AR091246A1 - Procesos para producir 2-(piridin-3-il)tiazoles - Google Patents
Procesos para producir 2-(piridin-3-il)tiazolesInfo
- Publication number
- AR091246A1 AR091246A1 ARP130101942A AR091246A1 AR 091246 A1 AR091246 A1 AR 091246A1 AR P130101942 A ARP130101942 A AR P130101942A AR 091246 A1 AR091246 A1 AR 091246A1
- Authority
- AR
- Argentina
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- oxy
- aryl
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 7
- 125000001424 substituent group Chemical group 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000005347 halocycloalkyl group Chemical group 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 abstract 2
- -1 C1−6-oxy alkyl Chemical group 0.000 abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 abstract 1
- WPCSNGBKVXKBPU-UHFFFAOYSA-N 2-pyridin-3-yl-1,3-thiazole Chemical class C1=CSC(C=2C=NC=CC=2)=N1 WPCSNGBKVXKBPU-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000001351 cycling effect Effects 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
-
- 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
- C07D213/83—Thioacids; Thioesters; Thioamides; Thioimides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
La presente revelada en este documento se refiere al campo de procesos para producir ciertos 2-(piridin-3-il)tiazoles como intermediarios para la síntesis de tiazolamidas pesticidas. Reivindicación 1: Un proceso que comprende el Esquema 1, (i) hacer reaccionar el compuesto de fórmula (1) con el compuesto de fórmula (2) para producir el compuesto de fórmula (3); seguido de (ii) ciclar el compuesto de fórmula (3) usando un agente deshidratante para producir el compuesto de fórmula (4); en donde (A) cada R¹ está seleccionado, de modo independiente, de H, F, Cl, Br, I, CN, NO₂ y alquilo C₁₋₆ sustituido o no sustituido, en donde cada R¹ sustituido tiene uno o varios sustituyentes seleccionados, de modo independiente, de F, Cl, Br, I, CN, NO₂, alquilo C₁₋₆ y haloalquilo C₁₋₆; (B) R² está seleccionado de alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido, alcoxi C₁₋₆ sustituido o no sustituido, alquenil C₂₋₆-oxi sustituido o no sustituido, cicloalquilo C₃₋₁₀-oxi sustituido o no sustituido, cicloalquenilo C₃₋₁₀-oxi sustituido o no sustituido, arilo C₆₋₂₀-oxi sustituido o no sustituido, alquil C₁₋₆-arilo C₆₋₂₀ sustituido o no sustituido y heterociclilo C₁₋₂₀ sustituido o no sustituido, en donde cada R² sustituido tiene uno o varios sustituyentes seleccionados, de modo independiente, de F, Cl, Br, I, CN, NO₂, alquilo C₁₋₆, alquenilo C₂₋₆, haloalquilo C₁₋₆, haloalquenilo C₂₋₆, haloalquil C₁₋₆-oxi, haloalquenil C₂₋₆-oxi, cicloalquilo C₃₋₁₀, cicloalquenilo C₃₋₁₀, halocicloalquilo C₃₋₁₀, halocicloalquenilo C₃₋₁₀, arilo C₆₋₂₀ y heterociclilo C₁₋₂₀; (C) R³ está seleccionado de H, alquilo C₁₋₆ sustituido o no sustituido, cicloalquilo C₃₋₁₀-oxi sustituido o no sustituido, alquil C₁₋₆-cicloalquilo C₃₋₁₀ sustituido o no sustituido, arilo C₆₋₂₀ sustituido o no sustituido y alquil C₁₋₆-arilo C₆₋₂₀ sustituido o no sustituido, en donde cada R³ sustituido tiene uno o varios sustituyentes seleccionados, de modo independiente, de F, Cl, Br e I; y (D) R⁴ está seleccionado de H, alquilo C₁₋₆ sustituido o no sustituido, cicloalquilo C₃₋₁₀-oxi sustituido o no sustituido, alquil C₁₋₆-cicloalquilo C₃₋₁₀ sustituido o no sustituido, arilo C₆₋₂₀-oxi sustituido o no sustituido, alquil C₁₋₆-arilo C₆₋₂₀ sustituido o no sustituido, alquil C₁₋₆-alquenilo C₂₋₆ sustituido o no sustituido y alquil C₁₋₆-alquinilo C₂₋₆ sustituido o no sustituido, en donde cada uno de dicho R⁴, que está sustituido, tiene uno o varios sustituyentes seleccionados de F, Cl, Br, I, CN, NO₂, alquilo C₁₋₆, haloalquilo C₁₋₆, alquil C₁₋₆-oxi, haloalquil C₁₋₆-oxi, cicloalquilo C₃₋₁₀, halocicloalquilo C₃₋₁₀, arilo C₆₋₂₀ y heterociclilo C₁₋₂₀. Reivindicación 21: Un compuesto que tiene la estructura de fórmula (3) en donde (A) cada R¹ está seleccionado, de modo independiente, de H, F, Cl, Br, I, CN, NO₂ y alquilo C₁₋₆ sustituido o no sustituido, en donde cada R¹ sustituido tiene uno o varios sustituyentes seleccionados, de modo independiente, de F, Cl, Br, I, CN, NO₂, alquilo C₁₋₆ y haloalquilo C₁₋₆; (B) R³ está seleccionado de H, alquilo C₁₋₆ sustituido o no sustituido, cicloalquilo C₃₋₁₀-oxi sustituido o no sustituido, alquil C₁₋₆-cicloalquilo C₃₋₁₀ sustituido o no sustituido, arilo C₆₋₂₀ sustituido o no sustituido y alquil C₁₋₆-arilo C₆₋₂₀ sustituido o no sustituido, en donde cada sustituido R³ tiene uno o varios sustituyentes seleccionados, de modo independiente, de F, Cl, Br e I; y (C) R⁴ está seleccionado de H, alquilo C₁₋₆ sustituido o no sustituido, cicloalquilo C₃₋₁₀-oxi sustituido o no sustituido, alquil C₁₋₆-cicloalquilo C₃₋₁₀ sustituido o no sustituido, arilo C₆₋₂₀-oxi sustituido o no sustituido, alquil C₁₋₆-arilo C₆₋₂₀ sustituido o no sustituido, alquil C₁₋₆-alquenilo C₂₋₆ sustituido o no sustituido y alquil C₁₋₆-alquinilo C₂₋₆ sustituido o no sustituido, en donde cada uno de dicho R⁴, que está sustituido, tiene uno o varios sustituyentes seleccionados de F, Cl, Br, I, CN, NO₂, alquilo C₁₋₆, haloalquilo C₁₋₆, alquil C₁₋₆-oxi, haloalquil C₁₋₆-oxi, cicloalquilo C₃₋₁₀, halocicloalquilo C₃₋₁₀, arilo C₆₋₂₀ y heterociclilo C₁₋₂₀.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261655086P | 2012-06-04 | 2012-06-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR091246A1 true AR091246A1 (es) | 2015-01-21 |
Family
ID=49671038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP130101942 AR091246A1 (es) | 2012-06-04 | 2013-06-03 | Procesos para producir 2-(piridin-3-il)tiazoles |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US9108952B2 (es) |
| EP (1) | EP2855467B1 (es) |
| JP (1) | JP6181166B2 (es) |
| KR (1) | KR102063532B1 (es) |
| CN (1) | CN104507935B (es) |
| AR (1) | AR091246A1 (es) |
| AU (1) | AU2013272007B2 (es) |
| BR (1) | BR112014030091B1 (es) |
| CA (1) | CA2874110C (es) |
| CO (1) | CO7141403A2 (es) |
| HK (1) | HK1208674A1 (es) |
| IL (1) | IL236031A (es) |
| MX (1) | MX349113B (es) |
| NZ (1) | NZ701950A (es) |
| PL (1) | PL2855467T3 (es) |
| RU (1) | RU2647853C2 (es) |
| WO (1) | WO2013184476A2 (es) |
| ZA (1) | ZA201408654B (es) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2576316C2 (ru) | 2010-11-03 | 2016-02-27 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Пестицидная композиция, способ контроля вредителей, способ контроля эндопаразитов, эктопаразитов или обоих и способ усиления жизнестойкости растений |
| KR102006039B1 (ko) | 2011-10-26 | 2019-07-31 | 다우 아그로사이언시즈 엘엘씨 | 살충 조성물 및 그와 관련된 방법 |
| US9282739B2 (en) | 2012-04-27 | 2016-03-15 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| RU2623233C2 (ru) | 2012-04-27 | 2017-06-23 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Пестицидные композиции и относящиеся к ним способы |
