CN106488908A - 制备3‑(3‑氯‑1h‑吡唑‑1‑基)吡啶的方法 - Google Patents

制备3‑(3‑氯‑1h‑吡唑‑1‑基)吡啶的方法 Download PDF

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CN106488908A
CN106488908A CN201480080501.3A CN201480080501A CN106488908A CN 106488908 A CN106488908 A CN 106488908A CN 201480080501 A CN201480080501 A CN 201480080501A CN 106488908 A CN106488908 A CN 106488908A
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pyridine
pyrazol
amino
water
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Q·杨
B·洛尔斯巴赫
C·迪米西斯
A·M·布伊塞
小罗纳德·罗斯
X·李
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Corteva Agriscience LLC
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

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Abstract

通过如下制备3‑(3‑氯‑1H‑吡唑‑1‑基)吡啶：将3‑溴吡啶与商购3‑氨基吡唑偶联，通过重结晶纯化3‑(3‑氨基‑1H‑吡唑‑1‑基)吡啶，并且通过桑德迈尔反应将氨基转化为氯基。

Description

制备3-(3-氯-1H-吡唑-1-基)吡啶的方法
相关申请的交叉引用
本申请要求了以下的2014年7月31日提交的美国临时专利申请序列号62/031,557的权益，在此将其整体内容明确并入本申请中以作参考。
背景技术
本发明涉及改善的制备3-(3-氯-1H-吡唑-1-基)吡啶的方法。
US 20130288893(A1)尤其描述了某些(3-卤-1-(吡啶-3-基)-1H-吡唑-4-基)酰胺和氨基甲酸酯以及它们作为农药的用途。制备这种化合物的途径涉及通过直接偶联3-溴吡啶与3-氯吡唑制备3-(3-氯-1H-吡唑-1-基)吡啶。通过如下制备3-氯吡唑：a)将1H-吡唑用2-二甲基氨磺酰氯和氢化钠处理，得到N,N-二甲基-1H-吡唑-1-磺酰胺，b)将N,N-二甲基-1H-吡唑-1-磺酰胺用六氯乙烷和正丁基锂处理，得到3-氯-N,N-二甲基-1H-吡唑-1-磺酰，c)从3-氯-N,N-二甲基-1H-吡唑-1-磺酰胺用三氟乙酸除去N,N-二甲基磺酰胺，得到3-氯吡唑。
上述披露的方法的收率低，所依赖的起始原料难以制备(3-氯吡唑)，得到的产品难以以纯净物的形式分离。会需要制备3-(3-氯-1H-吡唑-1-基)吡啶(5b)的方法避免这些问题。
发明内容
本发明通过如下提供这样的替换物：将3-溴吡啶与商购3-氨基吡唑偶联，将3-(3-氨基-1H-吡唑-1-基)吡啶(8a)通过重结晶纯化，并且通过桑德迈尔反应将氨基转化为氯基。因此，本发明涉及制备3-(3-氯-1H-吡唑-1-基)吡啶(5b)的方法：
所述方法包括：
a)在约75℃至约155℃的温度在催化量的氯化亚铜(I)和碱的存在下将3-溴吡啶
用3-氨基吡唑
在水混溶性极性非质子有机溶剂中处理，得到3-(3-氨基-1H-吡唑-1-基)吡啶(8a)
b)将3-(3-氨基-1H-吡唑-1-基)吡啶(8a)在水中重结晶；
c)在约0℃至约25℃的温度将3-(3-氨基-1H-吡唑-1-基)吡啶(8a)在含水盐酸中用亚硝酸钠处理，得到重氮盐(8b)
d)在约0℃至约25℃的温度将重氮盐(8b)用氯化铜处理。
具体实施方式
本发明通过如下提供改善的制备3-(3-氯-1H-吡唑-1-基)吡啶(5b)的方法：将3-溴吡啶与商购3-氨基吡唑偶联，将3-(3-氨基-1H-吡唑-1-基)吡啶(8a)通过重结晶纯化，并且通过桑德迈尔反应将氨基转化为氯基。
在第一步中，在约75℃至约155℃的温度在催化量的氯化铜和碱的存在下将3-溴吡啶用3-氨基吡唑在水混溶性极性非质子有机溶剂中偶联，得到3-(3-氨基-1H-吡唑-1-基)吡啶(8a)。尽管需要化学计量的3-溴吡啶和3-氨基吡唑，但经常常规使用过量的3-氨基吡唑。优选过量约10mol％至约50mol％3-氨基吡唑。在约5mol％至约50mol％的氯化铜、优选约15mol％至约30mol％的氯化铜存在下进行偶联。氯化铜可以为氯化亚铜(I)或氯化铜(II)。也在碱的存在下进行偶联。尽管需要化学计量的3-溴吡啶和碱，但经常常规使用约1.5倍至约2倍过量的碱。碱金属碳酸盐为优选的碱。在水混溶性极性非质子有机溶剂中进行偶联。可溶于水的极性非质子有机溶剂包括腈例如乙腈，亚砜例如二甲亚砜，酰胺例如N-甲基吡咯烷酮、N,N-二甲基甲酰胺和N,N-二甲基乙酰胺。特别优选N,N-二甲基甲酰胺。
在常见反应中，在氮气氛下将氯化亚铜(I)、3-氨基吡唑、碳酸钾和N,N-二甲基甲酰胺引入到反应容器中，逐渐加入3-溴吡啶。在约110℃加热混合物直到大多数3-溴吡啶已经反应。允许混合物冷却，在减压下除去大多数溶剂。通过在水中重结晶常规分离和纯化粗制3-(3-氨基-1H-吡唑-1-基)吡啶(8a)。
然后通过如下将纯化的3-(3-氨基-1H-吡唑-1-基)吡啶(8a)转化为需要的3-(3-氯-1H-吡唑-1-基)吡啶(5b)：在约0℃至约25℃的温度在含水盐酸中用亚硝酸钠处理，得到重氮盐，然后在约0℃至约25℃的温度用氯化铜处理重氮盐。尽管需要化学计量的试剂，但经常常规使用相对于3-(3-氨基-1H-吡唑-1-基)吡啶(8a)过量的试剂。因此，使用大大过量的含水盐酸作为反应介质。亚硝酸钠的用量过量约1.5倍至约2倍。氯化铜的用量过量约5mol％至约50mol％，优选过量约15mol％至约30mol％。氯化铜可以为氯化亚铜(I)、氯化铜(II)或铜粉。为了抑制反应期间的发泡，在用氯化铜处理重氮盐期间可加入与水不混溶的有机溶剂例如甲苯或氯仿。
在常见反应中，将3-(3-氨基-1H-吡唑-1-基)吡啶(8a)和含水盐酸的混合物混合并且冷却至约0℃。保持温度低于约5℃，缓慢加入亚硝酸钠水溶液。在约0℃搅拌悬浮液约2小时。在单独的容器中，将氯化亚铜(I)和甲苯的混合物冷却至约0℃，以保持温度低于约5℃的速率加入急冷的重氮盐悬浮液。允许混合物温热至约环境温度。反应完全后，用含水氢氧化钠处理混合物，调节pH到约8至约10。用与水不混溶的有机溶剂萃取所得溶液。除去溶剂后，3-(3-氯-1H-吡唑-1-基)吡啶(5b)可在下一步中直接使用，或通过标准技术例如快速柱色谱法或重结晶进一步纯化。
给出以下实施例说明本发明。
实施例
1.制备3-(3-氨基-1H-吡唑-1-基)吡啶(8a)
