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WO2006084312A1 - Methode de stimulation de la croissance des cheveux - Google Patents

Methode de stimulation de la croissance des cheveux Download PDF

Info

Publication number
WO2006084312A1
WO2006084312A1 PCT/AU2006/000155 AU2006000155W WO2006084312A1 WO 2006084312 A1 WO2006084312 A1 WO 2006084312A1 AU 2006000155 W AU2006000155 W AU 2006000155W WO 2006084312 A1 WO2006084312 A1 WO 2006084312A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
esters
testosterone
group
previous
Prior art date
Application number
PCT/AU2006/000155
Other languages
English (en)
Inventor
Andrew Jonathan Humberstone
Karen Lee Gard'ner
Original Assignee
Acrux Dds 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 AU2005900598A external-priority patent/AU2005900598A0/en
Application filed by Acrux Dds Pty Ltd filed Critical Acrux Dds Pty Ltd
Publication of WO2006084312A1 publication Critical patent/WO2006084312A1/fr

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
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
    • 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
    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia

Definitions

  • the present invention relates to a method of promoting hair growth and to composition for promotion of hair growth.
  • the invention also relates to the use of certain agents in the preparation of a composition for the treatment or prevention of hair loss.
  • the invention is useful in the treatment or prevention of hair loss and also in promotion of new hair growth.
  • Alopecia hair loss is understood to result from the conversion of systemic testosterone to dihydrotestosterone (DHT) in the hair root ball and stem cell regions of the skin.
  • DHT dihydrotestosterone
  • male pattern baldness represents an androgen-mediated miniaturisation of terminal hair follicles without actual loss of the follicles.
  • the progression of male pattern baldness is associated with a local accumulation of DHT from testosterone.
  • DHT is also associated with female pattern hair loss. Before menopause various forms of estrogen block testosterone resulting in low levels of DHT in the skin. After menopause however, estrogen levels decline and more testosterone is bioavailable to be converted to DHT resulting in finer hair in a proportion of women. Minoxidil in a 2% concentration has been found to help their growth in about 20% of women.
  • 5-Alpha reductase inhibitors such as finasteride are currently prescribed for treatment of hair loss in men and women.
  • Much of the prior art concerned with preventing or treating hair loss therefore focused on blocking the pathway which controls the capacity of the skin to convert testosterone to dihydrotestosterone in individuals at risk. This path is regulated by 5-alpha reductase.
  • US Patent 6,420352 adopts a strategy of blocking the binding of testosterone or DHT to the cell surface. Their use is said to provide the key shortfall that efficacy is compromised by blocking of androgen feedback inhibition of gonadotrophin secretion which in turn increases secretion of testosterone.
  • a high level of systemic testosterone is said to overcome the action of the anti- androgen.
  • a method of promoting hair growth comprising topically applying to the area of skin in which hair growth is to be promoted a composition comprising an androgen selected from the group consisting of testosterone and pharmaceutically acceptable esters thereof and a carrier comprising a volatile solvent.
  • composition of the invention will preferably further comprise a volatile solvent such as selected from the group consisting of lower alkanols such as ethanol, isopropanol and glycol.
  • a volatile solvent such as selected from the group consisting of lower alkanols such as ethanol, isopropanol and glycol.
  • the composition of the invention is preferably in the form of a topical spray composition.
  • the invention provides the use of testosterone or an ester of testosterone in preparation of a transdermal composition for promotion of hair growth.
  • a composition for promoting hair growth comprising at least one androgen selected from the group consisting of testosterone and esters thereof and at least one 5-alpha reductase inhibitor.
  • the composition will generally comprise a carrier which preferably includes a volatile solvent and penetration enhancer.
  • the composition used in the present invention for promoting hair growth contains at least one androgen selected from testosterone and esters of testosterone. It was surprising to find that testosterone was effective in prevention or treatment of hair loss as it was previously believed that the blocking of conversion of testosterone to dihydrotestosterone was important to understanding the activity of previously used 5-alph reductase inhibitors. We have found that locally applied testosterone, which may have been expected to increase the formation of DHT and exacerbate the problem of hair loss actually promotes hair growth thereby treating or preventing hair loss.
  • Suitable esters of testosterone include lower alkyl esters of testosterone such as the isopropyl ester.
  • the 5-alpha reductase inhibitors used in the process of the invention may inhibit the activity of type one or type two 5-alpha reductase.
  • the preferred 5-alpha reductase inhibitors include finasteride, gamma linolenic acid, alpha linolenic acid, linolenic acid, azelaic acid, vitamin B6, zinc sulfate, permixon, flutamide and beta sitosterol.
