CN101177438B - N-acetylglucosamine derivatives and use thereof - Google Patents
N-acetylglucosamine derivatives and use thereof Download PDFInfo
- Publication number
- CN101177438B CN101177438B CN2007101823114A CN200710182311A CN101177438B CN 101177438 B CN101177438 B CN 101177438B CN 2007101823114 A CN2007101823114 A CN 2007101823114A CN 200710182311 A CN200710182311 A CN 200710182311A CN 101177438 B CN101177438 B CN 101177438B
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- Prior art keywords
- general formula
- compound
- acid
- glucosamine
- acetyl
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- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 125000002252 acyl group Chemical group 0.000 claims abstract description 12
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- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims description 49
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 claims description 49
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- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 10
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
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- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
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- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical class CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- XMXOIHIZTOVVFB-JIZZDEOASA-L disodium;(2s)-2-aminobutanedioate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CC([O-])=O XMXOIHIZTOVVFB-JIZZDEOASA-L 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 239000010696 ester oil Substances 0.000 description 1
- 210000002744 extracellular matrix Anatomy 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- SJWWTRQNNRNTPU-ABBNZJFMSA-N fucoxanthin Chemical compound C[C@@]1(O)C[C@@H](OC(=O)C)CC(C)(C)C1=C=C\C(C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)C(=O)C[C@]1(C(C[C@H](O)C2)(C)C)[C@]2(C)O1 SJWWTRQNNRNTPU-ABBNZJFMSA-N 0.000 description 1
- AQLRNQCFQNNMJA-UHFFFAOYSA-N fucoxanthin Natural products CC(=O)OC1CC(C)(C)C(=C=CC(=CC=CC(=CC=CC=C(/C)C=CC=C(/C)C(=O)CC23OC2(C)CC(O)CC3(C)C)C)CO)C(C)(O)C1 AQLRNQCFQNNMJA-UHFFFAOYSA-N 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
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- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
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- 238000012423 maintenance Methods 0.000 description 1
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- 239000011159 matrix material Substances 0.000 description 1
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- 229940057061 mevalonolactone Drugs 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
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- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000010466 nut oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000008845 photoaging Effects 0.000 description 1
- 235000002378 plant sterols Nutrition 0.000 description 1
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
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- GGHPAKFFUZUEKL-UHFFFAOYSA-N sodium;hexadecyl hydrogen sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS(O)(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-N 0.000 description 1
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Images
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Abstract
The present invention relates to an acetylated N-acetylglucosamine derivative represented by the following general formula (1), and a hyaluronic acid production promoter and an external preparation for skin containing the same. General formula (1)
(wherein, R1Is a hydrogen atom or an alkyl group having 2 to 18 carbon atoms; r2、R3And R4The acyl groups are hydrogen atoms or acyl groups with 2-18 carbon atoms, which can be the same or different; the 1-position steric structure may be either α or β; however, R1、R2、R3、R4Not all hydrogen atoms). Can maintain the tension and the luster of the skin by promoting the generation of hyaluronic acid of the skin,as a result, a hyaluronic acid production promoter and an external skin preparation which are expected to prevent aging of human skin and are easily available can be provided.
Description
The application is that application number is the dividing an application for the PCT international application of " N-acetyl-glucosamine verivate and uses thereof " that 03824086.6 (PCT/JP2003/009428), the applying date be on July 25th, 2003, denomination of invention.
Technical field
Short agent or the external composition for skin of generating of mucinase that the present invention relates to the N-acetyl-glucosamine verivate and contain this compound.Can provide a kind of through the present invention and can keep the tension force of skin or moist external composition for skin.
Background technology
Mucinase is the macromolecule polysaccharide with high moisture hold facility; (the wine well enters I, too youth, " mucinase metabolism and the wrinkle formation " of aboveground gentry, " Fragrance Journal ", Fragrance Journal society even in skin, also get most of the attention as important extracellular matrix components; Distribution on April 15th, 1998; The 26th volume, No. 4,49～58 pages).
Also have; Known mucinase have keep cell, the oilness that keeps skin and flexibility, relatively external force such as mechanical damage resistibility, prevent multiple function (" BIOINDUSTRY " such as infectation of bacteria; CMC Co., Ltd., distribution on May 1st, 1991, the 8th volume; No. 5,66 (346)-68 (346) pages).
On the other hand, there is report to claim aging decline (Ludger J.M.Meyer and Robert Stern, " the Age-Dependent Changes ofHyaluronan in Human Skin " that can cause the mucinase staining power between epidermic cell; " The Journal of Investigative Dermatology ", The Society for Investigative Dermatology, INC.; In April, 1994, Vol.102, No.4,385-389 page or leaf); And the mucinase of solar elastosis (solarelastosis) portion that is caused by uviolizing almost can not detect the tall and erect husband of Tsuji, " physiological ageing of skin: with the difference of photoaging ", " clinical Dermatology Department "; Medical science academy; Distribution on April 15th, 1997 increases number of the edition the 51st volume, No. 5; The 53-57 page or leaf), its result can cause xerosis cutis, tension force, elastic decline and then be the increase of wrinkle.In order to improve this state, what taked is to have cooperated the method for hyaluronic makeup with the moisture retention of maintenance skin surface through applying in the past, but is difficult to see through skin as high molecular mucinase, so can't fundamentally improve.Therefore, need develop the material that fundamentally improves skin function through improving the hyaluronic synthesis capability that cell self had.
As the short material that generates of the mucinase in the epidermis, known have a vitamin A acid, and it just is present in the epidermis originally, is with the propagation of epidermic cell or breaks up relevant material.But, have skin irritation from vitamin A acid, therefore hope to find the short material that generates of the mucinase that can avoid this point.
On the other hand, there is report to be referred to as the hyaluronic N-acetyl-glucosamine that constitutes sugar when concentration is 5mmol/L, can promotes to cultivate the hyaluronic growing amount of epidermic cell, it is reached about 1.5 times, and this point and cell proliferation are irrelevant.(" fine chemical (fine chemical) ", CMC Co., Ltd., distribution on December 15 calendar year 2001, the 30th volume, No. 22,5-11 page or leaf).But N-acetyl-glucosamine in order in fields such as makeup or medicine, to use more widely, finds lower concentration also can demonstrate the material of effect of sufficient even hope if the short effect that generates of the matter acid that will show transparency just needs high density.
Summary of the invention
Therefore, the objective of the invention is to, provide through promote hyaluronic generation can keep skin tension force or moist and improve wrinkle, effect is higher than the short agent and the external composition for skin of generating of mucinase of N-acetyl-glucosamine.
For this reason; The inventor etc. are in view of above-mentioned situation, concentrate on studies to solving in the past the method for problem, and the result finds; Stating specific compound after the utilization can be easy as can and promote the mucinase in epidermis and the corium to generate strongly, thereby has accomplished the present invention.
That is, the present invention is for the N-acetyl-glucosamine verivate of formula (1) expression, with external composition for skin that to contain this N-acetyl-glucosamine verivate be characteristic, with the short generation of the mucinase agent that is effective constituent of this N-acetyl-glucosamine verivate.
General formula (1)
(wherein, R
1Be that Wasserstoffatoms or carbonatoms are 2～18 alkyl.R
2, R
3And R
4Be that Wasserstoffatoms or carbonatoms are 2～18 acyl group, can be identical all, also can there be different groups.In addition, 1 D structure can be any among α or the β.But, R
1, R
2, R
3, R
4Can not all be Wasserstoffatoms).
In addition, preferably use formula (2) or (3) expression the N-acetyl-glucosamine verivate, generate agent with external composition for skin that to contain this N-acetyl-glucosamine verivate be characteristic, with this N-acetyl-glucosamine verivate mucinase that is effective constituent is short.
General formula (2)
(wherein, R
5Be that carbonatoms is 2～18 alkyl.R
6Be Wasserstoffatoms or ethanoyl.In addition, 1 D structure can be any among α or the β).
General formula (3)
(wherein, R
7Be that Wasserstoffatoms or carbonatoms are 2～18 alkyl.R
8Be that carbonatoms is 2～18 acyl group.In addition, 1 D structure can be any among α or the β).
As with above-mentioned general formula (1), the perhaps N-acetyl-glucosamine verivate of (2) or (3) expression, can specifically enumerate the compound of representing with formula (4)～(15).
General formula (4)
(1 D structure can be any among α or the β).
General formula (5)
(1 D structure can be any among α or the β).
General formula (6)
(1 D structure can be any among α or the β).
General formula (7)
(1 D structure can be any among α or the β).
General formula (8)
(1 D structure can be any among α or the β).
General formula (9)
(1 D structure can be any among α or the β).
General formula (10)
(1 D structure can be any among α or the β).
General formula (11)
(1 D structure can be any among α or the β).
General formula (12)
(1 D structure can be any among α or the β).
General formula (13)
(1 D structure can be any among α or the β).
General formula (14)
(1 D structure can be any among α or the β).
General formula (15)
(1 D structure can be any among α or the β).
Also have, the present invention relates to short agent, the external composition for skin of generating of a kind of mucinase, it is characterized in that, with the N-acetyl-glucosamine verivate of formula (16) expression as effective constituent.
General formula (16)
(wherein, R
9Be that carbonatoms is 2～16 acyl group.In addition, 1 D structure can be any among α or the β).
As N-acetyl-glucosamine verivate, can specifically enumerate compound with formula (17) expression with above-mentioned general formula (16) expression.
