EP0724425A1 - Nouvelle utilisation de prostaglandines - Google Patents

Nouvelle utilisation de prostaglandines

Info

Publication number
EP0724425A1
EP0724425A1 EP94931257A EP94931257A EP0724425A1 EP 0724425 A1 EP0724425 A1 EP 0724425A1 EP 94931257 A EP94931257 A EP 94931257A EP 94931257 A EP94931257 A EP 94931257A EP 0724425 A1 EP0724425 A1 EP 0724425A1
Authority
EP
European Patent Office
Prior art keywords
prostaglandin
prostaglandins
eye
skin
hair
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.)
Withdrawn
Application number
EP94931257A
Other languages
German (de)
English (en)
Inventor
Johan Stjernschantz
Bahram Resul
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.)
Pfizer Health AB
Original Assignee
Pharmacia and Upjohn AB
Pharmacia AB
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 Pharmacia and Upjohn AB, Pharmacia AB filed Critical Pharmacia and Upjohn AB
Publication of EP0724425A1 publication Critical patent/EP0724425A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin
    • 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
    • A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes

Definitions

  • the present invention is related to the use of prostaglandins and active derivatives or analogues thereof for increasing pigmentation of tissue, for instance eye, skin and hair of animals, including man.
  • the invention also relates to pharmaceutical or cosmetic compositions for said use, as well as the preparation thereof.
  • the colour of the eye, skin and hair is determined by the amount of melanin in the cells of these structures.
  • the colour is determined by the amount of melanin in the melanocytes of the iris.
  • the melanocytes of the iris contain large amounts of melanin whereas in persons with blue eyes the melanocytes of the iris contain only little melanin.
  • the short wave length blue light is not absorbed making the eye colour appear as blue.
  • the light is absorbed by the melanin in the melanocytes making the colour appear as brown.
  • persons with light brown (hazel) or green-brown irises the melanocytes contain more melanin than in persons with blue eyes but less than in persons with brown eyes.
  • the colour of the hair is determined by the melanocytes located at the dermal papillas.
  • the melanin from these cells is transferred to the cells of the hair matrix and cortex which subsequently keratinize and form the hair.
  • the growth of eyelashes is similar to that of the hair with melanocytes in close vicinity to the eyelash follicle. Consequently, stimulating these melanocytes to produce more melanin will make the eyelashes darker.
  • a-MSH alpha-melanocyte stimulating hormone
  • steroid hormones are known to affect pigmentation of the skin.
  • the UV light stimulates directly or indirectly the melanocytes in the skin to produce more melanin which is transferred to the adjacent keratinocytes.
  • the factors determining the eye colour or hair colour are not known and UV light e.g. has no or negligible effect on the eye colour.
  • Melanin is a large polymer packed in small granules called melanosomes. There are several kinds of melanin. The most common brown-black melanin is called eumelanin. Another melanin containing cysteine is pheomelanin. Typically the colour of pheomelanin is yellow-red. Individuals with reddish hair have pheomelanin. A third kind of melanin is oximelanin which is black.
  • autacoids more specifically prostaglandins and prostaglandin derivatives and analogues can be used for increasing pigmentation of body tissues, like skin and iris of the eye, or modified body tissues like hair and eyelashes, when applied topically on the tissue for long periods of time. So can the colour of the eye be altered due to pigmentation of the iris by application of a prostaglandin.
  • Such experiments have been performed in monkeys and the results have recently been verified in man in clinical trials with a prostaglandin analogue.
  • man prostaglandins can alter the colour of the eyelashes. Since the eyelashes are analogous with hair a well-based prediction is that similar treatment of the tissue from which hair is developed will result in a corresponding modification of the colour.
  • Prostaglandins are a group of components derived from unsaturated 20-carbon fatty acids produced normally by the body. Virtually all tissues of the body produce prostaglandins and other eicosanoids. The prostaglandins have a variety of important physiologic functions and are classified as autacoids, autacoid meaning local hormone. Typically local hormones such as prostaglandins have a consonant effect in the tissue on many different physiological events.
  • the prostaglandins consist of a cyclopentane ring, denoted "X" in the above formula, and two side chains, the upper one containing 7 carbon atoms being called the alpha chain and the lower one containing 8 carbon atoms being called the omega chain.
  • the end of the alpha chain is normally a carboxylic acid moiety.
  • the side chains can contain 1 to 3 double bonds, most frequently 2, the double bonds being situated between carbon atoms 5 and 6 on the alpha chain as well as 13 and 14 on the omega chain.
  • the double bond on the alpha chain exhibits cis-configuration, whereas the double bond on the omega chain exhibits trans- configuration.
  • Essential for biological activity is furthermore the substituent group on carbon 15 in the omega chain. In naturally occurring prostaglandins this substituent is hydroxyl.
  • the configuration and functionalities of the cyclopentane ring (X) is important for selectivity to different prostaglandin receptors and the various configurations are depicted below:
  • prostaglandins are given suffixes A, B, C, D, E, F or J depending on the functionalities of the five membered ring, that is the configuration and substituents of the cyclopentane ring.
  • prostaglandins A, B and C probably are not naturally occurring and represent artificial prostaglandins. Nevertheless they exert considerable biologic activity.
  • the carboxylic acid moiety on the omega chain can be esterified, for instance with alkyl groups containing 1-10 carbons, especially 1-6 carbons e.g.
  • esterified prodrugs of prostaglandins have been described in several patents and patent applications (see for instance EP 093380, EP 0364417 and WO92/02496) .
  • other derivatives such as salts, e.g. the sodium salt, may also be used.
  • Such conditions comprise e.g.
  • Vitiligo a typical disease entity in the skin with hypopigmentation. Vitiligo can occur in many different parts of the body and is perceived as a cosmetic and psychological problem.
  • the invention can alternatively be defined as providing a method for stimulating melanocytes to produce increased amounts of melanin-type substances in animals including man.
  • the prostaglandins are applied repeatedly for a sustained period of time topically on the part of the body to be treated, for instance the eye, skin or scalp.
  • the active component, the prostaglandin can be administered by means of aqueous solutions or oil solutions as well as in liniments, creams, ointments, shampoos or in patches, depending on the part of the body to be treated.
  • the formulations thus have to be adapted to the specific physiological requirements of the organ or tissue to be treated.
  • the solubility and/or stability of the prostaglandin compound may be increased by adding substances forming a complex with the prostaglandin, for instance cyclodextrin-type substances or other compounds known to form complexes, such as inclusion complexes, with hydrophobic compounds.
  • the prostaglandins as well as their derivatives and analogues, including esters and salts can be formulated in aqueous solutions, creams, ointments or oils exhibiting physiologically acceptable osmolarity by addition of pharmacologically acceptable buffers and salts.
  • Such formulations may or may not, depending on the dispenser, contain preservatives such as benzalkonium chloride, chlorhexidine, chlorobutanol, parahydroxybenzoic acids and phenylmercuric salts such as nitrate, chloride, acetate, and borate, or antioxidants, as well as additives like EDTA, sorbitol, boric acid etc. as additives.
  • aqueous solutions may contain viscosity increasing agents such as polysaccharides, e.g. methylcellulose, mucopolysaccharides, e.g. hyaluronic acid and chondroitin sulfate, or polyalcoholes, e.g. polyvinylalcohol.
  • viscosity increasing agents such as polysaccharides, e.g. methylcellulose, mucopolysaccharides, e.g. hyaluronic acid and chondroitin sulfate, or polyalcoholes, e.g. polyvinylalcohol.
  • Various slow releasing gels and matrices may also be employed as well as soluble and insoluble ocular inserts, for instance based on substances forming in-situ gels.
  • various amounts of the drug and different dose regimens may be employed.
  • the daily amount of prostaglandin for treatment of the eye might be 0.1-1000 ⁇ g/eye, particularly 1-100 ⁇ g/eye.
  • the prostaglandins may be administered once or several times daily.
  • the prostaglandin component can advantageously be formulated using ointments, creams, liniments or patches as carrier.
  • these formulations may or may not contain preservatives depending on the dispenser.
  • preservatives comprise as mentioned above e.g. methyl-, propyl- or butyl-parahydroxybenzoic acid, betain, chlorhexidine, benzalkonium chloride, and alike.
  • Various matrices for slow release delivery may also be used.
  • the dose to be applied on the scalp is in the range of 0.0001-100 mg/day, esp. 0.001-100 mg/day, depending on the prostaglandin and the formulation.
  • the dose is 0.001-10 mg/day and especially 0.01-10 mg/day.
  • a dose of 0.0001-10 mg/square decimetre/day like 0.001-1 and esp. 0.01-1 mg/square decimetre/day is employed.
  • the prostaglandin may be administered once or several times daily with or without antioxidants.
  • prostaglandins may be employed to achieve the therapeutic effect on pigmentation in the types of tissues discussed above, e.g. the eye, skin and hair. Particularly prostaglandins of the A, F and E types have been found efficacious. To minimize side effects such as irritation and redness of the eye and skin it may be suitable to use prostaglandin derivatives or analogues which have been found to exert less side effects such as phenyl- and other ring-substituted prostaglandin derivatives described e.g. in PCT patent publication no: W090/02553.
  • Prostaglandins exhibiting high pharmacological activity and no or only very small side effects such as 17-phenyl-18, 19,20-trinor-PGF2 and its carboxylic acid esters may be particularly useful if large areas e.g. of the skin are to be treated.
  • Other prostaglandin analogues exhibiting good therapeutic index may also be used.
  • the prostaglandins since hair growth is slow, the prostaglandins have to be used for sustained periods of time, typically half a year to one year, and if the coloration of the skin or hair is to be preserved the prostaglandin has to be used chronically. It is also possible to use the formulation containing prostaglandins during long term treatment intermittently, e.g. once or twice a week, once every second week or e.g. continuously for a month followed by a month without treatment etc, depending on the potency of the particular prostaglandin.
  • the prostaglandin formulation has to be administered regularly at least for 3 months or longer.
  • the prostaglandin can be administered less frequently to maintain the new state of pigmentation e.g. once a week or once a month or possible even with longer intervals or alternatively with intermittent periods of frequent treatment, e.g. once daily for a month which is followed by a period of 3-12 months of no treatment, followed again by treatment once daily for one month, etc.
  • intermittent periods of frequent treatment e.g. once daily for a month which is followed by a period of 3-12 months of no treatment, followed again by treatment once daily for one month, etc.
  • the colour change in the iris induced by prostaglandin treatment is permanent and no continuing or intermittent treatment is necessary.
  • the invention is exemplified with the following non- limiting experiments and clinical data: Synthesis and formulation of prostaglandin derivatives.
  • PGE2 PGE2 obtained from Chinoin
  • acetonitrile 10 mL
  • ethyl diisopropyl amine 161 mg, 1.3mmoL
  • isopropyl iodide 380 mg, 2.3 mmoL
  • the reaction mixture was warmed to 60-65° C for 2-3 hours (TLC monitoring) .
  • the solution was diluted with diethyl ether (30 mL) and washed with water (20 mL) . The water layer was extracted with diethyl ether (30 mL) .
  • Cynomolgus monkeys were used. The monkeys were treated topically once daily for 4-12 months with either of the following prostaglandins:
  • the contralateral eye received the vehicle only and served as a control.
  • the frequency of increased iridial pigmentation is shown in Table I.
  • the increase in iridial pigmentation was mostly classified as mild to moderate but in all groups some animals exhibited marked pigmentation.
  • PGE2 ⁇ isopropylester, PGF 2a -isopropylester as well as 13, 14-dihydro-17-phenyl-18, 19,20-trinor-PGF 2a - isopropylester all increased iridial pigmentation in an animal model closely reminiscent of the human eye.
  • Table I Frequency of increased iridial pigmentation in monkeys after treatment with prostaglandin for 4-12 months .
  • Table II Occurrence of increased pigmentation of the iris during treatment with 13, 14-dihydro-17-phenyl- 18, 19,20-trinor-PGF 2a -isopropylester in patients with elevated intraocular pressure.
  • prostaglandins The implication of the finding with increased pigmentation of the eye-lashes is that hair in general can be made darker with prostaglandins.
  • the hair of the scalp in principle can be treated in the same way with prostaglandins to become darker. Since the hair has a growth rate of approximately 0.5-1 cm/month treatment to convert the colour of the hair will take 6-12 months or longer and to maintain the colour the treatment must continue at regular intervals or intermittently.
  • This indication of prostaglandins may be employed e.g. in individuals suffering from grey or white hair.
  • a tanning of the skin can be achieved analogously.
  • Such tanning may be desirable from a simple cosmetic point of view but may also be important from a therapeutical point of view in the treatment of certain pathological conditions in the skin such as hypopigmentation e.g. vitiligo.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Ophthalmology & Optometry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)

