KR20060110344A - 이미다조[1,2-ｂ]피리다진 유도체를 사용하여 동물에서기생충을 방제하는 방법 - Google Patents
이미다조[1,2-ｂ]피리다진 유도체를 사용하여 동물에서기생충을 방제하는 방법 Download PDFInfo
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- KR20060110344A KR20060110344A KR1020067013219A KR20067013219A KR20060110344A KR 20060110344 A KR20060110344 A KR 20060110344A KR 1020067013219 A KR1020067013219 A KR 1020067013219A KR 20067013219 A KR20067013219 A KR 20067013219A KR 20060110344 A KR20060110344 A KR 20060110344A
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agronomy & Crop Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53372903P | 2003-12-31 | 2003-12-31 | |
| US60/533,729 | 2003-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20060110344A true KR20060110344A (ko) | 2006-10-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020067013219A Ceased KR20060110344A (ko) | 2003-12-31 | 2004-12-22 | 이미다조[1,2-ｂ]피리다진 유도체를 사용하여 동물에서기생충을 방제하는 방법 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7759349B2 (https=) |
| EP (1) | EP1699799B1 (https=) |
| JP (1) | JP4758909B2 (https=) |
| KR (1) | KR20060110344A (https=) |
| CN (1) | CN100582108C (https=) |
| AT (1) | ATE362475T1 (https=) |
| AU (1) | AU2004312506B2 (https=) |
| BR (1) | BRPI0418328A (https=) |
| CA (1) | CA2551867C (https=) |
| DE (1) | DE602004006536T2 (https=) |
| ES (1) | ES2285565T3 (https=) |
| NZ (1) | NZ548098A (https=) |
| PL (1) | PL380764A1 (https=) |
| WO (1) | WO2005066177A1 (https=) |
| ZA (1) | ZA200605299B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140019311A (ko) * | 2010-12-22 | 2014-02-14 | 헨그루이 (유에스에이) 엘티디. | 2-아릴이미다조[1,2-b]피리다진, 2-페닐이미다조[1,2-a]피리딘, 및 2-페닐이미다조[1,2-a]피라진 유도체들 |
Families Citing this family (72)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7943160B2 (en) * | 2002-05-09 | 2011-05-17 | Scimetrics Limited Corp. | Pest control methods |
| BRPI0515917A (pt) | 2004-09-23 | 2008-08-12 | Schering Plough Ltd | controle de parasitas em animais pelo uso de novos derivados de éter de oxima de trifluorometanossulfonanilida |
| EP1811841B1 (en) | 2004-11-19 | 2009-10-28 | Schering-Plough Ltd. | Control of parasites in animals by the use of parasiticidal 2-phenyl-3-(1h-pyrrol-2-yl) acrylonitrile derivatives |
| US20080167314A1 (en) * | 2004-12-28 | 2008-07-10 | Osamu Uchikawa | Condensed Imidazole Compound And Use Thereof |
| WO2006135648A2 (en) * | 2005-06-09 | 2006-12-21 | Schering-Plough Ltd. | Control of parasites in animals by n-[(phenyloxy)phenyl]-1,1,1-trifluoromethanesulfonamide and n-[(phenylsulfanyl)phenyl]-1,1,1-trifluoromethanesulfonamide derivatives |
| DE102005042742A1 (de) * | 2005-09-02 | 2007-03-08 | Schering Ag | Substituierte Imidazo[1,2b]pyridazine als Kinase-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel |
| US7750000B2 (en) | 2005-09-02 | 2010-07-06 | Bayer Schering Pharma Ag | Substituted imidazo[1,2b]pyridazines as kinase inhibitors, their preparation and use as medicaments |
| US8119667B2 (en) * | 2005-12-29 | 2012-02-21 | Schering-Plough Animal Health Corporation | Carbonates of fenicol antibiotics |
| TW200803903A (en) * | 2006-04-28 | 2008-01-16 | Nihon Mediphysics Co Ltd | Novel compound having affinity to amyloid |
| RU2008150377A (ru) * | 2006-05-19 | 2010-06-27 | Нихон Меди-Физикс Ко., Лтд. (Jp) | Новое соединение, обладающее сродством к амилоиду |
