HRP20211042T1 - Dugodjelujuće injektibilne formulacije koje sadrže antiparazitske izoksazolinske spojeve i njihove uporabe - Google Patents

Dugodjelujuće injektibilne formulacije koje sadrže antiparazitske izoksazolinske spojeve i njihove uporabe Download PDF

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Publication number
HRP20211042T1
HRP20211042T1 HRP20211042TT HRP20211042T HRP20211042T1 HR P20211042 T1 HRP20211042 T1 HR P20211042T1 HR P20211042T T HRP20211042T T HR P20211042TT HR P20211042 T HRP20211042 T HR P20211042T HR P20211042 T1 HRP20211042 T1 HR P20211042T1
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Croatia
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long
acting injectable
injectable preparation
preparation according
pharmaceutically acceptable
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HRP20211042TT
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English (en)
Inventor
Loic Patrick Le Hir De Fallois
Charles Q. Meng
Susan Mancini Cady
Peter CHEIFETZ
Izabela Galeska
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Boehringer Ingelheim Animal Health USA Inc.
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Publication of HRP20211042T1 publication Critical patent/HRP20211042T1/hr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A01N55/08—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing boron
    • 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
    • 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
    • A61K31/42—Oxazoles
    • 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
    • A61K31/42—Oxazoles
    • A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
    • 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
    • A61K31/69—Boron compounds
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • 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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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
    • A61K9/08—Solutions
    • 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
    • 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
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Dermatology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Dispersion Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Toxicology (AREA)
  • Fodder In General (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Claims (18)

1. Dugodjelujući injektibilni pripravak za liječenje ili prevenciju parazitne infekcije ili zaraze kod životinje, naznačen time, da navedeni pripravak sadrži: (a) učinkovitu količinu najmanje jedne antiparazitne aktivne tvari izoksazolina, koja je spoj formule (Ic): [image] ili njegova farmaceutski prihvatljiva sol; pri čemu svaki od X1, X2 i X3 je neovisno halogen, C1-C3 alkil ili C1-C3 haloalkil; (b) najmanje jedan farmaceutski prihvatljiv polimer koji je tekući PEG; (c) opcionalno, najmanje jedno kootapalo pri čemu je navedeno kootapalo polarno otapalo koje se može miješati s vodom; (d) opcionalno, antioksidant; i (e) opcionalno najmanje jedan farmaceutski prihvatljiv aditiv, pomoćno sredstvo ili njihove mješavine; pri čemu nisu prisutni nikakvi drugi farmaceutski prihvatljivi polimeri.
2. Dugodjelujući injektibilni pripravak prema patentnom zahtjevu 1, naznačen time, da X1 je Cl; X2 je F; i X3 je -CF3.
3. Dugodjelujući injektibilni pripravak prema patentnom zahtjevu 1, naznačen time, da se aktivna tvar izoksazolina obogaćuje u enantiomeru.
4. Dugodjelujući injektibilni pripravak prema patentnom zahtjevu 1, naznačen time, da aktivna tvar izoksazolina jest spoj formule (S)-Ic: [image] pri čemu su X1, X2 i X3 neovisno klor, fluor ili CF3; ili njegova farmaceutski prihvatljiva sol.
5. Dugodjelujući injektibilni pripravak prema bilo kojem od patentnih zahtjeva 1 do 4, naznačen time, da tekući PEG je PEG 200, PEG 300 ili PEG 400, ili njihova mješavina.
6. Dugodjelujući injektibilni pripravak prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time, da pripravak sadrži kootapalo, i protom je kootapalo etanol ili izopropanol, ili njihova mješavina.
7. Dugodjelujući injektibilni pripravak prema patentnom zahtjevu 1, naznačen time, da pripravak sadrži: a) 5 do 15% (m/v) izoksazolinskog spoja formule (Ic): [image] ili njegove farmaceutski prihvatljive soli; pri čemu svaki od X1, X2 i X3 neovisno je halogen, C1-C3 alkil ili C1-C3 haloalkil; b) farmaceutski prihvatljiv polimer koji je tekući PEG; c) opcionalno, 5% do 40% (m/v) kootapala, pri čemu se navedeno kootapalo bira od etanola i izopropanola; d) opcionalno, 0,01% do 2,0% (m/v) antioksidanta; i e) opcionalno, 0,01% do 5,0% (m/v) farmaceutski prihvatljivog aditiva, pomoćnog sredstva ili njihove mješavine; pri čemu jedini farmaceutski prihvatljiv polimer koji se nalazi u spomenutom dugodjelujućem injektibilnom pripravku jest tekući PEG i pritom se tekući PEG nalazi u cjelokupnom pripravku u takvom udjelu koji predstavlja nadopunu do 100% pripravka.
8. Dugodjelujući injektibilni pripravak prema bilo kojem od patentnih zahtjeva 1 do 7, naznačen time, da se paraziti liječe ili preveniraju u vremenu od tri do šest mjeseci.
9. Dugodjelujući injektibilni pripravak prema bilo kojem od patentnih zahtjeva 1 do 7, naznačen time, da se paraziti liječe ili preveniraju u vremenu od pet do šest mjeseci.
10. Dugodjelujući injektibilni pripravak prema bilo kojem od patentnih zahtjeva 1 do 7, naznačen time, da se paraziti liječe ili preveniraju u vremenu od šest mjeseci.
11. Dugodjelujući injektibilni pripravak prema bilo kojem od patentnih zahtjeva 8, 9 ili 10, naznačen time, da su paraziti buhe ili krpelji.
12. Dugodjelujući injektibilni pripravak prema bilo kojem od patentnih zahtjeva 1 do 11, naznačen time, da nadalje sadrži učinkovitu količinu najmanje jednog dodatnog aktivnog sredstva.
13. Dugodjelujući injektibilni pripravak prema patentnom zahtjevu 12, naznačen time, da dodatno farmaceutski aktivno sredstvo je makrociklički lakton, neonikotinoidno aktivno sredstvo, aktivna tvar 1-N-arilpirazol, ciklički depsipeptid, benzimidazol, imidazotiazol, aktivna tvar tetrahidropirimidin, aktivna tvar organofosfat, levamisol, aktivna tvar paraherkvamid, aktivna tvar markfortin, prazikvantel, klozantel, pirantel, morantel, klorsulon, aktivna tvar spinozin, aktivna tvar spinozoid, aktivna tvar amino acetonitril, aktivna tvar ariloazol-2-il cijanoetil ili regulator rasta kukaca.
14. Dugodjelujući injektibilni pripravak prema patentnom zahtjevu 13, naznačen time, da makrociklički lakton je abamektin, dimadektin, doramektin, emamektin, eprinomektin, ivermektin, latidektin, lepimektin, selamektin, ML-1,694,554, milbemektin, milbemicin D, moksidektin ili nemadektin.
15. Dugodjelujući injektibilni pripravak prema patentnom zahtjevu 1, naznačen time, da je za uporabu u liječenju ili prevenciji parazita kod životinja.
16. Dugodjelujući injektibilni pripravak za uporabu prema patentnom zahtjevu 15, naznačen time, da životinja je pas, mačka, ovca ili govedo.
17. Dugodjelujući injektibilni pripravak za uporabu prema patentnom zahtjevu 15, naznačen time, da se paraziti liječe ili preveniraju u vremenu od pet do šest mjeseci.
18. Dugodjelujući injektibilni pripravak za uporabu prema patentnom zahtjevu 15, naznačen time, da su paraziti buhe i/ili krpelji.
HRP20211042TT 2016-02-24 2021-06-30 Dugodjelujuće injektibilne formulacije koje sadrže antiparazitske izoksazolinske spojeve i njihove uporabe HRP20211042T1 (hr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201662299333P 2016-02-24 2016-02-24
US201662379348P 2016-08-25 2016-08-25
EP17709300.2A EP3419424B1 (en) 2016-02-24 2017-02-24 Long-acting injectable formulations comprising antiparasitic isoxazoline compounds and use thereof
PCT/US2017/019239 WO2017147352A1 (en) 2016-02-24 2017-02-24 Antiparasitic isoxazoline compounds, long-acting injectable formulations comprising them, methods and uses thereof

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HRP20211042T1 true HRP20211042T1 (hr) 2021-10-01

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US (2) US20170239218A1 (hr)
EP (2) EP3419424B1 (hr)
JP (2) JP7110106B2 (hr)
KR (1) KR20180113614A (hr)
CN (2) CN109068651B (hr)
AU (4) AU2017223828B2 (hr)
BR (1) BR112018017265B1 (hr)
CA (1) CA3015357A1 (hr)
CL (1) CL2018002402A1 (hr)
CO (1) CO2018008829A2 (hr)
CY (1) CY1124287T1 (hr)
DK (1) DK3419424T3 (hr)
EA (1) EA036716B1 (hr)
ES (1) ES2892078T3 (hr)
HK (1) HK1257959A1 (hr)
HR (1) HRP20211042T1 (hr)
HU (1) HUE054931T2 (hr)
IL (2) IL261197B (hr)
LT (1) LT3419424T (hr)
MX (2) MX2018010160A (hr)
NZ (1) NZ745859A (hr)
PL (1) PL3419424T3 (hr)
PT (1) PT3419424T (hr)
SG (2) SG11201806980TA (hr)
SI (1) SI3419424T1 (hr)
TW (3) TWI827503B (hr)
UY (1) UY37137A (hr)
WO (1) WO2017147352A1 (hr)
ZA (1) ZA201805476B (hr)

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UY37137A (es) 2016-02-24 2017-09-29 Merial Inc Compuestos antiparasitarios de isoxazolina, formulaciones inyectables de acción prolongada que los comprenden, métodos y usos de los mismos
JP7487864B2 (ja) * 2017-04-19 2024-05-21 三井化学クロップ＆ライフソリューション株式会社 木材保存用組成物及び木材保存処理方法
CN111295375A (zh) 2017-11-07 2020-06-16 英特维特国际股份有限公司 制备大尺寸异噁唑啉粒子的方法
PE20201150A1 (es) 2017-11-07 2020-10-26 Intervet Int Bv Composiciones farmaceuticas inyectables de isoxazolina y usos de las mismas
BR112020012018A2 (pt) 2017-12-15 2020-11-24 Tarsus Pharmaceuticals, Inc. formulações de parasiticida de isoxazolina e métodos para tratar blefarite
TWI812673B (zh) * 2018-02-12 2023-08-21 美商富曼西公司 用於防治無脊椎害蟲之萘異噁唑啉化合物
KR20220002890A (ko) 2019-03-19 2022-01-07 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 구충성 아자-벤조티오펜 및 아자-벤조푸란 화합물
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