在四颈圆底烧瓶(500mL)中装入氯化亚铜(I)(2.51g，25.3mmol)、1H-吡唑-3-胺(15.8g，190mmol)、碳酸钾(35.0g，253mmol)和N,N-二甲基甲酰胺(100mL)。在氮下搅拌混合物10分钟，加入3-溴吡啶(12.2mL，127mmol)。在110℃加热混合物18小时，此时HPLC分析指示剩余约15.5％3-溴吡啶。允许反应冷却至20℃，浓缩，得到棕色残余物。加入水(200mL)，在20℃搅拌所得悬浮液2小时，过滤。将固体用水(2×50mL)漂洗，干燥，得到浅绿色固体。将固体悬浮在水(200mL)中，在90℃加热所得悬浮液2小时，通过垫热过滤。用热水(50mL)漂洗所述垫。允许合并的滤液冷却至20℃，得到黄色悬浮液，在20℃搅拌黄色悬浮液2小时，过滤。将固体用水(2×50mL)漂洗，风干，得到需要的浅黄色结晶固体的产物(11.6g，57％)：mp 169-172℃；1H NMR(400MHz,DMSO-d6)δ9.07–8.82(m,1H)，8.33(dd,J＝4.6,1.5Hz,1H)，8.24(d,J＝2.6Hz,1H)，8.00(ddd,J＝8.4,2.7,1.4Hz,1H)，7.42(ddd,J＝8.5,4.6,0.8Hz,1H)，5.80(d,J＝2.6Hz,1H)，5.21(s,2H)；13C NMR(101MHz,DMSO-d6)δ157.67,144.68,138.00,136.22,128.30,123.95,123.17,97.08；ESIMS m/z 161([M+H]+)。
2.制备3-(3-氯-1H-吡唑-1-基)吡啶(5b)
向三颈圆底烧瓶(100mL)中装入3-(3-氨基-1H-吡唑-1-基)吡啶(0.500g，3.12mmol)和盐酸(37wt％，3mL)。将混合物冷却至0℃，在<5℃分批加入亚硝酸钠(0.431g，6.24mmol)在水(3mL)中的溶液。在0℃搅拌所得黄色悬浮液2小时。向单独的三颈圆底烧瓶(100mL)中装入氯化亚铜(I)(0.371g，3.75mmol)和甲苯(3mL)。将其冷却至0℃，在<5℃分批加入黄色悬浮液。允许所得混合物温热至20℃，搅拌18小时。将其用50％氢氧化钠碱化至pH为10，用乙酸乙酯(2×20mL)萃取。将有机层浓缩至干，将残余物通过快速柱色谱法使用0-10％乙酸乙酯/己烷作为洗脱液纯化。将含有需要产物的馏分浓缩，得到白色固体的标题化合物(0.340g，61％)：mp 104-106℃；1H NMR(400MHz,CDCl3)δ8.93(d,J＝27Hz,1H)，8.57(dd,J＝4.8,1.4Hz,1H)，8.02(ddd,J＝8.3,2.7,1.5Hz,1H)，7.91(d,J＝2.6Hz,1H)，7.47-7.34(M,1H)，6.45(d,J＝2.6Hz,1H)；13C NMR(101MHz,CDCl3)δ148.01,142.72,140.12,135.99,128.64,126.41,124.01,108.08；EIMS m/z 179([M]+)。

Claims (4)

1.制备3-(3-氯-1H-吡唑-1-基)吡啶(5b)的方法：
所述方法包括：
a)在约75℃至约155℃的温度在催化量的氯化铜和碱的存在下将3-溴吡啶
用3-氨基吡唑
在水混溶性极性非质子有机溶剂中处理，得到3-(3-氨基-1H-吡唑-1-基)吡啶(8a)：
b)使3-(3-氨基-1H-吡唑-1-基)吡啶(8a)在水中重结晶；
c)在约0℃至约25℃的温度将3-(3-氨基-1H-吡唑-1-基)吡啶(8a)在含水盐酸中用亚硝酸钠处理，得到重氮盐(8b)：
和
d)在约0℃至约25℃的温度将重氮盐(8b)用氯化铜处理。
2.权利要求1的方法，其中所述水混溶性极性非质子有机溶剂为乙腈、二甲亚砜、N-甲基吡咯烷酮、N,N-二甲基甲酰胺或N,N-二甲基乙酰胺。
3.权利要求2的方法，其中所述水混溶性极性非质子有机溶剂为N,N-二甲基乙酰胺。
4.权利要求1的方法，其中在步骤d)中加入与水不混溶的有机溶剂，抑制发泡。
CN201480080501.3A 2014-07-31 2014-10-17 制备3‑(3‑氯‑1h‑吡唑‑1‑基)吡啶的方法 Pending CN106488908A (zh)

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Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2925954A1 (en) 2013-10-17 2015-04-23 Dow Agrosciences Llc Processes for the preparation of pesticidal compounds
CN105636446B (zh) 2013-10-17 2018-07-13 美国陶氏益农公司 制备杀虫化合物的方法
CA2926095A1 (en) 2013-10-17 2015-04-23 Dow Agrosciences Llc Processes for the preparation of pesticidal compounds
CN105636441B (zh) 2013-10-17 2018-06-15 美国陶氏益农公司 制备杀虫化合物的方法
EP3057425A4 (en) 2013-10-17 2017-08-02 Dow AgroSciences LLC Processes for the preparation of pesticidal compounds
WO2015058022A1 (en) 2013-10-17 2015-04-23 Dow Agrosciences Llc Processes for the preparation of pesticidal compounds
WO2015058021A1 (en) 2013-10-17 2015-04-23 Dow Agrosciences Llc Processes for the preparation of pesticidal compounds
CA2954345A1 (en) 2014-07-31 2016-02-04 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine
WO2016018444A1 (en) 2014-07-31 2016-02-04 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine
AR098110A1 (es) * 2014-07-31 2016-05-04 Dow Agrosciences Llc Proceso para la preparación de 3-(3-cloro-1h-pirazol-1-il)piridina
CA2958058A1 (en) 2014-08-19 2016-02-25 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine
BR112017004613A2 (pt) 2014-09-12 2017-12-05 Dow Agrosciences Llc processo para a preparação de 3-(3-cloro-1h-pirazol-1-il)piridina
