WO2011070171A1 - Derivatives of novel peroxides, method of preparation thereof and use thereof in human medicine as well as in cosmetics for the treatment or prevention of acne - Google Patents

Derivatives of novel peroxides, method of preparation thereof and use thereof in human medicine as well as in cosmetics for the treatment or prevention of acne Download PDF

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Publication number
WO2011070171A1
WO2011070171A1 PCT/EP2010/069421 EP2010069421W WO2011070171A1 WO 2011070171 A1 WO2011070171 A1 WO 2011070171A1 EP 2010069421 W EP2010069421 W EP 2010069421W WO 2011070171 A1 WO2011070171 A1 WO 2011070171A1
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WIPO (PCT)
Prior art keywords
benzoyl peroxide
benzoyl
peroxide example
bis
methoxy
Prior art date
Application number
PCT/EP2010/069421
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English (en)
French (fr)
Inventor
Claire Bouix-Peter
Jean-Claude Pascal
Nicolas Rodeville
Original Assignee
Galderma Research & Development
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
Priority to PL10790768T priority Critical patent/PL2509569T3/pl
Priority to CN201080063560.1A priority patent/CN102740826B/zh
Priority to ES10790768.5T priority patent/ES2449471T3/es
Priority to CA2782927A priority patent/CA2782927C/en
Priority to BR112012013396A priority patent/BR112012013396A2/pt
Priority to AU2010329841A priority patent/AU2010329841B2/en
Priority to DK10790768.5T priority patent/DK2509569T3/en
Priority to JP2012542569A priority patent/JP5613776B2/ja
Application filed by Galderma Research & Development filed Critical Galderma Research & Development
Priority to RS20140087A priority patent/RS53229B/en
Priority to US13/514,262 priority patent/US8729312B2/en
Priority to RU2012128866/04A priority patent/RU2552110C2/ru
Priority to EP10790768.5A priority patent/EP2509569B1/en
Priority to MX2012006213A priority patent/MX2012006213A/es
Priority to SI201030543T priority patent/SI2509569T1/sl
Publication of WO2011070171A1 publication Critical patent/WO2011070171A1/en
Priority to HRP20140190AT priority patent/HRP20140190T1/hr
Priority to SM201400049T priority patent/SMT201400049B/xx

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00—Peroxy compounds
    • C07C409/32—Peroxy compounds the —O—O— group being bound between two >C=O groups
    • C07C409/34—Peroxy compounds the —O—O— group being bound between two >C=O groups both belonging to carboxylic acids
    • 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
    • A61K8/38—Percompounds, e.g. peracids
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00—Peroxy compounds
    • C07C409/40—Peroxy compounds containing nitrogen atoms

Definitions

  • Common acne is a chronic disorder of the pilosebaceous follicles (pilosebaceous apparatus) that is characterized by comedones (blackheads) , papules, pustules, cysts, nodules and often scars which appear on the most visible areas of the skin, notably on the face, chest, back and sometimes the neck and upper arms.
  • the pilosebaceous apparatus is largely under the control of endogenous hormones (mainly androgens) which are present at unusually high concentrations in the blood during adolescence and puberty and result in excessive production of sebum. This situation may worsen as a result of a concomitant increase in the degree of keratinization of the horny layer of the skin (stratum corneum) . As the horny cells proliferate, they can form an occlusive plug or comedo which, combined with increased production of sebum, constitutes an ideal medium for proliferation of the strains of bacteria that reside on and in the skin, such as the Gram-positive anaerobic bacterium Propionibacterium acnes .
  • endogenous hormones mainly androgens
  • the exposed follicles can darken in colour through deposition of pigment derived from damaged cells of the deep layer of the skin.
  • Acne is a condition with several stages, and in its most serious form it leads to hospitalization of the patient and proves very troublesome with long-term presence of scarring of the skin.
  • treatment of acne employs topical formulations in the form of creams, gels, emulsions or lotions containing selected agents.
