EP1901709A2 - Controlled release of a drug through skin on the basis of a topical composition comprising a drug, a film-forming silicone and at least one volatile solvent - Google Patents
Controlled release of a drug through skin on the basis of a topical composition comprising a drug, a film-forming silicone and at least one volatile solventInfo
- Publication number
- EP1901709A2 EP1901709A2 EP06754427A EP06754427A EP1901709A2 EP 1901709 A2 EP1901709 A2 EP 1901709A2 EP 06754427 A EP06754427 A EP 06754427A EP 06754427 A EP06754427 A EP 06754427A EP 1901709 A2 EP1901709 A2 EP 1901709A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- drug
- composition
- vitamin
- silicone
- skin
- 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- Withdrawn
Links
Classifications
-
- 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
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- 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
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
-
- 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
- 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
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
Definitions
- the present invention pertains to the field of drug formulation for topical administration.
- skin penetration can be enhanced by the following strategies: (i) increasing drug diffusivity in the skin; (ii) increasing drug solubility in the skin, and/or (iii) increasing the degree of saturation of the drug in the formulation.
- supersaturated formulations in which the degree of saturation of the drug is increased compared to conventional formulations, are often unstable, mainly because of crystallisation of the drug.
- the invention provides a method for the controlled release of a drug through skin, which method comprises topically administering a composition that comprises at least one solubilized drug, a film-forming silicone, and at least one volatile solvent.
- the invention provides a method wherein the drug penetrates the upper layers of the skin that serves as a reservoir wherein the drug concentrates before being released to dermis.
- the drug may be vitamin D or a vitamin D analogue, such as calcitriol, or a corticosteroid, such as clobetasol or clobetasol-17-propionate, alone or in combination.
- the figure shows the results of a blanching test, presented as mean values of visual core across time after topical application of Dermoval®, Daivobet®, Diprolene® creams, or a silicone ointment, as described in Example 2.
- topical compositions that comprise at least one solubilized drug, a film-forming silicone, and at least one volatile solvent allow for the controlled release of the drug through skin, while showing a good stability.
- the release of the drug is slow and sustained, which makes it possible to lower the dosage.
- the drug can thus be administered at a dosage that is lower than the dosage used for compositions comprising the same drug, but free of the film-forming silicone and the volatile solvent.
- the drug penetrates into the skin according to a specific zero-order kinetic, which means that the drug concentration exhibits a linear variation vs time, and that the penetration is constant and sustained.
- the drug is first maintained within the upper layers of the skin, that is to say the layers consisting of :
- the release of the drug into the lower layers is controlled by the in situ supersaturation of the drug.
- Supersaturation is achieved when the solvent evaporates after the composition is applied onto skin. This evaporation concentrates the drug in solution, which favors its penetration in the upper layers of the skin and creates a reservoir effect.
- the silicone allows the control of the evaporation kinetic of the solvent and the control of the crystallisation of the drug, which also favors its penetration.
- composition described herein comprises at least one drug, i.e. a pharmaceutically active ingredient.
- a pharmaceutically active ingredient i.e. a pharmaceutically active ingredient.
- it may comprise two drugs.
- drugs of interest are vitamin D or a vitamin D analogue.
- vitamin D means the various forms of vitamin D such as vitamin Di, D 2 , D 3 or vitamin D 4 .
- vitamin D analogue means the compounds that exhibit analogous biological properties compared to vitamin D, in particular with regard to the transactivation of the response elements of vitamin D (VDRE) 1 such as an agonist or antagonist activity towards the vitamin D receptors.
- VDRE vitamin D
- These compounds preferably are synthetic compounds that comprise the squeleton of vitamin D with modifications of lateral chains and/or that also comprise modifications within this squeleton.
- the analogues may comprise structural analogues, in particular biaromatic compounds.
- the vitamin D analogue is selected from the group consisting of calcitriol, calcipotriol, doxercalciferol, secalcitol, maxacalcitol, seocalcitol, tacalcitol, paricalcitol, falecalcitriole, 1 ⁇ ,24S-dihydroxy-vitamine D2, 1 (S), 3(R)- dihydroxy-20(R)-[((3-(2-hydroxy-2-propyl)-phenyl)-methoxy)-methyl]-9,10-seco- pregna-(Z),7(E),10(19)-triene and mixture thereof. Most preferably, it is calcitriol.
