LU87408A1 - USE OF SALICYL DERIVATIVES FOR THE TREATMENT OF AGING SKIN - Google Patents
USE OF SALICYL DERIVATIVES FOR THE TREATMENT OF AGING SKIN Download PDFInfo
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- LU87408A1 LU87408A1 LU87408A LU87408A LU87408A1 LU 87408 A1 LU87408 A1 LU 87408A1 LU 87408 A LU87408 A LU 87408A LU 87408 A LU87408 A LU 87408A LU 87408 A1 LU87408 A1 LU 87408A1
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- 230000032683 aging Effects 0.000 title claims abstract description 15
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical class CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 56
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 150000003872 salicylic acid derivatives Chemical class 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000000499 gel Substances 0.000 claims description 11
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 10
- 229960004889 salicylic acid Drugs 0.000 claims description 10
- 230000009759 skin aging Effects 0.000 claims description 7
- -1 stick Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000006071 cream Substances 0.000 claims description 4
- 230000000699 topical effect Effects 0.000 claims description 4
- 239000006260 foam Substances 0.000 claims description 3
- 239000002674 ointment Substances 0.000 claims description 3
- 239000003755 preservative agent Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- 239000001993 wax Substances 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000003974 emollient agent Substances 0.000 claims description 2
- 150000002148 esters Chemical group 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- 235000020778 linoleic acid Nutrition 0.000 claims description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 2
- 229960004488 linolenic acid Drugs 0.000 claims description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 2
- 239000006210 lotion Substances 0.000 claims description 2
- 235000013336 milk Nutrition 0.000 claims description 2
- 210000004080 milk Anatomy 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 235000021313 oleic acid Nutrition 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000008267 milk Substances 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 210000003491 skin Anatomy 0.000 description 23
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 4
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000037303 wrinkles Effects 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N propylene glycol methyl ether Substances COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 230000007321 biological mechanism Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- JVTIXNMXDLQEJE-UHFFFAOYSA-N 2-decanoyloxypropyl decanoate 2-octanoyloxypropyl octanoate Chemical compound C(CCCCCCC)(=O)OCC(C)OC(CCCCCCC)=O.C(=O)(CCCCCCCCC)OCC(C)OC(=O)CCCCCCCCC JVTIXNMXDLQEJE-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- LKLYETYHDMXRAF-UHFFFAOYSA-N 2-octanoyloxybenzoic acid Chemical compound CCCCCCCC(=O)OC1=CC=CC=C1C(O)=O LKLYETYHDMXRAF-UHFFFAOYSA-N 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 206010064127 Solar lentigo Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- 230000002491 angiogenic effect Effects 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N beta-monoglyceryl stearate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000002995 comedolytic effect Effects 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 230000003061 melanogenesis Effects 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 229930002330 retinoic acid Natural products 0.000 description 1
- 229960003471 retinol Drugs 0.000 description 1
- 235000020944 retinol Nutrition 0.000 description 1
- 239000011607 retinol Substances 0.000 description 1
- 230000004215 skin function Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000009056 telangiectasis Diseases 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/60—Salicylic acid; Derivatives thereof
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- 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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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Mémoire descriptif déposé à l'appui d'une demande de brevet d'invention pour : "Utilisation de dérivés salicylés pour le traitement du vieillissement de la peau" L'OREAL 14, rue Royale F-75008- PARIS FranceDescription filed in support of a patent application for: "Use of salicylated derivatives for the treatment of skin aging" L'OREAL 14, rue Royale F-75008- PARIS France
Utilisation de dérivés salicylés pour le traitement du vieillissement de la peau.Use of salicylated derivatives for the treatment of aging skin.
La présente invention a pour objet de nouvelles compositions destinées à traiter le vieillissement de la peau en mettant en oeuvre des dérivés d'acide salicylique.The subject of the present invention is new compositions intended for treating the aging of the skin by using salicylic acid derivatives.
