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WO1992007586A1 - Composition topique comprenant un stimulateur de penetration retinoide - Google Patents

Composition topique comprenant un stimulateur de penetration retinoide Download PDF

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Publication number
WO1992007586A1
WO1992007586A1 PCT/GB1991/001874 GB9101874W WO9207586A1 WO 1992007586 A1 WO1992007586 A1 WO 1992007586A1 GB 9101874 W GB9101874 W GB 9101874W WO 9207586 A1 WO9207586 A1 WO 9207586A1
Authority
WO
WIPO (PCT)
Prior art keywords
retinoid
group
active substance
topically active
compound
Prior art date
Application number
PCT/GB1991/001874
Other languages
English (en)
Inventor
Benjamin Digby Ridge
Walter Brian Davis
Original Assignee
Beecham Group Plc
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
Priority claimed from GB909023648A external-priority patent/GB9023648D0/en
Priority claimed from GB909023647A external-priority patent/GB9023647D0/en
Application filed by Beecham Group Plc filed Critical Beecham Group Plc
Priority to JP3517418A priority Critical patent/JPH06502161A/ja
Publication of WO1992007586A1 publication Critical patent/WO1992007586A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • 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
    • 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
    • A61Q7/00—Preparations for affecting hair growth

Definitions

  • Topical composition with retinoid penetration enhancer Topical composition with retinoid penetration enhancer
  • the invention relates to a method of increasing the
  • vitamin A retinol
  • retinol and other retinoid compounds including retinoic acid
  • both retinol and retinoic acid have been used in the treatment of acne.
  • retinoic acid is described as having utility in reversing the ageing process that occurs in the skin, mediated both intrinsically as a factor of increasing age and extrinsically, for example by prolonged exposure to sunlight.
  • WO 82/02833 (BAZZANO) describes the use of retinoid compounds as
  • retinol esters a specific class of retinoid compounds, in increasing the diameter of growing hair and their use in hair-care compositions.
  • retinoid compounds in combination with other topically active materials has been disclosed.
  • BAZZANO WO 83/02558
  • WO 83/02558 describes the use of retinoid compounds in combination with the compound minoxidil which compound is marketed as a topically administrable stimulant of hair-growth.
  • the combination of a retinoid compound and minoxidil produces a 'synergistic' effect; i.e. the combination produces an effect which cannot be produced by either compound separately.
  • the 'synergism' is attributed to the different but complementary modes of action of the retinoid component and minoxidil on hair-growth.
  • Minoxidil is described as initiating and promoting vellus hair growth on the scalp and the retinoid is described as acting to sustain the growth of terminal hairs from vellus hairs on the scalp.
  • the retinoid compound in compositions according to 'Bazzano' is acting as a topically active agent per se
  • Preparations according to US 4,727,088 comprise a novel vehicle system which system delivers an active ingredient to the site of action in a form whereby bioavailability and percutaneous absorption are enhanced.
  • retinoic acid is disclosed as the active ingredient having anti-acne activity.
  • the retinoid compound is acting as a topically active agent per se rather than contributing to the vehicle system which promotes enhanced bioavailability and percutaneous absorption.
  • retinoid compounds are themselves able to enhance bioavailability and percutaneous absorption of topically active substances and hence synergise the effect of topically active substances.
  • a method of enhancing the bioavailability and percutaneous absorption of a topically active substance comprises the topical administration to the skin and/or scalp of an effective amount of a composition comprising a penetration enhancer in the form of a retinoid compound, and a topically active substance which is other than a retinoid compound.
  • topically active substance includes materials which when applied to the skin and/or scalp give rise to a cosmetic and/or therapeutic effect.
  • topically active substance includes materials generally regarded as conferring only cosmetic benefit and also medicaments of therapeutic value. It will of course be appreciated that certain substances, for example anti-acne treatments, may confer both cosmetic and therapeutic
  • compositions suitable for use in the method of the present invention include a retinoid compound and a topically active substance which substance has inter alia utility in the treatment of bacterial, fungal and viral infections; in the treatment of skin disorders such as acne, psoriasis and dermatitis; in the treatment of the effects of skin and tissue damage such as wounds and bruising; and in arresting hair-loss and promoting hair-growth.
