JP2009518400A5 - - Google Patents
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- Publication number
- JP2009518400A5 JP2009518400A5 JP2008544409A JP2008544409A JP2009518400A5 JP 2009518400 A5 JP2009518400 A5 JP 2009518400A5 JP 2008544409 A JP2008544409 A JP 2008544409A JP 2008544409 A JP2008544409 A JP 2008544409A JP 2009518400 A5 JP2009518400 A5 JP 2009518400A5
- Authority
- JP
- Japan
- Prior art keywords
- composition
- composition according
- macrocyclic lactone
- benzimidazole
- moxidectin
- 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
- 239000000203 mixture Substances 0.000 claims 14
- 150000002596 lactones Chemical class 0.000 claims 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- YZBLFMPOMVTDJY-CBYMMZEQSA-N moxidectin Chemical compound O1[C@H](C(\C)=C\C(C)C)[C@@H](C)C(=N/OC)\C[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 YZBLFMPOMVTDJY-CBYMMZEQSA-N 0.000 claims 3
- 229960004816 moxidectin Drugs 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- NQPDXQQQCQDHHW-UHFFFAOYSA-N 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole Chemical group ClC=1C=C2NC(SC)=NC2=CC=1OC1=CC=CC(Cl)=C1Cl NQPDXQQQCQDHHW-UHFFFAOYSA-N 0.000 claims 2
- 239000005660 Abamectin Substances 0.000 claims 2
- 230000000507 anthelmentic effect Effects 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 2
- 229960000323 triclabendazole Drugs 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- OVYMWJFNQQOJBU-UHFFFAOYSA-N 1-octanoyloxypropan-2-yl octanoate Chemical compound CCCCCCCC(=O)OCC(C)OC(=O)CCCCCCC OVYMWJFNQQOJBU-UHFFFAOYSA-N 0.000 claims 1
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 claims 1
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims 1
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 claims 1
- 241000283690 Bos taurus Species 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 206010061217 Infestation Diseases 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- BWCRYQGQPDBOAU-UHFFFAOYSA-N Milbemycin D Natural products C1CC(C)C(C(C)C)OC21OC(CC=C(C)CC(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 BWCRYQGQPDBOAU-UHFFFAOYSA-N 0.000 claims 1
- YRWLZFXJFBZBEY-UHFFFAOYSA-N N-(6-butyl-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCCC1=CC=C2N=C(NC(=O)OC)NC2=C1 YRWLZFXJFBZBEY-UHFFFAOYSA-N 0.000 claims 1
- RAOCRURYZCVHMG-UHFFFAOYSA-N N-(6-propoxy-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCOC1=CC=C2N=C(NC(=O)OC)NC2=C1 RAOCRURYZCVHMG-UHFFFAOYSA-N 0.000 claims 1
- 241001494479 Pecora Species 0.000 claims 1
- 241000282887 Suidae Species 0.000 claims 1
- 229950008167 abamectin Drugs 0.000 claims 1
- VXTGHWHFYNYFFV-UHFFFAOYSA-N albendazole S-oxide Chemical compound CCCS(=O)C1=CC=C2NC(NC(=O)OC)=NC2=C1 VXTGHWHFYNYFFV-UHFFFAOYSA-N 0.000 claims 1
- 229950010075 albendazole sulfoxide Drugs 0.000 claims 1
- -1 alkylene glycol Chemical compound 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 claims 1
- 229960003475 cambendazole Drugs 0.000 claims 1
- QLFZZSKTJWDQOS-YDBLARSUSA-N doramectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C3CCCCC3)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C QLFZZSKTJWDQOS-YDBLARSUSA-N 0.000 claims 1
- 229960003997 doramectin Drugs 0.000 claims 1
