WO2007059584A1 - Methods for wound healing - Google Patents

Methods for wound healing Download PDF

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Publication number
WO2007059584A1
WO2007059584A1 PCT/AU2006/001781 AU2006001781W WO2007059584A1 WO 2007059584 A1 WO2007059584 A1 WO 2007059584A1 AU 2006001781 W AU2006001781 W AU 2006001781W WO 2007059584 A1 WO2007059584 A1 WO 2007059584A1
Authority
WO
WIPO (PCT)
Prior art keywords
euphorbia
wound
ingenol
wounds
subject
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/AU2006/001781
Other languages
English (en)
French (fr)
Inventor
Steven Martin Ogbourne
David Thomas
Ryan Moseley
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.)
Peplin Research Pty Ltd
Original Assignee
Peplin Research Pty 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 claimed from AU2005906601A external-priority patent/AU2005906601A0/en
Priority to US12/094,713 priority Critical patent/US20090215884A1/en
Priority to EP06817537A priority patent/EP1965818A4/en
Priority to NZ568168A priority patent/NZ568168A/en
Priority to BRPI0618926-1A priority patent/BRPI0618926A2/pt
Priority to JP2008541550A priority patent/JP2009517345A/ja
Application filed by Peplin Research Pty Ltd filed Critical Peplin Research Pty Ltd
Priority to CA002629899A priority patent/CA2629899A1/en
Priority to AU2006317523A priority patent/AU2006317523A1/en
Publication of WO2007059584A1 publication Critical patent/WO2007059584A1/en
Anticipated expiration legal-status Critical
Priority to US15/131,851 priority patent/US20160317486A1/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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/222—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having aromatic groups, e.g. dipivefrine, ibopamine
    • 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
    • A61K31/12—Ketones
    • A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
    • 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
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the first stage immediately following the infliction of the wound, such as a cutaneous wound, is referred to as hemostasis, whereby vasocontriction and clotting, mediated by fibrin and platelets, are initiated to control bleeding.
  • the clot further serves as a provisional matrix for incoming fibroblasts and inflammatory cells to the wound and as a reservoir of cytokines and growth factors.
  • Wound maturation may take as little as days or weeks but the complete process can last up to several years. During this phase contraction, decreased redness, decreased thickness, decreased induration and increased strength of the wound is observed. The wound contracts under the influence of myofibroblasts, collagen production in the granulation tissue decreases and blood vessels diminish. Wound healing is then completed by further re-epithelialization (Werner and Grose, 2003; Baum andArpey, 2005).
  • Migration is completed when the cells reach the outermost epidermal structure, the stratum corneum, a dry, waterproof squamous cell layer which helps to prevent desiccation of the underlying tissue.
  • This layer of dead epithelial cells is continuously being sloughed off and replaced by keratinized cells moving to the surface from the basement membrane. Because the epidermal epithelium is avascular, the basement membrane is dependent upon the dermis for its nutrient supply.
  • Particularly preferred species of the genus Monadenium include Monadenium lugardae and Monadenium guentheri.
  • R 4 is hydrogen, hydroxy or acyloxy, such as acetoxy.
  • alkynyl denotes groups formed from straight chain, branched or cyclic hydrocarbon residues containing at least one carbon-carbon triple bond including ethynically mono-, di- or poly- unsaturated alkyl or cycloalkyl groups as previously defined. Unless the number of carbon atoms is specified the term preferably refers to C 2-20 alkynyl (e.g. C 2-I o or C 2-6 ). Examples include ethynyl, 1-propynyl, 2-propynyl, and butynyl isomers, and pentynyl isomers. An alkynyl group may be optionally substituted by one or more optional substitutents as herein defined.
  • aryl denotes any of single, polynuclear, conjugated and fused residues of aromatic hydrocarbon ring systems.
