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WO2010148101A2 - Compositions topiques contenant un polymère pour libérer au moins un composé d'acide salicylique - Google Patents

Compositions topiques contenant un polymère pour libérer au moins un composé d'acide salicylique Download PDF

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Publication number
WO2010148101A2
WO2010148101A2 PCT/US2010/038842 US2010038842W WO2010148101A2 WO 2010148101 A2 WO2010148101 A2 WO 2010148101A2 US 2010038842 W US2010038842 W US 2010038842W WO 2010148101 A2 WO2010148101 A2 WO 2010148101A2
Authority
WO
WIPO (PCT)
Prior art keywords
composition
skin
acid compound
salicylic acid
polymer
Prior art date
Application number
PCT/US2010/038842
Other languages
English (en)
Other versions
WO2010148101A3 (fr
Inventor
Philippe Barbarat
Benoit Muller
Bertrand Lion
Original Assignee
L'oreal S.A.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by L'oreal S.A. filed Critical L'oreal S.A.
Publication of WO2010148101A2 publication Critical patent/WO2010148101A2/fr
Publication of WO2010148101A3 publication Critical patent/WO2010148101A3/fr

Links

Classifications

    • 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/85—Polyesters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/28—Rubbing or scrubbing compositions; Peeling or abrasive compositions; Containing exfoliants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances

Definitions

  • compositions for topical application to skin such as cosmetic or dermatologic compositions comprising at least one polymer comprising at least one salicylic acid compound and at least one dicarboxylic acid compound.
  • Such topical compositions can be used in treating or preventing skin- related conditions and/or improving skin characteristics or properties.
  • Salicylic acid compounds and other active agents are known to be useful in treating skin conditions such as, for example, acne and/or improving skin properties such as, for example, reducing the appearance of fine lines or wrinkles.
  • formulating topical compositions containing salicylic acid compound and/or other active agents can be problematic - it can be difficult to prepare a stable formulation containing salicylic acid compound and other active agents because, for example, salicylic acid compound and/or other active agents react with other ingredients commonly found in such formulations, thereby negatively affecting salicylic acid compound and/or other active agent activity or stability.
  • U.S. patent 7,122,615 and related patents disclose biocompatible aromatic polyanhydrides reportedly having improved degradation properties and processability, and "unique" therapeutic properties. However, these patents do not effectively disclose using such polyanhydrides in topical compositions, or that such polyanhydrides possess properties which could render them useful in topical compositions.
  • the present invention also relates to methods for treating or preventing skin-related conditions which can be treated or prevented using a salicylic acid compound and at least one other active agent comprising topically applying to the skin of a human a composition comprising at least one polymer comprising at least one salicylic acid compound, at least one other active agent, and at least one dicarboxylic acid compound in an amount sufficient to treat or prevent the condition.
  • the present invention further relates to methods for improving skin properties or characteristics which can be improved using a salicylic acid compound comprising topically applying to the skin of a human a composition comprising at least one polymer comprising at least one salicylic acid compound and at least one dicarboxylic acid compound in an amount sufficient to improve the property or characteristic.
  • the present invention also relates to methods for providing extended treatment to skin comprising topically applying to skin a composition comprising at least one polymer comprising at least one salicylic acid compound, at least one other active agent, and at least one dicarboxylic acid compound in an amount sufficient to treat the skin with the salicylic acid compound and/or other active agent over a period of time.
  • Skin as used herein means the hypodermis, dermis, epidermis and stratum corneum.
  • the polymer comprises a unit represented by the following formula:
  • z is preferably a number between 1 and 1 ,000, preferably between 10 and 750, and more preferably between 25 and 500, including all ranges and subranges therebetween.
  • Useful salts may be obtained by salification of a salicylic acid compound with a base.
  • Useful bases include inorganic bases such as alkali and alkaline metal hydroxides (sodium hydroxide, potassium hydroxide, and the like) or ammonia hydroxides. Organic bases may also be used for salification. Also useful are amphoteric bases. Quatermium salts such as dimethylhydroxypropyl ammonium salts can also be useful.
  • the polymer comprises a unit represented by the following formula:
  • R 5 ' represents a hydrogen atom, a linear, branched or cyclized saturated aliphatic radical containing from 1 to 18 carbon atoms or an unsaturated radical containing from 3 to 18 carbon atoms, bearing one to nine conjugated or non- conjugated double bonds, it being possible for the radicals to be substituted with at least one substituent chosen from halogen atoms (fluorine, chlorine, bromine or iodine), trifluoromethyl radicals, hydroxyl in free form or esterified with an acid containing from 1 to 6 carbon atoms, or carboxyl in free form or esterified with a lower alcohol containing from 1 to 6 carbon atoms.
  • halogen atoms fluorine, chlorine, bromine or iodine
  • Suitable salicylic acid compounds are disclosed, for example, in U.S. patent nos. 6,159,479, 5,558,871 , 4,767,750, 5,267,407, 5,667,789, and 5,580,549, and U.S. patent application publication nos. 2009/0029928 and 2004/0162272, the disclosures of all of which are incorporated by reference in their entirety.
  • the polymer has a Mw between 5,000 and 50,000, more preferably between 7,500 and 35,000, and most preferably between 9,000 and 25,000, including all ranges and subranges therebetween.
  • the polymer has a Tg between 15 and 75 0 C, more preferably between 20 and 60 0 C, and more preferably between 25 and 55 0 C, including all ranges and subranges therebetween
  • the polymer can be a homopolymer containing the same repeating unit, or it can be a copolymer containing one or more repeating units in addition to the above unit.
  • the polymer must satisfy one or more of the following conditions, preferably all of the following conditions, to be suitable for use in a topical composition:
  • the polymers of the present invention are capable of releasing salicylic acid compoundand/or other active agent (for example, through degradation and/or ester cleavage), and the released salicylic acid compound and/or other active agent is topically active.
  • the polymer releases salicylic acid and/or other active agent compound in a topically effective amount: that is, in an amount sufficient to treat skin, for example in an amount sufficient to treat or prevent skin conditions such as, for example, acne and/or to improve skin properties such as, for example, reducing the appearance of fine lines or wrinkles.
  • composition of the invention can further optionally comprise any additive usually used in the field under consideration.
  • oils, water, pigments, solvents such as alcohols, polyols, film forming agents, dispersants, antioxidants, vitamins, sunscreens, preserving agents, fragrances, fillers, neutralizing agents, surfactants, antiperspirants, hydrophilic polymers, and mixtures thereof can be added.
  • solvents such as alcohols, polyols, film forming agents, dispersants, antioxidants, vitamins, sunscreens, preserving agents, fragrances, fillers, neutralizing agents, surfactants, antiperspirants, hydrophilic polymers, and mixtures thereof
  • suitable additional components can be found in the other references which have been incorporated by reference in this application. Still further examples of such additional ingredients may be found in the International Cosmetic Ingredient Dictionary and Handbook (9 th ed. 2002).
  • emulsions without emulsifying surfactants, or containing less than 0.5% thereof, with respect to the total weight of the composition, using appropriate compounds, for example polymers having emulsifying properties, such as the polymers sold under the names Carbopol 1342 and Pemulen by the company Noveon; or optionally crosslinked and/or neutralized polymers and copolymers of 2-acrylamido-2-methylpropanesulphonic acid, such as the poly-(2-acrylamido-2-methylpropanesulphonic acid) sold by the company Clariant under the name "Hostacerin AMPS" (INCI name: ammonium polyacryldimethyltauramide) or such as the emulsion polymer sold under the name Sepigel 305 by the company Seppic (INCI name: polyacrylamide/C13-C14 isoparaffin/laureth-7); particles of ionic or nonionic polymers, more particularly particles of anionic polymer, such as in particular isophthalic acid
  • additives may be present in the composition in a proportion from 0% to 99% (such as from 0.01 % to 90%) relative to the total weight of the composition and further such as from 0.1 % to 50% (if present), including all ranges and subranges therebetween.
  • composition of the invention should be cosmetically or dermatologically acceptable, i.e., it should contain a non-toxic physiologically acceptable medium and should be able to be applied to the eyelashes of human beings.
  • a topical composition comprises micelles in which at least one polymer of the present invention is encapsulated. Encapsulating active agents in micelles is well-known in the art. Preferably, such micelles comprise at least one polymer of the present invention but do not contain any solvent.
