ITMI991895A1 - SKIN DEPIGMENTANTS - Google Patents
SKIN DEPIGMENTANTS Download PDFInfo
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- ITMI991895A1 ITMI991895A1 IT1999MI001895A ITMI991895A ITMI991895A1 IT MI991895 A1 ITMI991895 A1 IT MI991895A1 IT 1999MI001895 A IT1999MI001895 A IT 1999MI001895A IT MI991895 A ITMI991895 A IT MI991895A IT MI991895 A1 ITMI991895 A1 IT MI991895A1
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- IT
- Italy
- Prior art keywords
- cosmetic composition
- substance according
- acid
- substance
- depigmenting
- Prior art date
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Description
D E S C R I Z I ON E DESCRIPTION
Annessa a domanda di brevetto d’INVENZIONE INDUSTRIALE avente per titolo: Attached to an INDUSTRIAL INVENTION patent application entitled:
DEPIGMENTANTI CUTANEI SKIN DEPIGMENTANTS
La presente invenzione si riferisce a composizioni cosmetiche contenenti sostanze a struttura idrossistilbenica e pir(id)onica. The present invention relates to cosmetic compositions containing substances with hydroxystylbene and pyr (id) onic structure.
In particolare, a presente invenzione si riferisce a composizioni cosmetiche utili nel trattamento di depigmentazione di ipercromie cutanee di natura melanica o emosiderinica. In particular, the present invention relates to cosmetic compositions useful in the depigmentation treatment of skin hyperchromias of a melanic or hemosiderin nature.
Talune tra le sostanze a struttura idrossistilbenica o pir(id)onica sono state sintetizzate per la prima volta e costituiscono quindi un ulteriore oggetto inventivo. Some of the substances with a hydroxystylbene or pyr (id) onic structure have been synthesized for the first time and therefore constitute a further inventive object.
L’eziologia iperpigmentante si ricollega ad eventi eterogenei, che comprendono l’iperpigmentazione locale da farmaci (esempio da Ca-antagonisti), il melasma cianico, il chiasma gravidico, il melasma senile, la sovra-risposta melanica eterologa conseguente a sclerodermia, la risposta post-infìammatoria o traumatica, oppure risponde all’esigenza di ridurre la colorazione etnica di individui di ceppo afro o asiatico. The hyperpigmentative etiology is linked to heterogeneous events, which include local drug hyperpigmentation (for example by Ca-antagonists), cyanic melasma, gravidaric chiasm, senile melasma, heterologous melanic over-response following scleroderma, response post-inflammatory or traumatic, or responds to the need to reduce the ethnic coloration of individuals of Afro or Asian stock.
La prima crema depigmentante apparve in Corea 50 anni fa, e corrispondeva al bisogno estetico delle donne orientali di esibire una complessione pallida. Conteneva un composto mercuriale, la cui azione. era basata sulla sostituzione del rame, oligoelemento essenziale quale co-fattore della tirosinasi. Il composto mercuriale é attualmente bandito per gli effetti nefrotossici. The first depigmenting cream appeared in Korea 50 years ago, and corresponded to the aesthetic need of oriental women to exhibit a pale complexion. It contained a mercurial compound, the action of which. it was based on the substitution of copper, an essential trace element as a co-factor of tyrosinase. The mercurial compound is currently banned for its nephrotoxic effects.
Vari composti naturali sono in grado di svolgere una parziale azione inibente della sintesi o dell’attività tirosinasica, ad esempio glucosammine, galattosammine, mannosammine, ed alcuni estratti vegetali, la cui attività è presumibilmente legata al blocco dei radicali liberi stimolatori della melanogenesi. Various natural compounds are able to perform a partial inhibiting action of the synthesis or tyrosinase activity, for example glucosamines, galactosamines, mannosamines, and some plant extracts, whose activity is presumably linked to the blocking of free radicals that stimulate melanogenesis.
Anche antiossidanti come le vitamina C ed E ed i loro esteri hanno blande capacità depigmentanti, per parziale inibizione della melanogenesi, tuttavia con effetti insufficienti agli scopi estetici richiesti. Even antioxidants such as vitamins C and E and their esters have mild depigmenting abilities, due to partial inhibition of melanogenesis, however with insufficient effects for the required aesthetic purposes.
L’acido azelaico, introdotto come trattamento anti-acne come Azelex<® >(Allergan, Irvine, USA), trova uso estemporaneo quale depigmentante avendo dimostrato linibizione competitiva della tirosinasi e della sintesi del DNA nel sito melanosomico. Azelaic acid, introduced as an anti-acne treatment such as Azelex <®> (Allergan, Irvine, USA), finds extemporaneous use as a depigmentant having demonstrated the competitive inhibition of tyrosinase and DNA synthesis at the melanosomal site.
Attualmente il prodotto maggiormente utilizzato sono composizioni con il 2% di idrochinone, substrato ad azione antagonista e competitiva della tirosina nei confronti dell’enzima tirosinasi, frequentemente associata agli alfa idrossiacidi. Currently the most used product are compositions with 2% hydroquinone, a substrate with an antagonistic and competitive action of tyrosine against the enzyme tyrosinase, frequently associated with alpha hydroxy acids.
In particolare l’acido glicolico è stato utilizzato con successo in combinazione con l’idrochinone (Lim JT, Tham SN Dermatol Surg, 23 (3): 177-179, 1997), con la tretinoina (Lawrence N, Cox SE, Brody HJ, J. Am. Acad. Dermatol., 36 (4). 589-93, 1997) e con l’acido cogico (Garcia A, Fulton JE, Dermatol Surg, 22(5): 443-7, 1996). In particular, glycolic acid has been used successfully in combination with hydroquinone (Lim JT, Tham SN Dermatol Surg, 23 (3): 177-179, 1997), with tretinoin (Lawrence N, Cox SE, Brody HJ , J. Am. Acad. Dermatol., 36 (4). 589-93, 1997) and with kojic acid (Garcia A, Fulton JE, Dermatol Surg, 22 (5): 443-7, 1996).
