WO1992005763A1 - Composition containing steroid derivatives - Google Patents
Composition containing steroid derivatives Download PDFInfo
- Publication number
- WO1992005763A1 WO1992005763A1 PCT/GB1991/001677 GB9101677W WO9205763A1 WO 1992005763 A1 WO1992005763 A1 WO 1992005763A1 GB 9101677 W GB9101677 W GB 9101677W WO 9205763 A1 WO9205763 A1 WO 9205763A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- compound
- volatile
- formula
- group
- Prior art date
Links
Classifications
-
- 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
- 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
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- 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
- 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
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
-
- 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
- This invention relates to a novel composition
- a novel composition comprising a 16,16-disubstituted androstene steroid compound, specifically adapted for topical application.
- United Kingdom Patent, GB 1 538 227 discloses a group of 16,16-disubstituted androstene steroid compounds having pharmaceutical activity, which particular compounds are described as having utility in the treatment of androgen dependent skin disorders such as acne and seborrhoea.
- the possible use of these compounds in the treatment of androgenic alopecia and male pattern baldness in women is proposed, but not substantiated.
- GB 1 538 227 describes compounds of formula (I) :
- R-L is a alkyl group, a C ⁇ _g alkenyl group, a sZ-s-. ⁇ , 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 OR 4 wherein R4 is a C 2 _7 alkanoyl group, a C 1 _ 4 alkyl group, or an optionally substituted benzyl group; and R3 is hydrogen or a C ⁇ __ 5 alkyl group; or R 2 and R3 together with the carbon atom to which they are joined represent a carbonyl group.
- Optional substituents for phenyl moieties include C 1 _ 4 alkyl, halogen and nitro.
- R- ⁇ 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.
- R3 is hydrogen or methyl, and most preferably hydrogen.
- R-_ is methyl; R 2 is hydroxy and has the ⁇ -configuration; and R3 is hydrogen, which is the compound androst-4-ene-16,16-dimethyl-17 ⁇ -ol-3-one.
- GB 1 538 227 discloses a pharmaceutical composition
- a pharmaceutical composition comprising a compound of formula (I) together with a pharmaceutically acceptable carrier, for topical or oral administration.
- GB 1 538 227 describes a preferred composition for topical administration to the skin as comprising a compound of formula (I) which has been formulated as a cream or ointment using conventional formulations well known in the art, for example as described in standard text books of pharmaceutics and cosmetics, such as Harry's Cosmeticology and the British Pharmacopoeia.
- Anhydrous polyethylene glycol is the only material identified as a suitable carrier for use in topical formulations; no specific formulation is provided by way of example.
- Compounds of formula (I) and in particular the compound androst-4-ene-16, 16-dimethyl-17 ⁇ -ol-3-one are claimed to have 5 ⁇ -reductase inhibitory activity but no significant androgenic, anti-androgenic or anabolic activity.
- the lack of systemic side-effects is considered to render these compounds, and especially the compound androst-4-ene-16,16-dimethyl-17 ⁇ -ol-3-one, particularly suitable for targeted delivery in a topically administered composition.
- a steroid compound described in GB 1 538 227 in particular the compound androst-4-ene-16,16-dimethyl-17 ⁇ -ol-3-one, is surprisingly effective as an antagonist of the influences of hormones in relation to hair growth and skin disorders.
- compositions according to the present invention are therefore considered to have utility in arresting hair-loss, in promoting hair-growth, in the treatment of acne, and in reducing excessive secretion of sebum from the sebaceous glands in particular as a cosmetic treatment for greasy skin and hair.
- a topically administrable composition comprising a compound of formula (I) as hereinbefore defined and a topically acceptable carrier which includes a volatile solvent, wherein the composition is specifically adapted to present a compound of formula (I) to a site of action on the skin or scale in a substantially saturated or super-saturated concentration such that penetration of the skin or scalp is promoted.
- a particularly preferred compound of formula (I) for use in compositions of the present invention is the compound androst-4-ene-16,16-dimethyl-17 ⁇ -ol-3-one.
- the topically acceptable carrier comprises a volatile solvent selected from a volatile alcohol such as ethanol or propan-2-ol, a volatile oil such as a volatile silicone fluid, and mixtures thereof.
- the topically acceptable carrier may further comprise a less-volatile or non-volatile co-solvent. It is not necessary for the compound of formula (I) to be readily soluble in the co-solvent but it will be appreciated that the ratio of volatile solvent to co-solvent will generally be selected to solubilise the compound of formula (I) .
