RU2018144344A - Синтез 6-арил-4-аминопиколинатов и 2-арил-6-аминопиримидин-4-карбоксилатов прямым сочетанием сузуки - Google Patents
Синтез 6-арил-4-аминопиколинатов и 2-арил-6-аминопиримидин-4-карбоксилатов прямым сочетанием сузуки Download PDFInfo
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- RU2018144344A RU2018144344A RU2018144344A RU2018144344A RU2018144344A RU 2018144344 A RU2018144344 A RU 2018144344A RU 2018144344 A RU2018144344 A RU 2018144344A RU 2018144344 A RU2018144344 A RU 2018144344A RU 2018144344 A RU2018144344 A RU 2018144344A
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- Prior art keywords
- paragraphs
- catalyst
- alkyl
- alkoxy
- suzuki
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- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 73
- 239000003054 catalyst Substances 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 15
- 150000003927 aminopyridines Chemical class 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 229910052736 halogen Chemical group 0.000 claims 10
- 150000002367 halogens Chemical group 0.000 claims 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 9
- 238000006069 Suzuki reaction reaction Methods 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims 8
- 150000001543 aryl boronic acids Chemical class 0.000 claims 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052763 palladium Inorganic materials 0.000 claims 6
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical group [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims 6
- 239000012035 limiting reagent Substances 0.000 claims 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- GDJCQSNQOHRAGY-UHFFFAOYSA-N (4-chloro-2-fluoro-3-methoxyphenyl)boronic acid Chemical compound COC1=C(Cl)C=CC(B(O)O)=C1F GDJCQSNQOHRAGY-UHFFFAOYSA-N 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- -1 dimethyl (4-chloro-2-fluoro-3-methoxyphenyl) boronate Chemical compound 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- WHKVMIKJUDLXNI-UHFFFAOYSA-N [7-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indol-1-yl]-tri(propan-2-yl)silane Chemical compound FC1=C2N([Si](C(C)C)(C(C)C)C(C)C)C=CC2=CC=C1B1OC(C)(C)C(C)(C)O1 WHKVMIKJUDLXNI-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 150000005005 aminopyrimidines Chemical class 0.000 claims 1
- 125000000262 haloalkenyl group Chemical group 0.000 claims 1
- FRMBCYILCYTPHY-UHFFFAOYSA-N methyl 4-amino-3,6-dichloropyridine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=CC(N)=C1Cl FRMBCYILCYTPHY-UHFFFAOYSA-N 0.000 claims 1
- YEUYMEGMXJWEDE-UHFFFAOYSA-N methyl 6-amino-2,5-dichloropyrimidine-4-carboxylate Chemical compound COC(=O)C1=NC(Cl)=NC(N)=C1Cl YEUYMEGMXJWEDE-UHFFFAOYSA-N 0.000 claims 1
- VHXVXHHVPQJMFM-UHFFFAOYSA-N methyl 6-amino-2-chloro-5-methoxypyrimidine-4-carboxylate Chemical compound COC(=O)C1=NC(Cl)=NC(N)=C1OC VHXVXHHVPQJMFM-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- 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
- C07D401/02—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 containing two hetero rings
- C07D401/04—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 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/391—Physical properties of the active metal ingredient
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/90—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having more than three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
- B01J2231/4211—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662338562P | 2016-05-19 | 2016-05-19 | |
| US62/338562 | 2016-05-19 | ||
| US201662416811P | 2016-11-03 | 2016-11-03 | |
| US62/416811 | 2016-11-03 | ||
| PCT/US2017/033489 WO2017201377A1 (en) | 2016-05-19 | 2017-05-19 | Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct suzuki coupling |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2018144344A true RU2018144344A (ru) | 2020-06-19 |
| RU2018144344A3 RU2018144344A3 (enExample) | 2021-02-18 |
Family
ID=60326419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2018144344A RU2018144344A (ru) | 2016-05-19 | 2017-05-19 | Синтез 6-арил-4-аминопиколинатов и 2-арил-6-аминопиримидин-4-карбоксилатов прямым сочетанием сузуки |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US10087164B2 (enExample) |
| EP (1) | EP3458442B1 (enExample) |
| JP (2) | JP7113762B2 (enExample) |
| KR (1) | KR20190007048A (enExample) |
| CN (1) | CN109415319A (enExample) |
| AU (2) | AU2017268424B2 (enExample) |
| BR (1) | BR112018073348B8 (enExample) |
| CA (1) | CA3023935A1 (enExample) |
| IL (1) | IL263075A (enExample) |
| MX (1) | MX2018014174A (enExample) |
| RU (1) | RU2018144344A (enExample) |
| WO (1) | WO2017201377A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2017268424B2 (en) * | 2016-05-19 | 2021-07-15 | Corteva Agriscience Llc | Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct suzuki coupling |
| EP3853205A1 (en) | 2018-09-19 | 2021-07-28 | Corteva Agriscience LLC | Preparation of halogen analogs of picloram |
| WO2020133403A1 (zh) * | 2018-12-29 | 2020-07-02 | 青岛清原化合物有限公司 | 取代的嘧啶芳酯衍生物及其制备方法、除草组合物和应用 |
| BR112022018508A2 (pt) | 2020-03-18 | 2022-10-25 | Corteva Agriscience Llc | Síntese melhorada de 4-amino-6-(heterocíclico)picolinatos |
| US20230174490A1 (en) | 2020-03-18 | 2023-06-08 | Corteva Agriscience Llc | Improved synthesis of 6-aryl-4-aminopicolinates |
| EP4149926A1 (en) * | 2020-05-11 | 2023-03-22 | Corteva Agriscience LLC | Preparation of compounds having pesticidal activity |
| WO2023248174A1 (en) * | 2022-06-22 | 2023-12-28 | Hetero Labs Limited | An improved process for preparation of voxelotor |
| CN115819334B (zh) * | 2022-06-28 | 2025-03-18 | 安徽众邦生物工程有限公司 | 一种氯氟吡啶酯的制备方法 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR037228A1 (es) | 2001-07-30 | 2004-11-03 | Dow Agrosciences Llc | Compuestos del acido 6-(aril o heteroaril)-4-aminopicolinico, composicion herbicida que los comprende y metodo para controlar vegetacion no deseada |
| WO2007082076A1 (en) * | 2006-01-13 | 2007-07-19 | Dow Agrosciences Llc | 2-(poly-substituted aryl)-6-amino-5-halo-4-pyrimidinecarboxylic acids and their use as herbicides |
| PL2311815T3 (pl) * | 2007-08-13 | 2013-05-31 | Dow Agrosciences Llc | 2-(2-fluoro-podstawiony fenyl)-6-amino-5-chloro-4-pirymidyno-karboksylany i ich zastosowanie jako herbicydów |
| DE602008005319D1 (de) * | 2007-08-30 | 2011-04-14 | Dow Agrosciences Llc | 2-(substituierte phenyl)-6-amino-5-alkoxy-, thioalkoxy- und aminoalkyl-4-pyrimidincarboxylate und ihre verwendung als herbizide |
| EP2327694B1 (en) * | 2007-10-02 | 2013-07-24 | Dow AgroSciences LLC | Substituted 4-amino-picolinic acids and their use as herbicides |
| PL2279178T3 (pl) * | 2008-04-18 | 2015-10-30 | Dow Agrosciences Llc | 2-(podstawione-fenylo)-6-hydroksy- lub alkoksy-5-podstawione-4 pirymidynokarboksylany i ich zastosowanie jako herbicydów |
| GB0808664D0 (en) * | 2008-05-13 | 2008-06-18 | Syngenta Ltd | Chemical compounds |
| GB0902474D0 (en) * | 2009-02-13 | 2009-04-01 | Syngenta Ltd | Chemical compounds |
| GB0907625D0 (en) * | 2009-05-01 | 2009-06-10 | Syngenta Ltd | Method of controlling undesired vegetation |
| AU2012209287B2 (en) * | 2011-01-25 | 2015-09-03 | Dow Agrosciences Llc | 6-amino-2-substituted-5-vinylsilylpyrimidine-4-carboxylic acids and esters and 4-amino-6-substituted-3-vinylsilylpyridine-2-carboxylic acids and esters as herbicides |
| TWI520943B (zh) * | 2011-01-25 | 2016-02-11 | 陶氏農業科學公司 | 用於製備４－胺基－３－氯－５－氟－６－（經取代的）吡啶甲酸酯的方法（二） |
| TWI592401B (zh) | 2011-01-25 | 2017-07-21 | 陶氏農業科學公司 | 用於製備４－胺基－３－氯－５－氟－６－（經取代的）吡啶甲酸酯的方法（一） |
| TWI529163B (zh) * | 2011-01-25 | 2016-04-11 | 陶氏農業科學公司 | 用於製備４－胺基－５－氟－３－鹵素－６－（經取代之）吡啶甲酸酯的方法 |
| RU2612301C2 (ru) * | 2011-07-27 | 2017-03-06 | Байер Интеллектуэль Проперти Гмбх | Замещенные пиколиновые и пиримидин-4-карбоновые кислоты, способ их получения и их применение в качестве гербицидов и регуляторов роста растений |