Tuttavia, l’acido cogico risulta essere irritante e possibile fonte di ipocromie croniche (Iurassich S, Santoro M, Rossi E, G. Ital. Venereol., 132:443-4, 1997), cosi come l’uso prolungato di creme all’idrochinone 2 % coincide con un’elevata frequenza di iperpigmentazione granuloso-localizzata e formazione di fibre elastotiche (Sylla R et al, Dakar Med., 3, 223-6, 1994), con casi di ipopigmentazione e vitiligine da uso prolungato. However, kojic acid appears to be an irritant and a possible source of chronic hypochromias (Iurassich S, Santoro M, Rossi E, G. Ital. Venereol., 132: 443-4, 1997), as well as the prolonged use of 2% hydroquinone coincides with a high frequency of granular-localized hyperpigmentation and formation of elastotic fibers (Sylla R et al, Dakar Med., 3, 223-6, 1994), with cases of hypopigmentation and vitiligo from prolonged use.
Le sostanze depigmentanti risultano, pertanto, o parzialmente efficaci oppure possiedono controindicazioni nell’applicazione topica. Depigmenting substances are therefore either partially effective or have contraindications in topical application.
La richiedente ha trovato che sostanze di struttura (poliidrossi)stilbenica sono efficaci nel trattamento delle forme iperpigmentative, in particolare di origine melanica. The Applicant has found that substances with a stilbenic (polyhydroxy) structure are effective in the treatment of hyperpigmentative forms, in particular of melanic origin.
Un oggetto della presente invenzione riguarda una composizione cosmetica contenenti sostanze di formula generale: An object of the present invention relates to a cosmetic composition containing substances of general formula:
dove R<1>, R<2>, R<3>, R<4>, ciascuno indipendentemente, è uguale a H o OH, e con un numero di R=OH compreso tra 2 e 3 ; where R <1>, R <2>, R <3>, R <4>, each independently, is equal to H or OH, and with a number of R = OH between 2 and 3;
dette sostanze utili per la preparazione di composizioni cosmetiche ad azione depigmentante. said substances useful for the preparation of cosmetic compositions with depigmenting action.
Una tipologia iperpigmentativa particolare riguarda i depositi emosiderinici da traumi, ematomi, o da postumi dell’operazione di sclerodermia. Nel trattamento estetico di sclerotizzazione venoso-varicosa e capillare l’incidenza di eventi locali iperpegmentativi irrisolti è intorno al 20 % delle pazienti trattate. A particular type of hyperpigmentation concerns the hemosiderin deposits from trauma, hematomas, or the after-effects of the scleroderma operation. In the aesthetic treatment of venous-varicose and capillary sclerosis, the incidence of unresolved local hyperpegmentative events is around 20% of the patients treated.
In questo ambito, la formazione di macchie pigmentate pare essere il risultato dalla combinazione tra l’extravasamento emoglobinico, con formazione di deposito emosiderinico, e liperattività melanica mediata dal processo infiammatorio conseguente all’extravasamento stesso. Si é osservato un’aumento dell’incidenza pigmentativa per trattamento di venulectasi blu, al contrario del trattamento di telengiectasie rosse, con indicazioni riguardo la fragilità capillare quale causa predisponente. In this context, the formation of pigmented spots appears to be the result of the combination of hemoglobin extravasation, with the formation of hemosiderin deposit, and melanic hyperactivity mediated by the inflammatory process resulting from the extravasation itself. An increase in the incidence of pigmentation was observed for the treatment of blue venulectasis, as opposed to the treatment of red telengiectasis, with indications regarding capillary fragility as a predisposing cause.
Tale condizione può verificarsi in altre condizioni traumatiche, ad esempio a seguito di ematomi, al trattamento di follicolosi, all’incisione di tatuaggi, ecc. This condition can occur in other traumatic conditions, for example as a result of hematomas, the treatment of folliculosis, the incision of tattoos, etc.
Il trattamento di depositi emosiderinici ha coinvolto l’uso dell’esfoliazione (ad esempio con acido tricloroacetico), della crioterapia, dell’acido retinoico, mentre i trattamenti specifici miratri alla chelazione del ferro emosiderinico si sono rivolti all’applicazione di creme contenenti EDTA, oppure l’iniezione intradermica di un chetante specifico del ferro, la desferoxamina. Nessuno di questi ha dato risultati definitivi sull’inestetismo iperpigmentativo. The treatment of hemosiderin deposits involved the use of exfoliation (for example with trichloroacetic acid), cryotherapy, retinoic acid, while specific treatments aimed at the chelation of hemosiderin iron have turned to the application of creams containing EDTA, or the intradermal injection of a specific iron ketant, desferoxamine. None of these gave definitive results on hyperpigmentative imperfections.
La richiedente ha ora inoltre trovato che alcune sostanze tipo 4-idrossi-3 -pironi, -piridoni, definibili congiuntamente come 4-idrossi-3-pir(id)oni, che si dimostrano efficaci nel trattamento delle forme iperpigmentative, in particolare di origine emosiderinica. The Applicant has now also found that some substances such as 4-hydroxy-3-pyrones, -pyridones, jointly defined as 4-hydroxy-3-pir (id) oni, which prove effective in the treatment of hyperpigmentative forms, in particular of hemosiderin.