General formula (17)
(1 D structure can be any among α or the β).
Description of drawings
Fig. 1 is the short figure that generates the result of test (Test Example 1) of mucinase that the epidermic cell of making example 1～3 and 6～8 has been adopted in expression.
Fig. 2 is the short figure that generates the result of test (Test Example 1) of mucinase that the epidermic cell of making example 4 and 5 has been adopted in expression.
Fig. 3 is that manufacturing example 9～12,2-acetamido-1,3,4 have been adopted in expression, the short figure that generates the result of test (Test Example 2) of the mucinase of the epidermic cell of 6-four-O-ethanoyl-2-deoxidation-β-D-glycopyranoside [compound of general formula (17)].
Fig. 4 is the short figure that generates the result of test (Test Example 3) of mucinase that the dermal cell of making example 1 and 6 has been adopted in expression.
Embodiment
The N-acetyl-glucosamine verivate that uses in the present invention can be used formula (1) or general formula (16) expression.
General formula (1)
(wherein, R
1Be that Wasserstoffatoms or carbonatoms are 2～18 alkyl.R
2, R
3And R
4Be that Wasserstoffatoms or carbonatoms are 2～18 acyl group, can be identical all, also can there be different groups.In addition, 1 D structure can be any among α or the β.But, R
1, R
2, R
3, R
4Can not all be Wasserstoffatoms).
General formula (16)
(wherein, R
9Be that carbonatoms is 2～16 acyl group.In addition, 1 D structure can be any among α or the β).
Here, R
1Be that Wasserstoffatoms or carbonatoms are 2～18 straight or branched alkyl, preferred carbonatoms is 4～16, most preferably 8～12, and be saturated group.R
2, R
3And R
4Be that Wasserstoffatoms or carbonatoms are 2～18 straight or branched acyl group, can be identical all, also can there be different groups, but preferably all be Wasserstoffatoms or ethanoyl.In addition, 1 of pyranose ring D structure can be any among α or the β.But, R
1, R
2, R
3, R
4Can not all be Wasserstoffatoms.
As the N-acetyl-glucosamine verivate of representing with general formula 1, preferably use the compound of formula (2) or (3) expression.
General formula (2)
(wherein, R
5Be that carbonatoms is 2～18 alkyl.R
6Be Wasserstoffatoms or ethanoyl.In addition, 1 D structure can be any among α or the β).
General formula (3)
(wherein, R
7Be that Wasserstoffatoms or carbonatoms are 2～18 alkyl.R
8Be that carbonatoms is 2～18 acyl group.In addition, 1 D structure can be any among α or the β).
Here, R
5Be that carbonatoms is 2～18 straight or branched alkyl, preferred carbonatoms is 4～16, most preferably 8～12, can be saturated, and also can be unsaturated.R
6Being Wasserstoffatoms or ethanoyl, preferably all is Wasserstoffatoms or ethanoyl.R
7Be that Wasserstoffatoms or carbonatoms are 2～18 straight or branched alkyl, preferred carbonatoms is 4～16, most preferably 8～12, can be saturated, and also can be unsaturated.R
8Be that carbonatoms is 2～18 straight or branched acyl group, preferred carbonatoms is 6～16, most preferably 8～12, can be saturated, and also can be unsaturated.R
9Be that carbonatoms is 2～16 straight or branched acyl group, preferred carbonatoms is 2～8, most preferably 2～4.
In addition, in general formula (1)～(17), 1 D structure of the pyranose ring of representing with wavy line can be any among α or the β.Perhaps also can have no problem ground to use its mixture.
As N-acetyl-glucosamine verivate, can specifically enumerate compound with formula (4)～(15) expression with general formula (2) or (3) expression.
General formula (4)
(1 D structure can be any among α or the β).
General formula (5)
(1 D structure can be any among α or the β).
General formula (6)
(1 D structure can be any among α or the β).
General formula (7)
(1 D structure can be any among α or the β).
General formula (8)
(1 D structure can be any among α or the β).
General formula (9)
(1 D structure can be any among α or the β).
General formula (10)
(1 D structure can be any among α or the β).
General formula (11)
(1 D structure can be any among α or the β).
These compounds can use known glucosylation reaction to synthesize.For example, if roughly represent compound method, then with regard to R in the general formula (2)
6Be the compound of Wasserstoffatoms, can under the effect of acid catalyst, through N-acetyl-glucosamine and the reaction of alcoholic acid glucosylation, make α, β blended glucoside, if use silicagel column, α, β also can emanate.And then Ru fruit Shi is Yonged the oxazoline compound method, then can make single compound β-glucoside.In addition; With regard to regard to the compound of general formula (3) expression, react to the halogenide that wherein adds various lipid acid or acid anhydrides and suitable catalyzer behind the compound that can represent through heating for dissolving N-acetyl-glucosamine in solvent or with general formula (2) and make.
General formula (12)
(1 D structure can be any among α or the β).
General formula (13)
(1 D structure can be any among α or the β).
General formula (14)
(1 D structure can be any among α or the β).
General formula (15)
(1 D structure can be any among α or the β).
These compounds can pass through commercially available 2-acetamido-1; 3; 4, the materialization of deriving of 6-four-O-ethanoyl-2-deoxidation-β-D-glycopyranoside [compound of general formula (17)], or adopt to utilize the oxazoline synthesis method of having known the glucosylation reaction pair its derive materialization and make.
As N-acetyl-glucosamine verivate, can specifically enumerate compound with formula (17) expression with general formula (16) expression.
General formula (17)
(1 D structure can be any among α or the β).
When being benchmark with the total composition, the N-acetyl-glucosamine verivate is preferably 0.00001～5.0 quality % of total composition amount to the short use level that generates agent, external composition for skin of mucinase, more preferably 0.001～3.0 quality %, most preferably 0.01～1.0 quality %.If in this scope, can give full play to the object of the invention effect.
The short generation of mucinase of the present invention agent, external composition for skin can make various doses of shapes such as ointment, lotion, emulsion, milk liquid, paste, parcel (pack) agent, sprays (mist), foam (foam) agent, particle, powder, gelifying agent.Also have, in the present invention, external composition for skin is meant that all skins with the health that comprises scalp are the preparation that is suitable for external application of object, also comprise bathing agents.With regard to matrix if normally used external-use substrate, just not special restriction.In addition, final form can make makeup, medicine, non-pharmaceuticals.
In addition; Generate in agent, the external composition for skin except cooperating above-mentioned substance in that mucinase of the present invention is short, can also be in the scope that can reach the object of the invention the following compound of proper fit, i.e. silicone oil such as tar class pigment, dimethyl polysiloxane, methyl phenyl silicone, ring-type silicone; Xenthophylls, astaxanthin (astaxanthin), fucoxanthine carotenoids pigments such as (fucoxanthin); Painted pigment such as red stone, sanitass such as p-Hydroxybenzoate, phenoxyethyl alcohol, hydro carbons such as paraffin, Vaseline; Olive three decanes, rice three decanes, rice germ oil, Jojoba oil, Viscotrol C, Thistle oil, sweet oil, macadamia oil (macadamia nut oil), sunflower seeds wet goods vegetables oil; Wax classes such as beeswax, haze tallow, POLISHING WAX-103, ester oils such as tetradecanoic acid octyl group dodecyl ester, hexadecyl palmitate, the different stearyl ester of Unimac 5680, Isopropyl myristate, lower alcohols such as ethanol; Higher alcohols such as Tego Alkanol 16 、 behenyl alcohol, VLTN 6, chain fatty alcohol; Steroid and verivates such as SUV, plant sterol, branched chain fatty acid cholesteryl ester, macadamia fatty acid phytosterin ester, quenching wet goods treated oil class, Triple Pressed Stearic Acid, tetradecanoic acid, Unimac 5680, oleic acid, different (iso) type longer chain fatty acid, anti--higher fatty acid such as different (anteiso) type longer chain fatty acid; Tri-glycerides such as terpenes such as PC 560, hydrogenation bisabolol, trioctylphosphine caprylin, 2 ethyl hexanoic acid glyceryl ester, three special-shaped long-chain fat acid glycerides, tripalmitin; Hexadecyl sodium sulfate, N-stearyl--ASs such as L-glutaminate, polyethylene oxide alkyl ethers, polyoxyethylene fatty acid esters, polyoxyethylene polyhydric alcohol fatty acid ester, polyoxyethylene solidify modified silicones such as Viscotrol C, polyhydric alcohol fatty acid ester, polyoxyethylene modified silicone, non-ionics such as polyglycerol fatty acid ester, sucrose ester; Cationic surfactants such as tetraalkylammonium salt; Amphotericses such as betaine type, DMPT type, sulfo group amino acid, natural type of tensio-active agent such as Yelkin TTS, SUNLECITHIN A, ceramide, cerebroside, pigment such as titanium oxide, zinc oxide; Inhibitors such as butylated hydroxytoluene; Inorganic salts such as sodium-chlor, magnesium chloride, sodium sulfate, saltpetre, sodium sulfate, water glass, calcium chloride, organic acid and salt thereof such as Trisodium Citrate, Potassium ethanoate, sodium succinate, Sodium L-aspartate, Sodium.alpha.-hydroxypropionate, dichloro acetic acid, RS-Mevalonic acid, glycyrrhetinic acid, organic amine and salt thereof such as diethanolamine hydrochloride, an ammonium nitrate, arginine hydrochloride, di-isopropyl amine salt, urea, decarboxylation carnosine; Sequestrants such as YD 30; Thickening materials such as xanthane gum, Carbopol ETD2050, X 5189, pectin, alkyl-modified carboxyl group vinyl polymer, agar, neutralizing agents such as Pottasium Hydroxide, HSDB 338, trolamine, UV light absorbers such as hydroxyl methoxy benzophenone sulphonate; Dipropylene glycol, marvitol, 1; Multivalence such as 3-butyleneglycol, glycerine, Ucar 35, Sorbitol Powder, Glycerol dimer, raffinose alcohol, each seed amino acid, vitamin derivatives such as vitamins such as xitix, vitamin H, Viteolin and xitix sulfuric acid, xitix phosphonic acid ester salt, nicotinic acid Viteolin etc.