On constate au cours du processus de vieillissement l'apparition de différents signes au niveau de la peau, très caractéristiques de ce vieillissement, se traduisant notamment par une modification de la structure et de la fonction cutanée. Ces signes sont particulièrement marqués sur les zones découvertes, telles que le visage, les mains, auxquelles se rajoutent généralement des caractéristiques particulières dues à l'exposition de la peau à la lumière solaire (vieillissement actinique).We observe during the aging process the appearance of different signs in the skin, very characteristic of this aging, resulting in particular in a change in the structure and skin function. These signs are particularly marked on the uncovered areas, such as the face, the hands, to which are generally added particular characteristics due to the exposure of the skin to sunlight (actinic aging).
Il est difficile, en général, sur une zone découverte, de distinguer clairement entre les signes provenant du processus physiologique de vieillissement de la peau et entre les signes dus à l'exposition répétée de la peau à la lumière.It is generally difficult in an open area to clearly distinguish between signs from the physiological process of skin aging and between signs due to repeated exposure of the skin to light.
Les principaux signes cliniques de vieillissement cutané sont les suivants : apparition de rides profondes en augmentation avec l'âge. On constate en particulier une désorganisation du "grain" de la peau, c'est-à-dire que le micro-relief est moins régulier et présente un caractère anisotrope.The main clinical signs of skin aging are as follows: appearance of deep wrinkles which increase with age. There is in particular a disorganization of the "grain" of the skin, that is to say that the micro-relief is less regular and has an anisotropic character.
Le teint de la peau est généralement modifié, il apparaît plus pâle et plus jaune, ce qui semble être dû essentiellement à une désorganisation de la microcirculation (moins d'hémoglobine au niveau du derme papillaire). De nombreuses tâches colorées apparaissent en surface, ce qui est dû à une mélanogénèse altérée. Il existe sur certaines zones des irritations diffuses et parfois des telangiectasies.The skin tone is generally changed, it appears paler and more yellow, which seems to be mainly due to a disorganization of the microcirculation (less hemoglobin in the papillary dermis). Many colored spots appear on the surface, which is due to altered melanogenesis. There are diffuse irritations and sometimes telangiectasias in certain areas.
Un autre signe clinique de vieillissement est l'aspect sec et rèche de la peau qui est dû essentiellement à une desquamation plus importante, ces squames en diffractant les rayons lumineux participent aussi à l'aspect un peu gris du teint.Another clinical sign of aging is the dry, dry appearance of the skin, which is essentially due to greater flaking, these dander by diffracting the light rays also participate in the somewhat gray appearance of the complexion.
On constate enfin une perte de fermeté et de tonicité de la peau qui, comme pour les rides, s'explique du moins en partie par une atrophie dermique et épidermique ainsi qu'un applatissement de la formation dermoépidermique.Finally, there is a loss of firmness and tone of the skin which, as with wrinkles, is explained at least in part by dermal and epidermal atrophy and a flattening of the dermoepidermal formation.
On constate donc que les signes cliniques de vieillissement cutané résultent essentiellement d'un dysfonctionnement des principaux mécanismes biologiques intervenant au niveau de la peau.It is therefore observed that the clinical signs of skin aging result essentially from a dysfunction of the main biological mechanisms involved in the skin.
La demanderesse a découvert de façon surprenante que l'utilisation de dérivés d'acide salicylique permettait de retarder ce vieillissement et d'agir sur les signes cliniques de celui-ci.The Applicant has surprisingly discovered that the use of salicylic acid derivatives makes it possible to delay this aging and to act on the clinical signs thereof.
Elle a constaté plus particulièrement que grâce à ces dérivés salicyliques, il était possible d'atténuer pour le moins les rides, de modifier le teint de la peau qui apparaît plus rosé, d'effacer les taches pigmentées en surface, de supprimer les squames et de donner une consistance plus élastique à la peau. On a constaté en particulier qu'il était possible de conférer à la peau un toucher beaucoup plus doux.She noted more particularly that thanks to these salicylic derivatives, it was possible to attenuate at least wrinkles, to modify the complexion of the skin which appears more rosy, to erase pigmented spots on the surface, to remove dander and to give a more elastic consistency to the skin. In particular, it has been found that it is possible to impart a much softer feel to the skin.