  • compositions of the invention may additionally comprise other hair growth promoters such as potassium channel openers.
  • potassium channel openers include minoxidil, chromicalyn, pinacidil and the compounds selected from the classes of s-triazine, thiane-1 -oxide, benzo pyran and pyhdino pyran derivatives or pharmaceutically acceptable salts thereof.
  • the ratio of the androgen component selected from testosterone and esters thereof to the 5-alpha reductase inhibitors in the present invention is preferably in the range of from 5:1 to 100:1 and preferably from 10:1 to 50:1.
  • the androgen components selected from testosterone and esters thereof may be present in the composition in a range of concentrations depending on the mode and dose of composition to be applied. Typically the composition will comprise in the range of from 0.1 - 10 percent by weight of the total androgen component.
  • the composition of the invention will typically include a volatile solvent.
  • the preferred volatile solvents are selected from the group consisting of ethanol, isopropanol, ethylene glycol and propylene glycol. Typically the volatile solvent will constitute from 50 to 99.9 percent by weight of the total composition.
  • composition of the invention will preferably include a penetration enhancer.
  • a penetration enhancer particularly in combination with the androgen provides good activity at the site of application.
  • a range of penetration enhancers may be used including one or more selected from the group consisting of fatty acids, fatty acid esters, fatty alcohols, glycols and glycol esters, 1 ,3-dioxolanes and 1 ,3-dioxanes, macrocyclic ketones containing at least 12 carbon atoms, oxazolidinones and oxazolidinone derivatives, alkyl-2-(N,N-disubstituted amino)-alkanoate esters, (N, N- disubstituted amino)-alkanol alkanoates, sunscreen esters and mixtures thereof.
  • the dermal penetration enhancer is selected from the list including oleic acid, oleyl alcohol, cyclopentadecanone (CPE-128TM), sorbitan monooleate, glycerol monooleate, propylene glycol monolaurate, polyethylene glycol monolaurate, 2-n-nonyl 1 ,3-dioxolane (SEPATM), dodecyl 2-(N, N- dimethylamino)-propionate (DDAIP) or its salt derivatives, 2-ethylhexyl 2- ethylhexanoate, isopropyl myhstate, dimethyl isosorbide, 4-decyloxazolidinon-2- one (SR-38TM, TCPI, Inc.), 3-methyl-4-dycyloxazolidinon-2-one, octyl dimethyl- para-aminobenzoate, octyl para-methoxycinnamate, octyl sal
  • fatty acid esters including esters formed between C 6 to Ci 8 fatty acids and alcohols such as Ci to C 6 alcohols and C 2 to C 6 polyols.
  • the esters may be mono esters, diesters of polyols such as the caprylic acid diesters of diols such as propylene glycol.
  • the most preferred penetration enhancers are sunscreen esters such as the compounds disclosed in our US Patent No. 6,229,900 the contents of which are herein incorporated by reference. These preferred sunscreen esters are generally compounds of Formula I:
  • R 1 is hydrogen, lower alcohol, lower alkoxy, halide, hydroxy or NR 3 R 4 ;
  • R 2 is a C 8 to Ci8 alkyl
  • R 3 and R 4 are each independently hydrogen, lower alkyl or R 3 and R 4 together with the nitrogen atom to which they are attached form a 5- or 6- membered heterocyclic ring; n is 0 or 1 , q is 1 or 2, and preferably when n is 0 and R1 is NR 3 R 4 , the NR 3 N 4 is para- substitued.
  • Particularly preferred penetration enhancers are octyl dimethyl-para- aminobenzoate, octyl para-methoxycinnamate, octyl salicylate and mixtures thereof
  • compositions of the invention may be applied to the region of skin in which hair loss is to be prevented or treated in a range of forms.
  • suitable forms include lotions, gels, pastes, aerosols and the like.
  • the composition may be applied in an occlusive or non-occlusive manner.
  • Methods of occlusive application include application using a patch which may be used to cover over a topically applied composition or within which the composition is present as a reservoir contained within the patch. It is preferred however that the composition is applied in a non-occlusive manner and in the most preferred embodiment the composition is applied as a spray.
  • the composition is applied as a spray which is preferably formulated to dry on the skin within three minutes of application.
  • the composition is driven into the skin and the testosterone (and preferably also 5-alpha reductase inhibitor) form a reservoir in the skin which we have found is particularly active in enhancing the growth of hair.
  • Drying time may be determined by in vitro or in vivo tests. A suitable in vitro test involves placing a 10 ⁇ l_ sample on a clean glass slide at room temperature (approx 20 °C) and using a four decimal place analytical balance to measure the time take for the vehicle to stop evaporating. The resulting drying times from three repetitions of the test may be averaged. For in vivo drying time measurement 10 ⁇ L is applied to volar fore arms (32 °C) of three subjects and the drying time measured by touch and visual verification (no visible surface vehicle or shine).
  • the drug system used in the composition of the invention may further comprise a pharmaceutical compounding agent, co-solvent, surfactant, emulsifier, antioxidant, preservative, stabiliser, diluent or a mixture of two or more thereof.
  • additional components will preferably be compatible with the ability of the composition to become touch-dry within three minutes after application.
