WO2001072727A1 - Toniques capillaires - Google Patents

Toniques capillaires Download PDF

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Publication number
WO2001072727A1
WO2001072727A1 PCT/JP2001/002349 JP0102349W WO0172727A1 WO 2001072727 A1 WO2001072727 A1 WO 2001072727A1 JP 0102349 W JP0102349 W JP 0102349W WO 0172727 A1 WO0172727 A1 WO 0172727A1
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WIPO (PCT)
Prior art keywords
group
hair
amino
compound
salt
Prior art date
Application number
PCT/JP2001/002349
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English (en)
Japanese (ja)
Inventor
Tokuro Iwabuchi
Hirotada Fukunishi
Koji Kobayashi
Masahiro Tajima
Original Assignee
Shiseido Co., Ltd.
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Filing date
Publication date
Application filed by Shiseido Co., Ltd. filed Critical Shiseido Co., Ltd.
Publication of WO2001072727A1 publication Critical patent/WO2001072727A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • 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
    • A61K31/433—Thidiazoles
    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • 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
    • 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
    • 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
    • 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

Definitions

  • the present invention relates to a hair restorer, a hair restorer containing a special amide derivative as an active ingredient.
  • hair restoration agents also referred to as hair restoration agents and hair growth promoters
  • hair restoration agents that aim to promote hair growth and hair loss of the hair in the past have either eliminated the above-mentioned causes, or Compounds or compositions having a mitigating effect are generally incorporated.
  • vitamins such as vitamin B and vitamin E, amino acids such as serine and methionine, vasodilators such as sempri extract and acetylcholine derivatives, anti-inflammatory agents such as purple root extract and hinokitiol, female hormones such as estradiol, Contains skin function enhancers such as cepharanthin.
  • An object of the present invention is to provide a hair restorer having an excellent hair restore effect such as prevention of hair loss and promotion of hair growth.
  • the hair restorer according to the present invention comprises a thiadiazole represented by the following general formula (I).
  • RR 2 is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylamino group, a cyclic amino group, a lower alkylaminoalkyl group, a cyclic aminoalkyl group, a benzyloxy group, or It is a group represented by R (R is an unsaturated aliphatic hydrocarbon group).
  • R 3 is a hydrogen atom, an aryl group, a pyridyl group, a lower alkylamino group, or a cyclic amino group.
  • A is a divalent saturated hydrocarbon group having 1 to 5 carbon atoms.
  • R 1 is preferably a hydrogen atom.
  • R 2 is a lower alkyl group.
  • R 2 is a lower alkoxy group.
  • R 2 is a lower alkylamino group.
  • R 2 is a cyclic aminoalkyl group.
  • R 2 is —O—R (R is an unsaturated aliphatic hydrocarbon group). Further, it is preferable that R 2 is a hydrogen atom.
  • R 1 and R 2 are preferably a lower alkyl group.
  • R 1 is preferably a benzyloxy group
  • R 2 is preferably a lower alkyl group.
  • R 3 is preferably a lower alkylamino group or a cyclic amino group.
  • R 3 is a hydrogen atom.
  • A is preferably an ethylene group or a propylene group.
  • the thiadiazole amide derivative according to the present invention is a compound represented by the following general formula (IA) or a salt thereof.
  • RR 2 is a hydrogen atom or an alkyl group having 7 to 10 carbon atoms, but at least one of R 1 R 2 is not a hydrogen atom.
  • R 3 is a hydrogen atom, an aryl group, a pyridyl group, a lower alkylamino group, or a cyclic amino group.
  • A is a divalent saturated hydrocarbon group having 1 to 5 carbon atoms.
  • A—R 3 is preferably — (CH 2 ) 2 —N (C 2 H 5 ) 2 .
  • R 1 is preferably a hydrogen atom
  • R 2 is preferably an n-octyl group.
  • thiadiazolamide derivative according to the present invention is 2- (4-n-pentylbenzoyl) amino-5-getylaminoethylthio-1,3,4-thiadiazole or a salt thereof.
  • thiadiazolamide derivative according to the present invention is 2- (4-n-hexylbenzoyl) amino-5-decylaminoethylthio-1,3,4-thiadiazole or a salt thereof.
