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WO2016085160A2 - 발모촉진용 또는 탈모방지용 조성물 - Google Patents

발모촉진용 또는 탈모방지용 조성물 Download PDF

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Publication number
WO2016085160A2
WO2016085160A2 PCT/KR2015/012099 KR2015012099W WO2016085160A2 WO 2016085160 A2 WO2016085160 A2 WO 2016085160A2 KR 2015012099 W KR2015012099 W KR 2015012099W WO 2016085160 A2 WO2016085160 A2 WO 2016085160A2
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WO
WIPO (PCT)
Prior art keywords
composition
hair
hair growth
oxide
hair loss
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Application number
PCT/KR2015/012099
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English (en)
French (fr)
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WO2016085160A3 (ko
Inventor
정세규
배종환
박부만
김대환
Original Assignee
(주)네오팜
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.)
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Priority claimed from KR1020150102490A external-priority patent/KR101696857B1/ko
Application filed by (주)네오팜 filed Critical (주)네오팜
Priority to US15/519,822 priority Critical patent/US10016351B2/en
Publication of WO2016085160A2 publication Critical patent/WO2016085160A2/ko
Publication of WO2016085160A3 publication Critical patent/WO2016085160A3/ko

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    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/164—Amides, e.g. hydroxamic acids of a carboxylic acid with an aminoalcohol, e.g. ceramides
    • 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
    • A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • 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 composition for promoting hair growth or preventing hair loss, and in detail, has excellent stability against skin, no side effects, promotes hair growth, delays hair loss, and prevents hair loss, and has excellent hair growth effect. It's about. Background
  • Hair loss is increasing due to increased stress, doubled environmental pollution and instant foods such as eating habits, frequent perm and dyeing, and poor scalp care.
  • the growth stage that grows the hair
  • the catagen which stops growth and shrinks the hairball
  • the nipple stops the activity and the hair stays in the scalp.
  • Talogen can be divided into generators, which are the periods when hair papilla starts to work or develops new hair, causing the old hair to become bald.
  • the hair growth period is 3 to 5 years for men, 4 to 6 years for women, 30 to 45 days for log degeneration, 3 to 4 months for rest periods, and hair loss naturally occurs.
  • the generator from which the hair is produced starts.
  • Hair loss is normal or normal, while hair with a lot of hair growth is normal. Hair loss (Alopecia) usually shows hair loss with a lot of resting hair.
  • Hair loss is characterized by the miniaturization of the hair. As hair loss progresses, the period of growth is shorter, which leads to smaller and smaller hairs. Thus, hair loss can be quickly transferred to the growing hair follicle for the treatment of hair loss. It is important to increase the shortened growth period.
  • Alpha-reductase azepin a more powerful hormone by the enzyme of (a _ re ductase)
  • DHT Dihydrotestosterone
  • Alopecia areata is caused by autoimmune diseases, mental stress, or genetic predisposition.
  • Alopecia or ovarian alopecia occurs, characterized by the appearance of ringworm or hair growth. This is caused by alopecia areata, which is fundamentally different from androgenetic alopecia, and the treatment is also different from that used to treat corticosteroids. Alternatively, apply minoxidil to the affected area or artificially cause irritation in the affected area.
  • the active ingredients in the product are for the purpose of promoting blood circulation, inhibiting male hormone action, strengthening of hair root function, etc., but they are sold as products in the market. However, there are no significant effects yet. Problems are also raised.
  • Minoxidil of U.S. Patent No. 3,382,247 which is known to exhibit a hair growth effect by side effects among patients who use it, has been approved by the US Food and Drug Administration (FDA) as a raw material for hair growth, and is currently used for hair growth treatment.
  • FDA US Food and Drug Administration
  • Merck's finasteride mentioned in US Pat. No. 5,215,894, was originally used as a treatment for men's prostates, but was also used as a treatment for male alopecia by controlling the dose in the human body.
  • the present invention has been completed to stimulate hair growth factor factors with new compounds that prevent signs, to promote hair growth, to promote hair growth, to delay hair loss, and to provide an external preparation for hair loss prevention and hair promotion with hair growth effects. .
  • the present invention is not intended to be harmful to the human body, has no side effects, and further skin It provides a composition with excellent hair growth and hair growth effect while preventing drying and skin aging.
  • the composition according to the present invention is a composition for promoting hair growth or preventing hair loss, and a composition for promoting hair growth or preventing hair loss, containing a derivative represented by the following formula (1), a pharmaceutically acceptable salt thereof, or a solvate thereof as an active ingredient.
  • a derivative represented by the following formula (1) a pharmaceutically acceptable salt thereof, or a solvate thereof as an active ingredient.
  • R 2 is hydrogen, straight or branched chain (C7-C30) alkyl, (C7-C30) alkenyl or (C7-C30) alkynyl, the alkyl, alkenyl or alkynyl is hydroxy, Carbonyl, (C7-C30) aryl, (C7-C30) aryloxy, (C1-C30) alkylamino, di (C1-C30) alkylamino or amino (C1-C30) alkyl.
  • composition according to one embodiment of the present invention a composition for promoting hair growth prevention or hair loss is characterized in that the sum of the carbon number of the above and R 2 is 4 to 50.
  • Chemical Formula 1 illustrates a composition for promoting hair growth or preventing hair loss, which is selected from the following compounds.
  • composition of the present invention is a pyrimidine oxide derivative or pharmaceutically
  • a hair growth promoting or hair loss preventing composition further comprising an acceptable salt.
  • composition according to an embodiment of the present invention may be a composition characterized in that the compound represented by the formula (1) and the pyrimidine oxide derivative 1: 1: 0.1 to 10 contained.
  • a composition according to an embodiment of the present invention may contain 0.01 to 10% by weight of active ingredient.
  • composition according to the embodiment of the present invention may be a pharmaceutical composition or a cosmetic composition.
  • a composition according to an embodiment of the present invention is an external skin preparation including a solution, a cream, an ointment, a paste, an aerosol, a gel or a wax, or a hair in a shampoo, rinse, ampoule or treatment type. It may be an external preparation.
  • composition according to the present invention provides a new compound with pyrimidine oxide derivatives.
