WO2016052775A1 - Composition for treating acne, and method for producing therapeutic agent for acne using same - Google Patents

Composition for treating acne, and method for producing therapeutic agent for acne using same Download PDF

Info

Publication number
WO2016052775A1
WO2016052775A1 PCT/KR2014/009145 KR2014009145W WO2016052775A1 WO 2016052775 A1 WO2016052775 A1 WO 2016052775A1 KR 2014009145 W KR2014009145 W KR 2014009145W WO 2016052775 A1 WO2016052775 A1 WO 2016052775A1
Authority
WO
WIPO (PCT)
Prior art keywords
alcohol
acne
group
composition
oil
Prior art date
Application number
PCT/KR2014/009145
Other languages
French (fr)
Korean (ko)
Inventor
이승용
이윤희
지윤택
나건
Original Assignee
(주)나노팜
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 (주)나노팜 filed Critical (주)나노팜
Priority to CN201480072497.6A priority Critical patent/CN105899206A/en
Publication of WO2016052775A1 publication Critical patent/WO2016052775A1/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—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
    • A61K31/409—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 having four such rings, e.g. porphine derivatives, bilirubin, biliverdine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
    • A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery

Definitions

  • One embodiment of the present invention relates to a composition for treating acne and a method for preparing acne treatment using the same.
  • acne is a refractory skin disease caused by fungal and bacterial infections, which requires a long-term treatment period and is not easy to treat.
  • hormonal agents can cause side effects during long-term administration such as erythema or dryness of the skin.
  • the antibiotics, benzoyl peroxide and retinoic acid cause carcinogenic and contact dermatitis problems. have. Tetracyclin, erythromycin, and clindamycin have been shown to be effective as acne treatments. However, it is reported that there is a possibility of the emergence of resistant bacteria, which may limit their use.
  • photodynamic therapy is a kind of radical therapy such as chemotherapy that can treat lesions without surgery by using photosensitizer, which is selective and photosensitive for various lesions.
  • PDT photodynamic therapy
  • the photosensitive material activates oxygen molecules to convert into singlet oxygen or create new radicals. Only lesions are selectively attacked and destroyed.
  • the photosensitive material is a porphyrin-like compound, and porphyrin-based compounds extracted from the powders of the latent plant, mulberry, green algae, etc. have spectroscopic properties suitable for use as a photosensitive material, and have a relatively high cell permeability. It is known that (700-900 nm) can efficiently generate an electron transition and its excited state.
  • One embodiment of the present invention is to provide a composition for treating acne and harmless to the human body does not cause side effects and a method for producing an acne treatment using the same.
  • an embodiment of the present invention is to provide a composition for treating acne comprising a photosensitive material having optical properties and disease target properties and a method for producing an acne treatment using the same.
  • the composition for treating acne comprising a photodynamic therapy nano-ionic complex consisting of a copolymer in which a hydrophilic cationic polymer and a photosensitizer are combined and a combination of an anionic substrate polymer and a quencher.
  • the copolymer is polyethylene glycol-polyethylenimine-pheophorbide A, the conjugate is chondroitin sulfate-blackhole quencher (BHQ), and the photodynamic therapy nano ion for 100 grams of the acne treatment composition. It provides a composition for treating acne comprising more than 0 and less than 1 mg of the complex.
  • the acne treatment composition is 0.1-10% by weight of emulsifier, 0.1-10% by weight of the first alcohol, 0.1-10% by weight of the second alcohol, 0.1-10% by weight of fatty acid, 1-40% by weight of oil, and the remaining amount of purified water. It may further include.
  • the emulsifier may be a nonionic surfactant having a structure of hydroxyl group (-OH), ether group (-O-), amide group (-CONH), ester group (-COO-) in the molecule;
  • the first alcohol may be at least one selected from the group consisting of glycerin, propylene glycol, butylene glycol, dipropylene glycol, polyethylene glycol, sorbitol, or a combination thereof.
  • the second alcohol may be lauryl alcohol, cetyl alcohol, stearyl alcohol, cetearyl alcohol, oleyl alcohol, behenyl alcohol, linoleyl alcohol, undecylyl alcohol, palmitoleyl alcohol, linolenyl alcohol, arachidonyl At least one selected from the group consisting of alcohol, erucyl alcohol, or a combination thereof.
  • the fatty acid may be at least one selected from the group consisting of stearic acid, lauric acid, myristic acid, behenic acid, isostearic acid, oleic acid, or a combination thereof.
  • the oils may be cyclodimethicone, dimethicone, diethylhexylcarbonate, hydrogenated polydesin, myritearic acid isopropyl, liquid paraffin, vegetable squalane, macadamia nut oil, jojoba oil, avocado oil, olive oil, camellia oil, or their At least one selected from the group consisting of a combination.
  • a method for producing an acne treatment comprising the composition for acne treatment described above, comprising the steps of preparing an aqueous phase material by heating an emulsifier, a first alcohol, and purified water; Heating the first alcohol, fatty acid, and oil to produce an oily raw material; Mixing the heated aqueous phase material and the oily raw material; Neutralizing the mixture and then cooling; And homogenizing the cooled mixture with the nano-ionic complex for photodynamic therapy.
  • composition for treating acne and a method for preparing an acne treatment using the same, which are harmless to the human body and do not cause side effects.
  • composition for acne treatment and the method for preparing acne treatment using the same including photosensitive material having optical properties and disease target properties for photodynamic therapy (PDT) Can provide.
  • PDT photodynamic therapy
  • the composition for treating acne comprising a photodynamic therapy nano-ionic complex consisting of a copolymer in which a hydrophilic cationic polymer and a photosensitizer are combined and a combination of an anionic substrate polymer and a quencher.
  • the copolymer is polyethylene glycol-polyethylenimine-pheophorbide A, the conjugate is chondroitin sulfate-blackhole quencher (BHQ), and the photodynamic therapy nano ion for 100 grams of the acne treatment composition. It provides a composition for treating acne comprising more than 0 and less than 1 mg of the complex.
  • the hydrophilic cationic polymers include glycol chitosan, chitosan, poly-L-lysine (PLL), poly-beta-amino ester polymers, polyethyleneimine (PEI), poly (amidoamine) (PAMAM) dendrimers and derivatives thereof
  • the hydrophilic cationic polymer may form ionic composite nanoparticles by an anionic substrate polymer and electrostatic attraction described below.
  • the hydrophilic cationic polymer may include polyethylene glycol and polyethyleneimine.
  • the polyethylene glycol (PEG) has a structural formula represented by HO- (CH 2 CH 2 O) nH, in this case due to the structural properties having ethylene oxide ((CH 2 CH 2 O)-) is connected repeatedly It shows strong hydrophilicity. In addition, these properties have characteristics that impart biocompatibility when combined with proteins or compounds.
  • polyethylene glycol is also present in the form of methoxy polyethylene glycol (mPEG) in which one end is substituted with a methoxy group (CH 3 O-), and the structural formula is represented by CH 3 O- (CH 2 CH 2 O) nH. do.
  • mPEG methoxy polyethylene glycol
  • methoxy polyethylene glycol derivatives are mostly used as polyethylene glycol. This is because the terminal of the polyethylene glycol is protected with a methoxy group, so that the stability of the structure can be maintained.
  • polyethylene glycol may be polyethylene glycol having a carboxyl group at the terminal having a molecular weight of 300 to 50,000.
  • the polyethylene glycol may be methoxy polyethylene glycol in which one end is substituted with a methoxy group.
  • the polyethyleneimine is a cationic polymer electrolyte that has been utilized in the papermaking field for a long time.
  • polyethyleneimine is divided into linear and branched forms according to its structure, and the synthesis method of the two is different.
  • Polyethyleneimines generally used are branched, where the number of primary amines, secondary amines and tertiary amines is present in a ratio of 1: 2: 1.
  • Branched polyethyleneimine is known to exist in about one to three branches of the main chain nitrogen atom, the polyethyleneimine is dissolved in water, alcohol, glycol, dimethylformamide, tetrahydrofuran, esters, etc. It is known to be insoluble in high molecular weight hydrocarbons, oleic acid and diethyl ether.
  • the polyethyleneimine may be a non-toxic branched polyethyleneimine, and when the molecular weight of the polyethyleneimine is less than 100, the copolymer produced according to the present invention may not bind well with a useful bioactive substance, and the molecular weight is 25,000. If abnormal, there is a problem that is difficult to discharge out of the body through the kidneys in the body. Therefore, polyethyleneimine may have a molecular weight of 100 to 25,000, and preferably 100 to 2000.
  • the photosensitizer is a porphyrin compound, a chlorins compound, a bacteriochlorins compound, a phthalocyanine compound, a naphthalocyanine compound, and a 5-aminolevulin ester compound ( 5-aminoevuline esters) compounds selected from the group consisting of can be used.
  • the photosensitizer may be Chlorin e6, Zinc Phthalocyanine or Pheophorbide A.
  • the binder is composed of a form of a quencher bonded to the anionic substrate polymer.
  • the anionic matrix polymers include chondroitin-6-sulfate (C6S), heparan sulfate (HS), heparan sulfate proteoglycan (HSPG), heparin, chondroitin-4-sulfate (C4S), chondroitin-6-sulfate ( C6S), dermatan sulfate (DS), keratan sulfate (KS), and hyaluronic acid (HA) can be used.
  • C6S chondroitin-6-sulfate
  • HS heparan sulfate
  • HSPG heparan sulfate proteoglycan
  • C4S heparin
  • C4S chondroitin-4-sulfate
  • C6S chondroitin-6-sulfate
  • DS dermatan sulfate
  • KS keratan sulfate
  • HA hyaluronic acid
  • the quencher may be selected from the group consisting of blackhole quencher (BHQ), blackberry quencher (BBQ), and derivatives thereof.
  • the present invention is characterized in that the cationic polymer, that is, hydrophilic cationic polymer is used to impart hydrophilicity to the photosensitizer having hydrophobicity, so that the precipitate is not dissolved in the solution or water during optical treatment.
  • the cationic polymer that is, hydrophilic cationic polymer is used to impart hydrophilicity to the photosensitizer having hydrophobicity, so that the precipitate is not dissolved in the solution or water during optical treatment.
  • acne treatment composition is 0.1-10% by weight emulsifier; 0.1-10% by weight of first alcohol; 0.1-10% by weight of second alcohol; 0.1-10% by weight of fatty acid; Oil 1-40% by weight; And the remaining amount of purified water; may further include.
  • the content of the emulsifier, the first and second alcohols, fatty acids, oils, and purified water is the same as the above range, the effect of the acne treatment agent using the acne treatment composition may be further improved.
  • the emulsifier is a nonionic surfactant having a structure of hydroxyl group (-OH), ether group (-O-), amide group (-CONH), ester group (-COO-) in the molecule;
  • the first alcohol may be at least one selected from the group consisting of glycerin, propylene glycol, butylene glycol, dipropylene glycol, polyethylene glycol, sorbitol, or a combination thereof.
  • the second alcohol may be lauryl alcohol, cetyl alcohol, stearyl alcohol, cetearyl alcohol, oleyl alcohol, behenyl alcohol, linoleyl alcohol, undecylyl alcohol, palmitoleyl alcohol, linolenyl alcohol, arachidonyl At least one selected from the group consisting of alcohol, erucyl alcohol, or a combination thereof.
  • the fatty acid may be at least one selected from the group consisting of stearic acid, lauric acid, myristic acid, behenic acid, isostearic acid, oleic acid, or a combination thereof.
  • the oils may be cyclodimethicone, dimethicone, diethylhexylcarbonate, hydrogenated polydesin, myritearic acid isopropyl, liquid paraffin, vegetable squalane, macadamia nut oil, jojoba oil, avocado oil, olive oil, camellia oil, or their At least one selected from the group consisting of a combination.
  • a method for producing an acne treatment comprising the composition for acne treatment described above, comprising the steps of preparing an aqueous phase material by heating an emulsifier, a first alcohol, and purified water; Heating the first alcohol, fatty acid, and oil to produce an oily raw material; Mixing the heated aqueous phase material and the oily raw material; Neutralizing the mixture and then cooling; And homogenizing the cooled mixture with the nano-ionic complex for photodynamic therapy.
  • an acne treatment agent prepared according to the method for producing an acne treatment described above provides an acne treatment of the emulsion type, gel (gel), liquid form, or powder form.
  • mPEG-COOH methoxy polyethylene glycol
  • CHCl 2 methylene chloride
  • 0.52 g of N-hydroxysuccinylimide and 0.74 g of dicyclocarbodiimide were added, followed by reaction at room temperature for 20 hours.
  • Dicyclohexyl urea was removed through a filter process and then precipitated in diethylether to obtain activated polyethylene glycol (mPEG-NHS).
  • polyethylene glycol 2 g was dissolved in 200 ml of chloroform. Thereafter, 0.5 g of polyethyleneimine (Alfa Aesar, 1800da) was dissolved in 50 ml of chloroform, and then a covalent reaction of polyethylene glycol and polyethyleneimine was performed by dropping a solution of the polyethylene glycol dissolved therein drop by drop.
  • polyethyleneimine Alfa Aesar, 1800da
  • reaction was carried out for 24 hours, after completion of the reaction was concentrated to a total volume of 30ml by using a vacuum concentrator, and then precipitated in diethyl ether to covalently bond the polyethylene glycol and polyethyleneimine Obtained.
  • Cutoff size, 1,000) was dialyzed with primary distilled water for 2 days, and then the final reaction product was dried by lyophilization to obtain polyethylene glycol-polyethylenimine-piopho. A pheophorbide A copolymer was obtained.
  • chondroitin sulfate 0.1 g was dissolved in 20 ml of distilled water. After dissolving BHQ3 in dried DMSO, N- (3-dimethylaminopropyl) -N'-ethylcarbodiimine hydrochloride (EDC) and 4-dimethylaminopyridine (DMAP) were each added 1.5-fold to the molar ratio of BHQ. . Then, the two solutions were each stirred at room temperature for 3 hours, then mixed and reacted for 24 hours. Removal of unreacted quencher (BHQ3) was removed by dialysis using primary distilled water for 2 days using a dialysis membrane (Spectra / Por; mol. Wt. Cutoff size, 1,000), and the final reaction product was freeze-dried after dialysis. Drying through gave a quencher conjugated chondroitin sulfate conjugate.
  • EDC N- (3-dimethylaminopropyl) -N'-ethylcarbodi
  • Purified water, glycerin, and raw materials were water phases, and emulsifiers, polyhydric alcohols, higher fatty acids, and oils were used as oil phases according to the compositions shown in Table 1 below, and each phase was heated and dissolved to 80 ° C.
  • the oil phase or the oil phase was slowly added to the water phase and uniformly mixed with a mixer to emulsify at 80 ° C for 10 minutes.
  • the emulsion was neutralized with a pH adjuster at 70 ° C. or lower and then cooled to 45 ° C. to obtain a mixture of raw materials.
  • Table 1 ingredient Content Award raw material Purified water Remaining amount Glycerin (polyhydric alcohol) 10 Xanthan Gum 10 Oily raw material Polysorbate 80 (emulsifier) 2 Cetyl Alcohol (Advanced Alcohol) One Stearic acid (high fatty acid) One Dimethicone (oil) 0.5 Macadamia Nut Oil (Oil) One Cyclodimethicone (oil) 3 Liquid paraffin (oil) 2 Hydrogenated Polydesine (Oil) 10 additive Triethanolamine (pH regulator) Quantity Nano ion composite Less than 1mg / 100gr antiseptic a very small amount
  • the gel-type acne treatment agent was prepared in the same manner as in Example 1, except that a mixture of raw materials was prepared by dispersing purified water, glycerin, a hydrophilic polymer compound, and ethanol by heating to 40 ° C. in an aqueous phase. Was prepared.
  • a liquid acne treatment agent was prepared in the same manner as in Example 1, except that starch, dextrin, and glucose were used as excipients, and homogenized by impregnating a polyhydric alcohol and a nano ion complex. It was.
  • One embodiment of the present invention is to provide a composition for treating acne and harmless to the human body does not cause side effects and a method for producing an acne treatment using the same.
  • an embodiment of the present invention is to provide a composition for treating acne comprising a photosensitive material having optical properties and disease target properties and a method for producing an acne treatment using the same.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nanotechnology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Inorganic Chemistry (AREA)
  • Gastroenterology & Hepatology (AREA)
  • General Engineering & Computer Science (AREA)
  • Medical Informatics (AREA)
  • Dispersion Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Manufacturing & Machinery (AREA)
  • Biotechnology (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