US10100033B2 (en) 2016-12-29 2018-10-16 Dow Agrosciences Llc Processes for the preparation of pesticidal compounds
WO2018125817A1 (en) 2016-12-29 2018-07-05 Dow Agrosciences Llc Processes for the preparation of pesticidal compounds
AU2019300171B2 (en) 2018-07-12 2022-09-29 Amsted Rail Company, Inc. Brake monitoring systems for railcars

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4407803A (en) * 1981-08-17 1983-10-04 Abbott Laboratories Antiinflammatory 1-(quinolinyl)-2-pyrazoline derivatives
EP0757987A1 (en) * 1994-04-27 1997-02-12 Nissan Chemical Industries, Limited Pyrazolecarboxylic acid derivative and plant disease control agent
US6965032B2 (en) * 2001-08-13 2005-11-15 E. I. Du Pont De Nemours And Company Substituted dihydro 3-halo-1h-pyrazole-5-carboxylates and their preparation and use
US20060167020A1 (en) * 2002-07-23 2006-07-27 Dickerson Scott H Pyrazolopyrimidines as kinase inhibitors
US20060287541A1 (en) * 2003-09-19 2006-12-21 Ube Industries, Ltd. Method for producing nitrile compound, carboxylic acid compound or carboxylate compound
US20130109566A1 (en) * 2011-10-26 2013-05-02 Dow Agrosciences Llc Pesticidal compositions and processes related thereto
US20130288893A1 (en) * 2012-04-27 2013-10-31 Dow Agrosciences Llc Pesticidal compositions and processes related thereto

Family Cites Families (161)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3597341A (en) 1968-09-11 1971-08-03 Exxon Research Engineering Co Selective addition of thiols to allylic isocyanates and isothiocyanates
CA962269A (en) 1971-05-05 1975-02-04 Robert E. Grahame (Jr.) Thiazoles, and their use as insecticides
FR2517176A1 (fr) 1981-12-01 1983-06-03 Rhone Poulenc Agrochimie Association insecticide et acaricide a base de pyrethroide
ZA831611B (en) * 1982-03-16 1983-11-30 Erba Farmitalia Substituted 1h-pyrazolo(1,5-a)pyrimidines and process for their preparation
US4528291A (en) 1982-06-22 1985-07-09 Schering Corporation 2-(4'-Pyridinyl)-thiazole compounds and their use in increasing cardiac contractility
US4824953A (en) 1983-11-15 1989-04-25 Riker Laboratories, Inc. Multi-step process for producing 5-hydroxy-N-(6-oxo-piperidyl-methyl)-2-(2,2,2-trifluoro-ethoxy)-benzamide and derivatives
IT1183181B (it) 1985-02-07 1987-10-05 Corvi Camillo Spa Derivati del 3-metil-imidazo(4,5-c)pirazolo con attivita' terapeutica e procedimento per la loropreparazione
DE3520328A1 (de) 1985-06-07 1986-12-11 Bayer Ag, 5090 Leverkusen 5-amino-4-heterocyclyl-1-pyridyl-pyrazole
JPS62153273A (ja) 1985-12-26 1987-07-08 Tokuyama Soda Co Ltd ピラゾ−ル化合物
JPS62153273U (zh) 1986-03-19 1987-09-29
DE3618717A1 (de) 1986-06-04 1987-12-10 Bayer Ag 5- acylamino-pyrazol-derivate
JPH07106964B2 (ja) 1987-01-14 1995-11-15 株式会社トクヤマ 摘果剤
US5599944A (en) 1987-03-24 1997-02-04 Bayer Aktiengesellschaft Intermediates for herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur
DE3936622A1 (de) 1989-11-03 1991-05-08 Bayer Ag Halogenierte sulfonylaminocarbonyltriazolinone
JPS63174905U (zh) 1987-04-23 1988-11-14
JPH089541B2 (ja) 1988-03-07 1996-01-31 三井東圧化学株式会社 ピラゾール類を主成分とする脳浮腫抑制剤
US5241074A (en) 1988-05-09 1993-08-31 Bayer Aktiengesellschaft Sulphonylaminocarbonyltriazolinones