- vitamin D analogues include those described in documents WO 02/34235, WO 00/64450, EP1124779, EP1235824, EP1235777, WO 02/94754, WO 03/050067 et WO 00/26167.
- the compounds described in WO 00/26167 relate to structural analogues of vitamin D that show a selective activity on cell proliferation and differentiation without showing hypercalcemic activity.
- the quantity of vitamin D or vitamin D analogue solubilized in the composition is from 0.00001 to 5 % w/w, preferably from 0.0001 to 3 % w/w and more preferably from 0.0003 to 1 % w/w.
- Another drug of interest is a corticosteroid.
- corticosteroid means a topical steroid of group I, II, III or IV (strong or weak).
- betamethasone clobetasol, clobetasone, desoximethasone, diflucortolon, diflorasone, fluoci ⁇ onide, flumethasone, fluocinolon, fluticasone, fluprednidene, halcinonide, hydrocortisone, momethasone, triamcinolon, pharmaceutically acceptable esters or acetonides thereof, and mixtures thereof.
- esters or acetonides examples include 17-valerate, 17-propionate, 17,21-dipropionate, acetonide, acetonide-21-N-benzoyl-2-methyl- ⁇ -alaninate, acetonide-21-(3,3-dimethylbutyrate) and 17-butyrate.
- the corticosteroid is clobetasol or clobetasol-17- propionate.
- the quantity of corticosteroid in a solubilized form in the composition is from 0.0001 to 1 % w/w, more preferably from 0.0005 to 3 % w/w, and more preferably from 0.001 to 0.1 % w/w.
- the active ingredients are solubilized in the same solvent or in several solvents.
- the solvent is selected among pharmaceutically acceptable compounds, i.e. compounds that are suitable for a topical application.
- Preferred volatile solvents include alkanols, alkylglycols, alkylketones and/or alkyl esters wherein the alkyl moieties contain from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, such as ethanol, isopropanol, n-butanol, ethyl acetate, acetone, and mixtures thereof.
- the volatile solvent is ethanol, especially when the drugs are calcitriol and clobetasol- 17-propionate.
- the quantity of solvent within a composition is from 1 to 50 % w/w (based on the total weight of the composition), preferably from 2 to 40 % w/w and more preferably from 5 to 20 % w/w.
- the film-forming silicone used in the invention preferably comprises at least one polyorganosiloxane elastomer.
- polyorganosiloxane elastomer hereby refers to any siloxane polymer, which is chemically cross-linked and which exhibits viscoelastic properties.
- polyorganosiloxane elastomers examples include those described in patents US 4,980,167 and US 4,742,142.
- the used polyorganosiloxanes may especially be addition products (adducts) resulting from hydrosylation, and/or polymeric products deriving from the addition of (i) a polyorganosiloxane having unsaturated groups, such as vinyl or allyl groups, for example linked to at least an atome, and (ii) another silicone product able to be involved in the addition reaction, such as an organohydrogenopolysiloxane.
- the polyorganosiloxane elastomer is present in a least one volatile silicone oil that is a linear or cyclic polyorganosiloxane oil having 2 to 10 silicium atoms.
- volatile silicone oil that is a linear or cyclic polyorganosiloxane oil having 2 to 10 silicium atoms.
- polyorganosiloxane oils hereby refers to any silicone oil able to evaporate in contact of skin, mucosa or keratinic fibers preferably with an evaporation duration of less than 1 hour, at ambient temperature and water atmospheric pressure.
- Polyorganosiloxane oils useful in the invention are, for example, linear or cyclic polyorganosiloxanes having 2 to 10 silicium atoms, optionally comprising alkyl or alkoxy groups having 1 to 22 carbon atoms. Silicone oils used in the invention advantageously exhibit a viscosity of at most 6.10 6 m 2 /s (6 centistokes).