  • FIG. 1 is a view showing the hair growth promoting effect of the hair growth composition prepared according to an embodiment of the present invention, a mouse hair growth observation picture,
  • FIG. 2 is a view showing the skin barrier damage alleviation effect of the hair growth composition prepared according to an embodiment of the present invention.
  • the present applicant contains a novel active compound containing a pyrimidine oxide derivative as a complex active ingredient.
  • the present invention was completed by remarkably promoting the hair growth and using the composition to prevent hair loss.
  • the composition according to the present invention is a composition for promoting hair growth or preventing hair loss, and contains an derivative represented by the following formula (1), a pharmaceutically acceptable salt thereof, or a solvate thereof as an active ingredient.
  • R 2 is hydrogen, straight or branched chain (C 7 -C 30) alkyl, (C 7 -C 30) alkenyl or (C 7 -C 30) alkynyl, and the alkyl, alkenyl or alkynyl is hydroxy, Carbonyl, (C7-C30) aryl, (C7-C30) aryloxy, (C1-C30) alkylamino, di (C1-C30) alkylamino or amino (C1-C30) alkyl.
  • R 2 is hydrogen, straight or branched chain (C 7 -C 30) alkyl, (C 7 -C 30) alkenyl having 1 or 2 double bonds or having 1 or 2 triple bonds ( C7-C30) may be alkynyl, but is not limited to this.
  • R ! And R The sum of the carbon number of the above and 3 ⁇ 4 is preferably 4 to 50, more preferably 30 to 40, but not limited to this.
  • Formula 1 of the present invention is selected from the following compounds
  • the composition may be a hair growth promoting or hair loss preventing composition further comprising a hair growth promoting ingredient.
  • the hair growth promoting component may be pyrimidine oxide derivative or its
  • the pyrimidine oxide derivative is used as a hair growth promoting ingredient.
  • a composition containing such a pyrimidine oxide derivative as a compound of Formula 1, which is a novel compound of the present invention. Can be provided.
  • a composition comprising the compound represented by Chemical Formula 1 and the pyrimidine oxide derivative not only helps to stimulate hair growth factors of dermal papilla cells or hair cells, but also helps to produce hair shaft. Particularly in the bulge, where hair growth occurs under the dermis, the pyrimidine oxide derivative can be retained or stayed for a long time, which can have a remarkable effect on hair growth, which can have synergistic effects on promoting hair growth or preventing hair loss.
  • the hair growth promoting effect can be significantly increased than when used alone.
  • the pyrimidine oxide derivatives used in the present invention are not particularly limited, but are represented by the following Chemical Formula 2.
  • the hair growth effect may be greatest when provided as a pharmaceutical composition, cosmetic composition, or quasi-drug composition, including in the above range.
  • a derivative of Compound 1 may be prepared by adding oleic acid, palmitic acid or stearic acid, and more preferably.
  • a pharmaceutical composition containing the derivative of Compound 1 as an active ingredient prepared by adding oleic acid It may be most effective when provided as a cosmetic or quasi-drug composition.
  • composition according to the embodiment of the present invention may be a pharmaceutical composition, a cosmetic composition or
  • the composition according to one embodiment of the present invention may be an external skin preparation or an external hair preparation, and the external skin preparation may be in the form of a solution, cream, ointment, paste, aerosol, gel or wax.
  • the topical hair formulation may comprise a shampoo, rinse, dye or treatment form.
  • the skin may include all the cuticles with hair and hair follicles throughout the body, including the scalp, jaw, armpits, ears, cheeks, and eyebrows. May contain hair throughout the body, including eyelashes and eyelashes), whiskers, armpits, etc., where the external agent may mean that the composition is applied or spread directly on the epidermis or hair. May contain cuticles or hairs from any mammal.
  • composition according to an embodiment of the present invention the substance corresponding to the formula 1 and the pyrimidine oxide derivative weight
  • composition according to an embodiment of the present invention is a pharmaceutical composition
  • the derivative represented by Chemical Formula 1 may be in the form of a pharmaceutically acceptable salt
  • the pharmaceutically acceptable salt may be conventionally used in the art. Salts prepared according to the method may mean. 1
  • pharmaceutically acceptable salts may include, but are not limited to, salts derived from pharmacologically or physiologically acceptable inorganic acids and organic acids and bases. .
  • composition according to the embodiment of the present invention is a pharmaceutical composition
  • the composition according to the embodiment of the present invention is a pharmaceutical composition
  • Pharmaceutically acceptable carriers and / or excipients may be used.
  • the pharmaceutically acceptable carriers may be conventionally used in the manufacture of pharmaceutical compositions.
  • the carriers and / or excipients may include binders, lubricants, disintegrants, Examples include one or more selected from the group consisting of lubricants, coatings, emulsifiers, suspending agents, solvents, stabilizers, absorption aids, injectable waters and tonic agents.
  • layering agents In addition, layering agents, anticoagulants, lubricants, wetting agents, fragrances It may further contain emulsifiers or preservatives, wherein the formulation may be in the form of granules, powders, solutions, creams, ointments, aerosols, pastes, gels or waxes, and the solution is not only in the state in which the active ingredient is dissolved in the solvent. Suspension or Emulsion status may also be included.
  • the appropriate dosage of the composition may vary depending on the condition and weight of the object to be coated, the degree of the disease, the formulation of the composition, the path of application, and the duration of the composition.
  • the derivative of the pyrimidine oxide derivative represented by the formula (1) represented by the formula (1)
  • the active ingredient, a compound of these compounds, is an adult basis, and one application can be used to apply 20 ⁇ 1 / ⁇ 2 of composition per unit area of the skin from which hair is removed, but not limited thereto.
  • the coating may be carried out once to six times a day, and at least two times a day.
  • Each application can be done at the same time intervals, but not particularly limited.
  • composition of the present invention is a cosmetic composition or a quasi-drug composition
  • the composition is a derivative of the derivative and pyrimidine oxide derivative represented by the above formula (1).
  • Adjuvants commonly used in cosmetic compositions or quasi-drug compositions such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic active agents, preservatives, antioxidants, solvents, fragrances, layering agents, barrier agents, pigments, odorants, dyes or mixtures thereof May contain
  • composition of the present invention when it is a cosmetic composition or a quasi-drug composition, it may be used as a cosmetic or quasi-drug formulation.