Un oggetto della presente invenzione riguarda una composizione cosmetica contenenti sostanze di formula generale: An object of the present invention relates to a cosmetic composition containing substances of general formula:
dove: X è O o N — Y, where: X is O or N - Y,
R<5 >è H, metile o etile; R <5> is H, methyl or ethyl;
Y è un aminoacido o R<6>; Y is an amino acid or R <6>;
R<6 >è un alchile lineare o ramificato o ciclico, saturo o insaturo od ossidrilato; dette sostanze utili per la preparazione di composizioni cosmetiche ad azione depigmentante. R <6> is a linear or branched or cyclic, saturated or unsaturated or hydroxylated alkyl; said substances useful for the preparation of cosmetic compositions with depigmenting action.
Talune delle sostanze ad azione depigmentante oggetto della presente invenzione sono note, altre sono state sintetizzate per la prima volta in questo ambito, pertanto costituiscono ulteriore oggetto inventivo. Some of the substances with depigmenting action of the present invention are known, others have been synthesized for the first time in this context, therefore they constitute a further inventive object.
Tra i (poliidrossi)stilbeni è noto lossiresveratrolo (2,3’,4,5’-tetraidrossistilbene, Among the (polyhydroxy) stilbenes, lossiresveratrol (2.3 ', 4.5'-tetrahydroxystilbene,
che è stato estratto e caratterizzato nel gelso (Morus alba). which has been extracted and characterized in the mulberry tree (Morus alba).
Nuovi analoghi strutturali a struttura (poliidrossi)stilbenica oggetto della presente invenzione comprendono, tra gli altri, il 2,2’,4,4’-tetraidrossistilbene, il 2, 3’, 4, 4’-tetraidrossistilbene ed il 2,3’,4,5’,6’-pentaidrossistilbene. New structural analogs with a (polyhydroxy) stilbenic structure object of the present invention include, among others, 2,2 ', 4,4'-tetrahydroxystilbene, 2, 3', 4, 4'-tetrahydroxystilbene and 2,3 ' , 4,5 ', 6'-pentahydroxystylbene.
I (poliidrossi)stilbeni si ottengono mediante reazione di Wittig tra i derivati O-protetti (come dimetil-terbutil-silano) dell’ilide del fosforo del 2,4-diidrossibenzil cloruro e l’aldeide 3,5- 2,4- o 3,4-diidrosibenzoica o l’aldeide gallica, con sblocco successivo delle protezioni mediante idrogenazione a 5 atm su Pd/C in metanolo. The (polyhydroxy) stilbenes are obtained by the Wittig reaction between the O-protected derivatives (such as dimethyl-terbutyl-silane) of the phosphorus ilide of 2,4-dihydroxybenzyl chloride and the aldehyde 3,5- 2,4- or 3,4-dihydrosibenzoic or gallic aldehyde, with subsequent release of the protections by hydrogenation at 5 atm on Pd / C in methanol.
Della serie dei 4-idrossi-3 -pironi sono noti l’acido piromeconico ottenuto per riscaldamento dell’acido comenico di origine fermentativa, il maltolo From the 4-hydroxy-3-pyrones series, pyromeconic acid is known, obtained by heating the comenic acid of fermentative origin, maltol
contenuto nella cicoria, negli aghi di pino e nella corteccia del larice; l’etilmaltolo contained in chicory, pine needles and larch bark; ethylmaltol
nota fragranza alimentare. known food fragrance.
Data la non disponibilità commerciale dell’acido comenico, abbiamo sviluppato un procedimento di sintesi dell’acido piromeconico a partire dall’alcol furfurilico per trattamento con cloro in soluzione idrometanolica. Given the commercial unavailability of comenic acid, we have developed a process for the synthesis of pyromeconic acid starting from furfuryl alcohol by treatment with chlorine in a hydromethanolic solution.
Detto procedimento non era noto, e costituisce pertanto un ulteriore oggetto inventivo. Said process was not known, and therefore constitutes a further inventive object.
Della serie dei l,2-dialchil-4-idrossi-3-piridoni sono noti il deferiprone Deferiprone is known from the 1,2-dialkyl-4-hydroxy-3-pyridones series.
ed una serie di omologhi alchilici lineari sperimentati nella terapia and a series of linear alkyl homologs tested in therapy
chetante di rimozione delle sideremie da politransfusione, talora formati spontaneamente dai 4-idrossi-3 -pironi per reazione di Mannich, ad esempio del maltolo con animine primarie o glieina, all’atto della cottura dei cibi. ketant for removing sideremias from polytransfusion, sometimes spontaneously formed by 4-hydroxy-3-pyrons by Mannich reaction, for example of maltol with primary animins or glyein, when cooking food.
A partire dall’acido pirocomenico per reazione con ammine primarie e amminoacidi in soluzione acquosa o idroalcolica abbiamo sviluppato la serie dei 4-idrossi-3-piridoni N-sostituiti con gruppo alchilico o amminoacìdico, non noti fino ad ora, che costituiscono pertanto un ulteriore oggetto inventivo. Starting from pyrochomenic acid by reaction with primary amines and amino acids in aqueous or hydroalcoholic solution we have developed the series of N-substituted 4-hydroxy-3-pyridones with alkyl or amino acid group, not known until now, which therefore constitute a further inventive object.
Le nuove sostanze comprendono, tuttavia in modo non esclusivo, i 4-idrossi-3-piridoni sostituiti come 1-metil, 1-etil, 1-isopropil, 1-N-valina, 1-N-leucina, 1-N-isoleucina. The new substances include, however not exclusively, the substituted 4-hydroxy-3-pyridones such as 1-methyl, 1-ethyl, 1-isopropyl, 1-N-valine, 1-N-leucine, 1-N-isoleucine .
