EP2182921A2 - Médicaments pour l'administration transdermique à des animaux - Google Patents

Médicaments pour l'administration transdermique à des animaux

Info

Publication number
EP2182921A2
EP2182921A2 EP08773993A EP08773993A EP2182921A2 EP 2182921 A2 EP2182921 A2 EP 2182921A2 EP 08773993 A EP08773993 A EP 08773993A EP 08773993 A EP08773993 A EP 08773993A EP 2182921 A2 EP2182921 A2 EP 2182921A2
Authority
EP
European Patent Office
Prior art keywords
alcohol
ketoprofen
pharmaceutical
acid
diclofenac
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Withdrawn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
EP08773993A
Other languages
German (de)
English (en)
Inventor
Birgitta Pausch
Dirk Mertin
Christel Mueller-Goymann
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.)
Elanco Animal Health GmbH
Original Assignee
Bayer Animal Health GmbH
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 Bayer Animal Health GmbH filed Critical Bayer Animal Health GmbH
Publication of EP2182921A2 publication Critical patent/EP2182921A2/fr
Withdrawn legal-status Critical Current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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • 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
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • 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
    • A61K9/0017—Non-human animal skin, e.g. pour-on, spot-on
    • 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
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • the invention relates to compositions which increase the transdermal permeability of the skin and thus lead to an increased drug permeability and the use of these compositions for the preparation of medicaments for external use.
  • the transdermal application of active ingredients is severely limited by the poor permeability of the skin, in particular of the stratum corneum. Due to the highly restricted permeability of the skin, only small molecules (molecular mass ⁇ 500 Da) with a lipophilic character can overcome this barrier. For all other active ingredients whose transdermal application is desired, the transport through the skin must be improved. Therefore, drugs for transdermal application are rarely used as a pure substance, but are often part of complex formulations consisting of basic and excipients.
  • hydrophilic e.g., water, alcohols
  • hydrophobic e.g., triglycerides, waxes
  • auxiliaries are emulsifiers, gel formers, preservatives and antioxidants.
  • One way to promote permeation through the skin is to treat preparations for transdermal application with thickeners to ensure better adhesion to the skin. This is practiced for medicinal products in the human as well as in the veterinary field [WO04 / 017998, JP2003095983, US Pat. No. 5,093,133].
  • lipophilic components and alcohols can be used. If thickeners are used, evaporation of the alcohol component is desirable in order to achieve better thickening [WO 2005-120473].
  • aqueous systems which may contain both hydrophilic and hydrophobic basic substances [[Brinkmann (2003)], WO99 / 022716] and require further additives such as emulsifiers (surfactants) for stabilization [WO04 / 017998, US Pat. WO01 / 089469, WO99 / 022716, WO98 / 051280].
  • emulsifiers surfactants
  • Most of the oil and alcohol component is added only to a small extent [WO02 / 096435, EP 428352, EP 91964, WO92 / 16237, US 5,093,133].
  • the object underlying the invention was therefore to provide formulations for transdermal applications in which the disadvantages of the known formulations described above are eliminated or reduced.
  • the object was to provide formulations which bring about improved permeation of active substance salts and by means of which the complexity of the formulation can be reduced.
  • a pharmaceutical preparation which, according to the present invention, in a mixture consisting of a. 40% - 60% (m / m) of a lipophilic component, b. 40% - 60% (m / m) of an alcohol with chain length C1-C6 and c. 0% - 10% (m / m) water, one or more active ingredient salts and excipients.
  • Another object of the invention are the uses defined in the claims.
  • the formulation according to the invention contains at least one active substance salt from the group of painkilling substances (analgesics).