And then; Urge to generate agent through corium mucinases such as the suitable N-of cooperation methyl-L-Serine, yeast extract in the scope that can achieve the goal; Along mucinase decomposing inhibitors such as silk agaric extract, black pine mushroom extract, mokkin extract, terra japonica extract, Flos Caryophylli extracts; Diisopropylamine dichloro acetic acid, nicotinic acid, RS-Mevalonic acid, thermal water, water glass, the uniform fruit of Particle Distribution angling promotor such as (homogenized fruit); Barrier enhancer such as beta-hydroxy-gamma-propalanine, RS-Mevalonic acid etc. can obtain to keep the tension force of skin or moist effect, higher wrinkle to improve effect.
Embodiment
Below, specify the present invention through embodiment.But the present invention is not limited to following embodiment.
(1) routine about the manufacturing of N-acetyl-glucosamine verivate
Make example 1
The manufacturing of octyl group (2-acetamido-2-deoxidation) β-D-glycopyranoside [compound of general formula (4)]:
Dissolving 2-acetamido-1,3,4 in anhydrous chloroform 20mL, 6-four-O-ethanoyl-2-deoxidation-β-D-glycopyranoside 2g adds trifluoromethayl sulfonic acid TMS ester 1.0mL then, stirs 5 hours under the room temperature.In reaction mixture, add chloroform, after cleaning with saturated sodium bicarbonate aqueous solution, use the anhydrous magnesium sulfate drying chloroform layer, then decompression is distilled down to remove and is desolvated.Residue is dissolved among the ethylene dichloride 15mL, adds 1-octanol 0.89mL and (±)-camphor-10-sulfonic acid 119mg, stirred 2 hours down at 60 ℃.In reaction mixture, add chloroform, after cleaning with saturated sodium bicarbonate aqueous solution, use the anhydrous magnesium sulfate drying chloroform layer, decompression is distilled down to remove and is desolvated.Use silica gel column chromatography (eluting solvent; Normal hexane: vinyl acetic monomer=2: 3) residue that obtains is at last emanated and process refining thing.It is dissolved in methane 10mL and 1, in the mixed solvent of 4-diox 5mL, adds 28% methanol solution of sodium methylate of catalytic amount, stirred 1 hour under the room temperature.After the neutralization reaction mixed solution, distillation removes and desolvates.Water carries out crystallization to the residue that obtains at last, obtains the white crystal 840mg of octyl group (2-acetamido-2-deoxidation) β-D-glycopyranoside thus.
The 1H-NMR that has represented octyl group (2-acetamido-2-deoxidation) β-D-glycopyranoside below measures the result.
NMR(DMSO-d
6)δ：0.85(t，3H，J＝6.6Hz)，1.23(s，10H)，1.40-1.45(m，2H)，1.77(s，3H)，3.00-3.10(m，2H)，3.20-3.50(m，4H)，3.65-3.75(m，2H)，4.25(d，1H，J＝8.3Hz)，4.40(t，1H)，4.78(d，1H)，4.87(d，1H)，7.58(d，1H，J＝8.7Hz).
Make example 2
The manufacturing of 2-acetamido-2-deoxidation-6-O-capryloyl-α-D-Glucopyranose [compound of general formula (5)]:
In N-acetyl-glucosamine 0.5g, add pyridine 5mL, N, N-DIMETHYL FORMAMIDE 5mL is heated to 70 ℃ when stirring, and the positive capryl(yl)chloride 0.46mL that drips makes its reaction 4 hours.After reaction finishes, use ethyl acetate extraction, clean with 2mol/L hydrochloric acid, use anhydrous magnesium sulfate drying vinyl acetic monomer layer then, the distillation down of then reducing pressure removes desolvates.Use silica gel column chromatography (eluting solvent; Chloroform: methyl alcohol=15: 1) residue that obtains is made with extra care, obtained the white crystal 170mg of 2-acetamido-2-deoxidation-6-O-capryloyl-α-D-Glucopyranose.
Represented 2-acetamido-2-deoxidation-6-O-capryloyl-α-D-Glucopyranose below
1H-NMR measures the result.
NMR(DMSO-d
6)δ：0.92(t，3H，J＝6.8Hz)，1.33(s，10H)，1.55-1.60(m，2H)，1.89(s，3H)，2.34(t，2H)，3.15-3.20(m，1H)，3.55-3.60(m，1H)，3.65-3.70(m，1H)，3.85-3.90(m，1H)，4.08(dd，1H，J＝6.0，11.6Hz)，4.35(dd，1H，J＝2.1，11.8Hz)，4.70(d，1H，J＝5.4Hz)，4.96(t，1H，J＝3.5，4.3Hz)，5.13(d，1H，J＝5.8Hz)，6.54(d，1H，J＝4.7H)，7.61(d，1H，J＝8.1Hz).
Make example 3
The manufacturing of octyl group (2-acetamido-2-deoxidation-6-O-capryloyl) β-D-glycopyranoside [compound of general formula (6)]:
With making compound [general formula (4)] the 100mg solvent shown in the example 1 in pyridine 1mL, the positive capryl(yl)chloride 61 μ L that drip make its reaction 4 hours.After reaction finishes, use chloroform extraction, clean with 2mol/L hydrochloric acid, use anhydrous magnesium sulfate drying vinyl acetic monomer layer then, the distillation down of then reducing pressure removes desolvates.Use silica gel column chromatography (eluting solvent; Chloroform: methyl alcohol=20: 1) residue that obtains is made with extra care, obtained the white crystal 170mg of octyl group (2-acetamido-2-deoxidation-6-O-capryloyl) β-D-glycopyranoside.
Represented octyl group (2-acetamido-2-deoxidation-6-O-capryloyl) β-D-glycopyranoside below
1H-NMR measures the result.
NMR(DMSO-d
6)δ：0.85(t，3H，J＝6.8Hz)，1.23(s，18H)，1.40-1.45(m，2H)，1.50-1.55(m，2H)，1.78(s，3H)，2.28(t，2H)，3.05-3.10(m，1H)，3.25-3.40(m，4H)，3.60-3.65(m，1H)，4.05(dd，1H，J＝7.2，11.6Hz)，4.28(d，1H，J＝8.0Hz)，4.30(dd，1H，J＝1.6，11.6Hz)，4.90(d，1H，J＝4.8Hz)，5.12(d，1H，J＝5.2Hz)，7.61(d，1H，J＝8.4Hz).
Make example 4
The manufacturing of butyl (2-acetamido-2-deoxidation) β-D-glycopyranoside [compound of general formula (7)]:
Use the 1-butanols to replace making the 1-octanol in the example 1, carry out and make routine 1 identical reaction, obtain white crystal butyl (2-acetamido-2-deoxidation) β-D-glycopyranoside 280mg.
The 1H-NMR that has represented butyl (2-acetamido-2-deoxidation) β-D-glycopyranoside below measures the result.
NMR(DMSO-d
6)δ：0.83(t，3H，J＝7.1Hz)，1.20-1.30(m，2H)，1.40-1.50(m，2H)，1.78(s，3H)，3.00-3.05(m，2H)，3.25-3.45(m，4H)，3.65-3.70(m，2H)，4.26(d，1H，J＝8.0Hz)，4.39(t，1H，J＝5.8Hz)，4.77(d，1H，J＝5.0Hz)，4.86(d，1H，J＝4.4Hz)，7.57(d，1H，J＝8.7Hz).
Make example 5
The manufacturing of amyl group (2-acetamido-2-deoxidation) β-D-glycopyranoside [compound of general formula (8)]:
Use the 1-amylalcohol to replace making the 1-octanol in the example 1, carry out and make routine 1 identical reaction, obtain white crystal amyl group (2-acetamido-2-deoxidation) β-D-glycopyranoside 150mg.
The 1H-NMR that has represented amyl group (2-acetamido-2-deoxidation) β-D-glycopyranoside below measures the result.
NMR(DMSO-d
6)δ：0.85(t，3H，J＝6.0Hz)，1.20-1.25(m，4H)，1.40-1.45(m，2H)，1.78(s，3H)，3.05-3.10(m，2H)，3.20-3.45(m，4H)，3.65-3.75(m，2H)，4.26(d，1H，J＝8.0Hz)，4.40(t，1H，J＝6.0Hz)，4.78(d，1H，J＝4.8Hz)，4.87(d，1H)，7.58(d，1H，J＝8.8Hz).
Make example 6
The manufacturing of lauryl (2-acetamido-2-deoxidation) β-D-glycopyranoside [compound of general formula (9)]:
Use the 1-dodecanol to replace making the 1-octanol in the example 1, carry out and make routine 1 identical reaction, obtain white crystal lauryl (2-acetamido-2-deoxidation) β-D-glycopyranoside 450mg.