La composizione secondo l'invenzione possono comprendere anche un veicolo cosmeticamente accettabile che agisca come dilutante, disperdente o veicolo delle sostanze di interesse nella composizione cosmetica. The composition according to the invention may also comprise a cosmetically acceptable carrier which acts as a dilutant, dispersant or carrier of the substances of interest in the cosmetic composition.
La quantità del veicolo può variare da 50% a 99,9%, preferibilmente da 95% a 99% in peso della composizione totale. Veicoli diversi dall’acqua possono includere degli emollienti liquidi o solidi, i siliconi ed i solventi. The amount of the carrier can vary from 50% to 99.9%, preferably from 95% to 99% by weight of the total composition. Vehicles other than water may include liquid or solid emollients, silicones and solvents.
I depigmentanti della presente invenzione possono essere applicati sulla cute in soluzione di solventi quali il DMSO, oppure possono beneficiare della presenza di ingredienti cosmetici in grado di migliorarne Γ applicabilità, facilitarne la penetrazione e/o incrementare l’efficacia del trattamento depigmentante. The depigmenting agents of the present invention can be applied to the skin in a solution of solvents such as DMSO, or they can benefit from the presence of cosmetic ingredients capable of improving their applicability, facilitating their penetration and / or increasing the effectiveness of the depigmenting treatment.
Oli e lipidi possono essere combinati all’acqua mediante emulsionanti (“tensioattivi”), a dare emulsioni o/a o a/o in fimzione dell'equilibrio idrofilico-lipofilico medio (HLB) del sistema emulsionante. I tensioattivi può essere incorporati in quantità compresa tra 0,5% a 30%, preferibilmente da 1% a 15% in peso. Oils and lipids can be combined with water by means of emulsifiers ("surfactants"), to give emulsions either / to or to / or in function of the average hydrophilic-lipophilic balance (HLB) of the emulsifying system. The surfactants can be incorporated in quantities ranging from 0.5% to 30%, preferably from 1% to 15% by weight.
I tensioattivi cationici, nonionici, anionici, amfoterici e loro combinazioni possono essere utilmente impiegati. Tra i tensioattivi nonionici si citano gli alcossilati di alcoli e acidi grassi o di sorbitali, il poliossipropilene e poliossietilene, gli alchil poliglicosidi; tra i tensioattivi anionici i saponi di acidi grassi, il sodio lauril solfato o lauril etere solfato, gli alchil benzensulfonati, i mono e/o dialchil fosfati e similari; tra i tensioattivi amfoterici gli ossidi di dialchilammine, i vari tipi di betaine, i fosfolipidi e i ceramidi naturali. Cationic, nonionic, anionic, amphoteric surfactants and their combinations can be usefully employed. Among the nonionic surfactants, the alkoxylates of alcohols and fatty acids or sorbitals, polyoxypropylene and polyoxyethylene, alkyl polyglycosides are mentioned; among the anionic surfactants, fatty acid soaps, sodium lauryl sulfate or lauryl ether sulfate, alkyl benzenesulfonates, mono and / or dialkyl phosphates and the like; among the amphoteric surfactants the dialkylamine oxides, the various types of betaines, phospholipids and natural ceramides.
Un addensante può essere presente in quantità da 0,1% a 10% in peso di una composizione a base acquosa, preferibilmente da 0,5% a 5% in peso. Esempi di addensanti sono i poliacrilati reticolati (Carbopol<®>), e gomme come la xantan, carragenina, gelatina, karaia, e pectina. A thickener can be present in an amount from 0.1% to 10% by weight of an aqueous-based composition, preferably from 0.5% to 5% by weight. Examples of thickeners are cross-linked polyacrylates (Carbopol <®>), and gums such as xanthan, carrageenan, gelatin, karaia, and pectin.
Le composizioni cosmetiche acquose devono essere preservati con i conservanti dalla crescita di microrganismi, ad esempio con gli alchil esteri dell’ acido pidrossibenzoico, idantoine, parabeni, imidazolidinil urea, sodio deidroacetato, benzil alcol, e una gamma di composti ad ammonio quaternario, in quantità tra 0,2% e 1% in peso. Aqueous cosmetic compositions must be preserved with preservatives from the growth of microorganisms, for example with hydroxybenzoic acid alkyl esters, hydantoins, parabens, imidazolidinyl urea, sodium dehydroacetate, benzyl alcohol, and a range of quaternary ammonium compounds, in quantities between 0.2% and 1% by weight.
Nelle composizioni cosmetiche anidre possono essere presenti i siliconi, ad esempio quelli con viscosità che variano da 10 a 10<7 >centistokes a 25° C, e loro miscele, in quantità da 5% a 95% in peso. In the anhydrous cosmetic compositions, silicones can be present, for example those with viscosities ranging from 10 to 10 <7> centistokes at 25 ° C, and their mixtures, in quantities ranging from 5% to 95% by weight.
I filtri solari possono essere incorporati nelle composizioni cosmetiche della presente invenzione, ad esempio i derivativi del PABA, del benzofenone, e i cinnamati, in quantità dipendente dal grado di protezione UV desiderato. The sunscreens can be incorporated in the cosmetic compositions of the present invention, for example the derivatives of PABA, benzophenone, and cinnamates, in an amount depending on the desired degree of UV protection.
Altri ingredienti aggiuntivi possono essere ulteriormente incorporati, che possono includere coloranti e pigmenti, opacizzanti, profumi, ecc. La quantità di questi materiali può variare da 0,001% a 20% in peso della composizione. Other additional ingredients can be further incorporated, which can include dyes and pigments, opacifiers, perfumes, etc. The amount of these materials can vary from 0.001% to 20% by weight of the composition.