  • retinoid compound includes retinoic acid, in particular all trans retinoic acid and derivatives thereof including esters and amides; retinal; retinol and derivatives thereof including ethers and in particular retinol esters. It will be appreciated that the term retinoid compound also includes, where applicable, salts, for example alkali metal salts and alkaline earth metal salts, and also solvates including hydrates.
  • esters unlike retinoic acid, show very little irritancy when applied topically, and, as referred to above, have been shown to confer the additional advantage in a hair-care product of enhancing hair-growth for example by increasing the diameter of growing hair.
  • a composition of the invention comprises at least one C 2-16 alkanoyl ester of retinol.
  • a composition of the invention comprises at least one C 2- 7 straight chain, branched chain or cyclic alkanoyl ester of retinol, for example retinyl acetate, propionate, butyrate, cyclopentanecarboxylate, pivalate, valerate, hexanoate or heptanoate; or retinyl palmitate.
  • a particularly preferred composition comprises the propanoyl or the palmitoyl ester of retinol.
  • compositions for use in the present invention optionally include a topically acceptable carrier and in particular a topically acceptable carrier which enhances the stability of a retinol ester.
  • novel compositions comprising a penetration enhancer in the form of a retinoid compound, in particular a retinyl ester or a mixture of esters of retinol, and a topically active substance other than a retinoid compound, for topical administration.
  • a penetration enhancer in the form of a retinoid compound, in particular a retinyl ester or a mixture of esters of retinol
  • a topically active substance other than a retinoid compound for topical administration.
  • novel compositions for topical administration according to the present invention do not include specific combinations of retinoid compounds and topically active substances which form part of the state of the art, i.e. are available to the public in any way, for example via use or by being specifically described in any printed publication.
  • any specifically identified combination for example those combinations exemplified in WO 83/02558 (Bazzano) are hereby excluded by proviso.
  • a novel composition according to the present invention which is
  • GB 1 538 227 discloses compounds of formula (I)
  • R 1 is a C 1-5 alkyl group, a C 3-6 alkenyl group, a C 3-6 cycloalkyl group, or a phenylalkyl group in which the alkyl moiety contains 1 to 3 carbon atoms and the phenyl moiety is optionally substituted;
  • R 2 is a hydroxyl group, or a group OR4 wherein R 4 is a C 2 - 7 alkanoyl group, a C 1-4 alkyl group, or an optionally substituted benzyl group; and R 3 is
  • R 2 and R 3 together with the carbon atom to which they are joined represent a
  • Optional substituents for phenyl moieties include C 1-4 alkyl, halogen and nitro.
  • R 1 is a methyl, ethyl or n- or iso-propyl group, and most preferably a methyl group.
  • R 2 is a hydroxyl group.
  • Variable R 2 suitably has the ⁇ -configuration.
  • R 3 is hydrogen or methyl, and most preferably hydrogen.
  • R 3 is hydrogen, which is the compound androst-4-ene-16, 16-dimethyl-17 ⁇ -ol-3-one .
  • compositions for use according to the present invention preferably include a topically acceptable carrier which is anhydrous or wherein the retinoid, more especially a retinol ester or mixture thereof, is dissolved in a non-aqueous phase of a multiphase system, which phases, on mixing, may be miscible, or may form an emulsion such as an oil-in-water or water-in-oil type of emulsion.
  • a topically acceptable carrier which is anhydrous or wherein the retinoid, more especially a retinol ester or mixture thereof, is dissolved in a non-aqueous phase of a multiphase system, which phases, on mixing, may be miscible, or may form an emulsion such as an oil-in-water or water-in-oil type of emulsion.
  • the stability of a retinyl ester may be enhanced by
  • incorporation into an aqueous gel such as a carbopol gel.
  • an anhydrous carrier comprises an anhydrous alcohol such as propan-2-ol or ethanol, a volatile oil such as a volatile silicone, or mixtures thereof.
  • an anhydrous alcohol such as propan-2-ol or ethanol
  • a volatile oil such as a volatile silicone, or mixtures thereof.
  • non-aqueous phase of a multiphase system comprises a
  • volatile oil such as a volatile silicone.
  • oils suitable for inclusion in the present compositions include: volatile linear iso-paraffins, acyclic dimethylpolysiloxanes for example dimethylpolysiloxane, cyclic dimethylpoly-siloxanes, mineral oils, vegetable oils, synthetic fatty acid esters, fatty alcohols, lanolin and its derivatives.
  • solvents include volatile alcohols such as ethanol and ⁇ ropan-2-ol and less-volatile alcohols such as benzyl alcohol.
  • compositions for use according to the invention should desirably include an anti-oxidant effective in preventing oxidation of the retinoid compound and consequent reduction in the activity of the composition.