A composition for treating acne and a method for producing a therapeutic agent for acne using same are disclosed. One embodiment of the present invention provides a composition for treating acne, which comprises a nano-ionic composite for photodynamic therapy comprising: a copolymer formed by joining a hydrophilic cationic polymer and a photosensitizer; and a conjugate formed by joining an anionic matrix polymer and a quencher, wherein the copolymer is polyethylene glycol-polyethyleneimine-pheophorbide A, the conjugate is chondroitin sulfate-black hole quencher (BHQ), and over 0 to 1 mg of the nano-ionic composite for photodynamic therapy is comprised with respect to 100 g of the composition for treating acne.

Description

여드름 치료용 조성물 및 이를 이용한 여드름 치료제의 제조 방법Acne treatment composition and preparation method of acne treatment using the same
본 발명의 일 구현예는 여드름 치료용 조성물 및 이를 이용한 여드름 치료제의 제조 방법에 관한 것이다.One embodiment of the present invention relates to a composition for treating acne and a method for preparing acne treatment using the same.
피부질환은 비록 생명에는 지장을 주지 않으나 그 발생빈도가 높으며 현대인의 경우 다양한 원인과 기후, 스트레스 등으로 점점 더 발생빈도가 높아지는 추세이다.Although skin disease does not affect life, its incidence is high, and in modern people, the frequency of occurrence is increasing due to various causes, climate, and stress.
특히, 여드름은 진균 및 세균의 감염에 의한 난치성 피부질환으로서, 장기적인 치료기간을 필요로 하며 치료도 쉽지 않다.In particular, acne is a refractory skin disease caused by fungal and bacterial infections, which requires a long-term treatment period and is not easy to treat.
여드름을 치료하기 위한 방법으로는, 피지 생성을 억제하는 호르몬제, 항생제 투여가 처방되고 있다. 이러한 방법은 여드름 예방과 치료에 어느 정도 효과가 있으나, 만족할 만한 효과적인 측면이나 피부안전성 측면에 있어 부작용이 문제시 되고 있다. As a method for treating acne, administration of hormones and antibiotics that inhibit sebum production is prescribed. Although this method has some effects on acne prevention and treatment, side effects are problematic in terms of satisfactory effective and skin safety aspects.
특히, 호르몬제의 경우에는 피부의 홍반이나 건조증 등 장기 투여 시, 부작용을 유발할 수 있으며, 항생제인 벤조일 퍼록사이트(benzoyl peroxide)와 레티노익산(Retinoic acid)는 발암성 및 접촉성 피부염 유발의 문제가 있다. 그 외 여드름 치료제로 테트라싸이클린(tetracyclin), 에리스로마이신(erythromycin) 및 클린다마이신(clindamycin)를 사용하여 효과를 보고 있으나, 내성균의 출현 등의 가능성이 있는 것으로 보고되고 있어 사용에 제한이 따를 수 있다In particular, hormonal agents can cause side effects during long-term administration such as erythema or dryness of the skin. The antibiotics, benzoyl peroxide and retinoic acid, cause carcinogenic and contact dermatitis problems. have. Tetracyclin, erythromycin, and clindamycin have been shown to be effective as acne treatments. However, it is reported that there is a possibility of the emergence of resistant bacteria, which may limit their use.
한편, 광역학 치료법(photodynamic therapy, PDT)이란, 각종 병변에 대해 선택성 및 광증감성이 있는 광민감성 물질(photosensitizer)을 이용하여 수술 없이 병변을 치료할 수 있는 일종의 화학요법제와 같은 근치법이다. 예컨대, 상기 광민감성 물질을 정맥주사에 의해 대상자에 투여하고, 이에 적절한 광(light)을 조사함으로써, 광민감성 물질이 산소분자를 활성화시켜 단일항(singlet) 상태의 산소로 변환 혹은 새로운 라디칼을 만들어 병변 만을 선택적으로 공격, 궤멸시키는 것이다.On the other hand, photodynamic therapy (PDT) is a kind of radical therapy such as chemotherapy that can treat lesions without surgery by using photosensitizer, which is selective and photosensitive for various lesions. For example, by administering the photosensitive material to a subject by intravenous injection and irradiating with appropriate light, the photosensitive material activates oxygen molecules to convert into singlet oxygen or create new radicals. Only lesions are selectively attacked and destroyed.
이러한 광민감성 물질로는 포르피린(porphyrin) 류의 화합물이 대표적인데, 잠분이나 뽕잎, 녹조류 등에서 추출되는 포르피린계 화합물은 광민감성 물질로 사용하기에 적합한 분광학적 특성을 갖고 있고, 비교적 세포투과력이 큰 적색광(700-900nm)에 의해 전자 전이를 일으키는 성질과 그에 따른 여기상태를 효율적으로 생성할 수 있는 것으로 알려져 있다.The photosensitive material is a porphyrin-like compound, and porphyrin-based compounds extracted from the powders of the latent plant, mulberry, green algae, etc. have spectroscopic properties suitable for use as a photosensitive material, and have a relatively high cell permeability. It is known that (700-900 nm) can efficiently generate an electron transition and its excited state.
본 발명의 일 구현예는 인체에 무해하며 부작용을 야기하지 않는 여드름 치료용 조성물 및 이를 이용한 여드름 치료제의 제조 방법을 제공하고자 한다.One embodiment of the present invention is to provide a composition for treating acne and harmless to the human body does not cause side effects and a method for producing an acne treatment using the same.
또한, 본 발명의 일 구현예는 광학 특성과 질병 표적 특성을 갖는 광민감성 물질을 포함하는 여드름 치료용 조성물 및 이를 이용한 여드름 치료제의 제조 방법을 제공하고자 한다.In addition, an embodiment of the present invention is to provide a composition for treating acne comprising a photosensitive material having optical properties and disease target properties and a method for producing an acne treatment using the same.
본 발명의 일 구현예는, 친수성 양이온 고분자와 광감작제가 결합된 공중합체 및 음이온성 기질 고분자와 소광제가 결합된 결합체로 구성된 광역학 치료용 나노 이온 복합체를 포함하는 여드름 치료용 조성물로서, 상기 공중합체는 폴리에틸렌글리콜-폴리에틸렌이민-피오포바이드(pheophorbide) A이고, 상기 결합체는 콘드로이틴 설페이트-블랙홀 소광제(blackhole quencher, BHQ)이며, 상기 여드름 치료용 조성물 100그램에 대하여 상기 광역학 치료용 나노 이온 복합체를 0 초과 및 1밀리그램 이하로 포함하는 여드름 치료용 조성물을 제공한다.In one embodiment of the present invention, the composition for treating acne comprising a photodynamic therapy nano-ionic complex consisting of a copolymer in which a hydrophilic cationic polymer and a photosensitizer are combined and a combination of an anionic substrate polymer and a quencher. The copolymer is polyethylene glycol-polyethylenimine-pheophorbide A, the conjugate is chondroitin sulfate-blackhole quencher (BHQ), and the photodynamic therapy nano ion for 100 grams of the acne treatment composition. It provides a composition for treating acne comprising more than 0 and less than 1 mg of the complex.
상기 여드름 치료용 조성물은 유화제 0.1-10중량%, 제1 알콜 0.1-10중량%, 제2 알콜 0.1-10중량%, 지방산 0.1-10중량%, 오일 1-40중량%, 및 잔량의 정제수를 더 포함할 수 있다.The acne treatment composition is 0.1-10% by weight of emulsifier, 0.1-10% by weight of the first alcohol, 0.1-10% by weight of the second alcohol, 0.1-10% by weight of fatty acid, 1-40% by weight of oil, and the remaining amount of purified water. It may further include.
상기 유화제는 분자 중에 수산기(-OH), 에테르기(-O-), 아미드기(-CONH), 에스테르기(-COO-)의 구조를 가진 비이온성 계면활성제; 폴리옥시에틸렌형, 다가알콜에스테르형, 에틸렌옥사이드 및 프로필렌옥사이드 블록 공중합체, 아크릴산알킬공중합체의 폴리머릭 계면활성제; 레시틴, 라놀린, 콜레스테롤, 사포닌의 천연 계면활성제;로 이루어진 군으로부터 선택된 적어도 하나일 수 있다.The emulsifier may be a nonionic surfactant having a structure of hydroxyl group (-OH), ether group (-O-), amide group (-CONH), ester group (-COO-) in the molecule; Polymeric surfactants of polyoxyethylene type, polyhydric alcohol ester type, ethylene oxide and propylene oxide block copolymers, alkyl acrylate copolymers; It may be at least one selected from the group consisting of: natural surfactant of lecithin, lanolin, cholesterol, saponin.
