JP2012509327A5 - - Google Patents
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- JP2012509327A5 JP2012509327A5 JP2011537523A JP2011537523A JP2012509327A5 JP 2012509327 A5 JP2012509327 A5 JP 2012509327A5 JP 2011537523 A JP2011537523 A JP 2011537523A JP 2011537523 A JP2011537523 A JP 2011537523A JP 2012509327 A5 JP2012509327 A5 JP 2012509327A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cavity
- compound
- haloalkyl
- composition
- 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.)
- Granted
Links
- -1 1-arylpyrazole compound Chemical class 0.000 claims 34
- 239000000203 mixture Substances 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 238000000034 method Methods 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 230000009977 dual effect Effects 0.000 claims 8
- 125000001188 haloalkyl group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 5
- YLYBTZIQSIBWLI-UHFFFAOYSA-N octyl acetate Chemical compound CCCCCCCCOC(C)=O YLYBTZIQSIBWLI-UHFFFAOYSA-N 0.000 claims 4
- 244000045947 parasite Species 0.000 claims 4
- 238000011282 treatment Methods 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 claims 3
- 229960002587 amitraz Drugs 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 claims 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- 239000005899 Fipronil Substances 0.000 claims 2
- 206010061217 Infestation Diseases 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims 2
- 229940013764 fipronil Drugs 0.000 claims 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 230000003071 parasitic effect Effects 0.000 claims 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims 2
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 claims 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims 1
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 claims 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 claims 1
- HBTAOSGHCXUEKI-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 HBTAOSGHCXUEKI-UHFFFAOYSA-N 0.000 claims 1
- STUSTWKEFDQFFZ-UHFFFAOYSA-N Chlordimeform Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 claims 1
- RDOFJDLLWVCMRU-UHFFFAOYSA-N Diisobutyl adipate Chemical compound CC(C)COC(=O)CCCCC(=O)OCC(C)C RDOFJDLLWVCMRU-UHFFFAOYSA-N 0.000 claims 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 150000008378 aryl ethers Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 229940007550 benzyl acetate Drugs 0.000 claims 1
- 229960002903 benzyl benzoate Drugs 0.000 claims 1
- 229940043232 butyl acetate Drugs 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 150000003997 cyclic ketones Chemical class 0.000 claims 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims 1
- 229940031769 diisobutyl adipate Drugs 0.000 claims 1
- 229940031578 diisopropyl adipate Drugs 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229960004756 ethanol Drugs 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- NPCUJHYOBSHUJJ-RIYZIHGNSA-N formparanate Chemical compound CNC(=O)OC1=CC=C(\N=C\N(C)C)C(C)=C1 NPCUJHYOBSHUJJ-RIYZIHGNSA-N 0.000 claims 1
- 239000001087 glyceryl triacetate Substances 0.000 claims 1
- 235000013773 glyceryl triacetate Nutrition 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 229960004592 isopropanol Drugs 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229960002622 triacetin Drugs 0.000 claims 1
- 0 CC(*)=Nc1cccc(C**)c1 Chemical compound CC(*)=Nc1cccc(C**)c1 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11603808P | 2008-11-19 | 2008-11-19 | |
| US61/116,038 | 2008-11-19 | ||
| US14256109P | 2009-01-05 | 2009-01-05 | |
| US61/142,561 | 2009-01-05 | ||
| US16738109P | 2009-04-07 | 2009-04-07 | |
| US61/167,381 | 2009-04-07 | ||
| PCT/US2009/064443 WO2010059529A2 (en) | 2008-11-19 | 2009-11-13 | Compositions comprising an aryl pyrazole and/or a formamidine, methods and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014207819A Division JP2015013899A (ja) | 2008-11-19 | 2014-10-09 | アリールピラゾールおよび／またはホルムアミジンを含む組成物、それらの方法ならびに使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012509327A JP2012509327A (ja) | 2012-04-19 |
| JP2012509327A5 true JP2012509327A5 (enExample) | 2013-01-10 |
| JP5755143B2 JP5755143B2 (ja) | 2015-07-29 |
Family
ID=41667256
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011537523A Expired - Fee Related JP5755143B2 (ja) | 2008-11-19 | 2009-11-13 | アリールピラゾールおよび／またはホルムアミジンを含む組成物、それらの方法ならびに使用 |
| JP2014207819A Pending JP2015013899A (ja) | 2008-11-19 | 2014-10-09 | アリールピラゾールおよび／またはホルムアミジンを含む組成物、それらの方法ならびに使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014207819A Pending JP2015013899A (ja) | 2008-11-19 | 2014-10-09 | アリールピラゾールおよび／またはホルムアミジンを含む組成物、それらの方法ならびに使用 |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US8450357B2 (enExample) |
| EP (2) | EP2550962B1 (enExample) |
| JP (2) | JP5755143B2 (enExample) |
| KR (1) | KR101660068B1 (enExample) |