US5300480A (en) 1989-04-13 1994-04-05 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyltriazolinones having two substituents bonded via oxygen
US5541337A (en) 1989-04-13 1996-07-30 Bayer Aktiengesellschaft Substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones
US5220028A (en) 1988-10-27 1993-06-15 Nissan Chemical Industries, Ltd. Halogeno-4-methylpyrazoles
US5534486A (en) 1991-04-04 1996-07-09 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyl triazolinones having substituents bonded via oxygen
US5366987A (en) 1991-08-22 1994-11-22 Warner-Lambert Company Isoxazolyl-substituted alkyl amide ACAT inhibitors
TW336932B (en) 1992-12-17 1998-07-21 Pfizer Amino-substituted pyrazoles
WO1997015567A1 (de) 1995-10-20 1997-05-01 Dr. Karl Thomae Gmbh 5-gliedrige heterocyclen, diese verbindungen enthaltende arzneimittel und deren verwendung sowie verfahren zu ihrer herstellung
EP0891356A1 (en) 1996-04-03 1999-01-20 Merck & Co., Inc. Inhibitors of farnesyl-protein transferase
US5854265A (en) 1996-04-03 1998-12-29 Merck & Co., Inc. Biheteroaryl inhibitors of farnesyl-protein transferase
TW430660B (en) 1996-05-30 2001-04-21 Mochida Pharm Co Ltd Novel benzindole derivatives for neuron cell protection, processes for production, and the pharmaceutical compounds containing them
US5854264A (en) 1996-07-24 1998-12-29 Merck & Co., Inc. Inhibitors of farnesyl-protein transferase
WO1998049166A1 (en) 1997-04-25 1998-11-05 Pfizer Limited PYRAZOLOPYRIMIDINONES WHICH INHIBIT TYPE 5 CYCLIC GUANOSINE 3',5'-MONOPHOSPHATE PHOSPHODIESTERASE (cGMP PDE5) FOR THE TREATMENT OF SEXUAL DYSFUNCTION
DE19725450A1 (de) 1997-06-16 1998-12-17 Hoechst Schering Agrevo Gmbh 4-Haloalkyl-3-heterocyclylpyridine und 4-Haloalkyl-5-heterocyclylpyrimidine, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel
US6271237B1 (en) 1997-12-22 2001-08-07 Dupont Pharmaceuticals Company Nitrogen containing heteromatics with ortho-substituted P1s as factor Xa inhabitors
CA2332957A1 (en) 1998-06-05 1999-12-09 Boehringer Ingelheim Pharmaceuticals, Inc. Substituted 1-(4-aminophenyl)pyrazoles and their use as anti-inflammatory agents
GB9827882D0 (en) 1998-12-17 1999-02-10 Smithkline Beecham Plc Novel compounds
KR20020060160A (ko) 1999-08-12 2002-07-16 파마시아 이탈리아 에스.피.에이. 3(5)-아미노-피라졸 유도체, 이의 제조 방법 및항종양제로서의 이의 용도
CA2382676A1 (en) 1999-11-05 2001-05-17 Warner-Lambert Company Prevention of plaque rupture by acat inhibitors
EP1256569B1 (en) 2000-02-16 2010-07-07 Ishihara Sangyo Kaisha, Ltd. Phenacylamine derivatives, production thereof and pest controllers containing the derivatives
GB0011095D0 (en) 2000-05-08 2000-06-28 Black James Foundation astrin and cholecystokinin receptor ligands (III)
US6645990B2 (en) 2000-08-15 2003-11-11 Amgen Inc. Thiazolyl urea compounds and methods of uses
WO2002023986A1 (fr) 2000-08-25 2002-03-28 Sankyo Company, Limited Derives de 4-acylaminopyrazole
AU2001290258A1 (en) 2000-09-22 2002-04-02 Nihon Nohyaku Co. Ltd. N-(4-pyrazolyl)amide derivatives, chemicals for agricultural and horticultural use, and usage of the same
US20020134012A1 (en) 2001-03-21 2002-09-26 Monsanto Technology, L.L.C. Method of controlling the release of agricultural active ingredients from treated plant seeds
CN100540538C (zh) 2001-04-16 2009-09-16 田边三菱制药株式会社 高传导率钙-活化k通道开启剂
EP1256578B1 (en) 2001-05-11 2006-01-11 Pfizer Products Inc. Thiazole derivatives and their use as cdk inhibitors
ATE298749T1 (de) 2001-07-05 2005-07-15 Pfizer Prod Inc Heterocyclo-alkylsulfonyl pyrazole als entzündungshemmende/analgetische mittel
FR2827603B1 (fr) 2001-07-18 2003-10-17 Oreal Composes derives de diaminopyrazole substitues par un radical heteroaromatique et leur utilisation en teinture d'oxydation des fibres keratiniques
GB0123589D0 (en) 2001-10-01 2001-11-21 Syngenta Participations Ag Organic compounds
US7192906B2 (en) 2001-12-20 2007-03-20 Sds Biotech K.K. Substituted pyrazole derivatives, production process thereof, and herbicide compositions containing the derivatives
DE60221627D1 (de) 2001-12-21 2007-09-20 Virochem Pharma Inc Thiazolderivate und ihre Verwendung zur Behandlung oder Vorbeugung von Infektionen durch Flaviviren
US6878196B2 (en) 2002-01-15 2005-04-12 Fuji Photo Film Co., Ltd. Ink, ink jet recording method and azo compound
JP2003212864A (ja) 2002-01-24 2003-07-30 Sankyo Co Ltd ５−（ｍ−シアノベンジルアミノ）チアゾール誘導体
DE60324898D1 (de) 2002-02-25 2009-01-08 Lilly Co Eli Modulatoren von peroxisome proliferator-aktivierten rezeptoren
JP2004051628A (ja) 2002-05-28 2004-02-19 Ishihara Sangyo Kaisha Ltd ピリジン系化合物又はその塩、それらの製造方法及びそれらを含有する除草剤
US6737382B1 (en) 2002-10-23 2004-05-18 Nippon Soda Co. Ltd. Insecticidal aminothiazole derivatives
CA2504320A1 (en) 2002-10-30 2004-05-21 Vertex Pharmaceuticals Incorporated Compositions useful as inhibitors of rock and other protein kinases
ES2436746T3 (es) 2002-12-03 2014-01-07 Merial Limited Derivados pesticidas de 5-(acilamino)pirazol
US7429581B2 (en) 2002-12-23 2008-09-30 Sanofi-Aventis Deutschland Gmbh Pyrazole-derivatives as factor Xa inhibitors
JP4397615B2 (ja) 2003-03-27 2010-01-13 富士フイルム株式会社 インクジェット用インクおよびインクセット
GB0312654D0 (en) 2003-06-03 2003-07-09 Glaxo Group Ltd Therapeutically useful compounds
US7514464B2 (en) 2003-12-18 2009-04-07 Pfizer Limited Substituted arylpyrazoles
US7319108B2 (en) 2004-01-25 2008-01-15 Sanofi-Aventis Deutschland Gmbh Aryl-substituted heterocycles, process for their preparation and their use as medicaments
DE102004003812A1 (de) 2004-01-25 2005-08-11 Aventis Pharma Deutschland Gmbh Arylsubstituierte Heterozyklen, Verfahren ihrer Herstellung und ihre Verwendung als Arzneimittel
US7297168B2 (en) 2004-02-02 2007-11-20 The Procter & Gamble Company Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof
AU2005223483B2 (en) 2004-03-18 2009-04-23 Zoetis Llc N-(1-arylpyrazol-4l)sulfonamides and their use as parasiticides
US20070167426A1 (en) 2004-06-02 2007-07-19 Schering Corporation Compounds for the treatment of inflammatory disorders and microbial diseases
GT200500179A (es) 2004-07-01 2006-02-23 Mezclas sinergistas de agentes de antranilamida para el control de plagas de invertebrados
MX2007002274A (es) 2004-08-23 2007-05-07 Lilly Co Eli Agentes del receptor de histamina h3. preparacion y usos terapeuticos.
