EP2104496A2 - Verwendung von nepafenac oder derivaten davon zur behandlung von hauterkrankungen in verbindung mit einem keratinisationsleiden einschliesslich einer immunallergischen entzündungskomponente - Google Patents

Verwendung von nepafenac oder derivaten davon zur behandlung von hauterkrankungen in verbindung mit einem keratinisationsleiden einschliesslich einer immunallergischen entzündungskomponente

Info

Publication number
EP2104496A2
EP2104496A2 EP07871972A EP07871972A EP2104496A2 EP 2104496 A2 EP2104496 A2 EP 2104496A2 EP 07871972 A EP07871972 A EP 07871972A EP 07871972 A EP07871972 A EP 07871972A EP 2104496 A2 EP2104496 A2 EP 2104496A2
Authority
EP
European Patent Office
Prior art keywords
derivatives
composition
compound
formula
nepafenac
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.)
Withdrawn
Application number
EP07871972A
Other languages
English (en)
French (fr)
Inventor
Irina Safonova
Cécile COUSIN
Leila Zarif
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.)
Galderma Research and Development SNC
Original Assignee
Galderma Research and Development SNC
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 Galderma Research and Development SNC filed Critical Galderma Research and Development SNC
Publication of EP2104496A2 publication Critical patent/EP2104496A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
    • 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
    • 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
    • A61P17/06—Antipsoriatics
    • 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
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • nepafenac or its derivatives for the treatment of dermatological disorders linked to a disorder of keratinization that may have an inflammatory immunoallergic component
  • the present invention relates to the use of at least one compound of formula (I) or its derivatives, preferably nepafenac, for the manufacture of a pharmaceutical composition intended for the treatment of dermatological disorders related to a disorder of the keratinization may have an inflammatory immunoallergic component, including rosacea, acne, psoriasis or atopic dermatitis (eczema).
  • an inflammatory immunoallergic component including rosacea, acne, psoriasis or atopic dermatitis (eczema).
  • Rosacea is a chronic and progressive joint inflammatory dermatosis related to vascular relaxation. It mainly affects the central part of the face and is characterized by facial redness or hot flushes, facial erythema, papules, pustules, and telangiectasias. In severe cases, particularly in man, a facial elephantiasis may develop which most commonly presents as swelling of the soft tissue of the nose producing bulbous swelling called rhinophyma.
  • Rosacea usually occurs between the ages of 25 and 70, and is much more common in fair-skinned people. It affects more particularly women, although this affection is generally more severe in the man. Rosacea is chronic and persists for years with periods of exacerbation and remission.
  • rosacea The pathogenesis of rosacea is poorly understood. Many factors can be involved without necessarily inducing this condition. These are for example psychological factors, gastrointestinal disorders, environmental factors (exposure to the sun, temperature, humidity) and emotional (stress), food (alcohol, spices), hormonal, vascular, or even an infection with Helicobacter pillori.
  • the minor forms of rosacea can be treated by topical treatments, for example metronidazole, azelaic acid, benzoyl peroxide, or retinoic acid. As for the most severe forms of the disease, they respond well to general antibiotherapy with cyclins. However, these treatments have unpleasant side effects for the patient, such as irritation or intolerance phenomena.
  • acne conglobata keloid acne
  • drug acne recurrent acne acne
  • necrotic acne necrotic acne
  • neonatorum acne premenstrual acne
  • occupational acne rosacea
  • senile acne solar acne, and acne vulgaris.
  • Acne vulgaris also called polymorphous juvenile acne
  • Stage 1 corresponds to comedonal acne characterized by a large number of open and / or closed comedones, and microcysts.
  • Stage 2 or papulopustular acne, is of mild to moderate severity. It is characterized by the presence of open and / or closed comedones, microcysts, but also red papules and pustules. It mainly affects the face and leaves few scars.
  • Stage 3 or papulocomedonian acne is more serious and extends to the back, thorax and shoulders. It is accompanied by a larger number of scars.
  • Stage 4 or nodulocystic acne, is accompanied by numerous scars. It presents nodules as well as voluminous pustules violaceous and painful.
  • the different forms of acne described above can be treated with active agents such as anti-seborrhoeic agents and anti-infectious agents, for example benzoyl peroxide (in particular the product Eclaran® marketed by the company Pierre Fabre), with retinoids such as than tretinoin (in particular Retacnyl® marketed by Galderma) or isotretinoin (Roaccutane® product marketed by Roche Laboratories).
  • active agents such as anti-seborrhoeic agents and anti-infectious agents, for example benzoyl peroxide (in particular the product Eclaran® marketed by the company Pierre Fabre), with retinoids such as than tretinoin (in particular Retacnyl® marketed by Galderma) or isotretinoin (Roaccutane® product marketed by Roche Laboratories).
