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WO1992009259A1 - Stimulation de la croissance des cheveux utilisant des agents d'ouverture des vannes a potassium et un agent bloquant les recepteurs d'androgenes - Google Patents

Stimulation de la croissance des cheveux utilisant des agents d'ouverture des vannes a potassium et un agent bloquant les recepteurs d'androgenes Download PDF

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Publication number
WO1992009259A1
WO1992009259A1 PCT/US1991/008306 US9108306W WO9209259A1 WO 1992009259 A1 WO1992009259 A1 WO 1992009259A1 US 9108306 W US9108306 W US 9108306W WO 9209259 A1 WO9209259 A1 WO 9209259A1
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WO
WIPO (PCT)
Prior art keywords
potassium channel
channel opener
pentalenone
hair growth
hexahydro
Prior art date
Application number
PCT/US1991/008306
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English (en)
Inventor
Heinrich Josef Schostarez
Arthur Robert Diani
Original Assignee
The Upjohn Company
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 The Upjohn Company filed Critical The Upjohn Company
Publication of WO1992009259A1 publication Critical patent/WO1992009259A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • 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
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4966—Triazines or their condensed derivatives

Definitions

  • the present invention relates to improved methods and compositions for promoting hair growth by the concomitant administration of a potassium channel opener such as minoxidil, cromakalim, pinacidil, or a compound selected from the classes of potassium channel openers such as s-triazine derivatives, benzopyran derivatives, pyridinopyran derivatives and thiane-1-oxide compounds; and an androgen receptor blocker, such as 4-(5-methoxyheptyl)-hexahydro-2(lH)-pentalenone (CAS Registry # 89672-11-7).
  • a potassium channel opener such as minoxidil, cromakalim, pinacidil, or a compound selected from the classes of potassium channel openers such as s-triazine derivatives, benzopyran derivatives, pyridinopyran derivatives and thiane-1-oxide compounds
  • an androgen receptor blocker such as 4-(5-methoxyheptyl)-hexahydro-2(l
  • Another approach has been to attempt to identify and quantify the biological mechanisms responsible for the initiating and controlling hair growth at the follicullar level and intervening with therapeutic agents which stimulate hair growth. It is well known in the art that the onset of puberty results in changes in endocrine levels which result in, among other changes, the stimulation of facial hair growth (males), axillary hair growth (males and females), and pubic hair growth (males and females).
  • One class of compounds implicated in these effects are the androgens.
  • Androgens appear to play a major role in the development and progression of androgenetic alopecia (male pattern baldness).
  • Rittmaster R. S., Gin. Dermatol., 6, 122 (1988). This was demonstrated in humans, in that prepubertally castrated men do not develop male pattern baldness. Hamilton, J. B., Am. J. Anat., 71, 451 (1942).
  • DHT dihyrdotestosterone
  • Antiandrogen therapy offers a potential intervention to the treatment of male pattern baldness in men, and in women where it has been suggested that elevated androgen levels are responsible for the appearance of male pattern baldness.
  • This class of compounds, the antiandrogens have been subdivided into two major catagories, the androgen receptor blockers and the 5 ⁇ -reductase inhibitors. Androgen receptor blockers interfere with the binding of androgens, testosterone and dihydrotestosterone (DHT), to their receptors, while 5 ⁇ -reductase inhibitors prevent the conversion of testosterone into DHT.