  • the quasi-drug preparation may be in the form of granules, powders, solutions, creams, ointments, aerosols, pastes, gels or waxes.
  • the solution may contain not only a state in which the active ingredient is dissolved in the solvent, but also a suspension or emulsion.
  • composition according to an embodiment of the present invention may contain various components which are blended in the conventional hair loss preventing or hair regrowth composition according to the above-described various formulations or suitable for the final purpose.
  • Formulations may contain one or more of detergents, preservatives, preservatives, thickeners, viscosity modifiers, pH adjusters, flavorings, dyes, hair conditioning agents and water.
  • Various conventional ingredients, which are formulated into conventional hair loss prevention or hair regrowth compositions suited for the end purpose, are well known to those skilled in the art.
  • the composition may be a hair growth promoting or hair loss preventing composition containing 0.01 to 10% by weight of an active ingredient. Preferably, one to three times a day may be applied to obtain a remarkable hair growth effect. It may contain 0.01 to 8% by weight, more preferably 0.01 to 6% by weight of active ingredient.
  • composition according to an embodiment of the present invention may further contain glycol, lower alcohol of C1-C5, and water, but is not particularly limited.
  • Lower alcohols of C1-C5 Silver may be a solvent of the active substance and may be one or more selected from methane, ethane, acetone, isopropyl alcohol and n-butanol. Such lower alcohols may have excellent volatility upon application of the composition to enhance the feeling, and in particular, ethanol is more volatile and more harmless to humans.
  • composition according to one embodiment of the present invention may contain 5 to 20 parts by weight of glycol, 4 to 15 parts by weight of lower alcohol and 1 to 10 parts by weight of water based on 1 part by weight of the active ingredient.
  • the weight ratio of the standard glycol, lower alcohol, and water inhibits the skin irritation during application without compromising hair regrowth effect, secures the use time required for uniform application, and has a refreshing feeling by proper volatilization, and absorbs effective substance. It is a range that can be promoted.
  • 1,3-diamino-2-propanol (l, 3-Diamino-2-propanol, 3.99g, 44.25mmol, sigma-aldrich) edichloromethane (DCM, 500ml, Samjeon Pure Chemicals) and triethylamine (TEA, 24.7 10 minutes after the reaction, EDC-HCl (25.45 g, 132.76 mmol, sigma-aldrich) and HOBt (17.9 g, 132.76 mmol, sigma-aldrich) were added. , Oleic acid (25.0g, 88.51mmol, sigma-aldrich) was added and stirred at room temperature for 4 hours.
  • composition was prepared using the active ingredient. Specifically, 1 wt% of '056N', pyrrolidinyldiaminopyrimidine
  • mice were used as experimental animals.
  • C57BL / 6 mice are degenerated hairs from 6 weeks of age, dormant from 7 weeks of age, and have a characteristic cycle of returning to growth after 12 weeks of age. Animal models most frequently used for hair growth testing. to be.
  • C89BL / 6 mice 6 weeks old, were purchased, tested at 23 ⁇ 3 ° C, 10% relative humidity 55 ° C, and 12 hours of lighting time for 1 week of redness and at 7 weeks of age.
  • the mouse was placed in a desiccator containing ether and anesthetized for 1 minute, and then the hair of the mouse was removed using a hair remover. After 1 day, the hair-repellent composition prepared in Preparation Example 1 was applied to the mouse which had no wound on the back.
  • the application of the prepared hair-repellent composition was performed once a day, and the coating amount was applied to the skin from which hair was removed once the composition of 20 ⁇ 1 / ⁇ 2 was applied to the coating.
  • Figure 1 shows the mouse just before the experiment (left photo) and the point of application for eight weeks.
  • Figure 1 (a) shows the vehicle with the vehicle observed.
  • FIG. 1 shows the hair growth composition prepared in Example 1.
  • Fig. 1 shows that the hair growth composition according to the present invention has extremely high hair growth activity.
  • trans-dermal water loss (TEWL) was measured to maintain almost no difference, and in Example 1 containing 0.5% by weight of 056N as an active ingredient.
  • composition of the present invention can be confirmed to be effective in skin barrier recovery.

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

Abstract

본 발명은 발모촉진용 또는 탈모방지용 조성물에 관한 것으로, 상세하게, 피부에 대한 안정성이 우수하고 부작용이 없으며, 모발 성장을 촉진하고 탈모를 지연시켜 탈모를 방지할 수 있으며 발모 효과가 우수한 조성물에 관한 것이다.

Description

명세서
발명의명칭:발모촉진용또는탈모방지용조성물 기술분야
[1] 본발명은발모촉진용또는탈모방지용조성물에관한것으로,상세하게， 피부에대한안정성이우수하고부작용이없으며，모발성장을촉진하고탈모를 지연시켜탈모를방지할수있으며발모효과가우수한조성물에관한것이다. 배경기술
[2] 탈모는유전적요인이가장주요한원인으로작용하나，최근사회적
스트레스의증가와더블어환경오염및인스턴트식품등서구화된식습관，잦은 파마와염색,잘못된두피관리들로인하여탈모인구가점차증가하고있다.
[3] 모발은성장기 (Anagen),퇴화기 (Catagen),휴지기 (Telogen)의주기를돌며
발모와탈모를반복하며유지되고있다.상세하게는，모발을성장시키는 성장기 (anagen),성장을종료하고모구부가축소하는시기인퇴화기 (catagen), 모유두가활동을멈추고모발을두피에머무르게하는시기인휴지기 (talogen), 모유두가활동을시작하거나또는새로운모발을발생시켜오래된모발을 탈모시키는시기인발생기로나눌수있다.
[4] 모발의성장기는남성 3~5년，여성이 4~6년정도로그후퇴화기 30~45일정도， 휴지기가 3~4개월정도지나자연적으로탈모가된다.그리고휴지기의 마지막이되면새로운모발이생성되는발생기가시작된다.
[5] 탈모는정상적인현상이나정상인사람이성장기상태의모발이많은데비해 보통탈모증 (Alopecia)인사람은휴지기상태의모발이많아눈으로보이는 탈모현상이나타내게된다.
[6] 탈모증을나타내는사람들의특징은모발의소형화에있다.탈모가진행될수록 성장기의기간이짧아지고이로인하여모발은점점소형화된다.따라서탈모의 치료를위해서는휴지기상태의모낭을성장기로빨리갈수있도록하고,짧아진 성장기를늘려주는것이중요하다.