In una realizzazione preferita della presente invenzione, le sostanze depigmentanti della presente invenzione sono utilizzate in combinazione con altre sostanze funzionali Un esempio di sostanze funzionali sono gli alfa- e beta- idrossiacidi. A concentrazioni medie gli idrossiacidi agiscono per inibizione dell’azione enzimatica di solfato transferasi, fosfotransferasi e fosfochinasi dei mucopolisaccaridi, con conseguente riduzione delle forze di coesione comeocitarie, quindi facilitando l’azione dei depigmentanti. In a preferred embodiment of the present invention, the depigmenting substances of the present invention are used in combination with other functional substances. An example of functional substances are alpha- and beta-hydroxy acids. At average concentrations, hydroxy acids act by inhibiting the enzymatic action of sulfate transferase, phosphotransferase and phosphokinase of mucopolysaccharides, resulting in a reduction of the cohesion forces asocytes, thus facilitating the action of depigmenting agents.
Tra gli alfa idrossiacidi é preferito l’acido glicolico, per le caratteristiche di ottima capacità penetrante dovute al limitato ingombro sierico della molecola, in quantità da 1% a 50%, preferibilmente da 5% a 12% in peso. Among the alpha hydroxy acids glycolic acid is preferred, due to the characteristics of excellent penetrating capacity due to the limited serum bulk of the molecule, in quantities from 1% to 50%, preferably from 5% to 12% by weight.
Tra i beta-idrossiacidi é preferito l’acido salicilico per le qualità di esfoiiante energico dello strato epidermico, inattivo e quindi non irritante a livello del derma, in quantità da 0,1% a 10%, preferibilmente da 1% a 5% in peso. Among the beta-hydroxyacids, salicylic acid is preferred due to its qualities as an energetic exfoliator of the epidermal layer, inactive and therefore non-irritating at the level of the dermis, in quantities from 0.1% to 10%, preferably from 1% to 5% in weight.
Un’altra combinazione preferita nella presente invenzione è costituita da altri depigmentanti, ad esempio l’idrochinone, l’arbutina e l’acido cogico. Another preferred combination in the present invention consists of other depigmentants, for example hydroquinone, arbutin and kojic acid.
Altri tipi di ingredienti attivi sono considerati nella presente invenzione. Sebbene non limitato a queste categorie, includono gli antirughe ed antiinfoammatori, ad esempio i derivati glicirrizinici, i flavonoidi, l’alfa-bisabololo, l’acido rosmarinico, l’azulene, l’asiaticoside, la ruscogenina, lescina, l’acido betulinico, il retinolo e suoi derivativi, il tocoferolo e i suoi derivativi. Other types of active ingredients are considered in the present invention. Although not limited to these categories, they include anti-wrinkle and anti-inflammatory drugs, such as glycyrrhizin derivatives, flavonoids, alpha-bisabolol, rosmarinic acid, azulene, asiaticoside, ruscogenin, lescin, betulinic acid. , retinol and its derivatives, tocopherol and its derivatives.
Le composizioni della presente invenzione possono essere usate formulate in forma di composizioni cosmetiche quali pomate, creme, unguenti, gel, tinture, latti, lipogel, ed altri preparati trifasici o/a o a/o comunemente utilizzabili per il trattamento topico. The compositions of the present invention can be used formulated in the form of cosmetic compositions such as ointments, creams, ointments, gels, tinctures, milks, lipogels, and other triphasic preparations either / a or a / or commonly usable for topical treatment.
Un esempio di composizioni sono creme o gel contenenti i liposomi o microemulsioni, per l’eccellente biodisponibilità con diffusione intracutanea, quindi utilizzabili in alterazioni profonde della pigmentazione emosiderinica o metanica. An example of compositions are creams or gels containing liposomes or microemulsions, due to their excellent bioavailability with intracutaneous diffusion, therefore usable in deep alterations of hemosiderin or methane pigmentation.
L’incorporazione dei principi attivi in composizioni in forme a rilascio transdermico controllato, quali cerotti, bendaggi e fasciature, sono indicate per applicazioni prolungate in aree limitate. The incorporation of the active ingredients in compositions in controlled transdermal release forms, such as plasters, bandages and dressings, are indicated for prolonged applications in limited areas.
Per pelli sebose o ipercheratiniche risultano di particolare interesse le composizioni acquose a basso contenuto oleoso, ad esempio gel o microdispersioni gelificate (lipogel), in grado di rilasciare le sostanze depigmentanti veicolate da un alfa- o beta- idrossiacido. For sebum or hyperkeratin skins, the aqueous compositions with a low oily content, for example gels or gelled microdispersions (lipogels), capable of releasing depigmenting substances carried by an alpha- or beta-hydroxy acid, are of particular interest.
Le sostanze depigmentanti possono essere presenti in composizioni cosmetiche in quantità da 0,001% a 20%, preferibilmente da 0,1% a 2% in peso. The depigmenting substances can be present in cosmetic compositions in quantities ranging from 0.001% to 20%, preferably from 0.1% to 2% by weight.
I dosaggi complessivi possono variare da 5 mg fino a 5000 mg/die, in base alla risposta individuale e all’estenzione dell’area cutanea interessata a forme di melasma senile, chiasma gravidico, iperpigmentazione post-infiammatoria e traumatica, per il trattamento della pigmentazione etnica, dei depositi emosiderinici conseguenti a sclerodermia, ematoma e tattuaggio. The overall dosages can vary from 5 mg up to 5000 mg / day, based on the individual response and extension of the affected skin area to forms of senile melasma, chiasma gravidarum, post-inflammatory and traumatic hyperpigmentation, for the treatment of pigmentation. ethnic, hemosiderin deposits resulting from scleroderma, hematoma and tactile.
