ES2571444T3 - Derivados de dihidrofurano-azetadina como agentes antiparasitarios - Google Patents
Derivados de dihidrofurano-azetadina como agentes antiparasitariosInfo
- Publication number
- ES2571444T3 ES2571444T3 ES13703286T ES13703286T ES2571444T3 ES 2571444 T3 ES2571444 T3 ES 2571444T3 ES 13703286 T ES13703286 T ES 13703286T ES 13703286 T ES13703286 T ES 13703286T ES 2571444 T3 ES2571444 T3 ES 2571444T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- cyano
- haloalkyl
- halo
- nrarb
- 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.)
- Active
Links
- 239000003096 antiparasitic agent Substances 0.000 title 1
- 229940125687 antiparasitic agent Drugs 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 16
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 9
- 125000005843 halogen group Chemical group 0.000 abstract 8
- 229910003827 NRaRb Inorganic materials 0.000 abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 abstract 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- YMEHWISYYMKMFO-WOMRJYOTSA-N methyl N-[(12E,15S)-15-[(4S)-4-(3-chlorophenyl)-2-oxopiperidin-1-yl]-9-oxo-8,17,19-triazatricyclo[14.2.1.02,7]nonadeca-1(18),2(7),3,5,12,16-hexaen-5-yl]carbamate Chemical compound COC(=O)Nc1ccc2-c3cnc([nH]3)[C@H](C\C=C\CCC(=O)Nc2c1)N1CC[C@@H](CC1=O)c1cccc(Cl)c1 YMEHWISYYMKMFO-WOMRJYOTSA-N 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- -1 nitro, hydroxy Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
-
- 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
- A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Un compuesto de fórmula (1)**Fórmula** en la que A es fenilo, naftilo o heteroarilo donde dicho heteroarilo contiene de 1 a 4 heteroátomos cada uno seleccionado independientemente de N, O y S; R1a, R1b y R1c son cada uno independientemente hidrógeno, halo, hidroxilo, ciano, nitro, alquilo C1-C6, haloalquilo C1- C6, alcoxi C1-C6, alquil C0-C3-cicloalquilo C3-C6, haloalcoxi C1-C6, -C(O)NH2, -SF5, o -S(O)pR; R2 es halo, ciano, alquilo C1-C6, haloalquilo C1-C6, nitro, hidroxilo, -C(O)NRaRb, alquenilo C2-C6, alquinilo C2-C6, - S(O)pR, u -OR; R3 es hidrógeno, halo, hidroxilo, ciano, alquilo C1-C6, haloalquilo C1-C6, alquil C0-C3-cicloalquilo C3-C6, -C(O)NH2, nitro, -SC(O)R, -C(O)NRaRb, alquil C0-C3-NRaR4, -NRaNRbR4, -NRaORb, -ONRaRb, N3, -NHR4, -OR, o -S(O)pR; R4 es hidrógeno, alquilo C1-C6, alquil C0-C6-cicloalquilo C3-C6, -C(O)R5, -C(S)R5, -C(O)NRaR5, -C(O)C(O)NRaR5, -S(O)pRc, -S(O)2NRaR5, -C(NR7)R5, -C(NR7)NRaR5, alquil C0-C6-fenilo, alquil C0-C6 heteroarilo, o alquil C0-C6- heterociclo; R5 es hidrógeno, alquilo C1-C6, alquenilo C2-C6, alquil C0-C6-cicloalquilo C3-C6, alquil C0-C6-fenilo, alquil C0-C6- heteroarilo, o alquil C0-C6-heterociclo; R6 es ciano, alquilo C1-C6, haloalquilo C1-C6, -C(O)NRaRb, alquenilo C2-C6, alquinilo C2-C6, haloalquenilo C2-C6, o haloalquinilo C2-C6; R7 es hidrógeno, alquilo C1-C6, hidroxilo, ciano, nitro, -S(O)pRc, o alcoxi C1-C6; R es alquilo C1-C6 o cicloalquilo C3-C6 cada uno opcionalmente sustituido con al menos un halo; Ra es hidrógeno, alquilo C1-C6 o alquil C0-C3-cicloalquilo C3-C6; en