  • the thiadiazole amide derivative according to the present invention is 2- (4-dimethylaminobenzoyl) amino-5-decylaminoethylthio-1,3,4-thiadiazole or a salt thereof.
  • the thiadiazole amide derivative according to the present invention is characterized in that it is 2- (dimethylaminobenzoyl) amino-5-decylaminoethylthio-1,3,4-thiadiazole or a salt thereof. I do.
  • the thiadiazole amide derivative according to the present invention is 2- (3-piperidinomethylbenzoyl) amino-5- [3- (dimethylamino) propyl] thio-1,3,4-thiaziazole or a salt thereof. It is characterized by.
  • the thiadiazole amide derivative according to the present invention is characterized in that it is 2_benzoylamino-5-diethylaminoethylthio-1,3,4-thiadiazole or a salt thereof.
  • the lower alkyl group for R 1 and R 2 is a linear or branched alkyl group having 1 to 10 carbon atoms.
  • methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, 1-methylpropyl, tert-butyl, n-pentyl, 1-ethylpropyl, isoamyl examples thereof include n-hexyl group, n-octyl group, n-nonyl group, and n-decyl group, and preferably n-octyl group.
  • the definition of a lower alkyl group is the same as described above, unless otherwise specified.
  • the lower alkoxy group in R ⁇ R 2 means a hydroxyl group having a hydrogen atom replaced by a lower alkyl group, preferably a branched lower alkoxy group, particularly preferably an isopropoxy group or a tert-butoxy group. .
  • the definition of lower alkoxy is the same unless otherwise specified.
  • R ] and R 2 can also be substituted amino groups such as lower alkylamino groups or cyclic amino groups.
  • a lower alkylamino group is an amino group in which the hydrogen atom has been substituted by one or two identical or different lower alkyl groups.
  • the cyclic amino group is a 4- to 8-membered saturated monocyclic amino group, and includes, for example, an azetidino group, a pyrrolidino group, a piperidino group and the like.
  • a lower Al Kiruamino group particularly preferably tert- Puchiruamino group, Jimechiruamino group.
  • R 1 R 2 can also be an amino-substituted alkyl group such as a lower alkylaminoalkyl group or a cyclic aminoalkyl group. Of these, a cyclic aminoalkyl group is preferred, and a piperidinomethyl group is particularly preferred.
  • the benzyloxy group in R ⁇ R 2 is a group in which one or more substituents selected from a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylamino group, a cyclic amino group, a nitro group and a cyano group are present on the benzene ring. You may have two. Among these substituents, preferred are halogen atoms, and particularly preferred is fluorine.
  • R 1 R 2 can also be a group represented by _ ⁇ R.
  • R means a linear or branched unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms containing at least one double bond, and is preferably a branched chain.
  • branched unsaturated aliphatic hydrocarbon group a prenyl group, a geranyl group, a neryl group, a phenylesyl group and the like are preferable, and a geranyl group is particularly preferable.
  • R 1 is a hydrogen atom and R 2 is a hydrogen atom, a lower alkyl group or a cyclic aminoalkyl group.
  • R 3 can be a hydrogen atom, an aryl group such as a phenyl group or a naphthyl group, or a pyridyl group.
  • the aryl group and the pyridyl group may have one or two substituents such as a lower alkyl group on the ring.
  • R 3 can also be a substituted amino group such as a lower alkylamino group or a cyclic amino group.
  • the lower alkylamino group for R 3 is preferably a dimethylamino group, a getylamino group, or a diisopropylamino group, and particularly preferably a getylamino group.
  • the cyclic amino group for R 3 is preferably a piperidino group. Among them, R 3 is preferably a lower alkylamino group or a cyclic amino group, and particularly preferably a lower alkylamino group.
  • Examples of the divalent saturated hydrocarbon group having 1 to 5 carbon atoms in A include a methylene group, an ethylene group, a propylene group, a 2-methylpropylene group, a butylene group, and a pentylene group. is there.
  • the thiadiazole amide derivative and a salt thereof according to the present invention can be produced by a known method.
  • a known amide such as a mixed acid anhydride method, an acid chloride method, a DCC method, a CDI method or an azide method is prepared from the following carboxylic acid (II) and substituted thiadiazole (III).