Les dérivés d'acide salicylique utilisables conformément à l'invention, sont connus en eux-mêmes et ont déjà été décrits dans l'état de la technique comme pouvant être utilisés dans des compositions topiques dans le domaine de la cosmétologie et la dermopharmacie et plus particulièrement comme agents thérapeutiques et comédolytiques, tels que pour le traitement de l'acné.The salicylic acid derivatives which can be used in accordance with the invention are known in themselves and have already been described in the prior art as being capable of being used in topical compositions in the field of cosmetology and dermopharmacy and more particularly as therapeutic and comedolytic agents, such as for the treatment of acne.
La demanderesse a découvert maintenant une application thérapeutique nouvelle agissant sur un mécanisme biologique totalement différent de celui de l'acné que l'on rencontre principalement chez les sujets jeunes. L'invention a donc principalement pour objet l'utilisation pour le traitement du vieillissement de la peau, de dérivés d'acide salicylique.The Applicant has now discovered a new therapeutic application acting on a biological mechanism totally different from that of acne, which is mainly encountered in young people. The invention therefore mainly relates to the use for the treatment of aging of the skin, of salicylic acid derivatives.
Un autre objet de l'invention est constitué par les compositions mises en oeuvre. D'autres objets de l'invention apparaîtront à la lecture de la description et des exemples qui suivent.Another object of the invention consists of the compositions used. Other objects of the invention will appear on reading the description and the examples which follow.
Les dérivés d'acide salicylique utilisables conformément à l'invention pour le traitement du vieillissement de la peau, répondent essentiellement à la formule générale suivante :The salicylic acid derivatives which can be used in accordance with the invention for the treatment of aging of the skin essentially correspond to the following general formula:
(I) dans laquelle : R représente une chaîne aliphatique saturée ayant de 3 à 11 atomes de carbone, linéaire, ramifiée ou cyclisée, une chaîne insaturée ayant de 3 à 17 atomes de carbone, portant une ou plusieurs doubles liaisons conjuguées ou non, les chaînes ci-dessus peuvent également être substituées par un ou plusieurs atomes d'halogène ainsi que par des groupements trifluorométhyle, par un ou plusieurs groupements hydroxyle sous forme libre ou estérifiée par un acide ayant de 1 à 6 atomes de carbone ou bien par une fonction carboxyle, libre ou estérifiée, par un alcool inférieur ayant de 1 à 6 atomes de carbone, ces différents groupements pouvant être simultanément présents sur lesdits substituants; R' représente un groupement hydroxyle ou une fonction ester répondant à la formule :(I) in which: R represents a saturated aliphatic chain having from 3 to 11 carbon atoms, linear, branched or cyclized, an unsaturated chain having from 3 to 17 carbon atoms, carrying one or more double bonds conjugated or not, the above chains can also be substituted by one or more halogen atoms as well as by trifluoromethyl groups, by one or more hydroxyl groups in free form or esterified by an acid having from 1 to 6 carbon atoms or by a function carboxyl, free or esterified, with a lower alcohol having from 1 to 6 carbon atoms, these various groups being able to be simultaneously present on the said substituents; R 'represents a hydroxyl group or an ester function corresponding to the formula:
(II) dans laquelle R-| est un groupement aliphatique, saturé ou insaturé, ayant de 1 à 18 atomes de carbone.(II) in which R- | is an aliphatic group, saturated or unsaturated, having from 1 to 18 carbon atoms.
Les composés plus particulièrement préférés sont ceux répondant à la formule (I) ci-dessus, dans lesquels R' désigne une fonction hydroxyle, R un groupement alkyle ayant de 3 à 11 atomes de carbone. D'autres composés particulièrement intéressants sont ceux dans lesquels R représente une chaîne dérivée de l'acide linoléique, linolénique ou oléique.The compounds which are more particularly preferred are those corresponding to formula (I) above, in which R ′ denotes a hydroxyl function, R an alkyl group having from 3 to 11 carbon atoms. Other particularly interesting compounds are those in which R represents a chain derived from linoleic, linolenic or oleic acid.
Un autre groupe de composés particulièrement préférés est constitué par les composés dans lesquels R désigne une chaîne alkyle ayant de 3 à 11 atomes de carbone et portant un groupement carboxylique libre, estérifié ou salifié et R1 désigne une fonction hydroxyle.Another group of particularly preferred compounds consists of the compounds in which R denotes an alkyl chain having from 3 to 11 carbon atoms and carrying a free, esterified or salified carboxylic group and R1 denotes a hydroxyl function.