el que el alquilo y el alquilcicloalquilo están opcionalmente sustituidos con ciano o al menos un sustituyente halo; Rb es hidrógeno, alquilo C1-C6, cicloalquilo C3-C6, alquil C0-C3-fenilo, alquil C0-C3-heteroarilo o alquil C0-C3- heterociclo, cada uno opcionalmente sustituido, cuando sea químicamente posible, con al menos un sustituyente seleccionado de hidroxilo, ciano, halo, o -S(O)pR; Rc es alquilo C1-C6, haloalquilo C1-C6, haloalquil C1-C6-cicloalquilo C3-C6, alquil C0-C3-cicloalquilo C3-C6, alquil C0-C3- fenilo, alquil C0-C3-heteroarilo, o alquil C0-C3-heterociclo cada uno opcionalmente sustituido con al menos un sustituyente seleccionado de ciano, halo, hidroxilo, oxo, alquilo C1-C6, alcoxi C1-C6, haloalcoxi C1-C6, haloalquilo C1- C6, -S(O)pR, -SH, -S(O)pNRaRb, -NRaRb, -NRaC(O)Rb, -SC(O)Rb, -SCN, o -C(O)NRaRb; cada uno de R4 y R5 alquilo C1-C6 o alquil C0-C6-cicloalquilo C3-C6 puede estar opcional e independientemente sustituido con al menos un sustituyente seleccionado de alquilo C1-C6, ciano, halo, hidroxilo, oxo, alquilo C1-C6, alcoxi C1-C6, haloalcoxi C1-C6, haloalquilo C1-C6, -S(O)pRc, -SH, -S(O)pNRaRb, -NRaRb, -NRaC(O)Rb, -SC(O)Rc, -SCN, o -C(O)NRaRb; y en la que R4 y R5 alquil C0-C6-fenilo, alquil C0-C6-heteroarilo o resto alquil C0-C6-heterociclo puede estar además, opcionalmente sustituido con al menos un sustituyente seleccionado de alquilo C1-C6, hidroxialquilo C1-C6, ciano, halo, oxo, >=S, >=NR7, hidroxilo, alcoxi C1-C6, alquilo C1-C6, haloalquilo C1-C6, -SH, -S(O)pR y haloalcoxi C1-C6; n es el número entero 0, 1 o 2 y cuando n sea 2, cada uno de R2 puede ser idéntico al otro o diferente al otro y p es el número entero 0, 1 o 2; estereoisómeros del mismo y sales farmacéutica o veterinariamente aceptables del mismo.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261594569P | 2012-02-03 | 2012-02-03 | |
| PCT/US2013/023662 WO2013116230A1 (en) | 2012-02-03 | 2013-01-29 | Dihydrofuran azetidine derivatives as antiparasitic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2571444T3 true ES2571444T3 (es) | 2016-05-25 |
Family
ID=47679106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13703286T Active ES2571444T3 (es) | 2012-02-03 | 2013-01-29 | Derivados de dihidrofurano-azetadina como agentes antiparasitarios |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9133172B2 (es) |
| EP (1) | EP2814825B1 (es) |
| JP (1) | JP5997779B2 (es) |
| CN (1) | CN104169273B (es) |
| AR (1) | AR092792A1 (es) |
| AU (1) | AU2013215368A1 (es) |
| BR (1) | BR112014018650A8 (es) |
| CA (1) | CA2863625C (es) |
| CL (1) | CL2014002033A1 (es) |
| ES (1) | ES2571444T3 (es) |
| MX (1) | MX336430B (es) |
| PL (1) | PL2814825T3 (es) |
| RU (1) | RU2014131951A (es) |
| WO (1) | WO2013116230A1 (es) |
Families Citing this family (5)
| 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. |
| BR112015004826A2 (pt) * | 2012-09-07 | 2017-07-04 | Zoetis Llc | derivados espirocíclicos como agentes antiparasíticos |
| GB2538028B (en) | 2015-01-16 | 2017-02-08 | Avista Pharma Solutions | Antiparasitic compounds |