  • the compound (I) of the present invention can be obtained by a bond formation reaction.
  • Carboxylic acids ( ⁇ ) are commercially available or can be easily synthesized from benzoic acids having the corresponding functional groups.
  • a carboxylic acid (II) in which R 1 or R 2 is a lower alkoxy group, a lower alkylamino group, or one O—R is obtained by protecting a carboxyl group of a benzoic acid having a hydroxyl group or an amino group on a benzene ring.
  • it can be obtained by introducing a lower alkyl group or a group R into the hydroxyl group or the amino group, and then deprotecting the carboxyl group protecting group.
  • the introduction of the lower alkyl group or the group R is carried out by a reaction with a corresponding alcohol or alkene under acidic conditions, or a reaction with a corresponding alkyl halide or R—X (X is a halogen) under basic conditions. , It can be carried out.
  • Carboxylic acid (II) in which R 1 or R 2 is a lower alkylaminoalkyl group or a cyclic aminoalkyl group is obtained by protecting a carboxyl group of a benzoic acid having an alkyl group in a benzene ring, and then adding a halogen to the alkyl group.
  • a halogen By substituting the halogen with a lower alkylamino group or a cyclic amino group under basic conditions, and then deprotecting the carboxyl group-protecting group.
  • the introduction of the halogen can be carried out using ⁇ ⁇ -promosuccinimide (NBS), ⁇ ⁇ ⁇ -chlorosuccinimide (NCS) or the like.
  • Carboxylic acid (II) in which R 1 is a lower alkyl group and R 2 is a benzyloxy group protects the carboxyl group of benzoic acid having a lower alkyl group and a hydroxyl group on a benzene ring, and then reacts with the corresponding benzyl group. It can be obtained by reacting with a halide under basic conditions to convert the hydroxyl group to a benzyloxy group and then deprotecting the carboxyl protecting group.
  • the starting compound in this case is commercially available or can be synthesized by a known method.
  • benzoic acid having a hydroxyl group on the benzene ring After the carboxyl group is protected, the hydroxyl group is reacted with the corresponding alkenyl halide under basic conditions to convert the hydroxyl group to an alkenyloxy group. It can be obtained by performing it sequentially.
  • R 1 or R 2 is a cyclic amino group
  • a known amide bond-forming reaction can be carried out from a benzoic acid having a halogen such as chlorine on the benzene ring as a substituent and a substituted thiadiazole (III).
  • the desired compound of the present invention (I) can be obtained by forming a thiadiazole amide and then substituting the halogen with a cyclic amine.
  • the substitution reaction of a halogen with a cyclic amine is usually carried out at 70 to 140 ° C in the absence of a solvent, and if necessary, a carbonated lime and copper chloride (II) or copper oxide (II) are added. Is also good.
  • substituted thiadiazoles ( ⁇ ⁇ ) react, for example, with 2-amino-5-mercapto-1,3,4-thiadiazole and the corresponding halide X—A—R 3 under basic conditions.
  • the thiadiazole amide derivative which is an active ingredient of the hair restorer according to the present invention is exemplified below.
  • the mechanism of action of the thiadiazoamide derivative according to the present invention is not clear, it has an excellent hair growth promoting effect and an effect of extending the growth period of the hair cycle. Therefore, by applying this to the scalp, it is possible to treat, improve and prevent hair loss.
  • thiadiazolamide derivative according to the present invention can be prepared according to Japanese Patent Application Laid-Open No. 9-249496 (US Pat. No. 5,912,258). It is.
  • Hair restoration agents containing the thiadiazole amide derivative as an active ingredient include so-called androgenetic alopecia and androgenetic alopecia, light hair and alopecia as well as alopecia areata, pityriasis alopecia, and seborrheic alopecia. It can be applied to experimental alopecia.
  • the amount of the thiadiazole amide derivative to be used should be appropriately determined according to gender, age, the degree of symptoms such as hair loss and light hair, etc., but is usually 0.01 to 50 mg / kg'd. , Preferably 0. 220 mg / kg. Apply or spray the scalp once or several times a day.
