CN105899206A - 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 PDFInfo
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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
Technical field
The present invention relates to acne treatment compositions and utilize its preparation method of acne therapeutic agent.
Background technology
Although dermatosis does not affect life, but occurrence frequency is high, for modern because of a variety of causes and weather,
Pressure etc. and there is the trend that occurrence frequency gradually uprises.
Especially, the difficult dermatosis that acne causes as the infection by fungus and antibacterial, thus need long-term
The course for the treatment of, and be not easy treatment.
For the method treating acne, there is following prescription: injection suppresses the hormone agent of sebum generation, antibiosis
Agent.Although these methods have certain effect to prevention and the treatment of acne, but in gratifying effect
On in aspect or in terms of cutaneous safety, the problem that there is side effect.
Especially, in the case of hormone agent, if Long-term taking medicine, then can cause skin erythema or be dried and wait secondary work
With, benzoyl peroxide (benzoyl peroxide) and tretinoin (Retinoic acid) as biocide are deposited
In problem that is carcinogenic and that cause contact dermatitis.Additionally, as acne therapeutic agent by using tetracycline
(tetracyclin), erythromycin (erythromycin) and clindamycin (clindamycin) obtain effect,
But, it was reported that be likely to be of the appearance etc. of Drug resistance bacterium, the most in use on there may be limitation.
On the other hand, photodynamic therapy (photodynamic therapy, PDT) refers to, for various diseases
Become, utilize the photosensitizer (photosensitizer) with selectivity and light monotonicity, it is not necessary to perform an operation and just can control
Treat the most chemotherapeutic radical cure of one of pathological changes.Such as, intravenous injection is utilized to inject described photosensitizer to object,
And hitherward irradiate suitable light (light), so that photosensitizer carries out activation to oxygen molecule, thus change
Become singlet (singlet) oxygen or form new atomic group (radical), and then only pathological changes optionally being entered
Row is attacked and is allowed to eliminate.
As these photosensitizer, the representational compound having porphyrin (porphyrin) class, it is reported, from silkworm
The porphyrins that husky or Folium Mori, green algae etc. are extracted has the spectroscopic properties being suitable as photosensitizer, profit
By the stronger HONGGUANG (700~900nm) of Premeabilisation of cells rate, the character causing electron transfer can be efficiently generated
With thing followed excited state.
Summary of the invention
It is an object of the invention to provide acne treatment that is a kind of harmless and that do not cause side effect to combine
Thing and utilize its preparation method of acne therapeutic agent.
Further, another object of the present invention is to provide have optical signature and disease targets feature a kind of comprising
The acne treatment compositions of photosensitizer and utilize its preparation method of acne therapeutic agent.
One embodiment of the invention provides acne treatment compositions, comprises photodynamic therapy nanoparticle multiple
Zoarium, described photodynamic therapy nanoparticle complex is by combining hydrophilic cationic macromolecule and photosensitive
The copolymer of agent and combine the coalition of anionic property substrate macromolecule and quencher and constituted, wherein, described
Copolymer is PEG-PEI-phoeophorbide salt (pheophorbide) A, and described coalition is
Chondroitin sulfate-black hole quencher (blackhole quencher, BHQ), relative to described acne treatment group
Compound 100 grams, comprises the described photodynamic therapy nanoparticle complex more than less than 0 and 1 milligram.
Described acne treatment compositions can also comprise emulsifying agent, 0.1~10 of 0.1~10 percentage by weights
First alcohol of percentage by weight, 0.1~10 second alcohol, 0.1~10 fat of percentage by weight of percentage by weight
Acid, 1~40 oily and remaining Purified Waters of percentage by weight.
Described emulsifying agent can be by having hydroxyl (-OH), ether (-O-), amide groups in the molecule
(-CONH), the nonionic surfactant of ester group (-COO-) structure;Polyoxyethylene ene-type, polynary
Alcohol ester type, oxirane and propylene oxide block copolymer, the polymerizable surface active of alkyl acrylate copolymer
Agent;And the natural surfactant of lecithin, lanoline, cholesterol, saponin;The group formed enters
At least one of row selection.
Described first alcohol is polyhydric alcohol, can be from by glycerol, propylene glycol, butanediol, dipropylene glycol, poly-second
The group that glycol, sorbitol or combinations thereof are constituted carries out at least one selected.
Described second alcohol, can be from by lauryl alcohol, spermol, stearyl alcohol, cetearyl alcohol, oleyl alcohol, mountain
Yu alcohol, linolenyl alcohol (linoleyl alcohol), undecylenic alcohol, Palmitoleyl alcohol (Palmitoleyl alcohol),
Linolenyl alcohol (linolenyl alcohol), arachidic alcohol (arachidonyl alcohol), erucyl alcohol or they
The group that combination is constituted carries out at least one selected.
Described fatty acid can be from by stearic acid, lauric acid, myristic acid, behenic acid, isostearic acid, oil
The group that acid or combinations thereof are constituted carries out at least one selected.
Described oil, can be from by Cyclomethicone, polydimethylsiloxane, diethyl hexylcarbonate,
Hydrogenated polydecene, isopropyl myristate (myristearate isopropyl), liquid paraffin, plant squalane,
The group that macadimia nut oil, Jojoba oil, American Avocado Tree oil, olive oil, Camellia oil or combinations thereof are constituted enters
At least one of row selection.
Further, another embodiment of the present invention offer comprises the acne therapeutic agent of aforementioned acne treatment compositions
Preparation method, described method includes: heats emulsifying agent, the first alcohol and Purified Water, thus prepares water
The step of phase raw material;First alcohol, fatty acid and oil are heated, thus prepares oil phase raw material
Step;The step that the described Aqueous Phase Raw Material material heated and described oil phase raw material are mixed;To institute
State after mixture is neutralized, the step of cooling;And to the mixture of described cooling and photodynamic therapy
The step homogenized is carried out with nanoparticle complex.
According to one embodiment of the invention, it is possible to provide harmless and do not cause the acne treatment group of side effect
Compound and utilize its preparation method of acne therapeutic agent.
Further, according to one embodiment of the invention, it is possible to provide owing to comprising, there is optical signature and disease targets spy
The photosensitizer levied and the acne treatment that can apply to photodynamic therapy (photodynamic therapy, PDT)
By compositions and the preparation method of the acne therapeutic agent utilizing it.
Detailed description of the invention
Hereinafter, embodiments of the invention are described in detail.But this is only used as example and proposes, the present invention does not limit to
In this, the present invention is defined according only to the scope of claim.
One embodiment of the invention provides a kind of acne treatment compositions, and described acne treatment compositions comprises
Photodynamic therapy nanoparticle complex, described photodynamic therapy nanoparticle complex is by combining
Hydrophilic cationic macromolecule and the copolymer of photosensitizer and combine anionic property substrate macromolecule and quencher
Coalition constituted, wherein said copolymer is PEG-PEI-phoeophorbide salt
(Pheophorbide) A, described coalition be chondroitin sulfate-black hole quencher (blackhole quencher,
BHQ), relative to described acne treatment compositions 100 grams, comprise more than described in less than 0 and 1 milligram
Photodynamic therapy nanoparticle complex.
Described hydrophilic cationic macromolecule, can rely ammonia from by glycol-chitosan, chitosan, how poly-L-
Acid (PLL), poly-β amino ester macromolecule, polymine (PEI), polyamidoamine dendroid high score
The group that son (PAMAM) and their derivant are formed selects and uses.Described hydrophilic sun
Ion macromolecule, can form ion complex with anionic property substrate macromolecule described later according to electrostatic attraction and receive
Rice corpuscles.
Such as, described hydrophilic cationic macromolecule can comprise Polyethylene Glycol and polymine.
Now, described Polyethylene Glycol (PEG) has and shows as HO-(CH2CH2O) structural formula of n-H,
In this case, its architectural feature is to have the oxirane ((CH repeatedly connected2CH2O)-), therefore behave as
Strongly hydrophilic.Further, these features, in the case of combining with protein or compound, have imparting biology
The feature of the compatibility.
And, Polyethylene Glycol with side end by methoxyl group (CH3O-) methoxy poly (ethylene glycol) replaced
(mPEG) form exists, and its structural formula is CH3O-(CH2CH2O)n-H.Especially, there is poly-second two
In the case of the preparation of alcohol-protein form, methoxy poly (ethylene glycol) is used to derive as Polyethylene Glycol major part
Thing.Its reason is that the end of Polyethylene Glycol is protected by methoxyl group, so the stability of structure can be maintained.
In one embodiment of this invention, Polyethylene Glycol can be molecular weight be 300 to 50,000, end has
The Polyethylene Glycol of carboxyl.Further, Polyethylene Glycol can be the poly-second of methoxyl group that side end is replaced by methoxyl group
Glycol.
On the other hand, described polymine is the cationic polymer electrolytic used in field of papermaking already
Matter.Generally, polymine is divided into line style and branched chain type according to its structure, and both synthetic methods are different.
The polymine typically used is branched chain type, wherein, primary amine, secondary amine, tertiary amine number with 12
The ratio of 1 exists.It is reported that every 3~3.5 backbone nitrogen atom exist the poly-second of branched chain type of about one
The side chain of alkene imines, this kind of polymine can be dissolved in water, alcohol, ethylene glycol, dimethylformamide, tetrahydrochysene
Furan, esters etc., but it is not dissolved in the hydro carbons of high molecular, oleic acid (oleic acid), ether.
Such as, described polymine can use and not have virose branched chain type polymine, polymine
Molecular weight less than 100 time, the copolymer generated according to the present invention, it is impossible to biological live with useful well
Property material combine, and molecular weight more than 25,000 time, have and be difficult in vivo by asking that kidney excretes
Topic.Therefore, the molecular weight of polymine can be 100 to 25,000, it is preferable that molecular weight can be 100
To 2000.
Described photosensitizer, can be from by porphyrin (phorphyrins) compound, chlorin class (chlorins)
Compound, porphine of bacterium class (bacteriochlorins) compound, phthalocyanines (phtalocyanine) compound,
Naphthalene phthalocyanines (naphthalocyanines) compound and 5-ALA ester (5-aminoevuline
Esters) group that compound is formed selects and use.Such as, described photosensitizer can be chlorin
E6 (Chlorin e6), Phthalocyanine Zinc (Zinc Phthalocyanine) or phoeophorbide salt (Pheophorbide)
A。
Described coalition is constituted with the form combining quencher at anionic property substrate macromolecule.
More specifically, anionic property substrate macromolecule, can be from by chrondroitin-6-sulfate (C6S), sulphuric acid
Heparan (HS), heparan sulfate proteoglycan (HSPG), heparin, chrondroitin-4-sulfate (C4S),
Chrondroitin-6-sulfate (C6S), dermatan sulfate (DS), keratan sulfate (KS) and hyalomitome
The group that acid (HA) is formed selects and uses.
Described quencher, can be from by black hole quencher (blackhole quencher), blackberry quencher
The group that (blackberry quencher, BBQ) and their derivant are formed selects and uses.
Thus, the present invention has a characteristic that and utilizes cationic macromolecule, i.e. hydrophilic cationic is high
Molecule, to have hydrophobic photosensitizer give hydrophilic, thus be readily dissolved in when optical therapeutic solution or
In water, the most do not produce precipitate.
On the other hand, acne treatment compositions according to an embodiment of the invention, it is also possible to comprise 0.1~10
The emulsifying agent of percentage by weight, 0.1~10 percentage by weight the first alcohol, 0.1~10 percentage by weight second
Alcohol, 0.1~10 fatty acid, 1~40 oily and remaining Purified Waters of percentage by weight of percentage by weight.When
When the content of described emulsifying agent, first and second alcohol, fatty acid, oil and Purified Water is described scope, utilize
The effect of the acne therapeutic agent of acne treatment compositions can more be improved.
More specifically, described emulsifying agent can be by have in the molecule hydroxyl (-OH), ether (-O-),
Amide groups (-CONH), the nonionic surfactant of ester group (-COO-) structure;Polyoxyethylene ene-type,
Polyhydric alcohol ester type, oxirane and propylene oxide block copolymer, the polymeric surface of alkyl acrylate copolymer
Activating agent;And the natural surfactant of lecithin, lanoline, cholesterol, saponin;The group formed
In carry out at least one that select.
Described first alcohol can be from by glycerol, propylene glycol, butanediol, dipropylene glycol, poly-second as polyhydric alcohol
The group that glycol, sorbitol or combinations thereof are constituted carries out at least one selected.
Described second alcohol, can be from by lauryl alcohol, spermol, stearyl alcohol, cetearyl alcohol, oleyl alcohol, mountain
Yu alcohol, linolenyl alcohol (linoleyl alcohol), undecylenic alcohol, Palmitoleyl alcohol (Palmitoleyl alcohol),
Linolenyl alcohol (linolenyl alcohol), arachidic alcohol (arachidonyl alcohol), erucyl alcohol (erucyl alcohol)
Or the group that constituted of combinations thereof carries out at least one selected.
Described fatty acid, can be from by stearic acid, lauric acid, myristic acid, behenic acid, isostearic acid,
The group that oleic acid or combinations thereof are constituted carries out at least one selected.
Described oil, can be from by Cyclomethicone (cyclo dimethicone), poly dimethyl silicon
Oxygen alkane (dimethicone), diethyl hexylcarbonate (Diethylhexyl carbonate), hydrogenated polydecene
(Hydrogenated Polydecene), isopropyl myristate (MyriStearate isopropyl), liquid
Paraffin (Liquid paraffin), plant squalane, macadimia nut oil, Jojoba oil, American Avocado Tree oil, olive oil,
The group that Camellia oil or combinations thereof are constituted carries out at least one selected.
One more embodiment of the present invention relates to the preparation comprising the acne therapeutic agent of aforementioned acne treatment compositions
Method, the preparation method of the acne therapeutic agent provided includes: add emulsifying agent, the first alcohol and Purified Water
Heat, thus prepare the step of Aqueous Phase Raw Material material;First alcohol, fatty acid and oil are heated, thus prepares
The step of oil phase raw material;Described Aqueous Phase Raw Material material and described oil phase raw material to being heated mix
The step closed;After described mixture is neutralized, the step of cooling;And the mixture to described cooling
The step that homogenizes is carried out with photodynamic therapy nanoparticle complex.
Further, another embodiment of the present invention relates to prepared by the preparation method according to aforesaid acne therapeutic agent
Acne therapeutic agent, it is provided that emulsion-type, gel (gel) type, liquid phase type or the acne therapeutic agent of powder-type.
Hereinafter, embodiments of the invention and comparative example are described.But, following example are only the one of the present invention
Embodiment, the invention is not limited in below example.
Embodiment
Embodiment 1: the preparation of emulsion-type acne therapeutic agent
1. the preparation of nanoparticle complex
The synthesis of 1-1. copolymer (PEG-PEI-photosensitizer)
After reflux condenser is set, utilize the flask methoxy poly (ethylene glycol) by 10g of 250ml
(mPEG-COOH) (sigma, 5000Da) is dissolved in the dichloromethane (CHCl of 50ml2).Afterwards,
Add N-hydroxy-succinamide (N-hydroxysuccinylimide) and the dicyclo carbonization of 0.74g of 0.52g
After diimine (dicyclocarbodiimide), reaction 20 hours at normal temperatures.Two are removed through filter process
After cyclohexyl urea (Dicyclohexylurea), it is deposited in ether (diethylether), thus obtains work
The Polyethylene Glycol (mPEG-NHS) of property form.
The 2g Polyethylene Glycol of described acquirement is dissolved in the chloroform of 200ml.Afterwards, by the polyethylene of 0.5g
Imines (Alfa Aesar, 1800da) is dissolved in the chloroform of 50ml, then little by little instills dissolving herein
There is the solution of described Polyethylene Glycol, thus perform the covalent reaction of Polyethylene Glycol and polymine.
Here, described reaction is carried out 24 hours, after reaction terminates, utilize vacuum concentrating apparatus, be condensed into total
Volume is 30ml, is then deposited in ether (diethylether), thus obtains Polyethylene Glycol and polyethyleneimine
The total coalition of amine.
By the 1g PEG-PEI (mPEG-PEI) of described acquirement, phoeophorbide salt
(pheophorbide) A (e.q., 0.07mmol), dicyclohexylcarbodiimide (dicyclohexyl
Carbodiimide, DCC) (1.2*pheophorbide A in moles) and N-hydroxy-succinamide
(N-hydroxysuccinylimide)(HOSu;1.2*pheophorbide A in moles), respectively at 20ml
Dimethyl sulfoxide (dimethyl sulfoxide, DMSO) in dissolve after stir 3 hours.Then, mix respectively
After closing two solution, reaction 24 hours at normal temperatures.Further, dialyser (Spectra/Por is utilized;mol.wt.
Cutoff size, 1,000), after utilizing the dialysis that one-level distilled water carries out 2 days, by lyophilization to
End reaction thing is dried, thus obtains PEG-PEI-phoeophorbide salt (pheophorbide)
A copolymer.