  • agents comprise, for example, hormones or agonists and antagonists of hormones (EPA1 0 563 813 and US 5 439 923), antimicrobial agents (US 4 446 145, GB 2 088 717, GB 2 090 135, GB 1 054 124, US 5 409 917), salicylic acid (US 4 514 385, US 4 355 028, EPA1 0 052 705, FR-A 2 581 542 and FR-A 2 607 498) .
  • hormones or agonists and antagonists of hormones EPA1 0 563 813 and US 5 439 923
  • antimicrobial agents US 4 446 145, GB 2 088 717, GB 2 090 135, GB 1 054 124, US 5 409 917
  • salicylic acid US 4 514 385, US 4 355 028, EPA1 0 052 705, FR-A 2 581 542 and FR-A 2 607 498) .
  • the problems associated with topical treatment of acne with creams, gels, emulsions or lotions comprise lack of precision in application and absence of precise control of the dose at the intended site.
  • Application of a cream, gel, emulsion or lotion involves exposing an area considerably larger than that covered by the lesion, so normal healthy skin is exposed to the anti ⁇ acne formulation.
  • Salicylic acid for example, is irritant to normal skin in the case of prolonged exposure, notably at high concentrations.
  • isotretinoin which is a derivative of vitamin A, has associated risks of teratogenicity and it can constitute a risk for women of child-bearing age .
  • antibiotics suitable for the treatment of acne may be accompanied by the development of side effects such as abdominal cramps, glossophytia, cough, diarrhoea, fatigue, mouth irritation and other undesirable symptoms.
  • the present invention proposes to provide novel derivatives of peroxides having improved anti-acne efficacy resulting for example from better bactericidal activity than the compounds of the prior art such as benzoyl peroxide, while controlling the potential sensitizing effect, the irritant effect, and not adding a component with anti-inflammatory activity.
  • -Z represents an oxygen or the following sequence:
  • -Y represents a hydro en or the following sequence:
  • -V represents an oxygen or the following sequence:
  • R3 and R6 represent, identically or independently, a hydrogen or a C 1 -4 alkyl
  • R4 represent, identically or independently, a hydrogen or a C 1 -4 alkyl
  • -R2 and R5 represent, identically or independently, a Ci- 1 0 alkyl or a Ci- 1 0 alkoxy
  • the preferred compounds corresponding to general formula (I) are those having the following characteristics: -Z represents an oxygen or the following sequence:
  • -Y represents a hydrogen or the following sequence:
  • -V represents an oxygen or the following sequence:
  • -R3 and R6 represent, identically or independently, a hydrogen, a methyl or an ethyl
  • -Rl and R4 represent, identically or independently, a hydrogen or a methyl
  • -R2 and R5 represent, identically or independently, a Ci-4 alkyl or a C 1 -4 alkoxy
  • C 1 -4 alkyl denotes a saturated, linear or branched hydrocarbon chain comprising 1 to 4 carbon atoms.
  • Ci-io alkyl denotes a saturated, linear or branched hydrocarbon chain comprising 1 to 10 carbon atoms.
  • C1-4 alkoxy denotes an oxygen atom substituted with a C1-4 alkyl.
  • Ci-10 alkoxy denotes an oxygen atom substituted with a Ci-10 alkyl .