  • the dosage form can be arbitrarily selected as long as the effect of the present invention can be exerted.
  • examples include creams, gels, aerosols, and mousses. Specific examples include tonics, lotions, conditioners, scanolep treatments, shampoos and rinses.
  • a component that can be generally added to a pharmaceutical or a cosmetic may be added in such an amount that the effects of the present invention are not impaired. it can.
  • the medicinal component as a drug having a blood circulation promoting action, there may be mentioned, for example, assembly extract, vitamin E and its derivatives, and nicotinic acid esters such as benzyl nicotinate.
  • Drugs that promote blood circulation by local irritation include pepper tincture, tincture tincture, camphor, penilyl nonylate, and the like.
  • Examples of the drug having a hair follicle activating action include hinokitiol, placentadex, photosensitizer, pantothenic acid and derivatives thereof.
  • Examples of the drug having an antiandrogen action include hormonal drugs such as estradiol, ethelestradiol, and estrone. Iou Examples of drugs having antiseborrheic action, Chiokisoron include vitamin B 6, and the like.
  • salicylic acid and resorcinol which have a keratolytic and bactericidal action to prevent dandruff, and glycyrrhizic acid and its derivatives, glycyrrhetinic acid and its derivatives, and menthol to prevent scalp inflammation.
  • amino acids such as serine, methionine, and arginine
  • vitamins such as biotin, herbal extracts, and the like are used for nutritional supplementation of hair follicles and activation of enzyme activity.
  • vasodilators such as alkoxycarbonylpyridine N-oxide, carpronium chloride, and acetylcholine derivatives; skin function enhancers such as cepharanthin; Antibacterial agents such as acid, trichlorocarbanide, bithino monozole, phenol, isopropinolemethi / lefeno monole; zinc and its derivatives; lactic acid or its alkyl ester; citric acid; succinic acid; organic acids such as malic acid; Protease inhibitors such as tranexamic acid and the like may be added.
  • drugs such as cyclosporins, oxendrone, diazoxide, minoxidil and the like can be used.
  • alcohols such as ethanol and isopropyl alcohol
  • polyhydric alcohols such as glycerin, propylene glycol and polyethylene dalicol
  • oils such as higher fatty acids, higher alcohols, hydrocarbon oils, natural oils and fats, ester oils, and silicone oils.
  • Surfactants fragrances; chelating agents; moisturizing agents such as 1,3-butylene glycol, hyal humic acid and its derivatives, maltitol, atelocollagen, sodium lactate; malmella mucilage, lipoxyvinyl polymer, xanthan gum Viscosity agents, etc .; High molecular compounds: Antioxidants: Ultraviolet absorbers; Dyes; Water; Stabilizers, and other components normally used in pharmaceuticals and cosmetics.
  • the hair growth test was performed using C3H I HeNCrj mice in the telogen phase of the hair cycle, using the method of Ogawa et al. (Normal and Abnormal Epidermal Differentiation ⁇ M. Seiji and IA Bernstein, 159 ⁇ 170 pages, 1982, University of Tokyo Press). That is, 10 mice per group, the back of each mouse was shaved by 3 x 4 cm with a norican, and 0.1 ml of ethanol (negative control) or ethanol solution of each test compound was added once a day. Applied.
  • the hair growth effect of each test compound was measured 30 days after the start of application by measuring the area of the hair growth part on the back of the mouse and evaluating the ratio of the area of the hair growth part to the area of the shaved part as the hair regeneration area ratio (%). did.
  • Table 1 shows the average hair regeneration area ratio.
  • Test Example 2 Growth period extension effect on hair cycle
  • Hei 1 0 2 6 5 3 4 1 JP, c the test method tested is brought into contact with the target substance to the hair follicle epithelial cultured cells in serum-free medium
  • cultured follicular epithelial cells of rat body hair obtained by the method described in Japanese Patent Application Laid-Open No. 10-265341 were used.
  • KGM medium epidermal keratinocytes basal medium
  • Target substance-containing medium The target substance was dissolved in DMSO and added to KBM medium to a final concentration of 1.0 X 1 CT 7 M (DMS O concentration 0.1%).
  • the cell growth promotion index of KBM medium is 0,
  • the cell growth promotion index of the positive control is 1.
