[go: up one dir, main page]

WO2011070318A2 - Formulation topique - Google Patents

Formulation topique Download PDF

Info

Publication number
WO2011070318A2
WO2011070318A2 PCT/GB2010/002240 GB2010002240W WO2011070318A2 WO 2011070318 A2 WO2011070318 A2 WO 2011070318A2 GB 2010002240 W GB2010002240 W GB 2010002240W WO 2011070318 A2 WO2011070318 A2 WO 2011070318A2
Authority
WO
WIPO (PCT)
Prior art keywords
topical formulation
ibuprofen
propylene glycol
water
alcohol
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.)
Ceased
Application number
PCT/GB2010/002240
Other languages
English (en)
Other versions
WO2011070318A3 (fr
Inventor
Andrew Kirkwood
Adrian Davis
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.)
Reckitt Benckiser Healthcare International Ltd
Original Assignee
Reckitt Benckiser Healthcare International Ltd
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 Reckitt Benckiser Healthcare International Ltd filed Critical Reckitt Benckiser Healthcare International Ltd
Publication of WO2011070318A2 publication Critical patent/WO2011070318A2/fr
Publication of WO2011070318A3 publication Critical patent/WO2011070318A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • 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
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; 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
    • 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
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • the present invention relates to a topical pharmaceutical composition having improved skin penetration properties but with aesthetics that meet consumer and patient expectations and ensure compliance.
  • the present invention relates to such a topical pharmaceutical aqueous gel having improved skin penetration properties which comprises an NSAID.
  • Transdermal delivery for local or regional effect of pharmaceutically active compounds, was developed to address the problems associated with orally taken drug formulations, e.g. actives breaking down in the organs in the body such as the liver and without the necessity for the whole body to be treated.
  • transdermal technology was driven by the development of patches.
  • the technology maintained the drug at saturation levels and included a moderately polar solvent, but with a lipid enhancer, often a fatty acid, alcohol or ester derivative.
  • a moderately polar solvent also increased the lipid enhancer solubility in the stratum corneum barrier, and the lipid enhancer also increased the polar solvent diffusivity, synergy was often found with this "co-enhancer" technology.
  • Propylene glycol is an excellent solvent for many drugs and, as discussed, has been widely used to enhance the skin penetration of range of drugs, including antivirals, corticosteroids, testosterone, antihistamines, cardiovasculars and nonsteroidals including ibuprofen.
  • propylene glycol especially at the high concentration required to demonstrate an enhancer effect, is extremely hydroscopic and thus tacky to the touch which limits consumer and patient acceptance and compliance.
  • propylene glycol may be replaced by enhancers such as Transcutol or dimethyl isosorbide, these are not as effective and also suffer from poor aesthetics.
  • Propylene glycol is immiscible with many fatty acid derivatives, for example isopropyl myristate, such that the mixture is a two-phase system.
  • WO 02/1 1768 discloses compositions which comprise a fatty alcohol and a diethylene glycol monoalcohol ether.
  • the compositions further include Carbomer as a gelling agent.
  • the lipid enhancers used in combination with propylene glycol include straight chain saturated fatty acid, broadly from C 8 -C 16 and commonly selecting from the fatty acid, fatty alcohol of fatty ester derivatives. Because propylene glycol penetrates into and through the stratum corneum barrier of the skin much faster than fatty acid derivatives, much higher doses of propylene glycol are required, and for optimum effect the fatty acid should be present at around 5% of the dose of propylene glycol.