Represented lauryl (2-acetamido-2-deoxidation) β-D-glycopyranoside below
1H-NMR measures the result.
NMR(DMSO-d
6)δ：0.85(t，3H，J＝6.0Hz)，?1.23(s，18H)，1.40-1.45(m，2H)，1.84(s，3H)，3.00-3.10(m，2H)，3.20-3.50(m，4H)，3.65-3.75(m，2H)，4.25(d，1H，J＝8.0Hz)，4.40(t，1H，J＝5.6Hz)，4.79(d，1H，J＝5.2Hz)，4.85(d，1H，J＝4.4Hz))，7.08(d，1H，J＝8.8Hz).
Make example 7
The manufacturing of 2-acetamido-2-deoxidation-6-O-palmitoyl-α-D-Glucopyranose [compound of general formula (10)]:
In N-acetyl-glucosamine 1g, add pyridine 5mL, N, N-DIMETHYL FORMAMIDE 15mL is heated to 70 ℃ when stirring, and the palmityl chloride 1.37mL that drips makes its reaction 4 hours.After reaction finishes, use ethyl acetate extraction, clean with 2mol/L hydrochloric acid, use anhydrous magnesium sulfate drying vinyl acetic monomer layer then, the distillation down of then reducing pressure removes desolvates.Use silica gel column chromatography (eluting solvent; Chloroform: methyl alcohol=15: 1) residue that obtains is made with extra care, obtained the white crystal 710mg of 2-acetamido-2-deoxidation-6-O-palmitoyl-α-D-Glucopyranose.
Represented 2-acetamido-2-deoxidation-6-O-palmitoyl-α-D-Glucopyranose below
1H-NMR measures the result.
NMR(DMSO-d
6)δ：0.85(t，3H，J＝6.5Hz)，1.25(s，24H)，1.45-1.55(m，2H)，1.82(s，3H)，2.30(t，2H)，3.05-3.15(m，1H)，3.45-3.65(m，2H)，3.75-3.85(m，1H)，4.00(dd，1H，J＝5.7，11.8?Hz)，4.28(dd，1H，J＝2.0，11.8Hz)，4.65(d，1H，J＝5.7Hz)，4.90(t，1H，J＝3.7，4.1Hz)，5.07(d，1H，J＝?5.7Hz)，6.45(d，1H，J＝4.5H)，7.55(d，1H，J＝8.1Hz).
Make example 8
The manufacturing of geranyl (2-acetamido-2-deoxidation) β-D-glycopyranoside [compound of general formula (11)]:
Use the Mang geraniol to replace making the 1-octanol in the example 1, carry out and make routine 1 identical reaction, obtain white crystal geranyl (2-acetamido-2-deoxidation) β-D-glycopyranoside 890mg.
Represented geranyl (2-acetamido-2-deoxidation) β-D-glycopyranoside below
1H-NMR measures the result.
NMR(DMSO-d
6)δ：1.57，1.60，1.65(3s，9H)，1.79(s，3H)，1.95-2.05(m，4H)，3.05-3.10(m，2H)，3.30-3.40(m，2H)，3.47(dt，1H，J＝5.2，12.0Hz)，3.68(dd，1H，J＝5.6，11.6Hz)，4.02(dd，1H，J＝7.2，12.0Hz)，4.17(dd，1H，J＝5.2Hz)，4.87(d，1H)，5.05-5.10(m，1H)，5.21(t，1H，J＝6.4Hz)，7.59(d，1H，J＝8.8Hz).
Make example 9
The manufacturing of ethyl (2-acetamido-3,4,6-three-O-ethanoyl-2-deoxidation) β-D-glycopyranoside [compound of general formula (12)]:
Dissolving 2-acetamido-1,3,4 in anhydrous chloroform 10mL, 6-four-O-ethanoyl-2-deoxidation-β-D-glycopyranoside [compound of general formula (17)] 1g adds trifluoromethayl sulfonic acid trimethyl silane ester 0.5mL then, stirs 5 hours under the room temperature.In reaction mixture, add chloroform, after cleaning with saturated sodium bicarbonate aqueous solution, use the anhydrous magnesium sulfate drying chloroform layer, then decompression is distilled down to remove and is desolvated.Residue is dissolved among the ethylene dichloride 8mL, adds ethanol 0.17mL and (±)-camphor-10-sulfonic acid 60mg, stirred 2 hours down at 60 ℃.In reaction mixture, add chloroform, after cleaning with saturated sodium bicarbonate aqueous solution, use the anhydrous magnesium sulfate drying chloroform layer, decompression is distilled down to remove and is desolvated.Use ether and normal hexane that the residue that obtains is at last carried out crystallization, obtain the white solid 0.5g of ethyl (2-acetamido-3,4,6-three-O-ethanoyl-2-deoxidation) β-D-glycopyranoside thus.
Represented ethyl (2-acetamido-3,4,6-three-O-ethanoyl-2-deoxidation) β-D-glycopyranoside below
1H-NMR measures the result.
NMR(CDCl
3)δ：1.18(t，3H，J＝7.3Hz)，1.93，2.00，2.05(4s，12H)，3.56(m，1H)，3.68(m，1H)，3.78(dt，1H，J＝8.4，8.8，10.4Hz)，3.88(m，1H)，4.12(dd，1H，J＝2.4，14Hz)，4.25(dd，1H，J＝4.8，12.4Hz)，4.69(d，1H，J＝8.4Hz)，5.03(t，1H，J＝9.6Hz)，5.30(t，1H，J＝9.2Hz)，5.43(d，1H，J＝8.8Hz).
Make example 10
The manufacturing of amyl group (2-acetamido-3,4,6-three-O-ethanoyl-2-deoxidation) β-D-glycopyranoside [compound of general formula (13)]:
Dissolving 2-acetamido-1,3,4 in anhydrous chloroform 15mL, 6-four-O-ethanoyl-2-deoxidation-β-D-glycopyranoside 1.5g adds trifluoromethayl sulfonic acid trimethyl silane ester 0.75mL then, stirs 5 hours under the room temperature.In reaction mixture, add chloroform, after cleaning with saturated sodium bicarbonate aqueous solution, use the anhydrous magnesium sulfate drying chloroform layer, then decompression is distilled down to remove and is desolvated.Residue is dissolved among the ethylene dichloride 15mL, adds Pentyl alcohol 0.51mL and (±)-camphor-10-sulfonic acid 99mg, stirred 2 hours down at 60 ℃.In reaction mixture, add chloroform, after cleaning with saturated sodium bicarbonate aqueous solution, use the anhydrous magnesium sulfate drying chloroform layer, decompression is distilled down to remove and is desolvated.Use silica gel column chromatography (eluting solvent; Normal hexane: vinyl acetic monomer=2: 3) residue that obtains is at last emanated refining, obtain the white solid 1.1g of amyl group (2-acetamido-3,4,6-three-O-ethanoyl-2-deoxidation) β-D-glycopyranoside thus.
Represented amyl group (2-acetamido-3,4,6-three-O-ethanoyl-2-deoxidation) β-D-glycopyranoside below
1H-NMR measures the result.
NMR(CDCl
3)δ：0.87(t，3H，J＝6.2Hz)，1.28(s，4H)，1.50-1.55(m，2H)，2.00，2.03，2.14(4s，12H)，3.45(dt，1H，J＝7.2，9.2Hz)，3.65-3.70(m，1H)，3.75-3.85(m，2H)，4.13(dd，1H，J＝2.4，12.4Hz)，4.25(dd，1H，J＝4.8，12.4Hz)，4.66(d，1H，J＝8.0Hz)，5.03(t，1H，J＝9.6Hz)，5.29(t，1H，J＝9.2Hz)，5.40(d，1H，J＝8.8Hz).
Make example 11
The manufacturing of octyl group (2-acetamido-3,4,6-three-O-ethanoyl-2-deoxidation) β-D-glycopyranoside [compound of general formula (14)]:
Dissolving 2-acetamido-1,3,4 in anhydrous chloroform 20mL, 6-four-O-ethanoyl-2-deoxidation-β-D-glycopyranoside 2g adds trifluoromethayl sulfonic acid trimethyl silane ester 1.0mL then, stirs 5 hours under the room temperature.In reaction mixture, add chloroform, after cleaning with saturated sodium bicarbonate aqueous solution, use the anhydrous magnesium sulfate drying chloroform layer, then decompression is distilled down to remove and is desolvated.Residue is dissolved among the ethylene dichloride 15mL, adds 1-octanol 0.89mL and (±)-camphor-10-sulfonic acid 119mg, stirred 2 hours down at 60 ℃.In reaction mixture, add chloroform, after cleaning with saturated sodium bicarbonate aqueous solution, use the anhydrous magnesium sulfate drying chloroform layer, decompression is distilled down to remove and is desolvated.Use silica gel column chromatography (eluting solvent; Normal hexane: vinyl acetic monomer=2: 3) residue that obtains is at last emanated refining, obtain the white solid 1.5g of octyl group (2-acetamido-3,4,6-three-O-ethanoyl-2-deoxidation) β-D-glycopyranoside thus.
Represented octyl group (2-acetamido-3,4,6-three-O-ethanoyl-2-deoxidation) β-D-glycopyranoside below
1H-NMR measures the result.