  • atopic dermatitis is an inflammatory erythematous-erythematosquamous inflammatory dermatosis that evolves by pushing, itching, which mainly affects the infant.
  • the acute phase is chronologically characterized by: an erythematous phase,
  • the main, constant diagnostic criterion is pruritus.
  • the following criteria can also be used to identify the pathology: dermatological history of involvement of wrinkles, anterior ankles or neck; history of xerosis (dry skin); personal history of asthma or rhinitis: fold dermatitis or eczema of the cheeks, forehead and outer face of the limbs in children under 4 years of age; onset before 2 years of age: ichthyosis and / or keratosis pilaris and / or palmar hyperinfinity, tendency to skin infections, nipple eczema, cheilitis, recurrent conjunctivitis, Denny Morgan's fold, keratoconus, anterior capsular cataract, periorbital pigmentation , pityriasis alba (dartres), irritation of anterior neck folds, pruritus to perspiration, intolerance to wool and lipid solvents, white dermographism or white line delayed onset
  • Atopic dermatitis is probably aggravated by pollution, but also paradoxically good hygiene with the use of detergents that alter the barrier skin.
  • This dermatitis is a symptomatic treatment that aims to control inflammation and itching to relieve the patient.
  • the skin care must be daily, and therefore require good patient compliance: washing with a non-detergent product, application of a dermocoticoid on eczema and an emollient on the rest of the body.
  • rosacea we are still looking for an effective and safe treatment for the patient.
  • Psoriasis is a chronic dermatosis characterized by erythematous squamous plaques, infiltrated, well limited often itchy (which itch). Pruritus is regularly present in patients who live in hot regions, but it is found only in 20 to 30% of patients in Northern Europe.
  • the preferred sites of psoriasis are the elbows, knees, buttocks or areas of friction or micro-trauma, as well as the scalp.
  • the pathogenesis of psoriasis is complex.
  • the psoriatic lesion is characterized by epidermal hyperproliferation with an increase in keratinocytes and moderate inflammation of the dermis and epidermis.
  • Psoriasis may be due to a genetic abnormality associated with inflammatory processes.
  • the signals involved in dermoepidermal interactions are not yet clearly understood.
  • the purpose of anti-psoriatic treatments is to reduce the severity of the dermatosis in order to restore the physical and psychological well-being of the patient.
  • Current local treatments are used for moderate forms of psoriasis and systemic treatments are reserved for severe forms.
  • most anti-psoriatic treatments have variable efficacy, more or less severe side effects and are sometimes uncomfortable to use. There is therefore a need for effective and safe treatment for the patient.
  • nepafenac the compound of formula (I) below (nepafenac) proves to be suitable for the treatment of dermatological disorders related to a disorder of keratinization that may have a component inflammatory immunoallergic and more particularly well suited for the treatment of rosacea, acne, psoriasis or atopic dermatitis (eczema):
  • nepafenac 2-amino-3-benzoylphenylacetamide - called nepafenac
  • nepafenac 2-amino-3-benzoylphenylacetamide -
  • Such a compound has analgesic and anti-pyretic properties, and can be used in the treatment of ophthalmic pathologies.
  • nepafenac may also be useful in the treatment of various retinopathies and cancers.
  • a pharmaceutical composition intended for the treatment of dermatological disorders linked to a disorder of keratinization which may have an inflammatory immunoallergic component, advantageously rosacea, acne, psoriasis or atopic dermatitis (eczema).
  • Derivatives of the compound of formula (I) are in particular pharmaceutically acceptable salts, acids and hydrates.
  • salts is meant in particular salts formed with a pharmaceutically acceptable acid or base.
  • the salts of the compound of formula (I) are preferably the ammonium forms (-NH 3 + ) of this compound.
  • acids preferably means the carboxylic acid form of the compound of formula (I), ie in which the -NH 2 radical of the acetamide function is replaced by an -OH radical. Such a form corresponds to amfenac (2-amino-3-benzoylphenylacetic acid).
  • the acid salts are also covered by the present invention; such salts are those formed between the acids of the compound of formula (i) and metal cations such as sodium, potassium, calcium, magnesium, zinc, copper, aluminum, preferably sodium.
  • metal cations such as sodium, potassium, calcium, magnesium, zinc, copper, aluminum, preferably sodium.
  • hydrates is meant the compounds obtained by mixing with water.
  • compositions comprise, in a pharmaceutically acceptable medium, at least one compound of formula (I) or its derivatives, preferably nepafenac.
  • pharmaceutically acceptable medium is meant a medium compatible with the skin, mucous membranes and / or integuments.
  • composition according to the invention comprises from 0.001 to 10% of compound of formula (I) or its derivatives by weight relative to the total weight of the composition.
  • composition according to the invention contains from 0.1 to 5% of compound of formula (I) or its derivatives by weight relative to the total weight of the composition.