  • C 12 -C 14 fatty acids isopropyl esters are only miscible at 1-2% of propylene glycol and are not optimised.
  • C12 fatty acid alcohol is very miscible with propylene glycol and when present at around 5% of the dose of propylene glycol would itself be at a low degree of saturation which would limit its skin penetration enhancement potential.
  • the C 12 -C 14 fatty acids have a further benefit in that they are relatively more soluble in propylene glycol-water, than, for example, the corresponding esters and alcohols.
  • Water-propylene glycol bases are much more acceptable from a cosmetic perspective than propylene glycol alone, but would be expected to have reduced skin penetration due to the reduced propylene glycol concentrations. Niall, this statement is probably true, especially at the pH of Bronson, but I don't know for sure. Of course, as we state, the alcohol is more soluble in propylene glycol. I would leave this in. It is a nice idea and adds to the story.
  • Ibuprofen is a potent NSAID with moderately good skin penetration.
  • the onset, intensity and duration of local analgesic and antiinflammatory activity may be improved by use of skin penetration enhancers, including propylene glycol.
  • skin penetration enhancers including propylene glycol.
  • ibuprofen is a low melting point drug, melting at around 70 degrees centrigrade, and consequently has relatively high solubility in most solvent.
  • Herkenne et al. have shown that the saturated solubility of ibuprofen in propylene glycol is in excess of 40% w/v whereas that in water is only approximately 0.014% w/v.
  • the use of propylene glycol alone, or in the presense of a low concentration of a fatty acid dervative, such as a C 12 -C 14 fatty acid has the disadvantage that at 5% of ibuprofen (the amount normally contained in topical products) the drug is at a low level of saturation (of approximately l/8 th saturation) which serves to reduce the overall skin penetration of ibuprofen from propylene glycol alone-fatty acid systems, such as propylene glycol C 12 or C 14 fatty acid.
  • a topical formulation comprising:
  • a gelling agent selected from the group consisting of non-ionic polymers
  • the formulation can be in the form of a gel.
  • the NSAID can be selected from the group consisting of ibuprofen, ketoprofen, flurbiprofen, diclofenac, naproxen.
  • the NSAID can be selected from ibuprofen, ketoprofen or naproxen.
  • the polyhydric alcohol is selected from the group consisting of monomeric polyhydric alcohols such as a C 2 - C 6 glycol, or polymeric polyhydric alcohols such polyethylene glycol, polypropylene glycol or mixtures thereof.
  • the polyhydric alcohol can be propylene glycol or butylene glycol.
  • the fatty acid is preferably lauric acid, or myristic acid.
  • a preferred C 2 - C 4 alcohol is isopropyl alcohol.
  • the ratio of water: C 2 - C 4 alcohol is from 90%: 10% to 50%:50%.
  • the ratio of fatty acid to polyhydric alcohol is from 1%:99% to 15%:85%.
  • a preferred ratio is 5%:95% to 10%:90%.
  • the gelling agent can be selected from hydroxyethyl cellulose, hydroxyeihylmethyl cellulose, hydroxymethylpropyl cellulose, hydroxypropyl cellulose, and polyacrylamide-based gelling agents such as those marketed under the Carbopol brand name.
  • Preferred gelling agents are hydroxypropyl cellulose or hydroxyethyl cellulose.
  • the optional pharmaceutical excipients include one or more diluents, one or more colourings, pH controlling agents, fillers, flow aids, preservatives, antioxidants, moisture scavengers, colourants and processing aids.
  • a preferred excipient is a pH controlling agent such as an acid or a base.
  • a base such as sodium hydroxide or potassium hydroxide is a preferred pH controlling agent, although any pharmaceutically acceptable base may be used.
  • the compositions can include an additional analgesic agent. Typically, the compositions do not contain pharmaceutically active compounds other than analgesics.
  • the gel can comprise
