KR20050044451A - 기생충 방제용 벤즈이미다졸- 또는인돌-아미노아세토니트릴 유도체 - Google Patents
기생충 방제용 벤즈이미다졸- 또는인돌-아미노아세토니트릴 유도체 Download PDFInfo
- Publication number
- KR20050044451A KR20050044451A KR1020047007293A KR20047007293A KR20050044451A KR 20050044451 A KR20050044451 A KR 20050044451A KR 1020047007293 A KR1020047007293 A KR 1020047007293A KR 20047007293 A KR20047007293 A KR 20047007293A KR 20050044451 A KR20050044451 A KR 20050044451A
- Authority
- KR
- South Korea
- Prior art keywords
- halo
- alkyl
- alkoxy
- unsubstituted
- alkylthio
- 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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- 150000001875 compounds Chemical class 0.000 claims abstract description 141
- 239000004480 active ingredient Substances 0.000 claims abstract description 46
- 241001465754 Metazoa Species 0.000 claims abstract description 33
- 150000002367 halogens Chemical class 0.000 claims description 93
- 229910052736 halogen Inorganic materials 0.000 claims description 92
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 80
- 229910052739 hydrogen Inorganic materials 0.000 claims description 73
- 239000001257 hydrogen Substances 0.000 claims description 73
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 68
- 150000002431 hydrogen Chemical class 0.000 claims description 62
- 125000001424 substituent group Chemical group 0.000 claims description 62
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- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 16
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 10
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
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- 238000002360 preparation method Methods 0.000 claims description 10
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
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- UTUZBCDXWYMYGA-UHFFFAOYSA-N silafluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC=[Si]2 UTUZBCDXWYMYGA-UHFFFAOYSA-N 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229960000323 triclabendazole Drugs 0.000 description 1
- UGCNRZFAUBJVPT-UHFFFAOYSA-N tricyclohexyltin;hydrate Chemical compound O.C1CCCCC1[Sn](C1CCCCC1)C1CCCCC1 UGCNRZFAUBJVPT-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2103/01 | 2001-11-14 | ||
| CH21032001 | 2001-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050044451A true KR20050044451A (ko) | 2005-05-12 |
Family
ID=4567523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020047007293A Withdrawn KR20050044451A (ko) | 2001-11-14 | 2002-11-13 | 기생충 방제용 벤즈이미다졸- 또는인돌-아미노아세토니트릴 유도체 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7279495B2 (enExample) |
| EP (1) | EP1446386A1 (enExample) |
| JP (1) | JP2005518351A (enExample) |
| KR (1) | KR20050044451A (enExample) |
| CN (1) | CN1304378C (enExample) |
| AR (1) | AR037363A1 (enExample) |
| AU (1) | AU2002351995B2 (enExample) |
| BR (1) | BR0214151A (enExample) |
| CA (1) | CA2466971A1 (enExample) |
| CO (1) | CO5390082A1 (enExample) |
| MX (1) | MXPA04004605A (enExample) |
| NZ (1) | NZ532864A (enExample) |
| RU (1) | RU2004118247A (enExample) |
| TW (1) | TW200300140A (enExample) |
| WO (1) | WO2003042184A1 (enExample) |
| ZA (1) | ZA200403459B (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR042420A1 (es) | 2002-09-11 | 2005-06-22 | Novartis Ag | Benzotriazolil- aminoacetonitril compuestos, proceso para su preparacion, metodo y uso de los mismos en el control de endo- y ecto-parasitos dentro y sobre ganado productor de sangre caliente y animales domesticos y plantas, y en la preparacion de una composicion farmaceutica |
| US20040192738A1 (en) * | 2003-03-18 | 2004-09-30 | Aventis Pharma Deutschland Gmbh | 2-(Butyl-1-sulfonylamino)-N-[1(R)-(6-methoxypyridin-3-yl)propyl] benzamide, its use as a medicament, and pharmaceutical preparations comprising it |
| GB0402677D0 (en) * | 2003-11-06 | 2004-03-10 | Novartis Ag | Organic compounds |
| WO2006043654A1 (ja) * | 2004-10-22 | 2006-04-27 | Nihon Nohyaku Co., Ltd. | アセトニトリル誘導体及び有害生物防除剤並びにその使用方法 |
| KR20080033298A (ko) * | 2005-07-12 | 2008-04-16 | 바이엘 크롭사이언스 소시에떼아노님 | 벤조헤테로시클릴에틸카르복사미드 유도체 |
| TWI387592B (zh) | 2005-08-30 | 2013-03-01 | Novartis Ag | 經取代之苯并咪唑及其作為與腫瘤形成相關激酶之抑制劑之方法 |
