WO2008110741A2 - Topical pharmaceutical formulation - Google Patents

Topical pharmaceutical formulation Download PDF

Info

Publication number
WO2008110741A2
WO2008110741A2 PCT/GB2008/000540 GB2008000540W WO2008110741A2 WO 2008110741 A2 WO2008110741 A2 WO 2008110741A2 GB 2008000540 W GB2008000540 W GB 2008000540W WO 2008110741 A2 WO2008110741 A2 WO 2008110741A2
Authority
WO
WIPO (PCT)
Prior art keywords
composition according
diclofenac
ester
polyhydric alcohol
glycol ether
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/GB2008/000540
Other languages
English (en)
French (fr)
Other versions
WO2008110741A3 (en
WO2008110741A8 (en
Inventor
Adrian Francis 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.)
FUTURA MEDICAL DEVELOPMENTS Ltd
Original Assignee
FUTURA MEDICAL DEVELOPMENTS 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
Priority to DK08709428.0T priority Critical patent/DK2131813T3/da
Priority to ES08709428T priority patent/ES2391914T3/es
Priority to BRPI0808887-0A priority patent/BRPI0808887A2/pt
Priority to AU2008224735A priority patent/AU2008224735B2/en
Priority to RU2009136228/15A priority patent/RU2468794C2/ru
Priority to PL08709428T priority patent/PL2131813T3/pl
Priority to CA2680074A priority patent/CA2680074C/en
Priority to US12/530,960 priority patent/US8541470B2/en
Priority to JP2009553196A priority patent/JP2010521442A/ja
Application filed by FUTURA MEDICAL DEVELOPMENTS Ltd filed Critical FUTURA MEDICAL DEVELOPMENTS Ltd
Priority to NZ579895A priority patent/NZ579895A/en
Priority to UAA200910111A priority patent/UA100509C2/ru
Priority to MX2009009758A priority patent/MX2009009758A/es
Priority to EP08709428A priority patent/EP2131813B1/en
Publication of WO2008110741A2 publication Critical patent/WO2008110741A2/en
Publication of WO2008110741A3 publication Critical patent/WO2008110741A3/en
Anticipated expiration legal-status Critical
Publication of WO2008110741A8 publication Critical patent/WO2008110741A8/en
Ceased legal-status Critical Current

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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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]
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/08—Solutions

Definitions

  • NSAID drugs have been formulated for topical-regional delivery including salicylates, indomethacin, piroxicam, ketop physician, diclofenac and others.
  • Effective topical therapy requires the achievement of therapeutic drug concentrations at the target site and depends among other things on drag potency and the extent of skin penetration.
  • diclofenac, ketorolac and ketoprofen are preferred; in particular, the efficacy index for diclofenac is greater than that for piroxicam by a factor in the order of 10 3 demonstrating the importance of correct drug selection.
  • Diclofenac and ketoprofen are particularly preferred on the basis of their more rapid systemic clearance compared with other drugs.
  • the NSAJD which is preferred for use as the active ingredient in compositions according to the ⁇ invention is diclofenac, due to its cyclo-oxygenase activity in relation to pain and inflammation and because its numerical ratio of skin penetration to potency is superior to most if not all other NSAIDs.
  • diclofenac is used as diclofenac acid, it having been found that, in compositions accordinging to the invention, the acid has a significantly higher membrane permeability than salt forms," thus compensating for its relatively low solubility.
  • Other possible NSAIDs for use in the present invention include ketorolac and ketoprofen.
  • the amount of the NSAID in compositions according to the invention may be up to 10% by weight, preferably up to 5% by weight or more preferably up to 2.5% by weight.
  • the ratio of polyhydric alcohol to glycol ether is preferably in the range 80:20 to 30:70, more preferably 70:30 to 40:60, with the ester ranging from 2 to 20%, more preferably 3 to 10% by weight.
  • one formulation according to the invention contains propylene glycol and Transcutol at a ratio by weigh of 70:30 with isopropyl myristate at 3-3.5% by weight.
  • the composition also includes an antinucleating agent, to discourage recrystallisation of the drug component, which would lead to lower amounts being available for uptake. Nucleation and recrystallisation are likely to be most problematical where higher degrees of supersaturation are experienced in the residual phase.
  • compositions according to the invention may also include sensory signals, for example menthol and eucalyptus oil. Almost immediately after application these agents give a cooling sensation to the skin which is appreciated by users and heralds the onset of pain relief.
  • Other optional ingredients may be added to compositions according to the invention for formulation purposes depending on the intended mode of application, including thickening or gelling agents, propellants for spray formulations and so on.