[7] 남성형탈모증은남성의성징을나타나게하며사춘기에근육의발달，남성 기관의발달등에작용하는호르몬인테스토스테론 (Testosterone)이라는 남성호르몬에의해나타나는현상으로이테스토스테론이 5
알파 -리덕타아제 (a_reductase)라는효소에의해더강력한호르몬인
디히드로테스토스테로 (Dihydrotestosterone:DHT)으로바뀌게되면，이호르몬이 모낭에작용하여모낭을성장기단계에서퇴화기단계로유도하여탈모가 일어나게한다.따라서이러한원인에의한탈모증을치료하기위하여 5 알파-리덕타아제에의한 DHT의생성을억제하는방법이주로사용된다.
[8] 여성형탈모증은주로폐경기이후에스트로겐양의감소에의해발생한다. 여성의탈모증은남성형탈모증의모양과는좀다르게머리앞부분은빠지지 않고중간부분의머리만이주로탈모된다.여성의탈모증은 5
알파-리덕타아제와의연관관계가남성보다적게작용한다.따라서 5 알파-리덕타아제를억제시키는약물은폐경기이후의탈모증여성에게는별로 효과가없다.따라서，이러한탈모증을위한치료제로는주로미녹시딜이나 에스트로겐을사용한다.
[9] 원형탈모증은자가면역질환이나정신적스트레스,유전적소인에의해
발생한다.원형또는난원형의탈모가일어나며，두부백선이나발모벽이생기는 특징을갖고있다.이러한원형탈모증은안드로겐성탈모증과는근본적으로 원인이다르며，치료법또한달라서부신피질호르몬제를처리하는방법을 사용하거나，미녹시딜을환부에바르거나인위적으로환부에자극을유발하는 방법을사용한다.
[10] 이처럼다양하고복잡한탈모원인에대하여，현재까지알려진탈모방지
제품에는유효성분으로혈액순환촉진,남성호르몬작용억제，모근기능강화 등을목적으로하는성분등이시중에제품으로판매되고있으나，효과면에서 뚜렷한효과를지닌것은아직까지없는상태이고,대부분부작용의문제가 제기되기도한다.
[11] 이러한발모제로，처음에는혈액순환촉진을위한용도로개발되어
사용되다가이를사용하는환자들사이에서부작용으로발모효과를나타내는 것으로알려져，이후，발모용원료로미국식품의약품안전청 (FDA)에서승인받아 발모치료제로사용되어진미국특허제 3,382,247호의미녹시딜은현재에도 발모용치료제로사용되고있으며，미국특허제 5,215,894호에서언급된 머크사의피나스테라이드 (finasteride)는처음에는남성의전립선치료제로 사용되던성분이었으나，역시인체내투여량을조절하여남성형탈모증 치료제로탄생하게되었다.
[12] 그러나，미녹시딜의경우끈적이는사용감과피부에자극을유발하는부작용이 보고된바있으며,피나스테라이드의경우현재경구투여용제제로사용되고 있으나,이의섭취에따라성기능장애둥의부작용이보고된일도있을뿐 아니라,탈모에대해서도꾸준한복용이이루어져야만효과가있으며,이들의 5 알파 -리덕타아제활성억제제는도포에의한효과를기대하기어렵고, 경구복용에의해서만효과를기대할수있어서사용상에많은불편함이있다.
[13] 이상과같은문제점에착안하여 ,본발명자들은피부손상및피부노화의
징후를방지하는신규화합물에의해발모성자인자들을자극하여모간을 생성하고,모발성장을촉진하고，탈모를지연시켜，발모효과를갖는탈모방지 및발모촉진용외용제조성물을제공하고자본발명을완성하였다.
발명의상세한설명
기술적과제
[14] 본발명은목적은인체에해롭지아니하고，부작용이없으며，나아가피부 건조와피부노화를방지하면서도,발모및육모효과가우수한조성물을 제공하는것이다.
과제해결수단
[15] 본발명에따른조성물은발모촉진또는탈모방지용조성물이며,하기화학식 1로표시되는유도체，이들의약학적으로허용가능한염，또는이들의 용매화물을유효성분으로함유하는발모촉진또는탈모방지용조성물을 제공한다.
Figure imgf000004_0001
[18] (상기화학식 1에서，
[19] 상기 및 R2는수소,직쇄또는분지쇄 (C7-C30)알킬， (C7-C30)알케닐또는 (C7-C30)알키닐이며,상기알킬，알케닐또는알키닐은하이드록시,카보닐， (C7-C30)아릴， (C7-C30)아릴옥시， (C1-C30)알킬아미노,디 (C1-C30)알킬아미노 또는아미노 (C1-C30)알킬로더치환될수있다.)
[20] 본발명의일실시예에따른조성물에있어，상기 및 R2의탄소수의합이 4 내지 50인것을특징으로하는발모촉진또는탈모방지용조성물을예시한다.
[21] 본발명의일실시예에상기화학식 1은하기화합물로부터선택되는것을 특징으로하는발모촉진또는탈모방지용조성물을예시한다.
Figure imgf000005_0001
660ZTO/SlOZaM/X3d 09TS80/910Z OAV
Figure imgf000006_0001
[26] 본발명의조성물은피리미딘옥사이드유도체또는그의약학적으로
허용가능한염을더포함하는발모촉진또는탈모방지용조성물을제공한다.
[27] 본발명의일실시예에따른조성물의상기피리미딘옥사이드유도체는
6- (피페리니딜) -2,4-피리미딘디아민 -3-옥사이드 (6-(piperidinyl)-2,4,-pyrimidinedia mine-3 -oxide)또는
2，4-디아미노 -6-피를리디노-피리미딘 -3-옥사이드 (2,4-diamino-6-pyrrolidino-pyrim idine-3-oxide)에서선택되는어느하나또는둘인것을특징으로하는조성물올 예시한다.
[28] 본발명의일예에따른조성물은상기화학식 1로표시되는화합물과상기 피리미딘옥사이드유도체가 1 : 0.1내지 10으로포함되는것을특징으로하는 조성물일수있다.
[29] 본발명의일실시예에따른조성물은 0.01 - 10증량 %의유효성분을함유할수 있다.