  • aryl include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, tetrahydronaphthyl, anthracenyl, dihydroanthracenyl, benzanthracenyl, dibenzanthracenyl, phenanthrenyl, fluorenyl, pyrenyl, idenyl, azulenyl, chrysenyl.
  • Preferred aryl include phenyl and naphthyl.
  • Subjects which may be treated in accordance with the present invention include mammalian subjects: humans, primates, livestock animals (including cows, horses, sheep, pigs and goats), companion animals (including dogs, cats, rabbits, guinea pigs), and captive wild animals.
  • Laboratory animals such as rabbits, mice, rats, guinea pigs and hamsters are also contemplated as they may provide a convenient test system.
  • Non- mammalian species such as birds, amphibians and fish may also be contemplated in certain embodiments of the invention.
  • a subject may also be referred to herein as an individual, patient, animal or recipient.
  • Suitable effective amounts (dosage) and dosing regimens can be determined by the attending physician and may depend on the particular tissue type and wound being treated, the nature and severity of the wound, i.e. whether partial or full thickness, chronic or acute, as well as the general age, and health of the subject.
  • the ingenol compounds may be administered at a time deemed appropriate during the wound healing process. Thus, the ingenol compounds may be administered immediately or soon after the wound has occurred, and/or at any subsequent stage of the wound healing process to promote healing and/or reduce scarring and/or improve cosmesis.
  • the compounds may also be administered to existing scar tissue to minimize or reduce, inter alia, scarring, redness, thickness and/or hyper-or hypo-pigmentation.
  • Wound healing medicaments or compositions may contain the ingenol angelate compound in an amount of from about 0.0001% to up to 100% by weight.
  • the composition contains the ingenol compound in an amount of from about 0.0001% to up to about 10% by weight, for example about 0.0005, 0.001, 0.0025, 0.005, 0.01, 0.025, 0.05, 0.075, 0.1, 0.125, 0.15, 0.2, 0.25 or 0.5% to about 0.5, 1.0, 2.5 or 5.0%.
  • the ingenol compound is ingenol-3-angelate present in an amount of about 0.001 to about 1%.
  • the ingenol compounds may be administered in any suitable form, either locally, e.g. by topical application to the wound or by injection into the wound, or systemically, such as oral, parenteral (including subcutaneous, intramuscular, intravenous and intradermal), nasal, inhalation, rectal or vaginal administration.
  • suitable form either locally, e.g. by topical application to the wound or by injection into the wound, or systemically, such as oral, parenteral (including subcutaneous, intramuscular, intravenous and intradermal), nasal, inhalation, rectal or vaginal administration.
  • Preferred unit dosage compositions are those containing a daily dose or unit, daily sub- dose, as herein above described, or an appropriate fraction thereof, of the active ingredient.
  • the dermal fibroblast and epidermal keratinocyte culture medium were replaced with culture medium (100 ⁇ l/well), containing 0, 0.01 ⁇ g/ml, 0.1 ⁇ g/ml, 1 ⁇ g/ml, 10 ⁇ g/ml or 100 ⁇ g/ml PEP005 (six culture wells per PEP005 concentration).
  • the dermal fibroblast and epidermal keratinocyte cultures were maintained at 37°C, in a 5% CO 2 /95% air atmosphere, to 7 and 3 days respectively, with the respective PEP005-containing culture media, being changed every two days.
  • dermal fibroblasts The ability of dermal fibroblasts to remodel/reorganize their ECM environment in the presence of PEP005 was examined by fibroblast populated collagen lattices (FPCLs), according to Cook et al (2000). Following trypsinization, dermal fibroblasts were suspended in Fibroblast-Serum Containing Medium, containing 10% gelatinase-free, fetal calf serum (prepared using a gelatin-A Sepharose column, GE Healthcare Ltd., Buckinghamshire, U.K.), to remove endogenous MMP -2 and MMP-9 activity.
  • Fibroblast-Serum Containing Medium containing 10% gelatinase-free, fetal calf serum (prepared using a gelatin-A Sepharose column, GE Healthcare Ltd., Buckinghamshire, U.K.), to remove endogenous MMP -2 and MMP-9 activity.
  • Fibroblast-Serum Containing Medium was replaced with culture medium (250 ⁇ l/well), containing 10 ng/ml TGF- ⁇ 1 and 0, 0.01 ⁇ g/ml, 0.1 ⁇ g/ml, 1 ⁇ g/ml, 10 ⁇ g/ml or 100 ⁇ g/ml PEP005 (three chamber slide wells per PEP005 concentration).