| KR101472649B1 (ko) | 2007-05-15 | 2014-12-16 | 메리얼 리미티드 | 아릴로아졸-2-일 시아노에틸아미노 화합물, 이의 제조방법 및 이의 사용방법 |
| AR072297A1 (es) | 2008-06-27 | 2010-08-18 | Novartis Ag | Derivados de indol-2-il-piridin-3-ilo, composicion farmaceutica que los comprende y su uso en medicamentos para el tratamiento de enfermedades mediadas por la sintasa aldosterona. |
| WO2010048191A1 (en) | 2008-10-21 | 2010-04-29 | Merial Limited | Thioamide compounds, method of making and method of using thereof |
| RS58508B1 (sr) | 2008-11-14 | 2019-04-30 | Merial Inc | Enantiomerno obogaćena paraziticidalna jedinjenja ariloazol-2-il cijanoetilamino |
| GB0905365D0 (en) | 2009-03-27 | 2009-05-13 | Norbrook Lab Ltd | A topical parasiticide composition |
| US20100310726A1 (en) | 2009-06-05 | 2010-12-09 | Kraft Foods Global Brands Llc | Novel Preparation of an Enteric Release System |
| US9968564B2 (en) * | 2009-06-05 | 2018-05-15 | Intercontinental Great Brands Llc | Delivery of functional compounds |
| US20100307542A1 (en) * | 2009-06-05 | 2010-12-09 | Kraft Foods Global Brands Llc | Method of Reducing Surface Oil on Encapsulated Material |
| US8859003B2 (en) * | 2009-06-05 | 2014-10-14 | Intercontinental Great Brands Llc | Preparation of an enteric release system |
| MX345971B (es) * | 2012-04-20 | 2017-02-28 | Merial Ltd | Composiciones parasiticidas que comprenden derivados de benzimidazol, metodos y usos de los mismos. |
| US8822689B2 (en) | 2012-09-19 | 2014-09-02 | Merial Limited | Aryloazol-2-yl cyanoethylamino compounds, method of making and method of using thereof |
| US8859005B2 (en) | 2012-12-03 | 2014-10-14 | Intercontinental Great Brands Llc | Enteric delivery of functional ingredients suitable for hot comestible applications |
| WO2015170753A1 (ja) * | 2014-05-08 | 2015-11-12 | 国立大学法人大阪大学 | 熱対流生成用チップ及び液体秤量具 |
| ES2723969T3 (es) | 2014-06-19 | 2019-09-04 | Merial Inc | Composiciones parasiticidas que comprenden derivados de indol, procedimientos y usos de las mismas |
| EP3980414A1 (en) | 2019-06-07 | 2022-04-13 | Elanco Tiergesundheit AG | Bicyclic derivatives for treating endoparasites |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6239077B1 (en) * | 1998-05-01 | 2001-05-29 | Nihon Nohyaku Co., Ltd. | Aminoacetonitrile derivative agricultural and horticultural insecticide containing the same and use thereof |
-
2002
- 2002-11-12 TW TW091133121A patent/TW200300140A/zh unknown
- 2002-11-13 WO PCT/EP2002/012709 patent/WO2003042184A1/en not_active Ceased
- 2002-11-13 KR KR1020047007293A patent/KR20050044451A/ko not_active Withdrawn
- 2002-11-13 AU AU2002351995A patent/AU2002351995B2/en not_active Ceased
- 2002-11-13 CA CA002466971A patent/CA2466971A1/en not_active Abandoned
- 2002-11-13 RU RU2004118247/04A patent/RU2004118247A/ru not_active Application Discontinuation
- 2002-11-13 US US10/494,897 patent/US7279495B2/en not_active Expired - Fee Related
- 2002-11-13 MX MXPA04004605A patent/MXPA04004605A/es unknown
- 2002-11-13 JP JP2003544020A patent/JP2005518351A/ja not_active Withdrawn
- 2002-11-13 AR ARP020104355A patent/AR037363A1/es not_active Application Discontinuation
- 2002-11-13 EP EP02787667A patent/EP1446386A1/en not_active Withdrawn
- 2002-11-13 NZ NZ532864A patent/NZ532864A/xx unknown
- 2002-11-13 BR BR0214151-5A patent/BR0214151A/pt not_active IP Right Cessation
- 2002-11-13 CN CNB028241053A patent/CN1304378C/zh not_active Expired - Fee Related
- 2002-11-14 CO CO02103446A patent/CO5390082A1/es not_active Application Discontinuation
-
2004
- 2004-05-06 ZA ZA200403459A patent/ZA200403459B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1304378C (zh) | 2007-03-14 |
| EP1446386A1 (en) | 2004-08-18 |
| AR037363A1 (es) | 2004-11-03 |
| WO2003042184A1 (en) | 2003-05-22 |
| ZA200403459B (en) | 2006-11-29 |
| US20050026972A1 (en) | 2005-02-03 |
| MXPA04004605A (es) | 2005-03-07 |
| CA2466971A1 (en) | 2003-05-22 |
| US7279495B2 (en) | 2007-10-09 |
| CO5390082A1 (es) | 2004-04-30 |
| RU2004118247A (ru) | 2006-01-10 |
| TW200300140A (en) | 2003-05-16 |
| JP2005518351A (ja) | 2005-06-23 |
| BR0214151A (pt) | 2004-09-14 |
| AU2002351995B2 (en) | 2006-08-10 |
| CN1599725A (zh) | 2005-03-23 |
| NZ532864A (en) | 2005-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20040513 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |