WO2009108147A1 - Dapsone to treat rosascea - Google Patents

Dapsone to treat rosascea Download PDF

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Publication number
WO2009108147A1
WO2009108147A1 PCT/US2008/002549 US2008002549W WO2009108147A1 WO 2009108147 A1 WO2009108147 A1 WO 2009108147A1 US 2008002549 W US2008002549 W US 2008002549W WO 2009108147 A1 WO2009108147 A1 WO 2009108147A1
Authority
WO
WIPO (PCT)
Prior art keywords
dapsone
rosacea
pharmaceutical composition
lesions
papulopustular
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/US2008/002549
Other languages
English (en)
French (fr)
Inventor
John Steven Garrett
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.)
Tolmar Therapeutics Inc
Original Assignee
QLT USA Inc
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 BRPI0822264-9A2A priority Critical patent/BRPI0822264A2/pt
Priority to CA2714674A priority patent/CA2714674A1/en
Priority to PCT/US2008/002549 priority patent/WO2009108147A1/en
Priority to EP08726129.3A priority patent/EP2249765B1/en
Priority to US12/305,413 priority patent/US8586010B2/en
Priority to ES08726129T priority patent/ES2775825T3/es
Application filed by QLT USA Inc filed Critical QLT USA Inc
Priority to JP2010548648A priority patent/JP2011513304A/ja
Priority to AU2008351422A priority patent/AU2008351422A1/en
Publication of WO2009108147A1 publication Critical patent/WO2009108147A1/en
Anticipated expiration legal-status Critical
Priority to US14/063,841 priority patent/US9504661B2/en
Priority to US15/362,099 priority patent/US20170071882A1/en
Ceased legal-status Critical Current

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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
    • A61K31/13—Amines
    • A61K31/145—Amines having sulfur, e.g. thiurams (>N—C(S)—S—C(S)—N< and >N—C(S)—S—S—C(S)—N<), Sulfinylamines (—N=SO), Sulfonylamines (—N=SO2)
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • 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
    • A61K47/02—Inorganic compounds
    • 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
    • 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
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0048—Eye, e.g. artificial tears
    • 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
    • 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
    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Definitions

