CN102871860A - Use of a lactose-derived c-glycoside compound as an agent for activating and regulating cutaneous immunity - Google Patents
Use of a lactose-derived c-glycoside compound as an agent for activating and regulating cutaneous immunity Download PDFInfo
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- CN102871860A CN102871860A CN2012103018718A CN201210301871A CN102871860A CN 102871860 A CN102871860 A CN 102871860A CN 2012103018718 A CN2012103018718 A CN 2012103018718A CN 201210301871 A CN201210301871 A CN 201210301871A CN 102871860 A CN102871860 A CN 102871860A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
Abstract
The present invention relates to novel lactose-derived compounds of general formula (I) and to their use as agents for stimulating the immune system of the skin and/or as immunoregulators, and for preparing a composition containing a cosmetically or pharmaceutically acceptable medium, intended in particular to prevent and/or limit the appearance of cutaneous immune imbalances, in particular related to environmental stresses.
Description
The application is to be on April 5th, 2007 applying date, application number is 200780012386.6 (international application no is PCT/EP2007/053364), and denomination of invention is divided an application for the application for a patent for invention of " lactose-derived C-glycoside compounds is as the application of the reagent that is used for activation and regulation of skin immunity ".
The present invention relates to new lactose-derived C-glycoside compounds and relate to their as being used for the immune reagent of chafe and/or as immunomodulator, but with for the preparation of contain cosmetic or medicine accepting medium, intention prevents and/or limits the application of the compositions of special relevant with the ambient pressure unbalanced appearance of skin immunization (appearance) especially.
The skin immunization disorder is the normal physiological phenomena that occurs along with the age.Yet, their may because infection of microorganism (virus and antibacterial), pressure, wear out in time, ultraviolet, " city " living conditions etc. accelerate.
Immune system comprises the integrated of special cells, and these cells stand a plurality of control mechanisms, and these mechanism have been guaranteed their renewal, their activation and their differentiation, and these cells are necessary for immunocompetent normal level.Immune effect be with self and non--self distinguish to eliminate pathogen and spontaneous tumor.Any cell depletion, any inappropriate immunomodulating or any disabler may promote all to show from uncomfortable that self is disorderly with respect to non--self recognition mechanism to being characterized as, and the pathology of the larger sensitivity for microbiological attack and neoplastic process is disorderly.
Skin be a kind of for organism very important organ, and be counted as one of them main active principle of immune protection system.Three kinds of epidermis cell types participate in this system: keratinocyte, melanocyte and langerhans cell.These cells of only finding in skin and play substantial role especially in antigen presentation in immune response.
Normal skin consists of to intercept and can make itself defends outside invasion and attack, and particularly chemistry and machinery are attacked; In this respect, the protection with respect to environmental factors (weather, ultraviolet, Nicotiana tabacum L., pollutant etc.) and/or xenobiotics's's (for example some drugs) some reflects now wherein.
Various factors such as atmosphere pollution, cleaning agent, anaphylactogen, UV ray etc. since they to the effect of skin and in exposure position partly with in negative effect various immune responses in position system ground far away.This immunosuppressant form is special relevant with inducing of antigenic specificity suppressor gene T cell.Avoid many chronic infection pathology owing to be responsible for protection by the immunoreation of T lymph corpuscle generation, so the weakening particular importance of delayed response.
Also there is not the deficiency based on immunocyte, but based on the unbalanced pathology of immunity; This particularly exists respectively excessive Th-2 lymph corpuscle and the excessive lymphocytic atopic diseases of Th-1 and the situation of autoimmune disease.
In Western society, in the past few decades, atopic diseases (is accompanied by and has excessive Th-2 type lymph corpuscle, for example atopic dermatitis, the intestines and stomach are irritated, allergic rhinitis and conjunctivitis, asthma) and popular the increasing gradually of autoimmune disease (be accompanied by and have excessive Th-1 type lymph corpuscle, for example alopecia of psoriasis, vitiligo, diffuse scleroderma, lupus erythematosus, some form, rheumatic arthritis, type I diabetes).
