EP2938361A1 - Pharmazeutische zusammensetzung mit einem derivat von n-phenylpyrazol und permethrin sowie verwendung bei der herstellung eines topischen tiermedizinischen medikaments - Google Patents

Pharmazeutische zusammensetzung mit einem derivat von n-phenylpyrazol und permethrin sowie verwendung bei der herstellung eines topischen tiermedizinischen medikaments

Info

Publication number
EP2938361A1
EP2938361A1 EP13826884.2A EP13826884A EP2938361A1 EP 2938361 A1 EP2938361 A1 EP 2938361A1 EP 13826884 A EP13826884 A EP 13826884A EP 2938361 A1 EP2938361 A1 EP 2938361A1
Authority
EP
European Patent Office
Prior art keywords
pharmaceutical composition
volume
weight
permethrin
topical veterinary
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Withdrawn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
EP13826884.2A
Other languages
English (en)
French (fr)
Inventor
Nathalie Delhom
Bertrand Havrileck
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.)
Virbac SA
Original Assignee
Virbac SA
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 Virbac SA filed Critical Virbac SA
Publication of EP2938361A1 publication Critical patent/EP2938361A1/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Withdrawn legal-status Critical Current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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/222—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having aromatic groups, e.g. dipivefrine, ibopamine
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides

Definitions

  • the present invention relates to a topical veterinary pharmaceutical composition combining N-phenylpyrazole, preferably fipronil, and an ectoparasiticidal agent, especially permethrin, for the treatment of infestations by external parasites (flea, tick, mosquito, sandfly, sarcopter). .
  • Pets are often infested with one or more parasites feeding on blood such as dog fleas, cat fleas, ticks, or sarcoptes (responsible for scabies).
  • Fleas are wingless insects, with laterally compressed bodies and highly developed legs, suitable for jumping. They are ectoparasites, sucking blood from mammals or birds. The 2000 listed species belong to the order of siphonaptera. Two species of fleas are commonly found in Europe; it is the cat's flea (Ctenocephalides felis) and the flea (Ctenocephalides canis) that live in the fur of animals.
  • Flea bites cause itching in both animals and humans.
  • the saliva of the flea secreted with each bite) can also, according to individuals, cause allergic reactions, immediate or delayed. These reactions result in various skin and itchy lesions.
  • Flea Allergy Dermatitis (DAPP) is the most common cause of pruritus in dogs. In France, in adult dogs, it accounts for almost half of the pruriginous dermatoses.
  • the carnivore becomes infested by swallowing parasitic fleas. This infestation can cause anal pruritus, engorgement of anal sacs, and perineal dermatitis. Therefore, it is sometimes advisable to worm regularly the animals in addition to the fight against fleas.
  • ticks (Rhipicephalus sp., Ixodes sp., Dermacentor sp., Amblyomma sp., ...) can also cause stress to the animal and harm its health. They can also harm the man. But the most serious problem of ticks is that they are a vector of pathogens that can affect the animal as much as the man. Major diseases to be avoided include Borellioses (Lyme disease Borellia burgdorferi), Babesioses (Babesia sp. Piroplasmosis), and Rickettsioses. Ticks can also release toxins with crippling, inflammatory, and sometimes life-threatening properties.
  • the gall (Demodex sp., Sarcoptes sp., Otodectes sp., ...) is particularly difficult to fight because there are very few effective active ingredients; it requires frequent treatments.
  • Mosquitoes (Culex sp., Aedes sp., Anopheles sp., ...) play an extremely important role in human or animal health because they concentrate, beyond their role of nuisance by the bites they inflict, the the most important group of vectors of pathogens transmissible to humans, including many zoonoses. They are vectors of three groups of pathogens for humans: Plasmodium, filarial as well as many arboviruses. They are present on all the Earth's land surface (except Antarctica), both in forest, savannah and urban environments, as soon as a surface of fresh or brackish water, even if reduced or temporary, is available. Sixty-five species are referenced in metropolitan France.
  • Phlebotomine (Phlebotomus sp., ...) are blood-sucking insects.
  • the sandfly is an insect vector. If infected, its sting transmits leishmaniasis.
  • N-phenylpyrazole and permethrin derivatives have been known for a long time because the overlap and the complementarity of the action spectra of the active ingredients make them particularly interesting in the fight against pests in agriculture and in the veterinary field where each of the active ingredients is commonly used.
  • the Applicant has found that permethrin changes phase at low temperature, that is to say crystallizes when it is formulated in high concentration with another active ingredient in an excipient or a mixture of excipients according to the invention.
  • Prior art preservation tests at 8 ° C carried out on formulations combining between 51 and 75% w / v of permethrin and between 0 and 10% w / v of fipronil in the diethylene glycol monoethyl ether show a systematic phase change of the formulation (appearance of crystals at the latest after 5 days of storage) as long as the permethrin content exceeds 65% by weight / volume; the increase in the fipronil content in the formulation lowers this permethrin concentration threshold from which it changes phase.
  • the aim of the Applicant is to provide a product for the prevention and treatment of flea infestations in domestic animals which has a broad spectrum of action, which is easy to administer, while having a rapid action and persistent.
  • Another objective of the invention is the development of stable compositions whose storage does not require any particular precaution (such as, for example, the maintenance of the product at a temperature above 20 ° C.).
  • N-phenylpyrazoles are a large family of compounds with a very wide spectrum of activity, including antiparasitic activities; they are described in patent applications EP 0 295 117 and EP 0 352 944.
  • composition combining an N-arylpyrazole and a pyrethroid in a self-spreading formulation (“self-spreading") that does not pose any risk of use and in which it there is no observed decrease in the effect of N-arylpyrazole due to the addition of other active (s).
  • the formulation developed within the scope of this invention comprises, in addition to the active ones, an aliphatic cyclic carbonate (ethylene or propylene carbonate) and an aliphatic, cyclic or acyclic polyether (in particular, diethylene glycol monoethyl ether); it is preferably topical for spot-on administration.
  • This application makes no mention of the problem of crystallization of the active ingredients, it should however be noted that no example of composition comprises a permethrin content greater than 45 g / 100 ml.
  • N-phenylpyrazole especially, fipronil
  • an inhibitor of the crystallization of the product when it is applied to the hair of the animal is preferably a combination of a surfactant (Polysorbate 80) and a film-forming agent (PVP, polyvinyl alcohol and copolymers of vinyl acetate and vinylpyrrolidone);
  • a surfactant Polysorbate 80
  • a film-forming agent PVP, polyvinyl alcohol and copolymers of vinyl acetate and vinylpyrrolidone
  • the problem of the crystallization addressed in this application aims to prevent solid particles of formulation being visible on the fur of the animal; it is therefore a problem different from that proposed by the present invention, that is to say, avoid crystallization of the product in its packaging.
  • Patent Application EP 1 372 622 states that it is advantageous to formulate compositions with a high content of pyrethroids, in particular permethrin, but it also teaches that the compositions tend to crystallize at low temperature and when the pyrethroid is present in high concentration (such as levels greater than 50% or 65% volume / volume). It proposes a pyrethroid-based formulation comprising a terpene or a terpene derivative or a mixture of an alkylglycolether with a terpene or a terpene derivative, as an excipient to avoid or minimize crystallization of the pyrethroid at low temperatures. temperature.
  • the present invention relates to a topical veterinary pharmaceutical composition consisting of (in what follows and unless otherwise indicated, the ranges of percentage are expressed by weight relative to the total volume of the composition):
  • N-phenylpyrazole preferably, 5-amino-1- [2,6-dichloro-4- (trifluoromethyl) phenyl] -4- (trifluoromethylsulfinyl) -1H-pyrazole-3-carbonitrile (fipronil);
  • a pyrethroid preferably permethrin