  • DHT dihydrotestosterone
  • the remaining class of antiandrogens is the 5c_-reductase inhibitors. These compounds block action of 5 ⁇ -reductase and thus reduce the level of DHT in the peripheral tissue.
  • potassium channel openers are useful in the treatment of androgenetic alopecia.
  • the subject invention is directed toward an improved method for promoting hair growth in mammals comprising the administration of a potassium channel opener in an effective amount and the administration of 4-(5-methoxyheptyl)-hexahydro-2(lH)-pentalenone in an effective amount whereby hair growth is increased over the sole administration of the potassium channel opener.
  • the routes of administration for either component can be by any of various means, preferably orally, topically or any combination of the two. More preferably and conveniently, the two components are applied together topically.
  • the potassium channel opener can be administered topically in an amount of from about .01 to about 20 percent by weight, or orally in an amount of from about .001 to about 50 mg/kg body weight.
  • the 4-(5-methoxyheptyl)-hexahydro-2(lH)-pentalenone can be administered topically in an amount of from about 0.01 to about 15 percent by weight of composition or administered orally in an amount of from about 0.001 to about 10 mg/kg body weight.
  • the potassium channel opener and/or 4-(5-methoxyheptyl)-hexahydro-2(lH)-pentalenone is generally administered in a pharmaceutical carrier adapted for oral administration or in a pharmaceutical acceptable carrier adapted for topical application.
  • the potassium channel opener and 4-(5-methoxyheptyl)-hexahydro-2(lH)- pentalenone are combined into a pharmaceutical carrier adapted for topical application.
  • the potassium channel opener can be routinely applied to an area of treatment concomitant with the administration of 4-(5-methoxyheptyl)-hexahydro-2(lH)-pentalenone.
  • the potassium channel opener is minoxidil, cromakalim, pinacidil, or a compound selected from the chemical classes of s-triazines, thiane-1-oxides, benzopyrans, pyridinopyrans and derivatives thereof or a pharmaceutically acceptable salt thereof.
  • the subject invention is directed toward a pharmaceutical composition
  • a pharmaceutical composition comprising an effective amount of a potassium channel opener, an effective amount of 4-(5- methoxyheptyl)-hexahydro -2(lH)-pentalenone and a pharmaceutical carrier adapted for topical application.
  • the pharmaceutical carrier can be petrolatum, lanolin, propylene glycol, N-methyl-2- pyrrolidinone, polyethylene glycol, oleyl alcohol, ethyl alcohol or mixtures thereof.
  • the present invention relates to a method for promoting hair growth which means to increase normal hair growth or restore hair growth in mammals, including humans, suffering from hair growth disorders such as alopecia or male pattern baldness.
  • the promotion or restoration of hair growth has been discovered to be significantly enhanced by the concomitant administration of a potassium channel openers (activators); and an androgen receptor blocker, 4-(5 -methoxyheptyl)- hexahydro-2(lH)-pentalenone.
  • Typical examples of "potassium channel openers” or “potassium channel opener vasodilators” as contemplated by the subject invention are minoxidil, cromakalim, pinacidil, and those compounds selected from the chemical classes of s-triazines, be ⁇ zopyran, pyridinopyran and thiane- 1 -oxides their derivatives and pharmaceutically acceptable salts.
  • Chemically minoxidil is 6-a ⁇ mo-l,2-dihydro-hydroxy-2-imino-4-piperidinopyrimidine and analogs thereof. The preparation of these compounds are described in U.S. Patents 3,382,247, 3,461,461 and 3,644,364 and J.M. McCall, et al., /.
