
  • sample glasses were mixed well on a shaker and incubated in a water bath at 37 ° C for 30 minutes. 5 minutes before the end of the incubation, 6 glasses of substrate batch were heated to 37 ° C. After incubation, each enzyme batch was mixed and 100 ⁇ l of it pipetted to the substrate batch, mixed and transferred to 1.5 ml disposable cuvettes.
  • e) Measurement The absorbance was measured using a Beckmann DU 64 spectrophotometer with an integrated 6-fold sample changer at a temperature of 37 ° C. and a wavelength of 340 nm.
  • Enzyme inhibition 100 (%)
  • the absorbance measurements were evaluated electronically by connecting a microcomputer (Labtop T 3200 from Toshiba) to the photometer via a serial interface.
  • a) Buffer 4.65 g of triethanolamine hydrochloride were dissolved in 400 ml of bidistilled water and the pH was adjusted to 7.6 by adding NaOH or HC1. The mixture was then made up to 500 ml with water (triethanolamine buffer, 50 mmol; pH 7.6).
  • Substrate The dihydroxyacetone phosphate was supplied as dimethyl ketal and had to be hydrolyzed before use. DOWEX ion exchangers were slurried in a beaker with double-distilled water and the deposited ion exchanger was separated. 30 mg of the ketal was dissolved in 3 ml of double-distilled water and after adding 0.6 ml of ion exchanger, the mixture was shaken for 1 minute.
  • the pH was 2 and was adjusted if necessary by adding D0WEX. It was suctioned off through a micro-glass suction filter and rinsed with bidistilled water. The filtrate was made up to 10 ml and incubated in reaction tubes in 1 ml portions for 6 hours at 37 ° C. The solutions were then stored at -60 ° C until use.
  • Myritol (R) 318 Caprylic / capric acid triglyceride (Henkel KGaA) (4-10) Eutanol (R) G: 2-0ctyldodecanol (Henkel KGaA)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Des composés bicycliques ont la formule générale (I), dans laquelle A désigne un groupe -CHR3R4 ou un atome d'oxygène; un des résidus Y ou Z désigne un atome d'hydrogène et l'autre un groupe -CHR5-X-C6H4-(CH=CH)m-R6; où X désigne un des groupes 0, NH, S, SO ou SO¿2? et m est égal à 0 ou 1; les résidus R?1 à R5¿ désignent hydrogène ou des groupes méthyle; n est égal à 0 ou 1; le résidu R6 désigne un des groupes -CH¿2?OH, -CO2H, -CO2R?7¿ ou -COR7; le résidu R7 désigne un groupe alkyle avec 1 à 4 atomes de C; et le noyau à six éléments formé par les atomes C¿1? à C6 contient une ou deux liaisons doubles ou forme un cycle aromatique. Ces composés sont utiles comme suppresseurs de sébum dans des compositions cosmétiques ou pharmaceutiques à application topique sur les cheveux et sur la peau.
PCT/EP1991/001948 1990-10-22 1991-10-14 Composes bicycliques a effet anti-seborrheique WO1992006946A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4033568.2 1990-10-22
DE4033568A DE4033568A1 (de) 1990-10-22 1990-10-22 Bicyclische verbindungen mit antiseborrhoischer wirkung

Publications (1)

Publication Number Publication Date
WO1992006946A1 true WO1992006946A1 (fr) 1992-04-30

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PCT/EP1991/001948 WO1992006946A1 (fr) 1990-10-22 1991-10-14 Composes bicycliques a effet anti-seborrheique

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EP (1) EP0555265A1 (fr)
DE (1) DE4033568A1 (fr)
WO (1) WO1992006946A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995024896A3 (fr) * 1994-03-15 1995-11-09 Unilever Plc Utilisation d'antagonistes d'egf ou de tgf-alpha pour le traitement et la prophylaxie de l'acne
WO2002002069A3 (fr) * 2000-06-30 2002-06-27 Unilever Plc Compositions cosmetiques contenant des derives d'amine substitues

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3028417A1 (de) * 1980-07-26 1982-02-25 Basf Ag Neue veraetherte p-hydroxyzimtsaeureester, ihre herstellung und diese enthaltende zubereitungen als lichtschutzmittel
DE3321662A1 (de) * 1982-06-24 1983-12-29 F. Hoffmann-La Roche & Co AG, 4002 Basel Polyenverbindungen
EP0176035A2 (fr) * 1984-09-22 1986-04-02 BASF Aktiengesellschaft Dérivés de tétraline substitués en pisition 1, leur préparation et utilisation
DE3738407A1 (de) * 1987-11-12 1989-05-24 Henkel Kgaa Sebosuppressive topische zubereitungen
EP0382078A1 (fr) * 1989-02-10 1990-08-16 BASF Aktiengesellschaft Composés céto-aromatiques, leur préparation et médicaments ainsi que cosmétiques les contenant
EP0404640A1 (fr) * 1989-06-13 1990-12-27 L'oreal Nouveaux dérivés de tétrahydro-5,6,7,8 naphtalénol-1, leur procédé de préparation et leur utilisation en tant qu'agents antioxydants dans des compositions cosmétiques et pharmaceutiques les contenant
EP0435681A1 (fr) * 1989-12-29 1991-07-03 Allergan, Inc. Chromane esters de phenols et acides benzoique ayant une activité retinoidique ressemblante

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3028417A1 (de) * 1980-07-26 1982-02-25 Basf Ag Neue veraetherte p-hydroxyzimtsaeureester, ihre herstellung und diese enthaltende zubereitungen als lichtschutzmittel
DE3321662A1 (de) * 1982-06-24 1983-12-29 F. Hoffmann-La Roche & Co AG, 4002 Basel Polyenverbindungen
EP0176035A2 (fr) * 1984-09-22 1986-04-02 BASF Aktiengesellschaft Dérivés de tétraline substitués en pisition 1, leur préparation et utilisation
DE3738407A1 (de) * 1987-11-12 1989-05-24 Henkel Kgaa Sebosuppressive topische zubereitungen
EP0382078A1 (fr) * 1989-02-10 1990-08-16 BASF Aktiengesellschaft Composés céto-aromatiques, leur préparation et médicaments ainsi que cosmétiques les contenant
EP0404640A1 (fr) * 1989-06-13 1990-12-27 L'oreal Nouveaux dérivés de tétrahydro-5,6,7,8 naphtalénol-1, leur procédé de préparation et leur utilisation en tant qu'agents antioxydants dans des compositions cosmétiques et pharmaceutiques les contenant
EP0435681A1 (fr) * 1989-12-29 1991-07-03 Allergan, Inc. Chromane esters de phenols et acides benzoique ayant une activité retinoidique ressemblante

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995024896A3 (fr) * 1994-03-15 1995-11-09 Unilever Plc Utilisation d'antagonistes d'egf ou de tgf-alpha pour le traitement et la prophylaxie de l'acne
WO2002002069A3 (fr) * 2000-06-30 2002-06-27 Unilever Plc Compositions cosmetiques contenant des derives d'amine substitues

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Publication number Publication date
EP0555265A1 (fr) 1993-08-18
DE4033568A1 (de) 1992-04-23

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