NMR(CDCl
3)δ：0.86(t，3H，J＝6.2Hz)，1.25(s，10H)，1.50-1.55(m，2H)，1.92，1.99，2.00，2.05(4s，12H)，3.40-3.45(m，1H)，3.65-3.70(m，1H)，3.75-3.90(m，2H)，4.10(d，1H，J＝12.2Hz)，4.23(d，1H，J＝4.8，12.2Hz)，4.65(d，1H，J＝8.3Hz)，5.03(t，1H，J＝9.8Hz)，5.28(t，1H，J＝9.8Hz)，5.41(d，1H，J＝8.7Hz).
Make example 12
The manufacturing of geranyl (2-acetamido-3,4,6-three-O-ethanoyl-2-deoxidation) β-D-glycopyranoside [compound of general formula (15)]:
Dissolving 2-acetamido-1,3,4 in anhydrous chloroform 50mL, 6-four-O-ethanoyl-2-deoxidation-β-D-glycopyranoside 5g adds trifluoromethayl sulfonic acid trimethyl silane ester 2.6mL then, stirs 5 hours under the room temperature.In reaction mixture, add chloroform, after cleaning with saturated sodium bicarbonate aqueous solution, use the anhydrous magnesium sulfate drying chloroform layer, then decompression is distilled down to remove and is desolvated.Residue is dissolved among the ethylene dichloride 20mL, adds Mang geraniol 2.5mL and (±)-camphor-10-sulfonic acid 298mg, stirred 2 hours down at 60 ℃.In reaction mixture, add chloroform, after cleaning with saturated sodium bicarbonate aqueous solution, use the anhydrous magnesium sulfate drying chloroform layer, decompression is distilled down to remove and is desolvated.Use silica gel column chromatography (eluting solvent; Normal hexane: vinyl acetic monomer=2: 3) residue that obtains is at last emanated refining, obtain the white solid 4.3g of geranyl (2-acetamido-3,4,6-three-O-ethanoyl-2-deoxidation) β-D-glycopyranoside thus.
Represented geranyl (2-acetamido-3,4,6-three-O-ethanoyl-2-deoxidation) β-D-glycopyranoside below
1H-NMR measures the result.
NMR(CDCl
3)δ：1.59，1.64，1.67(3s，9H)，1.91(s，3H)，1.99，2.00，2.05(3s，9H)，3.60-3.65(m，1H)，3.78(dt，1H，J＝2.8，12.4Hz)，4.10-4.30(m，3H)，4.68(d，1H，J＝8.8Hz)，5.00-5.10(m，2H)，5.20-5.40(m，2H).
(2) about having used the Test Example of N-acetyl-glucosamine verivate
Then, Test Example when using the N-acetyl-glucosamine verivate in above-mentioned manufacturing example, obtain to carry out the present invention estimates is described.
Test Example 1 (testing) to short generation of the mucinase of people's normal epidermis cell
Dull and stereotyped upper seeding wheel people's normal epidermis cell (Kurabo system) in 24 holes; Cultivate up to merging (confluent) with substratum with propagation; Being added on the N-acetyl-glucosamine verivate of making in the above-mentioned manufacturing example 1～3,6～8 then, to make its ultimate density be 50 μ mol/L (having only the example of manufacturing 7 is 25 μ mol/L), is added in addition to make the N-acetyl-glucosamine verivate of making in the example 4,5 to make its ultimate density be 1mmol/L.After interpolation is cultivated 48 hours, measure the mucinase that in substratum, discharges.When measuring mucinase, used commercially available mucinase to measure test kit (kit) (Chugai system).
The mucinase growing amount is defined as: with add N-acetyl-glucosamine make its ultimate density be 1mmol/L comparative example 1 as 1 o'clock in the mucinase amount that contains the epidermic cell that the substances substratum cultivates.The result is as depicted in figs. 1 and 2.
As shown in Figure 1; Compare with N-acetyl-glucosamine; Following compound is under the concentration of about 1/20 (making in the example 7 and be about 1/40); Demonstrated 2.5～3.5 times the short generation of mucinase effect, described compound is octyl group (2-acetamido-2-deoxidation) β-D-glycopyranoside [compound of general formula (4)], the 2-acetamido-2-deoxidation-6-O-palmitoyl-α-D-Glucopyranose [compound of general formula (10)] of making 2-acetamido-2-deoxidation-6-O-capryloyl-α-D-Glucopyranose [compound of general formula (5)] of routine 2, octyl group (2-acetamido-2-deoxidation-6-O-capryloyl) β-D-glycopyranoside [compound of general formula (6)] that makes example 3, lauryl (2-acetamido-2-deoxidation) β-D-glycopyranoside [compound of general formula (9)] that makes example 6 and manufacturing example 7 of making example 1, geranyl (2-acetamido-2-deoxidation) β-D-glycopyranoside [compound of general formula (11)] that makes example 8.R in general formula (3) particularly
7The short generation of compound that is hydrogen is active higher.
In addition; As shown in Figure 2; Following compound is under the concentration identical with N-acetyl-glucosamine; Demonstrated 1.5 times～3 times the short effect that generates of mucinase, described compound is butyl (2-acetamido-2-deoxidation) β-D-glycopyranoside [compound of general formula (7)] that makes example 4, amyl group (2-acetamido-2-deoxidation) β-D-glycopyranoside [compound of general formula (8)] that makes example 5.
Test Example 2 (testing) to short generation of the mucinase of people's normal epidermis cell
Dull and stereotyped upper seeding wheel people's normal epidermis cell (Kurabo system) in 24 holes; Cultivate up to fusion with substratum with propagation; Be added on 2-acetamido-1 then with above-mentioned general formula (17) expression; 3,4, it is 100 μ mol/L that 6-four-O-ethanoyl-2-deoxidation-β-D-glycopyranoside makes its ultimate density; Being added on the N-acetyl-glucosamine verivate of making in the above-mentioned manufacturing example 9 in addition, to make its ultimate density be 1mmol/L, is added on to make the N-acetyl-glucosamine verivate of making in the example 10～12 to make its ultimate density be 100 μ mol/L.After interpolation is cultivated 48 hours, measure the mucinase that in substratum, discharges.When measuring mucinase, used commercially available mucinase to measure test kit (Chugai system).The result is as shown in Figure 3.
As shown in Figure 3, ethyl (2-acetamido-3,4, the 6-three-O-ethanoyl-2-deoxidation) β-D-glycopyranoside [compound of general formula (12)] that makes example 9 has demonstrated 6.5 times the short effect that generates of mucinase under the concentration identical with N-acetyl-glucosamine.In addition; Make amyl group (2-acetamido-3,4, the 6-three-O-ethanoyl-2-deoxidation) β-D-glycopyranoside [compound of general formula (13)] of example 10, octyl group (the 2-acetamido-3 of manufacturing example 11; 4; 6-three-O-ethanoyl-2-deoxidation) geranyl (2-acetamido-3,4,6-three-O-ethanoyl-2-deoxidation) β-D-glycopyranoside [compound of general formula (15)], the 2-acetamido-1 of β-D-glycopyranoside [compound of general formula (14)], manufacturing example 12; 3; 4, [general formula (17 compounds) has demonstrated 3.8,2.8,3.7,3.0 times the short effect that generates of mucinase respectively to 6-four-O-ethanoyl-2-deoxidation-β-D-glycopyranoside under 1/10 concentration.
Test Example 3 (testing) to short generation of the mucinase of people's normal dermal fibroblast
Dull and stereotyped upper seeding wheel people's normal dermal fibroblast (American Type CultureCollection system) in 24 holes; Cultivate up to fusion with substratum with propagation; Adding the N-acetyl-glucosamine verivate shown in the above-mentioned manufacturing example 1 then, to make its ultimate density be 100 μ mol/L, adds in addition and make the N-acetyl-glucosamine verivate 25 μ mol/L shown in the example 6.After interpolation is cultivated 48 hours, measure the mucinase that in substratum, discharges.When measuring mucinase, used commercially available mucinase to measure test kit (Chugai system).
The mucinase growing amount is defined as: with respect to the comparative example 2 of the N-acetyl-glucosamine that has added 1mmol/L in the mucinase amount that contains the corium fabric parent cell that the substances substratum cultivates.The result is as shown in Figure 4.
As shown in Figure 4; Compare with N-acetyl-glucosamine; Make octyl group (2-acetamido-2-deoxidation) β-D-glycopyranoside [compound of general formula (4)] of example 1, these two kinds of compounds of lauryl (2-acetamido-2-deoxidation) β-D-glycopyranoside [compound of general formula (9)] of manufacturing example 6, under about 1/10～1/40 concentration, all demonstrated 1.5～2 times the short effect that generates of mucinase.
Test Example 4～7, comparative example 3,4 (through testee's evaluation)
40～60 years old women testee is divided into 8 groups; Every group 20, give different groups respectively, 2 times on the 1st with the astringent shown in the table 2 (Test Example 6,7 and comparative example 4) with the creme (Test Example 4,5 and comparative example 3) of the composition shown in the table 1; Be coated on the face logotype 3 months in right amount.After the logotype, estimate the tight sense of skin.
Evaluation divides significantly effective (the tight sense of skin has suitable improvement), effective (the tight sense of skin has good improvement), effective (the tight sense of skin has improvement), invalid (not changing) 4 stages carry out a little.Utilizing to answer significantly effectively, effectively adds up to the ratio (%) of number to come determine effect.