  • Minoxidil means any of the various forms of - _____ino-l,2-dihydro-hydroxy-2-immo-4-piperidinopyrimidine, derivatives and analogs thereof. Minoxidil is distributed by The Upjohn Company, Kalamazoo, MI.
  • Chemically cromakalim is (3S-trans) 3,4-dihydro-3-hydroxy-2,2-dimethyl-4-(2-oxo-l- pyrrolidinyl)-2H-l-be__xopyran-6-carbonitrile, a molecular wight of 286.33 g. and a melting point of 224.5 -225.5°C. Cromakalim is distributed by SmithKline Consumer Products, Philadelphia, PA.
  • Pinacidil is chemically, N-cyano-N'-4-pyridinyl-N"-(l,2,2-trimethylpropyl)-guanidine monohydrate, a molecular weight of 263.34 g. and a melting point of 110-116°C.
  • the preparation of pinacidil is described in US Patent 4,057,636 and German Patent 2,557,438 and is distributed by Eli Lilly and Company, Indianapolis, IN.
  • S-triazine compounds or 2,6-di___nino-4-substituted-s-triazine-l-oxides are described in U.S.
  • Thiane-1-oxide compounds are described in U.S. Patent 4,568,682 assigned to Rhone-Poulenc Sante, Courbevoie, France.
  • An example of such a compound contemplated by the subject invention is N-methyl-2-(pyridin-3-yl)tetrahydrothiopyran-2-carbothioamide-l-oxide.
  • Other derivatives include those disclosed in patent applications EP 321 274 A, EP 321 273 A, and EP 326 297 A.
  • potassium channel openers include pyranopyridine derivatives described in patent applications GB 2204 868 A and benzopyran derivatives described in patent applications GB 2204 868 A, EP 314 446 A2, EP 339 562 A, EP 340 718 A, EP 337 179, AU A 18556/88, JA 1294 677 A, EP 359 537 A, and US Patent 4,900,752.
  • salts of the potassium channel openers are for example acid addition salts which may be chosen from the following: acetate, adipate, alginate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, citrate, camphorate, camphorsulfonate, cyclo- pentanepropionate, digluconate, dodecylsulfate, ethanesulfonate, fumarate, glucoheptanoate, glycerophosphate, hemisulfate, heptanoate, hexanoate, hydrochloride, hydrobromide, hydroiodide, 2-hydroxyethanesulfonate, lactate, maleate, methanesulfonate, 2-naphthalenesulfonate, nicotinate, oxalate, pamoate, pectinate, persulfate, 3-phenylpropionate, picrate, pival
  • Pharmaceutically acceptable cationic addition salts of the potassium channel openers include: pharmacologically acceptable metal cations, ammonium, amine cations, or quaternary ammonium cations.
  • pharmacologically acceptable metal cations are those derived from the alkali metals, e.g., lithium, sodium, and potassium, and from the alkaline earth metals, magnesium and calcium, although cationic forms of other metals, e.g., aluminum, zinc, and iron are also within the scope of this invention.
  • Pharmacologically acceptable amine cations are those derived from primary, secondary, and tertiary amines.
  • the second essential, active ingredient of the subject invention is the compound 4-(5-methoxyheptyl)-hexahydro-2(lH)-pentalenone, (hereinafter referrred to as "MHP") which has a molecular weight of 252.40.
  • MHP 4-(5-methoxyheptyl)-hexahydro-2(lH)-pentalenone
  • This compound is an androgen receptor blocker and is described in US 4,689,345 and US 4,855,322, assigned to CBD Corp., Los Angeles, CA.
  • This publication discloses various analogs of MHP all of which are disclosed to be active as androgen receptor blockers and thus are useful for the treatment of androgenic alopecia, including male pattern alopecia.
  • the preferred administration of MHP is topical.
  • MHP can be administered by any of various routes as well as can be the potassium channel opener.
  • Administration routes for the two components of the subject invention can be topically, orally, parenterally or rectally.
  • MHP is administered either topically with the potassium channel opener or orally while the potassium channel opener is applied topically.