상기 제1 알콜은 다가 알콜로서, 글리세린, 프로필렌글라이콜, 부틸렌글라이콜, 디프로필렌글라이콜, 폴리에틸렌글리콜, 솔비톨, 또는 이들의 조합으로 이루어진 군으로부터 선택된 적어도 하나일 수 있다.The first alcohol may be at least one selected from the group consisting of glycerin, propylene glycol, butylene glycol, dipropylene glycol, polyethylene glycol, sorbitol, or a combination thereof.
상기 제2 알코올은 라우릴 알콜, 세틸 알콜, 스테아릴 알콜, 세테아릴 알콜, 올레일 알콜, 베헤닐 알콜, 리놀레일 알콜, 운데실레닐 알콜, 팔미톨레일 알콜, 리놀레닐 알콜, 아라키도닐 알콜, 에루실 알코올, 또는 이들의 조합으로 이루어진 군으로부터 선택된 적어도 하나일 수 있다.The second alcohol may be lauryl alcohol, cetyl alcohol, stearyl alcohol, cetearyl alcohol, oleyl alcohol, behenyl alcohol, linoleyl alcohol, undecylyl alcohol, palmitoleyl alcohol, linolenyl alcohol, arachidonyl At least one selected from the group consisting of alcohol, erucyl alcohol, or a combination thereof.
상기 지방산은 스테아린산, 라우린산, 미리스틴산, 베헤닌산, 이소스테아린산, 올레인산, 또는 이들의 조합으로 이루어진 군으로부터 선택된 적어도 하나일 수 있다.The fatty acid may be at least one selected from the group consisting of stearic acid, lauric acid, myristic acid, behenic acid, isostearic acid, oleic acid, or a combination thereof.
상기 오일은 시클로디메치콘, 디메치콘, 디에틸헥실카보네이트, 하이드로게네이티드폴리데신, 미리스테아린산 이소프로필, 리퀴드파라핀, 식물성 스쿠알란, 마카다미아넛오일, 호호바오일, 아보카도오일, 올리브오일, 동백유, 또는 이들의 조합으로 이루어진 군으로부터 선택된 적어도 하나일 수 있다.The oils may be cyclodimethicone, dimethicone, diethylhexylcarbonate, hydrogenated polydesin, myritearic acid isopropyl, liquid paraffin, vegetable squalane, macadamia nut oil, jojoba oil, avocado oil, olive oil, camellia oil, or their At least one selected from the group consisting of a combination.
또한, 본 발명의 다른 구현예는, 전술한 여드름 치료용 조성물을 포함하는 여드름 치료제의 제조 방법으로서, 유화제, 제1 알콜, 및 정제수를 가열하여 수상 원료물질을 제조하는 단계; 제1 알콜, 지방산, 및 오일을 가열하여 유상 원료물질을 제조하는 단계; 가열된 상기 수상 원료물질 및 상기 유상 원료물질을 혼합하는 단계; 상기 혼합물을 중화한 후, 냉각하는 단계; 및 상기 냉각된 혼합물을 광역학 치료용 나노 이온 복합체와 균질화하는 단계;를 포함하는 여드름 치료제의 제조 방법을 제공한다.In addition, another embodiment of the present invention, a method for producing an acne treatment comprising the composition for acne treatment described above, comprising the steps of preparing an aqueous phase material by heating an emulsifier, a first alcohol, and purified water; Heating the first alcohol, fatty acid, and oil to produce an oily raw material; Mixing the heated aqueous phase material and the oily raw material; Neutralizing the mixture and then cooling; And homogenizing the cooled mixture with the nano-ionic complex for photodynamic therapy.
본 발명의 일 구현예에 따르면, 인체에 무해하며 부작용을 야기하지 않는 여드름 치료용 조성물 및 이를 이용한 여드름 치료제의 제조 방법을 제공할 수 있다.According to one embodiment of the present invention, it is possible to provide a composition for treating acne and a method for preparing an acne treatment using the same, which are harmless to the human body and do not cause side effects.
또한, 본 발명의 일 구현예에 따르면, 광학 특성과 질병 표적 특성을 갖는 광민감성 물질을 포함하여 광역학 치료(Photodynamic therapy, PDT)에 활용 가능한 여드름 치료용 조성물 및 이를 이용한 여드름 치료제의 제조 방법을 제공할 수 있다.In addition, according to an embodiment of the present invention, the composition for acne treatment and the method for preparing acne treatment using the same, including photosensitive material having optical properties and disease target properties for photodynamic therapy (PDT) Can provide.
이하, 본 발명의 구현예를 상세히 설명하기로 한다. 다만, 이는 예시로서 제시되는 것으로, 이에 의해 본 발명이 제한되지는 않으며 본 발명은 후술할 청구항의 범주에 의해 정의될 뿐이다.Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, by which the present invention is not limited and the present invention is defined only by the scope of the claims to be described later.
본 발명의 일 구현예는, 친수성 양이온 고분자와 광감작제가 결합된 공중합체 및 음이온성 기질 고분자와 소광제가 결합된 결합체로 구성된 광역학 치료용 나노 이온 복합체를 포함하는 여드름 치료용 조성물로서, 상기 공중합체는 폴리에틸렌글리콜-폴리에틸렌이민-피오포바이드(pheophorbide) A이고, 상기 결합체는 콘드로이틴 설페이트-블랙홀 소광제(blackhole quencher, BHQ)이며, 상기 여드름 치료용 조성물 100그램에 대하여 상기 광역학 치료용 나노 이온 복합체를 0 초과 및 1밀리그램 이하로 포함하는 여드름 치료용 조성물을 제공한다.In one embodiment of the present invention, the composition for treating acne comprising a photodynamic therapy nano-ionic complex consisting of a copolymer in which a hydrophilic cationic polymer and a photosensitizer are combined and a combination of an anionic substrate polymer and a quencher. The copolymer is polyethylene glycol-polyethylenimine-pheophorbide A, the conjugate is chondroitin sulfate-blackhole quencher (BHQ), and the photodynamic therapy nano ion for 100 grams of the acne treatment composition. It provides a composition for treating acne comprising more than 0 and less than 1 mg of the complex.
상기 친수성 양이온 고분자는 글라이콜 키토산, 키토산, 폴리-L-리신(PLL), 폴리-베타-아미노 에스터 고분자, 폴리 에틸렌이민(PEI), 폴리(아미도아민) (PAMAM)덴드리머 및 이들의 유도체로 이루어진 군 중에서 선택된 것을 사용할 수 있으며, 상기 친수성 양이온 고분자는 후술되는 음이온성 기질 고분자와 정전기적 인력에 의해 이온 복합체 나노 입자를 형성할 수 있다. The hydrophilic cationic polymers include glycol chitosan, chitosan, poly-L-lysine (PLL), poly-beta-amino ester polymers, polyethyleneimine (PEI), poly (amidoamine) (PAMAM) dendrimers and derivatives thereof The hydrophilic cationic polymer may form ionic composite nanoparticles by an anionic substrate polymer and electrostatic attraction described below.
예컨대, 상기 친수성 양이온 고분자는 폴리에틸렌글리콜 및 폴리에틸렌이민을 포함할 수 있다. For example, the hydrophilic cationic polymer may include polyethylene glycol and polyethyleneimine.
이 때, 상기 폴리에틸렌글리콜(PEG)은 HO-(CH2CH2O)n-H로 표현되는 구조식을 가지며, 이 경우 반복 연결되는 에틸렌 옥사이드((CH2CH2O)-)를 가지는 구조적 특성으로 인해 강한 친수성을 나타낸다. 또한, 이러한 특성이 단백질 또는 화합물과 결합하는 경우에 생체친화성을 부여하게 되는 특징을 가진다. At this time, the polyethylene glycol (PEG) has a structural formula represented by HO- (CH 2 CH 2 O) nH, in this case due to the structural properties having ethylene oxide ((CH 2 CH 2 O)-) is connected repeatedly It shows strong hydrophilicity. In addition, these properties have characteristics that impart biocompatibility when combined with proteins or compounds.
또한, 폴리에틸렌글리콜은 한쪽 말단이 메톡시기(CH3O-)로 치환된 메톡시폴리에틸렌글리콜(mPEG)의 형태로도 존재하는데, 그 구조식은 CH3O-(CH2CH2O)n-H로 표현된다. 특히, 폴리에틸렌글리콜-단백질의 형태를 가지는 제제의 경우, 폴리에틸렌글리콜로 대부분 메톡시폴리에틸렌글리콜 유도체들이 사용되고 있다. 이는, 폴리에틸렌글리콜의 말단이 메톡시기로 보호되어 있어 구조의 안정성을 유지할 수 있기 때문이다. In addition, polyethylene glycol is also present in the form of methoxy polyethylene glycol (mPEG) in which one end is substituted with a methoxy group (CH 3 O-), and the structural formula is represented by CH 3 O- (CH 2 CH 2 O) nH. do. In particular, in the case of a preparation having a form of polyethylene glycol-protein, methoxy polyethylene glycol derivatives are mostly used as polyethylene glycol. This is because the terminal of the polyethylene glycol is protected with a methoxy group, so that the stability of the structure can be maintained.