  • Rosacea is a dermatological syndrome affecting approximately 14 million Americans. It is characterized by flushing of the skin, erythema, inflammatory papules and pustules, edema, telangiectasia, ocular symptoms and rhinophyma. To date, the etiology of rosacea is unknown and there is no clearly recognized cure (Bikowski and Goldman, 2004; Stone and Chodosh, 2004). Four subtypes and one variation of rosacea have been defined.
  • the subtypes are papulopustular rosacea, erythematotelangiectatic rosacea, phymatous rosacea, and ocular rosacea; the rosacea variation is granulomatous rosacea.
  • Some patients may have features of more than one subtype simultaneously, and differences in severity occur within each subtype.
  • the solid microparticulate dapsone reservoir is slowly dissolved in body fluids before it is delivered through the stratum corneum.
  • the dapsone makes up about 0.5% to 10% of the pharmaceutical composition.
  • the microparticulate dapsone can be a crystalline precipitate or an amorphous precipitate.
  • Antioxidants, fragrance, colorants, sunscreens, or combinations thereof may also be present in the topical composition.
  • the dapsone composition comprises about 5% dapsone, about 0.85% carbomer 980, about 25% diethylene glycol monoethyl ether (DGME), about 0.2% methylparaben, about 0.2% sodium hydroxide, and about 68.75% purified water.
  • DGME diethylene glycol monoethyl ether
  • the methods described herein include the treatment of papulopustular rosacea by applying the dapsone composition once or twice daily.
  • the dapsone composition is applied twice daily.
  • the methods additionally include the use of the dapsone pharmaceutical composition alone or in combination with other pharmaceutical compositions for rosacea, including topical and systemic treatments.
  • the treatments are administered simultaneously or sequentially and include oral metronidazole, isotretinoin, tetracyclines including doxycycline, and topical metronidazole, azelaic acid, sodium sulfacetamide/sulfur preparations, and antibiotics including erythromycin, clindamycin and tetracycline.
  • the dapsone and other pharmaceutical are present in the same composition.
  • the dapsone and other pharmaceutical are present in separate compositions.
  • the dapsone pharmaceutical composition is applied topically in the AM and a separate metronidazole composition is applied topically in the PM, or vice versa.
  • the patient has mild to severe papulopustular rosacea.
  • the patient has mild to moderate papulopustular rosacea.
  • the patient has moderate to severe papulopustular rosacea.
  • the rosacea is moderate to severe papulopustular rosacea.
  • treatment results in a mean reduction of at least 13 papulopustular lesions. In some embodiments, treatment results in a mean reduction of at least 43 % of the papulopustular lesions.
  • Figure 10 shows the Investigator's Global Assessment (IGA) success rate over the course of the study in subjects with > 20 lesions.
  • IGA Investigator's Global Assessment
  • the oil phase may include but is not limited to fatty alcohols, acids, or esters such as cetyl palmitate, cetyl alcohol, stearyl alcohol, stearic acid, isopropyl stearate, glycerol stearate, mineral oil, white petrolatum, or other oils alone or in combination.
  • Surfactants may be present in the emulsion to increase kinetic stability.
  • Suitable emulsifiers that may be added to the compositions described herein include, but are not limited to, steareth 20, ceteth 20, sorbitan sesquioleate, sorbitan mono-oleate, propylene glycol stearate, dosium lauroyl sarcosinate, polysorbate 60, or combinations.
  • the term “mild rosacea” refers to papulopustular rosacea that includes mild erythema and several small papules/pustules.
  • the term “moderate rosacea” refers to papulopustular rosacea that includes moderate erythema, with several small or large papules/pustules, and up to two nodules.
  • severe rosacea refers to papulopustular rosacea that includes severe erythema and numerous small and/or large papules/pustules, and up to several nodules.
  • ointment means a semisolid, oil-based topical formulation.
  • examples of ointments include essentially non-aqueous mixtures of petrolatum, lanolin, polyethylene glycol, plant or animal oils, either hydrogenated or otherwise chemically modified.
  • An ointment may also contain a solvent in which an active agent is either fully or partially dissolved.
  • Suitable carrier materials for topical preparations are glycerides, semi-synthetic and synthetic glycerides, hydrogenated oils, liquid waxes, liquid paraffins, liquid fatty alcohols, sterols, polyethylene glycols and cellulose derivatives.
  • the pharmaceutically acceptable carrier includes ethoxydiglycol, also known as diethylene glycol monoethyl ether (DGME).
  • DGME diethylene glycol monoethyl ether
  • the term "suspension” refers to a heterogenous fluid containing solid particles dispersed throughout. The suspended phase or suspensoid is dispersed throughout the liquid in a moderately finely divided state, but not so finely divided as to acquire the stability of a colloidal system. The suspended phase will eventually settle out of the suspension.
  • Papulopustular rosacea is characterized by persistent central facial erythema with transient, central facial papules, pustules or lesions of both types.
  • mild to severe papulopustular rosacea is treated.
  • moderate to severe papulopustular rosacea is treated.
  • Erythematotelangiectatic rosacea is characterized by flushing and persistent central facial erythema, with or without telangiectasia.
  • Phymatous rosacea is characterized by thickening skin, irregular surface nodularities, and enlargement, which may occur on the nose, chin, forehead, cheeks or ears.
  • These media which are preferably organic or organic/aqueous mixtures, may be formulated as eye drops, lotions, gels, ointments, creams, sprays, washes, cleansers, shampoos, roll-on or stick products, micro-emulsions, shake powders, aerosolized sprays or mousse, and bath additives. Additional pharmaceutical carriers will be known to those skilled in the art and this list should not be considered to be limiting.
  • the dapsone of the topical composition may be entirely dissolved in the carrier; partially dissolved and partially microparticulate; or may be present as an emulsion, suspension or colloid. In an entirely dissolved state, dapsone exists completely in solution in the solvent, with no solid dapsone present.
  • a dapsone emulsion includes two immiscible, unblendable substances wherein one substance (the dispersed phase) is dispersed in the other (continuous phase).
  • the dapsone can be part of the dispersed phase or part of the continuous phase of the emulsion.
  • a dapsone suspension is a heterogenous fluid containing solid particles of dapsone dispersed throughout a fluid.
  • a dapsone colloid is a homogenous mixture of dispersed dapsone particles that are distributed evenly and stably throughout the continuous phase.
  • Solvents are grouped into polar (hydrophilic) and non-polar (lipophilic) types. Useful solvents are described in detail below.
  • the solvent of the topical compositions is diethylene glycol monoethyl ether (DGME), also known as ethoxydiglycol.
  • DGME diethylene glycol monoethyl ether
  • OraceaTM (doxycycline, USP capsules), 40 mg. Package Insert. CollaGenex. May 2006. 19. Pelle MT. Rosacea therapy update. Adv Dermatol. 2003; 19: 139-170.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Ophthalmology & Optometry (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Birds (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
PCT/US2008/002549 2008-02-27 2008-02-27 Dapsone to treat rosascea Ceased WO2009108147A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
JP2010548648A JP2011513304A (ja) 2008-02-27 2008-02-27 酒さを処置するためのダプソン
CA2714674A CA2714674A1 (en) 2008-02-27 2008-02-27 Dapsone to treat rosacea
PCT/US2008/002549 WO2009108147A1 (en) 2008-02-27 2008-02-27 Dapsone to treat rosascea
EP08726129.3A EP2249765B1 (en) 2008-02-27 2008-02-27 Dapsone to treat rosacea
US12/305,413 US8586010B2 (en) 2008-02-27 2008-02-27 Dapsone to treat rosascea
BRPI0822264-9A2A BRPI0822264A2 (pt) 2008-02-27 2008-02-27 Dapsona para tratar rosácea
AU2008351422A AU2008351422A1 (en) 2008-02-27 2008-02-27 Dapsone to treat rosascea
ES08726129T ES2775825T3 (es) 2008-02-27 2008-02-27 Dapsona para tratar la rosácea
US14/063,841 US9504661B2 (en) 2008-02-27 2013-10-25 Dapsone to treat rosacea
US15/362,099 US20170071882A1 (en) 2008-02-27 2016-11-28 Dapsone to treat rosacea