| AU2021311722A1 (en) | 2020-07-24 | 2023-02-02 | Elanco Us Inc. | Process for making an isoxazoline compound and intermediate thereof |
| EP4208157A1 (en) | 2020-09-04 | 2023-07-12 | Elanco Us Inc. | Palatable formulations |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW524667B (en) | 1996-12-05 | 2003-03-21 | Pfizer | Parasiticidal pyrazoles |
| WO2005014573A1 (en) * | 2003-08-07 | 2005-02-17 | Pharmacia & Upjohn Company Llc | Anthelmintic and insecticide pyrimidine derivatives |
| GB0329314D0 (en) | 2003-12-18 | 2004-01-21 | Pfizer Ltd | Substituted arylpyrazoles |
| TW200538433A (en) * | 2004-02-24 | 2005-12-01 | Irm Llc | Immunosuppressant compounds and compositiions |
| 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 |
| US8372867B2 (en) * | 2007-04-10 | 2013-02-12 | Bayer Cropscience Ag | Insecticidal aryl isoxazoline derivatives |
| 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 |
| EP2331536B1 (en) * | 2008-08-22 | 2013-08-21 | Syngenta Participations AG | Insecticidal compounds |
| EA201201171A1 (ru) | 2010-02-22 | 2013-03-29 | Зингента Партисипейшнс Аг | Дигидрофурановые производные в качестве инсектицидных соединений |
| ES2682303T3 (es) * | 2010-08-05 | 2018-09-19 | Zoetis Services Llc | Derivados de isoxazolina como agentes antiparasitarios |
-
2013
- 2013-01-29 WO PCT/US2013/023662 patent/WO2013116230A1/en not_active Ceased
- 2013-01-29 BR BR112014018650A patent/BR112014018650A8/pt not_active IP Right Cessation
- 2013-01-29 CN CN201380014259.5A patent/CN104169273B/zh not_active Expired - Fee Related
- 2013-01-29 PL PL13703286T patent/PL2814825T3/pl unknown
- 2013-01-29 AU AU2013215368A patent/AU2013215368A1/en not_active Abandoned
- 2013-01-29 JP JP2014555625A patent/JP5997779B2/ja not_active Expired - Fee Related
- 2013-01-29 EP EP13703286.8A patent/EP2814825B1/en not_active Not-in-force
- 2013-01-29 MX MX2014009387A patent/MX336430B/es unknown
- 2013-01-29 US US14/375,061 patent/US9133172B2/en not_active Expired - Fee Related
- 2013-01-29 CA CA2863625A patent/CA2863625C/en not_active Expired - Fee Related
- 2013-01-29 RU RU2014131951A patent/RU2014131951A/ru not_active Application Discontinuation
- 2013-01-29 ES ES13703286T patent/ES2571444T3/es active Active
- 2013-02-01 AR ARP130100320A patent/AR092792A1/es unknown
-
2014
- 2014-07-30 CL CL2014002033A patent/CL2014002033A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL2814825T3 (pl) | 2016-08-31 |
| CA2863625A1 (en) | 2013-08-08 |
| CN104169273A (zh) | 2014-11-26 |
| AR092792A1 (es) | 2015-05-06 |
| US9133172B2 (en) | 2015-09-15 |
| MX2014009387A (es) | 2014-08-27 |
| CN104169273B (zh) | 2016-11-02 |
| AU2013215368A1 (en) | 2014-08-21 |
| EP2814825A1 (en) | 2014-12-24 |
| BR112014018650A8 (pt) | 2017-07-11 |
| CA2863625C (en) | 2016-04-26 |
| EP2814825B1 (en) | 2016-03-23 |
| CL2014002033A1 (es) | 2014-10-03 |
| WO2013116230A1 (en) | 2013-08-08 |
| US20150038440A1 (en) | 2015-02-05 |
| BR112014018650A2 (es) | 2017-06-20 |
| JP2015511233A (ja) | 2015-04-16 |
| RU2014131951A (ru) | 2016-03-27 |
| JP5997779B2 (ja) | 2016-09-28 |
| MX336430B (es) | 2016-01-18 |
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