RU2016129474A - Изоксазолиновые композиции - Google Patents
Изоксазолиновые композиции Download PDFInfo
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- RU2016129474A RU2016129474A RU2016129474A RU2016129474A RU2016129474A RU 2016129474 A RU2016129474 A RU 2016129474A RU 2016129474 A RU2016129474 A RU 2016129474A RU 2016129474 A RU2016129474 A RU 2016129474A RU 2016129474 A RU2016129474 A RU 2016129474A
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- 239000000203 mixture Substances 0.000 title claims 3
- -1 isoxazoline compound Chemical class 0.000 claims 19
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 241001465754 Metazoa Species 0.000 claims 5
- 239000003651 drinking water Substances 0.000 claims 5
- 235000020188 drinking water Nutrition 0.000 claims 5
- 230000001225 therapeutic effect Effects 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- 206010061217 Infestation Diseases 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 230000003071 parasitic effect Effects 0.000 claims 3
- 229920000136 polysorbate Polymers 0.000 claims 3
- 229950008882 polysorbate Drugs 0.000 claims 3
- 239000004094 surface-active agent Substances 0.000 claims 3
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims 2
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims 2
- MLBZKOGAMRTSKP-UHFFFAOYSA-N fluralaner Chemical compound C1=C(C(=O)NCC(=O)NCC(F)(F)F)C(C)=CC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=C1 MLBZKOGAMRTSKP-UHFFFAOYSA-N 0.000 claims 2
- 229960004498 fluralaner Drugs 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims 2
- 241000894007 species Species 0.000 claims 2
- 201000001064 tick infestation Diseases 0.000 claims 2
- 241001481694 Dermanyssus Species 0.000 claims 1
- 241000273340 Ornithonyssus Species 0.000 claims 1
- 241000282887 Suidae Species 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229940116333 ethyl lactate Drugs 0.000 claims 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims 1
- 125000004969 haloethyl group Chemical group 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 230000009545 invasion Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims 1
- 229920000053 polysorbate 80 Polymers 0.000 claims 1
- 229940068968 polysorbate 80 Drugs 0.000 claims 1
- 244000144977 poultry Species 0.000 claims 1
- 125000004673 propylcarbonyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
Classifications
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- 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
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- 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
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/105—Aliphatic or alicyclic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/30—Feeding-stuffs specially adapted for particular animals for swines
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
- A23K50/75—Feeding-stuffs specially adapted for particular animals for birds for poultry
-
- 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
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- 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
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- 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
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
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- 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
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- 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
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Zoology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Food Science & Technology (AREA)
- Animal Husbandry (AREA)
- Birds (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Toxicology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Claims (31)
1. Применение фармацевтической композиции, содержащей изоксазолиновое соединение формулы (I),
в которой
R1 = галоген, CF3, OCF3, CN,
n = целое число от 0 до 3, предпочтительно 1, 2 или 3,
R2 = С1-С3-галогеналкил, предпочтительно CF3 или CF2Cl,
Т = 5- или 6-членное кольцо, которое необязательно замещено одним или несколькими радикалами Y,
Y = метил, галогенметил, галоген, CN, NO2, NH2-C=S, или два смежных радикала Y вместе образуют цепь, главным образом трех- или четырехчленную цепь;
Q = X-NR3R4 или 5-членное N-гетероарильное кольцо, которое необязательно замещено одним или несколькими радикалами;
Х = СН2, СН(СН3), СН(CN), CO, CS,
R3 = водород, метил, галогенэтил, галогенпропил, галогенбутил, метоксиметил, метоксиэтил, галогенметоксиметил, этоксиметил, галогенэтоксиметил, пропоксиметил, этиламинокарбонилметил, этиламинокарбонилэтил, диметоксиэтил, пропиниламинокарбонилметил, N-фенил-N-метил-амино, галогенэтиламинокарбонилметил, галогенэтиламинокарбонилэтил, тетрагидрофурил, метиламинокарбонилметил, (N,N-диметиламино)-карбонилметил, пропиламинокарбонилметил, циклопропиламинокарбонилметил, пропениламинокарбонилметил, галогенэтиламинокарбонилциклопропил,
где ZA = водород, галоген, циано, галогенметил (CF3);
R4 = водород, этил, метоксиметил, галогенметоксиметил, этоксиметил, галогенэтоксиметил, пропоксиметил, метилкарбонил, этилкарбонил, пропилкарбонил, циклопропилкарбонил, метоксикарбонил, метоксиметилкарбонил, аминокарбонил, этиламинокарбонилметил, этиламинокарбонилэтил, диметоксиэтил, пропиниламинокарбонилметил, галогенэтиламинокарбонилметил, цианометиламинокарбонилметил или галогенэтиламинокарбонилэтил;
или R3 и R4 вместе образуют заместитель, выбранный из группы, состоящей из:
или его соль, или его сольват и фармацевтически приемлемый носитель, содержащий моноэтиловый эфир диэтиленгликоля и полисорбатное поверхностно-активное вещество для получения лекарственного средства для введения через питьевую воду для профилактики или лечения паразитарных инвазий животных.
2. Применение по п.1, где изоксазолиновое соединение представляет собой флураланер.
3. Применение по п.2, включающее от 1,5 мг/мл до 100 мг/мл флураланера.
4. Применение по любому из пп.1-4, где соотношение моноэтилового эфира диэтиленгликоля и полисорбатного поверхностно-активного вещества составляет <50:50% масс./масс., предпочтительно 25/75% масс./масс.
5. Применение по любому из пп. 1-4, где композиция дополнительно содержит этиллактат.
6. Применение по любому из пп. 1-5, где полисорбатное поверхностно-активное вещество представляет собой полисорбат 80.
7. Фармацевтическая композиция, как определено по любому из пп. 1-6, для применения в профилактике или лечении паразитарных инвазий у животных после введения животным через питьевую воду.
8. Фармацевтическая композиция по п. 7, где животных выбирают из свиней и домашней птицы.
9. Фармацевтическая композиция по п. 8, где животные представляют собой кур-несушек.
10. Фармацевтическая композиция по любому из пп. 7-9, где паразитарная инвазия представляет собой инвазию клещом.
11. Фармацевтическая композиция по п. 11, где инвазия клещом представляет собой инвазию видом Dermanyssus или видом Ornithonyssus.
12. Лечебная питьевая вода, содержащая смесь фармацевтической композиции, как определено по пп. 1-6, и воды.
13. Лечебная питьевая вода по п. 12, содержащая от 0,001 до 1 мг/мл изоксазолинового соединения, как определено по п. 1 или 2.
14. Лечебная вода по п. 12 или 13 для применения по любому из пп. 7-11.
15. Способ получения лечебной питьевой воды по п. 12 или 13, в котором фармацевтическую композицию разбавляют путем впрыскивания через систему дозирующего насоса в систему водоснабжения или путем смешивания с водой в резервуаре для лекарственных средств.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13199006.1 | 2013-12-20 | ||
| EP13199006 | 2013-12-20 | ||
| PCT/EP2014/078634 WO2015091898A1 (en) | 2013-12-20 | 2014-12-19 | Isoxazoline compositions and use thereof in the prevention or treatment of parasite infestations in animals |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2019114223A Division RU2791637C2 (ru) | 2013-12-20 | 2014-12-19 | Изоксазолиновые композиции и их применение в профилактике или лечении паразитарных инвазий животных |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2016129474A true RU2016129474A (ru) | 2018-01-25 |
| RU2688919C1 RU2688919C1 (ru) | 2019-05-23 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2016129474A RU2688919C1 (ru) | 2013-12-20 | 2014-12-19 | Изоксазолиновые композиции и их применение в провилактике или лечении паразитарных инвазий животных |
Country Status (11)
| Country | Link |
|---|---|
| US (4) | US10456358B2 (ru) |
| EP (2) | EP4306168B1 (ru) |
| JP (1) | JP6581586B2 (ru) |
| CN (2) | CN105813651B (ru) |
| ES (2) | ES3036365T3 (ru) |
| HU (1) | HUE066811T2 (ru) |
| MX (1) | MX373872B (ru) |
| PL (2) | PL3082867T3 (ru) |
| PT (1) | PT4306168T (ru) |
| RU (1) | RU2688919C1 (ru) |
| WO (1) | WO2015091898A1 (ru) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015091898A1 (en) | 2013-12-20 | 2015-06-25 | Intervet International B.V. | Isoxazoline compositions and use thereof in the prevention or treatment of parasite infestations in animals |
| WO2016022066A1 (en) | 2014-08-04 | 2016-02-11 | Jerry Tan Eye Surgery Pte Ltd | Pharmaceutical compositions for demodex related blepharitis and eyelid crusting |
| PL3236960T3 (pl) * | 2014-12-22 | 2025-07-07 | Intervet International B.V. | Fluralaner do zastosowania w leczeniu demodekozy |
| BR112017027855B1 (pt) | 2015-06-23 | 2022-11-16 | Intervet International B.V. | Composição farmacêutica, seu uso, água potável medicamentosa e método para sua preparação |
| WO2018039508A1 (en) * | 2016-08-25 | 2018-03-01 | Merial, Inc. | Method for reducing unwanted effects in parasiticidal treatments |
| KR20190091268A (ko) * | 2016-10-31 | 2019-08-05 | 더 스크립스 리서치 인스티튜트 | 매개체 전파 질환의 전염을 예방하기 위한 방법 및 조성물 |
| AU2018363686B2 (en) * | 2017-11-07 | 2023-11-23 | Intervet International B.V. | Process for preparing large size isoxazoline particles |
| PE20201150A1 (es) * | 2017-11-07 | 2020-10-26 | Intervet Int Bv | Composiciones farmaceuticas inyectables de isoxazolina y usos de las mismas |
| KR20250065422A (ko) | 2017-12-15 | 2025-05-12 | 타르서스 파마수티칼스, 아이엔씨. | 안검염을 치료하기 위한 이속사졸린 구충제 제제 및 방법 |
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| JP2016540809A (ja) | 2016-12-28 |
| US20210353537A1 (en) | 2021-11-18 |
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| ES2971061T3 (es) | 2024-06-03 |
| MX2016008118A (es) | 2016-09-16 |
| US20200000720A1 (en) | 2020-01-02 |
| RU2019114223A (ru) | 2019-06-28 |
| CN105813651A (zh) | 2016-07-27 |
| PL3082867T3 (pl) | 2024-05-13 |
| CN110327468A (zh) | 2019-10-15 |
| PL4306168T3 (pl) | 2025-11-17 |
| EP3082867A1 (en) | 2016-10-26 |
| US20240122849A1 (en) | 2024-04-18 |
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| RU2688919C1 (ru) | 2019-05-23 |
| EP4306168B1 (en) | 2025-06-25 |
| EP4306168A2 (en) | 2024-01-17 |
| CN110327468B (zh) | 2023-04-28 |
| JP6581586B2 (ja) | 2019-09-25 |
| US20160317439A1 (en) | 2016-11-03 |
| ES3036365T3 (en) | 2025-09-18 |
| US11883530B2 (en) | 2024-01-30 |
| CN105813651B (zh) | 2021-11-23 |
| US10456358B2 (en) | 2019-10-29 |
| MX373872B (es) | 2020-03-26 |
| PT4306168T (pt) | 2025-07-24 |
| EP3082867B1 (en) | 2024-01-17 |
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