| CN (1) | CN102271672B (enExample) |
| AP (1) | AP3359A (enExample) |
| AR (1) | AR074383A1 (enExample) |
| AU (2) | AU2009316899B2 (enExample) |
| BR (1) | BRPI0922043B1 (enExample) |
| CA (1) | CA2743856C (enExample) |
| CO (1) | CO6382116A2 (enExample) |
| CR (1) | CR20110273A (enExample) |
| ES (1) | ES2781828T3 (enExample) |
| IL (1) | IL212938A (enExample) |
| MX (1) | MX2011005184A (enExample) |
| MY (1) | MY155497A (enExample) |
| NZ (2) | NZ612417A (enExample) |
| PL (1) | PL396375A1 (enExample) |
| RU (3) | RU2011124948A (enExample) |
| SG (1) | SG171751A1 (enExample) |
| TW (1) | TWI505777B (enExample) |
| WO (1) | WO2010059529A2 (enExample) |
| ZA (2) | ZA201103618B (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7531186B2 (en) * | 2003-12-17 | 2009-05-12 | Merial Limited | Topical formulations comprising 1-N-arylpyrazole derivatives and amitraz |
| FR2909975B1 (fr) * | 2006-12-13 | 2009-04-17 | Eskiss Packaging Soc Par Actio | Flacon destine a recevoir une dose determinee d'un liquide |
| EP2222168B1 (en) * | 2007-11-26 | 2018-09-12 | Merial, Inc. | Solvent systems for pour-on formulations for combating parasites |
| KR101660068B1 (ko) * | 2008-11-19 | 2016-09-26 | 메리얼 인코포레이티드 | 기생충 감염 치료를 위한 1-아릴피라졸 단독 또는 포름아미딘과의 조합을 포함하는 조성물 |
| US9173728B2 (en) * | 2008-11-19 | 2015-11-03 | Merial Inc. | Multi-cavity container having offset indentures for dispensing fluids |
| EP2416663A2 (en) | 2009-03-18 | 2012-02-15 | Martin Benedict George Donnelly | Parasiticidal formulation |
| JP2011153129A (ja) * | 2009-12-28 | 2011-08-11 | Sumitomo Chemical Co Ltd | 動物外部寄生虫防除組成物 |
| UY33443A (es) * | 2010-06-19 | 2012-01-31 | Bayer Animal Health Gmbh | Preparacion que contiene ectoparasiticida para la formacion de emulsion espontanea |
| CA2832801C (en) * | 2011-04-15 | 2015-07-07 | Douglas J. Hohlbein | Oral care kit |
| CH705153A1 (fr) * | 2011-06-24 | 2012-12-31 | Heidi Hall | Mors et système pour envoyer une substance visqueuse et/ou liquide dans la bouche d'un animal. |
| US9034912B1 (en) * | 2012-03-23 | 2015-05-19 | Jugal K. Taneja | Veterinary composition and method |
| BR112014024832B1 (pt) | 2012-04-04 | 2022-05-31 | Intervet International B.V. | Método para a preparação de uma composição farmacêutica veterinária mastigável macia, composição farmacêutica, e, uso da composição |
| US20130292414A1 (en) * | 2012-05-02 | 2013-11-07 | Spencer D. Sutherland | Dispensing Device |
| WO2014060960A1 (en) | 2012-10-16 | 2014-04-24 | Solano Smart Products Ltd. | Topical formulations for treating parasitic infestations |
| WO2015007923A1 (es) * | 2013-07-18 | 2015-01-22 | König Lab, S.L. | Procedimiento de desparasitación de animales mediante la aplicación simultánea de dos o más agentes parasiticidas por vía dérmica y dispositivo para su puesta en práctica |
| 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 |
| HUE063842T2 (hu) | 2013-12-20 | 2024-02-28 | Intervet Int Bv | Izoxazolin vegyületek felhasználása baromfiban |
| USD765520S1 (en) * | 2014-01-07 | 2016-09-06 | The Coca-Cola Company | Blister package |
| WO2016022066A1 (en) | 2014-08-04 | 2016-02-11 | Jerry Tan Eye Surgery Pte Ltd | Pharmaceutical compositions for demodex related blepharitis and eyelid crusting |
| JP6722464B2 (ja) * | 2016-01-28 | 2020-07-15 | 株式会社大阪製薬 | 動物用害虫防除具 |
| US10512628B2 (en) | 2016-04-24 | 2019-12-24 | Solano S.P. Ltd. | Dinotefuran liquid flea and tick treatment |
| KR20250065422A (ko) | 2017-12-15 | 2025-05-12 | 타르서스 파마수티칼스, 아이엔씨. | 안검염을 치료하기 위한 이속사졸린 구충제 제제 및 방법 |
| CN111970921B (zh) * | 2018-04-12 | 2022-10-04 | 格伦·安德鲁·布拉德肖 | 动物治疗块 |
| JP7199653B2 (ja) * | 2018-08-17 | 2023-01-06 | 住化エンバイロメンタルサイエンス株式会社 | 樹脂製容器入り外部寄生虫駆除剤 |
| KR102056732B1 (ko) * | 2019-07-10 | 2019-12-17 | (주)알메디카 | 환자 맞춤형 약액을 수용하기 위한 일회용 약액 용기, 이를 제작하는 장치, 및 제작 방법 |
| WO2023156938A1 (en) * | 2022-02-17 | 2023-08-24 | Boehringer Ingelheim Vetmedica Gmbh | Method and system for providing a fluid product mailer |
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2009
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- 2009-11-13 WO PCT/US2009/064443 patent/WO2010059529A2/en not_active Ceased
- 2009-11-13 US US12/618,534 patent/US8450357B2/en active Active
- 2009-11-13 MY MYPI2011002190A patent/MY155497A/en unknown
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- 2009-11-13 AU AU2009316899A patent/AU2009316899B2/en not_active Ceased
- 2009-11-13 EP EP12189478.6A patent/EP2550962B1/en active Active
- 2009-11-13 CN CN200980153974.0A patent/CN102271672B/zh not_active Expired - Fee Related
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- 2009-11-13 JP JP2011537523A patent/JP5755143B2/ja not_active Expired - Fee Related
- 2009-11-13 EP EP09760661A patent/EP2364147A2/en not_active Withdrawn
- 2009-11-13 ES ES12189478T patent/ES2781828T3/es active Active
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