EP1794156A2 (en) 2004-09-23 2007-06-13 Pfizer Products Incorporated Trombopoietin receptor agonists
US7923573B2 (en) 2004-10-27 2011-04-12 Daiichi Sankyo Company, Limited Benzene compound having 2 or more substituents
EP2942349A1 (en) 2004-12-23 2015-11-11 Deciphera Pharmaceuticals, LLC Enzyme modulators and treatments
CA2593439C (en) 2005-01-14 2014-02-25 F. Hoffmann-La Roche Ag Thiazole-4-carboxamide derivatives as mglur5 antagonists
US7790720B2 (en) 2005-03-31 2010-09-07 Ucb Pharma, S.A. Compounds comprising an oxazole or thiazole moiety, processes for making them, and their uses
EP1893607A4 (en) * 2005-06-09 2010-07-21 Merck Sharp & Dohme CHECKPOINT KINASE INHIBITORS
BRPI0611798A2 (pt) 2005-06-15 2009-01-13 Pfizer Ltd compostos de arilpirazàis substituÍdos, sua composiÇço farmacÊutica e uso
US7608592B2 (en) 2005-06-30 2009-10-27 Virobay, Inc. HCV inhibitors
KR100654328B1 (ko) 2005-08-26 2006-12-08 한국과학기술연구원 피페라지닐알킬피라졸계 ｔ-타입 칼슘 채널 억제 화합물 및이의 제조방법
BRPI0706610A2 (pt) 2006-01-18 2011-04-05 Siena Biotech Spa moduladores de receptores alfa 7 nicotìnico acetilcolina e usos terapêuticos destes
JP2009524677A (ja) 2006-01-25 2009-07-02 シンタ ファーマシューティカルズ コーポレーション 炎症および免疫関連使用用のチアゾールおよびチアジアゾール化合物
EP2038272B8 (en) 2006-06-30 2013-10-23 Sunesis Pharmaceuticals, Inc. Pyridinonyl pdk1 inhibitors
US20090325956A1 (en) 2006-10-13 2009-12-31 Takahiko Taniguchi Aromatic amine derivative and use thereof
JO2754B1 (en) 2006-12-21 2014-03-15 استرازينكا ايه بي Amylendazoleil derivatives for the treatment of glucocorticoid-mediated disorders
US7795249B2 (en) 2006-12-22 2010-09-14 Millennium Pharmaceuticals, Inc. Certain pyrazoline derivatives with kinase inhibitory activity
GB0701426D0 (en) 2007-01-25 2007-03-07 Univ Sheffield Compounds and their use
US20090069288A1 (en) 2007-07-16 2009-03-12 Breinlinger Eric C Novel therapeutic compounds
AU2008277783B2 (en) 2007-07-17 2012-09-20 F. Hoffmann-La Roche Ag Inhibitors of 11beta-hydroxysteroid dehydrogenase
EP2173728A2 (en) * 2007-07-17 2010-04-14 Amgen Inc. Heterocyclic modulators of pkb
KR101593237B1 (ko) * 2007-07-19 2016-02-12 하. 룬트벡 아크티에 셀스카브 5-원 헤테로시클릭 아미드 및 관련 화합물
US8293919B2 (en) 2007-07-23 2012-10-23 Crestone, Inc. Antibacterial sulfone and sulfoxide substituted heterocyclic urea compounds
CN101918389A (zh) 2007-11-02 2010-12-15 梅特希尔基因公司 组蛋白脱乙酰酶抑制剂
US8389567B2 (en) 2007-12-12 2013-03-05 Calcimedica, Inc. Compounds that modulate intracellular calcium
MX339122B (es) 2008-02-12 2016-05-12 Dow Agrosciences Llc Composiciones pesticidas.