- a less-volatile co-solvent include benzyl alcohol and water.
- non-volatile co-solvents include propylene glycol, polyethylene glycol, non-volatile silicone fluids and Arlasolve DMI (dimethyl iso-sorbide) .
- compositions for use in the present invention may be single-phase systems in which a compound of formula (I) is dissolved in a topically acceptable carrier, or, alternatively, multi-phase systems, preferably dual-phase systems, in which a compound of formula (I) is dissolved in at least one of the phases comprising the 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 single phase solution substantially saturated and preferably super-saturated in the compound of formula (I) may be created in situ from a solution which is sub-saturated in the compound of formula (I) by using a mixture of volatile and less-volatile or non-volatile solvents.
- the volatile solvent rapidly evaporates thereby increasing the concentration of the compound of formula (I) to substantially saturated and preferably super-saturated level.
- volatile solvents include ethanol, propan-2-ol.
- Suitable examples of non-volatile solvents include propylene glycol, polyethylene glycol, non-volatile silicone fluids and Arlasolve DMI (dimethyl iso-sorbide) .
- Suitable examples of less-volatile solvents include benzyl alcohol and water.
- formulations of the invention enhance the penetration of the compound of formula I through the skin.
- the formulation results in between 5x to 12x, more preferably 10x, supersaturation of the compound of formula I when the volatile phase has evaporated.
- substantially saturated and preferably super-saturated 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 concentration of the compound of formula (I) are selected such that on admixture of the two phases the concentration of the compound of formula (I) is near to or greater than its saturated solubility in the initially formed resultant mixture.
- compositions in accordance with the present invention which are substantially saturated and preferably super-saturated will additionally contain an anti-nucleating ag * __nt in order to prevent precipitation of the compound of formula (I) from solution.
- Suitable anti-nucleating agents include polyvinylpyrrolidone (PVP) , carboxymethyl cellulose (CMC) , and hydroxypropyl methyl cellulose (HPMC) .
- a typical composition of the invention will comprise (w/v) from 0.005 to 5%, preferably 0.5 to 1.5% and more preferably 2% of a compound of formula (I) .
- compositions will optionally include (w/v) upto 12%, preferably 1.0 to 7.5% of an anti-nucleating agent.
- antinucleating agent is present in a ratio of 2:1 to 5:1, antinucleating agent: compound of formula I.
- a typical single-phase formulation will include a topically acceptable carrier comprising (w/v) from 80 to 99% of a volatile solvent or volatile solvent mixture, optionally with from 1 to 20% of a less-volatile or non-volatile solvent or mixtures thereof.
- the compound of formula (I) will generally be dissolved in or form an emulsion with a first phase comprising a volatile solvent, or a mixture of a volatile solvent and a less-volatile solvent, which first phase optionally contains an anti-nucleating agent, whilst the second phase will generally comprise a mixture of less-volatile and non-volatile solvents, including water, which second phase optionally contains an anti-nucleating agent.
- the terms 'liquid' and 'solution' include viscous materials such as creams, ointments and gels.
- compositions according to 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 appropriate, conditioners, tonics, lotions, creams, dressings, gels, spray on conditioners, aerosol conditioning sprays, mousses, post foaming hair gels, styling and hairsprays.
- compositions may additionally contain a particulate substance such as silica, silanised silica or talc, which substance may improve the feel and appearance of a treated skin area.
- a particulate substance such as silica, silanised silica or talc, which substance may improve the feel and appearance of a treated skin area.
- compositions according to the present invention may contain, in addition to a compound of formula (I) , further topically active substances.
- a composition for anti-acne use may contain a topically administrable anti-microbial agent and a composition for application to the scalp may contain an anti-dandruff agent.
- 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.
- Multi-phase compositions according to the invention may be packaged into a multiple-compartment pack ready for topical application by the user who will normally apply the phases simultaneously to the treatment area and mix the phases together in situ.
- multiple phases may be contained in a single-compartment pack separated by an internal membrane or membranes. In-pack mixing may then take place on breaking the membrane or membranes immediately prior to application. Suitable packs for these purposes are commercially available.
- the present invention provides a method of treating skin-disorders, in particular acne, and reducing excessive production of sebum from sebaceous glands onto the face, scalp and hair, which method comprises the topical administration to the skin or scalp of an effective amount of a topically administrable composition in accordance with the invention.
- the present invention provides a method for arresting hair-loss and/or promoting hair-growth which method comprises the topical administration to the scalp of an effective amount of a topically administrable composition in accordance with the invention.
- the quantity of each constituent present in the specific formulations is expressed as a percentage (w/w) of the total composition for single phase systems, and as a percentage (w/w) of the phase in which it is present for multiphase systems.
- the anti nucleating agent can be either. Polyvinyl pyrrolidone or Polyvinyl pyrrolidone vinyl acetate copolymer.
- Formulations E2(a)-(c) are mixed in situ or immediately 0 prior to application to form a miscible solution.
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3517410A JPH06502160A (en) | 1990-10-04 | 1991-09-30 | Steroid derivative-containing composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9021546.8 | 1990-10-04 | ||
GB909021546A GB9021546D0 (en) | 1990-10-04 | 1990-10-04 | Novel composition |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1992005763A1 true WO1992005763A1 (en) | 1992-04-16 |
Family
ID=10683202
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1991/001677 WO1992005763A1 (en) | 1990-10-04 | 1991-09-30 | Composition containing steroid derivatives |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP0551321A1 (en) |
JP (1) | JPH06502160A (en) |
AU (1) | AU8649191A (en) |
CA (1) | CA2093349A1 (en) |
GB (1) | GB9021546D0 (en) |
IE (1) | IE913469A1 (en) |
WO (1) | WO1992005763A1 (en) |
ZA (1) | ZA917879B (en) |
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993017687A1 (en) * | 1992-03-10 | 1993-09-16 | Smithkline Beecham Plc | Topical compositions containing steroids |
US20080206161A1 (en) * | 2002-10-25 | 2008-08-28 | Dov Tamarkin | Quiescent foamable compositions, steroids, kits and uses thereof |
WO2009062682A1 (en) * | 2007-11-13 | 2009-05-22 | Erlacos Gmbh | C-19 steroids for cosmetic and further uses |
US8840869B2 (en) | 2002-10-25 | 2014-09-23 | Foamix Ltd. | Body cavity foams |
US8865139B1 (en) | 2009-10-02 | 2014-10-21 | Foamix Pharmaceuticals Ltd. | Topical tetracycline compositions |
US8900554B2 (en) | 2002-10-25 | 2014-12-02 | Foamix Pharmaceuticals Ltd. | Foamable composition and uses thereof |
US8900553B2 (en) | 2007-12-07 | 2014-12-02 | Foamix Pharmaceuticals Ltd. | Oil and liquid silicone foamable carriers and formulations |
US9050253B2 (en) | 2003-08-04 | 2015-06-09 | Foamix Pharmaceuticals Ltd. | Oleaginous pharmaceutical and cosmetic foam |
US9072667B2 (en) | 2009-07-29 | 2015-07-07 | Foamix Pharmaceuticals Ltd. | Non surface active agent non polymeric agent hydro-alcoholic foamable compositions, breakable foams and their uses |
US9101662B2 (en) | 2003-08-04 | 2015-08-11 | Foamix Pharmaceuticals Ltd. | Compositions with modulating agents |
US9167813B2 (en) | 2009-07-29 | 2015-10-27 | Foamix Pharmaceuticals Ltd. | Non surfactant hydro-alcoholic foamable compositions, breakable foams and their uses |
US9211259B2 (en) | 2002-11-29 | 2015-12-15 | Foamix Pharmaceuticals Ltd. | Antibiotic kit and composition and uses thereof |
US9265725B2 (en) | 2002-10-25 | 2016-02-23 | Foamix Pharmaceuticals Ltd. | Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof |
US9320705B2 (en) | 2002-10-25 | 2016-04-26 | Foamix Pharmaceuticals Ltd. | Sensation modifying topical composition foam |
US9439857B2 (en) | 2007-11-30 | 2016-09-13 | Foamix Pharmaceuticals Ltd. | Foam containing benzoyl peroxide |
US9492412B2 (en) | 2002-10-25 | 2016-11-15 | Foamix Pharmaceuticals Ltd. | Penetrating pharmaceutical foam |
US9539208B2 (en) | 2002-10-25 | 2017-01-10 | Foamix Pharmaceuticals Ltd. | Foam prepared from nanoemulsions and uses |