About reasonably explaining it is the relevant hypothesis of health seeming most of the conditions associated increase of Th-2, this hypothesis proposes increasing fast with the cleannes of present environment and beginning to be exposed to relevant (the Holt PG of minimizing under the microorganism at life of atopic eczema, Nestl é Nutrition Workshop series Pediatric Program, the editors such as Isolauri E, Allergic diseases and the environment, Karger AG, Basel, 53 volumes, 53-68 page or leaf, 2004).
During can redirecting the anaphylaxis of explanation by the Th-1-type immunoreation to the response of Th-2-type, the interaction between normal main body and the anaphylactogen changes.Anaphylaxis then is accompanied by the unbalanced of immune response, and this then may be caused by resident antibacterial (Martinez FD, Respir Res:2:129-132,2001).
These atopy situations are system's inflammatory reaction chronic and normally complicated originate from (h and E factor).In these pathology, type 2(Th-2) t helper cell plays decisive role (Romagnani S, Curr Opin Immunol6:838-846,1994) to the response of " harmless " antigen (anaphylactogen) of environment in triggering irritated condition.In irritated inflammatory process, the Th-2 cell has been explained the interference of uniting of the B cell of generation E immunoglobulin (by preparation interleukin IL-4 and IL-13) and mastocyte (by preparation IL-5).
In addition, it is also important that and highlight: although the anaphylaxis pathology relevant with Th-2 type cell increases at present, observe the pathology relevant with the Th-1 cell in developing country simultaneously and increase (autoimmune disease is type I diabetes, psoriasis or vitiligo for example).
Th-1 type cell plays an important role in the development of the hypersensitivity reaction (DHR) that postpones; Therefore, for example in rheumatic arthritis and the thyroiditis, the skin lesion of observing belongs to the DHR type, and the cd4 t cell in the described infringement mainly belongs to the Th-1 type in some chronic autoimmune disease.Since the communicate illness process of mycobacteria (tuberculosis, leprosy) in, in Lyme arthritis lysis with in the psoriasis process, obtained identical result.
Vitiligo is that the irrelevant posteriority skin depigmentation that has affected 1% world population of a kind of and the colour of skin is disorderly.Vitiligo is the dermatosis that a kind of wherein melanocyte (MC) is eliminated from the bottom of epidermis in infringement.Melanocytic this disappearance causes not enough dyeing.In the vitiligo infringement, the T cytoclasis that melanocyte is reacted by MC-.During adolescence, decolouring frequently begins.
For example, after infection, UV radiation or chemical/mechanical invasion and attack, black cell is destroyed.Under normal immune control condition, these infringements are by the immune system control that destroys modified cell.In leukodermic situation, these infringements are not correctly treated and they consist of the autoantibody source that will help to set up autoimmune pathology.
Therefore, will apply the product that to induce the local immunity phenomenon to regulate so that the treatment that Th-2 " anaphylaxis " or Th-1 " autoimmune " immune response are redirected towards the physiological equilibrium will obtain its part.
The applicant now proved the immune system that the C-glycoside compounds of general formula (I) can chafe and can correct Th-1 and Th-2 lymph corpuscle population between immune unbalanced, and can cause atopy or autoimmune disorder.
Be known that some sugar for example aldose, ketose, deoxysaccharide or monosaccharide derivatives immune stimulatory defence (EP0818201).
Also exist to regulate immune O-glycosides or C-polyglycoside molecule, for example C-slycolipid compounds (WO2003/105769), fucopeptide and acylamino-deoxy-galactose derivant (US5,962,660 and WO96/29339).