- 244000078703 ectoparasite Species 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- 229960005473 fenbendazole Drugs 0.000 claims 1
- IRHZVMHXVHSMKB-UHFFFAOYSA-N fenbendazole Chemical compound [CH]1C2=NC(NC(=O)OC)=NC2=CC=C1SC1=CC=CC=C1 IRHZVMHXVHSMKB-UHFFFAOYSA-N 0.000 claims 1
- 238000003304 gavage Methods 0.000 claims 1
- 239000008240 homogeneous mixture Substances 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 229960002418 ivermectin Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960003439 mebendazole Drugs 0.000 claims 1
- BAXLBXFAUKGCDY-UHFFFAOYSA-N mebendazole Chemical compound [CH]1C2=NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=CC=C1 BAXLBXFAUKGCDY-UHFFFAOYSA-N 0.000 claims 1
- BWCRYQGQPDBOAU-WZBVPYLGSA-N milbemycin D Chemical compound C1C[C@H](C)[C@@H](C(C)C)O[C@@]21O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 BWCRYQGQPDBOAU-WZBVPYLGSA-N 0.000 claims 1
- BEZZFPOZAYTVHN-UHFFFAOYSA-N oxfendazole Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1S(=O)C1=CC=CC=C1 BEZZFPOZAYTVHN-UHFFFAOYSA-N 0.000 claims 1
- 229960004454 oxfendazole Drugs 0.000 claims 1
- 244000045947 parasite Species 0.000 claims 1
- 229950007337 parbendazole Drugs 0.000 claims 1
- 229920001515 polyalkylene glycol Polymers 0.000 claims 1
- QZWHWHNCPFEXLL-UHFFFAOYSA-N propan-2-yl n-[2-(1,3-thiazol-4-yl)-3h-benzimidazol-5-yl]carbamate Chemical compound N1C2=CC(NC(=O)OC(C)C)=CC=C2N=C1C1=CSC=N1 QZWHWHNCPFEXLL-UHFFFAOYSA-N 0.000 claims 1
- 229960004546 thiabendazole Drugs 0.000 claims 1
- 239000004308 thiabendazole Substances 0.000 claims 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 claims 1
- 235000010296 thiabendazole Nutrition 0.000 claims 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74272405P | 2005-12-06 | 2005-12-06 | |
| US60/742,724 | 2005-12-06 | ||
| PCT/US2006/046197 WO2007067470A2 (en) | 2005-12-06 | 2006-12-04 | Benzimidazole non-aqueous compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009518400A JP2009518400A (ja) | 2009-05-07 |
| JP2009518400A5 true JP2009518400A5 (https=) | 2013-07-04 |
| JP5342239B2 JP5342239B2 (ja) | 2013-11-13 |
Family
ID=37903547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008544409A Expired - Fee Related JP5342239B2 (ja) | 2005-12-06 | 2006-12-04 | ベンジイミダゾール非水性組成物 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7687471B2 (https=) |
| EP (1) | EP1957040B1 (https=) |
| JP (1) | JP5342239B2 (https=) |
| KR (1) | KR20080073700A (https=) |
| AR (1) | AR057219A1 (https=) |
| AU (1) | AU2006322120B2 (https=) |
| BR (1) | BRPI0619620B1 (https=) |
| CA (1) | CA2630458C (https=) |
| DK (1) | DK1957040T3 (https=) |
| ES (1) | ES2527120T3 (https=) |
| NZ (1) | NZ567991A (https=) |
| PT (1) | PT1957040E (https=) |
| TW (1) | TWI433691B (https=) |
| WO (1) | WO2007067470A2 (https=) |
| ZA (1) | ZA200804915B (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007144362A1 (en) | 2006-06-14 | 2007-12-21 | Intervet International B.V. | A suspension comprising benzimidazole carbamate and a polysorbate |
| TWI556741B (zh) | 2007-08-17 | 2016-11-11 | 英特威特國際股份有限公司 | 異唑啉組成物及其作為抗寄生蟲藥上的應用 |
| ES2617672T3 (es) * | 2008-10-08 | 2017-06-19 | Zoetis Services Llc | Composiciones antihelmínticas de bencimidazol |
| WO2010126857A1 (en) * | 2009-04-28 | 2010-11-04 | Wyeth Llc | Parasiticidal combinations of macrocyclic lactones and polyether antibiotics |
| US9808529B2 (en) | 2012-05-18 | 2017-11-07 | Luoda Pharma Pty Ltd | Liquid formulation |
| BR102013031277B1 (pt) * | 2013-12-05 | 2018-10-02 | Ouro Fino Participacoes E Empreendimentos S A | processo para preparar uma suspensão anti-helmíntica e suspensão anti-helmíntica injetável |
| CN112006981B (zh) * | 2020-07-30 | 2023-01-10 | 瑞普（天津）生物药业有限公司 | 一种长效复方驱虫药物液体制剂及其制备方法与应用 |
| CN116744917A (zh) | 2020-09-04 | 2023-09-12 | 礼蓝美国公司 | 适口调配物 |
| BR102020021181A2 (pt) * | 2020-10-16 | 2022-04-26 | Ipanema Industria De Produtos Veterinarios Ltda | Microssuspensão contra parasitas e método para sua obtenção |
| CN114304161B (zh) * | 2021-11-25 | 2024-08-09 | 兰州大学 | 三氯苯达唑在防治农业病原菌中的用途 |
| WO2025221973A1 (en) * | 2024-04-18 | 2025-10-23 | Jjr&D, Llc | Topical benzimidazole formulations and methods for use in treating inflammatory dermatoses |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994027598A1 (en) | 1993-05-26 | 1994-12-08 | Commonwealth Scientific And Industrial Research Organisation | Antiparasitic compositions |
| FR2755824B1 (fr) * | 1996-11-19 | 1999-01-08 | Virbac Sa | Formulation galenique des benzimidazoles a usage topique, son procede de preparation et ses utilisations |
| US6267985B1 (en) * | 1999-06-30 | 2001-07-31 | Lipocine Inc. | Clear oil-containing pharmaceutical compositions |
| AR035550A1 (es) * | 1999-06-04 | 2004-06-16 | Nufarm Ltd | Composiciones estables biocidas |
| NZ515772A (en) * | 1999-06-04 | 2002-12-20 | Nufarm Ltd | Pesticidal emulsion composition containing levamisole in the aqueous phase and an anthelmintic in the organic phase |
| CN1435176A (zh) | 2002-01-29 | 2003-08-13 | 王玉万 | 以表面活性剂为基础的含三氯苯哒唑的新制剂 |
| AU2002952597A0 (en) | 2002-11-11 | 2002-11-28 | Schering-Plough Pty. Limited | Topical parasiticide formulations and methods of treatment |
| WO2005074914A1 (en) * | 2004-02-03 | 2005-08-18 | Wyeth | Anthelmintic composition |
-
2006
- 2006-12-04 AR ARP060105354A patent/AR057219A1/es not_active Application Discontinuation
- 2006-12-04 EP EP06838906.3A patent/EP1957040B1/en active Active
- 2006-12-04 JP JP2008544409A patent/JP5342239B2/ja not_active Expired - Fee Related
- 2006-12-04 KR KR1020087009605A patent/KR20080073700A/ko not_active Ceased
- 2006-12-04 NZ NZ567991A patent/NZ567991A/en unknown
- 2006-12-04 DK DK06838906.3T patent/DK1957040T3/en active
- 2006-12-04 BR BRPI0619620-9A patent/BRPI0619620B1/pt active IP Right Grant
- 2006-12-04 PT PT68389063T patent/PT1957040E/pt unknown
- 2006-12-04 ES ES06838906.3T patent/ES2527120T3/es active Active
- 2006-12-04 CA CA2630458A patent/CA2630458C/en not_active Expired - Fee Related
- 2006-12-04 WO PCT/US2006/046197 patent/WO2007067470A2/en not_active Ceased
- 2006-12-04 AU AU2006322120A patent/AU2006322120B2/en active Active
- 2006-12-05 US US11/634,027 patent/US7687471B2/en not_active Expired - Fee Related
- 2006-12-06 TW TW095145431A patent/TWI433691B/zh not_active IP Right Cessation
-
2008
- 2008-06-05 ZA ZA200804915A patent/ZA200804915B/xx unknown
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