  • Sensorially active ingredients that stimulate the cold and warm receptors in the skin and artificially produce a cool or warming feeling may also be considered for inclusion.
  • Example of such materials include Menthol and Capsaicin which target cooling and warming receptor respectively and can be used to improve formulation organoleptics.
  • the gel can further comprise up to 10% menthol.
  • the gel can comprise
  • composition consists essentially of components (a) to (h).
  • gel comprises
  • the gel comprises
  • Figure 1 illustrates the miscibility of FAD in 100% propylene glycol against FAD type and carbon chain length.
  • Figure 2 illustrates the amount of ibuprofen in ⁇ g/cm 2 penetrated with time from Ibugel and two experimental formulations one containing hydroxylethyl cellulose (HHX) and one containing hydroxypropyl cellulose (HF); and
  • Figure 3 illustrates the percentage of dose of applied ibuprofen penetrated with time from Ibugel and two experimental formulations one containing hydroxylethyl cellulose (HHX) and one containing hydroxypropyl cellulose (HF).
  • HHX hydroxylethyl cellulose
  • HF hydroxypropyl cellulose
  • the formulations can be made in the following way.
  • propylene glycol (42.3 lg) was added to lauric acid(4.19g) and the resulting mixture was heated (to 60-70°C) while mixing for at least 5 minutes or until a clear solution is formed.
  • Ibuprofen (5.00g) was added with stirring for 5 minutes.
  • an aqueous solution of sodium hydroxide (0.50g) in deionised water (31.55g) was prepared. The aqueous sodium hydroxide solution was added to the propylene glycol/lauric acid mixture, and stirring was continued for a minimum of 5 minutes.
  • a solution of isopropyl alcohol (13.95g) and the hydroxyethyl cellulose (1.50g) was prepared, and to this solution was added menthol with further stirring for a minimum of 10 minutes or until the menthol is dissolved.
  • the resulting isopropyl alcohol/hydroxyethyl cellulose/menthol mixture was added to the solution of aqueous sodium hydroxide, propylene glycol and lauric acid. The combined mixture was gently stirred for a a minimum of 2 hours until a homogeneous mixture was formed.
  • Example formulations Nos 1 & 2 of non-aqueous and an aqueous alcoholic gel are given below in Tables 1 & 2 respectively:
  • the ratio of lauric acid-PG to IPA was chosen as 70:30.
  • Hydroxypropyl cellulose was chosen as a gelling agent for this solvent- rich gel.
  • Table 2 there is shown an aqueous alcoholic (IPA) gel (example 2) based on Ci 2 acid (lauric acid)-PG residual phase.
  • IPA aqueous alcoholic
  • Table 3 (examples 3 & 4) shows the actual batch weights and theoretical weights (in brackets) for 20 g nominal batches and tested for in-vitro skin penetration. All weights are in grams.
  • Figure 1 summarises the trends by plotting miscibility in 100% propylene glycol (actual or extrapolated figures) against FAD type and carbon chain length. The result are exactly as expected.
  • miscibility decreases in the order alcohol > acid > ester reflecting their increasing differense in polarity with propylene glycol.
  • C 14 there is a similar, though less pronounced trend, as the carbon chain becomes more dominant in governing the physicochemistry and the miscibilities of acid and isopropyl ester are very similar.
  • Figures 2 and 3 below show the skin penetration of ibuprofen from Ibugel and the two experimental gel formulations expressed as amount permeated with time and as percentage of dose with time, respectively.
  • the ratio of isopropyl alcohol : water is 30 : 70. This takes account of the water that is part of the 10% NaOH (aq) solution - in l Og of a 10% NaOH solution there is 0.5g and 9.5g water.
  • Ibuprofen aqueous gels and other formulation types based upon them have potential to improve ibuprofen skin penetration and therapeutic effect.
  • formulations of the present application exhibit good tolerance (i.e. reduced irritation and sensitisation) and good ergonomics (ease of use, including packaging).