  • the pharmaceutical composition that can be used according to the invention is intended for the treatment of the skin and can be administered topically, parenterally or orally. Preferably, the composition is administered topically.
  • the pharmaceutical composition may be in liquid, pasty or solid form, in the form of powders and more particularly in the form of tablets, capsules, dragees, syrups, suspensions, solutions, powders, granules , emulsions, microspheres or nanospheres or lipid or polymeric vesicles allowing controlled release.
  • the composition may be in the form of solutions or suspensions for infusion or injection.
  • topical means a composition specifically adapted for application on the skin and not on the conjunctiva of the eye.
  • the composition may be in liquid, pasty or solid form, and more particularly in the form of ointments, creams, milks, ointments, powders, soaked swabs, syndets, wipes, solutions, gels, sprays, mousses, suspensions, lotions, sticks, shampoos, or washing bases. It may also be in the form of suspensions of microspheres or nanospheres or lipid or polymeric vesicles or polymeric patches and hydrogels allowing controlled release.
  • This composition for topical application may be in anhydrous form, in aqueous form or in the form of an emulsion.
  • the topical pharmaceutical composition according to the invention is in the form of a cream or lotion emulsion, a gel, or a solution.
  • the composition according to the invention when in the form of an emulsion, it comprises at least one surfactant.
  • the conventional emulsions as described in the prior art are unstable quasi-homogeneous systems of two immiscible liquids, one of which is dispersed in the other in the form of fine droplets (micelles).
  • This dispersion is stabilized thanks to the action of surfactant emulsifiers which modify the structure and the ratio of the forces at the interface, and thus increase the stability of the dispersion by reducing the interfacial tension energy.
  • the surfactant emulsifiers are amphiphilic compounds which have a hydrophobic part having an affinity for the oil and a hydrophilic part having an affinity for water thus creating a link between the two phases. Ionic or nonionic emulsifiers thus stabilize the oil / water emulsions by adsorbing at the interface and forming lamellar layers of liquid crystals.
  • the emulsifying power of nonionic surfactants is closely related to the polarity of the molecule. This polarity is defined by the HLB (Hydrophilic Balance / ⁇ pophilus).
  • HLB Hydrophilic Balance / ⁇ pophilus
  • the conventional emulsions are generally stabilized by a mixture of surfactants whose HLB may be quite different but whose proportion in the mixture corresponds to the required HLB of the fatty phase to be emulsified.
  • surfactants that may be used according to the invention, mention may be made, by way of example, of the glyceryl / PEG100 stearate sold under the name Arlacel 165FL by the company Uniqema or under the name Simulsol 165 by the company SEPPIC, esters of polyoxyethylenated fatty acids such as Arlatone 983 from the company Uniqema or the polyoxyethylenated stearyl alcohol (2) sold under the name Brij72 combined with the polyethylenated stearyl alcohol (21) sold under the name Brij721 by the company Uniqema, sorbitan esters such as sorbitan oleate sold under the name Arlacel 80 by ICI or sold under the name of Crill 4 by Croda, sorbitan sesquioleate sold under the name Arlacel 83 by the company ICI or sold under the name of Montane 83 by the company SEPPIC, or the isostearate of sorbitan;
  • composition according to the invention advantageously comprises up to 15% by weight of suitable surfactant emulsifier, preferably from 2 to 12% by weight and more particularly from 2 to 6% by weight relative to the total weight of the composition.
  • composition in the form of an emulsion thus comprises: a) an oily phase comprising fatty substances; b) at least one surfactant emulsifier; c) at least one compound selected from the compound of formula (I) and its derivatives; d) one or more solvents and / or propenetrants of the active substance (s); e) and water.
  • the oily phase of the composition according to the invention may comprise, for example, vegetable, mineral, animal or synthetic oils, silicone oils, Guerbet alcohols or other fatty substances and mixtures thereof.
  • paraffin oils of different viscosity such as Primol 352, Marcol 82, Marcol 152 sold by Esso.
  • sweet almond oil there may be mentioned sweet almond oil, palm oil, soybean oil, sesame oil, sunflower oil.
  • esters such as cetearyl isononanoate sold under the name Cetiol SN by the company Cognis France, diisopropyl adipate, for example, the product sold under the name Ceraphyl 230 by the company ISF, palmitate d. isopropyl as the product sold under the name Crodamol IPP by the company Croda, caprylic capric triglyceride such as Miglyol 812 sold by the company HuIs / Lambert River.
  • esters such as cetearyl isononanoate sold under the name Cetiol SN by the company Cognis France, diisopropyl adipate, for example, the product sold under the name Ceraphyl 230 by the company ISF, palmitate d. isopropyl as the product sold under the name Crodamol IPP by the company Croda, caprylic capric triglyceride such as Miglyol 812 sold by the company HuIs / Lambert River.
  • silicone oil mention may be made of a dimethicone such as the product sold under the name of Dow Corning 200 fluid, a cyclomethicone such as the product sold under the name Dow Corning 244 fluid by Dow Corning or the product sold under the name Mirasil CM5 by SACI-CFPA.
  • fatty acids such as stearic acid, fatty alcohols such as stearyl alcohol, cetostearyl alcohol and cetyl alcohol or their derivatives, and waxes such as beeswax or wax. carnauba, candellilla wax, as well as gums, in particular silicone gums.
  • ingredients of the oily phase may be chosen in a varied manner by those skilled in the art in order to prepare a composition having the desired properties, for example in consistency or in texture.
  • the oily phase of the composition according to the invention comprises a synthetic oil and / or a silicone oil, as synthetic oil, isopropyl palmitate is preferred as the product sold under the name Crodamol IPP by the company Croda or isopropyl myristate, such as the product sold under the name Crodamol IPM by Croda, as a silicone oil, a dimethicone is preferred.
  • the oily phase of the emulsion according to the invention may be present in a content of between 3 and 50% by weight relative to the total weight of the composition and preferably between 6 and 20% by weight.
  • solvent and / or propenetrant of the compound of formula (I) or its derivatives mention will preferably be made of propylene glycol and ethanol-type alcohols. isopropanol, butanol, N-methyl 2 pyrrolidone or DMSO, polysorbate 80, phenoxyethanol and mixtures thereof.
  • composition of the invention contains from 0.1% to 20% and preferably from 1% to 10% of a solvent and / or propenetrant of the compound of formula (I) or its derivatives.
  • composition of the invention also contains water ranging from 30 to 95% and preferably from 60 to 80% by weight relative to the total weight of the composition.
  • the water used in the composition according to the invention will preferably be purified water.
  • the composition according to the invention may also be in the form of a gel; it then comprises one or more gelling compounds, ranging from 0.01 to 5% by weight relative to the total weight of the composition.
  • gelling agents that can be used in the composition according to the invention, mention may be made of carboxyvinyl polymers (carbomers) and, by way of non-limiting examples of carbomer, Carbopol 981, Carbopol ETD 2020, Carbopol 980, Carbopol Ultrez 10 NF, Pemulen TR1 sold by the company NOVEON.
  • cellulose derivatives for example hydroxypropylmethylcellulose, or hydroxyethylcellulose
  • xanthan gums aluminum / magnesium silicates such as Veegum K or Veegum Ultra sold by Vanderbilt, guar gums and the like
  • polyacrylamides such as the polyacrylamide / isoparaffin C13-14 / laureth-7 mixture such as for example sold by SEPPIC under the name Sepigel 305 or the acrylamide mixture, AMPS copolymer dispersion 40% / isohexadecane under the name of Simulgel 600PHA, or the family of modified starches such as Solanace Structure sold by National Starch or their mixtures.
  • composition of the invention preferably contains from 0.01% to 5%, and preferably from 0.1 to 3% of gelling agent.
  • composition when in the form of a solution, it comprises, besides the compound of formula (I) or its derivatives, an aqueous or oily solution, and optionally one or more solvents and / or propenetrating actives as described above.
  • the pharmaceutical composition according to the invention may also contain inert additives or combinations of these additives, such as
  • UV-A and UV-B filters are UV-A and UV-B filters
  • additives may be present in the composition of 0.001 to 20% by weight relative to the total weight of the composition.
  • the use of the compound of formula (I) or its derivatives as a medicament, and more particularly for the manufacture of a topical pharmaceutical composition according to the invention is particularly intended for the treatment of rosacea, psoriasis or atopic dermatitis (eczema ).
  • compositions comprising the compound of formula (I) or its derivatives will now be given.
  • EXAMPLE 3 Biological Test The evaluation of a compound of formula (I) is carried out in a model of inflammation induced by the topical application of an arachidonic acid solution to the mouse ear. The intensity of the inflammatory response is then assessed by measuring the thickness of the ear at 1, 2 and 6 hours, which reflects the oedematous response. The activity of the compound of formula (I) is characterized by the percentage inhibition of response compared to untreated animals.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Dispersion Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
EP07871972A 2006-12-19 2007-12-19 Verwendung von nepafenac oder derivaten davon zur behandlung von hauterkrankungen in verbindung mit einem keratinisationsleiden einschliesslich einer immunallergischen entzündungskomponente Withdrawn EP2104496A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0655655A FR2909876A1 (fr) 2006-12-19 2006-12-19 Utilisation du nepafenac ou ses derives pour le traitement de desordres dermatologiques
PCT/FR2007/052559 WO2008084171A2 (fr) 2006-12-19 2007-12-19 Utilisation du nepafenac ou ses derives pour le traitement de la rosacee, l' acne, le psoriasis et la dermatite atopique

