AR092793A1 - Procedimiento para la preparacion de derivados de isoxazolina azetidina quirales como agentes antiparasitarios - Google Patents
Procedimiento para la preparacion de derivados de isoxazolina azetidina quirales como agentes antiparasitariosInfo
- Publication number
- AR092793A1 AR092793A1 ARP130100321A ARP130100321A AR092793A1 AR 092793 A1 AR092793 A1 AR 092793A1 AR P130100321 A ARP130100321 A AR P130100321A AR P130100321 A ARP130100321 A AR P130100321A AR 092793 A1 AR092793 A1 AR 092793A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- phenyl
- azetidin
- cycloalkyl
- halo
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 6
- 238000002360 preparation method Methods 0.000 title abstract 2
- LZNQKPCMSCHBFF-UHFFFAOYSA-N azetidine;4,5-dihydro-1,2-oxazole Chemical class C1CNC1.C1CC=NO1 LZNQKPCMSCHBFF-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 6
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 5
- 125000005843 halogen group Chemical group 0.000 abstract 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 4
- 229910003827 NRaRb Inorganic materials 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 abstract 3
- -1 = S Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
- 125000004043 oxo group Chemical group O=* 0.000 abstract 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
- VOXJHBJSBBOWHS-UHFFFAOYSA-N 1-[4-(azetidin-3-yl)phenyl]ethanone Chemical class C1=CC(C(=O)C)=CC=C1C1CNC1 VOXJHBJSBBOWHS-UHFFFAOYSA-N 0.000 abstract 2
- WHOVKIMCOPXUQR-UHFFFAOYSA-N 3-[4-(azetidin-3-yl)phenyl]-5-phenyl-5-(trifluoromethyl)-4h-1,2-oxazole Chemical class N=1OC(C(F)(F)F)(C=2C=CC=CC=2)CC=1C(C=C1)=CC=C1C1CNC1 WHOVKIMCOPXUQR-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 abstract 1
- TVGSMPZXTCQNAB-UHFFFAOYSA-N 1-[4-(azetidin-3-yl)phenyl]-4,4,4-trifluoro-3-phenylbut-2-en-1-one Chemical class FC(F)(F)C(=CC(=O)c1ccc(cc1)C1CNC1)c1ccccc1 TVGSMPZXTCQNAB-UHFFFAOYSA-N 0.000 abstract 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 abstract 1
- ZQQSYPZAPHRXRY-UHFFFAOYSA-N 1-hydroxyazetidine Chemical compound ON1CCC1 ZQQSYPZAPHRXRY-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- KHNGFFOEQHPXRG-UHFFFAOYSA-N 2-bromo-1-phenylazetidine Chemical compound BrC1CCN1C1=CC=CC=C1 KHNGFFOEQHPXRG-UHFFFAOYSA-N 0.000 abstract 1
- RAXRSTOKCITCSP-UHFFFAOYSA-N 3-(4-bromophenyl)azetidin-3-ol Chemical compound C=1C=C(Br)C=CC=1C1(O)CNC1 RAXRSTOKCITCSP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 235000001258 Cinchona calisaya Nutrition 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 238000010640 amide synthesis reaction Methods 0.000 abstract 1
- 125000006242 amine protecting group Chemical group 0.000 abstract 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 abstract 1
- 125000002393 azetidinyl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 238000003682 fluorination reaction Methods 0.000 abstract 1
- 229910052731 fluorine Chemical group 0.000 abstract 1
- 239000011737 fluorine Chemical group 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229960000948 quinine Drugs 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
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
- C07D413/10—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261594614P | 2012-02-03 | 2012-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR092793A1 true AR092793A1 (es) | 2015-05-06 |
Family
ID=47679107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP130100321A AR092793A1 (es) | 2012-02-03 | 2013-02-01 | Procedimiento para la preparacion de derivados de isoxazolina azetidina quirales como agentes antiparasitarios |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20140371464A1 (https=) |
| EP (1) | EP2809667A1 (https=) |
| JP (1) | JP2015505560A (https=) |
| CN (1) | CN104169276A (https=) |
| AR (1) | AR092793A1 (https=) |
| AU (1) | AU2013215374A1 (https=) |
| BR (1) | BR112014019212A8 (https=) |
| CA (1) | CA2863629A1 (https=) |
| CL (1) | CL2014002034A1 (https=) |
| MX (1) | MX2014009388A (https=) |
| RU (1) | RU2014131950A (https=) |
| UY (1) | UY34612A (https=) |
| WO (1) | WO2013116236A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX336431B (es) * | 2012-05-09 | 2016-01-18 | Zoetis Services Llc | Derivados de azetidina como agentes antiparasitarios. |