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2008/002549 WO2009108147A1 (en) 2008-02-27 2008-02-27 Dapsone to treat rosascea

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/305,413 A-371-Of-International US8586010B2 (en) 2008-02-27 2008-02-27 Dapsone to treat rosascea
US14/063,841 Division US9504661B2 (en) 2008-02-27 2013-10-25 Dapsone to treat rosacea

Publications (1)

Publication Number Publication Date
WO2009108147A1 true WO2009108147A1 (en) 2009-09-03

Family

ID=41016365

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Application Number Title Priority Date Filing Date
PCT/US2008/002549 Ceased WO2009108147A1 (en) 2008-02-27 2008-02-27 Dapsone to treat rosascea

Country Status (8)

Country Link
US (3) US8586010B2 (enExample)
EP (1) EP2249765B1 (enExample)
JP (1) JP2011513304A (enExample)
AU (1) AU2008351422A1 (enExample)
BR (1) BRPI0822264A2 (enExample)
CA (1) CA2714674A1 (enExample)
ES (1) ES2775825T3 (enExample)
WO (1) WO2009108147A1 (enExample)

Cited By (4)

* Cited by examiner, † Cited by third party
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WO2010126349A1 (es) * 2009-04-29 2010-11-04 Universidad Autónoma Metropolitana Formas farmacéuticas solubles de la n, n'-diaminodifenilsulfona para uso óptimo en el tratamiento de diversas enfermedades
EP2364698A4 (en) * 2008-07-25 2011-09-14 Snu R&Db Foundation COMPOSITION AGAINST AGING AND / OR LENGTHENING DURATION, CONTAINING DAPSONE AS ACTIVE INGREDIENT
JP2013522295A (ja) * 2010-03-15 2013-06-13 ヴァージニア コモンウェルス ユニヴァーシティ 気道炎症及び粘液線毛輸送機能異常治療用のエアロゾル化したダプソン
WO2014081674A1 (en) * 2012-11-20 2014-05-30 Allergan, Inc. Topical dapsone and dapsone/adapalene compositions and methods for use thereof

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KR101875705B1 (ko) 2011-12-07 2018-07-06 삼성전자주식회사 디아미노디페닐술폰을 포함하는 근육 소모 관련 질환의 예방 또는 치료용 약학적 조성물
US11039962B2 (en) 2012-04-02 2021-06-22 TurnCare, Inc. Non-invasive pressure-mitigation apparatuses for improving blood flow and associated systems and methods
US20130255699A1 (en) 2012-04-02 2013-10-03 TurnCare, Inc. Patient-orienting alternating pressure decubitus prevention support apparatus
US12178949B2 (en) 2020-10-09 2024-12-31 TurnCare, Inc. Pressure-mitigation apparatuses for improved treatment of immobilized patients and associated systems and methods
US12016812B2 (en) 2020-10-09 2024-06-25 TurnCare, Inc. Pressure-mitigation apparatuses for improved treatment of respiratory illnesses and associated systems and methods
JPWO2022269665A1 (enExample) * 2021-06-21 2022-12-29

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