Risultati evidenti sono ottenibili in patologie degenerative che necessitano di un costante rifornimento del principio attivo in quantità sufficiente a produrre gli effetti richiesti. Obvious results can be obtained in degenerative diseases that require a constant supply of the active ingredient in sufficient quantity to produce the required effects.
Gli esempi che seguono servono ad illustrare ulteriormente l’invenzione e non devono essere ritenuti assolutamente limitativi. The following examples serve to further illustrate the invention and should not be considered absolutely limiting.
Esempio Preparativo I - Sintesi di fpoliidrossilstilbeni Preparative Example I - Synthesis of polyhydroxystilbenes
La sintesi è condotta seondo il procedimento descritto da Orsini F et al. (J Nat Prod, 60, 11, 1997), applicando la reazione di Wittig dei derivati O-protetti (come dimetilterbutil-silano) dell’ilide del fosforo del 2,4-diidrossibenzil cloruro e l’aldeide 3,5- 2,4- o 3,4-diidrosibenzoica o l’aldeide gallica, con sblocco successivo delle protezioni mediante idrogenazione a 5 atm su Pd/C in metanolo a dare, rispettivamente, 2, 3’, 4,4’-tetraidrossistilbene e 2,3’,4,5’,6’-pentaidrossistilbene. The synthesis is carried out according to the procedure described by Orsini F et al. (J Nat Prod, 60, 11, 1997), applying the Wittig reaction of the O-protected derivatives (such as dimethylterbutyl-silane) of the phosphorus ilide of 2,4-dihydroxybenzyl chloride and aldehyde 3,5-2, 4- or 3,4-dihydrosibenzoic or gallic aldehyde, with subsequent release of the protections by hydrogenation at 5 atm on Pd / C in methanol to give, respectively, 2, 3 ', 4,4'-tetrahydroxystilbene and 2,3 ', 4,5', 6'-pentahydroxystilbene.
Esempio Preparativo II - Sintesi di acido piromeconico Preparative Example II - Synthesis of pyromeconic acid
74,6 g di cloro gas (1,05 moli) sono gorgogliati sotto agitazione sul fondo di un reattore contenente 15 ml di metanolo: acqua 2:3 (v/v), previamente raffreddati a -10° C. 74.6 g of chlorine gas (1.05 moles) are bubbled under stirring at the bottom of a reactor containing 15 ml of methanol: water 2: 3 (v / v), previously cooled to -10 ° C.
Contemporaneamente si addiziona una soluzione di 49 g di alcol furfurilico (0,5 moli) sciolti in 50 ml di metanolo: acqua 5: 1 (v/v). Quando laggiunta di alcol furfurilico è completata, il cloro immesso ammonta a 2/3 del totale, la restante porzione (1/3) è immessa successivamente, mantenendo il sistema a temperatura non superiore a -5° C. At the same time, a solution of 49 g of furfuryl alcohol (0.5 moles) dissolved in 50 ml of methanol: water 5: 1 (v / v) is added. When the addition of furfuryl alcohol is completed, the chlorine introduced amounts to 2/3 of the total, the remaining portion (1/3) is subsequently introduced, keeping the system at a temperature not exceeding -5 ° C.
Quindi si scalda a 90° C, distillando parte del metanolo, e proseguendo il riscaldamento a 90-50° C per circa 3 ore. Then it is heated to 90 ° C, distilling part of the methanol, and continuing the heating at 90-50 ° C for about 3 hours.
La soluzione è raffreddata a temperatura ambiente, si separano circa 7 g di materiale pecioso, e si aggiusta quindi a pH 2,2 con NaOH 50% (circa 45 mi), mantenendo a temperatura non superiore a 40° C sotto agitazione. The solution is cooled to room temperature, about 7 g of pitchy material are separated, and then adjusted to pH 2.2 with 50% NaOH (about 45 ml), maintaining at a temperature not exceeding 40 ° C under stirring.
Raffreddando a 5° C precipita acido piromeconico, che é filtrato e riscristalliazato 2 volte da metanolo, fornendo 25 g di un prodotto bianco semicristallino (resa 51%). By cooling to 5 ° C pyromeconic acid precipitates, which is filtered and re-crystallized twice by methanol, giving 25 g of a semi-crystalline white product (yield 51%).
Esempio Preparativo IH - Sintesi di l-alchil-3-idrossi-4-piridone Preparative Example 1H - Synthesis of 1-alkyl-3-hydroxy-4-pyridone
0,98 g di acido piromeconico (10 mmoli) vengono sciolti in 40 ml di acqua contenente 2,4 ml di metilammina 40% (circa 3 equivalenti). 0.98 g of pyromeconic acid (10 mmoles) are dissolved in 40 ml of water containing 2.4 ml of 40% methylamine (about 3 equivalents).
Si scalda a riflusso per 7 ore, quindi si raffredda e si aggiunge carbone attivo, e si lascia a riposo per 30 minuti. La soluzione, con aspetto di soluzione bruno-scura, viene filtrata e quindi svaporata in vuoto scaldando, a dare un solido bruno scuro, che viene ricristallizato 3 volte da acqua, a dare 0,42 g di prodotto aciculare bianco, resa 38%. The mixture is refluxed for 7 hours, then it is cooled and activated carbon is added, and it is left to stand for 30 minutes. The solution, with the appearance of a dark brown solution, is filtered and then evaporated under vacuum by heating, to give a dark brown solid, which is recrystallized 3 times by water, to give 0.42 g of white acicular product, yield 38%.
Il prodotto essicato in stufa e macinato è 1-metil-3-idrossi-4-piridone, M = 111. Esempio Preparativo VI - Sintesi di 3-idrossi-4-piridone. 1-N-amminoacidi The oven dried and ground product is 1-methyl-3-hydroxy-4-pyridone, M = 111. Preparative Example VI - Synthesis of 3-hydroxy-4-pyridone. 1-N-amino acids
Si segue la procedura dell’Esempio Preparativo ΙI ma sostituendo la metialmmina con 3 g di glieina, a dare l-carbossimetil-3-idrossi-4-piridone con rese del 23%. The procedure of Preparative Example ΙI is followed but replacing the methylamine with 3 g of gliein, to give 1-carboxymethyl-3-hydroxy-4-pyridone with yields of 23%.
Esempio I - Inibizione della tirosinasi in vitro Example I - Inhibition of tyrosinase in vitro
In 120 ul di tampone fosfato 67 mM (pH 6,8) sciolgono 0,197 mg di L-dopa (1 umole), alla quale si aggiungono 40 ul della soluzione dei campioni a varie concentrazioni nella soluzione del tampone. Sono immessi in piastre, alle quali si aggiungono 40 ul di tirosinasi da fungo (Sigma- Aldrich, USA) a 125 U/ml, si mescola e si lascia in incubazione a 37° C per 20 minuti. In 120 ul of 67 mM phosphate buffer (pH 6.8) dissolve 0.197 mg of L-dopa (1 umole), to which 40 ul of the sample solution at various concentrations in the buffer solution are added. They are placed in plates, to which 40 ul of mushroom tyrosinase (Sigma-Aldrich, USA) are added at 125 U / ml, mixed and left to incubate at 37 ° C for 20 minutes.
Viene quindi misurata la densità ottica in microcuvette a 492 nm, calcolando la percentuale di inibizione rispetto al valore fornito da ima soluzione di 120 ul di tampone fosfato e 40 ul di tirosinasi su 1 umole di L-dopa. Per confronto si utilizza l’acido cogico, di cui si conoscono le proprietà depigmentanti. The optical density is then measured in microcuvettes at 492 nm, calculating the percentage of inhibition with respect to the value provided by a solution of 120 ul of phosphate buffer and 40 ul of tyrosinase on 1 umole of L-DOPA. For comparison, kojic acid is used, whose depigmenting properties are known.
Il valore di IC50 è ottenuto mediante il programma MacALLFIT. I risultati sono illustrati nella Tabella I. The value of IC50 is obtained through the MacALLFIT program. The results are shown in Table I.
TABELLA I TABLE I
Dalla tabella si osserva che i (poliidrossi)stilbeni ed i 3 -idrossi-4-pir(id)oni privi di sostituente in posizione 2 posseggono una attività di inibizione della tirosinasi da 2 a 30 volte maggiore dell’acido cogico. From the table it is observed that the (polyhydroxy) stilbenes and the 3-hydroxy-4-pir (id) oni without substituent in position 2 possess a tyrosinase inhibition activity from 2 to 30 times greater than kojic acid.
Si evidenzia l’inattività dei 2-alchil-3 -idrossi-4-piridonì, che risulteranno invece essere dei potenziali candidati per la rimozione di macchie emosideriniche. The inactivity of 2-alkyl-3-hydroxy-4-pyridonium is highlighted, which will turn out to be potential candidates for the removal of hemosiderin stains.
Esempio I - Depigmentazione melanica con forme a rilascio controllato Example I - Melanic depigmentation with controlled release forms
Si preparano 100 g di una massa adesiva che contengono, ciascuna, rispettivamente: 100 g of an adhesive mass are prepared, each containing respectively:
Massa adesiva (A) (B) (C) (D) Adhesive mass (A) (B) (C) (D)
il film adesivo viene quindi spalmato su un film base ed una pellicola di copertura, ottenendosi cerotti in grado di cedere le sostanze depigmentanti nel corso di 24 ore, assicurandone la somministrazione continuativa. the adhesive film is then spread on a base film and a covering film, obtaining patches capable of releasing the depigmenting substances in the course of 24 hours, ensuring their continuous administration.
2 soggetti volontari di ceppo afro (provenienza Senegal) vengono fomiti di cerotti della superfice di 12 cm di composizione da A a D, delimitando le 4 aree di applicazione sulla zona ventrale, con l’istruzione di rinnovare l’applicazione del cerotto ogni 48 ore, Dopo 40 giorni di trattamento, i soggetti vengono esaminati, confrontando le 4 aree di applicazione con la colorazione della pelle circostante, non trattata. I risultati sono illustrati nella Tabella I. 2 volunteers of Afro stock (from Senegal) are supplied with patches with a surface of 12 cm of composition from A to D, delimiting the 4 areas of application on the ventral area, with the instruction to renew the application of the patch every 48 hours After 40 days of treatment, the subjects are examined, comparing the 4 application areas with the color of the surrounding, untreated skin. The results are shown in Table I.
TABELLA Π TABLE Π
Si osserva pertanto un’elevata attività depigmentante metanica dei (poliidrossi)stilbenici e del deferiprone, in parziale accordo con i risultati del test di inibizione della tirosinasi. Therefore, a high methane depigmenting activity of (polyhydroxy) stilbenes and deferiprone is observed, in partial agreement with the results of the tyrosinase inhibition test.
Esempio 111 - Depigmentazione di macchie emosideriniche con gel glicolico Example 111 - Depigmentation of hemosiderin spots with glycolic gel
Si preparano 100 g di gel al 2% di principio attivo, che contengono rispettivamente: 100 g of gel with 2% of active ingredient are prepared, which respectively contain:
Gel (A) Gel (B) Gel (C) Gel (A) Gel (B) Gel (C)
2 soggetti volontari di sesso femminile, che riportano sulle gambe alcune macchie emosideriniche persistenti (a oltre 6 mesi dal 'intervento di sclerodermia) vengono fomiti di 3 Gel A, B, C, con l’istruzione di applicarli separatamente e ripetutamente su 3 aree distinte. 2 female volunteers, who have some persistent hemosiderin spots on their legs (more than 6 months after scleroderma surgery) are provided with 3 Gels A, B, C, with the instruction to apply them separately and repeatedly on 3 distinct areas .
Dopo 30 giorni di trattamento con 3 applicazioni giornaliere di 30 minuti, seguito da lavaggio con acqua delia zona interessata, vengono valutate i risultati, il Gel A non ha apportato alcuna modifica sostanziale alla macchia sideremica, il Gel B un discreto miglioramento, mentre la zona trattata con Gel C risulta priva di traccia iperpigmentativa. After 30 days of treatment with 3 daily applications of 30 minutes, followed by washing the affected area with water, the results are evaluated, Gel A did not make any substantial changes to the iron stain, Gel B a moderate improvement, while the area treated with Gel C it is devoid of hyperpigmentative trace.
Si è in pratica constatato come la presente invenzione raggiunga gli scopi prefìssati. E' evidente che le composizioni e i metodi secondo l’invenzione sono suscettibili di varianti che ricadono nell’ambito del concetto inventivo. In practice it has been found that the present invention achieves the intended purposes. It is evident that the compositions and methods according to the invention are susceptible to variants that fall within the scope of the inventive concept.
Lo scopo dell* invenzione e' meglio definito dalle rivendicazioni, piuttosto che dagli esempi sopra riportati. The object of the invention is better defined by the claims, rather than by the examples reported above.
Claims (14)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1999MI001895A IT1316059B1 (en) | 1999-09-09 | 1999-09-09 | SKIN DEPIGMENTANTS. |
| PCT/IB2000/001275 WO2001017497A1 (en) | 1999-09-09 | 2000-09-08 | Depigmenting compositions |
| AU67201/00A AU6720100A (en) | 1999-09-09 | 2000-09-08 | Depigmenting compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1999MI001895A IT1316059B1 (en) | 1999-09-09 | 1999-09-09 | SKIN DEPIGMENTANTS. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| ITMI991895A0 ITMI991895A0 (en) | 1999-09-09 |
| ITMI991895A1 true ITMI991895A1 (en) | 2001-03-09 |
| IT1316059B1 IT1316059B1 (en) | 2003-03-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT1999MI001895A IT1316059B1 (en) | 1999-09-09 | 1999-09-09 | SKIN DEPIGMENTANTS. |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU6720100A (en) |
| IT (1) | IT1316059B1 (en) |
| WO (1) | WO2001017497A1 (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10121092A1 (en) * | 2001-04-26 | 2002-10-31 | Beiersdorf Ag | Cosmetic or dermatological formulations containing sericoside and / or plant extracts containing the same |
| ITMI20022447A1 (en) * | 2002-11-19 | 2004-05-20 | Carlo Ghisalberti | USE OF PYRIDINONS IN THE TREATMENT OF CAPILLARY PURPURE AND RELATED SKIN DISEASES. |
| ITNA20050003A1 (en) | 2005-01-24 | 2006-07-25 | Rosa Mario De | NANO-STRUCTURED PEELING GEL |
| EP2247279A1 (en) * | 2008-02-01 | 2010-11-10 | Amcol International Corporation | Improved skin brightening compositions |
| DE102009027483A1 (en) * | 2009-07-06 | 2011-01-13 | Henkel Ag & Co. Kgaa | Deodorants and antiperspirants with hair growth-minimizing or -inhibierender effect |
| SG11201805765QA (en) | 2016-01-19 | 2018-08-30 | Achromaz Pte Ltd | A cosmetic composition and the use thereof for regulating skin quality |
| EP3195854A1 (en) | 2016-01-22 | 2017-07-26 | Tomorrowlabs GmbH | Cosmetic treatment of healthy skin, in particular aged skin |
| CN115096682A (en) * | 2022-08-26 | 2022-09-23 | 北京肿瘤医院(北京大学肿瘤医院) | Method for depigmenting malignant melanoma |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57136508A (en) * | 1981-02-17 | 1982-08-23 | Sansho Seiyaku Kk | Whitening cosmetic |
| JPS59157009A (en) * | 1983-02-25 | 1984-09-06 | Yakurigaku Chuo Kenkyusho:Kk | External skin drug for suppressing formation of melanin |
| JPH0655082B2 (en) * | 1985-02-27 | 1994-07-27 | 株式会社薬理学中央研究所 | Method for preventing or recoloring body color of red seafood by .GAMMA.-pyrone derivative |
| EP0496433B1 (en) * | 1987-10-22 | 1999-03-24 | The Procter & Gamble Company | Photoprotection compositions comprising chelating agents |
| JP3988838B2 (en) * | 1996-05-29 | 2007-10-10 | 日本製粉株式会社 | Cosmetics |
| FR2787711B1 (en) * | 1998-12-29 | 2002-12-06 | C3D Sarl | COSMETIC COMPOSITION WITH DEPIGMENTING ACTIVITY AND ITS USE |
-
1999
- 1999-09-09 IT IT1999MI001895A patent/IT1316059B1/en active
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2000
- 2000-09-08 WO PCT/IB2000/001275 patent/WO2001017497A1/en active Application Filing
- 2000-09-08 AU AU67201/00A patent/AU6720100A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| IT1316059B1 (en) | 2003-03-28 |
| AU6720100A (en) | 2001-04-10 |
| ITMI991895A0 (en) | 1999-09-09 |
| WO2001017497A1 (en) | 2001-03-15 |
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