| UY40429A (es) | 2016-02-24 | 2023-10-13 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos antiparasitarios de isoxazolina, formulaciones inyectables de acción prolongada que los comprenden, métodos y usos de los mismos |
| DK3440062T3 (da) | 2016-04-06 | 2022-01-03 | Boehringer Ingelheim Animal Health Usa Inc | Fremgangsmåde til fremstillingen af enantiomerisk berigede isoxazolinforbindelser - krystallinsk toluensolvat af (s)-afoxolaner |
| AU2017344097A1 (en) | 2016-10-14 | 2019-05-02 | Boehringer Ingelheim Animal Health USA Inc. | Pesticidal and parasiticidal vinyl isoxazoline compounds |
| MX2020001724A (es) | 2017-08-14 | 2020-07-29 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos de pirazol-isoxazolina plaguicidas y parasiticidas. |
| BR112021025588A2 (pt) * | 2019-06-19 | 2022-02-01 | Nmd Pharma As | Processo para a preparação dos inibidores de canal de cloreto clc-1 |
| AU2021311722A1 (en) | 2020-07-24 | 2023-02-02 | Elanco Us Inc. | Process for making an isoxazoline compound and intermediate thereof |
| AU2022326468A1 (en) | 2021-08-11 | 2023-11-30 | ELANCO US, Inc. | Process for making diaryl isoxazoline derivative |
| WO2026043852A1 (en) | 2024-08-20 | 2026-02-26 | Zoetis Services Llc | Process for preparing optically enriched isoxazolines |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101331127B (zh) * | 2005-12-16 | 2012-05-23 | 杜邦公司 | 用于防治无脊椎害虫的5-芳基异噁唑啉 |
| TW200803740A (en) | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
| BRPI0707091B8 (pt) * | 2006-03-10 | 2018-02-14 | Nissan Chemical Ind Ltd | composto de isoxalina e benzaldoxima substituído ou um sal do mesmo; pesticida, agroquímico, endo- ou ecto-parasiticidapara mamíferos ou pássaros, inseticida e acaricida contendo como um ou mais ingredientes ativos selecionados a partir do composto de isoxalina substituído e o sal do mesmo |
| JP2008044880A (ja) * | 2006-08-15 | 2008-02-28 | Bayer Cropscience Ag | 殺虫性イソオキサゾリン類 |
| US8303622B2 (en) | 2007-03-14 | 2012-11-06 | St. Jude Medical, Inc. | Heart valve chordae replacement methods and apparatus |
| JP2008260691A (ja) * | 2007-04-10 | 2008-10-30 | Bayer Cropscience Ag | 殺虫性アリールイソオキサゾリン誘導体 |
| CN101801940B (zh) | 2007-09-10 | 2013-04-10 | 日产化学工业株式会社 | 取代异*唑啉化合物和有害生物防除剂 |
| WO2009063910A1 (ja) | 2007-11-12 | 2009-05-22 | Nissan Chemical Industries, Ltd. | 光学活性イソキサゾリン化合物の触媒的不斉合成方法 |
| CA2747354C (en) * | 2008-12-19 | 2016-12-06 | Novartis Ag | Isoxazoline derivatives and their use as pesticide |
| AU2011220041A1 (en) | 2010-02-25 | 2012-08-23 | Syngenta Limited | Process for the preparation of isoxazoline derivatives |
| ES2682303T3 (es) * | 2010-08-05 | 2018-09-19 | Zoetis Services Llc | Derivados de isoxazolina como agentes antiparasitarios |
-
2013
- 2013-01-29 JP JP2014555626A patent/JP2015505560A/ja active Pending
- 2013-01-29 CN CN201380014566.3A patent/CN104169276A/zh active Pending
- 2013-01-29 BR BR112014019212A patent/BR112014019212A8/pt not_active IP Right Cessation
- 2013-01-29 EP EP13703287.6A patent/EP2809667A1/en not_active Withdrawn
- 2013-01-29 MX MX2014009388A patent/MX2014009388A/es unknown
- 2013-01-29 US US14/375,056 patent/US20140371464A1/en not_active Abandoned
- 2013-01-29 RU RU2014131950A patent/RU2014131950A/ru unknown
- 2013-01-29 CA CA2863629A patent/CA2863629A1/en not_active Abandoned
- 2013-01-29 AU AU2013215374A patent/AU2013215374A1/en not_active Abandoned
- 2013-01-29 WO PCT/US2013/023673 patent/WO2013116236A1/en not_active Ceased
- 2013-02-01 AR ARP130100321A patent/AR092793A1/es unknown
- 2013-02-04 UY UY0001034612A patent/UY34612A/es not_active Application Discontinuation
-
2014
- 2014-07-30 CL CL2014002034A patent/CL2014002034A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2863629A1 (en) | 2013-08-08 |
| BR112014019212A2 (https=) | 2017-06-20 |
| AU2013215374A1 (en) | 2014-08-21 |
| EP2809667A1 (en) | 2014-12-10 |
| US20140371464A1 (en) | 2014-12-18 |
| MX2014009388A (es) | 2014-08-27 |
| JP2015505560A (ja) | 2015-02-23 |
| CL2014002034A1 (es) | 2014-11-14 |
| RU2014131950A (ru) | 2016-03-27 |
| UY34612A (es) | 2013-09-30 |
| CN104169276A (zh) | 2014-11-26 |
| BR112014019212A8 (pt) | 2017-07-11 |
| WO2013116236A1 (en) | 2013-08-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |