JP2014504586A5 - - Google Patents
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- JP2014504586A5 JP2014504586A5 JP2013545416A JP2013545416A JP2014504586A5 JP 2014504586 A5 JP2014504586 A5 JP 2014504586A5 JP 2013545416 A JP2013545416 A JP 2013545416A JP 2013545416 A JP2013545416 A JP 2013545416A JP 2014504586 A5 JP2014504586 A5 JP 2014504586A5
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- JP
- Japan
- Prior art keywords
- methyl
- transsurface
- compound
- formulation
- solvent
- 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.)
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- -1 methoxyethyl Chemical group 0.000 claims 30
- 239000000203 mixture Substances 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 6
- 239000012049 topical pharmaceutical composition Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- 239000007788 liquid Substances 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 238000009472 formulation Methods 0.000 claims 4
- 230000000699 topical effect Effects 0.000 claims 4
- CTPDSKVQLSDPLC-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxy)ethanol Chemical compound OCCOCC1CCCO1 CTPDSKVQLSDPLC-UHFFFAOYSA-N 0.000 claims 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- 241000238631 Hexapoda Species 0.000 claims 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 3
- 239000006184 cosolvent Substances 0.000 claims 3
- LZCLXQDLBQLTDK-BYPYZUCNSA-N ethyl (2S)-lactate Chemical compound CCOC(=O)[C@H](C)O LZCLXQDLBQLTDK-BYPYZUCNSA-N 0.000 claims 3
- 239000003630 growth substance Substances 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 208000030852 Parasitic disease Diseases 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000004970 halomethyl group Chemical group 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims 2
- 239000004544 spot-on Substances 0.000 claims 2
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-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
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-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
- 208000026803 Animal Parasitic disease Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 239000005891 Cyromazine Substances 0.000 claims 1
- 239000005893 Diflubenzuron Substances 0.000 claims 1
- 239000005894 Emamectin Substances 0.000 claims 1
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 claims 1
- 239000005912 Lufenuron Substances 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 239000005927 Pyriproxyfen Substances 0.000 claims 1
- 239000005942 Triflumuron Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 229960005233 cineole Drugs 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 1
- LVQDKIWDGQRHTE-UHFFFAOYSA-N cyromazine Chemical compound NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 claims 1
- 229950000775 cyromazine Drugs 0.000 claims 1
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 claims 1
- 229940019503 diflubenzuron Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- CXEGAUYXQAKHKJ-NSBHKLITSA-N emamectin 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](NC)[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 CXEGAUYXQAKHKJ-NSBHKLITSA-N 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims 1
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 229920005555 halobutyl Polymers 0.000 claims 1
- 125000004968 halobutyl group Chemical group 0.000 claims 1
- 125000004969 haloethyl group Chemical group 0.000 claims 1
- HICUREFSAIZXFQ-JOWPUVSESA-N i9z29i000j Chemical compound C1C[C@H](C)[C@@H](CC)O[C@@]21O[C@H](C\C=C(C)\[C@H](OC(=O)C(=N/OC)\C=1C=CC=CC=1)[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 HICUREFSAIZXFQ-JOWPUVSESA-N 0.000 claims 1
- 229960002418 ivermectin Drugs 0.000 claims 1
- 229950000961 latidectin Drugs 0.000 claims 1
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 claims 1
- 229960000521 lufenuron Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 1
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 claims 1
- 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 1
- 229960004816 moxidectin Drugs 0.000 claims 1
- 239000004540 pour-on Substances 0.000 claims 1
- 125000004673 propylcarbonyl group Chemical group 0.000 claims 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- AFJYYKSVHJGXSN-KAJWKRCWSA-N selamectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(O[C@@H]([C@@H](C)CC2)C2CCCCC2)C2)C[C@@H]2OC(=O)[C@@H]([C@]23O)C=C(C)C(=N\O)/[C@H]3OC\C2=C/C=C/[C@@H]1C AFJYYKSVHJGXSN-KAJWKRCWSA-N 0.000 claims 1
- 229960002245 selamectin Drugs 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10197089 | 2010-12-27 | ||
| EP10197089.5 | 2010-12-27 | ||
| US201161430240P | 2011-01-06 | 2011-01-06 | |
| US61/430,240 | 2011-01-06 | ||
| PCT/EP2011/073828 WO2012089622A2 (en) | 2010-12-27 | 2011-12-22 | Topical localized isoxazoline formulation |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016139272A Division JP6246864B2 (ja) | 2010-12-27 | 2016-07-14 | 経表面局所イソオキサゾリン製剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014504586A JP2014504586A (ja) | 2014-02-24 |
| JP2014504586A5 true JP2014504586A5 (https=) | 2015-02-05 |
| JP6002148B2 JP6002148B2 (ja) | 2016-10-05 |
Family
ID=43971048
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013545416A Active JP6002148B2 (ja) | 2010-12-27 | 2011-12-22 | 経表面局所イソオキサゾリン製剤 |
| JP2016139272A Active JP6246864B2 (ja) | 2010-12-27 | 2016-07-14 | 経表面局所イソオキサゾリン製剤 |
| JP2017217049A Active JP6514754B2 (ja) | 2010-12-27 | 2017-11-10 | 経表面局所イソオキサゾリン製剤 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016139272A Active JP6246864B2 (ja) | 2010-12-27 | 2016-07-14 | 経表面局所イソオキサゾリン製剤 |
| JP2017217049A Active JP6514754B2 (ja) | 2010-12-27 | 2017-11-10 | 経表面局所イソオキサゾリン製剤 |
Country Status (19)
| Country | Link |
|---|---|
| US (4) | US9173870B2 (https=) |
| EP (1) | EP2658542B2 (https=) |
| JP (3) | JP6002148B2 (https=) |
| KR (2) | KR20130130761A (https=) |
| CN (2) | CN105616406B (https=) |
| AU (2) | AU2016201954B2 (https=) |
| BR (1) | BR112013015503A2 (https=) |
| CA (1) | CA2822839C (https=) |
| DK (1) | DK2658542T4 (https=) |
| ES (1) | ES2908094T5 (https=) |
| FI (1) | FI2658542T4 (https=) |
| HU (1) | HUE058291T2 (https=) |
| MX (2) | MX383895B (https=) |
| NZ (1) | NZ611476A (https=) |
| PL (1) | PL2658542T5 (https=) |
| PT (1) | PT2658542T (https=) |
| RU (2) | RU2749733C2 (https=) |
| WO (1) | WO2012089622A2 (https=) |
| ZA (1) | ZA201304514B (https=) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6002148B2 (ja) | 2010-12-27 | 2016-10-05 | インターベット インターナショナル ベー． フェー． | 経表面局所イソオキサゾリン製剤 |
| NZ611474A (en) † | 2010-12-27 | 2015-08-28 | Intervet Int Bv | Topical localized isoxazoline formulation comprising glycofurol |
| RS58417B1 (sr) | 2011-09-12 | 2019-04-30 | Merial Inc | Paraziticidne kompozicije koje sadrže izoksazolinsko aktivno sredstvo, postupci i upotrebe povezane sa njima |
| EP3216448B8 (en) | 2012-02-06 | 2019-06-05 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal oral veterinary compositions comprising systemically-acting active agents, methods and uses thereof |
| JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
| WO2013150055A1 (en) | 2012-04-04 | 2013-10-10 | Intervet International B.V. | Solid oral pharmaceutical compositions for isoxazoline compounds |
| WO2015066277A1 (en) | 2013-11-01 | 2015-05-07 | Merial Limited | Antiparisitic and pesticidal isoxazoline compounds |
| EP3082806B1 (en) | 2013-12-20 | 2021-05-12 | Intervet International B.V. | Use of isoxazoline derivatives for the treatment or prevention of arthropod infestations in poultry |
| EP3082867B1 (en) | 2013-12-20 | 2024-01-17 | Intervet International B.V. | Isoxazoline compositions and use thereof in the prevention or treatment of parasite infestations in animals |
| EP3131398B1 (en) | 2014-04-17 | 2019-10-23 | Boehringer Ingelheim Animal Health USA Inc. | Use of malononitrile compounds for protecting animals from parasites |
| US20170232024A1 (en) | 2014-08-04 | 2017-08-17 | Jerry Tan Eye Surgery Pte Ltd | Pharmaceutical compositions for demodex related blepharitis and eyelid crusting |
| EP3236960B1 (en) | 2014-12-22 | 2025-01-29 | Intervet International B.V. | Fluralaner for use in the treatment of demodicosis |
| UY36570A (es) | 2015-02-26 | 2016-10-31 | Merial Inc | Formulaciones inyectables de acción prolongada que comprenden un agente activo isoxazolina, métodos y usos de las mismas |
| LT3298027T (lt) | 2015-05-20 | 2021-08-10 | Boehringer Ingelheim Animal Health USA Inc. | Antihelmintiniai depsipeptido junginiai |
| US20170333305A1 (en) * | 2016-05-23 | 2017-11-23 | Microban Products Company | Topical skin product having retention property |
| WO2018071535A1 (en) | 2016-10-14 | 2018-04-19 | Merial, Inc. | Pesticidal and parasiticidal vinyl isoxazoline compounds |
| CA3044038A1 (en) | 2016-11-16 | 2018-05-24 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic depsipeptide compounds |
| BR112020003217A2 (pt) | 2017-08-14 | 2020-10-06 | Boehringer Ingelheim Animal Health USA Inc. | compostos pesticidas e parasiticidas de pirazolisoxazolina |
| CN111386112A (zh) * | 2017-11-23 | 2020-07-07 | 法国诗华大药厂 | 用于治疗寄生虫感染的含有莫昔克丁的组合物 |
| WO2019118928A1 (en) | 2017-12-15 | 2019-06-20 | Tarsus Pharmaceuticals, Inc. | Isoxazoline parasiticide formulations and methods for treating blepharitis |
| AR113997A1 (es) | 2017-12-21 | 2020-07-08 | Intervet Int Bv | Composiciones antiparasitarias para unción dorsal continua |
| AU2019301510B2 (en) | 2018-07-09 | 2024-06-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Anthelminthic heterocyclic compounds |
| CN113260419A (zh) | 2018-11-20 | 2021-08-13 | 勃林格殷格翰动物保健美国公司 | 吲唑基氰基乙基氨基化合物、其组合物、其制备方法和其使用方法 |
| KR102079347B1 (ko) * | 2018-11-30 | 2020-02-19 | 문현규 | 치과용 유닛 체어 |
| CA3133100A1 (en) | 2019-03-19 | 2020-09-24 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic aza-benzothiophene and aza-benzofuran compounds |
| US12502377B2 (en) | 2019-04-04 | 2025-12-23 | Tarsus Pharmaceuticals, Inc. | Method of eradicating ticks that attach to humans using lotilaner formulations |
| JP7558197B2 (ja) * | 2019-05-03 | 2024-09-30 | インターベット インターナショナル ベー． フェー． | 注射可能な医薬組成物及びその使用 |
| EP4077286A1 (en) | 2019-12-18 | 2022-10-26 | Elanco Tiergesundheit AG | Isoxazoline derivatives as pesticides |
| FR3107531B1 (fr) * | 2020-02-20 | 2022-02-25 | Rl Innovation | .composition liquide ou en gel, ecologique permettant l’enlevement des graffittis, chewing-gums, colles, resines sur tous supports poreux ou non ainsi que tous marquages routier |
| KR20230028268A (ko) | 2020-05-29 | 2023-02-28 | 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 | 구충성 헤테로시클릭 화합물 |
| KR20230043904A (ko) | 2020-07-24 | 2023-03-31 | 엘랑코 유에스 인코포레이티드 | 이속사졸린 화합물 및 이의 중간체의 제조 공정 |
| CH717763A2 (de) | 2020-08-18 | 2022-02-28 | Swibox Ag | Abzweigsystem für elektrische Leiter. |
| CN116744917A (zh) | 2020-09-04 | 2023-09-12 | 礼蓝美国公司 | 适口调配物 |
| JP7824305B2 (ja) | 2021-01-27 | 2026-03-04 | コルテバ アグリサイエンス エルエルシー | 魚における寄生生物に対するシクロプロピルアミド化合物 |
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| JP2025507585A (ja) | 2022-02-17 | 2025-03-21 | ベーリンガー インゲルハイム フェトメディカ ゲーエムベーハー | 流体製品メーラーを提供する方法及びシステム |
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| WO2025191150A2 (en) | 2024-03-15 | 2025-09-18 | Krka, D.D., Novo Mesto | Stable isoxazoline formulation for topical application to the skin |
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