[30] 본발명의일실시예에따른조성물은약학적조성물또는화장료조성물일수 있다.
[31] 본발명의일실시예에따른조성물은용액제,크림제,연고제,페이스트, 에어로솔제，겔제또는왁스제형태를포함하는피부외용제제형이거나,샴푸, 린스,앰플또는트리트먼트형태의모발외용제제형일수있다.
발명의효과
[32] 본발명에따른조성물은신규화합물에피리미딘옥사이드유도체를더
포함하는복합유효성분으로함유함으로써，일일사용하여도，인체에해롭지 아니하며，부작용이없으며，장기간지속적으로사용가능하고，모발의성장을 현저하게촉진시켜우수한발모또는탈모방지효과를가지며，나아가발모 촉진과함께염증완화효과를갖는특징이있다.
도면의간단한설명
[33] 도 1은본발명의일실시예에따라제조된발모조성물의발모촉진효과를 보여주는도면으로，마우스털성장관찰사진이며,
[34] 도 2는본발명의일실시예에따라제조된발모조성물의피부장벽손상완화 효과를보여주는도면이다.
발명의실시를위한최선의형태
[35] 이하첨부한도면들을참조하여본발명에따른조성물을상세히설명한다. 이때，사용되는기술용어및과학용어에있어서다른정의가없다면,이발명이 속하는기술분야에서통상의지식을가진자가통상적으로이해하고있는 의미를가지며,하기의설명및첨부도면에서본발명의요지를불필요하게 흐릴수있는공지기능및구성에대한설명은생략한다.
[36] 본출원인은인체에무해하며,부작용이없고，발모효과가우수한물질에대해 연구를거듭한결과，본출원인이개발한신규한화합물에피리미딘옥사이드 유도체를더포함하는복합유효성분으로함유하는조성물을사용함으로써 발모를현저히촉진시키고탈모방지에효과가있음을발견하여본발명을 완성하였다.
[37] 본발명에따른조성물은발모촉진또는탈모방지용조성물이며，하기화학식 1로표시되는유도체，이들의약학적으로허용가능한염，또는이들의 용매화물을유효성분으로함유한다.
[38] [화학식 1]
Figure imgf000007_0001
[40] (상기화학식 1에서,
[41] 상기 및 R2는수소，직쇄또는분지쇄 (C7-C30)알킬, (C7-C30)알케닐또는 (C7-C30)알키닐이며,상기알킬，알케닐또는알키닐은하이드록시，카보닐， (C7-C30)아릴， (C7-C30)아릴옥시， (C1-C30)알킬아미노，디 (C1-C30)알킬아미노 또는아미노 (C1-C30)알킬로더치환될수있다.)
[42] 바람직하게는，상기 및 R2는수소，직쇄또는분지쇄 (C7-C30)알킬, 1또는 2개의이중결합을갖는 (C7-C30)알케닐또는 1또는 2개의삼중결합을갖는 (C7-C30)알키닐인것일수있으나이에한정하는것은아니다. [43] 또한，본발명의일예로써상기화학식 1로표시되는유도체에서상기 R!및 R: 은상기 및 ¾의탄소수의합이 4내지 50인것이바람직하며, 30내지 40인 것이더욱바람직하나이에한정하는것은아니다.
[44] 본발명의상기화학식 1은예를들자면，하기화합물로부터선택되는것이
Figure imgf000008_0001
Figure imgf000009_0001
Figure imgf000009_0002
[49] 본발명은또다른특징으로상기조성물은모발성장촉진성분을더포함하는 발모촉진또는탈모방지용조성물일수있다.
[50] 상기모발성장촉진성분으로는피리미딘옥사이드유도체또는그의
약학적으로허용가능한염일수있으나특별히제한하는것은아니다.
[51] 상기피리미딘옥사이드유도체는모발성장촉진성분으로사용시
세포수준에서모낭모유두세포의증식을촉진하고모낭주위의혈류를 증가시켜모발성장촉진의효과를가진다.이러한피리미딘옥사이드유도체를 본발명의신규한화합물인상기화학식 1과복합유효성분으로함유하는 조성물을제공할수있다.
[52] 본발명에따른상기화학식 1로표시되는화합물과상기피리미딘옥사이드 유도체를흔합한조성물은모유두세포또는모모세포의발모성장인자를 자극하여모간을생성하는데도움을줄뿐만아니라，상기조성물이진피 하부에체류하여모발의성장이이루어지는모구부주위 (Bulb)에서특히， 피리미딘옥사이드유도체가장시간유지또는체류되어발모성장에현저한 효과를줄수있어，발모촉진또는탈모예방에시너지효과를가질수있다.
[53] 따라서，본발명에따른일실시예에따른상기조성물에서상기화학식 1의 화합물이상기피리미딘옥사이드유도체와함께사용하는경우，각각단독으로 사용할때보다모발성장촉진효과가현저히증가할수있다.
[54] 본발명에서사용하는피리미딘옥사이드유도체는특별히제한하는것은 아니나，하기화학식 2로표시되는
6- (피페리니딜) -2,4-피리미딘디아민 -3-옥사이드 (6-(piperidinyl)-2,4,-pyrimidinedia mine-3-oxide)또는하기화학식 3으로표시되는
2,4-디아미노 -6-피롤리디노-피리미딘 -3-옥사이드 (2,4-diamino-6-pyrrolidino-pyrim idine-3-oxide)에서선택되는어느하나또는둘인것이발모를극히현저하게 증진시킬수있어보다좋다.
[55] [화학식 2]
Figure imgf000010_0001
[58]
Figure imgf000011_0001
[60] 나아가，유효물질로피리미딘옥사이드유도체증
6- (피페리니딜) -2,4-피리미딘디아민 -3-옥사이드 (6-(piperidinyl)-2,4,-pyrimidinedia mine-3-oxide)또는
2,4-디아미노 -6-피롤리디노-피리미딘 -3-옥사이드 (2,4-diamin으 6-pyrrolidino-pyrim idine-3-oxide)의염또는이들의흔합물올포함하는경우,염증억제효과를얻을 수있어보다좋다.
[61] 본발명의일예로써상기화학식 1로표시되는유도체와상기피리미딘
옥사이드유도체가 1 : 0.1내지 10으로포함되는것을특징으로하는발모촉진 또는탈모방지용조성물을제공할수있으나이에한정하는것은아니다.