Table 1
| ? | Test Example 4 | Test Example 5 | Comparative example 3 |
| The compound of general formula (4) (making example 1) | 0.1 | - | - |
| The compound of general formula (17) | - | 0.1 | - |
| Triple Pressed |
2 | ? | ? |
| |
2 | ? | ? |
| Tego Alkanol 16 | 3 | ? | ? |
| SUV | 0.5 | ? | ? |
| |
2 | ? | ? |
| Three decanes | 10 | ? | ? |
| Whiteruss | 10 | ? | ? |
| |
1 | ? | ? |
| The PHB butyl ester | 0.1 | ? | ? |
| The PHB methyl ester | 0.1 | ? | ? |
| N-stearoyl- |
1 | ? | ? |
| The |
5 | ? | ? |
| Purified Water | Residual content | ? | ? |
| Add up to | 100 | ? | ? |
| Estimate (%) | 80 | 80 | 45 |
*Content all is quality %.
Table 2
| ? | Test Example 4 | Test Example 5 | Comparative example 3 |
| The compound of general formula (4) (making example 1) | 0.01 | - | - |
| The compound of general formula (17) | - | 0.01 | - |
| Ethanol | 10 | ? | ? |
| Polyoxyethylene solidifies Viscotrol C (60E.O.) | 1 | ? | ? |
| |
3 | ? | ? |
| 1,3 |
2 | ? | ? |
| |
3 | ? | ? |
| Potassium primary phosphate | 0.05 | ? | ? |
| Potassium hydrogenphosphate | 0.05 | ? | ? |
| EDTA Disodium | 0.05 | ? | ? |
| The PHB methyl ester | 0.1 | ? | ? |
| Purified Water | Residual content | ? | ? |
| Add up to | 100 | ? | ? |
| Estimate (%) | 55 | 55 | 30 |
*Content all is quality %.
Can know by table 1 and table 2, use the makeup of N-acetyl-glucosamine verivate of the present invention to have the effect of the tight sense that improves skin.
In addition, under the situation of the makeup that used any Test Example, that skin does not occur is rubescent, inflammation, other side reaction symptoms, can confirm the excellent in safety of makeup of the present invention.
(3) about embodiment
Embodiment 1 (protective skin cream)
Adopt the domestic method modulation to have the protective skin cream of following composition.
Material composition use level (quality %)
Beeswax 2.0
Triple Pressed Stearic Acid 5.0
VLTN 6 5.0
Reduction hydrous wool 2.0
Squalene 20.0
Sorbitan monostearate 3.0
Polyoxyethylene (20) sorbitan monostearate 3.0
Ucar 35 5.0
PHB methyl ester 0.2
The compound of general formula (4) (making example 1) 0.1
The Purified Water total amount is 100 o'clock a residual content
Embodiment 2 (protective skin cream)
Adopt the domestic method modulation to have the protective skin cream of following composition.
Material composition use level (quality %)
Beeswax 2.0
Triple Pressed Stearic Acid 5.0
VLTN 6 5.0
Reduction hydrous wool 2.0
Squalene 20.0
Sorbitan monostearate 3.0
Polyoxyethylene (20) sorbitan monostearate 3.0
Ucar 35 5.0
PHB methyl ester 0.2
The compound of general formula (5) (making example 2) 0.5
The Purified Water total amount is 100 o'clock a residual content
Embodiment 3 (skin lotion)
Adopt the domestic method modulation to have the skin lotion of following composition.
Material composition use level (quality %)
Sweet oil 10.0
Isopropyl myristate 1.0
Polyoxyethylene (6) nonylplenyl ether 0.5
Ucar 35 1.0
Glycerine 2.0
PHB methyl ester 0.1
Ethanol 7.0
The compound of general formula (6) (making example 3) 0.5
The Purified Water total amount is 100 o'clock a residual content
Embodiment 4 (skin lotion)
Adopt the domestic method modulation to have the skin lotion of following composition.
Material composition use level (quality %)
Sweet oil 10.0
Isopropyl myristate 1.0
Polyoxyethylene (6) nonylplenyl ether 0.5
Ucar 35 1.0
Glycerine 2.0
PHB methyl ester 0.1
Ethanol 7.0
The compound of general formula (8) (making example 5) 1.0
The Purified Water total amount is 100 o'clock a residual content
Embodiment 5 (bathing agents)
Adopt the domestic method modulation to have the bathing agents of following composition.
Material composition use level (quality %)
The compound of general formula (5) (making example 2) 1.0
The sodium hydrogencarbonate balance
Yellow soda ash 20.0
Sodium sulfate 15.0
Sodium-chlor 7.5
Silicic anhydride 0.5
1,3 butylene glycol 1.0
Urea 1.0
Seaweed Extract 1.0
Pigment is an amount of
Dextrin is an amount of
Spices is an amount of
Embodiment 6～8 (protective skin cream)
Adopt domestic method modulation protective skin cream according to following prescription.
Material composition use level (quality %)
Embodiment 678
The compound of general formula (4) (making example 1) 0.1--
The compound of general formula (5) (making example 2)-0.1-
The compound of general formula (6) (making example 3)--0.1
Triple Pressed Stearic Acid 1 1-
Unimac 5680--1
Glyceryl monostearate 222
Behenyl alcohol 222
Cetyl myristate 111
Sesquialter oleic acid sorbitan ester 111
N-stearyl phytosphingosine 0.1 0.1 0.1
Lecithin, hydrogenated 0.1 0.1 0.1
Plant three decanes 555
Tetradecanoic acid octyl group dodecyl ester 555
Cork tree extract 0.1 1 0.1
Fire sour jujube extract 0.1 0.3-
Water-soluble Radix Glycyrrhizae extract--0.1
1,3 butylene glycol 5 10 5
Concentrated glycerin 555
P-Hydroxybenzoate 0.2 0.2 0.2
N-acetyl-glucosamine oligopolymer 0.1 0.1 0.1
Ascorbic acid phosphoric acid esters Mg salt 0.1 0.1 0.1
Ascorbic acid phosphoric acid esters Na salt 0.1 0.1 0.1
γ-An Jidingsuan 0.1 0.1 0.1
N-stearoyl-glutamic acid sodium 0.2 0.2 0.2
Alkyl-modified carboxyl group vinyl polymer * 1 0.05 0.05 0.05
Vitamin PP 0.1 0.1 0.1
Sarkosine 0.1 0.1 0.1
Purified Water residual content residual content residual content
* 1; B.F.Goodrich system PEMULEN TR-1
Embodiment 9～11 (lotion)
Adopt domestic method modulation lotion according to following prescription.
Material composition use level (quality %)
Embodiment 9 10 11
The compound of general formula (4) (making example 1) 0.1--
The compound of general formula (5) (making example 2)-0.1-
The compound of general formula (6) (making example 3)--0.1
Cork tree extract 0.1 0.3 0.3
Rose of Sharon extract 0.2 0.5 0.5
Lactic acid bacteria culture solution 0.1 0.1 0.1
1,3 butylene glycol 555
Dipropylene glycol 555
Raffinose 111
Ethanol 111
Phenoxyethyl alcohol 0.2 0.2 0.2
Pectin 0.05 0.05 0.05
Xanthane gum 0.1 0.1 0.1
Trisodium Citrate 0.05 0.05 0.05
Nib dish extraction liquid 0.1 0.1 0.1
Tensicor 0.2 0.2 0.2 γ-amido-beta-hydroxy-butanoic acid 0.2 0.2 0.2
Hyaluronate sodium 0.001 0.001 0.01
Glycyrrhetinic acid dipotassium 0.2 0.2 0.2
Along silk agaric extract 0.05 0.05 0.05
Decarboxylation carnosine hydrochloride 0.05 0.05 0.05
Spices 0.02 0.02 0.02
Purified Water residual content residual content residual content
Embodiment 12～14 (gel)
Adopt the domestic method modulated gel according to following prescription.
Material composition use level (quality %)
Embodiment 12 13 14
The compound of general formula (4) (making example 1) 0.1--
The compound of general formula (5) (making example 2)-0.1-
The compound of general formula (6) (making example 3)--0.1
Decamethylcyclopentasiloxane 10 10 10
The different stearyl ester 1 of Unimac 5680--
Sweet oil-1-
Macadamia oil--1
Oil of Eucalyptus 0.1-0.1
Nicotinic acid d1 alpha-tocopherol-0.1-
Polyoxyethylene (60) solidifies Viscotrol C 222
Spherical silicone powder
*2115
Cork tree extract 0.1 1 0.1
Chlorophillins 0.02 0.02 0.02
Ocean Soviet Union extract-0.3 0.1
1,3 butylene glycol 5 10 5
D-sorbitol solution 333
Macrogol 4000 111
Carbopol ETD2050 0.2 0.2 0.2
P-Hydroxybenzoate 0.2 0.2 0.2
First hydroxyl valerolactone (mevalonolactone) 0.5 0.5 0.5
Edetate 0.02 0.02 0.02
Pottasium Hydroxide 0.05 0.05 0.05
Purified Water residual content residual content residual content
*2; The silicone system tospearl of GE Toshiba
*3: the biological ceramide of the civilian food chemistry system of recording
Embodiment 15～17 (oleophilicity creme)
Adopt domestic method modulation oleophilicity creme according to following prescription.
