EP3723748A2 - Association comprenant de l'adapalène, du peroxyde de benzoyle et un agent du groupe des cicatrisants - Google Patents

Association comprenant de l'adapalène, du peroxyde de benzoyle et un agent du groupe des cicatrisants

Info

Publication number
EP3723748A2
EP3723748A2 EP18912818.4A EP18912818A EP3723748A2 EP 3723748 A2 EP3723748 A2 EP 3723748A2 EP 18912818 A EP18912818 A EP 18912818A EP 3723748 A2 EP3723748 A2 EP 3723748A2
Authority
EP
European Patent Office
Prior art keywords
weight
composition according
stable topical
oil
topical composition
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
EP18912818.4A
Other languages
German (de)
English (en)
Other versions
EP3723748A4 (fr
Inventor
Ali TÜRKYILMAZ
Sibel ZENGINER
Seval Ataman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanovel Ilac Sanayi ve Ticaret AS
Original Assignee
Sanovel Ilac Sanayi ve Ticaret AS
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 Sanovel Ilac Sanayi ve Ticaret AS filed Critical Sanovel Ilac Sanayi ve Ticaret AS
Publication of EP3723748A2 publication Critical patent/EP3723748A2/fr
Publication of EP3723748A4 publication Critical patent/EP3723748A4/fr
Pending legal-status Critical Current

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
    • 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
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/113—Multiple emulsions, e.g. oil-in-water-in-oil