  • the administration route would be to compound MHP with a potassium channel opener in a pharmaceutical, topical vehicle.
  • the potassium channel opener and optionally the 4-(5-methoxyheptyl)-hexahydro- 2(lH)-pentalenone compound are applied to the skin region where hair growth is desired with a pharmaceutical carrier.
  • the pharmaceutical carrier is adopted for topical application such as those pharmaceutical forms which can be applied externally by direct contact with the surface to be treated.
  • Conventional pharmaceutical forms for this purpose include ointments, waxes, gels, lotions, pastes, jellies, sprays, aerosols, and the like in aqueous or nonaqueous formulations.
  • moisturizer embraces formulations (including creams) having oleaginous, absorption, water-soluble and emulsion-typebases, e.g., petrolatum, lanolin, polyethylene glycols, N-methyl -2-pyrrolidinone, oleyl alcohol as well as mixtures of these. Preparation of minoxidil topical compositions are disclosed in U.S. Patents 4,139,619 and
  • the potassium channel openers and/or the 4-(5-me ⁇ oxyheptyl)-hexahydro-2(lH)- pentalenone compound can be admixed with other compounds for the treatment of hair growth.
  • Such compounds which can be included in the overall composition or treatment are various combinations of the potassium channel openers, vasoconstrictors such as betamethasone dipropionate, corticosteroids such as hydrocortisone, scopolamine, and antiandrogens such as 17/S- (N-te/ -butylcarbamoyl)-4-aza-5-_--androst-l-en-3-one and cyproterone acetate.
  • a potassium channel opener is used in an effective amount that is an amount sufficient to promote hair growth or treat hair growth disorders such that hair growth is increased or produced.
  • the potassium channel opener is added in an amount of from about 0.001 to about 10, preferably, 0.01 to about 5 percent by weight of the composition.
  • the 4-(5-methoxyheptyl)-hexahydro-2(lH)-pentalenone compound is used in an effective amount, that is, an amount sufficient to promote hair growth or treat hair growth disorders such that hair growth is increased or produced over that which would be increased or produced by the administration of a potassium channel opener alone.
  • the androgen receptor blocker, MHP is added in an amount of from about 0.0001 to about 10, preferably, 0.001 to about 5 percent by weight of the composition.
  • the compound or formulated composition can be applied to the area to be treated, in mammals such as the scalp in humans, by spraying, dabbing or swabbing. Other less specific methods can be employed provided the active ingredients) are delivered to the region of a hair follicle.
  • the compound or formulated composition is periodically applied to the treatment area on a routine basis prior to, during and subsequent to hair growth.
  • routine treatment would be to apply the compound or formulated composition at least daily, preferably twice daily although more frequent applications can be used.
  • the percentage by weight of the active ingredients, potassium channel opener and 4-(5- me ⁇ oxyheptyl)-hex___ydro-2(lH)-pentalenone compound herein utilized ranges from an effective amount which is an amount sufficient to increase normal hair growth or treat various forms of alopecia whereby the hair growth is significantly more than if either of the compounds were solely administered.
  • the pharmaceutical carrier for topical applications constitutes a major amount of the preparation.
  • the active ingredient is in a range of from about 0.01 to about 15 percent total weight of the topical composition, preferably 0.1 to 10 percent total weight.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)