| MX356476B (es) | 2011-12-30 | 2018-05-30 | Dow Agrosciences Llc | Métodos para aislar 4-cloro-2-fluor-3-fenil boronatos sustituidos y métodos para su uso. |
| EP2797890B1 (en) * | 2011-12-30 | 2016-10-05 | Dow AgroSciences LLC | Methods of producing methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate |
| AR091856A1 (es) * | 2012-07-24 | 2015-03-04 | Dow Agrosciences Llc | Proceso para la preparacion de 4-amino-5-fluor-3-halo-6-(substituido) picolinatos |
| CN102875456B (zh) * | 2012-10-23 | 2013-12-11 | 西华大学 | 3,6-二氯-2-氨基吡啶的化学合成方法 |
| US20140170058A1 (en) | 2012-12-13 | 2014-06-19 | Dow Agrosciences Llc | Process for the removal of palladium from 4-amino-3-halo-5-fluoro-6-(aryl) pyridine-2-carboxylates and 4-amino-3-halo-6-(aryl)pyridine-2-carboxylates |
| US9637505B2 (en) * | 2013-03-15 | 2017-05-02 | Dow Agrosciences Llc | 4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their use as herbicides |
| CN105208859A (zh) * | 2013-03-15 | 2015-12-30 | 美国陶氏益农公司 | 作为除草剂的新型的4-氨基吡啶和6-氨基嘧啶羧酸酯 |
| US9113629B2 (en) | 2013-03-15 | 2015-08-25 | Dow Agrosciences Llc | 4-amino-6-(4-substituted-phenyl)-picolinates and 6-amino-2-(4-substituted-phenyl)-pyrimidine-4-carboxylates and their use as herbicides |
| EP2970185B1 (en) * | 2013-03-15 | 2023-07-12 | Corteva Agriscience LLC | 4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their use as herbicides |
| WO2014151009A1 (en) | 2013-03-15 | 2014-09-25 | Dow Agrosciences Llc | 4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic) pyrimidine-4-carboxylates and their use as herbicides |
| AU2017268424B2 (en) * | 2016-05-19 | 2021-07-15 | Corteva Agriscience Llc | Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct suzuki coupling |
-
2017
- 2017-05-19 AU AU2017268424A patent/AU2017268424B2/en not_active Ceased
- 2017-05-19 WO PCT/US2017/033489 patent/WO2017201377A1/en not_active Ceased
- 2017-05-19 BR BR112018073348A patent/BR112018073348B8/pt active IP Right Grant
- 2017-05-19 JP JP2018560490A patent/JP7113762B2/ja active Active
- 2017-05-19 MX MX2018014174A patent/MX2018014174A/es unknown
- 2017-05-19 KR KR1020187036364A patent/KR20190007048A/ko not_active Abandoned
- 2017-05-19 EP EP17800225.9A patent/EP3458442B1/en active Active
- 2017-05-19 CA CA3023935A patent/CA3023935A1/en active Pending
- 2017-05-19 CN CN201780042463.6A patent/CN109415319A/zh active Pending
- 2017-05-19 RU RU2018144344A patent/RU2018144344A/ru unknown
- 2017-05-19 US US15/599,716 patent/US10087164B2/en active Active
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2018
- 2018-07-26 US US16/045,896 patent/US10544121B2/en active Active
- 2018-07-26 US US16/045,901 patent/US10570114B2/en active Active
- 2018-11-18 IL IL263075A patent/IL263075A/en unknown
-
2021
- 2021-05-20 AU AU2021203233A patent/AU2021203233A1/en not_active Abandoned
-
2022
- 2022-07-26 JP JP2022118930A patent/JP2022141912A/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US20170334878A1 (en) | 2017-11-23 |
| BR112018073348B8 (pt) | 2023-05-16 |
| JP2022141912A (ja) | 2022-09-29 |
| EP3458442A4 (en) | 2020-04-22 |
| BR112018073348B1 (pt) | 2023-01-24 |
| IL263075A (en) | 2018-12-31 |
| AU2021203233A1 (en) | 2021-06-10 |
| WO2017201377A1 (en) | 2017-11-23 |
| CA3023935A1 (en) | 2017-11-23 |
| RU2018144344A3 (enExample) | 2021-02-18 |
| US10544121B2 (en) | 2020-01-28 |
| MX2018014174A (es) | 2019-03-14 |
| JP7113762B2 (ja) | 2022-08-05 |
| KR20190007048A (ko) | 2019-01-21 |
| US10570114B2 (en) | 2020-02-25 |
| BR112018073348A2 (pt) | 2019-03-06 |
| NZ747932A (en) | 2022-03-25 |
| JP2019516708A (ja) | 2019-06-20 |
| AU2017268424A1 (en) | 2018-11-22 |
| EP3458442B1 (en) | 2022-12-28 |
| US20180334444A1 (en) | 2018-11-22 |
| AU2017268424B2 (en) | 2021-07-15 |
| US20180334445A1 (en) | 2018-11-22 |
| CN109415319A (zh) | 2019-03-01 |
| EP3458442A1 (en) | 2019-03-27 |
| US10087164B2 (en) | 2018-10-02 |
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