| CN101501033B (zh) * | 2006-06-21 | 2012-08-01 | 通用电气医疗有限公司 | 对淀粉状蛋白具有亲和性的化合物 |
| DE102006029447A1 (de) * | 2006-06-21 | 2007-12-27 | Bayer Schering Pharma Ag | Oxo-substituierte Imidazo[1,2b]pyridazine, deren Herstellung und Verwendung als Arzneimittel |
| PE20080538A1 (es) * | 2006-08-04 | 2008-06-18 | Takeda Pharmaceutical | Derivado heterociclico fusionado y su uso |
| EP2098522B1 (en) * | 2006-11-30 | 2011-10-19 | Nihon Medi-Physics Co., Ltd. | Compounds having affinity for amyloid |
| CA2672795A1 (en) * | 2006-12-13 | 2008-06-26 | Schering-Plough Ltd. | Water-soluble prodrugs of chloramphenicol, thiamphenicol, and analogs thereof |
| WO2008076259A1 (en) * | 2006-12-13 | 2008-06-26 | Schering-Plough Ltd. | Water-soluble prodrugs of florfenicol and its analogs |
| WO2008072682A1 (ja) * | 2006-12-15 | 2008-06-19 | Daiichi Sankyo Company, Limited | イミダゾ［１，２－ｂ］ピリダジン誘導体 |
| TWI406674B (zh) | 2007-02-13 | 2013-09-01 | 日本藥學物理公司 | Method for manufacturing diagnostic radiographic diagnostic agents |
| WO2008133192A1 (ja) * | 2007-04-19 | 2008-11-06 | Takeda Pharmaceutical Company Limited | 縮合イミダゾール化合物およびその用途 |
| TWI430995B (zh) | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
| KR101769728B1 (ko) | 2007-06-27 | 2017-08-18 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 동물 해충 방제 방법 |
| ES2375425T3 (es) * | 2007-07-26 | 2012-02-29 | Novartis Ag | Compuestos org�?nicos. |
| 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 |
| TW200918102A (en) * | 2007-10-24 | 2009-05-01 | Nihon Mediphysics Co Ltd | Novel compound having affinity for amyloid |
| WO2009057578A1 (ja) * | 2007-10-30 | 2009-05-07 | Nihon Medi-Physics Co., Ltd. | 新規アミロイド親和性化合物の使用及び製造方法 |
| KR20100089858A (ko) * | 2007-10-30 | 2010-08-12 | 니혼 메디피직스 가부시키가이샤 | 신규 아밀로이드 친화성 화합물의 사용 및 제조 방법 |
| US7868001B2 (en) | 2007-11-02 | 2011-01-11 | Hutchison Medipharma Enterprises Limited | Cytokine inhibitors |
| TWI491610B (zh) * | 2008-10-09 | 2015-07-11 | 必治妥美雅史谷比公司 | 作為激酶抑制劑之咪唑并嗒腈 |
| US20120122680A1 (en) | 2009-08-05 | 2012-05-17 | E.I. Du Pont De Nemours And Company | Mesoionic pesticides |
| KR20120050467A (ko) | 2009-08-05 | 2012-05-18 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 메소이온성 살충제 |
| UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| WO2011095581A1 (en) | 2010-02-05 | 2011-08-11 | Intervet International B.V. | S piroindoline compounds for use as anthelminthi cs |
| US8883791B2 (en) | 2010-09-29 | 2014-11-11 | Intervet Inc. | N-heteroaryl compounds with cyclic bridging unit for the treatment of parasitic diseases |
| KR101916481B1 (ko) | 2010-09-29 | 2018-11-07 | 인터벳 인터내셔널 비.브이. | Ｎ-헤테로아릴 화합물 |
| WO2012087630A1 (en) | 2010-12-20 | 2012-06-28 | E.I. Du Pont De Nemours And Company | Pyridine and pyrimidine compounds for controlling invertebrate |
| JP2014520151A (ja) | 2011-06-20 | 2014-08-21 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 蠕虫感染を処置するためのヘテロ環式化合物 |
| WO2013017678A1 (en) | 2011-08-04 | 2013-02-07 | Intervet International B.V. | Novel spiroindoline compounds |
| TW201326128A (zh) | 2011-11-28 | 2013-07-01 | Du Pont | 磺醯胺驅蟲劑 |
| AU2013241854B2 (en) | 2012-03-28 | 2017-11-02 | Intervet International B.V. | Heteroaryl compounds with cyclic bridging unit for use in the treatment helminth infection |