  • an anti-oxidant effective in preventing oxidation of the retinoid compound and consequent reduction in the activity of the composition.
  • Some anti-oxidants are effective in this respect but themselves oxidise to give a noticeable yellowing of the products.
  • Anti-oxidants which are suitable for incorporation include butylated hydroxytoluene (BHT),
  • BHQ tert-butylhydroquinone
  • the invention includes a
  • a sequestering agent in compositions for use according to the invention, for example a metal ion chelator such as citric acid or ethylene diamine tetraacetic acid.
  • a sequestering agent and an anti-oxidant are both present, the sequestering agent will not normally be citric acid when the anti-oxidant is
  • composition for use in accordance with the invention includes a composition for use in accordance with the invention including a sequestering agent.
  • topically active substance is a compound of formula (I), will comprise (w/w) from 0.005 to 5%, preferably 0.5 to 2.5% and more preferably 2% of a compound of formula (I) and from 0.01 to 2%, preferably 0.1 to 1.0% and more preferably 0.2% of a retinoid compound.
  • compositions will optionally include (w/w) from 0.01 to 1% and preferably 0.05 to 0.25% of an anti-oxidant; and from 0.005 to 1%, and preferably 0.008 to 0.02% of a sequestering agent.
  • a typical single-phase formulation will additionally include an anhydrous carrier comprising (w/w) from 80 to 99.5% of an anhydrous solvent or solvent mixture.
  • the terms 'liquid' and 'solution' include viscous materials such as creams, ointments and gels.
  • compositions for use in the present invention may be applied topically to the skin or scalp as appropriate in the form of lotions, ointments, creams, conditioners, gels, mousses, sprays or aerosols. It will however be appreciated that topical compositions will not be limited to the forms indicated above.
  • a composition for topical application to the skin or scalp is preferably a 'leave-on' product, and includes, as
  • conditioners appropriate, conditioners, tonics, lotions, creams, dressings, gels, spray on conditioners, aerosol conditioning sprays, mousses, post foaming hair gels, styling and
  • ingredients may be used.
  • a skin-care product compositions may be used.
  • Gels, conditioners and other hair dressings will contain ingredients conventionally used in the art, and may include emulsifiers, detergents and alcohol.
  • perfumes and dyes may also be used.
  • composition comprising a retinoid compound, more especially an ester of retinol or a mixture of esters of retinol, and a compound of formula (I), in particular
  • compositions will be formulated with
  • topically acceptable carrier materials such that the
  • retinoid component and the formula (I) component are identical to retinoid component and the formula (I) component.
  • a solution substantially saturated and preferably supersaturated in one or both components may be created in situ from a solution which is sub-saturated in one or both components by using a mixture of volatile and non-volatile solvents.
  • the volatile solvent rapidly evaporates thereby increasing the concentration of one or both components to substantially saturated and preferably super-saturated level.
  • volatile solvents include ethanol, propan-2-ol and volatile silicone fluids.
  • non-volatile solvents include propylene glycol, polyethylene glycol, silicone fluids and Arlasolve DM1 (dimethyl iso-sorbide).
  • substantially saturated and preferably supersaturated levels may be achieved by dissolving the active components in the first and/or second of two liquid phases and mixing them together either in situ post-application or immediately prior to use.
  • the composition of the two liquid phases and the concentrations of the active components are selected such that on admixture of the two phases the concentration of one or both active components is near to or greater than the saturated solubility in the initially formed resultant mixture.
  • a retinoid compound which is a retinyl ester will be enhanced if it is dissolved in a non- aqueous second phase.
  • a further solubilising agent will be present in that phase.
  • Suitable anti-nucleating agents include polyvinylpyrrolidone (PVP), carboxymethyl cellulose (CMC), and hydroxypropyl methyl cellulose (HPMC) .
  • the compositions of this invention should desirably include an anti-oxidant effective in preventing oxidation of the retinoid compound and consequent reduction in the activity of the composition. Some anti-oxidants are effective in this respect but themselves oxidise to give a noticeable yellowing of the products.
  • Anti-oxidants which are suitable for incorporation include butylated hydroxytoluene (BHT), (2, 3-di-tert-butyl-p- cresol); butylated hydroxyanisole (BHA), (2-tert-butyl-4- hydroxyanisole or 3-tert-butyl-4-hydroxyanisole); butylated hydroquinone (BHQ); tert-butylhydroquinone (TBHQ); vitamin E acetate; ascorbyl palmitate; and Nipanox (BHA: propyl gallate: citric acid: propylene glycol; 13:13:4:70) or a misture of these.
  • a particularly suitable anti-oxidant is Nipanox. Accordingly in another of its aspects, the
  • composition in accordance with the invention includes a composition in accordance with the invention including an anti-oxidant selected from any of the above.
  • the present invention also provides a composition comprising a retinoid compound, in particular a retinyl ester, and a compound of formula (I), in particular the compound
  • the present invention further provides a composition comprising a retinoid compound, in particular a retinyl ester, and a compound of formula (I), in particular
  • the present invention also provides a composition
  • a composition comprising a retinoid compound, in particular a retinyl ester, and a compound of formula (I), in particular the compound
  • the present invention provides a composition comprising a retinoid compound, in particular a retinyl ester, and a compound of formula (I), in particular the compound androst-4-ene-16, 16- dimethyl-17 ⁇ -ol-3-one for use as a hair-care product and in particular for arresting hair-loss and/or promoting hair-growth.
  • a retinoid compound in particular a retinyl ester
  • a compound of formula (I) in particular the compound androst-4-ene-16, 16- dimethyl-17 ⁇ -ol-3-one for use as a hair-care product and in particular for arresting hair-loss and/or promoting hair-growth.
  • the present invention provides a method of enhancing the bioavailability and percutaneous absorption of a topically active cosmetic substance which method comprises the topical administration to the skin and/or scalp of an effective amount of a composition comprising a penetration enhancer, more especially a retinyl ester or a mixture of esters of retinol, and a topically active cosmetic substance which is other than a retinoid compound.
  • the present invention provides a method of enhancing the bioavailability and percutaneous absorption of a topically active therapeutic substance which method comprises the topical administration to the skin and/or scalp of an effective amount of a composition comprising a penetration enhancer, more especially a retinyl ester or a mixture of esters of retinol, and a topically active
  • a method of treatment of conditions of the human and animal body which are responsive to topically active substances comprises the topical administration of an effective amount of a composition comprising a retinoid compound, in particular a retinyl ester, and a topically active cosmetic and/or therapeutic substance which is other than a retinoid compound.
  • a method of treatment of conditions of the human and animal body which are responsive to topically active substances comprises the topical administration of an effective amount of a composition comprising a retinoid compound, in particular a retinyl ester, and a topically active cosmetic and/or therapeutic substance which is other than a retinoid compound.
  • composition comprising a retinoid compound, in particular a retinyl ester, and a topically active anti-bacterial, anti-fungal or anti-viral substance.
  • a method of treatment of skin disorders in particular acne, psoriasis and dermatitis, which method comprises the topical administration of an effective amount of a composition comprising a retinoid compound, in particular a retinyl ester, and a topically active anti-acne, anti-psoriasis or anti-dermatitic
  • bruising which method comprises the topical administration of an effective amount of a composition comprising a retinoid compound, in particular a retinyl ester, and a topically active substance effective in the healing of skin and tissue damage which is other than a retinoid compound.
  • a composition comprising a retinoid compound, in particular a retinyl ester, and a topically active substance effective in the healing of skin and tissue damage which is other than a retinoid compound.
  • a method of arresting hair-loss and/or promoting hair-growth comprises the topical administration of an effective amount of a composition comprising a retinoid compound, in particular a retinyl ester, and a topically active substance effective in arresting hair-loss and/or promoting hair-growth which is other than a retinoid compound.
  • the present invention provides a method of treating skin-disorders, in particular acne, which method comprises the topical administration to the skin or scalp of an effective amount of a composition comprising a retinoid compound, in particular a retinyl ester, and a compound of formula (I), in particular the compound
  • the present invention provides a method for arresting hair-loss and/or promoting hair-growth which method comprises the topical
  • a composition comprising a retinoid compound, in particular a retinyl ester, and a compound of formula (I), in particular the compound androst-4-ene-16, 16-dimethyl-17 ⁇ -ol-3-one.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)

Abstract

On décrit l'utilisation de rétinoïdes en tant que stimulateurs de pénétration percutanée, ainsi que des compositions topiques de rétinoïdes comprenant des stéroïdes d'androstène disubstitués 16,16. Ces compositions sont utiles à l'enraiement de la chute des cheveux et à la stimulation de la pousse des cheveux.
PCT/GB1991/001874 1990-10-31 1991-10-25 Composition topique comprenant un stimulateur de penetration retinoide WO1992007586A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP3517418A JPH06502161A (ja) 1990-10-31 1991-10-25 レチノイド浸透作用エンハンサーを含む局所用組成物

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB9023647.2 1990-10-31
GB909023648A GB9023648D0 (en) 1990-10-31 1990-10-31 Novel method
GB9023648.0 1990-10-31
GB909023647A GB9023647D0 (en) 1990-10-31 1990-10-31 Novel compositions

Publications (1)

Publication Number Publication Date
WO1992007586A1 true WO1992007586A1 (fr) 1992-05-14

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ID=26297873

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1991/001874 WO1992007586A1 (fr) 1990-10-31 1991-10-25 Composition topique comprenant un stimulateur de penetration retinoide

Country Status (3)

Country Link
EP (1) EP0555309A1 (fr)
JP (1) JPH06502161A (fr)
WO (1) WO1992007586A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995013077A1 (fr) * 1993-11-12 1995-05-18 Merck & Co., Inc. 7β-SUBSTITUES-4-AZA-5α-CHOLESTAN-3-ONES UTILISES COMME INHIBITEURS SELECTIFS DE LA 5α-REDUCTASE 1
FR2718021A1 (fr) * 1994-04-05 1995-10-06 Fabre Pierre Cosmetique Composition topique à base de rétinal.
US5527807A (en) * 1992-05-20 1996-06-18 Merck & Co., Inc. 7β-substituted-4-aza-5α-cholestan-3-ones as 5α reductase inhibitors useful in the prevention and treatment of hyperandrogenetic disorders
EP0786999A1 (fr) * 1994-10-21 1997-08-06 Merck & Co., Inc. Procede combine de traitement de l'acne
EP0792371A1 (fr) * 1994-10-21 1997-09-03 Merck & Co., Inc. Procede combine de traitement de l'acne
WO2004103320A3 (fr) * 2003-05-22 2005-04-07 Unilever Plc Traitements pour la peau
WO2009062682A1 (fr) * 2007-11-13 2009-05-22 Erlacos Gmbh Stéroïdes c-19 à usage cosmétique et autres
US8445005B2 (en) 2004-08-30 2013-05-21 Kao Corporation Antiwrinkle agent, lipolysis promoter, external composition for skin and food and beverage composition
US9125816B2 (en) 2000-08-30 2015-09-08 Besins Healthcare Inc. Pharmaceutical composition and method for treating hypogonadism
US10265328B2 (en) 2007-11-13 2019-04-23 Procima Gmbh C-19 steroids for specific therapeutic uses