According to its first theme, the present invention relates to the chemical compound of new general formula (I):
Wherein:
-X represents to be selected from-CO-,-CH (NR
1R
2)-,-CHR '-and-C (=CHR ")-group;
-R represents to contain line style or branching, saturated or undersaturated alkyl, perfluoroalkyl or the hydrofluoroalkane base chain of 1-14 carbon atom, or cycloalkyl, ring perfluoroalkyl or ring hydrofluoroalkane basic ring, perhaps phenyl, described chain, described ring or described group can randomly be interrupted by one or more hetero atoms that are selected from oxygen, sulfur, nitrogen and silicon, and randomly are selected from by at least one-OR '
1-,-SR "
1,-NR ' "
1R '
2,-COOR "
2,-CONHR ' "
2The group of ,-CN, halogen, perfluoroalkyl and hydrofluoroalkane base, and/or at least one optional cycloalkyl that replaces, aryl or heterocyclic group replace;
-R ', R
1And R
2, it can be identical or different, has the definition identical with R and also can represent hydrogen or hydroxyl;
-R " have and the identical definition that provides for R, and also can represent hydroxyl;
-R '
2And R ' "
2, it can be identical or different, and the expression hydrogen atom perhaps is selected from hydroxyl and contains the line style of 1-14 carbon atom or the group of branching, saturated or undersaturated alkyl, perfluoroalkyl and/or hydrofluoroalkane base;
-R '
1, R "
1, R "
2And R ' "
1, it can be identical or different, and the expression hydrogen atom perhaps is selected from the line style that contains 1-14 carbon atom or the group of branching, saturated or undersaturated alkyl, perfluoroalkyl and/or hydrofluoroalkane base;
Following restriction is arranged:
-R1 and R2 can not be hydroxyl simultaneously;
-R ' 2 and R ' " 1 can not be hydroxyl simultaneously;
If-X is-CO-that then R can not be phenyl.
According to second theme, the chemical compound that the present invention relates to comprise the general formula (I ') of general formula (I) is used for reduction that skin that antagonism occurs between along with time or photic aging period defend naturally and/or the application of naturally defending of enhancing skin:
Wherein:
-X represents to be selected from-CO-,-CH (NR
1R
2)-,-CHR '-and-C (=CHR ')-group;
-R represents to contain line style or branching, saturated or undersaturated alkyl, perfluoroalkyl or the hydrofluoroalkane base chain of 1-18 carbon atom, or cycloalkyl, ring perfluoroalkyl or ring hydrofluoroalkane basic ring, perhaps phenyl, described chain, described ring or described group can randomly be interrupted by one or more hetero atoms that are selected from oxygen, sulfur, nitrogen and silicon, and randomly are selected from by at least one-OR '
1-,-SR "
1,-NR ' "
1R '
2,-COOR "
2,-CONHR ' "
2The group of ,-CN, halogen, perfluoroalkyl and hydrofluoroalkane base, and/or at least one optional cycloalkyl that replaces, aryl or heterocyclic group replace;
-R ', R
1And R
2, it can be identical or different, has the definition identical with R and also can represent hydrogen and hydroxyl;
-R '
2And R ' "
2, it can be identical or different, and the expression hydrogen atom perhaps is selected from hydroxyl and contains the line style of 1-20 carbon atom or the group of branching, saturated or undersaturated alkyl, perfluoroalkyl and/or hydrofluoroalkane base;
-R '
1, R "
1, R "
2And R ' "
1, it can be identical or different, and the expression hydrogen atom perhaps is selected from the line style that contains 1-20 carbon atom or the group of branching, saturated or undersaturated alkyl, perfluoroalkyl and/or hydrofluoroalkane base;
Following restriction is arranged:
-R1 and R2 can not be hydroxyl simultaneously;
-R ' 2 and R ' " 1 can not be hydroxyl simultaneously.
Will be preferably the chemical compound of general formula (I) and (I ') as defined above so that:
-R represents to contain line style or branching, saturated or undersaturated alkyl chain or the cycloalkyl ring of 1-10 carbon atom, perhaps phenyl, and described chain, described ring or described group can randomly be selected from by at least one-OR '
1-,-NR ' "
1R '
2,-COOR "
2With-CONHR ' "
2Group replace;
-R '
2And R ' "
2, it can be identical or different, and the expression hydrogen atom perhaps is selected from hydroxyl and contains the line style of 1-8 carbon atom or the group of branching, saturated or undersaturated alkyl;
-R '
1, R "
1, R "
2And R ' "
1, it can be identical or different, and the expression hydrogen atom perhaps is selected from the group of the line style that contains 1-8 carbon atom or branching, saturated or undersaturated alkyl.