- Suitable volatile silicone oils especially include cyclomethicones and/or dimethicones of low molecular weight.
- cyclic polyorganosiloxanes especially cyclic methoxylated organospolysiloxane, with a 4-membered to 12- membered siloxane ring such as octamethylcyclotetrasiloxane and decamethylcyclopentasiloxane, may be used.
- Suitable volatile silocne oils are dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and mixtures thereof.
- a particularly suitable film-forming silicone according to the invention comprises a polyorganosiloxane elastomer in decamethyltetrasiloxane.
- a preferred silicone product is the so-called "ST Elastomer 10 ® " of DOW CORNING, which is formulated in the form of a viscous and translucid gel.
- the film-forming silicone used in the method of the invention is a silicone product obtained by a cross-linking of :
- polysiloxane (A) advantageously comprises one or more compounds having one of the following formulae (A 1 ), (A 2"1 ) and (A 2'2 ) :
- R 14 , R 15 et R 16 are similar or different, and each represents an alkyl group with 1 to 6 carbon atoms ; - a is an integer having a value of 0 to 250,
- - b is an integer having a value of 1 to 250 ;
- - c is an integer having a value of 0 to 250.
- polysiloxane (A) contains compounds of above formulae (A 2'1 ) and/or (A 2"2 ), preferably together with compounds of formula (A 1 ), , with a molar ratio (A 2"1 + A 2'2 ) : (A 1 ) preferably between 0 to
- suitable alpha, omega - diene are especially 1 ,4-pentadiene, 1 ,5-hexadiene, 1 ,6-heptadiene, 1 ,7-octadiene, 1 ,8- nonadiene, 1 ,9-decadiene, 1 ,11-dodecadiene, 1 ,13-tetradecadiene, et 1 ,19- eicosadiene.
- Polysiloxane (C) may especially include, alone or in combination : (C1) linear, branched, or cyclic volatile methylsiloxanes, for example : - volatile methoxysiloxanes selected from hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, tetradecamethylhexasiloxane, and/or hexadecamethylheptasiloxane ; - cyclic volatiles methylsiloxanes such as hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and/or dodecamethylcyclohexasiloxane.
- (C1) linear, branched, or cyclic volatile methylsiloxanes for example : - volatile methoxysi
- - branched volatile methylsiloxanes such as heptamethyl-3- [(trimethylsilyl)oxy]-trisiloxane, hexamethyl-3,3,bis[(trimethylsilyl)oxy]- trisiloxane, and/or pentamethyl[(trimethylsilyl)oxy]-cyclotrisiloxane ;
- (C2) alkyl- and/or aryl- siloxanes which are linear, or cyclic, and which are volatile or non-volatile, especially low molecular weight, non-volatile, compounds having a viscosity of about 100 to 1000 mm 2 /s (centistokes), especially those depicted by the following formula :
- - e has a value preferably of 80 to 375
- R 17 et R 18 are alkyl radical having 1 to 20 carbon atoms, or an aryl group such as a phenyle, for example polydimethylsiloxanes, polydiethylsiloxanes, polymethyl- ethylsiloxanes, polymethylphenylsiloxanes and/or polydiphenylsiloxanes ;
- (C3) functionalized siloxanes which are linear, or cyclic, especially fluid siloxanes, for example functionalized with groups selected from acrylamides, acrylates, amides, amino, carbinol, carboxy, chloroalkyles, epoxy, glycol, cetal, mercapto, methylester, perfluoro and silanol.
- Polysiloxane (C) is a low molecular weight silicone oil selected from volatile methylsiloxanes, of low molecular weight, which are linear or cyclic.
- polysiloxanes suitable for an use as film-forming silicones according to the invention are silicone polymers with an average molecular weight of at least 10 000 (e.g. from 10 000 to 10 000 000).
- examples of such polysiloxanes include copolymers of crosslinked siloxanes, especially copolymers of dimethicone or dimethicone derivatives, for example siloxane stearyl methyl-dimethyl copolymers (such as « Gransil SR-CYC ® » of Grant Industries), copolymers of the type of the « Polysilicone-11 ® » (crosslinked elastomer silicone formed by reaction of a vinyl-terminated silicone with methylhydrodimethylsiloxane in the presence de cyclomethicone), crosslinked cetearyl dimethicone/vinyl dimethicone copolymers (namely copolymers of cetearyl dimethicone crosslinked with a vinyl dimethyl polysiloxane), crosslinked dimethi
- Silicones formulated as a gel may be obtained especially from the
- the composition used in the method of the invention is advantageously free from polyorganosiloxane having alkyl groups.
- the film-forming silicone of the method of the invention is advantageously present in the composition at a concentration of 20 to 90% weight based on the total weight of the composition, preferably of between 30 and 80%.
- the compositions described herein may further contain an oily additive, such as isopropyl palmitate, dicaprilic ether, dimethicone, or mixtures thereof.
- compositions described herein may also contain flavour-enhancing agents, preservatives such as para-hydroxybenzoic acid esters, stabilizing agents, moisture regulators, pH regulators, osmotic pressure modifiers, emulsifying agents, UV-A and UV-B screening agents, and antioxidants such as cc-tocopherol, butylhydroxyanisole or butylhydroxytoluene, superoxide dismutase, ubiquinol, or certain chelating agents.
- preservatives such as para-hydroxybenzoic acid esters
- stabilizing agents such as para-hydroxybenzoic acid esters, stabilizing agents, moisture regulators, pH regulators, osmotic pressure modifiers, emulsifying agents, UV-A and UV-B screening agents
- antioxidants such as cc-tocopherol, butylhydroxyanisole or butylhydroxytoluene, superoxide dismutase, ubiquinol, or certain chelating agents.
- the composition is in form of a cream, a gel, an ointment or a pomade.
- the composition is substantially free of water, i.e. it contains less than 5 % w/w of water, preferably less than 3 %, most preferably 0 % of water.
- compositions comprise : - isopropyl palmitate
- composition comprises :
- Example 1 Preparation of a control led-release formulation
- the process described below is a general manufacture process of a silicone ointment that comprises a vitamin D analogue and a corticosteroid.
- First step preparation of the phase that comprises the silicone
- phase II preparation of the phase that comprises the active ingredients (phase II) : A parent solution is prepared, that comprises a vitamin D analogue in an appropriate solvent, and an anti-oxidant. The solution is stirred until solubilization of the active ingredient.
- the corticosteroid is weighed and put in the solvent. The solution is stirred until solubilization of the active ingredient.
- phase II The two active phases are incorporated in phase I under stirring.
- the mixture is homogenised.
- the corticosteroid is added to the parent solution of vitamin D analogue.
- the objective of this study was to compare a fixed-combination of calcitriol 3 ⁇ g/g and clobetasol propionate 250 ⁇ g/g (composition of example 1 ) by evaluation of its blanching capacity to three marketed corticosteroids formulations:
- Diprolene ® cream (betamethasone dipropionate 500 ⁇ g/g)
- Daivobet ® ointment fixed-combination containing calcipotriol 50 ⁇ g/g and betamethasone dipropionate 500 ⁇ g/g).
- the creams of reference do not contain a combination of silicone and volatile solvent.
- the tested products were randomly allocated to pre-marked 2.2 cm diameter sites on forearms. Applications were performed by a trained research assistant out of the sight of the blanching evaluators. The study products were administrated as six hours non occlusive application.
- Safety assessment was conducted for all subjects at every visit after enrolment in the study.
- the primary parameter for the safety measurement was the record of adverse events.
- the analyzed variable was the mean of the two evaluators' scores on each site.
- the area under the curve was calculated by subject and by treatment from TO (before application) up to T28h (22 hours after product removal).
- the chromametric variables a * and L * were adjusted according to their baseline value before applicatiom- ⁇ a* and ⁇ L*.
- the area under the curve was calculated by subject and by treatment from TO (before application up to T28h (22 hours after product removal).
- the areas under the curve were submitted, by parameter, to analyses of variance including subject, zone and treatment as factors in the model.
- the treatments were compared and classified using a Tukey multiple comparison test, which was performed at the 5% two sided significance level.
- the analyzed variable was the area under the curve (AUC) of mean of the two evaluators' scores on each site. This AUC was calculated by subject and by treatment from TO (before application) up to T28h (22 hours after product removal). These data are summarized in Table 2 below :
- the chromametric parameters L* and a * supported the results obtained from visual scores.
- Clobetasol-17-propionate was shown to accumulate in the Stratum corneum 16 hours after application on a human skin (Franz' cells). Table 3 :
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dispersion Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US68928205P | 2005-06-10 | 2005-06-10 | |
PCT/EP2006/005831 WO2006131401A2 (en) | 2005-06-10 | 2006-05-22 | Controlled release of a drug through skin on the basis of a topical composition comprising a drug, a film-forming silicone and at least one volatile solvent |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1901709A2 true EP1901709A2 (en) | 2008-03-26 |
Family
ID=37137556
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP06754427A Withdrawn EP1901709A2 (en) | 2005-06-10 | 2006-05-22 | Controlled release of a drug through skin on the basis of a topical composition comprising a drug, a film-forming silicone and at least one volatile solvent |
Country Status (11)
Country | Link |
---|---|
EP (1) | EP1901709A2 (ja) |
JP (1) | JP2008542423A (ja) |
KR (1) | KR20080016612A (ja) |
CN (1) | CN101247787B (ja) |
AR (1) | AR054381A1 (ja) |
AU (1) | AU2006256860B2 (ja) |
BR (1) | BRPI0613230A2 (ja) |
CA (1) | CA2610755A1 (ja) |
MX (1) | MX2007015672A (ja) |
RU (1) | RU2008100037A (ja) |
WO (1) | WO2006131401A2 (ja) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2909284B1 (fr) * | 2006-11-30 | 2012-09-21 | Galderma Sa | Nouvelles compositions sous forme d'onguent sans vaseline comprenant un derive de vitamine d et eventuellement un anti-inflammatoire steroidien |
MX2009009557A (es) * | 2007-03-08 | 2010-08-10 | Crescendo Therapeutics Llc | Formulaciones de aposito para prevenir o reducir la cicatrizacion. |
EP2167036B1 (en) * | 2007-07-11 | 2013-09-18 | Dow Corning Corporation | Compositions for delivering a drug |
BR112012001098A2 (pt) * | 2009-07-09 | 2015-09-01 | Crescendo Therapeutics Llc | Método de cicatrização de feridas e modulação de cicatriz |
US9254296B2 (en) | 2009-12-22 | 2016-02-09 | Leo Pharma A/S | Pharmaceutical composition comprising vitamin D analogue and cosolvent-surfactant mixture |
AU2009357263B2 (en) * | 2009-12-22 | 2015-04-09 | Leo Pharma A/S | Pharmaceutical composition comprising vitamin D analogue and cosolvent-surfactant mixture |
US20160095876A1 (en) | 2014-10-01 | 2016-04-07 | Rochal Industries, Llp | Composition and kits for inhibition of pathogenic microbial infection and methods of using the same |
TW201636025A (zh) * | 2015-04-15 | 2016-10-16 | Maruho Kk | 皮膚用之醫藥組成物 |
KR20190026397A (ko) | 2017-09-05 | 2019-03-13 | 안준배 | 노이즈 필터링 장치 및 방법 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006005845A1 (fr) * | 2004-06-17 | 2006-01-19 | Galderma S.A. | Composition sous forme de spray comprenant une association de calcitriol et de propionate de clobetasol, une phase alcoolique, au moins un silicone volatile et une phase huileuse non volatile |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
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US5122519A (en) * | 1989-06-27 | 1992-06-16 | American Cyanamid Company | Stable, cosmetically acceptable topical gel formulation and method of treatment for acne |