  • Analgesics include opioids such as buprenorphine, codeine, dihydrocodeine, fentanyl, hydromorphone, methadone, morphine, oxycodone, pentazocine, pethidine, piritramide, tilidine, tramadol, as well as non-opioid analgesics such as aceclofenac, acemetacin, acetylsalicylic acid, bufexamac , Carprofen, Celecoxib, Deraco xib, diclofenac, etofenamate, etoricoxib, felbinac, flufenamic acid, flunixin, flupirtine, flurbiprofen, ibuprofen, indomethacin, ketoprofen, lonazolac, lornoxi
  • the active substance salts mentioned can also be used in the form of their hydrates, enantiomers or racemates are also included according to the invention. Preference is given here to the alkaline earth and alkali metal salts of the active compounds mentioned, in particular diclofenac Na, di-cofenac-K, ketoprofen Na, ketoprofen K, and organic amine salts, such as, for example, Diclofenac diethylamine.
  • the lipophilic component is selected from the group consisting of neutral oils and fatty acid esters.
  • Neutral oils are for example synthetic triglycerides such as caprylic / capric acid triglycerides, triglyceride mixtures with fatty acids of chain length C8-C12 or other specially selected natural fatty acids (eg Miglyol 810), or eg propylene glycol dicaprylate and propylene glycol dicaprate or mixtures thereof (such as Migylol 840).
  • Fatty acid esters are, for example, isopropyl myristate, isopropyl palmitate, isopropyl stearate, ethyl stearate, lauric acid hexyl ester, dipropylene glycol pelargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C 16-Cl 8, caprylic / capric acid esters of saturated fatty alcohols of chain length C 12 -C 18, oleic acid oleate, oleic acid decyl ester, Ethyl oleate and waxy fatty acid esters, such as artificial duck short-gland fat, other esters such as di-n-butyryl adipate, ethyl lactate, dibutyl phthalate, diisopropyl adipate.
  • the group of lipophilic component Partialglyceridgemische of saturated or unsaturated, possibly hydroxyl-containing fatty acids, mono- and diglycerides of C8 / C10 fatty acids, paraffin oils, silicone oils, vegetable oils such as sesame oil, almond oil, castor oil, fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, Cetylstearyl alcohol, oleyl alcohol and fatty acids such as oleic acid, lauric acid, palmitic acid, stearic acid.
  • the mentioned lipophilic components can be used alone or as a mixture.
  • the alcohol component is an alcohol with a chain length of C1-C6.
  • Alcohols are preferably selected from the group consisting of isopropanol, n-propanol, ethanol, methanol, n-butanol, isobutanol, tert-butanol, n-pentanol, n-hexanol, propylene glycol, glycerol and their mixtures.
  • the lipophilic component is selected from the group of the fatty acid esters or the neutral oils and leads to pharmaceutical preparations which are prepared in a mixture consisting of a. 40% - 60% (m / m) of a fatty acid ester or a neutral oil, b. 40% - 60% (m / m) of an alcohol with chain length C 1 -C6 and c. 0% - 10% (m / m) water, one or more active ingredient salts and excipients.
  • a preferred subject of the invention are pharmaceutical preparations which are in a mixture consisting of a. 40% - 60% (m / m) of a fatty acid ester or a neutral oil and b. 40% - 60% (m / m) of an alcohol with the chain length C1-C6, one or more active substance salts and auxiliaries.
  • the alcohol is isopropanol.
  • a particularly preferred subject matter of the invention are pharmaceutical preparations which are prepared in a mixture consisting of a. 40% - 60% (m / m) isopropyl myristate and b. 40% - 60% (m / m) isopropanol, one or more active substance salts and auxiliaries.
  • compositions which are in a mixture consisting of c. 40% - 60% (m / m) Miglyol 840 and d. 40% - 60% (m / m) isopropanol, one or more active substance salts and auxiliaries. It has been found that a formulation containing approximately equal parts of alcohol and lipophilic component is preferably of good spreading consistency and causes an unexpectedly high permeation of the active ingredient, especially if the formulation is anhydrous.
  • the use of the term "anhydrous" does not exclude the possibility that water is present in the formulation up to 5% by weight. Preference is given to the preparations described if they contain less than 2% (w / w) of water, more preferably less than 1% (w / w).
  • a mixture of lipophilic component and alcohol of in each case 45% -55% (m / m) and 0% -10% (m / m) of water is preferably used.
  • Particularly preferred is a mixture of lipophilic component and alcohol of 50% (m / m) is used.