본 발명의 일 구현예에서, 폴리에틸렌글리콜은 분자량이 300 내지 50,000인 말단에 카르복실기를 갖는 폴리에틸렌글리콜 일 수 있다. 또한, 폴리에틸렌글리콜은 한쪽 말단이 메톡시기로 치환된 메톡시 폴리에틸렌글리콜일 수 있다.In one embodiment of the present invention, polyethylene glycol may be polyethylene glycol having a carboxyl group at the terminal having a molecular weight of 300 to 50,000. In addition, the polyethylene glycol may be methoxy polyethylene glycol in which one end is substituted with a methoxy group.
한편, 상기 폴리에틸렌이민은 이미 오래 전부터 제지분야에서 활용되고 있는 양이온성 고분자 전해질이다. 일반적으로 폴리에틸렌이민은 그 구조에 따라 선형과 가지형으로 나뉘는데, 이 둘의 합성 방법은 서로 다르다. 일반적으로 사용되고 있는 폴리에틸렌이민은 가지형으로, 여기에는 일차 아민, 이차 아민, 삼차 아민의 수가 1:2:1의 비율로 존재한다. 가지형 폴리에틸렌이민의 가지사슬은 주사슬 질소 원자의 3-3.5 개당 하나 정도 존재하는 것으로 알려져 있으며, 이러한 폴리에틸렌이민은 물, 알코올, 글리콜, 디메틸포름아미드, 테트라하이드로퓨란, 에스테르류 등에 용해되는 한편, 고분자량의 탄화수소류, 올릭산(oleic acid), 디에틸에테르에는 용해되지 않는 것으로 알려져 있다.On the other hand, the polyethyleneimine is a cationic polymer electrolyte that has been utilized in the papermaking field for a long time. Generally, polyethyleneimine is divided into linear and branched forms according to its structure, and the synthesis method of the two is different. Polyethyleneimines generally used are branched, where the number of primary amines, secondary amines and tertiary amines is present in a ratio of 1: 2: 1. Branched polyethyleneimine is known to exist in about one to three branches of the main chain nitrogen atom, the polyethyleneimine is dissolved in water, alcohol, glycol, dimethylformamide, tetrahydrofuran, esters, etc. It is known to be insoluble in high molecular weight hydrocarbons, oleic acid and diethyl ether.
예컨대, 상기 폴리에틸렌이민은 독성이 없는 가지형 폴리에틸렌이민을 사용할 수 있으며, 폴리에틸렌이민의 분자량이 100 미만일 경우에는 본 발명에 따라 생성된 공중합체가 유용한 생리활성물질과 잘 결합할 수 없으며, 분자량이 25,000 이상일 경우에는 체내에서 신장을 통해 몸 밖으로 배출되기 어려운 문제점이 있다. 따라서, 폴리에틸렌이민은 분자량이 100 내지 25,000 일 수 있으며, 바람직하게는 100 내지 2000 인 것을 사용할 수 있다. For example, the polyethyleneimine may be a non-toxic branched polyethyleneimine, and when the molecular weight of the polyethyleneimine is less than 100, the copolymer produced according to the present invention may not bind well with a useful bioactive substance, and the molecular weight is 25,000. If abnormal, there is a problem that is difficult to discharge out of the body through the kidneys in the body. Therefore, polyethyleneimine may have a molecular weight of 100 to 25,000, and preferably 100 to 2000.
상기 광감작제는 포르피린계(phorphyrins) 화합물, 클로린계(chlorins) 화합물, 박테리오클로린계(bacteriochlorins) 화합물, 프탈로시아닌계(phtalocyanine) 화합물, 나프탈로시아닌계(naphthalocyanines) 화합물 및 5-아미노레불린 에스테르계(5-aminoevuline esters) 화합물로 이루어진 군 중 에서 선택된 것을 사용할 수 있다. 예컨대, 상기 광감작제는 클로린 e6(Chlorin e6), 프탈로시아닌(Zinc Phthalocyanine) 또는 피오포바이드(pheophorbide) A 일 수 있다.The photosensitizer is a porphyrin compound, a chlorins compound, a bacteriochlorins compound, a phthalocyanine compound, a naphthalocyanine compound, and a 5-aminolevulin ester compound ( 5-aminoevuline esters) compounds selected from the group consisting of can be used. For example, the photosensitizer may be Chlorin e6, Zinc Phthalocyanine or Pheophorbide A.
상기 결합체는 음이온성 기질 고분자에 소광제가 결합된 형태로 구성된다.The binder is composed of a form of a quencher bonded to the anionic substrate polymer.
보다 구체적으로, 음이온성 기질 고분자는 콘드로이틴-6-설페이트(C6S), 헤파란 설페이트(HS), 헤파란 설페이트 프로테오글리칸(HSPG), 헤파린, 콘드로이틴-4-설페이트(C4S), 콘드로이틴-6-설페이트(C6S), 더마탄 설페이트(DS), 케라탄 설페이트(KS), 및 히알루론산(HA)으로 이루어진 군으로부터 선택된 것을 사용할 수 있다.More specifically, the anionic matrix polymers include chondroitin-6-sulfate (C6S), heparan sulfate (HS), heparan sulfate proteoglycan (HSPG), heparin, chondroitin-4-sulfate (C4S), chondroitin-6-sulfate ( C6S), dermatan sulfate (DS), keratan sulfate (KS), and hyaluronic acid (HA) can be used.
상기 소광제로는 블랙홀 소광제(blackhole quencher, BHQ), 블랙베리 소광제(blackberry quencher, BBQ), 및 이들의 유도체로 이루어지는 군에서 선택되는 것을 사용할 수 있다. The quencher may be selected from the group consisting of blackhole quencher (BHQ), blackberry quencher (BBQ), and derivatives thereof.
이에 따라, 본 발명에서는 양이온성 고분자, 즉, 친수성 양이온 고분자를 이용하여 소수성을 갖는 광감작제에 친수성을 부여함으로써 광학 치료 시 용액 또는 물에 잘 용해되어 침전물이 생기지 않는 특징이 있다.Accordingly, the present invention is characterized in that the cationic polymer, that is, hydrophilic cationic polymer is used to impart hydrophilicity to the photosensitizer having hydrophobicity, so that the precipitate is not dissolved in the solution or water during optical treatment.
한편, 본 발명의 일 구현예에 따른 여드름 치료용 조성물은 유화제 0.1-10중량%; 제1 알콜 0.1-10중량%; 제2 알콜 0.1-10중량%; 지방산 0.1-10중량%; 오일 1-40중량%; 및 잔량의 정제수;를 더 포함할 수 있다. 상기 유화제, 제1 및 제2 알코올, 지방산, 오일, 및 정제수의 함량이 상기 범위와 같은 경우, 여드름 치료용 조성물을 이용한 여드름 치료제의 효과가 보다 더 향상될 수 있다.On the other hand, acne treatment composition according to one embodiment of the present invention is 0.1-10% by weight emulsifier; 0.1-10% by weight of first alcohol; 0.1-10% by weight of second alcohol; 0.1-10% by weight of fatty acid; Oil 1-40% by weight; And the remaining amount of purified water; may further include. When the content of the emulsifier, the first and second alcohols, fatty acids, oils, and purified water is the same as the above range, the effect of the acne treatment agent using the acne treatment composition may be further improved.
보다 구체적으로, 상기 유화제는 분자 중에 수산기(-OH), 에테르기(-O-), 아미드기(-CONH), 에스테르기(-COO-)의 구조를 가진 비이온성 계면활성제; 폴리옥시에틸렌형, 다가알콜에스테르형, 에틸렌옥사이드 및 프로필렌옥사이드 블록 공중합체, 아크릴산알킬공중합체의 폴리머릭 계면활성제; 레시틴, 라놀린, 콜레스테롤, 사포닌의 천연 계면활성제;로 이루어진 군으로부터 선택된 적어도 하나일 수 있다.More specifically, the emulsifier is a nonionic surfactant having a structure of hydroxyl group (-OH), ether group (-O-), amide group (-CONH), ester group (-COO-) in the molecule; Polymeric surfactants of polyoxyethylene type, polyhydric alcohol ester type, ethylene oxide and propylene oxide block copolymers, alkyl acrylate copolymers; It may be at least one selected from the group consisting of: natural surfactant of lecithin, lanolin, cholesterol, saponin.
상기 제1 알콜은 다가 알콜로서, 글리세린, 프로필렌글라이콜, 부틸렌글라이콜, 디프로필렌글라이콜, 폴리에틸렌글리콜, 솔비톨, 또는 이들의 조합으로 이루어진 군으로부터 선택된 적어도 하나일 수 있다.The first alcohol may be at least one selected from the group consisting of glycerin, propylene glycol, butylene glycol, dipropylene glycol, polyethylene glycol, sorbitol, or a combination thereof.