The synthesis of 1-2. coalition (quencher joint chondroitin sulfate)
0.1g chondroitin sulfate is dissolved in the distilled water of 20ml.BHQ3 is dissolved in the DMSO through being dried
Afterwards, with the addition of respectively the N-that mol ratio is 1.5 times (3-the DimethylAminopropyl)-N ' relative to BHQ-
Ethyl-carbodiimide hydrochloride (EDC), DMAP (DMAP).Afterwards, at normal temperatures,
After two solution stirring 3 hours, mix, and react 24 hours.For unreacted quencher
Removal, be to utilize dialyser (Spectra/Por;Mol.wt.cutoff size, 1,000), utilize one-level to distill
Water carries out the dialysis of 2 days and is removed, and after dialysis, utilizes lyophilization to be dried end reaction thing,
Thus obtain quencher and engage chondroitin sulfate coalition.
1-3. copolymer and the synthesis of coalition
In three-stage distillation water, it is dissolved in aforesaid 1-1., 1-2. the polyethylene glycol second of preparation respectively
After alkene imines-phoeophorbide salt A copolymer and quencher engage chondroitin sulfate coalition, with mass ratio
On the basis of, respectively with 1.0 0.0,1.0 0.3,1.0 0.6,1.0 1.2,1.0 2.5 and 1.0 5.0
Ratio mix.After 2 hours, utilize 0.8 μm injection filter that described mixture is carried out
Filter, thus prepare nanoparticle complex.
2. the mixing of raw material
According to such as the combination of table 1 below, Purified Water, glycerol, raw material are made for aqueous phase, by emulsifying agent,
Polyhydric alcohol, higher fatty acids, oil are made for oil phase, and respective heat phase to 80 DEG C are dissolved.?
While described oil phase being slowly added into aqueous phase or being slowly added into oil phase in aqueous phase, utilize blender equably
Mixing, and emulsifying 10 minutes at a temperature of 80 DEG C.Utilize pH adjusting agent to institute at a temperature of below 70 DEG C
State after emulsion is neutralized, be cooled to 45 DEG C, thus obtain the mixture of raw material.
3. the preparation of acne therapeutic agent
In the mixture of the described raw material being cooled to 45 DEG C and obtain, by as shown in table 1 below, add
After the nanoparticle complex prepared by aforementioned process, carry out homogenizing and preparing emulsion-type acne and control
Treat agent.
Table 1
Embodiment 2: the preparation of gel (gel) type acne therapeutic agent
According to such as the combination of table 2 below, by Purified Water, glycerol, hydrophilic macromolecular compounds, ethanol with aqueous phase
Be heated to 40 DEG C and disperse, thus preparing the mixture of raw material, in addition, according to embodiment 1
Identical method is prepared for gel-type acne therapeutic agent.
Table 2
Embodiment 3: the preparation of liquid phase type acne therapeutic agent
According to such as the combination of table 3 below, Purified Water, polyhydric alcohol, ethanol are prepared the mixed of raw material with aqueous phase
Compound, in addition, is prepared for liquid phase type acne therapeutic agent according to method same as in Example 1.
Table 3
Embodiment 4: the preparation of powder-type acne therapeutic agent
According to such as the combination of table 4 below, using starch, dextrin or glucose as excipient, dipping polyhydric alcohol at this
With nanoparticle complex, homogenize, in addition, be prepared for according to method same as in Example 1
Powder-type acne therapeutic agent.
Table 4
The invention is not limited in previous embodiment, but can prepare in other various modes, as long as this
Bright those of ordinary skill in the field, it is possible to understand and do not changing technological thought or the essential feature of the present invention
In the case of, can be to be deformed into other concrete modes.It is therefore to be understood that the above multiple embodiments recorded exist
All aspects are considered as exemplary, and non-limiting.
Industrial applicability
One embodiment of the invention provide harmless and do not cause side effect acne treatment compositions and
Utilize the preparation method of its acne therapeutic agent.
Further, one embodiment of the invention provides and comprises the photosensitizer with optical signature and disease targets feature
Acne treatment compositions and utilize its preparation method of acne therapeutic agent.
Claims (8)
1. an acne treatment compositions, comprises photodynamic therapy nanoparticle complex, described light
Photodynamic therapy nanoparticle complex is by the copolymer combining hydrophilic cationic macromolecule and photosensitizer
And the coalition combining anionic property substrate macromolecule and quencher is constituted, it is characterised in that
Described copolymer is PEG-PEI-phoeophorbide salt A,
Described coalition is chondroitin sulfate-black hole quencher,
Relative to described acne treatment compositions 100 grams, comprise the described light more than less than 0 and 1 milligram and move
Nanoparticle complex is used in mechanics treatment.