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Dispersion Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Dermatology (AREA)
  • Pain & Pain Management (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Rheumatology (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La présente invention porte sur une formulation topique qui comporte (a) un AINS ou un sel de qualité pharmaceutique de celui-ci; (b) un polyol; (c) un acide gras à chaîne droite en C10-C14 ou un dérivé de celui-ci; (d) un alcool en C2-C4; (e) un agent gélifiant choisi dans le groupe constitué par les polymères non ioniques; (f) éventuellement des excipients de qualité pharmaceutique supplémentaires, et (g) de l'eau pour obtenir 100 %. La formulation topique présente des propriétés de pénétration de la peau améliorées.
PCT/GB2010/002240 2009-12-11 2010-12-06 Formulation topique Ceased WO2011070318A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0921686.2 2009-12-11
GBGB0921686.2A GB0921686D0 (en) 2009-12-11 2009-12-11 Topical formulation

Publications (2)

Publication Number Publication Date
WO2011070318A2 true WO2011070318A2 (fr) 2011-06-16
WO2011070318A3 WO2011070318A3 (fr) 2011-10-20

Family

ID=41666943

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2010/002240 Ceased WO2011070318A2 (fr) 2009-12-11 2010-12-06 Formulation topique

Country Status (3)

Country Link
GB (2) GB0921686D0 (fr)
TW (1) TW201129396A (fr)
WO (1) WO2011070318A2 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012151427A1 (fr) 2011-05-03 2012-11-08 Aponia Laboratories, Inc. Compositions transdermiques d'ibuprofène et leurs méthodes d'utilisation
WO2016132159A1 (fr) * 2015-02-20 2016-08-25 Futura Medical Developments Limited Formulation pharmaceutique topique
WO2016139471A1 (fr) * 2015-03-03 2016-09-09 Adrian Davis Formulation topique
WO2017212260A1 (fr) * 2016-06-07 2017-12-14 Futura Medical Developments Limited Formulation pharmaceutique topique
GB2597526A (en) 2020-07-27 2022-02-02 Incanthera R&D Ltd Topical formulation
WO2022023348A1 (fr) 2020-07-27 2022-02-03 Incanthera (R&D) Ltd Formulation topique
US11717593B2 (en) 2013-03-13 2023-08-08 Avery Dennison Corporation Improving adhesive properties
US12150920B2 (en) 2020-04-06 2024-11-26 Algotherapeutix Topical pharmaceutical composition in the form of aqueous gel comprising at least amitriptyline

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10596117B1 (en) 2014-12-31 2020-03-24 Eric Morrison Lipoleosomes as carriers for aromatic amide anesthetic compounds
US10561627B2 (en) 2014-12-31 2020-02-18 Eric Morrison Ibuprofen nanoparticle carriers encapsulated with hermetic surfactant films
US11007161B1 (en) 2014-12-31 2021-05-18 Eric Morrison Ibuprofen nanoparticle carriers encapsulated with hermatic surfactant films

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002011768A1 (fr) 2000-08-03 2002-02-14 Antares Pharma Ipl Ag Composition pour l'administration transdermique et/ou transmuqueuse de composes actifs assurant des niveaux d'efficacite therapeutique adequats

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2023000B (en) * 1978-06-17 1982-10-13 Kowa Co Antinflammatory analgesic gelled ointments
CH655656B (fr) * 1982-10-07 1986-05-15
DE3532562A1 (de) * 1985-09-12 1987-03-12 Dolorgiet Gmbh & Co Kg Transdermal resorbierbare, wasserhaltige zubereitungen von arylpropionsaeurederivaten und verfahren zur herstellung derselben
US5093133A (en) * 1990-01-24 1992-03-03 Mcneil-Ppc, Inc. Method for percutaneous delivery of ibuprofen using hydroalcoholic gel
CN1106259A (zh) * 1994-02-05 1995-08-09 日东制药株式会社 含有作为有效成分的丙酸类非类固醇性药物的新颖消炎镇痛外用凝胶制剂
CN1210463A (zh) * 1996-02-07 1999-03-10 株式会社津村 透明双氯芬酸钠的水溶液以及它的药物组合物
US6083996A (en) * 1997-11-05 2000-07-04 Nexmed Holdings, Inc. Topical compositions for NSAI drug delivery
JP2003095983A (ja) * 2001-09-21 2003-04-03 Lion Corp 皮膚外用剤組成物
ATE440598T1 (de) * 2007-03-02 2009-09-15 Flamek Corp Ou Analgesische zusammensetzung von topisch angewendeten, nichtsteroiden und entzündungshemmenden arzneimitteln und opioiden
EP2055298A1 (fr) * 2007-10-30 2009-05-06 Novartis AG Composition topique
US20090246273A1 (en) * 2008-03-27 2009-10-01 Al-Ghananeem Abeer M Ketorolac Sublingual Spray for the Treatment of Pain

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002011768A1 (fr) 2000-08-03 2002-02-14 Antares Pharma Ipl Ag Composition pour l'administration transdermique et/ou transmuqueuse de composes actifs assurant des niveaux d'efficacite therapeutique adequats