  • the drug delivery system of the present invention may be applied to the skin by means of a spray which may for example be delivered from a pressurised aerosol container or pump-pack, brush, swab, or other applicator.
  • the applicator provides either a fixed or variable metered dose application such as a metered dose aerosol, a stored-energy metered dose pump or a manual metered dose pump.
  • the application is most preferably performed by means of a topical metered dose aerosol or spray pack combined with an actuator nozzle shroud which together accurately control the amount and/or uniformity of the dose applied.
  • One function of the shroud is to keep the nozzle at a pre-determined height above, and perpendicular to, the skin or membrane to which the drug delivery system is being applied. This function may also be achieved by means of a spacer-bar or the like.
  • Another function of the shroud is to enclose the area above the skin or membrane in order to prevent or limit bounce-back and/or loss of the drug delivery system to the surrounding environment.
  • the area of application defined by the shroud is substantially circular in shape.
  • composition of the invention may be propelled to form a spray by either pump pack or by the use of propellants such as hydrocarbons, hydro fluorocarbons, nitrogen, nitrous oxide, carbon dioxide or ethers, preferably dimethyl ether.
  • propellants such as hydrocarbons, hydro fluorocarbons, nitrogen, nitrous oxide, carbon dioxide or ethers, preferably dimethyl ether.
  • Hydrocarbon propellants and hydroflurocarbons such as HFC134a are particularly preferred.
  • the non-occlusive, drug delivery system is preferably in a single phase system as this allows less complicated manufacture and ease of dose uniformity where used as propellant may be in an amount of from 1 to 10% and preferably 1 to 5% by weight of the total composition. It may also be necessary to apply a number of dosages on untreated skin to obtain the desired result.
  • Male pattern baldness represents an androgen-mediated miniaturisation of terminal hair follicles without actual loss of the follicles. It is possible that the "super-loading" of testosterone at the site of application may account for the increase in hair growth.
  • a list of the conditions which can be treated using the method of the invention and the compositions of the invention include male pattern baldness, female- pattern baldness, alopecia areata, alopecia totalis.
  • Contributing factors to hair loss include poor diet, poor circulation, acute illness, radiation, chemotherapy, high stress, thyroid imbalance, certain drugs, diabetes, high doses of vitamin A (more than 100,000 IU), sudden weight loss, high fever, iron deficiency, ringworm, some fungal infections, chemicals and hair dyes, vitamin deficiencies, and lack of proper nutrition. Hair loss as a result of these factors may also be treated using the method of the current invention.
  • hair growth refers generally to any growth in number, thickness and/or length of both new and existing hairs.
  • Study Population A total of 261 female patients (35-45 years old) were enrolled into the study.
  • Administration Route Daily application of transdermal spray(s) applied to the abdomen.
  • Treatments A: Testosterone MDTS ® (2 x 90 ⁇ l_ sprays) containing
  • C Testosterone MDTS ® (1 x 56 ⁇ l_ spray) containing 5.0% w/v testosterone and 8.0% w/v octyl salicylate in 95% ethanol applied to the same site daily.
  • D Placebo MDTS ® (1 or 2 x 90 or 56 ⁇ l_ sprays) containing 8.0% w/v octyl salicylate in 95% ethanol to the same site(s) daily.
  • Study Duration 16 weeks (plus a 4-8 week selection period and 4-week follow up period).
  • Component Amount (%w/v)
  • Component Amount (%w/v)
  • compositions such as described in Examples 2 and 3 above may be applied as a spray from a pump-pack or may be delivered from an aerosol container in the presence of a propellant such as P134a or butane (in an amount of about 1 to
  • a plastic-coated glass aerosol container of suitable fill volume such as 1 to 100 ml and preferably about 10 ml fill volume may be fitted with a pharmaceutical grade metered-dose valve of a nominated discharge volume such as 10 to 1000 ⁇ l for the testosterone aerosol.
  • a stainless steel O-ring may lock the valve in place on the aerosol container.
  • the aerosol container may be charged with testerone, non-volatile, dermal penetration enhancer when used, volatile liquid carrier and optionally any other actives such as the 5-alpha reuctase inhibitor, surfactants or additives followed by the propellant according to any suitable process.
  • a pharmaceutical grade spray nozzle and an aerosol shroud may fitted to keep the spray nozzle perpendicular to the skin at a height of about 20 to 100mm and preferably about 50 mm.
  • the aerosol may be used as follows:
  • the applied composition will preferably be formulated to dry on the skin within 3 minutes and more preferably 1 minute.
  • the nozzle shroud envelopes the spray, providing an effective closed system which deposits the active agent into the skin, and such that when the spray hits the surface of the skin it does not undergo any appreciable bounce-back into the atmosphere.
  • a defined dose of active agent and penetration enhancer is forced through a uniform spray nozzle at a constant pressure form a defined height to give a uniform dose per cm 2 .

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (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)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne une méthode de stimulation de la croissance des cheveux comprenant l'application locale, sur la zone de peau au niveau de laquelle la chute de cheveux doit être traitée ou prévenue, d'une préparation comprenant un agent androgène sélectionné au sein du groupe constitué par la testostérone et les esters de qualité pharmaceutique de ce composé, ainsi qu'un vecteur comprenant un solvant volatil. La présente invention concerne également une préparation à usage local destinée à la stimulation de la croissance des cheveux.
PCT/AU2006/000155 2005-02-09 2006-02-09 Methode de stimulation de la croissance des cheveux WO2006084312A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AU2005900598A AU2005900598A0 (en) 2005-02-09 Method of treatment or prevention of hair loss
AU2005900598 2005-02-09

Publications (1)

Publication Number Publication Date
WO2006084312A1 true WO2006084312A1 (fr) 2006-08-17

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/AU2006/000155 WO2006084312A1 (fr) 2005-02-09 2006-02-09 Methode de stimulation de la croissance des cheveux

Country Status (1)

Country Link
WO (1) WO2006084312A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009062682A1 (fr) * 2007-11-13 2009-05-22 Erlacos Gmbh Stéroïdes c-19 à usage cosmétique et autres
WO2011082384A2 (fr) 2009-12-31 2011-07-07 Differential Drug Development Associates, Llc Modulation de la solubilité, de la stabilité, de l'absorption, du métabolisme et du profil pharmacocinétique de médicaments lipophiles par les stérols
US10265328B2 (en) 2007-11-13 2019-04-23 Procima Gmbh C-19 steroids for specific therapeutic uses
WO2019095027A1 (fr) * 2017-11-20 2019-05-23 Carvalho Junior Mario Virgilio De Formulations transdermiques liquides comprenant un ou plusieurs principes actifs dissous dans un unique solvant et excipient qsp, le propylèneglycol
US11617758B2 (en) 2009-12-31 2023-04-04 Marius Pharmaceuticals Llc Emulsion formulations

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2167957A (en) * 1984-12-07 1986-06-11 Yoshiaki Oshima Hair growth stimulating compositions
WO1997029735A1 (fr) * 1996-02-19 1997-08-21 Monash University Promoteurs de penetration dermique et systeme d'administration de medicaments comprenant ces promoteurs
WO1999036067A1 (fr) * 1998-01-20 1999-07-22 The Gillette Company Modulation de la croissance des poils
US20020086873A1 (en) * 2000-07-19 2002-07-04 Knowles W. Roy Hair loss prevention

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2167957A (en) * 1984-12-07 1986-06-11 Yoshiaki Oshima Hair growth stimulating compositions
WO1997029735A1 (fr) * 1996-02-19 1997-08-21 Monash University Promoteurs de penetration dermique et systeme d'administration de medicaments comprenant ces promoteurs
WO1999036067A1 (fr) * 1998-01-20 1999-07-22 The Gillette Company Modulation de la croissance des poils
US20020086873A1 (en) * 2000-07-19 2002-07-04 Knowles W. Roy Hair loss prevention

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BERGER R.A. ET AL.: "Failure of Topical Testosterone in Male-Pattern Alopecia", THE JOURNAL OF THE AMERICAN MEDICAL ASSOCIATION, vol. 204, no. 6, May 1968 (1968-05-01), pages 131 - 132 *
MEIDAN V.M. ET AL.: "Treatments for Androgenic Alopecia and Alopecia Areata. Current Options and Future Prospects", THERAPY IN PRACTICE. DRUGS, vol. 61, no. 1, 2001, pages 53 - 69 *
PAPA C.M. ET AL.: "Stimulation of Hair Growt by Topical Application of Androgen", THE JOURNAL OF THE AMERICAN MEDICAL ASSOCIATION, vol. 191, no. 7, February 1965 (1965-02-01), pages 521 - 525 *
WOOD A.J. ET AL.: "Treatment of Hair Loss", THE NEW ENGLAND J. OF MEDICINE, vol. 341, no. 13, September 1999 (1999-09-01), pages 964 - 973 *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009062682A1 (fr) * 2007-11-13 2009-05-22 Erlacos Gmbh Stéroïdes c-19 à usage cosmétique et autres
US10265328B2 (en) 2007-11-13 2019-04-23 Procima Gmbh C-19 steroids for specific therapeutic uses
US8258123B2 (en) 2007-11-13 2012-09-04 Erlacos Gmbh C-19 steroids for cosmetic and further uses
CN101854908B (zh) * 2007-11-13 2013-03-06 埃拉克斯有限责任公司 用于化妆品和其他应用的c-19甾族化合物
EP2682111A1 (fr) * 2009-12-31 2014-01-08 Differential Drug Development Associates LLC Modulation de la solubilité, la stabilité, l'absorption, le métabolisme et profil pharmacocinétique de médicaments lipophiles par des stérols
EP2519230A4 (fr) * 2009-12-31 2013-07-10 Differential Drug Dev Associates Llc Modulation de la solubilité, de la stabilité, de l'absorption, du métabolisme et du profil pharmacocinétique de médicaments lipophiles par les stérols
JP2013516433A (ja) * 2009-12-31 2013-05-13 ディッフェレンシャル ドラッグ ディベロップメント アソシエイツ，エルエルシー ステロールによる親油性薬剤の溶解性、安定性、吸収性、代謝性、及び薬物動態プロファイルの調節
WO2011082384A2 (fr) 2009-12-31 2011-07-07 Differential Drug Development Associates, Llc Modulation de la solubilité, de la stabilité, de l'absorption, du métabolisme et du profil pharmacocinétique de médicaments lipophiles par les stérols
US10576090B2 (en) 2009-12-31 2020-03-03 Marius Pharmaceuticals Llc Modulation of solubility, stability, absorption, metabolism, and pharmacokinetic profile of lipophilic drugs by sterols
US10576089B2 (en) 2009-12-31 2020-03-03 Marius Pharmaceuticals Llc Modulation of solubility, stability, absorption, metabolism, and pharmacokinetic profile of lipophilic drugs by sterols
US11590146B2 (en) 2009-12-31 2023-02-28 Marius Pharmaceuticals Llc Modulation of solubility, stability, absorption, metabolism, and pharmacokinetic profile of lipophilic drugs by sterols
US11617758B2 (en) 2009-12-31 2023-04-04 Marius Pharmaceuticals Llc Emulsion formulations
US12295961B2 (en) 2009-12-31 2025-05-13 Marius Pharmaceuticals, Inc. Modulation of solubility, stability, absorption, metabolism, and pharmacokinetic profile of lipophilic drugs by sterols
US12357643B2 (en) 2013-03-15 2025-07-15 Marius Pharmaceuticals, Inc. Emulsion formulations
WO2019095027A1 (fr) * 2017-11-20 2019-05-23 Carvalho Junior Mario Virgilio De Formulations transdermiques liquides comprenant un ou plusieurs principes actifs dissous dans un unique solvant et excipient qsp, le propylèneglycol

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