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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
PCT/AU2006/001781 2005-11-25 2006-11-24 Methods for wound healing Ceased WO2007059584A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
AU2006317523A AU2006317523A1 (en) 2005-11-25 2006-11-24 Methods for wound healing
EP06817537A EP1965818A4 (en) 2005-11-25 2006-11-24 WOUND HEALING PROCESS
NZ568168A NZ568168A (en) 2005-11-25 2006-11-24 Methods for wound healing using ingenol compounds
BRPI0618926-1A BRPI0618926A2 (pt) 2005-11-25 2006-11-24 uso de um composto de ingenol ou um sal farmaceuticamente aceitável do mesmo
JP2008541550A JP2009517345A (ja) 2005-11-25 2006-11-24 創傷治癒の方法
US12/094,713 US20090215884A1 (en) 2005-11-25 2006-11-24 Method for wound healing
CA002629899A CA2629899A1 (en) 2005-11-25 2006-11-24 Methods for wound healing
US15/131,851 US20160317486A1 (en) 2005-11-25 2016-04-18 Method for wound healing

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AU2005906601A AU2005906601A0 (en) 2005-11-25 Therapeutic methods and compositions
AU2005906601 2005-11-25

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/094,713 A-371-Of-International US20090215884A1 (en) 2005-11-25 2006-11-24 Method for wound healing
US15/131,851 Continuation US20160317486A1 (en) 2005-11-25 2016-04-18 Method for wound healing

Publications (1)

Publication Number Publication Date
WO2007059584A1 true WO2007059584A1 (en) 2007-05-31

Family

ID=38066849

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/AU2006/001781 Ceased WO2007059584A1 (en) 2005-11-25 2006-11-24 Methods for wound healing

Country Status (9)

Country Link
US (2) US20090215884A1 (https=)
EP (1) EP1965818A4 (https=)
JP (1) JP2009517345A (https=)
KR (1) KR20080077625A (https=)
CN (1) CN101360506A (https=)
BR (1) BRPI0618926A2 (https=)
CA (1) CA2629899A1 (https=)
NZ (1) NZ568168A (https=)
WO (1) WO2007059584A1 (https=)

Cited By (10)

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WO2010091472A1 (en) * 2009-02-13 2010-08-19 Peplin Research Pty Ltd Skin treatment
WO2011128780A1 (en) 2010-04-16 2011-10-20 Leo Pharma A/S Crystalline ingenol mebutate
US8106092B2 (en) 2004-12-13 2012-01-31 Leo Laboratories Limited Treatment of solid cancers
WO2012080466A2 (en) 2010-12-17 2012-06-21 Leo Pharma A/S Ingenols for treating seborrheic keratosis
WO2012085189A1 (en) 2010-12-22 2012-06-28 Leo Pharma A/S Ingenol-3-acylates i
WO2012083954A1 (en) 2010-12-22 2012-06-28 Leo Pharma A/S 3-acyl-ingenols ii
WO2012175742A2 (en) 2011-06-24 2012-12-27 Aqua Bio Technology Asa Methods for the production of a cosmetic composition comprising leukolectin and uses thereof
WO2012176015A1 (en) * 2011-06-24 2012-12-27 Leo Pharma A/S Methods for treating uv-damaged skin and scc tumors and for removing tattoos with topical ingenol mebutate
US9314458B2 (en) 2000-06-07 2016-04-19 Leo Laboratories Limited Topical use of ingenol-3-angelate or a salt thereof to treat skin cancer
US20190192636A1 (en) * 2016-03-18 2019-06-27 Intrexon Corporation Compositions and methods for treatment of type viii collagen deficiencies

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JP5291369B2 (ja) * 2008-03-31 2013-09-18 株式会社ナリス化粧品 ケラチノサイト増殖促進剤
US8273387B2 (en) 2009-08-26 2012-09-25 Mary Kay Inc. Topical skin formulations comprising plant extracts
WO2012005876A2 (en) * 2010-06-30 2012-01-12 Avon Products, Inc. Compositions and methods for stimulating magp-1 to improve the appearance of skin
RU2572549C2 (ru) * 2010-12-22 2016-01-20 Лео Лэборетериз Лимитед Ингенол-3-ацилаты iii и ингенол-3-карбаматы
EP2790670A1 (en) * 2011-12-12 2014-10-22 Leo Laboratories Limited Gel compositions
US20130251782A1 (en) * 2012-03-22 2013-09-26 Leo Laboratories Limited Topical application of ingenol mebutate with occlusion
CA2875461A1 (en) * 2012-06-26 2014-01-03 Xifu Liang 3-o-heteroaryl-ingenol
KR20150027831A (ko) * 2012-07-06 2015-03-12 레오 파마 에이/에스 피부에 활성 성분을 전달하기 위한 막-형성 중합체를 포함하는 국소 조성물
US9962364B2 (en) 2012-12-26 2018-05-08 A-Z Ltd. Wound healing accelerator
US20150366789A1 (en) * 2013-03-13 2015-12-24 Avon Place, Inc. Glochidium wallichianum extracts and methods of use
CN105055448A (zh) * 2015-05-25 2015-11-18 中国人民解放军第三军医大学第一附属医院 铜离子制剂在制备促进皮肤角质形成细胞增殖药物或敷料中的用途
CN106619600B (zh) * 2016-03-28 2019-10-18 中国科学院遗传与发育生物学研究所 巨大戟醇及其衍生物在增强溶酶体生成中的应用
CN115677520B (zh) * 2022-11-18 2024-04-02 扬州大学 一种二萜化合物及其制备方法和应用

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US20160317486A1 (en) 2016-11-03
EP1965818A4 (en) 2010-02-17
US20090215884A1 (en) 2009-08-27
CN101360506A (zh) 2009-02-04
CA2629899A1 (en) 2007-05-31
NZ568168A (en) 2012-06-29
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