JPH03275619A (ja) * | 1990-03-23 | 1991-12-06 | Nitsusui Seiyaku Kk | 外用剤組成物 |
JP3251717B2 (ja) * | 1992-06-29 | 2002-01-28 | 花王株式会社 | 皮膚外用剤 |
JP3573803B2 (ja) * | 1994-02-16 | 2004-10-06 | ポーラ化成工業株式会社 | 皮膚外用剤 |
BR9708081A (pt) * | 1996-03-16 | 1999-07-27 | Hoechst Ag | Formulações tópicas para tratamento de psóriase de unhas |
GB9902812D0 (en) * | 1998-06-18 | 1999-03-31 | Dow Corning Sa | Composition for delivering pharmaceutically active agents |
US6200964B1 (en) * | 1999-05-28 | 2001-03-13 | Neutrogena Corporation | Silicone gel containing salicylic acid |
WO2000072817A1 (en) * | 1999-05-28 | 2000-12-07 | Neutrogena Corporation | Water-in-oil emulsion comprising a silicone gel containing vitamin c |
US6365670B1 (en) * | 2000-03-10 | 2002-04-02 | Wacker Silicones Corporation | Organopolysiloxane gels for use in cosmetics |
DE10019128A1 (de) * | 2000-04-18 | 2001-11-15 | Wella Ag | Aerosolschaum zur Haarbehandlung |
US6410038B1 (en) * | 2000-06-14 | 2002-06-25 | Dow Corning Corporation | Water-in-oil-in-polar solvent emulsions |
PL212660B1 (pl) * | 2000-10-27 | 2012-11-30 | Leo Pharma As | Zasadniczo niewodna zelowa kompozycja farmaceutyczna do podawania na skóre oraz jej zastosowanie |
JP2004189639A (ja) * | 2002-12-09 | 2004-07-08 | Pola Chem Ind Inc | 乳化組成物 |
US20040228821A1 (en) * | 2003-05-16 | 2004-11-18 | The Procter & Gamble Company | Personal care products comprising active agents in a gel network |
WO2005053666A1 (en) * | 2003-11-21 | 2005-06-16 | Galderma Research & Development, S.N.C. | Sprayable composition for the administration of vitamin d derivatives |
-
2006
- 2006-05-22 JP JP2008515155A patent/JP2008542423A/ja active Pending
- 2006-05-22 MX MX2007015672A patent/MX2007015672A/es not_active Application Discontinuation
- 2006-05-22 EP EP06754427A patent/EP1901709A2/en not_active Withdrawn
- 2006-05-22 RU RU2008100037/14A patent/RU2008100037A/ru unknown
- 2006-05-22 CA CA002610755A patent/CA2610755A1/en not_active Abandoned
- 2006-05-22 BR BRPI0613230-8A patent/BRPI0613230A2/pt not_active IP Right Cessation
- 2006-05-22 AU AU2006256860A patent/AU2006256860B2/en not_active Expired - Fee Related
- 2006-05-22 KR KR1020077028565A patent/KR20080016612A/ko not_active Application Discontinuation
- 2006-05-22 WO PCT/EP2006/005831 patent/WO2006131401A2/en active Application Filing
- 2006-05-22 CN CN2006800204905A patent/CN101247787B/zh not_active Expired - Fee Related
- 2006-06-08 AR ARP060102384A patent/AR054381A1/es unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006005845A1 (fr) * | 2004-06-17 | 2006-01-19 | Galderma S.A. | Composition sous forme de spray comprenant une association de calcitriol et de propionate de clobetasol, une phase alcoolique, au moins un silicone volatile et une phase huileuse non volatile |
Also Published As
Publication number | Publication date |
---|---|
AU2006256860A1 (en) | 2006-12-14 |
JP2008542423A (ja) | 2008-11-27 |
AU2006256860B2 (en) | 2012-04-19 |
RU2008100037A (ru) | 2009-07-20 |
BRPI0613230A2 (pt) | 2011-01-04 |
WO2006131401A2 (en) | 2006-12-14 |
MX2007015672A (es) | 2008-02-20 |
CN101247787A (zh) | 2008-08-20 |
WO2006131401A3 (en) | 2007-03-15 |
AR054381A1 (es) | 2007-06-20 |
CN101247787B (zh) | 2011-10-05 |
KR20080016612A (ko) | 2008-02-21 |
CA2610755A1 (en) | 2006-12-14 |
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