[62] 상기범위로포함하여약학적조성물，화장료조성물또는의약외품조성물로 제공할때발모효과가가장뛰어날수있다.
[63] 본발명에따른일실시예에따른상기조성물에함유되는유효성분인상기 화학식 1로표시되는유도체의제조방법으로는，
1,3-디아미노ᅳ 2-프로판올 (l,3-Diammo-2-propanol),디클로로메탄 (DCM)및 트리에틸아민 (triethylamine)을함유하는반웅액을 5내지 -5°C로감온한후， 올레산,팔미트산또는스테아르산올첨가하여상온에서 3내지 5시간동안 교반하는단계，교반이완료된반웅액에물과디클로로메탄 (DCM)을넣고교반, 정치후층분리하여유기층을세척및건조하는단계，건조하여얻은잔여물을 재결정화하여흰색의고체화합물로수득되는생성물일수있다.상기화합물 1의제조방법에서올레산，팔미트산또는스테아르산을첨가하여화합물 1의 유도체를제조할수있으며，보다바람직하게는,을레산 (oleic acid)를첨가하여 제조한상기화합물 1의유도체를유효성분으로함유하는약학적조성물, 화장료조성물또는의약외품조성물로제공할때가장효과적일수있다.
[64] 본발명의일실시예에따른조성물은약학적조성물,화장료조성물또는
의약외품조성물로제공될수있다.
[65] 그제형에있어，본발명의일실시예에따른조성물은피부외용제제형또는 모발외용제제형일수있고,피부외용제제형은용액제，크림제,연고제， 페이스트,에어로솔제，겔제또는왁스제형태를포함할수있으며，모발외용제 제형은샴푸，린스,염플또는트리트먼트형태를포함할수있다.
[66] 피부외용제제형인경우,피부는두피，턱，겨드랑이,귀밑,볼，눈썹등신체 전반에모근및모낭이있는모든표피를포함할수있다.모발외용제제형인 경우,모발은머리카락，눈썹 (속눈썹및겉눈썹올포함함)，수염，겨드랑이등신체 전반에있는털을포함할수있다.이때,외용제라함은조성물이표피또는털에 직접도포또는산포되는것을의미할수있다.이때,표피또는털은인간올 포함한포유류의표피또는털을포함할수있다.
[67] 본발명의일실시예에따른조성물에있어，상기화학식 1에해당하는물질과 피리미딘옥사이드유도체중
6- (피페리니딜) -2,4-피리미딘디아민 -3-옥사이드 (6-(piperidinyl)-2,4,-pyrimidinedia mine-3-oxide)또는
2,4-디아미노 -6-피롤리디노-피리미딘 -3-옥사이드 (2,4-diamino-6-pyrrolidino-pyrim idine-3-oxide)를함유한복합유효성분，상기화학식 1의유도체，상기화학식 1의 염또는이들의흔합물을포함할수있으며,이들의유도체또는이들의염은 발모를극히현저하게증진시킬수있어보다좋다.나아가，이들의흔합물을 • 포함하는경우，손상된피부장벽회복효과를얻을수있어보다좋다.이때，상기 화학식 1로표시되는유도체는염의형태일수있다.
[68] 본발명의일실시예에따른조성물이약학적조성물인경우,상기화학식 1로 표시되는유도체는약학적으로허용되는염의형태일수있고，약학적으로허용 가능한염은당해기술분야에서통상적인방법에따라제조된염을의미할수 ᅳ 있다.구1체적으로，약학적으로허용가능한염은약리학적또는생리학적으로 허용되는무기산과유기산및염기로부터유도된염을포함할수있으나，이로 한정되지는않는다.
[69] 본발명의일실시예에따른조성물이약학적조성물인경우，조성물은
약학적으로허용되는담체및 /또는부형제를포함할수있다.약학적으로 허용되는담체는약학적조성물제조시에통상적으로이용되는것이면 무방하다.담체및 /또는부형제로는결합제,활택제，붕괴제，윤활제,피복제, 유화제，현탁제，용제,안정화제，흡수조제，주사용수및둥장화제로이루어진 군으로부터선택된하나이상을예로들수있다.또한，층진제，항웅집제， 윤활제,습윤제,향료，유화제또는방부제등을추가로포함할수있다.이때, 제형은과립,분말，용액,크림,연고，에어로솔,페이스트,겔또는왁스등의 형태일수있고，용액은유효성분이용매에용해된상태뿐만아니라,현탁액이나 에멀젼상태또한포함할수있다.
[70] 본발명의일실시예에따른조성물이약학적조성물인경우，조성물의적합한 도포량은도포대상의상태및체중，질병의정도,조성물의제형，도포경로및 기간에따라다를수있다.본발명의일실시예에따른조성물에있어상기 화학식 1로표시되는유도체에피리미딘옥사이드유도체중
6- (피페리니딜) -2,4-피리미딘디아민 -3-옥사이드 (6-(piperidinyl)-2,4,-pyrimidinedia mine-3-oxide),
2,4-디아미노 -6-피를리디노-피리미딘 -3-옥사이드 (2,4-diamino-6-pyrrolidino-pyrim idine-3-oxide)또는이들의혼합물을함유한복합유효성분또는이들의 흔합물인유효성분은성인기준으로，1회도포시도포량은털이제거된피부의 단위면적당 20μ1/αη2의조성물이도포되도록사용할수있으나이에한정하는 것은아니다.
[71] 상기도포는하루에 1회내지 6회로이루어질수있고，하루에 2회이상의
도포가이루어지는경우각도포는동일시간간격으로이루어질수있으나 특별히제한하는것은아니다.
[72] 본발명의조성물이화장료조성물또는의약외품조성물인경우，조성물은 상기화학식 1로표시되는유도체와피리미딘옥사이드유도체중
6- (피페리니딜) -2,4-피리미딘디아민 -3-옥사이드 (6-(piperidinyl)-2,4,-pyrimidinedia mine-3-oxide),
2，4-디아미노 -6-피를리디노-피리미딘 -3-옥사이드 (2,4-diamino-6-pyrrolidino-pyrim idine-3-oxide)또는이들의흔합물를함유한복합유효성분이외에,화장료 조성물이나의약외품조성물에통상적으로이용되는보조제예컨대친수성이나 친지성겔화제，친수성이나친지성활성제，보존제，항산화제,용매，방향제, 층전제，차단제，안료，흡취제，염료또는이들의혼합물을함유할수있다.