상기 제2 알코올은 라우릴 알콜, 세틸 알콜, 스테아릴 알콜, 세테아릴 알콜, 올레일 알콜, 베헤닐 알콜, 리놀레일 알콜, 운데실레닐 알콜, 팔미톨레일 알콜, 리놀레닐 알콜, 아라키도닐 알콜, 에루실 알코올, 또는 이들의 조합으로 이루어진 군으로부터 선택된 적어도 하나일 수 있다.The second alcohol may be lauryl alcohol, cetyl alcohol, stearyl alcohol, cetearyl alcohol, oleyl alcohol, behenyl alcohol, linoleyl alcohol, undecylyl alcohol, palmitoleyl alcohol, linolenyl alcohol, arachidonyl At least one selected from the group consisting of alcohol, erucyl alcohol, or a combination thereof.
상기 지방산은 스테아린산, 라우린산, 미리스틴산, 베헤닌산, 이소스테아린산, 올레인산, 또는 이들의 조합으로 이루어진 군으로부터 선택된 적어도 하나일 수 있다.The fatty acid may be at least one selected from the group consisting of stearic acid, lauric acid, myristic acid, behenic acid, isostearic acid, oleic acid, or a combination thereof.
상기 오일은 시클로디메치콘, 디메치콘, 디에틸헥실카보네이트, 하이드로게네이티드폴리데신, 미리스테아린산 이소프로필, 리퀴드파라핀, 식물성 스쿠알란, 마카다미아넛오일, 호호바오일, 아보카도오일, 올리브오일, 동백유, 또는 이들의 조합으로 이루어진 군으로부터 선택된 적어도 하나일 수 있다.The oils may be cyclodimethicone, dimethicone, diethylhexylcarbonate, hydrogenated polydesin, myritearic acid isopropyl, liquid paraffin, vegetable squalane, macadamia nut oil, jojoba oil, avocado oil, olive oil, camellia oil, or their At least one selected from the group consisting of a combination.
본 발명의 다른 구현예는, 전술한 여드름 치료용 조성물을 포함하는 여드름 치료제의 제조 방법으로서, 유화제, 제1 알콜, 및 정제수를 가열하여 수상 원료물질을 제조하는 단계; 제1 알콜, 지방산, 및 오일을 가열하여 유상 원료물질을 제조하는 단계; 가열된 상기 수상 원료물질 및 상기 유상 원료물질을 혼합하는 단계; 상기 혼합물을 중화한 후, 냉각하는 단계; 및 상기 냉각된 혼합물을 광역학 치료용 나노 이온 복합체와 균질화하는 단계;를 포함하는 여드름 치료제의 제조 방법을 제공한다.Another embodiment of the present invention, a method for producing an acne treatment comprising the composition for acne treatment described above, comprising the steps of preparing an aqueous phase material by heating an emulsifier, a first alcohol, and purified water; Heating the first alcohol, fatty acid, and oil to produce an oily raw material; Mixing the heated aqueous phase material and the oily raw material; Neutralizing the mixture and then cooling; And homogenizing the cooled mixture with the nano-ionic complex for photodynamic therapy.
또한, 본 발명의 또 다른 구현예는, 전술한 여드름 치료제의 제조 방법에 따라 제조되는 여드름 치료제로서, 에멀젼형, 젤(gel)형, 액상형, 또는 분말형인 여드름 치료제를 제공한다.In addition, another embodiment of the present invention, as an acne treatment agent prepared according to the method for producing an acne treatment described above, provides an acne treatment of the emulsion type, gel (gel), liquid form, or powder form.
이하 본 발명의 실시예 및 비교예를 기재한다. 그러나 하기의 실시예는 본 발명의 일 실시예 일 뿐 본 발명이 하기한 실시예에 한정되는 것은 아니다.Hereinafter, examples and comparative examples of the present invention are described. However, the following examples are merely examples of the present invention and the present invention is not limited to the following examples.
실시예Example
실시예 1: 에멀전형 여드름 치료제의 제조Example 1 Preparation of Emulsion-Type Acne Therapeutics
1. 나노 이온 복합체의 제조1. Preparation of Nano-Ion Composites
1-1. 공중합체(폴리에틸렌글리콜-폴리에틸렌이민-광감각제)의 합성1-1. Synthesis of Copolymer (Polyethylene Glycol-Polyethyleneimine-Photosensitive Agent)
환류 응축기 설치 후 메톡시 폴리에틸렌 글리콜(mPEG-COOH)(시그마, 5000Da) 10g을 250ml의 플라스크를 이용하여 메틸렌클로라이드(CHCl2) 50ml에 용해시켰다. 이후, 0.52 g의 N-하이드록시숙시닐이미드와 0.74 g의 다이사이클로카보다이이미드를 첨가한 후 20시간 동안 상온에서 반응시켰다. 다이사이클로헥실우레아를 필터 과정을 통해서 제거한 후 디에틸에테르(diethylether)에 침전시킴으로써 활성화 형태의 폴리에틸렌글리콜 (mPEG-NHS)을 수득하였다.After the reflux condenser was installed, 10 g of methoxy polyethylene glycol (mPEG-COOH) (Sigma, 5000 Da) was dissolved in 50 ml of methylene chloride (CHCl 2 ) using a 250 ml flask. Thereafter, 0.52 g of N-hydroxysuccinylimide and 0.74 g of dicyclocarbodiimide were added, followed by reaction at room temperature for 20 hours. Dicyclohexyl urea was removed through a filter process and then precipitated in diethylether to obtain activated polyethylene glycol (mPEG-NHS).
상기 수득한 폴리에틸렌글리콜 2g을 200ml의 클로로포름에 녹였다. 이후, 0.5g의 폴리에틸렌이민(Alfa Aesar, 1800da)을 50ml의 클로로포름에 녹인 다음, 여기에 상기 폴리에틸렌글리콜을 녹인 용액을 한 방울씩 떨어뜨림으로써 폴리에틸렌글리콜과 폴리에틸렌이민의 공유결합 반응을 수행하였다.2 g of the obtained polyethylene glycol was dissolved in 200 ml of chloroform. Thereafter, 0.5 g of polyethyleneimine (Alfa Aesar, 1800da) was dissolved in 50 ml of chloroform, and then a covalent reaction of polyethylene glycol and polyethyleneimine was performed by dropping a solution of the polyethylene glycol dissolved therein drop by drop.
이 때, 상기 반응은 24시간 동안 수행하였으며, 반응 완료 후 진공농축 장치를 이용하여 총 부피가 30ml이 되도록 농축한 다음, 디에틸에테르(diethyl ether)에 침전시킴으로써 폴리에틸렌글리콜과 폴리에틸렌이민의 공유결합체를 수득하였다.At this time, the reaction was carried out for 24 hours, after completion of the reaction was concentrated to a total volume of 30ml by using a vacuum concentrator, and then precipitated in diethyl ether to covalently bond the polyethylene glycol and polyethyleneimine Obtained.
상기 수득한 폴리에틸렌글리콜-폴리에틸렌이민(mPEG-PEI) 1g을 피오포바이드(pheophorbide) A (e.q., 0.07 mmol), 디사이클로 헥실카보디미드(dicyclohexyl carbodiimide, DCC) (1.2*pheophorbide A in moles) 그리고 N-하이드록시석시닐이미드(HOSu; 1.2*pheophorbide A in moles)을 20ml 인 디메틸 설폭사이드(dimethyl sulfoxide, DMSO)에 각각 녹인 후 3시간 동안 교반시켰다. 이후, 각각 두 용액을 섞은 후에 상온에서 24시간 반응시켰다. 또한, 투석막 (Spectra/Por; mol. wt. cutoff size, 1,000)을 이용하여 2일 동안 1차 증류수를 이용하여 투석한 다음, 최종 반응물을 동결건조를 통해 건조하여 폴리에틸렌글리콜-폴리에틸렌이민-피오포바이드(pheophorbide) A 공중합체를 수득하였다.1 g of the polyethyleneglycol-polyethylenimine (mPEG-PEI) obtained above was treated with pheophorbide A (eq, 0.07 mmol), dicyclohexyl carbodiimide (DCC) (1.2 * pheophorbide A in moles) and N-hydroxysuccinylimide (HOSu; 1.2 * pheophorbide A in moles) was dissolved in 20 ml of dimethyl sulfoxide (DMSO) and stirred for 3 hours. Thereafter, the two solutions were mixed and reacted at room temperature for 24 hours. In addition, the dialysis membrane (Spectra / Por; mol. Wt. Cutoff size, 1,000) was dialyzed with primary distilled water for 2 days, and then the final reaction product was dried by lyophilization to obtain polyethylene glycol-polyethylenimine-piopho. A pheophorbide A copolymer was obtained.
1-2. 결합체(소광제 접합 콘드로이틴 설페이트)의 합성1-2. Synthesis of Binder (Quatcher Conjugate Chondroitin Sulfate)
콘드로이친 설페이트 0.1g을 20ml의 증류수에 녹였다. 건조된 DMSO에 BHQ3를 녹인 후 N-(3-디메틸아미노프로필)-N′-에틸카르보디이민 하이드로클로라이드(EDC), 4-디메틸아미노피리딘(DMAP)을 각각 BHQ의 몰비에 대해 1.5배로 첨가하였다. 이후, 두 용액을 각각 상온에서 3시간 동안 교반한 후 섞고 24시간 동안 반응시켰다. 미반응된 소광제(BHQ3)의 제거는 투석막(Spectra/Por; mol. wt. cutoff size, 1,000)을 이용하여 2일 동안 1차 증류수를 이용하여 투석함으로써 제거하였고, 투석 후 최종 반응물을 동결건조를 통해 건조시켜 소광제 접합 콘드로이틴 설페이트 결합체를 수득하였다.0.1 g of chondroitin sulfate was dissolved in 20 ml of distilled water. After dissolving BHQ3 in dried DMSO, N- (3-dimethylaminopropyl) -N'-ethylcarbodiimine hydrochloride (EDC) and 4-dimethylaminopyridine (DMAP) were each added 1.5-fold to the molar ratio of BHQ. . Then, the two solutions were each stirred at room temperature for 3 hours, then mixed and reacted for 24 hours. Removal of unreacted quencher (BHQ3) was removed by dialysis using primary distilled water for 2 days using a dialysis membrane (Spectra / Por; mol. Wt. Cutoff size, 1,000), and the final reaction product was freeze-dried after dialysis. Drying through gave a quencher conjugated chondroitin sulfate conjugate.
1-3. 공중합체 및 결합체의 합성1-3. Synthesis of Copolymers and Binders
전술한 1-1. 1-2.에서 제조된 폴리에틸렌글리콜-폴리에틸렌이민-피오포바이드(pheophorbide) A 공중합체와, 소광제 접합 콘드로이틴 설페이트 결합체를 3차 증류수에 각각 녹인 후, 질량비를 기준으로 각각 1.0:0.0, 1.0:0.3, 1.0:0.6, 1.0:1.2, 1.0:2.5, 및 1.0:5.0의 비율로 혼합하였다. 2시간 후, 상기 혼합물을 0.8㎛ 주사기 필터를 이용하여 필터링하여 나노 이온 복합체를 제조하였다.1-1. The polyethyleneglycol-polyethylenimine-pheophorbide A copolymer prepared in 1-2 and the quencher conjugated chondroitin sulfate conjugate were dissolved in tertiary distilled water, respectively, and then 1.0: 0.0 and 1.0: 0.3, 1.0: 0.6, 1.0: 1.2, 1.0: 2.5, and 1.0: 5.0 in proportions. After 2 hours, the mixture was filtered using a 0.8 μm syringe filter to prepare a nano ion composite.
2. 원료물질의 혼합2. Mixing of raw materials
아래 [표 1]의 조성에 따라 정제수, 글리세린, 원료물질을 수상으로 하고, 유화제, 다가 알콜, 고급 지방산, 오일을 유상으로 하여, 각각의 상을 80℃까지 가열하여 용해하였다. 상기 유상에 수상을 또는 수상에 유상을 천천히 첨가하면서 믹서로 균일하게 혼합하여 80℃에서 10분간 유화하였다. 상기 유화액을 70℃ 이하에서 pH 조절제로 중화한 다음 45℃로 냉각하여 원료물질의 혼합물을 수득하였다.Purified water, glycerin, and raw materials were water phases, and emulsifiers, polyhydric alcohols, higher fatty acids, and oils were used as oil phases according to the compositions shown in Table 1 below, and each phase was heated and dissolved to 80 ° C. The oil phase or the oil phase was slowly added to the water phase and uniformly mixed with a mixer to emulsify at 80 ° C for 10 minutes. The emulsion was neutralized with a pH adjuster at 70 ° C. or lower and then cooled to 45 ° C. to obtain a mixture of raw materials.
3. 여드름 치료제의 제조3. Preparation of Acne Therapeutics
45℃로 냉각하여 수득한 상기 원료물질의 혼합물에 전술한 과정으로 제조된 나노 이온 복합체를 아래 [표 1]에 나타난 바와 같이 투입한 후, 균질화하여 에멀전형 여드름 치료제를 제조하였다.Into the mixture of the raw material obtained by cooling to 45 ℃ was added to the nano-ion composite prepared by the above process as shown in Table 1 below, and then homogenized to prepare an emulsion-type acne treatment.
표 1
성분 함량(wt%)
수상 원료물질 정제수 잔량
글리세린(다가 알콜) 10
산탄검 10
유상 원료물질 폴리솔베이트80(유화제) 2
세틸알콜(고급알콜) 1
스테아린산(고급지방산) 1
디메치콘(오일) 0.5
마카다미아넛오일(오일) 1
시클로디메치콘(오일) 3
리퀴드파라핀(오일) 2
하이드로게네이티드폴리데신(오일) 10
첨가제 트리에탄올아민(pH 조절제) 적량
나노 이온 복합체 1mg/100gr이하
방부제 미량
Table 1
ingredient Content (wt%)
Award raw material Purified water Remaining amount
Glycerin (polyhydric alcohol) 10
Xanthan Gum 10
Oily raw material Polysorbate 80 (emulsifier) 2
Cetyl Alcohol (Advanced Alcohol) One
Stearic acid (high fatty acid) One
Dimethicone (oil) 0.5
Macadamia Nut Oil (Oil) One
Cyclodimethicone (oil) 3
Liquid paraffin (oil) 2
Hydrogenated Polydesine (Oil) 10
additive Triethanolamine (pH regulator) Quantity
Nano ion composite Less than 1mg / 100gr
antiseptic a very small amount
실시예 2: 젤(gel)형 여드름 치료제의 제조Example 2 Preparation of Gel-Type Acne Treatment
아래 [표 2]의 조성에 따라 정제수, 글리세린, 친수성 고분자 화합물, 에탄올을 수상으로 40℃까지 가열하여 분산하여 원료물질의 혼합물을 제조한 것을 제외하고는, 실시예 1과 동일한 방법으로 젤형 여드름 치료제를 제조하였다.According to the composition of [Table 2] below, the gel-type acne treatment agent was prepared in the same manner as in Example 1, except that a mixture of raw materials was prepared by dispersing purified water, glycerin, a hydrophilic polymer compound, and ethanol by heating to 40 ° C. in an aqueous phase. Was prepared.
표 2
성분 함량(wt%)
수상 원료물질 정제수 잔량
글리세린(다가 알콜) 10
친수성 고분자 2
에탄올 30
첨가제 　나노 이온 복합체 　1mg/100gr이하
방부제 미량
TABLE 2
ingredient Content (wt%)
Award raw material Purified water Remaining amount
Glycerin (polyhydric alcohol) 10
Hydrophilic polymer 2
ethanol 30
additive Nano ion composite Less than 1mg / 100gr
antiseptic a very small amount
실시예 3: 액상형 여드름 치료제의 제조Example 3: Preparation of Liquid Acne Treatment
아래 [표 3]의 조성에 따라 정제수, 다가 알콜, 에탄올을 수상으로 하여 원료물질의 혼합물을 제조한 것을 제외하고는, 실시예 1과 동일한 방법으로 액상형 여드름 치료제를 제조하였다.According to the composition of [Table 3] below, except that a mixture of raw materials was prepared with purified water, polyhydric alcohol, and ethanol as a water phase, a liquid acne treatment was prepared in the same manner as in Example 1.
표 3
성분 함량(wt%)
수상 원료물질 정제수 잔량
에탄올 50
다가 알콜 10
첨가제 나노 이온 복합체 1mg/100gr이하
TABLE 3
ingredient Content (wt%)
Award raw material Purified water Remaining amount
ethanol 50
Polyhydric alcohol 10
additive Nano ion composite Less than 1mg / 100gr
실시예 4: 분말형 여드름 치료제의 제조Example 4 Preparation of Powdered Acne Treatment
아래 [표 4]의 조성에 따라 스타치 또는 덱스트린, 글루코스를 부형제로 하고, 여기에 다가 알콜과 나노 이온 복합체를 함침시켜 균질화한 것을 제외하고는, 실시예 1과 동일한 방법으로 액상형 여드름 치료제를 제조하였다.According to the composition of Table 4 below, a liquid acne treatment agent was prepared in the same manner as in Example 1, except that starch, dextrin, and glucose were used as excipients, and homogenized by impregnating a polyhydric alcohol and a nano ion complex. It was.
표 4
성분 함량(wt%)
부형제 스타치 또는 덱스트린 또는 글루코스 잔량　
수상 원료물질 다가 알콜 10
첨가제 나노 이온 복합체 1mg/100gr이하
Table 4
ingredient Content (wt%)
Excipient Starch or dextrin or glucose Remaining amount
Award raw material Polyhydric alcohol 10
additive Nano ion composite Less than 1mg / 100gr
본 발명은 상기 실시예들에 한정되는 것이 아니라 서로 다른 다양한 형태로 제조될 수 있으며, 본 발명이 속하는 기술분야에서 통상의 지식을 가진 자는 본 발명의 기술적 사상이나 필수적인 특징을 변경하지 않고서 다른 구체적인 형태로 실시될 수 있다는 것을 이해할 수 있을 것이다. 그러므로 이상에서 기술한 실시예들은 모든 면에서 예시적인 것이며 한정적이 아닌 것으로 이해해야만 한다.The present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has another specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.
본 발명의 일 구현예는 인체에 무해하며 부작용을 야기하지 않는 여드름 치료용 조성물 및 이를 이용한 여드름 치료제의 제조 방법을 제공하고자 한다.One embodiment of the present invention is to provide a composition for treating acne and harmless to the human body does not cause side effects and a method for producing an acne treatment using the same.
또한, 본 발명의 일 구현예는 광학 특성과 질병 표적 특성을 갖는 광민감성 물질을 포함하는 여드름 치료용 조성물 및 이를 이용한 여드름 치료제의 제조 방법을 제공하고자 한다.In addition, an embodiment of the present invention is to provide a composition for treating acne comprising a photosensitive material having optical properties and disease target properties and a method for producing an acne treatment using the same.

Claims (8)

  1. 친수성 양이온 고분자와 광감작제가 결합된 공중합체 및 음이온성 기질 고분자와 소광제가 결합된 결합체로 구성된 광역학 치료용 나노 이온 복합체를 포함하는 여드름 치료용 조성물로서, Claims [1] A composition for treating acne comprising a photodynamic therapeutic nano ion complex composed of a copolymer in which a hydrophilic cationic polymer and a photosensitizer are combined and a combination of an anionic substrate polymer and a quencher.
    상기 공중합체는 폴리에틸렌글리콜-폴리에틸렌이민-피오포바이드(pheophorbide) A이고, The copolymer is polyethyleneglycol-polyethylenimine-pheophorbide A,
    상기 결합체는 콘드로이틴 설페이트-블랙홀 소광제(blackhole quencher, BHQ)이며, The conjugate is chondroitin sulfate-blackhole quencher (BHQ),
    상기 여드름 치료용 조성물 100그램에 대하여 상기 광역학 치료용 나노 이온 복합체를 0 초과 및 1밀리그램 이하로 포함하는 여드름 치료용 조성물.The acne treatment composition comprising more than 0 and less than 1 milligram of the photodynamic therapy nano-ionic complex with respect to 100 grams of the acne treatment composition.
  2. 제 1 항에 있어서,The method of claim 1,
    상기 여드름 치료용 조성물은 유화제 0.1-10중량%, 제1 알콜 0.1-10중량%, 제2 알콜 0.1-10중량%, 지방산 0.1-10중량%, 오일 1-40중량%, 및 잔량의 정제수를 더 포함하는 여드름 치료용 조성물.The acne treatment composition is 0.1-10% by weight of emulsifier, 0.1-10% by weight of the first alcohol, 0.1-10% by weight of the second alcohol, 0.1-10% by weight of fatty acid, 1-40% by weight of oil, and the remaining amount of purified water. Acne treatment composition further comprising.
  3. 제 2 항에 있어서,The method of claim 2,
    상기 유화제는 분자 중에 수산기(-OH), 에테르기(-O-), 아미드기(-CONH), 에스테르기(-COO-)의 구조를 가진 비이온성 계면활성제; 폴리옥시에틸렌형, 다가알콜에스테르형, 에틸렌옥사이드 및 프로필렌옥사이드 블록 공중합체, 아크릴산알킬공중합체의 폴리머릭 계면활성제; 레시틴, 라놀린, 콜레스테롤, 사포닌의 천연 계면활성제;로 이루어진 군으로부터 선택된 적어도 하나인 여드름 치료용 조성물.The emulsifier may be a nonionic surfactant having a structure of hydroxyl group (-OH), ether group (-O-), amide group (-CONH), ester group (-COO-) in the molecule; Polymeric surfactants of polyoxyethylene type, polyhydric alcohol ester type, ethylene oxide and propylene oxide block copolymers, alkyl acrylate copolymers; At least one selected from the group consisting of lecithin, lanolin, cholesterol, saponin natural surfactant for treating acne.
  4. 제 2 항에 있어서,The method of claim 2,
    상기 제1 알콜은 다가 알콜로서, 글리세린, 프로필렌글라이콜, 부틸렌글라이콜, 디프로필렌글라이콜, 폴리에틸렌글리콜, 솔비톨, 또는 이들의 조합으로 이루어진 군으로부터 선택된 적어도 하나인 여드름 치료용 조성물.The first alcohol is a polyhydric alcohol, at least one selected from the group consisting of glycerin, propylene glycol, butylene glycol, dipropylene glycol, polyethylene glycol, sorbitol, or a combination thereof.
  5. 제 2 항에 있어서,The method of claim 2,
    상기 제2 알코올은 라우릴 알콜, 세틸 알콜, 스테아릴 알콜, 세테아릴 알콜, 올레일 알콜, 베헤닐 알콜, 리놀레일 알콜, 운데실레닐 알콜, 팔미톨레일 알콜, 리놀레닐 알콜, 아라키도닐 알콜, 에루실 알코올, 또는 이들의 조합으로 이루어진 군으로부터 선택된 적어도 하나인 여드름 치료용 조성물.The second alcohol is lauryl alcohol, cetyl alcohol, stearyl alcohol, cetearyl alcohol, oleyl alcohol, behenyl alcohol, linoleyl alcohol, undecylenyl alcohol, palmitoleyl alcohol, linolenyl alcohol, arachidonyl At least one selected from the group consisting of alcohol, erucyl alcohol, or a combination thereof.
  6. 제 2 항에 있어서,The method of claim 2,
    상기 지방산은 스테아린산, 라우린산, 미리스틴산, 베헤닌산, 이소스테아린산, 올레인산, 또는 이들의 조합으로 이루어진 군으로부터 선택된 적어도 하나인 여드름 치료용 조성물.The fatty acid is at least one selected from the group consisting of stearic acid, lauric acid, myristic acid, behenic acid, isostearic acid, oleic acid, or a combination thereof.
  7. 제 2 항에 있어서,The method of claim 2,
    상기 오일은 시클로디메치콘, 디메치콘, 디에틸헥실카보네이트, 하이드로게네이티드폴리데신, 미리스테아린산 이소프로필, 리퀴드파라핀, 식물성 스쿠알란, 마카다미아넛오일, 호호바오일, 아보카도오일, 올리브오일, 동백유, 또는 이들의 조합으로 이루어진 군으로부터 선택된 적어도 하나인 여드름 치료용 조성물.The oils may be cyclodimethicone, dimethicone, diethylhexylcarbonate, hydrogenated polydesin, myritearic acid isopropyl, liquid paraffin, vegetable squalane, macadamia nut oil, jojoba oil, avocado oil, olive oil, camellia oil, or their At least one selected from the group consisting of a composition for treating acne.
  8. 제 1 항 내지 제 7 항 중 어느 한 항의 여드름 치료용 조성물을 포함하는 여드름 치료제의 제조 방법으로서,A method for producing an acne treatment comprising the composition for treating acne of any one of claims 1 to 7,
    유화제, 제1 알콜, 및 정제수를 가열하여 수상 원료물질을 제조하는 단계;Heating the emulsifier, the first alcohol, and purified water to produce an aqueous phase material;
    제1 알콜, 지방산, 및 오일을 가열하여 유상 원료물질을 제조하는 단계;Heating the first alcohol, fatty acid, and oil to produce an oily raw material;
    가열된 상기 수상 원료물질 및 상기 유상 원료물질을 혼합하는 단계;Mixing the heated aqueous phase material and the oily raw material;
    상기 혼합물을 중화한 후, 냉각하는 단계; 및Neutralizing the mixture and then cooling; And
    상기 냉각된 혼합물을 광역학 치료용 나노 이온 복합체와 균질화하는 단계Homogenizing the cooled mixture with a nano-ionic complex for photodynamic therapy
    를 포함하는 여드름 치료제의 제조 방법.Method of producing an acne treatment comprising a.
PCT/KR2014/009145 2014-09-29 2014-09-30 Composition for treating acne, and method for producing therapeutic agent for acne using same WO2016052775A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201480072497.6A CN105899206A (en) 2014-09-29 2014-09-30 Composition for treating acne, and method for producing therapeutic agent for acne using same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020140130028A KR101622545B1 (en) 2014-09-29 2014-09-29 Acne treatment composition and method for manufacturing acne treatment preparation using the same
KR10-2014-0130028 2014-09-29

Publications (1)

Publication Number Publication Date
WO2016052775A1 true WO2016052775A1 (en) 2016-04-07

Family

ID=55630793

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2014/009145 WO2016052775A1 (en) 2014-09-29 2014-09-30 Composition for treating acne, and method for producing therapeutic agent for acne using same

Country Status (3)

Country Link
KR (1) KR101622545B1 (en)
CN (1) CN105899206A (en)
WO (1) WO2016052775A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106511622A (en) * 2016-11-04 2017-03-22 深圳市婴缘健康有限公司 Infant wound repair ointment

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130007700A (en) * 2011-07-07 2013-01-21 (주)비알뷰티플레볼루션 Acne therapeutics and sebum secernent inhibitor which comprise tryptophan, and kits for photodynamic therapy containing the same
KR20130034079A (en) * 2011-09-28 2013-04-05 가톨릭대학교 산학협력단 Nano ion-complex for photodynamic theraphy comprising hydrophile cationic polymer photosensitizer derivatives and anionic polysaccharide quencher derivatives
KR20140014443A (en) * 2012-07-24 2014-02-06 국립암센터 Graphene oxide-photosensitizers complex containing disulfide linker and composition for diagonosis and therapy of canncer using the same
KR20140035565A (en) * 2012-09-14 2014-03-24 동성제약주식회사 Chlorin e6 for the treatment, prevention or improvement of acne

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130007700A (en) * 2011-07-07 2013-01-21 (주)비알뷰티플레볼루션 Acne therapeutics and sebum secernent inhibitor which comprise tryptophan, and kits for photodynamic therapy containing the same
KR20130034079A (en) * 2011-09-28 2013-04-05 가톨릭대학교 산학협력단 Nano ion-complex for photodynamic theraphy comprising hydrophile cationic polymer photosensitizer derivatives and anionic polysaccharide quencher derivatives
KR20140014443A (en) * 2012-07-24 2014-02-06 국립암센터 Graphene oxide-photosensitizers complex containing disulfide linker and composition for diagonosis and therapy of canncer using the same
KR20140035565A (en) * 2012-09-14 2014-03-24 동성제약주식회사 Chlorin e6 for the treatment, prevention or improvement of acne

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PARK, W. ET AL.: "The controlled photoactivity of nanoparticles derived from ionic interactions between a water soluble polymeric photosensitizer and polysaccharide quencher", BIOMATERIALS, vol. 32, 2011, pages 8261 - 8270, XP028277136, DOI: doi:10.1016/j.biomaterials.2011.07.023 *

Also Published As

Publication number Publication date
CN105899206A (en) 2016-08-24
KR101622545B1 (en) 2016-05-20
KR20160038132A (en) 2016-04-07

Similar Documents

Publication Publication Date Title
WO2017057784A1 (en) Dry multiple capsule type composition containing photosensitive substance for improving acne skin and method for preparing same
Zhang et al. Transferrin-mediated fullerenes nanoparticles as Fe2+-dependent drug vehicles for synergistic anti-tumor efficacy
JP4745664B2 (en) Polymer derivatives of camptothecins
EP0749982B2 (en) Antioxidant grafted polysaccharides and their uses
ES2664360T3 (en) Procedures for reducing sebum production in the skin
EP2206502B1 (en) Polymer conjugate of steroid
KR101336501B1 (en) Nano ion-complex for photodynamic theraphy comprising hydrophile cationic polymer photosensitizer derivatives and anionic polysaccharide quencher derivatives
AU2006292752A1 (en) Polymeric compositions and methods of making and using thereof
JP2003515623A (en) 6-mercapto-cyclodextrin derivative: drug-induced neuromuscular blockade recovery agent
AU2007252678A1 (en) Polymer conjugate of podophyllotoxin
KR20150082619A (en) Photoreactive derivative of hyaluronic acid, method of preparation thereof, 3d-crosslinked derivative of hyaluronic acid, method of preparation and use thereof
Wu et al. Regulating the bacterial oxygen microenvironment via a perfluorocarbon-conjugated bacteriochlorin for enhanced photodynamic antibacterial efficacy
JPWO2012067138A1 (en) Polymer derivatives of novel cytidine antimetabolites
CN113663079B (en) Carrier-free self-assembly nano particle and preparation method and application thereof
CN114748639B (en) Photosensitizer-hydroxyalkyl starch-polypeptide coupled amphiphilic macromolecular compound, nano drug-loading system and preparation method thereof
WO2017200218A1 (en) Self-assembled nanocomposite based on supramolecular interaction, comprising albumin, method for producing same and use thereof
WO2016052775A1 (en) Composition for treating acne, and method for producing therapeutic agent for acne using same
KR20090080046A (en) Compositions and methods for ph targeted drug delivery
Liu et al. Self-assembling nanoarchitectonics of size-controllable celastrol nanoparticles for efficient cancer chemotherapy with reduced systemic toxicity
WO2016052774A1 (en) Composition for treating tinea pedis, and method for producing therapeutic agent for tinea pedis using same
KR100348380B1 (en) Antitumor Mitoxanthrone Polymer Composition
KR101736147B1 (en) Dry multiple encapsulated composition containing photosensitizer for improvement of athlete's foot and preparation thereof
WO2006096572A1 (en) Ethambutol based nitric oxide donors
WO2017222108A1 (en) Antibacterial liposome composition containing conjugate of pheophorbide a and lipid derivative of polyethylene glycol
CN115003703A (en) Hyaluronic acid derivatives

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 14903084

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 14903084

Country of ref document: EP

Kind code of ref document: A1