Acne treatment compositions the most according to claim 1, it is characterised in that described acne treatment
Also comprise by compositions the emulsifying agent of 0.1~10 percentage by weights, 0.1~10 percentage by weight the first alcohol,
Second alcohol of 0.1~10 percentage by weights, 0.1~10 fatty acid, 1~40 percentage by weights of percentage by weight
Oily and remaining Purified Water.
Acne treatment compositions the most according to claim 2, it is characterised in that described emulsifying agent is
By having hydroxyl, ether, amide groups, the nonionic surfactant of ester group structure in the molecule;Polyoxygenated
Ethylene type, polyhydric alcohol ester type, oxirane and propylene oxide block copolymer, alkyl acrylate copolymer
Polymeric surfactant;And the natural surfactant of lecithin, lanoline, cholesterol, saponin;Institute
The group of composition carries out at least one selected.
Acne treatment compositions the most according to claim 2, it is characterised in that described first alcohol is
Polyhydric alcohol, from by glycerol, propylene glycol, butanediol, dipropylene glycol, Polyethylene Glycol, sorbitol or they
The group that combination is constituted carries out at least one selected.
Acne treatment compositions the most according to claim 2, it is characterised in that described second alcohol is
From by lauryl alcohol, spermol, stearyl alcohol, cetearyl alcohol, oleyl alcohol, behenyl alcohol, linolenyl alcohol, hendecene
The group that alcohol, Palmitoleyl alcohol, linolenyl alcohol, arachidic alcohol, erucyl alcohol or combinations thereof are constituted selects
At least one.
Acne treatment compositions the most according to claim 2, it is characterised in that described fatty acid is
Constituted from by stearic acid, lauric acid, myristic acid, behenic acid, isostearic acid, oleic acid or combinations thereof
Group in carry out at least one that select.
Acne treatment compositions the most according to claim 2, it is characterised in that described oil be from by
Cyclomethicone, polydimethylsiloxane, diethyl hexylcarbonate, hydrogenated polydecene, myristic acid
Isopropyl ester, liquid paraffin, plant squalane, macadimia nut oil, Jojoba oil, American Avocado Tree oil, olive oil, mountain
The group that Oleum Camelliae or combinations thereof are constituted carries out at least one selected.
8. a preparation method for acne therapeutic agent, comprises the Cuo described in any one in claim 1 to 7
Skin ulcer therapeutic composition, it is characterised in that the preparation method of described acne therapeutic agent includes:
Emulsifying agent, the first alcohol and Purified Water are heated, thus prepares the step of Aqueous Phase Raw Material material;
First alcohol, fatty acid and oil are heated, thus prepares the step of oil phase raw material;
The step that the described Aqueous Phase Raw Material material heated and described oil phase raw material are mixed;
After described mixture is neutralized, the step of cooling;And
The step that the mixture of described cooling is homogenized with photodynamic therapy nanoparticle complex.
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KR10-2014-0130028 | 2014-09-29 | ||
KR1020140130028A KR101622545B1 (en) | 2014-09-29 | 2014-09-29 | Acne treatment composition and method for manufacturing acne treatment preparation using the same |
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 |
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CN106511622A (en) * | 2016-11-04 | 2017-03-22 | 深圳市婴缘健康有限公司 | Infant wound repair ointment |
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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 |
KR101308507B1 (en) * | 2011-07-07 | 2013-09-17 | (주)비알뷰티플레볼루션 | Acne therapeutics and sebum secernent inhibitor which comprise tryptophan, and kits for photodynamic therapy containing the same |
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 |
-
2014
- 2014-09-29 KR KR1020140130028A patent/KR101622545B1/en active IP Right Grant
- 2014-09-30 CN CN201480072497.6A patent/CN105899206A/en active Pending
- 2014-09-30 WO PCT/KR2014/009145 patent/WO2016052775A1/en active Application Filing
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KR101308507B1 (en) * | 2011-07-07 | 2013-09-17 | (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 |
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CN106511622A (en) * | 2016-11-04 | 2017-03-22 | 深圳市婴缘健康有限公司 | Infant wound repair ointment |
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KR20160038132A (en) | 2016-04-07 |
KR101622545B1 (en) | 2016-05-20 |
WO2016052775A1 (en) | 2016-04-07 |
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