Publications (1)

Publication Number Publication Date
EP2104496A2 true EP2104496A2 (de) 2009-09-30

Family

ID=38029700

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07871972A Withdrawn EP2104496A2 (de) 2006-12-19 2007-12-19 Verwendung von nepafenac oder derivaten davon zur behandlung von hauterkrankungen in verbindung mit einem keratinisationsleiden einschliesslich einer immunallergischen entzündungskomponente

Country Status (12)

Country Link
US (1) US20090312429A1 (de)
EP (1) EP2104496A2 (de)
JP (1) JP2010513424A (de)
KR (1) KR20090094095A (de)
CN (1) CN101563073A (de)
AU (1) AU2007343214A1 (de)
BR (1) BRPI0719467A2 (de)
CA (1) CA2672377A1 (de)
FR (1) FR2909876A1 (de)
MX (1) MX2009006212A (de)
RU (1) RU2009127747A (de)
WO (1) WO2008084171A2 (de)

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CN102341122A (zh) * 2009-03-11 2012-02-01 兴和株式会社 含有镇痛-抗炎症剂的外用剂
EP2329849B1 (de) 2009-11-18 2015-04-29 Galderma Research & Development Kombination aus einem Alpha-2-Adrenozeptor-Agonisten und einem nichtsteroidalen entzündungshemmenden Mittel zur Behandlung oder Prävention einer Entzündungskrankheit der Haut
US20130123194A1 (en) * 2011-11-15 2013-05-16 Allergan, Inc. Autoclavable suspensions of cyclosporin a form 2
WO2014207769A1 (en) 2013-06-27 2014-12-31 Mylan Laboratories Ltd Process for the preparation of nepafenac

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AR030345A1 (es) * 2000-08-14 2003-08-20 Alcon Inc Metodo de tratamiento de desordenes relacionados con angiogenesis
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WO2005076987A2 (en) * 2004-02-10 2005-08-25 Santarus, Inc. Combination of proton pump inhibitor, buffering agent, and nonsteroidal anti-inflammatory agent
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Also Published As

Publication number Publication date
WO2008084171A2 (fr) 2008-07-17
CA2672377A1 (fr) 2008-07-17
CN101563073A (zh) 2009-10-21
WO2008084171A3 (fr) 2008-10-16
BRPI0719467A2 (pt) 2014-10-29
RU2009127747A (ru) 2011-01-27
KR20090094095A (ko) 2009-09-03
JP2010513424A (ja) 2010-04-30
FR2909876A1 (fr) 2008-06-20
WO2008084171A9 (fr) 2009-07-23
MX2009006212A (es) 2009-06-30
AU2007343214A1 (en) 2008-07-17
US20090312429A1 (en) 2009-12-17

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