  • antioxidants can be added as further auxiliaries.
  • Antioxidants are, for example, fumaric acid, maleic acid, ⁇ -tocopherol, ascorbic acid palmitate, butylhydroxyanisole, butylhydroxytoluene, propyl gallate.
  • Preservatives are, for example, sorbic acid, benzyl alcohol or phenoxyethanol.
  • Viscosity-increasing substances are, for example, fumed silica, bentonite, aluminum stearate, zinc stearate, magnesium aluminum silicate, oleyl oleate, cetyl palmitate, yellow or white wax, ethylene / propylene / styrene and butylene / ethylene / styrene copolymers, carbopols, cellulose derivatives such as Ethyl cellulose, hydroxypropyl cellulose, methyl cellulose, polymeric alcohols such as polyvinyl alcohol.
  • the preparations described preferably come without surfactants as auxiliaries and thus lead to the reduction of the complexity of the preparation. More preferably, the described formulations are devoid of excipients needed to adjust a pH, i. which change the degree of protonation of the active substance salt.
  • the pharmaceutical preparation is applied to the coat or the skin.
  • a pharmaceutical preparation containing the corresponding active ingredient is applied topically to the animal, which subsequently penetrates into the coat dress.
  • the active substance is absorbed transdermally.
  • the topical application is done for example in the form of spraying, pouring and rubbing.
  • the preparations according to the invention require no occlusion-forming cover. Due to the well-spreading properties of the low-viscosity formulation, this penetrates quickly into the coat dress.
  • the coat over the skin subsequently prevents the volatile components from evaporating too quickly from the surface of the skin before they can exert their penetration-enhancing effect on the stratum corneum.
  • the topical application of the preparation according to the invention is carried out on the body site affected by the disease, preferably on the joint region, in particular the knee joints.
  • the pharmaceutical preparation is used in animals, more preferably in horses, dogs and cats.
  • Another object of the invention is the use of a mixture consisting of a lipophilic component and an alcohol of chain length Cl -C6 with in each case a share of 40% -60% (m / m) and water in a proportion of 0% -10 % (m / m) containing one or more active agent salts and excipients for the preparation of a pharmaceutical preparation.
  • the lipophilic component is a fatty acid ester or a neutral oil.
  • the alcohol is isopropyl alcohol.
  • the lipophilic component is is isopropyl myristate or Migylol 840 and the alcohol isopropanol.
  • the abovementioned mixtures are anhydrous. In a further particularly preferred form, the abovementioned mixtures are used non-occlusively.
  • a mixture of lipophilic component and alcohol of in each case 45% -55% (m / m) is used, which may contain 0% -10% (m / m) of water.
  • a mixture of lipophilic component and alcohol of 50% (m / m) is used.
  • the preparation of the preparation according to the invention can be carried out in a manner known to the person skilled in the art. Solutions or suspensions may be prepared by homogeneously mixing lipophilic component and alcohol and dissolving or suspending the active salt in this mixture.
  • the amount of active ingredient salt varies depending on the purpose, substance and size of the skin surface to which the composition is applied. The skilled worker is aware of how much active ingredient salt is to be used for a use. Whether further adjuvants must be supplied is known to the skilled person depending on the application of the preparation. The invention is explained in more detail by the following examples:
  • Ketoprofen sodium is added to saturation in a mixture of Miglyol 840, isopropyl alcohol (IPA) and water (45:45:10 m / m / m), a mixture of Miglyol 840, isopropyl alcohol (IPA) (50:50 m / m), a mixture of isopropyl alcohol (IPA) and water (50:50 m / m) and water dispersed. This results in suspensions with the thermodynamic active substance activity 1.
  • Each 100 ⁇ l is applied to the atomized (700 +/- 50 ⁇ m) horse skin clamped in suitable measuring cells with donor and acceptor compartments.
  • Figure 1 shows the permeation of the preparations of the invention.
  • ketoprofen acid or ketoprofen sodium is added to saturation in a mixture of isopropyl myristate (IPM) and isopropyl alcohol (IPA) (50:50 m / m) or a mixture of isopropyl myristate (IPM), isopropyl alcohol (IPA) and water (45:45:10 m / m / m) dispersed. This results in suspensions with the thermodynamic drug activity.