| ES2744597T3 (es) | 2012-03-28 | 2020-02-25 | Intervet Int Bv | Compuestos de heteroarilo con una unidad acíclica como puente |
| WO2013158422A1 (en) | 2012-04-17 | 2013-10-24 | E. I. Du Pont De Nemours And Company | Heterocyclic compounds for controlling invertebrate pests |
| WO2014099837A1 (en) | 2012-12-18 | 2014-06-26 | E. I. Du Pont De Nemours And Company | Sulfonamide anthelmintics |
| CN107810188B (zh) | 2015-04-08 | 2020-09-22 | 拜耳作物科学股份公司 | 作为害虫防治剂和中间体产物的稠合双环杂环衍生物 |
| CA2994604A1 (en) | 2015-08-07 | 2017-02-16 | Bayer Cropscience Aktiengesellschaft | 2-(het)aryl-substituted condensed heterocyclic derivatives as pest control agents |
| MX392191B (es) | 2015-10-26 | 2025-03-21 | Bayer Cropscience Ag | Derivados de heterociclos biciclicos condensados como agentes de control de plagas. |
| WO2017093180A1 (de) | 2015-12-01 | 2017-06-08 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| WO2017144341A1 (de) | 2016-02-23 | 2017-08-31 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| WO2017174414A1 (de) | 2016-04-05 | 2017-10-12 | Bayer Cropscience Aktiengesellschaft | Naphthalin-derivate als schädlingsbekämpfungsmittel |
| EP3241830A1 (de) | 2016-05-04 | 2017-11-08 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| KR102435080B1 (ko) | 2016-07-19 | 2022-08-22 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 해충 방제제로서의 축합 바이시클릭 헤테로사이클 유도체 |
| MA45918A (fr) | 2016-08-15 | 2019-06-19 | Bayer Ag | Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides |
| WO2018050825A1 (de) | 2016-09-19 | 2018-03-22 | Bayer Cropscience Aktiengesellschaft | Pyrazolo[1,5-a]pyridin- derivative und ihre verwendung als schädlingsbekämpfungsmittel |
| WO2018065288A1 (de) | 2016-10-07 | 2018-04-12 | Bayer Cropscience Aktiengesellschaft | 2-[2-phenyl-1-(sulfonylmethyl)vinyl]-imidazo[4,5-b]pyridin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel im pflanzenschutz |
| AU2018208422B2 (en) | 2017-01-10 | 2021-11-11 | Bayer Aktiengesellschaft | Heterocyclene derivatives as pest control agents |
| MX2019008229A (es) | 2017-01-10 | 2019-10-24 | Bayer Ag | Derivados heterociclicos como agentes de control de plagas. |
| GB201700692D0 (en) * | 2017-01-16 | 2017-03-01 | Salvensis | Novel compounds and their use in the treatment of schistosomiasis |
| WO2018138050A1 (de) | 2017-01-26 | 2018-08-02 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| WO2018197257A1 (de) | 2017-04-24 | 2018-11-01 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| EP3305786A3 (de) | 2018-01-22 | 2018-07-25 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| CN111741958A (zh) | 2018-02-21 | 2020-10-02 | 拜耳公司 | 作为害虫防治剂的稠合双环杂环衍生物 |
| WO2020002593A1 (en) | 2018-06-29 | 2020-01-02 | Intervet International B.V. | Compound for use against helminthic infection |
| AU2019301510B2 (en) | 2018-07-09 | 2024-06-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Anthelminthic heterocyclic compounds |
| JP7535532B2 (ja) | 2019-02-26 | 2024-08-16 | バイエル・アクチエンゲゼルシヤフト | 有害生物防除剤としての縮合二環式複素環式誘導体 |
| EP3931193A1 (en) | 2019-02-26 | 2022-01-05 | Bayer Aktiengesellschaft | Fused bicyclic heterocycle derivatives as pesticides |
| CA3133100A1 (en) | 2019-03-19 | 2020-09-24 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic aza-benzothiophene and aza-benzofuran compounds |
| AU2020406093A1 (en) | 2019-12-18 | 2022-06-16 | Intervet International B.V. | Anthelmintic compounds comprising a quinoline structure |
| EP4077322A1 (en) | 2019-12-18 | 2022-10-26 | Intervet International B.V. | Anthelmintic compounds comprising azaindoles structure |
| KR20230028268A (ko) | 2020-05-29 | 2023-02-28 | 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 | 구충성 헤테로시클릭 화합물 |
| US20240043446A1 (en) | 2020-12-11 | 2024-02-08 | Intervet Inc. | Anthelmintic compounds comprising a thienopyridine structure |
| GB202019622D0 (en) * | 2020-12-11 | 2021-01-27 | Adorx Therapeutics Ltd | Antagonist compounds |
| UY39995A (es) | 2021-11-01 | 2023-05-15 | Boehringer Ingelheim Vetmedica GmbH | Compuestos de pirrolopiridazina como antihelmínticos |
| IL326231A (en) | 2023-08-02 | 2026-03-01 | Intervet Int Bv | Carboxamide-4-quinoline compounds with anthelmintic activity |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3725407A (en) * | 1971-04-08 | 1973-04-03 | American Cyanamid Co | 6-substituted amino-3-nitroimidazo(1,2-b)pyridazines and methods of preparing the same |
| US3905974A (en) * | 1972-09-28 | 1975-09-16 | American Cyanamid Co | 6-Substituted oxo and thio-3-nitroimidazo(1,2-b)-pyridazines and methods of preparing same |
| DD157796A5 (de) | 1979-12-04 | 1982-12-08 | Ciba Geigy Ag | Verfahren zur herstellung neuer derivate des 2-amino-aethanols |
-
2004
- 2004-12-22 JP JP2006547394A patent/JP4758909B2/ja not_active Expired - Fee Related
- 2004-12-22 WO PCT/US2004/043402 patent/WO2005066177A1/en not_active Ceased
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- 2004-12-22 AT AT04815474T patent/ATE362475T1/de not_active IP Right Cessation
- 2004-12-22 PL PL380764A patent/PL380764A1/pl not_active Application Discontinuation
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- 2004-12-22 US US11/019,597 patent/US7759349B2/en not_active Expired - Fee Related
- 2004-12-22 KR KR1020067013219A patent/KR20060110344A/ko not_active Ceased
- 2004-12-22 BR BRPI0418328-2A patent/BRPI0418328A/pt not_active IP Right Cessation
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140019311A (ko) * | 2010-12-22 | 2014-02-14 | 헨그루이 (유에스에이) 엘티디. | 2-아릴이미다조[1,2-b]피리다진, 2-페닐이미다조[1,2-a]피리딘, 및 2-페닐이미다조[1,2-a]피라진 유도체들 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE602004006536D1 (de) | 2007-06-28 |
| US20050182059A1 (en) | 2005-08-18 |
| CN1922181A (zh) | 2007-02-28 |
| CN100582108C (zh) | 2010-01-20 |
| DE602004006536T2 (de) | 2008-01-31 |
| CA2551867C (en) | 2010-08-17 |
| ZA200605299B (en) | 2007-03-28 |
| AU2004312506B2 (en) | 2011-08-04 |
| NZ548098A (en) | 2010-05-28 |
| EP1699799B1 (en) | 2007-05-16 |
| JP2007517043A (ja) | 2007-06-28 |
| WO2005066177A1 (en) | 2005-07-21 |
| JP4758909B2 (ja) | 2011-08-31 |
| ES2285565T3 (es) | 2007-11-16 |
| US7759349B2 (en) | 2010-07-20 |
| HK1091207A1 (en) | 2007-01-12 |
| AU2004312506A1 (en) | 2005-07-21 |
| PL380764A1 (pl) | 2007-03-19 |
| CA2551867A1 (en) | 2005-07-21 |
| EP1699799A1 (en) | 2006-09-13 |
| ATE362475T1 (de) | 2007-06-15 |
| BRPI0418328A (pt) | 2007-05-02 |
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