More particularly, with the chemical compound of further preferred formula (I) and (I '), so that:
-X represents to be selected from-CO-,-CH (NR
1R
2)-and-group of CHR ';
-R represents to contain line style or branching, saturated or undersaturated alkyl chain or cycloalkyl ring, the perhaps phenyl of 1-10 carbon atom.
C-glycoside compounds representative that can be used according to the invention is described in the subtribe of the C-glycosides derivatives among the EP1345919; They can be according to the method preparation that is described in the described document.
In the middle of the C-glycosides derivatives of formula used according to the invention (I) and/or (I '), below be the most particularly preferred:
Chemical compound 1.1-(C-β-D-breast pyrans glycosyl (lactopyranosyl)) third-2-ketone;
Chemical compound 2.1-(C-β-D-breast pyrans glycosyl) third-2-ketone;
Chemical compound 3.1-(C-β-D-breast pyrans glycosyl) hendecane-2-ketone;
Chemical compound 4.1-(C-β-D-breast pyrans glycosyl)-2-hydroxy propane;
Chemical compound 5.1-[2-(3-hydroxyl the third amino) propyl group]-C-β-D-breast pyranose;
Chemical compound 6. phenyl-2-(C-β-D-breast pyrans glycosyl)-1-hydroxyl ethane;
Chemical compound 7.3-methyl-4-(C-β-D-breast pyrans glycosyl)-2-butylene acetoacetic ester;
Chemical compound 8.3-methyl-4-(β-D-breast pyrans glycosyl) ethyl n-butyrate..
More particularly, be suitable for making that skin is anti-riot is exposed under the daylight according to the application of the C-glucosides of general formula of the present invention (I) and (I ').
Therefore, according to application of the present invention so that can protect and/or the ill-effect of limit exposure under the UV ray.
The C-glucosides of general formula (I) and (I ') also can be used for keeping the balance between Th-1 and the Th-2 lymph corpuscle population and/or is used for correcting relevant immune unbalanced with excessive Th-1 type lymph corpuscle or Th-2 type lymph corpuscle.
Therefore, these chemical compounds according to the present invention can be advantageously used in the undesirable atopy type performance of antagonism, especially for therapeutic activity skin (being characterized as erythema, pain perception, swelling), be used for protection and/or reduce pruritus, for example skin and/or coloring hairs are unbalanced perhaps to resist auto immune conditions, and particularly hair bleaches too early or becomes ash.
According to another its theme, the C-glycoside compounds that the present invention relates to general formula (I) and (I ') is for the preparation of comprising the acceptable medium of physiology, being used for the application of the compositions of protection and/or treatment skin autoimmune disease or the disorder of skin atopy.
More particularly, the disorder of skin atopy is selected from skin allergy, atopic dermatitis and atopic eczema, and the skin autoimmune disease is selected from the baldness of contact sensitivity, psoriasis, vitiligo, diffuse scleroderma, lupus erythematosus or some form of delay.
Term " immunostimulant " intention refers to that medication causes for example chemical compound of lymph corpuscle propagation of described organic immunocyte to organism for it.
Term " immunomodulator " intention refers to keep and/or to rebulid the skin immunization balance between Th-1 type and the Th-2 type cell population, perhaps corrects the Th-1 type of excessive existence or the reagent of Th-2 type cell.
Especially, immunity is unbalanced can rely on the increase of one or more cytokine characteristics of lymph corpuscle type in the organism to prove.
In fact, except according to they the T receptor structure with their the classification, Th-1 type and Th-2 type lymph corpuscle are classified according to their cytokine scheme (protocol).
The lymphocytic cytokine characteristic of Class1 (Th-1) is IL-2, IFN-γ and TNF-β.Type 2(Th-2) lymphocytic cytokine is IL-4, IL-5, IL-9, IL-10 and IL-13.
More generally, the C-glycoside compounds of general formula (I) and (I ') can be used as the immunostimulation medicine among the human or animal.