  • FIG. 2 shows the permeation of ketoprofen acid and ketoprofen sodium from the preparations according to the invention.
  • the permeation curves make it clear that the preparation according to the invention is suitable both for hydrophilic and for lipophilic active ingredients.
  • the highest levels can be achieved with the sodium salt of the drug in an anhydrous mixture of isopropyl myristate and isopropyl alcohol.
  • Example 3 2.5% (w / w) ketoprofen sodium is dissolved in a mixture of isopropyl myristate (IPM), isopropyl alcohol (IPA) and water (45:45:10 m / m / m). This results in a clear solution.
  • IPM isopropyl myristate
  • IPA isopropyl alcohol
  • Each 100 ⁇ l is applied to the atomized (700 +/- 50 ⁇ m) horse skin clamped in suitable measuring cells with donor and acceptor compartments.
  • diclofenac sodium or diclofenac acid are dispersed to saturation in a mixture of isopropyl myristate (EPM) and isopropyl alcohol (IPA) (50:50 m / m). This results in suspensions with the thermodynamic drug activity.
  • EPM isopropyl myristate
  • IPA isopropyl alcohol
  • FIG. 3 shows the permeation from the preparations according to the invention.
  • Diclofenac sodium is dissolved in a mixture of isopropyl myristate (IPM), isopropyl alcohol (IPA) (50:50 m / m). This results in clear solutions.
  • IPM isopropyl myristate
  • IPA isopropyl alcohol
  • Each 100 ⁇ l is applied to the atomized (700 +/- 50 ⁇ m) horse skin clamped in suitable measuring cells with donor and acceptor compartments.
  • Figure 4 shows the permeation of the preparations of the invention.
  • Ketoprofen is dispersed to saturation in mixtures of isopropropyl myristate (IPM) and isopropyl alcohol (IPA) in various proportions. This results in suspensions with the thermodynamic drug activity.
  • IPM isopropropyl myristate
  • IPA isopropyl alcohol
  • Ketoprofen is dispersed to saturation in mixtures of Miglyol 840 and isopropyl alcohol (IPA) in various proportions. This results in suspensions with the thermodynamic drug activity.
  • Each 100 ⁇ l is applied to the atomized (700 +/- 50 ⁇ m) horse skin clamped in suitable measuring cells with donor and acceptor compartments.
  • Example 8 Ketoprofen is dispersed to saturation in a mixture of Miglyol 840 and isopropyl alcohol (IPA) (50:50 m / m). The result is a suspension with the thermodynamic drug activity. 1
  • IPA isopropyl alcohol
  • IPM Isopropyl myristate
  • IPA isopropyl alcohol
  • IPM Isopropyl myristate
  • ethanol 50:50 m / m
  • Each 100 ⁇ l is applied to the atomized (700 +/- 50 ⁇ m) horse skin clamped in suitable measuring cells with donor and acceptor compartments.
  • Table 4 Active substance flux after application of 100 ⁇ l of the formulations from Example 8 on the atomized horse skin (700 +/- 50 ⁇ m), n-3-4
  • ketoprofen sodium is dispersed to saturation in a mixture of Miglyol 840 and isopropyl myristate (IPM) (50:50 m / m). The result is a suspension with the thermodynamic drug activity. 1
  • EPM Isopropyl myristate
  • EPA isopropyl alcohol
  • E? M isopropyl myristate
  • ethanol 50:50 m / m
  • Ketoprofen sodium is dispersed to saturation in a mixture of paraffin oil and isopropyl alcohol (50:50 m / m) to leave an insoluble residue. The result is a suspension with the thermodynamic drug activity.
  • Ketoprofen sodium is dispersed in a mixture of sesame oil and isopropyl alcohol (50:50 m / m) in analogy to Example 10.
  • Ketoprofen sodium is dispersed in a mixture of isopropyl myristate and methanol (50:50 m / m) in analogy to Example 10.
  • Ketoprofen sodium is dispersed in a mixture of isopropyl myristate and butanol (50:50 m / m) in analogy to Example 10.
  • Example 14 Analogously to Examples 9-13, diclofenac sodium is used.
  • Figure 1 Permeation curves of the mean, cumulatively permeated amount of active substance (WSt [ ⁇ g / cm 2 ]) over time in hours (t [h]) from suspensions of
  • Figure 2 Permeation curves of the mean, cumulatively permeated amount of active substance (WSt [ ⁇ g / cm 2 ]) over time in hours (t [h]) from suspensions of:
  • Figure 3 Permeation curves of the mean, cumulatively permeated amount of active substance (WSt [ ⁇ g / cm 2 ]) over time in hours (t [h]) from suspensions of: diclofenac-Na in isopropyl myristate - isopropyl alcohol 50: 50% m / m (filled Squares ⁇ ) and