Definitions

  • the present invention relates to stable topical compositions comprising benzoyl peroxide, adapalene free base or pharmaceutically acceptable salts thereof and an active agent from the cicatrizant group wherein the composition comprises two or more phases and pharmaceutically acceptable excipients.
  • Acne is a disease of the skin in which the pilosebaceous structures of the skin become inflamed, leading to the formation of comedones, pustules, and nodules. It is generally believed that acne arises when hyperkeratosis of the pilosebaceous structure wholly or partially blocks the opening of the structure, resulting in comedones filled with sebum, keratin, and Propionibacterium acnes.
  • Propionibacterium acnes is the name of the bacteria that live on the skin and contributes to the infection of pimples. It is believed that metabolic by-products and waste from P. acnes within the pilosebaceous structures cause or contribute to the inflammation of acne lesions.
  • Oral drugs include antibiotics like tetracycline, minocycline, doxycycline, and erythromycin.
  • Topical agents for the treatment of acne include retinoids such as tretinoin and adapalene; sulfur; resorcinol; salicylic acid; benzoyl peroxide; and antibiotics such as erythromycin, clindamycin, or tetracycline.
  • adapalene is 6- [3- (1 -Adamantyl) -4-methoxyphenyl] -2-naphthoic acid, having a formula of C 28 H 28 O 3 , a molecular weight of 412.529 g/mol and a chemical structural formula shown below (I):
  • Adapalene is a naphthoic acid derivative with retinoid and anti-inflammatory properties. This molecule was the subject of development for the topical treatment of common acne and of dermatoses sensitive to retinoids.
  • Adapalene is sold under the brand name Differin ® at a weight concentration of 0.1%, in the form of an "alcoholic lotion” solution, an aqueous gel and a cream. These compositions are intended for treating acne.
  • Patent application FR2837101 describes adapalene compositions at a weight concentration of 0.3%, for treating acne.
  • Benzoyl peroxide has a formula of C I4 H 10 O 4 , a molecular weight of 242.23 g/mol and a chemical structural formula shown below (II):
  • Benzoyl peroxide has been widely used for the treatment of acne.
  • Gel or cream containing benzoyl peroxide is usually rubbed into the pores over the affected region.
  • benzoyl peroxide also prevents new lesions by killing P. acnes.
  • Benzoyl peroxide has the advantage of being a strong oxidizer and thus does not appear to generate bacterial resistance.
  • Patent application WO 03/055472 moreover describes stable pharmaceutical compositions comprising adapalene and benzoyl peroxide.
  • adapalene and benzoyl peroxide there is a need in the prior art for an alternative combination of adapalene and benzoyl peroxide. Although there are many examples of combinations with adapalene and benzoyl peroxide, none of them comprises an agent from cicatrizant group. In this present invention, the selected agent from the cicatrizant group is used to provide rapid and effective treatment.
  • the main object of the present invention is to provide improved compositions which are less irritating, stable, rapid and have effective treatment.
  • Another object of the present invention is to provide rapid penetration of drug substances and a sufficiently long storage life.
  • Another object of the present invention relates to an easily applicable product, eliminating all problems and bringing additional advantages to the relevant prior art.
  • adapalene refers to not only adapalene, but also its other pharmaceutically acceptable salt, pharmaceutically acceptable solvates, pharmaceutically acceptable hydrates or pharmaceutically acceptable polymorphs thereof.
  • cicatrizant is an active ingredient that promotes healing through accelerating the scar tissue regeneration.
  • gelling agent is synonymous with viscosity agent, solidifier, or thickening agent, and refers to an agent that increases the viscosity of the formulation by forming a polymeric structure.
  • Acne can present as noninflammatory lesions, inflammatory lesions, or a mixture of both, affecting mostly the face, the back and chest. Acne scars are caused by inflammation within the dermal layer but scarring may occur with any form of acne.
  • One of the treatments is antibiotics which are frequently applied to the skin or taken orally to treat acne.
  • the use of topical benzoyl peroxide and antibiotics together has been shown to be more effective than antibiotics alone, this is a general information.
  • the combination with an agent from the cicatrizant group is novel and more effective treatment for acne and also the combination provides treatment for acne scars.
  • the stable topical composition comprises benzoyl peroxide, adapalene free base or pharmaceutically acceptable salts of thereof and an active agent selected from cicatrizant.
  • the amount of benzoyl peroxide is between 0.05% and 20.0%.
  • the amount of adapalene free base or pharmaceutically acceptable salts is between 0.001% and 20.0%.
  • Suitable cicatrizant is selected from the group comprising sodium hyaluronate, enoxolone, hyaluronic acid, calcium pantothenate, pantothenic acid, tetrachloro decaoxide, kadexomer iodide, dextranomer, dexpanthenol.
  • the cicatrizant is sodium hyaluronate.
  • Sodium hyaluronate is the salt form of hyaluronic acid, has distinctive viscoelastic and hygroscopic properties and plays many important roles in the human body. It is a naturally occurring lubricant and is made up of biocompatible polysaccharide. Because of its excellent water-retaining properties, it is used in ophthalmic products.