Use for this class, can be for example at parenteral (intraperitoneal, subcutaneous, intramuscular, intravenous, through skin), per os, nasal cavity, conjuctivally, rectum or will comprise the compositions medication of the C-glycoside compounds of general formula (I) and/or (I ') through tongue.
They can also apply by the part, for example are used for especially the Nonspecific immunotherapy for bronchus of oral disease by means of the tablet of Orally disintegrating.
In the superincumbent various situation, medicine of the present invention can pass through prevention and administration, and is used for especially the repeated infection of protection ear, nose and throat (ENT) spheroid, and for the risk that prevents from infecting the chronic.
Medicine of the present invention is especially as immunostimulation treatment and at ENT or broncho-pulmonary field (nasopharyngitis, laryngitis, sinusitis, laryngalgia, otitis, bronchitis etc.), perhaps in the dermatosis field, and medication in the situation of antibacterial, fungus or viral infection.
Preferably, the C-glycoside compounds according to general formula of the present invention (I) and (I ') will be formulated in the local cosmetics or pharmaceutical composition that are applied on skin, scalp or the mucosa of intention.
Compositions used according to the invention can cosmetics and the dermatosis field in be suitable for imagining apply the local any form that applies particularly.
Compositions according to the present invention contain the acceptable medium of physiology and one or more with the chafe immunity or make Th-1 and the Th-2 lymph corpuscle between balance balanced effective dose again, for example with the 0.01-30wt% with respect to composition total weight, and the amount of preferred 0.1-5wt% according to chemical compound of the present invention.
Term " but physiology accepting medium " be understood to mean can with skin and the medium compatible with mucosa, fingernail, scalp and/or hair randomly.
Can be in particular following form according to compositions of the present invention: aqueous solution or the dispersion liquid of washing liquid (lotion) or serosity (serum) type, by fat being dispersed in mutually aqueous phase (O/W) otherwise or the emulsion of the milk type with liquid or semiliquid denseness that (W/O) obtains, perhaps suspension or the emulsion of the moisture or anhydrous gel of soft denseness or white type, perhaps microcapsule or microgranule, perhaps the blister-shape dispersion liquid of ion and/or nonionic type.These compositionss prepare according to common method.
Said composition can more or less be fluid and can have white or the outward appearance of colored frost, ointment, milk, washing liquid, serosity, paste or foam.Can randomly its form with aerosol be applied on the skin.It can also solid form, for example with the form of rod.It can be used as care product, cleaning product, cosmetic product or conduct and select as shampoo or conditioner.
Can be intended to for cosmetics or medicine according to compositions of the present invention, particularly dermatosis is used.Compositions according to the present invention preferably is intended to for cosmetic applications.
Therefore, a theme of the present invention or a kind of for skin or be used for the cosmetic treatment process of scalp, it comprises the above-mentioned composition part is applied on skin or the scalp.
Consider immunostimulation and equalization performance according to chemical compound of the present invention, the immunologic balance that the method is intended to especially to strengthen the natural defence of skin and improves skin.
According to C-glycoside compounds according to the present invention will be advantageously be selected from the following activating agent combination that is used for hair:
-antiseborrheic, for example some sulfur-containing amino acid, 13CRA or cyproterone acetate;
-be used for the reagent of the flaky state (dandruff) of antagonism scalp, for example vancide ZP, selenium sulfide, Climbazole, 9-undecylenic acid, ketoconazole, piroctone olamine (Octopirox) or ring piroctone (cyclopirox);
-be used for the stimulating hair regrowth and/or promote the activating agent that trichomadesis slows down; More particularly can infinite mode mention following these:
* nicotinate is particularly including tocopheryl nicotinate, benzyl nicotinate and nicotinic acid C
1-C
6Arrcostab, for example methyl nicotinate or hexyl nicotinate;
* pyrimidine derivatives for example is described in patent US4,2 in 139,619 and US4,596,812,4-diaminourea-6-piperidinyl pyrimidine 3-oxide or " Minoxidil "; Be described in Aminexil or 2,4-di-amino-pyrimidine 3-oxide among the WO96/09048;
* as the reagent of fat oxidation enzyme inhibitor and cyclo-oxygenase derivant, perhaps promote the reagent of inducing cyclo-oxygenase that hair regeneration is long, those that for example in European patent application EP 0648488, described by the applicant;
-antibiotic is macrolide, pyranoside and tetracycline for example, and is in particular erythromycin;
-cinnarizine, nimodipine and nifedipine;
-hormone such as estriol etc., or thyroxine and its salt;
-anti-androgenic gland reagent, for example oxendolone, spironolactone, diethylstilbestrol and Drogenil;
-cromakalim and nicrorandil.
The demonstration of the immunostimulatory activity of embodiment 1-C-glycosides derivatives of the present invention
Test in the following manner immunostimulatory activity: the peripheral blood cells of in the presence of the RPMI type culture medium that replenishes with L-glutaminate (2mM), penicillin/streptomycin (50 μ g/50IU/ml) and fetus calf serum (10%), cultivating the people.The C-glycosides derivatives is added with various concentration (10-0.05mM), as (as is) lectins (PHA is 5*G/ml), a kind of positive control of lymph corpuscle propagation.After 3 days cultivate, disclose propagation by the BrdU labelling.
The result who obtains is as follows:
The derivant of test shows the strong ability of lymph corpuscle propagation to the people.
Chemical compound 2 has the trend of the lymph corpuscle propagation that stimulates the people under the concentration of all tests, therefore this chemical compound has immunostimulatory activity.
Embodiment 2-prescription
The facial-care gel
The facial scrubs that is used for superactivity skin
Claims (4)
- The chemical compound of at least a general formula (I ') be used for making the anti-Sunlight exposure of skin and/or protection and/or restriction UV ray ill-effect, be used for the treatment of viable skin and/or protection and/or reduce pruritus, be used for the cosmetic applications of protection and/or the treatment autoimmune disorder relevant with the imbalance of skin dyeing, described autoimmune disorder is that hair bleaches too early or becomes grey:
Wherein:-X represents to be selected from-CO-,-CH (NR 1R 2)-,-CHR '-and-C (=CHR ')-group;-R represents to contain the line style of 1-10 carbon atom or branching, saturated or undersaturated hydrocarbyl chain, or the cyclic hydrocarbon basic ring, perhaps phenyl, and described chain, described ring or described group can randomly be selected from by at least one-OR ' 1-,-SR " 1,-NR ' " 1R ' 2,-COOR " 2,-CONHR ' " 2Group replace;-R ', R 1And R 2, it can be identical or different, has the definition identical with R and also can represent hydrogen and hydroxyl;-R ' 2And R ' " 2, it can be identical or different, and the expression hydrogen atom perhaps is selected from hydroxyl and contains the line style of 1-8 carbon atom or the group of branching, saturated or undersaturated alkyl;-R ' 1, R " 1, R " 2And R ' " 1, it can be identical or different, and the expression hydrogen atom perhaps is selected from the group of the line style that contains 1-8 carbon atom or branching, saturated or undersaturated alkyl;Following restriction is arranged:-R 1And R 2Can not be hydroxyl simultaneously;-R ' 2And R ' " 1Can not be hydroxyl simultaneously. - 2. according to claim 1 application is characterised in that:-X represents to be selected from-CO-,-CH (NR 1R 2)-and-group of CHR ';-R represents to contain line style or branching, saturated or undersaturated hydrocarbyl chain or cyclic hydrocarbon basic ring, the perhaps phenyl of 1-10 carbon atom.
- 3. according to claim 1 application is characterised in that chemical compound when described general formula (I) is used for that protection and/or treatment hair bleach too early or when becoming ash, and the chemical compound of described general formula (I) and at least a active agent for hair make up.
- 4. according to claim 1-3 each application is characterised in that the chemical compound of general formula (I ') is selected from:Chemical compound 1.1-(C-β-D-breast pyrans glycosyl) third-2-ketone;Chemical compound 2.1-(C-β-D-breast pyrans glycosyl) third-2-ketone;Chemical compound 3.1-(C-β-D-breast pyrans glycosyl) hendecane-2-ketone;Chemical compound 4.1-(C-β-D-breast pyrans glycosyl)-2-hydroxy propane;Chemical compound 5.1-[2-(3-hydroxyl the third amino) propyl group]-C-β-D-breast pyranose;Chemical compound 6. phenyl-2-(C-β-D-breast pyrans glycosyl)-1-hydroxyl ethane;Chemical compound 7.3-methyl-4-(C-β-D-breast pyrans glycosyl)-2-butylene acetoacetic ester;Chemical compound 8.3-methyl-4-(β-D-breast pyrans glycosyl) ethyl n-butyrate..
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0651268 | 2006-04-07 | ||
| FR0651268A FR2899587B1 (en) | 2006-04-07 | 2006-04-07 | USE OF LACTOSE-DERIVED C-GLYCOSIDE COMPOUND AS AN ACTIVATOR AND REGULATOR OF SKIN IMMUNITY |
| CN2007800123866A CN101553478B (en) | 2006-04-07 | 2007-04-05 | Use of a lactose-derived c-glycoside compound as an agent for activating and regulating cutaneous immunity |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007800123866A Division CN101553478B (en) | 2006-04-07 | 2007-04-05 | Use of a lactose-derived c-glycoside compound as an agent for activating and regulating cutaneous immunity |
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| Publication Number | Publication Date |
|---|---|
| CN102871860A true CN102871860A (en) | 2013-01-16 |
| CN102871860B CN102871860B (en) | 2015-09-16 |
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| CN2007800123866A Active CN101553478B (en) | 2006-04-07 | 2007-04-05 | Use of a lactose-derived c-glycoside compound as an agent for activating and regulating cutaneous immunity |
| CN201210301871.8A Active CN102871860B (en) | 2006-04-07 | 2007-04-05 | Lactose-derived C-glycoside compounds is as activating the application with the reagent of regulation of skin immunity |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0818201B1 (en) * | 1996-07-10 | 2002-03-13 | L'oreal | Use of a polysaccharide to stimulate immune defenses |
| WO2002051803A2 (en) * | 2000-12-22 | 2002-07-04 | L'oreal | Novel c-glycoside derivatives and use thereof |
| WO2002051828A2 (en) * | 2000-12-22 | 2002-07-04 | L'oreal | Novel c-glycoside derivatives and use thereof |
| WO2003105769A2 (en) * | 2002-06-13 | 2003-12-24 | New York University | Synthetic c-glycolipid and its use for treating cancer infectious diseases and autoimmune diseases |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2882516B1 (en) * | 2005-02-25 | 2007-05-25 | Oreal | CAPILLARY USE OF C-GLYCOSIDE DERIVATIVES |
-
2006
- 2006-04-07 FR FR0651268A patent/FR2899587B1/en not_active Expired - Fee Related
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2007
- 2007-04-05 CN CN2007800123866A patent/CN101553478B/en active Active
- 2007-04-05 ES ES07727832.3T patent/ES2637508T3/en active Active
- 2007-04-05 CN CN201210301871.8A patent/CN102871860B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0818201B1 (en) * | 1996-07-10 | 2002-03-13 | L'oreal | Use of a polysaccharide to stimulate immune defenses |
| WO2002051803A2 (en) * | 2000-12-22 | 2002-07-04 | L'oreal | Novel c-glycoside derivatives and use thereof |
| WO2002051828A2 (en) * | 2000-12-22 | 2002-07-04 | L'oreal | Novel c-glycoside derivatives and use thereof |
| WO2003105769A2 (en) * | 2002-06-13 | 2003-12-24 | New York University | Synthetic c-glycolipid and its use for treating cancer infectious diseases and autoimmune diseases |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101553478A (en) | 2009-10-07 |
| ES2637508T3 (en) | 2017-10-13 |
| CN101553478B (en) | 2012-10-10 |
| FR2899587A1 (en) | 2007-10-12 |
| FR2899587B1 (en) | 2008-11-28 |
| CN102871860B (en) | 2015-09-16 |
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