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Zoology (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Dispersion Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne des préparations pharmaceutiques pour des animaux, lesquelles sont appliquées sur le pelage ou sur la peau des animaux, leur agent actif étant alors absorbé à travers la peau.
EP08773993A 2007-07-26 2008-07-15 Médicaments pour l'administration transdermique à des animaux Withdrawn EP2182921A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007034976A DE102007034976A1 (de) 2007-07-26 2007-07-26 Arzneimittel zur transdermalen Anwendung bei Tieren
PCT/EP2008/005747 WO2009012908A2 (fr) 2007-07-26 2008-07-15 Médicaments pour l'administration transdermique à des animaux

Publications (1)

Publication Number Publication Date
EP2182921A2 true EP2182921A2 (fr) 2010-05-12

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EP08773993A Withdrawn EP2182921A2 (fr) 2007-07-26 2008-07-15 Médicaments pour l'administration transdermique à des animaux

Country Status (14)

Country Link
US (1) US20100197791A1 (fr)
EP (1) EP2182921A2 (fr)
JP (1) JP2010534624A (fr)
AR (1) AR067561A1 (fr)
AU (1) AU2008280501A1 (fr)
BR (1) BRPI0814588A2 (fr)
CA (1) CA2694386A1 (fr)
CL (1) CL2008002077A1 (fr)
DE (1) DE102007034976A1 (fr)
PE (1) PE20090797A1 (fr)
TW (1) TW200922622A (fr)
UY (1) UY31227A1 (fr)
WO (1) WO2009012908A2 (fr)
ZA (1) ZA201000514B (fr)

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Also Published As

Publication number Publication date
PE20090797A1 (es) 2009-07-23
US20100197791A1 (en) 2010-08-05
CL2008002077A1 (es) 2009-01-30
CA2694386A1 (fr) 2009-01-29
UY31227A1 (es) 2009-03-02
AR067561A1 (es) 2009-10-14
DE102007034976A1 (de) 2009-01-29
WO2009012908A3 (fr) 2009-06-11
WO2009012908A2 (fr) 2009-01-29
JP2010534624A (ja) 2010-11-11
AU2008280501A1 (en) 2009-01-29
ZA201000514B (en) 2011-04-28
BRPI0814588A2 (pt) 2015-01-20
TW200922622A (en) 2009-06-01

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