Des composés particulièrement intéressants, conformément à l'invention, sont choisis parmi l'acide n-octanoyl-5 salicylique, l'acide n-dodécanoyl-5 salicylique, l'acide n-décanoyl-5 salicylique, ces composés pouvant éventuellement être utilisés sous forme micronisée.Particularly advantageous compounds, in accordance with the invention, are chosen from n-octanoyl-5 salicylic acid, n-dodecanoyl-5 salicylic acid, n-decanoyl-5 salicylic acid, these compounds possibly being used in micronized form.
Des essais effectués par la demanderesse ont permis en particulier de montrer que les composés conformes à l'invention ont un effet angiogénique particulièrement remarquable. Cette activité a été déterminée de la façon suivante.Tests carried out by the applicant have made it possible in particular to show that the compounds in accordance with the invention have a particularly remarkable angiogenic effect. This activity was determined as follows.
Des souris mâles ont été soumises à un traitement topique avec une composition contenant l'acide n-octanoyl-5 salicylique à 2,5% dans l'acétone, en poids par volume, par rapport à un témoin constitué par de l'acétone pure.Male mice were subjected to a topical treatment with a composition containing 2.5% n-octanoyl-salicylic acid in acetone, by weight per volume, relative to a control consisting of pure acetone .
Ces compositions sont appliquées à raison de 50 /xl sur le dos des souris, chaque jour, pendant 5 jours par semaine et ceci pendant 21 semaines.These compositions are applied at a rate of 50 μl on the back of the mice, every day, for 5 days per week and this for 21 weeks.
Au terme des 21 semaines durant lesquelles l'épaisseur cutanée a été régulièrement mesurée par un dispositif HARPENDER CALIPER, les souris sont sacrifiées, la peau du dos prélevée. Celle-ci, retournée, est alors photographiée afin de noter l'extension du réseau capillaire cutané.At the end of the 21 weeks during which the skin thickness was regularly measured by a HARPENDER CALIPER device, the mice are sacrificed, the back skin removed. This one, turned over, is then photographed in order to note the extension of the cutaneous capillary network.
On constate que l'application de la composition à base d'acide n-octanoyl-5 salicylique provoque une large augmentation du volume et du nombre des capillaires.It is found that the application of the composition based on n-octanoyl-5 salicylic acid causes a large increase in the volume and the number of capillaries.
Les compositions, utilisées conformément à l'invention, dans le traitement du vieillissement cutané, contiennent dans un milieu physiologiquement acceptable, au moins un dérivé d'acide salicylique de formule (I) définie ci-dessus et se présentent généralement sous forme de gels, de crèmes, de lotions, de sticks, de mousses, de savons ou peuvent être pressurisées dans des dispositifs aérosols.The compositions, used in accordance with the invention, in the treatment of skin aging, contain, in a physiologically acceptable medium, at least one salicylic acid derivative of formula (I) defined above and are generally in the form of gels, creams, lotions, sticks, foams, soaps or can be pressurized in aerosol devices.
Elles peuvent contenir de l'eau et/ou des solvants compatibles avec la peau, tels que les alcools inférieurs en C1-C4, comme l'éthanol, 1'isopropanol, des polyalcools tels que le propylèneglycol, la glycérine, ces solvants étant présents dans des proportions comprises entre 5 et 99% en poids.They may contain water and / or solvents compatible with the skin, such as C1-C4 lower alcohols, such as ethanol, isopropanol, polyalcohols such as propylene glycol, glycerin, these solvents being present. in proportions of between 5 and 99% by weight.
Elles peuvent également se présenter sous forme de compositions grasses, contenant des huiles ou des corps gras, tels que la vaseline et les triglycérides.They can also be in the form of fatty compositions, containing oils or fatty substances, such as petrolatum and triglycerides.
Le composé de formule (I) conforme à l'invention est présent dans ces compositions de préférence dans des proportions comprises entre 0,1 et 10% en poids.The compound of formula (I) according to the invention is present in these compositions preferably in proportions of between 0.1 and 10% by weight.