US9622947B2 (en) | 2002-10-25 | 2017-04-18 | Foamix Pharmaceuticals Ltd. | Foamable composition combining a polar solvent and a hydrophobic carrier |
US9636405B2 (en) | 2003-08-04 | 2017-05-02 | Foamix Pharmaceuticals Ltd. | Foamable vehicle and pharmaceutical compositions thereof |
US9662298B2 (en) | 2007-08-07 | 2017-05-30 | Foamix Pharmaceuticals Ltd. | Wax foamable vehicle and pharmaceutical compositions thereof |
US9668972B2 (en) | 2002-10-25 | 2017-06-06 | Foamix Pharmaceuticals Ltd. | Nonsteroidal immunomodulating kit and composition and uses thereof |
US9682021B2 (en) | 2006-11-14 | 2017-06-20 | Foamix Pharmaceuticals Ltd. | Substantially non-aqueous foamable petrolatum based pharmaceutical and cosmetic compositions and their uses |
US9849142B2 (en) | 2009-10-02 | 2017-12-26 | Foamix Pharmaceuticals Ltd. | Methods for accelerated return of skin integrity and for the treatment of impetigo |
US9884017B2 (en) | 2009-04-28 | 2018-02-06 | Foamix Pharmaceuticals Ltd. | Foamable vehicles and pharmaceutical compositions comprising aprotic polar solvents and uses thereof |
US10265328B2 (en) | 2007-11-13 | 2019-04-23 | Procima Gmbh | C-19 steroids for specific therapeutic uses |
US10398641B2 (en) | 2016-09-08 | 2019-09-03 | Foamix Pharmaceuticals Ltd. | Compositions and methods for treating rosacea and acne |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0518769D0 (en) * | 2005-09-14 | 2005-10-19 | Medpharm Ltd | Topical formulations |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2231383A1 (en) * | 1973-05-29 | 1974-12-27 | Searle & Co | |
GB1538227A (en) * | 1975-03-21 | 1979-01-10 | Beecham Group Ltd | 16,16-disubstituted steroids of the androstene series |
EP0071153A1 (en) * | 1981-07-29 | 1983-02-09 | Schering Aktiengesellschaft | Androstane derivatives, process for their preparation and pharmaceutical compositions containing them |
US4767751A (en) * | 1984-01-25 | 1988-08-30 | Beecham Group P.L.C. | Topical drug release system |
-
1990
- 1990-10-04 GB GB909021546A patent/GB9021546D0/en active Pending
-
1991
- 1991-09-30 AU AU86491/91A patent/AU8649191A/en not_active Abandoned
- 1991-09-30 EP EP91917032A patent/EP0551321A1/en not_active Ceased
- 1991-09-30 WO PCT/GB1991/001677 patent/WO1992005763A1/en not_active Application Discontinuation
- 1991-09-30 JP JP3517410A patent/JPH06502160A/en active Pending
- 1991-09-30 CA CA002093349A patent/CA2093349A1/en not_active Abandoned
- 1991-10-02 ZA ZA917879A patent/ZA917879B/en unknown
- 1991-10-02 IE IE346991A patent/IE913469A1/en not_active Application Discontinuation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2231383A1 (en) * | 1973-05-29 | 1974-12-27 | Searle & Co | |
GB1538227A (en) * | 1975-03-21 | 1979-01-10 | Beecham Group Ltd | 16,16-disubstituted steroids of the androstene series |
EP0071153A1 (en) * | 1981-07-29 | 1983-02-09 | Schering Aktiengesellschaft | Androstane derivatives, process for their preparation and pharmaceutical compositions containing them |
US4767751A (en) * | 1984-01-25 | 1988-08-30 | Beecham Group P.L.C. | Topical drug release system |
Non-Patent Citations (1)
Title |
---|
STN INTERNATIONAL INFORMATION SERVICES DATA BASE: CHEMICAL ABSTRACTS, vol. 107, no. 22, abstract no. 204918t, Columbus, Ohio, US; & JP-A-62 132 810 (SHISEIDO CO., LTD) 16-06-1987, see the abstract * |
Cited By (65)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993017687A1 (en) * | 1992-03-10 | 1993-09-16 | Smithkline Beecham Plc | Topical compositions containing steroids |
US9622947B2 (en) | 2002-10-25 | 2017-04-18 | Foamix Pharmaceuticals Ltd. | Foamable composition combining a polar solvent and a hydrophobic carrier |
US9539208B2 (en) | 2002-10-25 | 2017-01-10 | Foamix Pharmaceuticals Ltd. | Foam prepared from nanoemulsions and uses |
US10117812B2 (en) | 2002-10-25 | 2018-11-06 | Foamix Pharmaceuticals Ltd. | Foamable composition combining a polar solvent and a hydrophobic carrier |
US8840869B2 (en) | 2002-10-25 | 2014-09-23 | Foamix Ltd. | Body cavity foams |
US9668972B2 (en) | 2002-10-25 | 2017-06-06 | Foamix Pharmaceuticals Ltd. | Nonsteroidal immunomodulating kit and composition and uses thereof |
US10322085B2 (en) | 2002-10-25 | 2019-06-18 | Foamix Pharmaceuticals Ltd. | Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof |
US8900554B2 (en) | 2002-10-25 | 2014-12-02 | Foamix Pharmaceuticals Ltd. | Foamable composition and uses thereof |
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US11033491B2 (en) | 2002-10-25 | 2021-06-15 | Vyne Therapeutics Inc. | Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof |
US10821077B2 (en) | 2002-10-25 | 2020-11-03 | Foamix Pharmaceuticals Ltd. | Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof |
US9492412B2 (en) | 2002-10-25 | 2016-11-15 | Foamix Pharmaceuticals Ltd. | Penetrating pharmaceutical foam |
US9320705B2 (en) | 2002-10-25 | 2016-04-26 | Foamix Pharmaceuticals Ltd. | Sensation modifying topical composition foam |
US9265725B2 (en) | 2002-10-25 | 2016-02-23 | Foamix Pharmaceuticals Ltd. | Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof |
US20080206161A1 (en) * | 2002-10-25 | 2008-08-28 | Dov Tamarkin | Quiescent foamable compositions, steroids, kits and uses thereof |
US9211259B2 (en) | 2002-11-29 | 2015-12-15 | Foamix Pharmaceuticals Ltd. | Antibiotic kit and composition and uses thereof |
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US10369102B2 (en) | 2007-08-07 | 2019-08-06 | Foamix Pharmaceuticals Ltd. | Wax foamable vehicle and pharmaceutical compositions thereof |
US10265328B2 (en) | 2007-11-13 | 2019-04-23 | Procima Gmbh | C-19 steroids for specific therapeutic uses |
US8258123B2 (en) | 2007-11-13 | 2012-09-04 | Erlacos Gmbh | C-19 steroids for cosmetic and further uses |
WO2009062682A1 (en) * | 2007-11-13 | 2009-05-22 | Erlacos Gmbh | C-19 steroids for cosmetic and further uses |
US9439857B2 (en) | 2007-11-30 | 2016-09-13 | Foamix Pharmaceuticals Ltd. | Foam containing benzoyl peroxide |
US8900553B2 (en) | 2007-12-07 | 2014-12-02 | Foamix Pharmaceuticals Ltd. | Oil and liquid silicone foamable carriers and formulations |
US9549898B2 (en) | 2007-12-07 | 2017-01-24 | Foamix Pharmaceuticals Ltd. | Oil and liquid silicone foamable carriers and formulations |
US9161916B2 (en) | 2007-12-07 | 2015-10-20 | Foamix Pharmaceuticals Ltd. | Carriers, formulations, methods for formulating unstable active agents for external application and uses thereof |
US11433025B2 (en) | 2007-12-07 | 2022-09-06 | Vyne Therapeutics Inc. | Oil foamable carriers and formulations |
US9795564B2 (en) | 2007-12-07 | 2017-10-24 | Foamix Pharmaceuticals Ltd. | Oil-based foamable carriers and formulations |
US9884017B2 (en) | 2009-04-28 | 2018-02-06 | Foamix Pharmaceuticals Ltd. | Foamable vehicles and pharmaceutical compositions comprising aprotic polar solvents and uses thereof |
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US9572775B2 (en) | 2009-07-29 | 2017-02-21 | Foamix Pharmaceuticals Ltd. | Non surfactant hydro-alcoholic foamable compositions, breakable foams and their uses |
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Also Published As
Publication number | Publication date |
---|---|
ZA917879B (en) | 1992-12-30 |
CA2093349A1 (en) | 1992-04-05 |
IE913469A1 (en) | 1992-04-08 |
EP0551321A1 (en) | 1993-07-21 |
JPH06502160A (en) | 1994-03-10 |
GB9021546D0 (en) | 1990-11-21 |
AU8649191A (en) | 1992-04-28 |
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