[73] 본발명의조성물이화장료조성물또는의약외품조성물인경우,화장품또는 의약외품의제형으로사용될수있다.의약외품제형은과립，분말,용액,크림， 연고，에어로솔，페이스트,겔또는왁스등의형태일수있고,용액은유효성분이 용매에용해된상태뿐만아니라,현탁액이나에멀견상태또한포함할수있다. 화장품또는의약외품의제형으로，헤어토닉,헤어크림,헤어로션，해어샴푸, 헤어린스,해어컨디셔너，해어스프레이 ,해어에어졸，포마드，분말,젤,해어팩， 헤어트리트먼트，눈썹발모제,속눈썹발모제，속눈썹영양제，또는애완동물용 샴푸및애완동물용린스둥과같이용액,솔젤，에멀젼,오일,왁스，에어졸둥 다양한형태일수있으나，이돌로제한되는것은아니다.
[74] 또한，본발명의일실시예에따른조성물은상술한각종제형에따라또는 최종목적에적합하게통상의탈모방지또는발모용조성물에배합되는각종 성분들을함유할수있다ᅳ일예로,샴푸의제형을갖는경우에는세정성분인 합성계면활성제와방부제，점증제，점도조절제， pH조절제,향료，염료,모발 컨디셔닝제및물중어느하나이상을함유할수있다.각종제형에따라또는 최종목적에적합하게통상의탈모방지또는발모용조성물에배합되는 통상적인각종성분들은당해분야의전문가에게널리공지되어있다.
[75] 본발명의일실시예에따른상기조성물은 0.01 - 10중량 %의유효성분으로 함유하는발모촉진또는탈모방지용조성물일수있다.좋게는 1일 1내지 3회의 도포로,현저한발모효과를얻기위해서 0.01내지 8증량 %，보다좋게는 0.01 내지 6증량 %의유효성분을함유할수있다.
[76] 본발명의일실시예에따른조성물은글리콜, C1-C5의저급알코을및물을더 함유할수있으나특별히한정하는것은아니다.상기글리콜은
폴리에틸렌글리콜,폴리프로필렌글리콜및폴리에틸렌프로필렌글리콜에서 하나또는둘이상선택되는물질일수있다.이러한글리콜은페이스트,크림 또는겔과같은제형으로제조가능하게하며보습력을향상시킬수있다.상기 C1-C5의저급알코올은유효물질의용매일수있으며，메탄을,에탄을，아세톤， 이소프로필알코올및 n-부탄올에서하나또는둘이상선택되는물질일수있다. 이러한상기저급알코을은조성물의도포시휘발성이우수하여사용감을 증진시킬수있으며,특히에탄올은휘발성이우수하면서도인체에무해하여 보다바람직하다.
[77] 본발명의일실시예에따른조성물은유효성분 1중량부를기준으로， 5내지 20 중량부의글리콜， 4내지 15중량부의저급알코올및 1내지 10중량부의물을 함유할수있다.이러한유효성분기준，글리콜，저급알코올및물의중량비율은 발모효과를저해하지않으면서도도포시피부자극을억제하고균일한도포에 필요한사용시간올확보하면서도적절한휘발에의해청량한사용감을가지며， 유효물질의흡수를촉진할수있는범위이다.
[78]
[79]
Figure imgf000014_0001
1,3-디아미노 -2-프로판올 (l,3-Diamino-2-propanol, 3.99g, 44.25mmol, sigma-aldrich)에디클로로메탄 (DCM, 500ml,삼전순약)과트리에틸아민 (TEA, 24.7ml,삼전순약)을투입하여반웅액을만들었다.상은에서 10분후,반웅액에 EDC- HCl(25.45g, 132.76mmol, sigma-aldrich)), HOBt(17.9g, 132.76mmol, sigma-aldrich)), Oleic acid(25.0g, 88.51mmol, sigma-aldrich)를가한후실온에서 4시간동안교반하였다.교반후，상기반웅액에디클로로메탄 (DCM) 500ml,물 500ml를넣고교반，정치후층분리하였다.상기반웅액의모든유기층을진한 염산으로산성화하고 5분간교반한뒤포화염화수소수용액으로중화하였다. 유기층을모아브레인 (Brine, 150ml)으로세척하고황산마그네슴 (MgS04)으로 건조,여과한뒤여액을감압농축하였다.잔여물을메탄올 100ml로재결정하여 흰색의고체화합물 (23g,수율: 84%)올얻었다.수득된고체 (O56N'이라 명명한다)의 MS및 NMR결과는다음과같다.
[82] MS (ESI pos. ion) m/z: 620 (MH+). Ή NMR (600 MHz, CDC13)： 6.36 - 6.34 (m,
2H), 5.37 - 5.31 (m, 4H), 4.25 (br s, IH), 3.78 - 3.75 (m, IH), 3.38 - 3.27 (m, 4H), 2.22 (t, J = 7.8 Hz, 4H), 2.01 (q, J = 6.0 Hz, 8H), 1.68 - 1.60 (m, 5H), 1.33 - 1.27 (m, 39H), 0.88 (t, J = 7.2 Hz, 6H).
[83]
[84] (실시예 1)
[85] 제조예 1에서제조된 O56N'과피리미딘옥사이드유도체를함유한복합
유효성분을이용하여조성물을제조하였다.상세하게, '056Ν' 1중량 %, 피롤리디닐디아미노피리미딘
옥사이드 (2,4-디아미노 -6-피롤리디노-피리미딘 -3-옥사이드 (2,4-diamino-6-pyrroli dino-pyrimidine-3-oxide)(Kumar) 2증량 %，에탄올 60중량 %,
폴리프로필렌글리콜 (Mw=76.09) 37중량 «¾를혼합하여발모조성물을
제조하였다.
[86]
[87] 발모톡성평가
[88] 발모및육모효과에주로이용되는실험법인실험동물을이용한인-비보 (in vivo)평가를수행하였다.실험동물로 C57BL/6마우스를이용하였다. C57BL/6 마우스는출생후 6주령부터털이퇴화기로되며 , 7주령부터휴지기로되었다가 12주령이되면，다시성장기로돌아가는특징적인주기를갖는마우스로， 발모시험의용도로가장많이사용되는동물모델이다.