Ces compositions peuvent également contenir des épaississants, des adoucissants, des surgraissants, des émollients, des mouillants, des agents de surface, des conservateurs, des agents anti-mousses, des filtres solaires, des huiles, des cires, des colorants et/ou des pigments ayant pour fonction de colorer la peau ou la composition elle-même, des anti-oxydants et tout autre ingrédient habituellement utilisé dans des compositions destinées à une application topique.These compositions can also contain thickeners, softeners, superfatters, emollients, wetting agents, surfactants, preservatives, anti-foaming agents, sun filters, oils, waxes, dyes and / or pigments having the function of coloring the skin or the composition itself, antioxidants and any other ingredient usually used in compositions intended for topical application.
Des compositions particulièrement préférées sont des gels anhydres, des crèmes, des pommades grasses ou des laits comprenant en plus des composés définis ci-dessus, des alcools gras, des alcools gras oxyéthylénés ou polyglycérolés, des esters d'acides gras, des huiles naturelles ou synthétiques, des cires.Particularly preferred compositions are anhydrous gels, creams, fatty ointments or milks comprising, in addition to the compounds defined above, fatty alcohols, oxyethylenated or polyglycerolated fatty alcohols, fatty acid esters, natural oils or synthetic, waxes.
Dans le traitement du vieillissement cutané, ces compositions sont plus particulièrement appliquées sur les zones exposées à la lumière à. raison de 1 à 10 mg/cm^ de peau et pendant une durée pouvant aller d'une semaine à 20 semaines ou plus.In the treatment of skin aging, these compositions are more particularly applied to the areas exposed to light. at a rate of 1 to 10 mg / cm ^ of skin and for a period which can range from one week to 20 weeks or more.
Les compositions conformes à l'invention peuvent également contenir d'autres substances actives ayant un effet sur le vieillissement de la peau, telles que plus particulièrement des rétinoïdes, tels que par exemple l'acide rétinoïque tout-trans, l'acide 13-cis rétinoïque, le rétinol, le rétinal et leurs dérivés. Il est également possible d'appliquer ces dérivés en deux temps de façon successive ou décalée dans le temps.The compositions in accordance with the invention may also contain other active substances having an effect on the aging of the skin, such as more particularly retinoids, such as for example all-trans retinoic acid, 13-cis acid. retinoic, retinol, retinal and their derivatives. It is also possible to apply these derivatives in two stages successively or over time.
Les exemples suivants sont destinés à illustrer l'invention sans pour autant présenter un caractère limitatif. EXEMPLE 1The following examples are intended to illustrate the invention without, however, being limiting in nature. EXAMPLE 1
On prépare la composition suivante : - Propylèneglycol 45,00 g - Acide n-octanoyl-5 salicylique 3,00 g - KLUCEL H (hydroxypropylcellulose) vendue par la Société HERCULES 1,50 g - Ethanol anhydre qsp 100,00 gThe following composition is prepared: - Propylene glycol 45.00 g - 5-N-octanoyl salicylic acid 3.00 g - KLUCEL H (hydroxypropylcellulose) sold by the company HERCULES 1.50 g - Anhydrous ethanol qs 100.00 g
Cette composition se présente sous forme de gel. EXEMPLE 2This composition is in the form of a gel. EXAMPLE 2
On prépare la composition suivante : - Méthyléther de propylèneglycol 37,00 g - Hydroxypropylcellulose 1,50 g - Acide n-octanoyl-5 salicylique 3,00 g - Ethanol anhydre qsp 100,00 gThe following composition is prepared: - Propylene glycol methyl ether 37.00 g - Hydroxypropylcellulose 1.50 g - 5-N-octanoyl salicylic acid 3.00 g - Anhydrous ethanol qs 100.00 g
Cette composition se présente sous forme de gel. EXEMPLE 3This composition is in the form of a gel. EXAMPLE 3
On prépare la composition suivante : - Méthyléther de propylèneglycol 35,00 g - Hydroxyéthylcellulose 1,50 g - Acide n-octanoyl-5 salicylique 5,00 g - Ethanol anhydre qsp 100,00 gThe following composition is prepared: - Propylene glycol methyl ether 35.00 g - Hydroxyethylcellulose 1.50 g - 5-n-octanoyl salicylic acid 5.00 g - Anhydrous ethanol qs 100.00 g
