CA2929234C - Antiparisitic and pesticidal isoxazoline compounds - Google Patents
Antiparisitic and pesticidal isoxazoline compounds Download PDFInfo
- Publication number
- CA2929234C CA2929234C CA2929234A CA2929234A CA2929234C CA 2929234 C CA2929234 C CA 2929234C CA 2929234 A CA2929234 A CA 2929234A CA 2929234 A CA2929234 A CA 2929234A CA 2929234 C CA2929234 C CA 2929234C
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- CA
- Canada
- Prior art keywords
- alkyl
- haloalkyl
- compound
- hydrogen
- halogen
- Prior art date
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- 150000002547 isoxazolines Chemical class 0.000 title abstract description 20
- 230000000361 pesticidal effect Effects 0.000 title abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 70
- 241001465754 Metazoa Species 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 26
- 206010061217 Infestation Diseases 0.000 claims abstract description 19
- 208000030852 Parasitic disease Diseases 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims description 666
- 229910052739 hydrogen Inorganic materials 0.000 claims description 666
- 125000000217 alkyl group Chemical group 0.000 claims description 435
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 429
- 229910052736 halogen Inorganic materials 0.000 claims description 337
- 150000002367 halogens Chemical group 0.000 claims description 337
- 125000001188 haloalkyl group Chemical group 0.000 claims description 326
- 229910052799 carbon Inorganic materials 0.000 claims description 291
- -1 isoxazoline compound Chemical class 0.000 claims description 286
- 150000001721 carbon Chemical group 0.000 claims description 283
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 276
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 238
- 125000003342 alkenyl group Chemical group 0.000 claims description 149
- 150000001875 compounds Chemical class 0.000 claims description 148
- 125000000304 alkynyl group Chemical group 0.000 claims description 147
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 141
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 141
- 125000004432 carbon atom Chemical group C* 0.000 claims description 118
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 118
- 125000001153 fluoro group Chemical group F* 0.000 claims description 101
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 99
- 125000001624 naphthyl group Chemical group 0.000 claims description 89
- 125000004001 thioalkyl group Chemical group 0.000 claims description 88
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 86
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 79
- 125000003545 alkoxy group Chemical group 0.000 claims description 78
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 77
- 125000004414 alkyl thio group Chemical group 0.000 claims description 70
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 70
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 69
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 64
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 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 description 48
- 125000001072 heteroaryl group Chemical group 0.000 claims description 47
- 125000003282 alkyl amino group Chemical group 0.000 claims description 46
- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 44
- 125000004992 haloalkylamino group Chemical group 0.000 claims description 39
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 36
- 102200128931 rs3737311 Human genes 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 25
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 21
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 21
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 21
- 241000607479 Yersinia pestis Species 0.000 claims description 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 7
- 230000003071 parasitic effect Effects 0.000 claims description 7
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
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- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- PIEXCQIOSMOEOU-UHFFFAOYSA-N 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Br)C(=O)N(Cl)C1=O PIEXCQIOSMOEOU-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 30
- 230000000590 parasiticidal effect Effects 0.000 abstract description 11
- 230000008569 process Effects 0.000 abstract description 10
- 238000002360 preparation method Methods 0.000 abstract description 9
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 abstract description 2
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- 239000002904 solvent Substances 0.000 description 13
- 244000045947 parasite Species 0.000 description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 11
- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 239000006184 cosolvent Substances 0.000 description 10
- 230000006378 damage Effects 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 10
- 125000006344 nonafluoro n-butyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 10
- 241000238876 Acari Species 0.000 description 9
- 239000004530 micro-emulsion Substances 0.000 description 9
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- 235000011187 glycerol Nutrition 0.000 description 8
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- 238000002425 crystallisation Methods 0.000 description 7
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 229910002059 quaternary alloy Inorganic materials 0.000 description 1
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
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- 241000894007 species Species 0.000 description 1
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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
- 238000012360 testing method Methods 0.000 description 1
- 125000006092 tetrahydro-1,1-dioxothienyl group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- 229940124597 therapeutic agent Drugs 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
- 238000011200 topical administration Methods 0.000 description 1
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- 229910052723 transition metal Inorganic materials 0.000 description 1
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- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
-
- 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
- C07D413/02—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
-
- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361898578P | 2013-11-01 | 2013-11-01 | |
| US61/898,578 | 2013-11-01 | ||
| PCT/US2014/063074 WO2015066277A1 (en) | 2013-11-01 | 2014-10-30 | Antiparisitic and pesticidal isoxazoline compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2929234A1 CA2929234A1 (en) | 2015-05-07 |
| CA2929234C true CA2929234C (en) | 2022-01-11 |
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|---|---|---|---|
| CA2929234A Active CA2929234C (en) | 2013-11-01 | 2014-10-30 | Antiparisitic and pesticidal isoxazoline compounds |
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| DK3298027T3 (da) | 2015-05-20 | 2021-08-09 | Boehringer Ingelheim Animal Health Usa Inc | Anthelmintiske depsipeptidforbindelser |
| WO2016207234A1 (en) | 2015-06-23 | 2016-12-29 | Intervet International B.V. | Isoxazoline solution containing vitamin e for use with sanitized drinking water |
| 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 |
| EP3541789A1 (en) | 2016-11-16 | 2019-09-25 | 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 |
| KR102785432B1 (ko) | 2018-07-09 | 2025-03-21 | 베링거잉겔하임베트메디카게엠베하 | 구충성 헤테로시클릭 화합물 |
| CN113825543B (zh) | 2019-03-19 | 2024-09-06 | 勃林格殷格翰动物保健有限公司 | 驱虫的氮杂-苯并噻吩和氮杂-苯并呋喃化合物 |
| US12497370B2 (en) | 2019-12-18 | 2025-12-16 | Elanco Tiergesundheit Ag | Isoxazoline derivatives |
| KR20230028268A (ko) | 2020-05-29 | 2023-02-28 | 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 | 구충성 헤테로시클릭 화합물 |
| BR112023015168A2 (pt) | 2021-01-27 | 2023-10-03 | Corteva Agriscience Llc | Compostos de ciclopropilamida contra parasitas em peixes |
| US20240116854A1 (en) | 2021-01-27 | 2024-04-11 | Intervet Inc. | Cyclopropylamide compounds against parasites in fish |
| US20240140917A1 (en) * | 2021-02-11 | 2024-05-02 | Basf Se | Substituted isoxazoline derivatives |
| 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 |
| CR20240207A (es) | 2021-11-01 | 2024-06-25 | 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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| 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. |
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