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2704703A4 (fr) * 2011-05-03 2014-12-03 Aponia Lab Inc Compositions transdermiques d'ibuprofène et leurs méthodes d'utilisation
US9205041B2 (en) 2011-05-03 2015-12-08 Aponia Laboratories, Inc. Transdermal compositions of ibuprofen and methods of use thereof
WO2012151427A1 (fr) 2011-05-03 2012-11-08 Aponia Laboratories, Inc. Compositions transdermiques d'ibuprofène et leurs méthodes d'utilisation
US11419814B2 (en) 2011-05-03 2022-08-23 Aponia Laboratories, Inc. Transdermal compositions of ibuprofen and methods of use thereof
US9849080B2 (en) 2011-05-03 2017-12-26 Aponia Laboratories, Inc. Transdermal compositions of ibuprofen and methods of use thereof
US10821071B2 (en) 2011-05-03 2020-11-03 Aponia Laboratories, Inc. Transdermal compositions of ibuprofen and methods of use thereof
US11717593B2 (en) 2013-03-13 2023-08-08 Avery Dennison Corporation Improving adhesive properties
US10028927B2 (en) 2015-02-20 2018-07-24 Futura Medical Developments Limited Topical pharmaceutical formulation
WO2016132159A1 (fr) * 2015-02-20 2016-08-25 Futura Medical Developments Limited Formulation pharmaceutique topique
GB2549418A (en) * 2015-03-03 2017-10-18 Davis Adrian Topical formulation
GB2549418B (en) * 2015-03-03 2018-05-23 Limeway Pharma Design Ltd Topical formulations comprising dimethicone macromers
JP2018507219A (ja) * 2015-03-03 2018-03-15 デイヴィス, エイドリアンDAVIS, Adrian 局所製剤
US10828250B2 (en) 2015-03-03 2020-11-10 Limeway Pharma Design Limited Topical formulation
WO2016139471A1 (fr) * 2015-03-03 2016-09-09 Adrian Davis Formulation topique
US11376213B2 (en) 2016-06-07 2022-07-05 Futura Medical Developments Limited Topical pharmaceutical formulation
WO2017212260A1 (fr) * 2016-06-07 2017-12-14 Futura Medical Developments Limited Formulation pharmaceutique topique
US12150920B2 (en) 2020-04-06 2024-11-26 Algotherapeutix Topical pharmaceutical composition in the form of aqueous gel comprising at least amitriptyline
US12156854B2 (en) 2020-04-06 2024-12-03 Algotherapeutix Topical pharmaceutical composition in the form of aqueous gel comprising at least amitriptyline
GB2597526A (en) 2020-07-27 2022-02-02 Incanthera R&D Ltd Topical formulation
WO2022023348A1 (fr) 2020-07-27 2022-02-03 Incanthera (R&D) Ltd Formulation topique

Also Published As

Publication number Publication date
GB0921686D0 (en) 2010-01-27
GB2476155A (en) 2011-06-15
WO2011070318A3 (fr) 2011-10-20
GB201020601D0 (en) 2011-01-19
TW201129396A (en) 2011-09-01

Similar Documents

Publication Publication Date Title
WO2011070318A2 (fr) Formulation topique
CN102711835B (zh) 局部布洛芬制剂
US5654337A (en) Topical formulation for local delivery of a pharmaceutically active agent
RU2468794C2 (ru) Фармацевтическая композиция для топического применения
CN101790370B (zh) 一种新的双氯芬酸非水局部用溶液及其制备方法
JPWO2009037813A1 (ja) 経皮吸収製剤
JP6921493B2 (ja) 水中油型乳化組成物
WO2004035054A1 (fr) Timbre transdermique a usage externe renfermant du fentanyle
EP2237805A1 (fr) Formulation d'imiquimod
JP5421063B2 (ja) ジクロフェナクナトリウム含有水性貼付剤
CN106604717A (zh) 局部用双氯芬酸钠组合物
TW200403077A (en) Trans-dermal absorption preparation
JP4195178B2 (ja) 消炎鎮痛外用剤
JP3226940B2 (ja) 経皮投与製剤
JP2000143510A (ja) 外用組成物
JP4626202B2 (ja) ピロキシカム含有外用消炎鎮痛剤組成物
JPH11199482A (ja) 外用剤組成物
WO2016121996A1 (fr) Préparation aqueuse à usage externe
JPH111433A (ja) トルナフテ−ト含有液剤
EP2340016A2 (fr) Formule topique de dihydrate propionate 3-(2,2,2-trimethylhydrazinium)
JPH10182458A (ja) インドメタシン含有外用剤組成物
WO1992020376A1 (fr) Composition de promoteur de l'absorption percutanee et preparation externe pour l'administration de medicaments par voie percutanee
JP2516481B2 (ja) 消炎鎮痛ゲル製剤
JPH05117141A (ja) 副腎エキス含有消炎鎮痛ゲル剤
WO2007046318A1 (fr) Preparation liquide pour application externe contenant de l'indomethacine

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10807340

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 10807340

Country of ref document: EP

Kind code of ref document: A2