Landscapes

  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Dermatology (AREA)
  • Neurosurgery (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Rheumatology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
PCT/GB2008/000540 2007-03-13 2008-02-15 Topical pharmaceutical formulation Ceased WO2008110741A2 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
JP2009553196A JP2010521442A (ja) 2007-03-13 2008-02-15 局所製剤処方
BRPI0808887-0A BRPI0808887A2 (pt) 2007-03-13 2008-02-15 Formulação farmacêutica tópica
NZ579895A NZ579895A (en) 2007-03-13 2008-02-15 Topical pharmaceutical formulation
RU2009136228/15A RU2468794C2 (ru) 2007-03-13 2008-02-15 Фармацевтическая композиция для топического применения
PL08709428T PL2131813T3 (pl) 2007-03-13 2008-02-15 Miejscowy preparat farmaceutyczny
CA2680074A CA2680074C (en) 2007-03-13 2008-02-15 Topical pharmaceutical formulation
US12/530,960 US8541470B2 (en) 2007-03-13 2008-02-15 Topical pharmaceutical formulation
DK08709428.0T DK2131813T3 (da) 2007-03-13 2008-02-15 Topiske, farmaceutiske formuleringer
AU2008224735A AU2008224735B2 (en) 2007-03-13 2008-02-15 Topical pharmaceutical formulation
ES08709428T ES2391914T3 (es) 2007-03-13 2008-02-15 Formulación farmacéutica tópica
UAA200910111A UA100509C2 (ru) 2007-03-13 2008-02-15 Фармацевтическая композиция для местного применения нестероидного противовоспалительного препарата
MX2009009758A MX2009009758A (es) 2007-03-13 2008-02-15 Formulacion farmaceutica topica.
EP08709428A EP2131813B1 (en) 2007-03-13 2008-02-15 Topical pharmaceutical formulation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0704846.5 2007-03-13
GBGB0704846.5A GB0704846D0 (en) 2007-03-13 2007-03-13 Topical pharmaceutical formulation

Publications (3)

Publication Number Publication Date
WO2008110741A2 true WO2008110741A2 (en) 2008-09-18
WO2008110741A3 WO2008110741A3 (en) 2009-03-12
WO2008110741A8 WO2008110741A8 (en) 2009-11-19

Family

ID=37988913

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2008/000540 Ceased WO2008110741A2 (en) 2007-03-13 2008-02-15 Topical pharmaceutical formulation

Country Status (21)

Country Link
US (1) US8541470B2 (https=)
EP (2) EP2452671A2 (https=)
JP (1) JP2010521442A (https=)
CN (1) CN101663022A (https=)
AU (1) AU2008224735B2 (https=)
BR (1) BRPI0808887A2 (https=)
CA (1) CA2680074C (https=)
CO (1) CO6220926A2 (https=)
DK (1) DK2131813T3 (https=)
ES (1) ES2391914T3 (https=)
GB (1) GB0704846D0 (https=)
MX (1) MX2009009758A (https=)
MY (1) MY149545A (https=)
NZ (1) NZ579895A (https=)
PL (1) PL2131813T3 (https=)
PT (1) PT2131813E (https=)
RU (1) RU2468794C2 (https=)
SG (1) SG179480A1 (https=)
TW (1) TWI367110B (https=)
UA (1) UA100509C2 (https=)
WO (1) WO2008110741A2 (https=)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9260446B2 (en) 2009-10-14 2016-02-16 Xenon Pharmaceuticals Inc. Synthetic methods for spiro-oxindole compounds
WO2016132159A1 (en) * 2015-02-20 2016-08-25 Futura Medical Developments Limited Topical pharmaceutical formulation
US9458178B2 (en) 2008-10-17 2016-10-04 Xenon Pharmaceuticals Inc. Spiro-oxindole compounds and their use as therapeutic agents
US9480677B2 (en) 2009-06-29 2016-11-01 Xenon Pharmaceuticals Inc. Enantiomers of spiro-oxindole compounds and their uses as therapeutic agents
US9487535B2 (en) 2012-04-12 2016-11-08 Xenon Pharmaceuticals Inc. Asymmetric syntheses for spiro-oxindole compounds useful as therapeutic agents
US9504671B2 (en) 2010-02-26 2016-11-29 Xenon Pharmaceuticals Inc. Pharmaceutical compositions of spiro-oxindole compound for topical administration and their use as therapeutic agents
FR3041534A1 (fr) * 2015-09-30 2017-03-31 Vetoquinol Sa Composition de nettoyant auriculaire
US9682033B2 (en) 2015-02-05 2017-06-20 Teva Pharmaceuticals International Gmbh Methods of treating postherpetic neuralgia with a topical formulation of a spiro-oxindole compound
WO2017212260A1 (en) * 2016-06-07 2017-12-14 Futura Medical Developments Limited Topical pharmaceutical formulation
US10100060B2 (en) 2016-06-16 2018-10-16 Xenon Pharmaceuticals Inc. Asymmetric synthesis of funapide
WO2022038332A1 (en) 2020-08-17 2022-02-24 Futura Medical Developments Limited Topical composition
US11826428B2 (en) 2010-10-29 2023-11-28 Infirst Healthcare Limited Solid solution compositions comprising cannabidiols
US11918654B2 (en) 2010-10-29 2024-03-05 Infirst Healthcare Limited Solid solution compositions and use in severe pain
US11992555B2 (en) 2010-10-29 2024-05-28 Infirst Healthcare Limited Solid solution compositions and use in chronic inflammation

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TR201906789T4 (tr) * 2003-11-20 2019-05-21 Novo Nordisk As Üretim ve enjeksiyon cihazlarında kullanım için en uygun olan propilen glikol ihtiva eden peptit formülasyonları.
US9271950B2 (en) 2010-10-29 2016-03-01 Infirst Healthcare Limited Compositions for treating chronic inflammation and inflammatory diseases
US11730709B2 (en) 2010-10-29 2023-08-22 Infirst Healthcare Limited Compositions and methods for treating severe pain
US8895536B2 (en) 2010-10-29 2014-11-25 Infirst Healthcare Ltd. Compositions and methods for treating chronic inflammation and inflammatory diseases
US10695432B2 (en) 2010-10-29 2020-06-30 Infirst Healthcare Limited Solid solution compositions and use in severe pain
US10695431B2 (en) 2010-10-29 2020-06-30 Infirst Healthcare Limited Solid solution compositions and use in cardiovascular disease
US9504664B2 (en) 2010-10-29 2016-11-29 Infirst Healthcare Limited Compositions and methods for treating severe pain
US9737500B2 (en) 2010-10-29 2017-08-22 Infirst Healthcare Limited Compositions and methods for treating severe pain
US9308213B2 (en) 2010-10-29 2016-04-12 Infirst Healthcare Limited Solid solution compositions and use in chronic inflammation
AU2014204739B2 (en) * 2013-01-14 2016-08-11 Infirst Healthcare Limited Compositions and methods for treating severe pain
ES2763352T3 (es) * 2013-01-14 2020-05-28 Infirst Healthcare Ltd Composiciones de solución sólida y uso en inflamación crónica
HK1218621A1 (zh) * 2013-02-04 2017-03-03 Infirst Healthcare Limited 用於治疗慢性炎症和炎性疾病的组合物及方法
US9012402B1 (en) 2014-06-11 2015-04-21 James Blanchard Gel for topical delivery of NSAIDs to provide relief of musculoskeletal pain and methods for its preparation
US11007161B1 (en) 2014-12-31 2021-05-18 Eric Morrison Ibuprofen nanoparticle carriers encapsulated with hermatic surfactant films
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
JP7250689B2 (ja) * 2017-03-07 2023-04-03 イッサム・リサーチ・ディベロップメント・カンパニー・オブ・ザ・ヘブルー・ユニバーシティ・オブ・エルサレム・リミテッド 活性化合物のための局所送達系
US10821075B1 (en) 2017-07-12 2020-11-03 James Blanchard Compositions for topical application of a medicaments onto a mammalian body surface
HRP20240485T1 (hr) 2017-08-24 2024-07-05 Novo Nordisk A/S Pripravci glp-1 i njihova upotreba
PE20230819A1 (es) 2020-02-18 2023-05-19 Novo Nordisk As Composiciones y usos de glp-1
GB2596286B (en) 2020-06-20 2023-01-25 Francis Davis Adrian Adherence to topical therapy
GB2597526A (en) 2020-07-27 2022-02-02 Incanthera R&D Ltd Topical formulation
CN116348099B (zh) 2020-07-27 2025-10-31 英加世瑞(研发)有限公司 局部用制剂