  • phase change inhibitor selected from ethanol, benzyl alcohol and mixtures thereof;
  • one or more other active agents in a total amount not exceeding 10% w / v;
  • an organic solvent chosen from propylene glycol monomethyl ether, dipropylene glycol n-butyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, and propylene glycol, and mixtures thereof.
  • composition means that, according to a particular embodiment of the invention, the composition does not include other ingredients than those explicitly mentioned.
  • the composition comprises an amount of pyrethroid of between 52% and 70% by weight / volume, between 52% and 67% by weight / volume, between 53% and 70% by weight. volume, between 53% and 67% w / v, between 54% and 70% w / v, between 54% and 67% w / v, 52% to 58% w / v, 53% to 57% w / v, 54% to 55% w / v, and 54.5% w / v.
  • the pyrethroid is permethrin.
  • the composition comprises between 6 and 7% w / v of an N-phenylpyrazole, preferably imipril, and, in order of preference, between 52% and 70% by weight. weight / volume, between 52% and 67% w / v, between 53% and 70% w / v, between 53% and 67% w / v, between 54% and 70% w / v, between 54% and 70% w / v, % and 67% w / v, between 52 and 58% w / v, between 53% and 57% w / v, between 54% and 55% w / v and 54.5% w / v pyrethroid, preferably permethrin.
  • diethylene glycol monoethyl ether is very particularly preferred.
  • the antioxidants are advantageously chosen from ethyl or propyl gallate, ⁇ -tocopherol, ascorbic acid, ascorbyl palmitate, monothioglycerol, butylated hydroxytoluene (BHT) and butylated hydroxyanisole (BHA); preferably, BHT or a mixture of BHT and BHA will be used as the antioxidant.
  • the antioxidant agent (s) preferably represent from 0.005 to 2% by weight / volume approximately, and still more preferably from 0.01 to 0.1% by weight. volume.
  • composition according to the invention consists of:
  • N-phenylpyrazole preferably, 5-amino-1- [2,6-dichloro-4- (trifluoromethyl) phenyl] -4-
  • phase change inhibitor selected from ethanol, benzyl alcohol and mixtures thereof;
  • composition according to the invention consists of:
  • N-phenylpyrazole preferably, 5-amino-1- [2,6-dichloro-4- (trifluoromethyl) phenyl] -4- (trifluoromethylsulfinyl) -1H-pyrazole-3-carbonitrile (fipronil);
  • phase change inhibitor selected from ethanol, benzyl alcohol and mixtures thereof;
  • composition according to the invention consists of:
  • Monoethylether of diethylene glycol qs 100 ml (composition expressed as a percentage by weight relative to the total volume of the composition).
  • compositions according to the invention which are active against blood-sucking parasites, and in particular against fleas, may in particular be in the form of liquid compositions or skin solutions for deposition or else "spot-on", to be applied very easily, at one time, in one or more points topically directly on the skin of the animal, usually between the shoulder blades.
  • the liquid compositions are then packaged in containers for the assay of said compositions and whose volume is less than or equal to 10 ml, and preferably between 0.1 to 10 ml and more preferably between 0.3 to 10 ml.
  • compositions according to the invention may advantageously comprise, in order to broaden or complete the action spectra of the active agents already present in the compositions according to the invention, one or more additional active agents, at the provided that the total content of this or these additional ingredients does not exceed 10% by weight relative to the total volume of the composition and preferably does not exceed 5% and even more preferably 3% by weight relative to the total volume of the composition. composition.
  • These additional active agents are preferably chosen from endoparasiticides and ectoparasiticides.
  • isoxazolines macrocyclic lactones, neo-nicotinoids, and insect growth regulators. Mention may in particular be made of compounds which mimic juvenile hormones, in particular azadirachtin, diofenolan, fenoxycarb, hydroprene, kinoprene, methoprene, pyriproxyfene, tetrahydroazadirachtin, or inhibitors of chitin synthesis, in particular chlorfluazuron, novaluron, cyromazine, diflubenzuron, fluazuron, flucycloxuron, lufenuron, teflubenzuron.
  • Pyriproxyfene is particularly preferred, in an amount of between 1 and 10% by weight relative to the total volume of the composition, preferably between 1 and 5% by weight relative to the total volume of the composition and even more preferably at 2% by weight relative to the total volume of the composition. weight relative to the total volume of the composition.
  • composition according to the invention consists of:
  • the pharmaceutical composition according to the invention is preferably packaged in single dose pipettes.
  • the pipettes may consist of one or more films whose constituent material may be chosen from polypropylene (PP), polyvinyl chloride (PVC), polyvinylidene chloride, cycloolefin copolymer (COC), polychlorinated trifluoroethylene (PCTFE) ), or their derivatives, alone or in mixtures.
  • the film is Polybar TM sold by Alcan Packaging TM, which consists of a copolymer cycloolefin (COC) film coextruded between two layers of polypropylene (PP). The Polybar is then laminated or laminated with a Barex TM film.
  • PET polyethylene terephthalate
  • BP Chemicals TM polyacrylonitrile marketed by BP Chemicals TM under the brand name Barex TM, or derivatives thereof, taken alone or in combination.
  • the volume of the composition according to the invention contained in the pipettes may be 0.44 ml; 1.1 ml; 2.2 ml; 4.4 ml; 6.6 ml.
  • the volume may be between 0.1 and 10 ml, preferably between 0.3 and 6.6 ml and even more preferably between 0.44 and 6.6 ml.
  • Another subject of the present application relates to a liquid pharmaceutical composition as described above as a topical veterinary pest control drug for use in the prevention (protection) and / or treatment of infestations by external parasites, such as fleas, ticks, mosquitoes, sandflies and sarcoptes, in domestic animals, especially dogs (so-called "spot-on” application).
  • external parasites such as fleas, ticks, mosquitoes, sandflies and sarcoptes
  • said medicament is intended to be applied by direct application to the skin of the animal, at the level of the shoulder blades or on a dorsal line extending from the base of the tail up to the neck.
  • the amount of drug to be administered may vary from about 0.3 to 6.6 ml in the dog, depending on the weight of the animal and the dosage to be adapted according to the frequency of treatment.
  • the invention also comprises other arrangements which will emerge from the description which follows, which refers to an example of the preparation of a pharmaceutical composition according to the invention, as well as than examples highlighting the stability of said composition during its conservation.
  • the objective of the developments is the development of a formulation such that the assets do not crystallize during storage, despite a high concentration of active ingredients, in particular, permethrin.
  • BHT butylhydroxytoluene
  • BHA butylhydroxyanisole
  • compositions detailed in Tables I, II and III below were stored in 10 ml clear and colorless glass vials at 8 ° C.
  • BHT Butylhydroxytoluene
  • BHT Butylhydroxytoluene
  • BHT Butylhydroxytoluene

Landscapes

  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (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)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Zoology (AREA)
  • Dermatology (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Emergency Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
EP13826884.2A 2012-12-27 2013-12-20 Pharmazeutische zusammensetzung mit einem derivat von n-phenylpyrazol und permethrin sowie verwendung bei der herstellung eines topischen tiermedizinischen medikaments Withdrawn EP2938361A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1262822A FR3000393B1 (fr) 2012-12-27 2012-12-27 Association topique d'un n-phenylpyrazole et de permethrine
PCT/IB2013/061218 WO2014102693A1 (fr) 2012-12-27 2013-12-20 Composition pharmaceutique contenant un derive de n-phenylpyrazole et de permethrine, utilisation pour la preparation d'un medicament veterinaire topique

Publications (1)

Publication Number Publication Date
EP2938361A1 true EP2938361A1 (de) 2015-11-04

Family

ID=48224910

Family Applications (1)

Application Number Title Priority Date Filing Date
EP13826884.2A Withdrawn EP2938361A1 (de) 2012-12-27 2013-12-20 Pharmazeutische zusammensetzung mit einem derivat von n-phenylpyrazol und permethrin sowie verwendung bei der herstellung eines topischen tiermedizinischen medikaments

Country Status (5)

Country Link
EP (1) EP2938361A1 (de)
AU (1) AU2013368970A1 (de)
BR (1) BR112015015493B1 (de)
FR (1) FR3000393B1 (de)
WO (1) WO2014102693A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9392792B1 (en) * 2014-12-30 2016-07-19 Virbac Topical combination of fipronil, permethrin and pyriproxyfen

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8713768D0 (en) 1987-06-12 1987-07-15 May & Baker Ltd Compositions of matter
GB8816915D0 (en) 1988-07-15 1988-08-17 May & Baker Ltd New compositions of matter
FR2739255B1 (fr) * 1995-09-29 1998-09-04 Rhone Merieux Composition antiparasitaire pour le traitement et la protection des animaux de compagnie
US6660768B2 (en) * 2001-02-08 2003-12-09 Schering-Plough Animal Health Corporation Parasiticidal compositions and methods of use
DE102006061538A1 (de) * 2006-12-27 2008-07-03 Bayer Healthcare Ag Kombinationsprodukt zur Bekämpfung von Parasiten an Tieren
EP2187740B1 (de) 2007-09-06 2015-11-04 The Hartz Mountain Corporation Verfahren zu bekämpfung von tierparasiten mittels insektenwachstumsregulatoren
EP2567618B1 (de) * 2008-12-16 2017-05-03 Virbac Pharmazeutische Zusammensetzung, die ein N-Phenylpyrazol-Derivat umfasst, und deren Verwendung für die Herstellung eines lokalen Veterinärmedikaments zur Bekämpfung von Flöhen
BR112012006514A2 (pt) 2009-09-22 2015-09-08 Sergeants Pet Care Prod Inc composição de pesticida spot-on

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
None *
See also references of WO2014102693A1 *

Also Published As

Publication number Publication date
BR112015015493A2 (pt) 2017-07-11
FR3000393A1 (fr) 2014-07-04
AU2013368970A1 (en) 2015-07-16
FR3000393B1 (fr) 2015-01-16
BR112015015493A8 (pt) 2019-10-22
BR112015015493B1 (pt) 2020-11-24
WO2014102693A1 (fr) 2014-07-03

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