  • the pituitary pituitary extract, h-EGF, in the positive control is a substance that is known to affect the proliferation of hair follicle epithelial cells in culture.
  • the thiadiazole amide derivative according to the present invention exhibited a growth activity of hair follicle epithelial cell culture. This suggests that these derivatives have an action of maintaining or prolonging the anagen phase of the hair cycle by maintaining the mitotic proliferation activity of hair follicle epithelial cells.
  • Dissolve POE 40 hydrogenated castor oil and fragrance in 95% ethanol, then add purified water. After the addition, the other components were added and dissolved by stirring to obtain a clear liquid lotion.
  • POE 40 hydrogenated castor oil and flavor were dissolved in 95% ethanol, purified water was added, and then other components were added, followed by stirring and dissolution to obtain a transparent liquid lotion.
  • Vitamin E acetate 0.02
  • phase A and B were each heated and dissolved at 60 ° C., mixed, and treated with a homomixer to prepare a gel.
  • Phase D was gradually added to this gel and dispersed with a homomixer.
  • the previously dissolved phase C was added to the gel dispersion, and the previously dissolved phase E was added, and emulsified with a homomixer to obtain a ZW type emulsion.
  • An undiluted solution was prepared by mixing and dissolving the ingredients of the undiluted solution, filled in a can, fitted with a valve, and filled with gas to obtain an aerosol spray.
  • the purified water was heated to 70 ° C., and the components (1) and (9) were sequentially added, mixed by stirring and dissolved, and cooled to obtain a shampoo.
  • (1), (3), and (4) were added to the purified water, and the mixture was heated to 70 ° C. to obtain an aqueous phase.
  • the other components were heated and melted and heated to 70 ° C to obtain an oil phase.
  • the oil phase was added to the aqueous phase, mixed by stirring with an emulsifier, and cooled to obtain a rinse.
  • the stock solution was filled in a can with a propellant to obtain a scalp treatment.
  • Formulation Example 1 1 Scalp treatment
  • a scalp treatment was obtained in the same manner as in Preparation Example 10.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Cosmetics (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne des toniques capillaires présentant d'excellents effets de prévention de la perte des cheveux par croissance capillaire et de pousse de nouveaux cheveux. Lesdits toniques capillaires contiennent, en tant qu'ingrédient actif, des dérivés thiadiazolamide ou leurs sels représentés par la formule générale (I), dans laquelle R1 et R2 représentent chacun H, alkyle inférieur, alcoxy inférieur, alkylamino inférieur, amino cyclique, alkylaminoalkyle inférieur, aminoalkyle cyclique, benzyloxy, ou-O-R (où R représente un groupe hydrocarbure aliphatique); R3 représente H, aryle, pyridyle, alkylamino inférieur, ou amino cyclique; et A représente un groupe hydrocarbure saturé divalent.
PCT/JP2001/002349 2000-03-27 2001-03-23 Toniques capillaires WO2001072727A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2000-86638 2000-03-27
JP2000086638A JP2001278873A (ja) 2000-03-27 2000-03-27 養毛剤

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WO2001072727A1 true WO2001072727A1 (fr) 2001-10-04

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Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007254323A (ja) * 2006-03-22 2007-10-04 Shiseido Co Ltd 毛髪はり・こし改善剤および毛髪用化粧料

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4184039A (en) * 1977-12-01 1980-01-15 Paul Finkelstein Benzothiadiazine 1, 1-dioxides
WO1992014439A1 (fr) * 1991-02-18 1992-09-03 Chugai Seiyaku Kabushiki Kaisha Agent stimulant la croissance des cheveux
EP0579129A2 (fr) * 1992-07-14 1994-01-19 LABORATORIO FARMACEUTICO C.T. S.r.l. Dérivés de thiadiazole pour le traitement des états dépressifs

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4184039A (en) * 1977-12-01 1980-01-15 Paul Finkelstein Benzothiadiazine 1, 1-dioxides
WO1992014439A1 (fr) * 1991-02-18 1992-09-03 Chugai Seiyaku Kabushiki Kaisha Agent stimulant la croissance des cheveux
EP0579129A2 (fr) * 1992-07-14 1994-01-19 LABORATORIO FARMACEUTICO C.T. S.r.l. Dérivés de thiadiazole pour le traitement des états dépressifs

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