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0632722A (ja) * 1992-07-13 1994-02-08 Shiseido Co Ltd 皮膚外用剤
JP6833456B2 (ja) * 2016-11-02 2021-02-24 日東電工株式会社 皮膚線維症処置剤
JPWO2019022250A1 (ja) * 2017-07-28 2020-07-09 国立大学法人九州大学 水溶性有効成分の放出が制御された経皮吸収組成物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1538227A (en) * 1975-03-21 1979-01-10 Beecham Group Ltd 16,16-disubstituted steroids of the androstene series
EP0339905A2 (fr) * 1988-04-25 1989-11-02 Ethicon, Inc. Composition cicatrisante contenant un facteur de croissance et des rétinoides
EP0391033A2 (fr) * 1989-04-07 1990-10-10 Ruey J. Dr. Yu Rétinal, ses dérivés et leur utilisation thérapeutique

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1538227A (en) * 1975-03-21 1979-01-10 Beecham Group Ltd 16,16-disubstituted steroids of the androstene series
EP0339905A2 (fr) * 1988-04-25 1989-11-02 Ethicon, Inc. Composition cicatrisante contenant un facteur de croissance et des rétinoides
EP0391033A2 (fr) * 1989-04-07 1990-10-10 Ruey J. Dr. Yu Rétinal, ses dérivés et leur utilisation thérapeutique

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5527807A (en) * 1992-05-20 1996-06-18 Merck & Co., Inc. 7β-substituted-4-aza-5α-cholestan-3-ones as 5α reductase inhibitors useful in the prevention and treatment of hyperandrogenetic disorders
WO1995013077A1 (fr) * 1993-11-12 1995-05-18 Merck & Co., Inc. 7β-SUBSTITUES-4-AZA-5α-CHOLESTAN-3-ONES UTILISES COMME INHIBITEURS SELECTIFS DE LA 5α-REDUCTASE 1
FR2718021A1 (fr) * 1994-04-05 1995-10-06 Fabre Pierre Cosmetique Composition topique à base de rétinal.
WO1995026709A1 (fr) * 1994-04-05 1995-10-12 Pierre Fabre Dermo-Cosmetique Composition topique a base de retinal
EP0786999A1 (fr) * 1994-10-21 1997-08-06 Merck & Co., Inc. Procede combine de traitement de l'acne
EP0792371A1 (fr) * 1994-10-21 1997-09-03 Merck & Co., Inc. Procede combine de traitement de l'acne
EP0792371A4 (fr) * 1994-10-21 1998-12-30 Merck & Co Inc Procede combine de traitement de l'acne
EP0786999A4 (fr) * 1994-10-21 1999-01-20 Merck & Co Inc Procede combine de traitement de l'acne
US9125816B2 (en) 2000-08-30 2015-09-08 Besins Healthcare Inc. Pharmaceutical composition and method for treating hypogonadism
US9132089B2 (en) 2000-08-30 2015-09-15 Besins Healthcare Inc. Pharmaceutical composition and method for treating hypogonadism
WO2004103320A3 (fr) * 2003-05-22 2005-04-07 Unilever Plc Traitements pour la peau
US8318710B2 (en) 2003-05-22 2012-11-27 Conopco, Inc. Skin treatments
US8445005B2 (en) 2004-08-30 2013-05-21 Kao Corporation Antiwrinkle agent, lipolysis promoter, external composition for skin and food and beverage composition
CN101854908B (zh) * 2007-11-13 2013-03-06 埃拉克斯有限责任公司 用于化妆品和其他应用的c-19甾族化合物
US8258123B2 (en) 2007-11-13 2012-09-04 Erlacos Gmbh C-19 steroids for cosmetic and further uses
WO2009062682A1 (fr) * 2007-11-13 2009-05-22 Erlacos Gmbh Stéroïdes c-19 à usage cosmétique et autres
US10265328B2 (en) 2007-11-13 2019-04-23 Procima Gmbh C-19 steroids for specific therapeutic uses

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EP0555309A1 (fr) 1993-08-18

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