[89] 생후 6주된암컷 C57BL/6마우스를구매하였으며， 23± 3 °C,상대습도 55士 10% 및조명시간 12시간의사육조건에서 1주일간의적웅기를갖고, 7주령이되는 주에실험을실시하였다.마우스를에테르가들어있는데시케이터에넣고 1분간 마취시킨후，마우스의둥부분을제모기를이용하여털을제거하였다. 1일후 등부위에상처가없는마우스를대상으로제조예 1에서제조된발모조성물을 도포를하였다.제조된발모조성물의도포는 1일 1회수행되었으며, 1회도포시 도포량은털이제거된피부의단위면적당 20μ1/αη2의조성물이도포되도록 하였다.
[90] 이후, 1주일간격으로사진촬영을하여도포부위의색깔의변화를관찰하였다.
[91] 비교예로，비히클 (vehicle, PEG:EtOH=7:3)만을도포하였으며,발모조성물과 동일한양을 1일 1회도포하였다.
[92] 도 1은실험직전의마우스 (왼쪽사진)와 8주동안도포한시점의
마우스 (오른쪽사진)를관찰한도면으로，도 1(a)는비히클을도포한
후 (오른쪽)이며,도 1(b)는실시예 1로제조된발모조성물을도포한
후 (오른쪽)의결과이다.상기도 1의결과를통해，본발명에따른발모조성물이 극히높은발모활성을가짐을알수있다.
[93] 피부장벽손상회복시험 [94] 무모생쥐 (nude mouse)를이용하여피부장벽을손상시킨후본본발명에따른 조성물이피부장벽회복에영향을주는결과를얻기위하여본실험을 수행하였다.무모생쥐 (nude mouse)의좌，우표피의손상을주기위해
D-Squame을이용표피와손상을주었다.이때경피수분손실 (TEWL, trans epidermal water loss)을측정하여값의차이가거의없도록유지한후， 0.5 중량 %의 056N을유효성분으로포함하는실시예 1에서제조된발모조성물을 도포하였으며,비교예로는,비히클 (vehicle, PEG:EtOH=7:3)을발모조성물과 동일한양으로도포하였다.도포후， 3시간, 6시간경과후 TEWL(transepidermal water loss,수분의손실)을측정하여장벽회복능을측정하였다.측정결과 비히클만도포한마우스보다실시예 1에서제조된발모조성물을도포한 마우스에서장벽회복능이빠르게측정되었다.얻어진결과를도 2에
나타내었다.본발명의조성물은피부장벽회복에효과가있음을확인할수있는 결과이다.
[95] 이상과같이본발명에서는특정된사항들과한정된실시예및도면에의해 설명되었으나이는본발명의보다전반적인이해를돕기위해서제공된것일 뿐，본발명은상기의실시예에한정되는것은아니며，본발명이속하는 분야에서통상의지식을가진자라면이러한기재로부터다양한수정및변형이 가능하다.
[96] 따라서，본발명의사상은설명된실시예에국한되어정해져서는아니되며， 후술하는특허청구범위뿐아니라이특허청구범위와균등하거나등가적변형이 있는모든것들은본발명사상의범주에속한다고할것이다.

Claims

청구범위 [청구항 1] 하기화학식 1로표시되는유도체，이들의약학적으로허용가능한 염，또는이들의용매화물을유효성분으로함유하는발모촉진 또는탈모방지용조성물
[ 1]
Figure imgf000017_0001
(상기화학식 1에서，
상기 및 R2는수소，직쇄또는분지쇄 (C7-C30)알킬，
(C7-C30)알케닐또는 (C7-C30)알키닐이며，상기알킬,알케닐또는 알키닐은하이드록시,카보닐, (C1-C30)아릴, (C1-C30)아릴옥시,
(C1-C30)알킬아미노，디 (C1-C30)알킬아미노또는
아미노 (C1-C30)알킬로더치환될수있다 ·)
[청구항 2] 제 1항에있어서，
상기 및 R2의탄소수의합이 4내지 50인것을특징으로하는 발모촉진또는탈모방지용조성물.
[청구항 3] 제 1항에있어서，
상기화학식 1은하기화합물로부터선택되는것을특징으로하는 발모촉
또는탈모방지용조성물.
Figure imgf000018_0001
LI
660ZTO/SlOZaM/X3d 09TS80/910Z OAV
Figure imgf000019_0001
제 3항에있어서，
상기조성물은피리미딘옥사이드유도체또는그의약학적으로 허용가능한염을더포함하는발모촉진또는탈모방지용조성물. 제 4항에있어서，
상기피리미딘옥사이드유도체는
6- (피페리니딜) -2,4-피리미딘디아민 -3-옥사이드 (6-(piperidinyl)-2,4, -pyrimidinediamine-3-oxide)또는
2,4-디아미노 -6-피를리디노-피리미딘 -3-옥사이드 (2,4-diamino-6-py rrolidino-pyrimidine-3-oxide)에서선택되는어느하나또는둘인 것을특징으로하는발모촉진또는탈모방지용조성물.
제 1내지 5항증어느한항에있어서，
상기화학식 1로표시되는유도체와상기피리미딘옥사이드 유도체는 1：으 1내지 10로포함되는것을특징으로하는발모촉진 또는탈모방지용조성물.
제 6항에있어서,
상기조성물은 0.01ᅳ 10중량 %의유효성분으로함유하는 발모촉진또는탈모방지용조성물.
제 1항에있어서，
상기조성물올약학적조성물또는화장료조성물인발모촉진 또는탈모방지용조성물.
제 8항에있어서，
상기조성물은용액제，크림제，연고제,페이스트,에어로졸제, 겔제또는왁스제형태를포함하는피부외용제제형이거나,샴푸， 린스,앰플또는트리트먼트형태의모발외용제제형인발모촉진 또는탈모방지용조성물.
PCT/KR2015/012099 2014-11-28 2015-11-11 발모촉진용 또는 탈모방지용 조성물 WO2016085160A2 (ko)

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KR10-2015-0102490 2015-07-20
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