Abstract

L'invention se rapporte à un procédé et à une composition améliorés servant à favoriser la croissance des cheveux chez l'homme en vue de traiter diverses formes d'alopécie ou de calvitie hyppocratique. Un tel procédé consiste à administrer conjointement: des agents d'ouverture des vannes à potassium, tels que minoxidil, cromakalim, pinacidil, ou un composé choisi parmi les classes des composés s-triazine, thiane-1-oxyde, benzopyranne et pyridinopyranne; et un agent bloquant les récepteurs d'androgènes, la 4-(5-méthoxyhaeptyl)-hexahydro-2(1H)-pentalénone. Dans ce procédé, on administre une dose efficace de l'agent d'ouverture des vannes à potassium et une dose efficace de la 4-(5-méthoxyhaeptyl)-hexahydro-2(1H)-pentalénone, pour que la croissance des cheveux soit favorisée à une degré plus élevé que par la seule administration de l'agent d'ouverture des vannes à potassium.
PCT/US1991/008306 1990-11-29 1991-11-14 Stimulation de la croissance des cheveux utilisant des agents d'ouverture des vannes a potassium et un agent bloquant les recepteurs d'androgenes WO1992009259A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US61983990A 1990-11-29 1990-11-29
US619,839 1990-11-29

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999008673A1 (fr) * 1997-08-13 1999-02-25 Bristol-Myers Squibb Company Enantiomeres de 4-[[(cyanoimino)- [(1,2,2-trimethylpropyl) amino] methyl]amino] benzonitrile
WO2000034287A3 (fr) * 1998-12-04 2000-10-12 Cambridge Bioclinical Limited Activateurs des canaux de potassiques et leur utilisation
RU2182478C1 (ru) * 2001-04-25 2002-05-20 Московская медицинская академия им. И.М. Сеченова Стимулятор роста волос
US6458835B2 (en) 1997-08-13 2002-10-01 Bristol-Myers Squibb Company Method of inhibiting or treating chemotherapy-induced hair loss
EP4274546A4 (fr) * 2021-01-06 2024-12-11 The Penn State Research Foundation Méthodes et matériaux de traitement contre la perte de cheveux
US12268677B2 (en) 2022-04-27 2025-04-08 The Penn State Research Foundation 4-aminopyridine (4-AP) and bone morphogenetic protein 2 (BMP-2)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1983004019A1 (fr) * 1982-05-06 1983-11-24 Cbd Corporation Composes cycloaliphatiques pharmaceutiques
JPS6156118A (ja) * 1984-08-27 1986-03-20 Kanebo Ltd 養毛化粧料
WO1987000427A1 (fr) * 1985-07-18 1987-01-29 Proctor Peter H Composition topique et procede destines a stimuler la croissance des cheveux
DE3615396A1 (de) * 1986-05-07 1987-11-12 Wella Ag Mittel zur behandlung der haare und der kopfhaut

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1983004019A1 (fr) * 1982-05-06 1983-11-24 Cbd Corporation Composes cycloaliphatiques pharmaceutiques
JPS6156118A (ja) * 1984-08-27 1986-03-20 Kanebo Ltd 養毛化粧料
WO1987000427A1 (fr) * 1985-07-18 1987-01-29 Proctor Peter H Composition topique et procede destines a stimuler la croissance des cheveux
DE3615396A1 (de) * 1986-05-07 1987-11-12 Wella Ag Mittel zur behandlung der haare und der kopfhaut

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Chemical Abstracts, vol. 105, no. 8, 1986 (Columbus, Ohio, US), & JP, A, 61056118 (KANEBO LTD) 20 March 1986, see abstract *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999008673A1 (fr) * 1997-08-13 1999-02-25 Bristol-Myers Squibb Company Enantiomeres de 4-[[(cyanoimino)- [(1,2,2-trimethylpropyl) amino] methyl]amino] benzonitrile
US6013668A (en) * 1997-08-13 2000-01-11 Bristol-Myers Squibb Company Enantiomers of 4-[[(cyanoimino) [(1,2,2-trimethylpropyl) amino]methyl]amino]benzonitrile
US6262122B1 (en) 1997-08-13 2001-07-17 Bristol-Myers Squibb Company Enantiomers of 4-[[(cyanoimino) [(1,2,2-trimethylpropyl)amino]methyl]amino]benzonitrile
US6458835B2 (en) 1997-08-13 2002-10-01 Bristol-Myers Squibb Company Method of inhibiting or treating chemotherapy-induced hair loss
US6472427B1 (en) 1997-08-13 2002-10-29 Bristol-Myers Squibb Company Enantiomers of 4-[[(cyanoimino) [(1,2,2-trimethylpropyl)amino]methyl]amino]benzonitrile
WO2000034287A3 (fr) * 1998-12-04 2000-10-12 Cambridge Bioclinical Limited Activateurs des canaux de potassiques et leur utilisation
US6342517B1 (en) 1998-12-04 2002-01-29 Cambridge Bioclinical Limited Potassium channel activators and their use
RU2182478C1 (ru) * 2001-04-25 2002-05-20 Московская медицинская академия им. И.М. Сеченова Стимулятор роста волос
EP4274546A4 (fr) * 2021-01-06 2024-12-11 The Penn State Research Foundation Méthodes et matériaux de traitement contre la perte de cheveux
US12268677B2 (en) 2022-04-27 2025-04-08 The Penn State Research Foundation 4-aminopyridine (4-AP) and bone morphogenetic protein 2 (BMP-2)

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