Material composition use level (quality %)
Embodiment 15 16 17
The compound of general formula (4) (making example 1) 0.1--
The compound of general formula (5) (making example 2)-0.1-
The compound of general formula (6) (making example 3)--0.1
Be total to modified silicone
*4222
Polyoxyethylene modified silicone dispersion liquid
*5-2-
Three decanes--10
Decamethylcyclopentasiloxane 15 20 10
Methyl polysiloxane 523
Chain fatty acid cholesterol ester
*6--3
The silicone elastomer dispersion liquid
*752
Cork tree extract 111
Radix Glycyrrhizae extract 0.1 0.1 0.1
Chlorophillins 0.02 0.02 0.02
Sodium-chlor 111
Dipropylene glycol 555
Concentrated glycerin 555
Raffinose 111
P-Hydroxybenzoate 0.3 0.3 0.3
N-methyl-L-Serine 0.5 0.5 0.5
Purified Water residual content residual content residual content
*4; Goldschmidt system ABIL EM90
*5:Toray Dow Coming silicone makes siliconeBY22-008
*6; Japan refines and makes YOFCO CLE-NH
*7; Toray Dow Coming silicone makes Trefil
Embodiment 18～20 (sunscreen)
Adopt domestic method modulation sunscreen according to following prescription.
Material composition use level (quality %)
Embodiment 18 19 20
The compound of general formula (4) (making example 1) 0.1--
The compound of general formula (5) (making example 2)-0.1-
The compound of general formula (6) (making example 3)--0.1
Dioctyl ether 10 10 10
Be total to modified silicone
*4222
Three 2 ethyl hexanoic acid glyceryl ester 555
Solidified oil 0.1 0.1 0.1
Methyl phenyl silicone 523
Macadamia fatty acid phytosterin ester--2
P-methoxycinnamic acid 2-ethylhexyl-7 7
Titanium oxide 554
Zinc oxide 554
Cork tree extract 111
Magnesium chloride 111
1,3 butylene glycol 555
Phenoxyethyl alcohol 0.3 0.3 0.3
Rose of Sharon extract 111
Aloe extract 0.1 0.1 0.1
Yeast extract
*8111
Purified Water residual content residual content residual content
*4; Goldschmidt system ABIL EM90
*8:PentaFarm makes Dismutin
Embodiment 21 (astringent)
Ethanol 10
Polyoxyethylene (60) solidifies Viscotrol C 1
1,3 butylene glycol 2
Polyethylene glycol 1500 1
Phosphoric acid salt is an amount of
Edetate is an amount of
The PHB methyl ester is an amount of
The compound of general formula (10) (making example 7) 0.1
Inhibitor is an amount of
The Purified Water residual content
Embodiment 22,23 (emulsion)
Embodiment 22 embodiment 23
Triple Pressed Stearic Acid 11
Stearin 22
Tego Alkanol 16 11
SUV 0.5 0.5
Vaseline 22
Three decanes 55
Whiteruss 55
Silicone oil 11
Acyl glutamate 11
Xanthane gum 0.5 0.5
Glycerine 22
Dipropylene glycol 33
The compound of general formula (5) (making example 2) 0.1-
The compound of general formula (10) (making example 7)-0.1
The PHB butyl ester is an amount of
Inhibitor is an amount of
Purified Water residual content residual content
Embodiment 24,25 (creme)
Embodiment 24 embodiment 25
Triple Pressed Stearic Acid 22
Stearin 22
Tego Alkanol 16 33
SUV 0.5 0.5
Vaseline 22
Three decanes 55
Whiteruss 10 10
Silicone oil 11
Acyl glutamate 11
Xanthane gum 0.5 0.5
Glycerine 55
Dipropylene glycol 33
The compound of general formula (5) (making example 2) 0.1-
The compound of general formula (10) (making example 7)-0.1
The PHB butyl ester is an amount of
Inhibitor is an amount of
Purified Water residual content residual content
Embodiment 26,27 (sunscreen)
Embodiment 26 embodiment 27
Ethanol 10 10
Octyl methoxycinnamate 77
POE/POP modification dimethyl polysiloxane 22
Titanium oxide microparticle 55
Zinc oxide 55
Ring-type silicone 10 10
Dimethyl polysiloxane (6cs) 10 10
The compound of general formula (5) (making example 2) 0.1-
The compound of general formula (10) (making example 7)-0.1
Inhibitor is an amount of
Purified Water residual content residual content
Embodiment 28 (protective skin cream)
Adopt the domestic method modulation to have the protective skin cream of following composition.
Material composition use level (quality %)
Beeswax 2.0
Triple Pressed Stearic Acid 5.0
VLTN 6 5.0
Reduction hydrous wool 2.0
Squalene 20.0
Sorbitan monostearate 3.0
Polyoxyethylene (20) sorbitan monostearate 3.0
Ucar 35 5.0
PHB methyl ester 0.2
The compound 0.1 of general formula (17)
The Purified Water total amount is 100 o'clock a residual content
Embodiment 29 (protective skin cream)
Adopt the domestic method modulation to have the protective skin cream of following composition.
Material composition use level (quality %)
Beeswax 2.0
Triple Pressed Stearic Acid 5.0
VLTN 6 5.0
Reduction hydrous wool 2.0
Squalene 20.0
Sorbitan monostearate 3.0
Polyoxyethylene (20) sorbitan monostearate 3.0
Ucar 35 5.0
PHB methyl ester 0.2
The compound of general formula (12) (making example 9) 0.5
The Purified Water total amount is 100 o'clock a residual content
Embodiment 30 (skin lotion)
Adopt the domestic method modulation to have the skin lotion of following composition.
Material composition use level (quality %)
Sweet oil 10.0
Isopropyl myristate 1.0
Polyoxyethylene (6) nonylplenyl ether 0.5
Ucar 35 1.0
Glycerine 2.0
PHB methyl ester 0.1
Ethanol 7.0
The compound 0.5 of general formula (17)
The Purified Water total amount is 100 o'clock a residual content
Embodiment 31 (bathing agents)
Adopt the domestic method modulation to have the bathing agents of following composition.
Material composition use level (quality %)
The compound 1.0 of general formula (17)
The sodium hydrogencarbonate balance
Yellow soda ash 20.0
Sodium sulfate 15.0
Sodium-chlor 7.5
Silicic anhydride 0.5
1,3 butylene glycol 1.0
Urea 1.0
Seaweed Extract 1.0
Pigment is an amount of
Dextrin is an amount of
Spices is an amount of
Embodiment 32,33 (protective skin cream)
Adopt domestic method modulation protective skin cream according to following prescription.
Material composition use level (quality %)
Embodiment 32 33
The compound 0.1 of general formula (17)-
The compound of general formula (14) (making example 11)-0.1
Triple Pressed Stearic Acid 1-
Unimac 5680-1
Glyceryl monostearate 22
Behenyl alcohol 22
Chinese wax 11
Cetyl myristate 11
Sesquialter oleic acid sorbitan ester 11
N-stearyl phytosphingosine 0.1 0.1
Lecithin, hydrogenated 0.1 0.1
Plant three decanes 55
Tetradecanoic acid octyl group dodecyl ester 55
Cork tree extract 0.1 1
Fire sour jujube extract 0.1 0.3
Water-soluble Radix Glycyrrhizae extract 0.1 0.1
1,3 butylene glycol 5 10
Concentrated glycerin 55
P-Hydroxybenzoate 0.2 0.2
N-acetyl-glucosamine oligopolymer 0.1 0.1
Ascorbic acid phosphoric acid esters Mg salt 0.1 0.1
Ascorbic acid phosphoric acid esters Na salt 0.1 0.1
γ-An Jidingsuan 0.1 0.1
N-stearoyl-glutamic acid sodium 0.2 0.2
Alkyl-modified carboxyl group vinyl polymer * 1 0.05 0.05
Vitamin PP 0.1 0.1
Sarkosine 0.1 0.1
Purified Water residual content residual content
*1; B.F.Goodrich system PEMULEN TR-1
Embodiment 34,35 (lotion)
Adopt domestic method modulation lotion according to following prescription.
Material composition use level (quality %)
Embodiment 34 35
The compound 0.1 of general formula (17)-
The compound of general formula (12) (making example 9)-0.1
Cork tree extract 0.1 0.3
Rose of Sharon extract 0.2 0.5
Lactic acid bacteria culture solution 0.1 0.1
1,3 butylene glycol 55
Dipropylene glycol 55
Raffinose 11
Ethanol 11
Phenoxyethyl alcohol 0.2 0.2
Pectin 0.05 0.05
Xanthane gum 0.1 0.1
Trisodium Citrate 0.05 0.05
Nib dish extraction liquid 0.1 0.1
Diisopropylamine dichloro acetic acid 0.2 0.2
γ-amido-beta-hydroxy-butanoic acid 0.2 0.2
Hyaluronate sodium 0.001 0.001
Glycyrrhetinic acid dipotassium 0.2 0.2
Along silk agaric extract 0.05 0.05
Decarboxylation carnosine hydrochloride 0.05 0.05
Spices 0.02 0.02
Purified Water residual content residual content
Embodiment 36,37 (gel)
Adopt the domestic method modulated gel according to following prescription.
Material composition use level (quality %)
Embodiment 36 37
The compound of general formula (13) (making example 10) 0.1-
The compound of general formula (15) (making example 12)-0.1
Decamethylcyclopentasiloxane 10 10
The different stearyl ester 1 of Unimac 5680-
Sweet oil-1
Macadamia oil 0.1 0.1
Oil of Eucalyptus 0.1-
Nicotinic acid d1 alpha-tocopherol-0.1
Polyoxyethylene (60) solidifies Viscotrol C 22
Spherical silicone powder
*211
Cork tree (phellodendron bark) extract 0.1 1
Chlorophillins 0.02 0.02
Ocean Soviet Union extract-0.3
1,3 butylene glycol 5 10
D-sorbitol solution 33
Macrogol 4000 11
Carbopol ETD2050 0.2 0.2
P-Hydroxybenzoate 0.2 0.2
First hydroxyl valerolactone 0.5 0.5
Edetate 0.02 0.02
Pottasium Hydroxide 0.05 0.05
Purified Water residual content residual content
*2; The silicone system Tospearl of GE Toshiba
*3: the biological ceramide of the civilian food chemistry system of recording
Embodiment 38,39 (oleophilicity creme)
Adopt domestic method modulation oleophilicity creme according to following prescription.