CN101945905B (zh) 2008-02-15 2013-06-26 旭化成电子材料株式会社 树脂组合物
CA2719847A1 (en) 2008-04-21 2010-01-28 Merck Sharp & Dohme Corp. Inhibitors of janus kinases
BRPI0915350A2 (pt) 2008-06-13 2016-05-03 Bayer Cropscience Ag novas amidas e tioamidas heteroatômicas como pesticidas
TW201004941A (en) 2008-07-16 2010-02-01 Wyeth Corp Alpha7 nicotinic acetylcholine receptor inhibitors
ES2567183T3 (es) 2008-07-17 2016-04-20 Bayer Cropscience Ag Compuestos heterocíclicos como pesticidas
JP2010030970A (ja) 2008-07-31 2010-02-12 Bayer Cropscience Ag 殺虫性ベンゼンジカルボキサミド誘導体
CA2737437A1 (en) 2008-09-19 2010-03-25 Absolute Science, Inc. Methods of treating a botulinum toxin related condition in a subject
WO2010032874A1 (ja) 2008-09-19 2010-03-25 住友化学株式会社 農業用組成物
CN102186825A (zh) 2008-10-21 2011-09-14 麦它波莱克斯股份有限公司 芳基gpr120受体激动剂和其用途
CN101747276B (zh) 2008-11-28 2011-09-07 中国中化股份有限公司 具有含氮五元杂环的醚类化合物及其应用
CN102264737A (zh) 2008-12-23 2011-11-30 雅培制药有限公司 抗病毒化合物
JP5894438B2 (ja) 2009-02-11 2016-03-30 ダウ アグロサイエンシィズ エルエルシー 殺虫性組成物
US8785468B2 (en) 2009-02-13 2014-07-22 Amgen Inc. Phenylalanine amide derivatives useful for treating insulin-related diseases and conditions
UA107791C2 (en) 2009-05-05 2015-02-25 Dow Agrosciences Llc Pesticidal compositions
BRPI1010909A2 (pt) 2009-05-19 2015-09-08 Bayer Cropscience Ag "inseticida arilpirrolinas"
FI20095678A0 (fi) 2009-06-16 2009-06-16 Biotie Therapies Oy Ureasubstituoituja sulfoniamidijohdannaisia
UA110324C2 (en) 2009-07-02 2015-12-25 Genentech Inc Jak inhibitory compounds based on pyrazolo pyrimidine
CN102471252B (zh) 2009-08-10 2014-07-02 住友化学株式会社 (氟烷基硫基)乙酸酯的制造方法
JP2012254939A (ja) 2009-10-07 2012-12-27 Astellas Pharma Inc オキサゾール化合物
BR112012006956A2 (pt) 2009-10-12 2015-09-15 Bayer Cropscience Ag 1- (pirida-3-il) -pirazóisol e 1- (pirimida-5-il) - pirazóisol como pesticidas
MX2012003376A (es) 2009-10-12 2012-06-27 Bayer Cropscience Ag Amidas y tioamidas como agentes para combatir parasitos.
US8883785B2 (en) 2010-01-25 2014-11-11 Chdi Foundation, Inc. Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof
EP2539330B1 (en) 2010-02-22 2016-11-09 Syngenta Participations AG Dihydrofuran derivatives as insecticidal compounds
CN104940200B (zh) 2010-03-30 2019-06-28 维颂公司 多取代芳族化合物作为凝血酶的抑制剂
JP5826822B2 (ja) 2010-04-16 2015-12-02 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ 有害生物防除薬としての新規な複素環化合物
EP2382865A1 (de) 2010-04-28 2011-11-02 Bayer CropScience AG Synergistische Wirkstoffkombinationen
CN102971315B (zh) 2010-05-05 2015-07-22 拜耳知识产权有限责任公司 作为害虫防治剂的噻唑衍生物
EP2585467B1 (en) 2010-06-24 2016-03-02 Gilead Sciences, Inc. Pyrazolo[1,5-a]pyrimidines and -triazines as antiviral agents
BR112012033411A2 (pt) 2010-06-28 2015-09-15 Bayer Ip Gmbh compostos heterocíclicos como pesticidas
US20130109682A1 (en) 2010-07-06 2013-05-02 Novartis Ag Cyclic ether compounds useful as kinase inhibitors
EP2593447B1 (de) 2010-07-15 2016-08-17 Bayer Intellectual Property GmbH 3-pyridyl-heteroarylcarboxamidverbindungen als schädlingsbekämpfungsmittel
CA2808234A1 (en) * 2010-08-31 2012-03-08 Dow Agrosciences Llc Pesticidal compositions
JP2012082186A (ja) 2010-09-15 2012-04-26 Bayer Cropscience Ag 殺虫性アリールピロリジン類
JP5953308B2 (ja) 2010-10-22 2016-07-20 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ 殺害虫剤としての新規ヘテロ環式化合物
CN103281901B (zh) 2010-11-03 2016-12-28 陶氏益农公司 杀虫组合物和与其相关的方法
WO2012061290A2 (en) 2010-11-03 2012-05-10 Dow Agrosciences Llc Pesticidal compositions and processes related thereto
WO2012070114A1 (ja) 2010-11-24 2012-05-31 塩野義製薬株式会社 Ｎｐｙ ｙ５受容体拮抗作用を有するスルファミド誘導体
JPWO2012102387A1 (ja) 2011-01-27 2014-07-03 日産化学工業株式会社 ピラゾール誘導体及び有害生物防除剤
JPWO2012108511A1 (ja) 2011-02-09 2014-07-03 日産化学工業株式会社 ピラゾール誘導体および有害生物防除剤
JP2012188418A (ja) 2011-02-22 2012-10-04 Nissan Chem Ind Ltd トリアゾ−ル誘導体及び有害生物防除剤
TW201238487A (en) 2011-02-25 2012-10-01 Dow Agrosciences Llc Pesticidal compositions and processes related thereto
JP2013107867A (ja) 2011-04-21 2013-06-06 Nissan Chem Ind Ltd ピラゾール誘導体及び有害生物防除剤
WO2012147107A2 (en) 2011-04-29 2012-11-01 Msn Laboratories Limited Novel & improved processes for the preparation of indoline derivatives and its pharmaceutical composition
