ES2905848T3 - Compuestos de isoxazolina antiparasitarios y plaguicidas - Google Patents
Compuestos de isoxazolina antiparasitarios y plaguicidas Download PDFInfo
- Publication number
- ES2905848T3 ES2905848T3 ES14803270T ES14803270T ES2905848T3 ES 2905848 T3 ES2905848 T3 ES 2905848T3 ES 14803270 T ES14803270 T ES 14803270T ES 14803270 T ES14803270 T ES 14803270T ES 2905848 T3 ES2905848 T3 ES 2905848T3
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- ES
- Spain
- Prior art keywords
- alkyl
- haloalkyl
- hydrogen
- halogen
- independently
- 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.)
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- 150000002547 isoxazolines Chemical class 0.000 title description 18
- 239000000575 pesticide Substances 0.000 title description 5
- 230000002141 anti-parasite Effects 0.000 title description 3
- 239000003096 antiparasitic agent Substances 0.000 title description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 623
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 623
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 364
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 328
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 320
- 150000002367 halogens Chemical class 0.000 claims abstract description 320
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 275
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 268
- 150000001721 carbon Chemical group 0.000 claims abstract description 266
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 229
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 226
- -1 Isoxazoline compound Chemical class 0.000 claims abstract description 164
- 125000004001 thioalkyl group Chemical group 0.000 claims abstract description 121
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 113
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 96
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 94
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 85
- 125000000232 haloalkynyl group Chemical group 0.000 claims abstract description 85
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 72
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 51
- 125000003118 aryl group Chemical group 0.000 claims abstract description 50
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 50
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 49
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 49
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 46
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 46
- 125000004995 haloalkylthio group Chemical group 0.000 claims abstract description 46
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 43
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 43
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 36
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 31
- 125000004992 haloalkylamino group Chemical group 0.000 claims abstract description 28
- SHENXRCDBJGWNU-GOSISDBHSA-N 6-(1,3-benzothiazol-6-ylamino)-4-(cyclopropylamino)-n-[(2r)-2-fluoro-3-hydroxy-3-methylbutyl]pyridine-3-carboxamide Chemical compound CC(C)(O)[C@H](F)CNC(=O)C1=CN=C(NC=2C=C3SC=NC3=CC=2)C=C1NC1CC1 SHENXRCDBJGWNU-GOSISDBHSA-N 0.000 claims abstract description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 17
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 14
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims abstract description 13
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 229910052717 sulfur Chemical group 0.000 claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 6
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 5
- 239000011593 sulfur Chemical group 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical group 0.000 claims abstract 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 268
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 234
- 229910052721 tungsten Inorganic materials 0.000 claims description 162
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 115
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 105
- 239000000460 chlorine Substances 0.000 claims description 105
- 229910052801 chlorine Inorganic materials 0.000 claims description 105
- 229910052731 fluorine Inorganic materials 0.000 claims description 104
- 239000011737 fluorine Substances 0.000 claims description 104
- 125000001624 naphthyl group Chemical group 0.000 claims description 87
- 239000000203 mixture Substances 0.000 claims description 53
- 241001465754 Metazoa Species 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 26
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 26
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 26
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 26
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 26
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 26
- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 23
- 125000006344 nonafluoro n-butyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 23
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 241000607479 Yersinia pestis Species 0.000 claims description 15
- 206010061217 Infestation Diseases 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 239000002023 wood Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- 208000030852 Parasitic disease Diseases 0.000 claims description 6
- 230000003071 parasitic effect Effects 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 102
- 150000001875 compounds Chemical class 0.000 description 83
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 32
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 32
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 24
- 125000004093 cyano group Chemical group *C#N 0.000 description 23
- 241000196324 Embryophyta Species 0.000 description 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 19
- 238000009472 formulation Methods 0.000 description 19
- 150000003839 salts Chemical group 0.000 description 14
- 239000004094 surface-active agent Substances 0.000 description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 230000000361 pesticidal effect Effects 0.000 description 10
- 241000238876 Acari Species 0.000 description 9
- 239000004530 micro-emulsion Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 244000045947 parasite Species 0.000 description 9
- 230000000590 parasiticidal effect Effects 0.000 description 9
- 239000006072 paste Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 230000006378 damage Effects 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000003755 preservative agent Substances 0.000 description 8
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- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000003086 colorant Substances 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 239000004540 pour-on Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical group CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 6
- 241000283690 Bos taurus Species 0.000 description 5
- 241000282412 Homo Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- 235000013355 food flavoring agent Nutrition 0.000 description 5
- 150000002334 glycols Chemical class 0.000 description 5
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 241000271566 Aves Species 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 235000019483 Peanut oil Nutrition 0.000 description 4
- 241000238680 Rhipicephalus microplus Species 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 201000008680 babesiosis Diseases 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 4
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 244000078703 ectoparasite Species 0.000 description 4
- 235000003599 food sweetener Nutrition 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
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- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- 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
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
-
- 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
- C07D413/10—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 linked by a carbon chain containing aromatic rings
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Dispersion Chemistry (AREA)
- Toxicology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361898578P | 2013-11-01 | 2013-11-01 | |
| PCT/US2014/063074 WO2015066277A1 (en) | 2013-11-01 | 2014-10-30 | Antiparisitic and pesticidal isoxazoline compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2905848T3 true ES2905848T3 (es) | 2022-04-12 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14803270T Active ES2905848T3 (es) | 2013-11-01 | 2014-10-30 | Compuestos de isoxazolina antiparasitarios y plaguicidas |
Country Status (22)
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|---|---|
| US (1) | US9447084B2 (https=) |
| EP (2) | EP3733664A1 (https=) |
| JP (2) | JP6484641B2 (https=) |
| KR (1) | KR102341193B1 (https=) |
| CN (1) | CN105873925B (https=) |
| AP (1) | AP2016009184A0 (https=) |