Cette composition se présente sous forme de gel. EXEMPLE 4This composition is in the form of a gel. EXAMPLE 4
On prépare la composition suivante : - Propylèneglycol 35,00 g - Hydroxypropylcellulose 1,50 g - Acide n-octanoyl-5 salicylique 5,00 g - Ethanol anhydre qsp 100,00 gThe following composition is prepared: - Propylene glycol 35.00 g - Hydroxypropylcellulose 1.50 g - 5-N-octanoyl salicylic acid 5.00 g - Anhydrous ethanol qs 100.00 g
Cette composition se présente sous forme de gel. EXEMPLE 5This composition is in the form of a gel. EXAMPLE 5
On prépare la composition suivante : - Vaseline 65,00 g - Acide n-octanoyl-5 salicylique 5,00 g - Perhydrosqualène qsp 100,00 gThe following composition is prepared: - Vaseline 65.00 g - N-octanoyl-5 salicylic acid 5.00 g - Perhydrosqualene qs 100.00 g
Cette composition est utilisable sous forme de pommade grasse. EXEMPLE 6This composition can be used in the form of a fatty ointment. EXAMPLE 6
On prépare la composition suivante : - Propylèneglycol 5,00 g - Acide n-octanoyl-5 salicylique 4,00 g - Acide acrylique réticulé par un agent polyfonctionnel, vendu sous la dénomination CARBOPOL 940 par laThe following composition is prepared: - Propylene glycol 5.00 g - 5-n-octanoyl-salicylic acid 4.00 g - Acrylic acid crosslinked with a polyfunctional agent, sold under the name CARBOPOL 940 by
Société GOODRICH 0,80 g - NaOH 0,125 g - Eau qsp 100,00 g L'acide n-octanoyl-5 salicylique est utilisé sous forme micronisée avec une granulométrie inférieure à 5yu.GOODRICH company 0.80 g - NaOH 0.125 g - Water qs 100.00 g The n-octanoyl-5 salicylic acid is used in micronized form with a particle size less than 5yu.
Cette composition se présente sous forme de gel. EXEMPLE 7This composition is in the form of a gel. EXAMPLE 7
On prépare la composition suivante : - Monostéarate de glycerol 0,80 g - Alcool cétylique 2,00 g - Alcool cétylstéarylique 5,00 g - Stéarate de polyoxyéthylène, vendu par la Société ATLAS sous la dénomination commerciale de MYRJ 49 3,00 g - Acide acrylique réticulé par un agent polyfonctionnel, vendu sous la dénomination CARBOPOL 941 par laThe following composition is prepared: - Glycerol monostearate 0.80 g - Cetyl alcohol 2.00 g - Cetylstearyl alcohol 5.00 g - Polyoxyethylene stearate, sold by the company ATLAS under the trade name of MYRJ 49 3.00 g - Acrylic acid crosslinked with a polyfunctional agent, sold under the name CARBOPOL 941 by the
Société GOODRICH 0,50 g - Triéthanolamine 0,30 g - MIGLYOL 810 vendu par la Société DYNAMIT NOBEL 12,00 g - Conservateur qs - Acide n-octanoyl-5 salicylique 6,00 g - Eau qsp 100,00 gGOODRICH company 0.50 g - Triethanolamine 0.30 g - MIGLYOL 810 sold by the company DYNAMIT NOBEL 12.00 g - Preservative qs - N-octanoyl-5 salicylic acid 6.00 g - Water qs 100.00 g
Cette composition est utilisée comme crème hydratante. EXEMPLE 8This composition is used as a moisturizer. EXAMPLE 8
On prépare la composition suivante î - Acide n-octanoyl-5 salicylique 4,00 g - Polyéthylèneglycol 400 18,50 g - Méthyléther de propylèneglycol 18,50 g - Hydroxypropylcellulose 1,50 g - Ethanol anhydre qsp 100,00 gThe following composition is prepared: - 5-n-octanoyl salicylic acid 4.00 g - Polyethylene glycol 400 18.50 g - Propylene glycol methyl ether 18.50 g - Hydroxypropylcellulose 1.50 g - Anhydrous ethanol qs 100.00 g
Cette composition se présente sous forme d'un gel. EXEMPLE 9This composition is in the form of a gel. EXAMPLE 9
On prépare la composition suivante : - Acide n-octanoyl-5 salicylique sous forme micronisée, ayant une granulométrie inférieure à 5fx 3,00 g - Propylèneglycol 6,00 g - Acide acrylique réticulé par un agent polyfonctionnel, vendu sous la dénomination CARBOPOL 940 par laThe following composition is prepared: - n-octanoyl-5 salicylic acid in micronized form, having a particle size of less than 5 × 3.00 g - Propylene glycol 6.00 g - Acrylic acid crosslinked with a polyfunctional agent, sold under the name CARBOPOL 940 by the
Société GOODRICH 0,80 g - NaOH 0,125 g - Eau qsp 100,00 gGOODRICH company 0.80 g - NaOH 0.125 g - Water qs 100.00 g
Cette composition se présente sous forme d'un gel.This composition is in the form of a gel.