Material composition use level (quality %)
Embodiment 38 39
The compound 0.1 of general formula (17)-
The compound of general formula (15) (making example 12)-0.1
Be total to modified silicone * 422
Polyoxyethylene modified silicone dispersion liquid
*5-2
Three decanes 22
Decamethylcyclopentasiloxane 15 20
Methyl polysiloxane 52
Chain fatty acid cholesterol ester
*611
The silicone elastomer dispersion liquid
*752
Cork tree extract 11
Radix Glycyrrhizae extract 0.1 0.1
Chlorophillins 0.02 0.02
Sodium-chlor 11
Dipropylene glycol 55
Concentrated glycerin 55
Raffinose 11
P-Hydroxybenzoate 0.3 0.3
N-methyl-L-Serine 0.5 0.5
Purified Water residual content residual content
*4; Goldschmidt system ABIL EM90
*5:Toray Dow Corning silicone makes siliconeBY22-008
*6; Japan refines and makes YOFCO CLE-NH
*7; Toray Dow Corning silicone makes Trefil
Embodiment 40,41 (sunscreen)
Adopt domestic method modulation sunscreen according to following prescription.
Material composition use level (quality %)
Embodiment 40 41
The compound 0.1 of general formula (1 7)-
The compound of general formula (14) (making example 11)-0.1
Dioctyl ether 10 10
Be total to modified silicone
*422
Three 2 ethyl hexanoic acid glyceryl ester 55
Solidified oil 0.1 0.1
Methyl phenyl silicone 33
Macadamia fatty acid phytosterin 11
(phytosteryl) ester
P-methoxycinnamic acid 2-ethylhexyl-7
Titanium oxide 55
Zinc oxide 55
Cork tree extract 11
Magnesium chloride 11
1,3 butylene glycol 55
Phenoxyethyl alcohol 0.3 0.3
Rose of Sharon extract 11
Aloe extract 0.1 0.1
Yeast extract * 811
Purified Water residual content residual content
*4; Goldschmidt system ABIL EM90
*8:PentaFarm makes Dismutin
Embodiment 42 (astringent)
Ethanol 10
Polyoxyethylene (60) solidifies Viscotrol C 1
1,3 butylene glycol 2
Polyethylene glycol 1500 1
Phosphoric acid salt is an amount of
Edetate is an amount of
The PHB methyl ester is an amount of
The compound of general formula (1 5) (making example 12) 0.1
Inhibitor is an amount of
The Purified Water residual content
Embodiment 43,44 (emulsion)
Embodiment 43 embodiment 44
Triple Pressed Stearic Acid 11
Stearin 22
Tego Alkanol 16 11
SUV 0.5 0.5
Vaseline 22
Three decanes 55
Whiteruss 55
Silicone oil 11
Acyl glutamate 11
Xanthane gum 0.5 0.5
Glycerine 22
Dipropylene glycol 33
The compound 0.1 of general formula (17)-
The compound of general formula (15) (making example 12)-0.1
The PHB butyl ester is an amount of
Inhibitor is an amount of
Purified Water residual content residual content
Embodiment 45,46 (creme)
Embodiment 45 embodiment 46
Triple Pressed Stearic Acid 22
Stearin 22
Tego Alkanol 16 33
SUV 0.5 0.5
Vaseline 22
Three decanes 55
Whiteruss 10 10
Silicone oil 11
Acyl glutamate 11
Xanthane gum 0.5 0.5
Glycerine 55
Dipropylene glycol 33
The compound of general formula (13) (making example 10) 0.1-
The compound of general formula (15) (making example 12)-0.1
The PHB butyl ester is an amount of
Inhibitor is an amount of
Purified Water residual content residual content
Embodiment 47,48 (sunscreen)
Embodiment 47 embodiment 48
Ethanol 10 10
Octyl methoxycinnamate 77
POE/POP modification dimethyl polysiloxane 22
Titanium oxide microparticle 55
Zinc oxide 55
Ring-type silicone 10 10
Dimethyl polysiloxane (6cs) 10 10
The compound of general formula (13) (making example 10) 0.1-
The compound of general formula (15) (making example 12)-0.1
Inhibitor is an amount of
Purified Water residual content residual content
Utilizability in the industry
Can know that by above record the present invention can provide the short generation of mucinase that can easy and easily carry out synthetic, epidermis agent.In addition, can realize anti-aging (the tension force fire elasticity of skin, moist the keeping) of skin through the present invention.
Claims (7)
1. the application of the N-acetyl-glucosamine verivate shown in the formula (1) in the preparation of the short generation of mucinase agent,
General formula (1)
Wherein, R
1Be that Wasserstoffatoms or carbonatoms are 2～18 alkyl; R
2, R
3And R
4Be that Wasserstoffatoms or carbonatoms are 2～18 acyl group, can be identical all, also can there be different groups; Perhaps R
1, R
2, R
3And R
4All are ethanoyl; In addition, 1 D structure can be any among α or the β; But, R
1, R
2, R
3, R
4Can not all be Wasserstoffatoms.
2. application according to claim 1 is characterized in that, with the N-acetyl-glucosamine verivate shown in the formula (5) as effective constituent,
General formula (5)
Wherein, 1 D structure can be any among α or the β.
3. application according to claim 1 is characterized in that, with the N-acetyl-glucosamine verivate shown in the formula (12) as effective constituent,
General formula (12)
Wherein, 1 D structure can be any among α or the β.
4. application according to claim 1 is characterized in that, with the N-acetyl-glucosamine verivate shown in the formula (16) as effective constituent,
General formula (16)
Wherein, R
9It is ethanoyl; In addition, 1 D structure can be any among α or the β.
5. a mucinase is short generates agent, it is characterized in that, with the N-acetyl-glucosamine verivate shown in the formula (10) as effective constituent,
General formula (10)
Wherein, 1 D structure can be any among α or the β.
6. a mucinase is short generates agent, it is characterized in that, with the N-acetyl-glucosamine verivate shown in the formula (13) as effective constituent,
General formula (13)
Wherein, 1 D structure can be any among α or the β.
7. a mucinase is short generates agent, it is characterized in that, with the N-acetyl-glucosamine verivate shown in the formula (14) as effective constituent,
General formula (14)
Wherein, 1 D structure can be any among α or the β.
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002-295733 | 2002-10-09 | ||
| JP2002295733 | 2002-10-09 | ||
| JP2002295733 | 2002-10-09 | ||
| JP2003-009365 | 2003-01-17 | ||
| JP2003009365 | 2003-01-17 | ||
| JP2003009365 | 2003-01-17 | ||
| JP2003-079595 | 2003-03-24 | ||
| JP2003079595 | 2003-03-24 | ||
| JP2003079595 | 2003-03-24 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB038240866A Division CN100358911C (en) | 2002-10-09 | 2003-07-25 | N-acetylglucosamine derivatives and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101177438A CN101177438A (en) | 2008-05-14 |
| CN101177438B true CN101177438B (en) | 2012-05-23 |
Family
ID=35306304
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB038240866A Expired - Fee Related CN100358911C (en) | 2002-10-09 | 2003-07-25 | N-acetylglucosamine derivatives and use thereof |
| CN2007101823114A Expired - Fee Related CN101177438B (en) | 2002-10-09 | 2003-07-25 | N-acetylglucosamine derivatives and use thereof |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB038240866A Expired - Fee Related CN100358911C (en) | 2002-10-09 | 2003-07-25 | N-acetylglucosamine derivatives and use thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (2) | CN100358911C (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101831756B1 (en) * | 2010-09-16 | 2018-02-26 | (주)아모레퍼시픽 | Cosmetic composition for improving wrinkles and the patch for the skin around eyes using the same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6236306A (en) * | 1985-08-12 | 1987-02-17 | Taiyo Kagaku Kk | Skin-beautifying cosmetic |
| JP2585094B2 (en) * | 1989-03-16 | 1997-02-26 | 株式会社 コーセー | Cosmetics |
| JP3760287B2 (en) * | 1994-11-24 | 2006-03-29 | 株式会社コーセー | Cosmetics |
| DE19517889C2 (en) * | 1995-05-16 | 1998-12-03 | Hoechst Ag | Process for the targeted synthesis of β-glycosidically linked N-acetylglucosamine derivatives |
| JP2001002551A (en) * | 1999-06-18 | 2001-01-09 | Kanebo Ltd | Agent for increasing hyaluronic acid content of horny layer |
| JP4249853B2 (en) * | 1999-08-09 | 2009-04-08 | 焼津水産化学工業株式会社 | Oral skin moisturizer |
-
2003
- 2003-07-25 CN CNB038240866A patent/CN100358911C/en not_active Expired - Fee Related
- 2003-07-25 CN CN2007101823114A patent/CN101177438B/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN100358911C (en) | 2008-01-02 |
| CN101177438A (en) | 2008-05-14 |
| CN1688595A (en) | 2005-10-26 |
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