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JPH06104624B2 (ja) * 1986-05-07 1994-12-21 太郎 小木曽 経皮吸収剤
PE20011092A1 (es) * 2000-02-14 2001-11-12 Procter & Gamble Composiciones para el suministro topico de un agente farmaceuticamente activo que tiene reducida irritacion de la piel
DE10019171A1 (de) * 2000-04-07 2001-10-18 Schering Ag Zusammensetzungen zur Verwendung als Penetrationsverstärker in transdermalen Formulierungen für hoch lipophile Wirkstoffe
PE20040321A1 (es) * 2002-08-22 2004-07-15 Novartis Consumer Health Sa Composicion topica que comprende diclofenaco
US7132452B2 (en) * 2003-03-10 2006-11-07 Fang-Yu Lee Topical formulation having effects on alleviating pain/inflammation caused by herpes virus infection
WO2005027977A2 (en) * 2003-09-22 2005-03-31 Agis Industries (1983) Ltd. Diclofenac compositions for the treatment of skin disorders
EP1588697A1 (en) 2004-04-16 2005-10-26 Kurt H. Prof. Dr. Bauer Emulsion gel for topical application of pharmaceuticals
US20050244522A1 (en) 2004-04-30 2005-11-03 Carrara Dario Norberto R Permeation enhancer comprising genus Curcuma or germacrone for transdermal and topical administration of active agents

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9458178B2 (en) 2008-10-17 2016-10-04 Xenon Pharmaceuticals Inc. Spiro-oxindole compounds and their use as therapeutic agents
US9480677B2 (en) 2009-06-29 2016-11-01 Xenon Pharmaceuticals Inc. Enantiomers of spiro-oxindole compounds and their uses as therapeutic agents
US9260446B2 (en) 2009-10-14 2016-02-16 Xenon Pharmaceuticals Inc. Synthetic methods for spiro-oxindole compounds
US9504671B2 (en) 2010-02-26 2016-11-29 Xenon Pharmaceuticals Inc. Pharmaceutical compositions of spiro-oxindole compound for topical administration and their use as therapeutic agents
US11826428B2 (en) 2010-10-29 2023-11-28 Infirst Healthcare Limited Solid solution compositions comprising cannabidiols
US11918654B2 (en) 2010-10-29 2024-03-05 Infirst Healthcare Limited Solid solution compositions and use in severe pain
US11992555B2 (en) 2010-10-29 2024-05-28 Infirst Healthcare Limited Solid solution compositions and use in chronic inflammation
US9487535B2 (en) 2012-04-12 2016-11-08 Xenon Pharmaceuticals Inc. Asymmetric syntheses for spiro-oxindole compounds useful as therapeutic agents
US9682033B2 (en) 2015-02-05 2017-06-20 Teva Pharmaceuticals International Gmbh Methods of treating postherpetic neuralgia with a topical formulation of a spiro-oxindole compound
US10028927B2 (en) 2015-02-20 2018-07-24 Futura Medical Developments Limited Topical pharmaceutical formulation
WO2016132159A1 (en) * 2015-02-20 2016-08-25 Futura Medical Developments Limited Topical pharmaceutical formulation
FR3041534A1 (fr) * 2015-09-30 2017-03-31 Vetoquinol Sa Composition de nettoyant auriculaire
US11020344B2 (en) 2015-09-30 2021-06-01 Vetoquinol Sa Auricular cleaning composition
WO2017212260A1 (en) * 2016-06-07 2017-12-14 Futura Medical Developments Limited Topical pharmaceutical formulation
US11376213B2 (en) 2016-06-07 2022-07-05 Futura Medical Developments Limited Topical pharmaceutical formulation
US10100060B2 (en) 2016-06-16 2018-10-16 Xenon Pharmaceuticals Inc. Asymmetric synthesis of funapide
WO2022038332A1 (en) 2020-08-17 2022-02-24 Futura Medical Developments Limited Topical composition

Also Published As

Publication number Publication date
CA2680074C (en) 2016-07-12
GB0704846D0 (en) 2007-04-18
NZ579895A (en) 2012-02-24
DK2131813T3 (da) 2012-10-29
EP2131813A2 (en) 2009-12-16
RU2468794C2 (ru) 2012-12-10
UA100509C2 (ru) 2013-01-10
AU2008224735B2 (en) 2013-04-18
AU2008224735A1 (en) 2008-09-18
EP2452671A2 (en) 2012-05-16
US8541470B2 (en) 2013-09-24
CA2680074A1 (en) 2008-09-18
SG179480A1 (en) 2012-04-27
BRPI0808887A2 (pt) 2014-09-02
WO2008110741A3 (en) 2009-03-12
US20100099767A1 (en) 2010-04-22
TW200836769A (en) 2008-09-16
CN101663022A (zh) 2010-03-03
TWI367110B (en) 2012-07-01
PT2131813E (pt) 2012-10-31
WO2008110741A8 (en) 2009-11-19
ES2391914T3 (es) 2012-12-03
RU2009136228A (ru) 2011-04-20
MX2009009758A (es) 2009-09-24
EP2131813B1 (en) 2012-08-08
CO6220926A2 (es) 2010-11-19
JP2010521442A (ja) 2010-06-24
MY149545A (en) 2013-09-13
PL2131813T3 (pl) 2012-11-30

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