On constate que lorsque ces compositions sont appliquées sur une peau présentant les signes cliniques d'un vieillissement, l'aspect de celles-ci prend une couleur plus rosée, les rides s'atténuent, les tâches telles que le lentigo sénile, disparaissent.It is found that when these compositions are applied to skin showing the clinical signs of aging, the appearance of these takes on a more rosy color, wrinkles are reduced, tasks such as senile lentigo disappear.
Les résultats permettent de conclure à l'effet anti-vieillissement de ces compositions.The results allow us to conclude that the anti-aging effect of these compositions.
Ces compositions ont également permis de constater, par mesure du pli cutané sur des souris mâles OLAC, une nette augmentation de l'épaisseur de ce pli à la suite d'un traitement consistant en l'application de ces compositions à raison de 5 jours par semaine pendant deux mois 1/2.These compositions also made it possible to note, by measuring the skin fold on male OLAC mice, a marked increase in the thickness of this fold following a treatment consisting in the application of these compositions at a rate of 5 days per week for two and a half months.
Claims (13)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU87408A LU87408A1 (en) | 1988-12-16 | 1988-12-16 | USE OF SALICYL DERIVATIVES FOR THE TREATMENT OF AGING SKIN |
| AT89403474T ATE91407T1 (en) | 1988-12-16 | 1989-12-14 | USE OF SALICYLIC ACID DERIVATIVES TO TREAT SKIN AGING. |
| EP89403474A EP0378936B1 (en) | 1988-12-16 | 1989-12-14 | Use of salicylic-acid derivatives in the treatment of aging of the skin |
| DE89403474T DE68907583T2 (en) | 1988-12-16 | 1989-12-14 | Use of salicylic acid derivatives to treat skin aging. |
| CA002005695A CA2005695C (en) | 1988-12-16 | 1989-12-15 | Use of salicylated derivatives for the treatment of skin aging |
| JP1325732A JP2659102B2 (en) | 1988-12-16 | 1989-12-15 | Composition for treating skin aging |
| US07/780,063 US5262407A (en) | 1988-12-16 | 1991-10-21 | Use of salicylic derivatives for the treatment of skin aging |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU87408A LU87408A1 (en) | 1988-12-16 | 1988-12-16 | USE OF SALICYL DERIVATIVES FOR THE TREATMENT OF AGING SKIN |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU87408A1 true LU87408A1 (en) | 1990-07-10 |
Family
ID=19731125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU87408A LU87408A1 (en) | 1988-12-16 | 1988-12-16 | USE OF SALICYL DERIVATIVES FOR THE TREATMENT OF AGING SKIN |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0378936B1 (en) |
| JP (1) | JP2659102B2 (en) |
| AT (1) | ATE91407T1 (en) |
| CA (1) | CA2005695C (en) |
| DE (1) | DE68907583T2 (en) |
| LU (1) | LU87408A1 (en) |
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| EP4447912A1 (en) | 2021-12-17 | 2024-10-23 | L'oreal | Stable composition comprising oil and water-soluble alcohol |
| WO2023112655A1 (en) | 2021-12-17 | 2023-06-22 | L'oreal | Composition comprising oil, water-soluble alcohol, and ingredient derived from nymphaeaceous plants |
| WO2023112544A1 (en) | 2021-12-17 | 2023-06-22 | L'oreal | Composition comprising oil, water-soluble alcohol, and nonionic guar gum |