  • Example 2 (2-acetoxymethoxy-benzoyl) benzoyl peroxide
  • Example 3 bis (2-propionyloxymethoxy) -benzoyl peroxide
  • Example 4 (2-propionyloxymethoxy-benzoyl) benzoyl peroxide
  • Example 5 bis (2-butyryloxymethoxy) -benzoyl peroxide
  • Example 6 (2-butyryloxymethoxy-benzoyl) benzoyl peroxide
  • Example 7 bis (2-pentanoyloxymethoxy) -benzoyl peroxide
  • Example 8 (2-pentanoyloxymethoxy-benzoyl) benzoyl peroxide
  • Example 9 bis (2-isobutyryloxymethoxy) -benzoyl peroxide
  • Example 10 (2-isobutyryloxymethoxy-benzoyl) benzoyl peroxide
  • Example 13 bis [2- ( 1-acetoxy-ethoxy) ] -benzoyl peroxide
  • Example 14 [2- (1-acetoxy-ethoxy) -benzoyl] benzoyl peroxide
  • Example 17 bis (2-propoxycarbonyloxymethoxy) -benzoyl peroxide
  • Example 25 bis [2- (ethoxycarbonylamino-methoxy) ] - benzoyl peroxide
  • Example 27 bis (2- [ (ethoxycarbonyl-ethyl-amino) - methoxy] ) -benzoyl peroxide
  • Example 29 bis (2- [ (ethoxycarbonyl-methyl-amino) - methoxy] ) -benzoyl peroxide
  • Example 31 bis (2- [ (methyl-propoxycarbonyl-amino) - methoxy] ) -benzoyl peroxide
  • Example 33 bis (2- [ (butoxycarbonyl-methyl-amino) - methoxy] ) -benzoyl peroxide
  • Example 34 (2- [ (butoxycarbonyl-methyl-amino) -methoxy] - benzoyl) benzoyl peroxide
  • Example 35 bis (2- [ (isopropoxycarbonyl-methyl-amino) - methoxy] ) -benzoyl peroxide
  • Example 37 bis (2- [ (tert-butoxycarbonyl-methyl-amino) - methoxy] ) -benzoyl peroxide
  • the acid chlorides general formula (III) are prepared from carboxylic (II), by methods selected from those known by a person skilled in the art (EP 121 968 2) . They comprise the use of thionyl chloride and pyridine in a solvent such as toluene or dichloromethane for example.
  • the compounds of general formula (V) can be prepared by coupling between the acyl chlorides of formula (III) and the per-acid of formula (IV), using pyridine as base in a mixture of solvents such as dichloromethane and chloroform (Evanochko,
  • the peroxides of general formula (V) are prepared by coupling between the carboxylic acids of formula (II) and the per-acid of formula (IV), for example using ⁇ , ⁇ '- dicyclohexylcarbodiimide as coupling agent for example in a mixture of solvents such as diethyl ether and dichloromethane ( Spantulescu, M.D.; Jain, R.P.; Derksen, D.J.; Vederas, J.C.; Org. Lett. 2003, 5(16), 2963-2965) .
  • the carboxylic acids of general formula (II) are prepared according to the methods described in scheme 7.
  • the per-acid of general formula (IV) is prepared according to the method described in scheme 8 from benzoyl peroxide.
  • the acid chlorides of general formula (VII) are prepared from carboxylic acid (VI), by methods selected from those known by a person skilled in the art (EP 121 968 2) . They comprise the use of thionyl chloride and pyridine in a solvent such as toluene or dichloromethane for example.
  • the compounds of general formula (VIII) can be prepared by coupling between two acyl chlorides of formula (VII) by methods selected from those known by a person skilled in the art (EP 0 108 821) . They comprise the use of hydrogen peroxide and sodium bicarbonate in a solvent such as tetrahydrofuran for example.
  • the peroxides of general formula (VIII) are prepared by reaction between two carboxylic acids of formula (VI), using for example N, ' -dicyclohexylcarbodiimide and hydrogen peroxide in a mixture of solvents such as diethyl ether and dichloromethane ( Spantulescu, M.D.; Jain, R.P.; Derksen, D.J.; Vederas, J.C.; Org. Lett. 2003, 5(16), 2963-2965) .
  • the acid chlorides of general formula (III) are prepared from carboxylic acid (II), by methods selected from those known by a person skilled in the art (EP 121 968 2) . They comprise the use of thionyl chloride and pyridine in a solvent such as toluene or dichloromethane for example.
  • the compounds of general formula (X) can be prepared by coupling between the acyl chlorides of formula (III) and the per-acid of formula (IX), for example using pyridine as base in a mixture of solvents such as dichloromethane and chloroform.
  • the per-acid of general formula (IX) is prepared according to the method described in scheme 9 from the peroxide defined in formula (VIII) .
  • the peroxides of general formula (X) are prepared by coupling between the carboxylic acids of formula (II) and the per-acid of formula (IX), for example using ⁇ , ⁇ '- dicyclohexylcarbodiimide as coupling agent in a mixture of solvents such as diethyl ether and dichloromethane.
  • the carboxylic acids of general formula (II) are available commercially or are prepared according to the method described in scheme 7.
  • the per-acid of general formula (IX) is prepared according to the method described in scheme 9 from the peroxide defined in formula (VIII) .
  • the carboxylic acids of formula (II) can be prepared according to reaction scheme 7.
  • the carboxylic acids of formula (VI) are prepared according to the same reaction scheme.
  • the aldehydes of formula (XIV) are prepared from salicylaldehyde (XI) by methods selected from those known by a person skilled in the art (Thomas, J.D.; Sloan, K.B.; Tetrahedron Lett. 2007, 48, 109-112) . They comprise the use of a halide of formula (XII) or (XIII) and bases such as triethylamine, pyridine, potassium carbonate in a solvent such as acetone or dichloromethane for example.
  • the carboxylic acids of general formula (II) can be prepared by oxidation of the aldehydes of formula (XIV) with sodium perchlorite, in a mixture of solvents such as water and tert-butanol (Marsini, M.A.; Gowin, K.M.; Pettus, T.R.R.; Org. Lett. 2006, 8 (16) , 3481-3483) .
  • the per-acid of formula (IV) can be prepared according to reaction scheme 8.
  • the per-acid of formula (IV) is prepared from dibenzoyl peroxide (XV) by methods selected from those known by a person skilled in the art (US 3 075 921) . They comprise the use of a peroxide (XV) and sodium in a mixture of solvents such as methanol and chloroform.
  • the per-acids of formulae (IX) can be prepared according to reaction scheme 9.
  • the per-acids of formula (IX) are prepared from the peroxide of formula (VIII) by methods selected from those known by a person skilled in the art (US 3 075 921) . They comprise the use of a peroxide (VIII) and sodium in a mixture of solvents such as methanol and chloroform.
  • the iodides of formula (XII) can be prepared according to reaction scheme 10 or are available commercially .
  • the chlorides of formula (XVIII) are available commercially or are prepared from the acid chloride of formula (XVII) by methods selected from those known by a person skilled in the art (Thomas, J.D.; Sloans, K.B.; Synthesis 2008, 2, 272-278 and Majumdar, S . ; Sloan, K.B.; Bioorg. Med. Chem. 2006, 16, 3590-3594). They comprise the use of a triazene or a trioxane of formula (XVI) in a solvent such as dichloromethane for example.
  • the iodides of formula (XII) are prepared from the chloride of formula (XVIII) by methods selected from those known by a person skilled in the art. They comprise the use of a chloride of formula (XVIII) and sodium iodide in a solvent such as acetone for example.
  • the chlorides of formula (XVIII) are prepared from the acid chloride of formula (XX) by methods selected from those known by a person skilled in the art (Thomas, J.D.; Sloan, K.B.; Tetrahedron Lett. 2007, 48, 109-112) . They comprise the use of an alcohol of formula (XIX) and bases such as triethylamine, pyridine, in a solvent such as dichloromethane for example.
  • the iodides of formula (XII) are prepared from the chloride of formula (XVIII) by methods selected from those known by a person skilled in the art (Thomas, J.D.; Sloan, K.B.; Tetrahedron Lett. 2007, 48, 109-112) . They comprise the use of a chloride of formula (XVIII) and sodium iodide in a solvent such as acetone for example.
  • the aim is to evaluate the anti-bacterial activity of the peroxides by measuring the minimum inhibitory concentration (MIC) .
  • MIC minimum inhibitory concentration
  • the MIC is defined as the lowest concentration of product capable of inhibiting all visible growth.
  • the products are dissolved at 1280 mg/L in a mixture of absolute ethanol/sterile Tween 80/sterile Wilkins Chalgren broth (5/10/85 v/v/v) .
  • the dilution ranges used are an adaptation of the method described by the CLSI for methods of dilution in liquid medium.
  • the range consists of 10 concentrations from 2.5 mg/L to 1280 mg/L at intervals of ratio 2.
  • the suspension of P. acnes is prepared in Wilkins Chalgren broth and calibrated at an optical density of about 0.4 at wavelength of 525 nm. It is then diluted to 1/10 in Wilkins Chalgren broth and then put in the test cupules to obtain a final suspension of about 10 5 - 10 s CFU/mL in each test cupule.
  • the solutions of the test products are distributed on a 96-well microplate and incubated at 36°C ⁇ 2°C under anaerobic atmosphere for a minimum of 72h.
  • the first cupule for which there is no growth visible to the naked eye is regarded as the MIC.
  • the aim is to evaluate the anti ⁇ inflammatory activity of the peroxides by measuring the thickness of mouse ear after TPA topical application.
  • the anti-inflammatory activity is defined as a inhibition percentage of the TAP-induced ear oedema.
  • An oedema was induced by a single topical application of 20 ⁇ 1 of TPA dissolved in acetone at 0.01%.
  • Ear thickness was measured at T6h.
  • Results are expressed in percentages based on the inhibition on the oedema induced by the TPA application .
  • BPO Benzoyl peroxide
  • the aim of this study was to demonstrate the anti- inflammatory effect of New peroxides after a single topical application in the TPA-induced ear oedema mouse model .
  • Ex n°l at 5% appears slightly better than Ex n°2 at 5% and both are superior compared to BPO 5%.

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  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
PCT/EP2010/069421 2009-12-10 2010-12-10 Derivatives of novel peroxides, method of preparation thereof and use thereof in human medicine as well as in cosmetics for the treatment or prevention of acne WO2011070171A1 (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
RS20140087A RS53229B (en) 2009-12-10 2010-12-10 NEW PEROXIDES DERIVATIVES, PROCEDURES FOR THEIR PREPARATION AND THEIR USE IN HUMAN MEDICINES AS IN COSMETICS FOR THE TREATMENT OR PREVENTION OF ACNE
CN201080063560.1A CN102740826B (zh) 2009-12-10 2010-12-10 过氧化物的衍生物、其制备方法及其在人类医学中以及在化妆品中用于治疗或预防痤疮的用途
US13/514,262 US8729312B2 (en) 2009-12-10 2010-12-10 Derivatives of novel peroxides, method of preparation thereof and use thereof in human medicine as well as in cosmetics for the treatment or prevention of acne
BR112012013396A BR112012013396A2 (pt) 2009-12-10 2010-12-10 "compostos, uso de um composto e composição cosmética"
AU2010329841A AU2010329841B2 (en) 2009-12-10 2010-12-10 Derivatives of novel peroxides, method of preparation thereof and use thereof in human medicine as well as in cosmetics for the treatment or prevention of acne
DK10790768.5T DK2509569T3 (en) 2009-12-10 2010-12-10 DERIVATIVES OF ANY UNKNOWN PEROXIDES, PROCEDURES FOR THE PREPARATION OF IT AND ITS USE IN HUMAN MEDICINE AND IN COSMETICS FOR TREATMENT OR PREVENTION OF ACN
JP2012542569A JP5613776B2 (ja) 2009-12-10 2010-12-10 新規過酸化物の誘導体、その調製方法、および、ニキビを治療または予防するためのヒト用医薬品および化粧品における使用
PL10790768T PL2509569T3 (pl) 2009-12-10 2010-12-10 Pochodne nowych nadtlenków, sposób ich wytwarzania oraz zastosowania w medycynie ludzi jak również w kosmetykach do leczenia lub zapobiegania trądzikowi
ES10790768.5T ES2449471T3 (es) 2009-12-10 2010-12-10 Derivados de nuevos peróxidos, método de preparación de los mismos y su uso en medicina humana, así como en cosméticos, para el tratamiento o la prevención del acné
CA2782927A CA2782927C (en) 2009-12-10 2010-12-10 Derivatives of novel peroxides, method of preparation thereof and use thereof in human medicine as well as in cosmetics for the treatment or prevention of acne
RU2012128866/04A RU2552110C2 (ru) 2009-12-10 2010-12-10 Производные новых перекисей, способ их получения и применение в медицине и в косметике для лечения или предотвращения угрей
EP10790768.5A EP2509569B1 (en) 2009-12-10 2010-12-10 Derivatives of novel peroxides, method of preparation thereof and use thereof in human medicine as well as in cosmetics for the treatment or prevention of acne
MX2012006213A MX2012006213A (es) 2009-12-10 2010-12-10 Derivados de peroxido nuevos, metodo de preparacion de los mismos y uso de los mismos en medicina humana asi como en cosmeticos para el tratamiento o prevencion de acne.
SI201030543T SI2509569T1 (sl) 2009-12-10 2010-12-10 Derivati iz novih peroksidov, postopek priprave le-teh in uporaba le-teh v humani medicini kot tudi v kozmetiki za tretiranje ali preprečitev aken
HRP20140190AT HRP20140190T1 (hr) 2009-12-10 2014-03-03 Derivati novih peroksida, postupak njihovog dobivanja, te njihova upotreba u medicini, kao i u kozmetici, u lijeäśenju ili sprjeäśavanju akni
SM201400049T SMT201400049B (it) 2009-12-10 2014-04-11 Derivati di nuovi perossidi, loro metodo di preparazione e loro uso nella medicina umana cosi' come nella cosmesi per il trattamento o la prevenzione dell'acne

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0958847A FR2953833B1 (fr) 2009-12-10 2009-12-10 Derives de nouveaux peroxydes, leur procede de preparation et leur utilisation en medecine humaine ainsi qu'en cosmetique pour le traitement ou la prevention de l'acne
FR0958847 2009-12-10

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WO2011070171A1 true WO2011070171A1 (en) 2011-06-16

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US (1) US8729312B2 (ko)
EP (1) EP2509569B1 (ko)
JP (1) JP5613776B2 (ko)
KR (1) KR101566065B1 (ko)
CN (1) CN102740826B (ko)
AU (1) AU2010329841B2 (ko)
BR (1) BR112012013396A2 (ko)
CA (1) CA2782927C (ko)
CY (1) CY1115204T1 (ko)
DK (1) DK2509569T3 (ko)
ES (1) ES2449471T3 (ko)
FR (1) FR2953833B1 (ko)
HR (1) HRP20140190T1 (ko)
MX (1) MX2012006213A (ko)
PL (1) PL2509569T3 (ko)
PT (1) PT2509569E (ko)
RS (1) RS53229B (ko)
RU (1) RU2552110C2 (ko)
SI (1) SI2509569T1 (ko)
SM (1) SMT201400049B (ko)
WO (1) WO2011070171A1 (ko)

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1054124A (ko) 1964-03-31
US3075921A (en) 1959-02-11 1963-01-29 Procter & Gamble Substituted peroxybenzoic acid bleaching agents
EP0052705A1 (en) 1980-11-24 1982-06-02 Joel E. Bernstein, M.D. Composition for treating acne vulgaris
GB2088717A (en) 1980-12-08 1982-06-16 Rorer Int Overseas A composition for the topical treatment of acne
US4355028A (en) 1978-04-04 1982-10-19 Westwood Pharmaceuticals, Inc. Composition for treating acne vulgaris
US4364940A (en) * 1981-02-23 1982-12-21 Usv Pharmaceutical Corporation Compositions for treating acne
US4446145A (en) 1980-01-24 1984-05-01 Janssen Pharmaceutica N.V. Anti-microbial compositions for the topical treatment of acne vulgaris
US4514385A (en) 1981-10-05 1985-04-30 Alcon Laboratories, Inc. Anti-acne compositions
FR2581542A1 (fr) 1985-05-07 1986-11-14 Oreal Compositions topiques destinees au traitement de la peau a base de derives de l'acide salicylique
FR2607498A1 (fr) 1986-12-01 1988-06-03 Oreal Nouveaux salicylates lipophiles d'ammoniums quaternaires, leur utilisation en cosmetique et en dermopharmacie
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