  • the amount of sodium hyaluronate is between 0.001 and 20.0%, preferably the amount of sodium hyaluronate is between 0.001 and 10.0%.
  • composition is for use in the topical treatment of acne vulgaris.
  • the stable topical composition comprises oil phase, water phase or mixtures thereof.
  • the composition is preferably in the form of oil phase - water phase (oil-water, O/W) or water phase in oil phase in water phase (water-in-oil-in-water) (W/O/W) or oil phase in water phase in oil phase (oil-in-water-in-oil) (O/W/O) emulsions.
  • sodium hyaluronate is in the oil phase or water phase or in both.
  • adapalene is in the oil phase.
  • sodium hyaluronate may be in the same oil phase with adapalene or sodium hyaluronate may be in the separate oil phase with adapalene.
  • Benzoyl peroxide is an unstable chemical compound. Degradation of benzoyl peroxide results in formation of benzoic acid impurity that affects the stability of not only excipients used but also other active substances. So, we have found an easy way to have less side effects by using separate phases.
  • benzoyl peroxide is in the water phase in order that benzoyl peroxide is more stable in water.
  • the weight ratio of the oil phase to the water phase is between 0.2 - 2.0, 0.2 - 1.5 or 0.2 -1.0.
  • the amount of the water phase to total composition may be between 20.0% and 80.0%. According to an embodiment of the present invention, the amount of the water phase to total composition may be between 20.0% and 28.0%, 28.0% and 30.0%, 30.0% and 40.0%, 40.0% and 55.0%, 55.0% and 62.0%, 62.0% and 69.0%, 69.0% and 75.0%, 75.0% and 80.0%.
  • the amount of the oil phase to total composition may be between 20.0% and 80.0%.
  • the amount of the oil phase to total composition may be between 20.0% and 31.0%, 31.0% and 38.0%, 38.0% and 45.0%, 45.0% and 55.0%, 55.0% and 62.0%, 62.0% and 72.0%, 72.0% and 80.0%.
  • the stable topical composition comprises pharmaceutically acceptable excipients which are selected from the group comprising gelling agents, oil phase agents, humectants, solvents, co-solvents, preservatives, antioxidants, surfactants, pH-adjusting agents, perfumes or mixtures thereof.
  • Suitable gelling agents are selected from the group comprising carbomer, liquid paraffin, polyacrylamide, cellulosic polymers such as hydroxypropyl cellulose, hydroxyethyl cellulose, methyl cellulose, and hydroxypropylmethyl cellulose, natural and synthetic gums such as guar gum, hydroxypropyl guar gum, xanthan gum, acacia, and tragacanth, modified starch, acrylic acid/ethyl acrylate copolymers, polymethacrylate copolymers, maleic anhydride-alkyl methylvinylethers and copolymers, oleogels, trihydroxystearin, aluminum magnesium hydroxy stearate, poloxamer, polyvinyl alcohol, polyvinyl pyrrolidone, methyl hydroxybenzoate, ethyl hydroxybenzoate, propyl hydroxybenzoate, butyl hydroxybenzoate or mixtures thereof.
  • the gelling agents are between 0.01 % and 8.0% by weight of the total composition.
  • preferably carbomer more preferably carbomer 940 is used as gelling agent, because it is highly efficient thickener and it is ideal for formulating clear aqueous and gel. Its benefits include short flow properties, high viscosity, high suspending ability, and high clarity.
  • Suitable oil phase agents are selected from the group comprising soft paraffin, liquid paraffin, stearyl alcohol, ethyl oleate, almond oil, palm oil, sesame oil, oil sunflower, lanolin, squalene, mink oil, cetearyl isononanoate, diisopropyl adipate, isopropyl palmitate, caprylic/capric triglyceride, an oil volatile or non-volatile silicone or mixtures thereof.
  • the oil phase agent is soft paraffin which is between 12.00% and 54.0% by weight of the total composition.
  • a humectant is a hygroscopic substance used to keep things moist.
  • a humectant attracts and retains the moisture in the air nearby via absorption, drawing the water vapor into or beneath the organism/object's surface.
  • Humectants can be used in topical dosage forms to increase the solubility of a chemical compound's active ingredients, increasing the active ingredients' ability to penetrate skin or its activity time.
  • Suitable humectants are selected from the group comprising propylene glycol, glycerin, butylene glycol, urea, tremella extract, sorbitol, dicyanamide, sodium lactate or mixtures thereof.
  • the humectants are between 0.3% and 10.0% by weight of the total composition.
  • Suitable solvents or co-solvents are selected from the group comprising water, propylene glycol, glycerin, ethanol, polyethylene glycol or mixtures thereof.
  • the solvents or co-solvents are between 26.0% and 60.0% by weight of the total composition.
  • solvents or co solvents are between 35.0% and 57.0% by weight of the total composition.
  • benzoyl peroxide is more stable in water and propylene glycol when it is in dispersed form.
  • benzoyl peroxide in water phase is formulated with propylene glycol in dispersed form.
  • Suitable preservatives are selected from the group comprising citric acid, methyl, ethyl, propyl, and butyl esters of hydroxy benzoic acid, benzoic acid, boric acid, chlorhexidine, benzalkonium chloride, 2-phenoxyethanol, cetrimide, potassium sorbate, thiomersal or mixtures thereof.
  • Suitable antioxidants are selected from the group comprising ascorbyl palmitate, tocopherol, citric acid, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), sodium metabisulfite, ascorbic acid, thiourea, acetylcysteine, dithiothreitol, cysteine hydrochloride, propyl gallate, vitamin E polyethylene glycol succinate, malic acid, sodium sulfite, rutoside, biotin, Pyridoxine, coniferyl alcohol, oxidized glutathione, pyrocatechine, butylparaben, propylparaben, dry green tea extract, resveratrol, quercetin, ubiquinone, pyridoxine, acetyl pantothenate, beta-ionol, 8-hydroxyquinoline, hydroquinone, creatinine, naphthoquinone, turmeric extract (curcumin) or super
  • the antioxidant is ascorbyl palmitate, tocopherol and citric acid or mixtures thereof.
  • the antioxidants are used in the composition to retard oxidation and decomposition of the active ingredients and other substances, thus providing the composition with long-term stability.
  • a surfactant may also be included in the formulation of the present invention to ensure homogeneous dispersion of hydrophilic and hydrophobic phases in the composition.
  • Suitable surfactants are selected from the group comprising propylene glycol, glyceryl oleate, tocopherol, ascorbyl palmitate, citric acid, polyethoxylated fatty acid esters, polyoxyethylene sorbitan esters, polyoxyethylene hydrogenated castor oil, sorbitan esters, sodium lauryl sulphate, docusate sodium, nonoxynol or mixtures thereof.
  • the surfactants are propylene glycol, glyceryl oleate, tocopherol, ascorbyl palmitate, citric acid.
  • surfactants are between 0.01% and 10.0% by weight of the total composition.
  • the stable topical composition comprises, A water phase comprising benzoyl peroxide dispersed in propylene glycol
  • An oil phase comprising adapalene free base or pharmaceutically acceptable salts of adapalene and surfactants which are propylene glycol, glyceryl oleate, tocopherol, ascorbyl palmitate, citric acid. So, this formulation is to provide long-term stability and to prevent degradation of the active agents.
  • the stable topical composition of the present invention may also comprise one or more pH- adjusting agents.
  • Suitable pH-adjusting agents are selected from the group comprising pharmaceutically acceptable organic or inorganic acids or bases, for example, sodium hydroxide, tromethamine, hydrochloric acid or mixtures thereof.
  • the composition of the present invention has a pH of about 4.0 to about 6.0.
  • Suitable perfumes are selected from the group comprising lavender oil, rose oil, lemon oil, and almond oil.
  • the stable topical composition in the present invention is gel, solution, foam, cream, pomade, lotion or spray. More particularly, it is in the form of a gel.
  • the stable topical composition in the present invention has a viscosity in a range of between 5000 cP and 40000 cP at room temperature (20°) and preferably between 8000 cP and 25000 cP.
  • the viscosity of the final composition is arranged to provide a desired topical composition consistency. The composition should be pleased by the patient.
  • the viscosity is measured by using RVDV-II or LVDV-II [GR1 ] Brookfield Digital Viscometers in the conditions of room temperature and 20 rpm. Time of stabilization is 30 seconds.
  • the stable topical composition comprises;
  • the stable topical composition comprises;
  • the stable topical composition comprises;
  • the process for preparation of the stable topical composition comprises the following steps:
  • step(c) Adding glycerin to step(c) mixture and then mixing and homogenizing
  • step(d) mixture Adding step(d) mixture to step(b) mixture and then adjusting pH value 5.0-6.0
  • Oil phase is added to water phase and mixed until homogenious.
  • homogenizer is used at each step of the process.
  • the process for preparation of the stable topical composition comprises the following steps: • Water phase
  • step(c) Adding glycerin to step(c) mixture and then mixing and homogenizing
  • step(d) mixture Adding step(d) mixture to step(b) mixture and then adjusting pH value 5.0-6.0
  • Oil phase I is added to water phase and mixed until obtaining homogeneous“oil in water” emulsion.
  • homogenizer is used at each step of the process.
  • the process for preparation of the stable topical composition comprises the following steps:
  • step(c) Adding glycerin to step(c) mixture and then mixing and homogenizing
  • step(b) Adding the mixture to step(b) mixture and then adjusting pH value 5.0-6.0
  • step (f) Mixing step (f) mixture and step (g) mixture until obtaining homogenous mixture.
  • step (e) Mixing the mixture with step (e) mixture until obtaining homogenous mixture.
  • step (e) Adding the mixture to step (e) mixture and mixed until homogenious.
  • Water phase I and water phase II and oil phase is mixed homogeneously so as to obtain W/O/W emulsion.
  • homogenizer is used at each step of the process.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Birds (AREA)
  • Dispersion Chemistry (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La présente invention concerne des compositions topiques stables comprenant du peroxyde de benzoyle, une base libre d'adapalène ou des sels pharmaceutiquement acceptables de celle-ci et un agent actif choisi dans le groupe des cicatrisants, cette composition comprenant deux phases ou plus et des excipients pharmaceutiquement acceptables.
EP18912818.4A 2017-12-15 2018-12-14 Association comprenant de l'adapalène, du peroxyde de benzoyle et un agent du groupe des cicatrisants Pending EP3723748A4 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR2017/20497A TR201720497A2 (tr) 2017-12-15 2017-12-15 Adapalen, benzoi̇l peroksi̇t ve si̇katri̇zan grubundan bi̇r ajan i̇çeren kombi̇nasyon
PCT/TR2018/050809 WO2019190435A2 (fr) 2017-12-15 2018-12-14 Association comprenant de l'adapalène, du peroxyde de benzoyle et un agent du groupe des cicatrisants

Publications (2)

Publication Number Publication Date
EP3723748A2 true EP3723748A2 (fr) 2020-10-21
EP3723748A4 EP3723748A4 (fr) 2021-07-21

Family

ID=67900496

Family Applications (1)

Application Number Title Priority Date Filing Date
EP18912818.4A Pending EP3723748A4 (fr) 2017-12-15 2018-12-14 Association comprenant de l'adapalène, du peroxyde de benzoyle et un agent du groupe des cicatrisants

Country Status (3)

Country Link
EP (1) EP3723748A4 (fr)
TR (1) TR201720497A2 (fr)
WO (1) WO2019190435A2 (fr)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103142460B (zh) * 2007-11-30 2016-08-31 盖尔德马研究及发展公司 含有至少一种萘甲酸衍生物、过氧化苯甲酰和至少一种成膜剂的组合物、它们的制备方法及其用途
EP2817069A1 (fr) * 2012-02-21 2014-12-31 Ranbaxy Laboratories Limited Composition comprenant un rétinoïde et du peroxyde de benzoyle
WO2016104618A1 (fr) * 2014-12-26 2016-06-30 ニプロ株式会社 Préparation dermatologique médicale à usage externe

Also Published As

Publication number Publication date
WO2019190435A2 (fr) 2019-10-03
TR201720497A2 (tr) 2019-07-22
EP3723748A4 (fr) 2021-07-21
WO2019190435A3 (fr) 2019-12-26

Similar Documents

Publication Publication Date Title
DK2450035T3 (en) Combination of adapalene and benzoyl peroxide for the treatment of acne lesions
JP5465011B2 (ja) 少なくとも１種のレチノイドおよび過酸化ベンゾイルを含むエマルジョン
WO2015075640A1 (fr) Formulation(s) pharmaceutique(s) stable (s) d'antibiotiques de la famille des tétracyclines
AU2006290364B2 (en) Composition comprising at least one naphthoic acid derivative and at least one compound of polyurethane polymer type or derivatives thereof, preparation processes therefor and uses thereof
BRPI0611713A2 (pt) composições tópicas para tratamento da pele
US20090191245A1 (en) Reduced-irritant dermatological compositions comprising at least one naphthoic acid compound and benzoyl peroxide and treatment of keratinization disorders therewith
WO2008017914A2 (fr) Préparations anti-acné à usage local contenant un rétinoïde (tazarotène ou adapalène), un antibiotique (clindamycine phosphate) et/ou un kératolytique (microéponges de peroxyde de benzoyle)
EP3700504A1 (fr) Composition pharmaceutique topique d'adapalène et de minocycline
US8709392B2 (en) Cosmetic/dermatological compositions comprising naphthoic acid compounds and polyurethane polymers
US20190255078A1 (en) Topical compositions with stable solubilized selective retinoids and/or tetracycline-class antibiotics
JP2010095534A (ja) フェノール誘導体およびレチノイド含有水−アルコール脱色ゲル
US20110117182A1 (en) Combination of dapsone with other anti-acne agents
JP2013500984A (ja) ダプソンとアダパレンの組み合わせ
WO2013124820A1 (fr) Composition comprenant un rétinoïde et du peroxyde de benzoyle
US20100029765A1 (en) Topical aqueous composition comprising tretinoin
US20100160439A1 (en) Dermatological compositions comprising at least one retinoid compound, an anti-irritant compound and benzoyl peroxide
WO2012138441A1 (fr) Composition et procédé pour le traitement topique de lésions cutanées
US20100068284A1 (en) Stable Fixed Dose Topical Formulation
EP3723747B1 (fr) Association comprenant de l'adapalène et du peroxyde de benzoyle
JP2012092067A (ja) 非ステロイド性消炎鎮痛外用剤
WO2019190435A2 (fr) Association comprenant de l'adapalène, du peroxyde de benzoyle et un agent du groupe des cicatrisants
WO2021035086A1 (fr) Système d'administration de solvant pour administration topique de principes actifs
US20110305747A1 (en) Combination of dapsone with other anti-acne agents

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20200714

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)
A4 Supplementary search report drawn up and despatched

Effective date: 20210621

RIC1 Information provided on ipc code assigned before grant

Ipc: A61K 31/192 20060101AFI20210615BHEP

Ipc: A61K 31/327 20060101ALI20210615BHEP

Ipc: A61K 9/06 20060101ALI20210615BHEP

Ipc: A61K 47/32 20060101ALI20210615BHEP

Ipc: A61K 9/107 20060101ALI20210615BHEP

Ipc: A61K 8/38 20060101ALI20210615BHEP

Ipc: A61K 8/67 20060101ALI20210615BHEP

Ipc: A61K 9/113 20060101ALI20210615BHEP

Ipc: A61Q 19/00 20060101ALI20210615BHEP

P01 Opt-out of the competence of the unified patent court (upc) registered

Effective date: 20230708

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

17Q First examination report despatched

Effective date: 20231222