  • topical compositions comprising at least one polymer of the present invention may be combined with other compositions or actions upon application to skin.
  • kits comprising a topical composition comprising at least one polymer of the present invention and a second composition for combination with the topical composition can be provided.
  • a kit comprising a first composition comprising, consisting essentially of, or consisting of at least one polymer of the present invention and a second composition comprising at least one solvent in which the polymer(s) is (are) solubilized can be provided.
  • the first composition can be combined with the second composition to solubilize the polymer(s), and such solubilization results in release of salicylic acid compound(s) and/or other active agent(s) of the polymer(s).
  • the first composition may further comprise a solvent such that the polymer(s) is (are) solubilized, but release of salicylic acid compound(s) and/or other active agent(s) does not occur.
  • the second composition comprises a compound which triggers release of the salicylic acid compound(s) and/or other active agent(s) from the polymer(s).
  • methods for treating or preventing skin-related conditions which can be treated or prevented using a salicylic acid compound comprising topically applying to the skin of a human a composition comprising at least one polymer comprising at least one salicylic acid compound and at least one dicarboxylic acid compound in an amount sufficient to treat or prevent the condition are provided.
  • methods for treating or preventing skin-related conditions which can be treated or prevented using a salicylic acid compound and/or other active agent comprising topically applying to the skin of a human a composition comprising at least one polymer comprising at least one salicylic acid compound, at least one other active agent, and at least one dicarboxylic acid compound in an amount sufficient to treat or prevent the condition are provided.
  • methods for improving skin properties or characteristics which can be improved using a salicylic acid compound comprising topically applying to the skin of a human a composition comprising at least one polymer comprising at least one salicylic acid compound and at least one dicarboxylic acid compound in an amount sufficient to improve the property or characteristic are provided.
  • methods for improving skin properties or characteristics which can be improved using a salicylic acid compound and/or other active agent comprising topically applying to the skin of a human a composition comprising at least one polymer comprising at least one salicylic acid compound, at least one other active agent, and at least one dicarboxylic acid compound in an amount sufficient to improve the property or characteristic are provided.
  • methods for providing extended treatment to skin comprising topically applying to skin a composition comprising at least one polymer comprising at least one salicylic acid compound, at least one other active agent, and at least one dicarboxylic acid compound in an amount sufficient to treat the skin with the salicylic acid compound and/or other active agent over a period of time are provided.
  • extended treatment occurs for a period between 4 hours and 5 days per application of the composition, more preferably 6 hours and 3 days, more preferably between 8 hours and 2 days.
  • methods of treating or preventing wrinkles or fine lines comprising applying a composition comprising at least one polymer comprising at least one salicylic acid compound and at least one dicarboxyic acid compound in an amount sufficient to prevent or treat wrinkles or fine lines are provided.
  • methods of treating or preventing wrinkles or fine lines comprising applying a composition comprising at least one polymer comprising at least one salicylic acid compound, at least one other active agent, and at least one dicarboxyic acid compound in an amount sufficient to prevent or treat wrinkles or fine lines are provided.
  • methods of rejuvenating skin comprising applying a composition comprising at least one polymer comprising at least one salicylic acid compound and at least one dicarboxylic acid compound in an amount sufficient to rejuvenate skin are provided.
  • methods of rejuvenating skin comprising applying a composition comprising at least one polymer comprising at least one salicylic acid compound, at least one other active agent, and at least one dicarboxylic acid compound in an amount sufficient to rejuvenate skin are provided.
  • methods of improving skin tone comprising applying a composition comprising at least one polymer comprising at least one salicylic acid compound and at least one dicarboxylic acid compound in an amount sufficient to improve skin pigmentation homogenization are provided.
  • methods of lightening skin comprising applying a composition comprising at least one polymer comprising at least one salicylic acid compound, at least one other active agent, and at least one dicarboxylic acid compound in an amount sufficient to lighten skin are provided.
  • methods of peeling skin comprising applying a composition comprising at least one polymer comprising at least one salicylic acid compound, at least one other active agent, and at least one dicarboxylic acid compound in an amount sufficient to peel skin are provided.
  • a peel can be a superficial, medium or deep peel.
  • methods of treating acne comprising applying a composition comprising at least one polymer comprising at least one salicylic acid compound, at least one other active agent, and at least one dicarboxylic acid compound in an amount sufficient to treat acne are provided.
  • methods of reducing or minimizing perspiration and/or odor comprising applying to skin (for example, armpit(s)) a composition comprising at least one polymer comprising salicylic acid compound and at least one dicarboxylic acid compound in an amount sufficient to reduce or minimize perspiration and/or odor are provided.
  • methods of reducing or minimizing perspiration and/or odor comprising applying to skin (for example, armpit(s)) a composition comprising at least one polymer comprising salicylic acid compound, at least one other active agent, and at least one dicarboxylic acid compound in an amount sufficient to reduce or minimize perspiration and/or odor are provided.
  • compositions of the present invention comprising at least one polymer comprising at least one salicylic acid compound and/or at least one other active agent, and at least one dicarboxylic acid compound are applied topically to the desired area of the skin of a person in need of the desired treatment or prevention in an amount sufficient to achieve the desired result.
  • the compositions may be applied to the desired area as needed, preferably once or twice daily, more preferably once daily or even once every two days.
  • methods of stabilizing a salicylic acid compound and/or other active agent in a topical composition comprising incorporating the salicylic acid compound and other active agent into a polymer comprising at least one dicarboxylic acid compound are provided.
  • all numbers expressing quantities of ingredients, reaction conditions, and so forth used in the specification and claims are to be understood as being modified in all instances by the term "about.” Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and attached claims are approximations that may vary depending upon the desired properties sought to be obtained by the present invention.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des compositions destinées à une application topique sur la peau et comprenant au moins un polymère comprenant au moins un composé d'acide salicylique et au moins un composé d'acide dicarboxylique.
PCT/US2010/038842 2009-06-16 2010-06-16 Compositions topiques contenant un polymère pour libérer au moins un composé d'acide salicylique WO2010148101A2 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US18745309P 2009-06-16 2009-06-16
US18749909P 2009-06-16 2009-06-16
US61/187,499 2009-06-16
US61/187,453 2009-06-16
US23989809P 2009-09-04 2009-09-04
US61/239,898 2009-09-04

Publications (2)

Publication Number Publication Date
WO2010148101A2 true WO2010148101A2 (fr) 2010-12-23
WO2010148101A3 WO2010148101A3 (fr) 2011-05-05

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/038842 WO2010148101A2 (fr) 2009-06-16 2010-06-16 Compositions topiques contenant un polymère pour libérer au moins un composé d'acide salicylique

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030035787A1 (en) * 1999-10-21 2003-02-20 Rutgers, The State University Of New Jersey Polyanhydrides with biologically active degradation products
US20060251690A1 (en) * 2005-04-01 2006-11-09 Zymes, Llc Skin enrichment using CoQ10 as the delivery system
US20080234235A1 (en) * 2001-11-23 2008-09-25 Uhrich Kathryn E Synthesis of Polyanhydrides

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2774287B1 (fr) * 1998-01-30 2000-05-12 Oreal Patch nettoyant, revelateur de l'etat de la peau

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030035787A1 (en) * 1999-10-21 2003-02-20 Rutgers, The State University Of New Jersey Polyanhydrides with biologically active degradation products
US20080234235A1 (en) * 2001-11-23 2008-09-25 Uhrich Kathryn E Synthesis of Polyanhydrides
US20060251690A1 (en) * 2005-04-01 2006-11-09 Zymes, Llc Skin enrichment using CoQ10 as the delivery system

Also Published As

Publication number Publication date
WO2010148101A3 (fr) 2011-05-05

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