EP0689431A1 - Nouvelle utilisation d'agents anti-acne - Google Patents

Nouvelle utilisation d'agents anti-acne

Info

Publication number
EP0689431A1
EP0689431A1 EP94911877A EP94911877A EP0689431A1 EP 0689431 A1 EP0689431 A1 EP 0689431A1 EP 94911877 A EP94911877 A EP 94911877A EP 94911877 A EP94911877 A EP 94911877A EP 0689431 A1 EP0689431 A1 EP 0689431A1
Authority
EP
European Patent Office
Prior art keywords
preparations
acid
weight
acne
cosmetic
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.)
Withdrawn
Application number
EP94911877A
Other languages
German (de)
English (en)
Inventor
Gerhard Sauermann
Franz STÄB
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.)
Beiersdorf AG
Original Assignee
Beiersdorf AG
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 Beiersdorf AG filed Critical Beiersdorf AG
Publication of EP0689431A1 publication Critical patent/EP0689431A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • 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
    • A61K31/60—Salicylic acid; Derivatives thereof
    • 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
    • A61K31/65—Tetracyclines
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/38—Percompounds, e.g. peracids
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • A61K8/63—Steroids; Derivatives thereof
    • 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
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61Q19/005—Preparations for sensitive skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • the present invention relates to active ingredients and preparations which serve for the prophylaxis and treatment of light-sensitive skin, in particular photodermatoses.
  • UVC range rays with a wavelength shorter than 290 nm
  • UVB range rays in the range between 290 nm and 320 nm, the so-called UVB range, cause erythema simple sunburn or even more or less severe burns.
  • the narrower range around 308 nm is given as a maximum of the erythema effectiveness of sunlight.
  • Numerous compounds are known for protection against UVB radiation, which are derivatives of 3-benzylidene camphor, 4-aminobenzoic acid, cinnamic acid, salicylic acid, benzophenone and also 2-phenylbenzimidazole.
  • UVA range It is also important for the range between about 320 nm and about 400 nm, the so-called UVA range, To have filter substances available because their rays can cause reactions in light-sensitive skin. It has been proven that UVA radiation damages elastic and collagen fibers. it carries connective tissue, which causes the skin to age prematurely, and that it can be seen as the cause of numerous phototoxic and photoallergic reactions. The damaging influence of UVB radiation can be intensified by UVA radiation.
  • UV radiation can also lead to photochemical reactions, in which case the photochemical reaction products intervene in the skin metabolism.
  • Such photochemical reaction products are predominantly free radical compounds, for example hydroxy radicals.
  • Undefined radical photo products which arise in the skin itself can also display uncontrolled subsequent reactions due to their high reactivity.
  • singlet oxygen a non-radical excited state of the oxygen molecule can occur with UV radiation, just as short-lived epoxies and many others.
  • Singlet oxygen for example, is characterized by increased reactivity compared to the triplet oxygen that is normally present (basic radical state).
  • UV radiation also belongs to ionizing radiation. There is therefore a risk that ionic species also develop when exposed to UV rays, which in turn can oxidatively intervene in the biochemical processes.
  • antioxidants and / or free radical scavengers can be incorporated into the cosmetic or dermatological formulations.
  • vitamin E a substance with a known antioxidative effect, in light protection formulations, but the effect achieved here also falls far short of the hoped-for effect.
  • the object of the invention is to provide cosmetic, dermatological and pharmaceutical active substances and preparations as well as light protection formulations which are used for the prophylaxis and treatment of light-sensitive skin, in particular photodermatoses, preferably PLD.
  • the invention also relates to the mixtures of the active substances and preparations therewith. Preparations according to the invention which contain a UV protective agent are particularly preferred.
  • Acne agents or acne active ingredients are known in large numbers. It can be cosmetic, dermatological and pharmaceutical active ingredients which e.g. can be administered orally, parenterally or topically. Their effect according to the invention is surprising since there are no indications of an effect in photodermatoses. The term “Mallorca acne” is misleading in this context, since this so-called “acne” is not one of the acne forms.
  • Preferred acne active ingredients are vitamin A and derivatives, antibiotics from the acne treatment spectrum such as clindamycin and tratracyclines, but especially those which have antibacterial activity against propionibacteria, keratolytics such as salicylic acid and alpha-hydroxy acids and preparations, in particular topical preparations with them .
  • Benzoyl peroxide and in particular also topical preparations are particularly preferred.
  • Benzoyl peroxide and preparations with it, together with an antibacterial agent are preferred. in particular an antibacterial acne agent used.
  • the acne agents are used in the same way as in the acne treatment and in the preparations known in the process.
  • agents against acne or propionibacteria or comedones are particularly preferred:
  • Vitamin A acid (all-trans retinoic acid) e.g. in
  • Benzoyl peroxide e.g. in topical preparations such as emulsions, gels, creams, preferably with 0.5 to 20 wt .-%, in particular 2.5 to 10 wt .- /. salary
  • topical antibiotics such as
  • Salicylic acid e.g. in topical preparations with 1 to 10% by weight
  • Azelaic acid for example in creams with 1 to 20% by weight, preferably 15 20 6% by weight of active substance, oral antibiotics such as
  • Tretracyclines, macrolides e.g. Doxycycline, minocycline, erythromycin, josamycin, e.g. with daily doses of 50 to 1500 mg
  • Isotretinoin e.g. with daily doses of 2.5 to 40 mg
  • Vitamin A retinol
  • Retinol palmitate applied topically, e.g. in solutions,
  • Cyproterone acetate e.g. with daily doses of 5 to 100 mg.
  • the acne agents used according to the invention preferably also contain antioxidants.
  • Preferred antioxidants are thiols, e.g. Cysteine and cysteine derivatives, glutathione, cystine, N-acetylcysteine, lipoic acid, folic acid, ubiquinone, phytic acid, alpha-hydroxy acids such as e.g. Citric acid and lactic acid, zinc sulfate, zinc oxide, vitamin C, vitamin E, carotene.
  • thiols e.g. Cysteine and cysteine derivatives, glutathione, cystine, N-acetylcysteine, lipoic acid, folic acid, ubiquinone, phytic acid, alpha-hydroxy acids such as e.g. Citric acid and lactic acid, zinc sulfate, zinc oxide, vitamin C, vitamin E, carotene.
  • the cosmetic or dermatological preparations according to the invention contain antioxidants, for example in amounts of 0.01% by weight to 10% by weight, preferably in amounts of 0.5% by weight to 6% by weight, but in particular 2 % By weight to 4% by weight based on the total weight of the preparations.
  • the active substances according to the invention and the preparations obtained therewith have a prophylactic effect in that they protect the light-sensitive skin and prevent or reduce the formation of PLD. For this purpose, they are used before sun exposure.
  • Photodermatoses and manifest PLE take place in the treatment with the active substances and preparations according to the invention, an improvement in the skin conditions and a faster decay, e.g. the PLD or the photodermatosis.
  • Cosmetic and dermatological preparations which are in the form of a sunscreen are particularly preferred. These preferably additionally contain at least one UVA filter and / or at least one further UVB filter and / or at least one inorganic pigment.
  • Cosmetic and dermatological preparations according to the invention for protecting the skin from UV rays can be in various forms, such as those e.g. are usually used for this type of preparation. So you can e.g. a solution, an emulsion of the type water-in-oil (W / 0) or of the type oil-in-water (0 / W), or a multiple emulsions, for example of the type water-in-oil-in-water (W / O / W), a gel, a solid stick or an aerosol.
  • the cosmetic and dermatological preparations according to the invention can contain cosmetic auxiliaries of the kind normally used in such preparations, for example preservatives, bactericides, perfumes, substances for preventing foaming, dyes, pigments which have a coloring effect, Thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or moisturizing substances, fats, oils, waxes or other usual components of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • cosmetic auxiliaries of the kind normally used in such preparations, for example preservatives, bactericides, perfumes, substances for preventing foaming, dyes, pigments which have a coloring effect, Thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or moisturizing substances, fats, oils, waxes or other usual components of a cosmetic or dermatological formulation such as alcohols, polyols
  • the cosmetic or dermatological preparation is a solution or lotion, ⁇ .B. used as solvents:
  • Oils such as triglycerides of capric or caprylic acid, but preferably castor oil;
  • Fats, waxes and other natural and synthetic fat bodies preferably esters of fatty acids with alcohols of low C number, e.g. with isopropanol, propylene glycol or glycerin, or esters of fatty alcohols with low C number alkanoic acids or with fatty acids;
  • ethers preferably ethanol, isopropanol, propylene glycol, glycerin, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol onomethyl or monoethyl ether and analog products.
  • Emulsions according to the invention for example in the form of a sunscreen cream or sunscreen milk, are preferred and contain, for example, the fats, oils, waxes and other fat bodies mentioned, as well as water and an emulsifier, as is customarily used for such a type of formulation.
  • Gels according to the invention usually contain low C number alcohols, e.g. Ethanol, isopropanol, 1,2-propanediol, glycerol and water or an oil mentioned above in the presence of a thickener, which is preferred in the case of oily-alcoholic gels, preferably silicon dioxide or an aluminum silicate, in the case of aqueous-alcoholic or alcoholic gels is a polyacrylate.
  • low C number alcohols e.g. Ethanol, isopropanol, 1,2-propanediol, glycerol and water or an oil mentioned above in the presence of a thickener, which is preferred in the case of oily-alcoholic gels, preferably silicon dioxide or an aluminum silicate, in the case of aqueous-alcoholic or alcoholic gels is a polyacrylate.
  • Fixed pins according to the invention contain e.g. natural or synthetic waxes, fatty alcohols or fatty acid esters. Lip care sticks are preferred.
  • Suitable blowing agents for cosmetic deodorants according to the invention which can be sprayed from aerosol containers are the customary, known volatile, liquefied blowing agents, for example hydrocarbons (propane, butane, isobutane), which can be used alone or in a mixture with one another. Compressed air can also be used advantageously.
  • hydrocarbons propane, butane, isobutane
  • the topical preparations according to the invention can preferably also contain substances which absorb UV radiation in the UVA and / or in the UVB range, the total amount of the filter substances being, for example, 0.1% by weight to 30% by weight, preferably 0.5 to 10 wt. , in particular 1 to 6% by weight, based on the total weight of the preparations, in order to provide cosmetic preparations which protect the skin from the entire range of ultraviolet radiation. They can also serve as sunscreens.
  • the UVB filters can be oil-soluble or water-soluble.
  • oil-soluble substances e.g. to call:
  • 3-benzylidene camphor derivatives preferably 3- (4-methylbenzylidene) camphor, 3-benzylidene camphor;
  • 4-aminobenzoic acid derivatives preferably 4- (dimethylamino) benzoic acid (2-ethylhexyl) ester, 4- (dimethylamino) benzoic acid amyl ester;
  • esters of cinnamic acid preferably 4-methoxycinnamic acid (2-ethylhexyl) ester, 4-methoxycytic acid isopentyl ester;
  • esters of salicylic acid preferably salicylic acid (2-ethylhexyl) ester, salicylic acid (4-isopropylbenzyl) ester, salicylic acid homomethyl ester;
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
  • Esters of benzalmalonic acid preferably 4-methoxybenzalmalonic acid di (2-ethylhexyl) ester;
  • UVB filters should, of course, not be limiting.
  • the invention also relates to preparations according to the invention with combinations of a UVA filter with a UVB filter or cosmetic or dermatological preparations according to the invention which also contain a UVB filter.
  • UVA filters which have hitherto usually been contained in cosmetic preparations.
  • These substances are preferably derivatives of dibenzoylmethane, in particular 1- (4'- tert-Butylphenyl) -3- (4'-methoxyphenyl) propane-1, 3-dione and 1-phenyl-3- (4 '-isopropylphenyl) propane-1, 3-dione.
  • Cosmetic and dermatological preparations according to the invention can also contain inorganic pigments which are usually used in cosmetics to protect the skin from UV rays. These are oxides of titanium, zinc, iron, zirconium, silicon, manganese, aluminum, cerium and mixtures thereof, as well as modifications in which the oxides are the active agents. It is particularly preferred to use pigments based on titanium dioxide. These combinations of UVA filter and pigment or preparations containing this combination are also the subject of the invention. The amounts given for the above combinations can be used.
  • the invention also relates to the process for the production of the cosmetic compositions according to the invention, which is characterized in that the active ingredients according to the invention are incorporated into cosmetic and dermatological formulations in a manner known per se.
  • the preparations are prepared in a manner known per se, in particular by mixing the constituents, if appropriate at elevated temperature. Fat and water phase are produced separately and mixed or emulsified if necessary at elevated temperature.
  • a mixture of 6.3% by weight of wool wax alcohols and 6.5% by weight of paraffin oil is added to the fat phase at 75 ° C.
  • the fat phase is then added to the 75 ° C warm water phase, stirred and homogenized until a uniform white cream has formed.
  • Example I has the following final composition:
  • Fat phase wt. . -%
  • the fat phase at 75 ° C. is added to the water phase at 75 ° C., stirred and homogenized until a uniform white cream has formed.
  • game III
  • a hydrogel is produced in the usual way with the constituents mentioned.
  • Carbomer 5984 (B.F. Goodrich) 0.25%
  • a gel is produced with the ingredients in the usual way.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

Des agents actifs ou des préparations qui sont utilisés ou conviennent pour le traitement de l'acné peuvent s'utiliser pour la prophylaxie ou le traitement des peaux photosensibles, notamment des photodermatoses, et de préférence de la photodermatose polymorphe.
EP94911877A 1993-03-15 1994-03-11 Nouvelle utilisation d'agents anti-acne Withdrawn EP0689431A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4307976A DE4307976A1 (de) 1993-03-15 1993-03-15 Neue Verwendung von Aknemitteln
DE4307976 1993-03-15
PCT/EP1994/000769 WO1994021241A1 (fr) 1993-03-15 1994-03-11 Nouvelle utilisation d'agents anti-acne

Publications (1)

Publication Number Publication Date
EP0689431A1 true EP0689431A1 (fr) 1996-01-03

Family

ID=6482681

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94911877A Withdrawn EP0689431A1 (fr) 1993-03-15 1994-03-11 Nouvelle utilisation d'agents anti-acne

Country Status (4)

Country Link
EP (1) EP0689431A1 (fr)
JP (1) JPH08507772A (fr)
DE (1) DE4307976A1 (fr)
WO (1) WO1994021241A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19533330A1 (de) * 1995-09-11 1997-03-13 Beiersdorf Ag Gegen Hautkrebs wirksame topische Zubereitungen
DE19537027A1 (de) * 1995-10-05 1997-04-10 Beiersdorf Ag Hautpflegemittel für alte Haut
US6262117B1 (en) * 1999-02-18 2001-07-17 Allergan Sales, Inc. Method and composition for treating acne
US6596209B2 (en) 2000-08-10 2003-07-22 California Agriboard Llc Production of particle board from agricultural waste
CA2600762C (fr) * 2005-03-10 2011-05-31 Jr Chem, Llc Compositions de peroxyde organique stables
MY165887A (en) * 2012-01-20 2018-05-18 Kao Corp Cosmetic composition

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FR2096712A1 (en) * 1970-06-29 1972-02-25 Giraux Georges Steroid/b group vitamin compsns - for prevention and treatment of skin-photosensitivity disorders
US4021538A (en) * 1975-09-29 1977-05-03 Yu Ruey J Method for producing pigmentation in hair or skin
US4318907A (en) * 1978-04-04 1982-03-09 Westwood Pharmaceuticals, Inc. Method for treating acne vulgaris and compositions useful for that purpose
US4256763A (en) * 1978-09-19 1981-03-17 Mchugh John E Treatment of herpes simplex infections and acne
US4588744A (en) * 1978-09-19 1986-05-13 Mchugh John E Method of forming an aqueous solution of 3-3-Bis(p-hydroxyphenyl)-phthalide
US5008294A (en) * 1985-02-11 1991-04-16 Chemex Pharmaceuticals, Inc. Methods of treating tumors with compositions of catecholic butanes
FR2501044A1 (fr) * 1981-03-04 1982-09-10 Machugh John Medicament a base de 3,3-bis-(p-hydroxyphenyl)-phtalide et son procede de preparation
FR2514643B1 (fr) * 1981-10-20 1986-07-04 Oreal Lanolate de cuivre et compositions cosmetiques anti-acneiques le contenant
LU85111A1 (fr) * 1983-12-01 1985-09-12 Oreal Composition anti-acnetique a base de peroxyde de benzoyle et d'au moins un filtre solaire
LU86258A1 (fr) * 1986-01-21 1987-09-03 Rech Dermatologiques C I R D S Composes benzamido aromatique,leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique
CA1315803C (fr) * 1988-04-22 1993-04-06 Joseph P. Ciaudelli N-alkoxyalkylamides d'hydroxyacides et compositions pour le traitement de la peau en contenant
KR930001805B1 (ko) * 1989-10-02 1993-03-13 브리스톨-마이어즈 스퀴브 컴페니 안정성이 개선된 트리티노인 유화크림 제제

Non-Patent Citations (1)

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See references of WO9421241A1 *

Also Published As

Publication number Publication date
DE4307976A1 (de) 1994-09-22
WO1994021241A1 (fr) 1994-09-29
JPH08507772A (ja) 1996-08-20

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