| FR3131692A1 (en) | 2022-01-13 | 2023-07-14 | L'oreal | Composition comprising an oil, a water-soluble alcohol and a non-ionic guar gum |
| FR3130605B1 (en) | 2021-12-21 | 2023-11-24 | Oreal | Cosmetic composition comprising a particulate cellulose compound, hydrophobic silica airgel particles, and a semi-crystalline polymer |
| FR3130606A1 (en) | 2021-12-21 | 2023-06-23 | L'oreal | Cosmetic composition comprising a particulate cellulosic compound, particles of hydrophobic silica airgel, and a wax of plant origin |
| FR3130608B1 (en) | 2021-12-21 | 2023-11-24 | Oreal | Cosmetic composition comprising a particulate cellulose compound, hydrophobic silica airgel particles, a semi-crystalline polymer and a wax of plant origin |
| FR3131529B1 (en) | 2021-12-31 | 2025-04-18 | Oreal | Cosmetic composition customization kit |
| FR3138038A1 (en) | 2022-07-25 | 2024-01-26 | L'oreal | Composition comprising glycolipid and a citric acid derivative |
| FR3142889B1 (en) | 2022-12-08 | 2025-08-15 | Oreal | Gelled aqueous phase composition comprising ascorbic acid and at least one C-glycoside. |
| WO2025114865A1 (en) | 2023-11-30 | 2025-06-05 | L'oreal | Coacervate cleansing compositions |
| FR3158636A1 (en) | 2024-01-31 | 2025-08-01 | L'oreal | Two-phase composition, in particular cosmetic, comprising at least one plant extract, at least glycolic acid, at least one linear diol having from 3 to 8 carbon atoms |
| FR3158647A1 (en) | 2024-01-31 | 2025-08-01 | L'oreal | Composition comprising at least one extract of a plant of the Fagaceae family, at least two α-hydroxy acids, at least one β-hydroxy acid or its derivatives and at least one phosphonic derivative |
| WO2025181601A1 (en) | 2024-02-29 | 2025-09-04 | L'oreal | Cosmetic composition for acne care |
| WO2025181773A1 (en) | 2024-02-29 | 2025-09-04 | L'oreal | Composition comprising biosurfactant and salicylic acid |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4499295A (en) * | 1983-05-09 | 1985-02-12 | G. D. Searle & Co. | Protease inhibitors |
| FR2581542B1 (en) * | 1985-05-07 | 1988-02-19 | Oreal | TOPICAL COMPOSITIONS FOR THE TREATMENT OF SKIN BASED ON SALICYLIC ACID DERIVATIVES |
| FR2607498B1 (en) * | 1986-12-01 | 1991-04-05 | Oreal | NOVEL LIPOPHILIC SALICYLATES OF QUATERNARY AMMONIUMS, THEIR USE IN COSMETICS AND DERMOPHARMACY |
-
1988
- 1988-12-16 LU LU87408A patent/LU87408A1/en unknown
-
1989
- 1989-12-14 EP EP89403474A patent/EP0378936B1/en not_active Expired - Lifetime
- 1989-12-14 DE DE89403474T patent/DE68907583T2/en not_active Expired - Lifetime
- 1989-12-14 AT AT89403474T patent/ATE91407T1/en not_active IP Right Cessation
- 1989-12-15 JP JP1325732A patent/JP2659102B2/en not_active Expired - Lifetime
- 1989-12-15 CA CA002005695A patent/CA2005695C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0378936B1 (en) | 1993-07-14 |
| EP0378936A3 (en) | 1990-08-08 |
| JPH02218602A (en) | 1990-08-31 |
| ATE91407T1 (en) | 1993-07-15 |
| DE68907583D1 (en) | 1993-08-19 |
| JP2659102B2 (en) | 1997-09-30 |
| EP0378936A2 (en) | 1990-07-25 |
| CA2005695A1 (en) | 1990-06-16 |
| CA2005695C (en) | 1998-02-10 |
| DE68907583T2 (en) | 1993-10-28 |
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