Abstract

Procédé de production d'une composition renfermant des prostaglandines, ou des dérivés ou analogues de prostaglandines, et servant à augmenter la pigmentation des tissus ou des tissus modifiés, par exemple les cheveux. On a mis en évidence que les dérivés et analogues de prostaglandine F2a et de prostaglandine E2 notamment sont utilisables à cette fin.
EP94931257A 1993-10-20 1994-10-19 Nouvelle utilisation de prostaglandines Withdrawn EP0724425A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
SE9303444 1993-10-20
SE9303444A SE9303444D0 (sv) 1993-10-20 1993-10-20 New use of prostaglandins
PCT/SE1994/000985 WO1995011003A1 (fr) 1993-10-20 1994-10-19 Nouvelle utilisation de prostaglandines

Publications (1)

Publication Number Publication Date
EP0724425A1 true EP0724425A1 (fr) 1996-08-07

Family

ID=20391475

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94931257A Withdrawn EP0724425A1 (fr) 1993-10-20 1994-10-19 Nouvelle utilisation de prostaglandines

Country Status (6)

Country Link
EP (1) EP0724425A1 (fr)
JP (1) JPH09504021A (fr)
AU (1) AU8008694A (fr)
CA (1) CA2174655A1 (fr)
SE (1) SE9303444D0 (fr)
WO (1) WO1995011003A1 (fr)

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WO1998000100A1 (fr) * 1996-07-03 1998-01-08 The Board Of Regents Of The University Of Oklahoma Augmentation de la pigmentation de la peau au moyen des prostaglandines
DE69823852T2 (de) * 1997-02-04 2005-05-19 Johnstone, Murray A., Seattle Verfahren zur förderung des haarwuchses und entwicklung des haarsystems
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US20020172693A1 (en) * 2000-03-31 2002-11-21 Delong Michell Anthony Compositions and methods for treating hair loss using non-naturally occurring prostaglandins
US20020013294A1 (en) 2000-03-31 2002-01-31 Delong Mitchell Anthony Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives
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FR2812192B1 (fr) * 2000-07-28 2003-01-31 Oreal Utilisation d'antagonistes de recepteur des prostaglandines ep-3 comme agent cosmetique permettant d'attenuer, de diminuer ou d'arreter la chute des cheveux et des poils
KR100437873B1 (ko) * 2001-05-08 2004-06-26 연성정밀화학(주) 프로스타글란딘 유도체의 제조방법 및 그의 입체특이적출발물질
US8758733B2 (en) 2002-02-04 2014-06-24 Allergan, Inc. Topical treatment for chemotherapy induced eyelash loss or hypotrichosis using prostamide F2 alpha agonists
US9216183B2 (en) 2002-02-04 2015-12-22 Allergan, Inc. Topical treatment for chemotherapy induced eyelash loss or hypotrichosis using prostamide F2 alpha agonists
US7351404B2 (en) 2002-02-04 2008-04-01 Allergan, Inc. Method of enhancing hair growth
JP4584908B2 (ja) 2003-02-12 2010-11-24 ロレアル 皮膚または皮膚付属物の色素沈着を刺激するための１５−ヒドロキシプロスタグランジンデヒドロゲナーゼの阻害剤の使用
US7326717B2 (en) 2003-05-06 2008-02-05 L'oreal Pyrimidine n-oxide compounds for stimulating the growth of keratin fibers and/or reducing loss thereof
TWI495471B (zh) 2003-08-12 2015-08-11 R Tech Ueno Ltd 促進毛髮生長之組成物及方法
FR2907682B1 (fr) 2006-10-26 2012-12-07 Vincience Composition cosmetique et/ou pharmaceutique comprenant comme principe actif au moins un peptide et utilisation de ce peptide.
FR2920309B1 (fr) 2007-08-28 2010-05-28 Galderma Res & Dev Utilisation de travoprost pour traiter la chute des cheveux
RU2504380C2 (ru) * 2008-09-04 2014-01-20 Сантен Фармасьютикал Ко., Лтд. АГЕНТ, СПОСОБСТВУЮЩИЙ РОСТУ ВОЛОС, СОДЕРЖАЩИЙ В КАЧЕСТВЕ АКТИВНОГО ИНГРЕДИЕНТА ПРОИЗВОДНОЕ 15,15-ДИФТОРПРОСТАГЛАНДИНА F2α
WO2010064203A1 (fr) 2008-12-02 2010-06-10 L'oreal Combinaison de glutathion réduit et d'acides aminés pour améliorer la qualité des cheveux de femmes
US20110293549A1 (en) 2009-02-03 2011-12-01 Athena Cosmetics, Inc. Composition, method and kit for enhancing hair
FR2949052B1 (fr) 2009-08-13 2015-03-27 Oreal Procede de traitement cosmetique du cuir chevelu.
FR2951938B1 (fr) 2009-10-30 2012-01-06 Oreal Utilisation d'un extrait de punica granatum pour lutter contre la canitie
NZ628266A (en) 2009-11-09 2016-02-26 Allergan Inc Compositions and methods for stimulating hair growth
US9149484B2 (en) 2009-11-09 2015-10-06 Allergan, Inc. Compositions and methods for stimulating hair growth
US8859616B2 (en) 2011-01-21 2014-10-14 Allergan, Inc. Compounds and methods for enhancing hair growth
FR2978659B1 (fr) 2011-08-05 2014-01-10 Oreal Utilisation de composes cannabinoides pour stimuler la melanogenese
US9790233B2 (en) 2012-04-16 2017-10-17 Case Western Reserve University Compositions and methods of modulating 15-PGDH activity
FR2999932B1 (fr) 2012-12-21 2020-01-31 Société des Produits Nestlé S.A. Utilisation de microorganismes probiotiques comme agent favorisant la synthese de melanine
FR2999931A1 (fr) 2012-12-21 2014-06-27 Oreal Utilisation de microorganismes probiotiques comme agent favorisant la synthese de melanine
EP3057973B1 (fr) 2013-10-15 2019-09-04 Case Western Reserve University Compositions comportant un inhibiteur de 15-pdgh pour la cicatrisation de plaies
AU2016229918B2 (en) 2015-03-08 2020-10-29 Case Western Reserve University Inhibitors of short-chain dehydrogenase activity for treating fibrosis
US11690847B2 (en) 2016-11-30 2023-07-04 Case Western Reserve University Combinations of 15-PGDH inhibitors with corticosteroids and/or TNF inhibitors and uses thereof
WO2018145080A1 (fr) 2017-02-06 2018-08-09 Case Western Reserve University Compositions et procédés de modulation de l'activité de la déshydrogénase à chaîne courte
CR20210328A (es) 2018-11-21 2021-12-02 Univ Case Western Reserve Composiciones y métodos para modular la actividad de deshidrogenasas de cadena corta
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Also Published As

Publication number Publication date
AU8008694A (en) 1995-05-08
WO1995011003A1 (fr) 1995-04-27
CA2174655A1 (fr) 1995-04-27
JPH09504021A (ja) 1997-04-22
SE9303444D0 (sv) 1993-10-20

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