EP2532661A1 (en) 2011-06-10 2012-12-12 Syngenta Participations AG Novel insecticides
EP2540718A1 (en) 2011-06-29 2013-01-02 Syngenta Participations AG. Novel insecticides
EA201400138A1 (ru) 2011-07-15 2014-06-30 Басф Се Пестицидные способы применения замещенных 3-пиридилтиазольных соединений и производных для борьбы с животными-вредителями ii
JP2013075871A (ja) 2011-09-30 2013-04-25 Nissan Chem Ind Ltd チアゾール誘導体および有害生物防除剤
JP2013082699A (ja) 2011-09-30 2013-05-09 Nissan Chem Ind Ltd ピラゾール誘導体および有害生物防除剤
JP2013082704A (ja) 2011-09-30 2013-05-09 Nissan Chem Ind Ltd チアゾール誘導体および有害生物防除剤
US20140296068A1 (en) 2011-10-26 2014-10-02 Dow Agrosciences Llc Pesticidal compositions and processes related thereto
DE102011085492A1 (de) 2011-10-31 2013-05-02 Evonik Goldschmidt Gmbh Neue aminogruppenhaltige Siloxane, Verfahren zu deren Herstellung und Anwendung
JP2013129653A (ja) 2011-11-22 2013-07-04 Nissan Chem Ind Ltd トリアゾ−ル誘導体および有害生物防除剤
JP2013129651A (ja) 2011-11-22 2013-07-04 Nissan Chem Ind Ltd チアゾール誘導体および有害生物防除剤
WO2013156433A1 (en) 2012-04-17 2013-10-24 Syngenta Participations Ag Insecticidally active thiazole derivatives
WO2013156431A1 (en) 2012-04-17 2013-10-24 Syngenta Participations Ag Pesticidally active pyridyl- and pyrimidyl- substituted thiazole and thiadiazole derivatives
BR112014030091B1 (pt) 2012-06-04 2019-01-15 Dow Agrosciences Llc processos para produzir certos 2-(piridina-3-il)tiazóis
US9198428B2 (en) 2012-06-04 2015-12-01 Dow Agrosciences, Llc. Processes to produce certain 2-(pyridine-3-yl)thiazoles
EP2934536B1 (en) * 2012-12-19 2017-09-27 Merck Sharp & Dohme Corp. FACTOR IXa INHIBITORS
US9108932B2 (en) 2013-03-13 2015-08-18 Dow Agrosciences Llc Preparation of haloalkoxyarylhydrazines and intermediates therefrom
WO2015058022A1 (en) 2013-10-17 2015-04-23 Dow Agrosciences Llc Processes for the preparation of pesticidal compounds
CA2925954A1 (en) 2013-10-17 2015-04-23 Dow Agrosciences Llc Processes for the preparation of pesticidal compounds
EP3057425A4 (en) 2013-10-17 2017-08-02 Dow AgroSciences LLC Processes for the preparation of pesticidal compounds
CA2926095A1 (en) 2013-10-17 2015-04-23 Dow Agrosciences Llc Processes for the preparation of pesticidal compounds
CN105636441B (zh) 2013-10-17 2018-06-15 美国陶氏益农公司 制备杀虫化合物的方法
WO2015058021A1 (en) * 2013-10-17 2015-04-23 Dow Agrosciences Llc Processes for the preparation of pesticidal compounds
CN105636446B (zh) 2013-10-17 2018-07-13 美国陶氏益农公司 制备杀虫化合物的方法
WO2016018444A1 (en) 2014-07-31 2016-02-04 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine
AR098110A1 (es) * 2014-07-31 2016-05-04 Dow Agrosciences Llc Proceso para la preparación de 3-(3-cloro-1h-pirazol-1-il)piridina
CA2954345A1 (en) 2014-07-31 2016-02-04 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine
CA2958058A1 (en) 2014-08-19 2016-02-25 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine
BR112017004613A2 (pt) 2014-09-12 2017-12-05 Dow Agrosciences Llc processo para a preparação de 3-(3-cloro-1h-pirazol-1-il)piridina

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4407803A (en) * 1981-08-17 1983-10-04 Abbott Laboratories Antiinflammatory 1-(quinolinyl)-2-pyrazoline derivatives
EP0757987A1 (en) * 1994-04-27 1997-02-12 Nissan Chemical Industries, Limited Pyrazolecarboxylic acid derivative and plant disease control agent
US6965032B2 (en) * 2001-08-13 2005-11-15 E. I. Du Pont De Nemours And Company Substituted dihydro 3-halo-1h-pyrazole-5-carboxylates and their preparation and use
US20060167020A1 (en) * 2002-07-23 2006-07-27 Dickerson Scott H Pyrazolopyrimidines as kinase inhibitors
US20060287541A1 (en) * 2003-09-19 2006-12-21 Ube Industries, Ltd. Method for producing nitrile compound, carboxylic acid compound or carboxylate compound
US20130109566A1 (en) * 2011-10-26 2013-05-02 Dow Agrosciences Llc Pesticidal compositions and processes related thereto
US20130288893A1 (en) * 2012-04-27 2013-10-31 Dow Agrosciences Llc Pesticidal compositions and processes related thereto

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