| AR (1) | AR098266A1 (https=) |
| AU (2) | AU2014342241B2 (https=) |
| CA (1) | CA2929234C (https=) |
| CL (1) | CL2016001043A1 (https=) |
| DK (1) | DK3063144T3 (https=) |
| EA (1) | EA030935B1 (https=) |
| ES (1) | ES2905848T3 (https=) |
| IL (1) | IL245384B (https=) |
| MX (1) | MX361516B (https=) |
| NZ (1) | NZ719916A (https=) |
| PL (1) | PL3063144T3 (https=) |
| PT (1) | PT3063144T (https=) |
| SG (1) | SG11201603430XA (https=) |
| TW (1) | TWI658040B (https=) |
| UY (1) | UY35810A (https=) |
| WO (1) | WO2015066277A1 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LT3298027T (lt) | 2015-05-20 | 2021-08-10 | Boehringer Ingelheim Animal Health USA Inc. | Antihelmintiniai depsipeptido junginiai |
| BR112017027855B1 (pt) | 2015-06-23 | 2022-11-16 | Intervet International B.V. | Composição farmacêutica, seu uso, água potável medicamentosa e método para sua preparação |
| 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 |
| CA3044038A1 (en) | 2016-11-16 | 2018-05-24 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic depsipeptide compounds |
| WO2018192793A1 (en) * | 2017-04-20 | 2018-10-25 | Basf Se | Substituted rhodanine derivatives |
| AR113997A1 (es) | 2017-12-21 | 2020-07-08 | Intervet Int Bv | Composiciones antiparasitarias para unción dorsal continua |
| CN110305033B (zh) * | 2018-03-20 | 2020-08-28 | 鲁南制药集团股份有限公司 | 一种西司他汀钠中间体的纯化方法 |
| AU2019301510B2 (en) | 2018-07-09 | 2024-06-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Anthelminthic heterocyclic compounds |
| CA3133100A1 (en) | 2019-03-19 | 2020-09-24 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic aza-benzothiophene and aza-benzofuran compounds |
| EP4077286A1 (en) | 2019-12-18 | 2022-10-26 | Elanco Tiergesundheit AG | Isoxazoline derivatives as pesticides |
| KR20230028268A (ko) | 2020-05-29 | 2023-02-28 | 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 | 구충성 헤테로시클릭 화합물 |
| JP7824305B2 (ja) | 2021-01-27 | 2026-03-04 | コルテバ アグリサイエンス エルエルシー | 魚における寄生生物に対するシクロプロピルアミド化合物 |
| US20240116854A1 (en) | 2021-01-27 | 2024-04-11 | Intervet Inc. | Cyclopropylamide compounds against parasites in fish |
| KR20230145066A (ko) * | 2021-02-11 | 2023-10-17 | 바스프 에스이 | 치환된 이속사졸린 유도체 |
| EP4043444A1 (en) * | 2021-02-11 | 2022-08-17 | Basf Se | Substituted isoxazoline derivatives |
| CN116888101A (zh) * | 2021-02-11 | 2023-10-13 | 巴斯夫欧洲公司 | 取代的异噁唑啉衍生物 |
| UY39995A (es) | 2021-11-01 | 2023-05-15 | Boehringer Ingelheim Vetmedica GmbH | Compuestos de pirrolopiridazina como antihelmínticos |
| CN116102511A (zh) * | 2023-02-10 | 2023-05-12 | 河北圣雪大成制药有限责任公司 | 一种高纯度氟雷拉纳中间体的制备方法 |
| NO20240925A1 (en) | 2023-09-15 | 2025-03-17 | Evah Atlantic Inc | Dihydroisoxazole compound for use in reducing ectoparasite infestations on fish |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6426333B1 (en) | 1996-09-19 | 2002-07-30 | Merial | Spot-on formulations for combating parasites |
| NL160809C (nl) | 1970-05-15 | 1979-12-17 | Duphar Int Res | Werkwijze ter bereiding van benzoylureumverbindingen, alsmede werkwijze ter bereiding van insekticide prepara- ten op basis van benzoylureumverbindingen. |
| US3950360A (en) | 1972-06-08 | 1976-04-13 | Sankyo Company Limited | Antibiotic substances |
| JPS4914624A (https=) | 1972-06-08 | 1974-02-08 | ||
| US3818047A (en) | 1972-08-07 | 1974-06-18 | C Henrick | Substituted pyrones |
| SE434277B (sv) | 1976-04-19 | 1984-07-16 | Merck & Co Inc | Sett att framstella nya antihelmintiskt verkande foreningar genom odling av streptomyces avermitilis |
| US4166452A (en) | 1976-05-03 | 1979-09-04 | Generales Constantine D J Jr | Apparatus for testing human responses to stimuli |
| CH604517A5 (https=) | 1976-08-19 | 1978-09-15 | Ciba Geigy Ag | |
| US4256108A (en) | 1977-04-07 | 1981-03-17 | Alza Corporation | Microporous-semipermeable laminated osmotic system |
| US4134973A (en) | 1977-04-11 | 1979-01-16 | Merck & Co., Inc. | Carbohydrate derivatives of milbemycin and processes therefor |
| US4199569A (en) | 1977-10-03 | 1980-04-22 | Merck & Co., Inc. | Selective hydrogenation products of C-076 compounds and derivatives thereof |
| US4144352A (en) | 1977-12-19 | 1979-03-13 | Merck & Co., Inc. | Milbemycin compounds as anthelmintic agents |
| US4203976A (en) | 1978-08-02 | 1980-05-20 | Merck & Co., Inc. | Sugar derivatives of C-076 compounds |
| US4265874A (en) | 1980-04-25 | 1981-05-05 | Alza Corporation | Method of delivering drug with aid of effervescent activity generated in environment of use |
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