| US9708288B2 (en) | 2012-04-27 | 2017-07-18 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| NZ701947A (en) | 2012-06-04 | 2016-04-29 | Dow Agrosciences Llc | Processes to produce certain 2-(pyridine-3-yl)thiazoles |
| RU2647853C2 (ru) | 2012-06-04 | 2018-03-21 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Способы получения определенных 2-(пиридин-3-ил)тиазолов |
| JP2016536295A (ja) | 2013-10-17 | 2016-11-24 | ダウ アグロサイエンシィズ エルエルシー | 有害生物防除性化合物の製造方法 |
| CA2925914A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| KR20160072155A (ko) | 2013-10-17 | 2016-06-22 | 다우 아그로사이언시즈 엘엘씨 | 살충성 화합물의 제조 방법 |
| MX2016004946A (es) | 2013-10-17 | 2016-06-28 | Dow Agrosciences Llc | Procesos para la preparacion de compuestos plaguicidas. |
| MX2016004948A (es) | 2013-10-17 | 2016-06-28 | Dow Agrosciences Llc | Procesos para la preparacion de un compuesto pesticida. |
| 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 |
| CN105636445B (zh) | 2013-10-17 | 2018-12-07 | 美国陶氏益农公司 | 制备杀虫化合物的方法 |
| AR098105A1 (es) | 2013-10-22 | 2016-05-04 | Dow Agrosciences Llc | Composiciones plaguicidas y métodos relacionados |
| RU2656391C2 (ru) | 2013-10-22 | 2018-06-05 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Пестицидные композиции и связанные с ними способы |
| AR098092A1 (es) | 2013-10-22 | 2016-05-04 | Dow Agrosciences Llc | Composiciones plaguicidas sinérgicas y los métodos relacionados |
| AU2014340407B2 (en) | 2013-10-22 | 2017-05-04 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| TWI651049B (zh) | 2013-10-22 | 2019-02-21 | 陶氏農業科學公司 | 殺蟲組成物及相關方法 |
| CN105828611A (zh) | 2013-10-22 | 2016-08-03 | 美国陶氏益农公司 | 协同杀虫组合物和相关方法 |
| MX2016005319A (es) | 2013-10-22 | 2016-08-12 | Dow Agrosciences Llc | Composiciones pesticidas y metodos relacionados. |
| NZ720113A (en) | 2013-10-22 | 2017-06-30 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| US9788546B2 (en) | 2013-10-22 | 2017-10-17 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| US9155304B2 (en) | 2013-10-22 | 2015-10-13 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| KR20160074621A (ko) | 2013-10-22 | 2016-06-28 | 다우 아그로사이언시즈 엘엘씨 | 상승작용적 살충 조성물 및 관련 방법 |
| RU2656888C2 (ru) | 2013-10-22 | 2018-06-07 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Пестицидные композиции и связанные с ними способы |
| CA2927206A1 (en) | 2013-10-22 | 2015-04-30 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| JP2016535022A (ja) | 2013-10-22 | 2016-11-10 | ダウ アグロサイエンシィズ エルエルシー | 農薬組成物および関連する方法 |
| MX2016005308A (es) | 2013-10-22 | 2016-08-08 | Dow Agrosciences Llc | Composiciones pesticidas sinergicas y metodos relacionados. |
| JP2016538265A (ja) | 2013-10-22 | 2016-12-08 | ダウ アグロサイエンシィズ エルエルシー | 相乗的有害生物防除組成物および関連する方法 |
| AR098091A1 (es) | 2013-10-22 | 2016-05-04 | Dow Agrosciences Llc | Composiciones pesticidas sinérgicas y métodos relacionados |
| CA2954345A1 (en) | 2014-07-31 | 2016-02-04 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
| US9249122B1 (en) | 2014-07-31 | 2016-02-02 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine |
| EP3186229A4 (en) | 2014-07-31 | 2018-01-10 | Dow AgroSciences LLC | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
| WO2016028328A1 (en) | 2014-08-19 | 2016-02-25 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
| AR098113A1 (es) | 2014-09-12 | 2016-05-04 | Dow Agrosciences Llc | Proceso para la preparación de 3-(3-cloro-1h-pirazol-1-il)piridina |
| US20180077934A1 (en) | 2015-04-22 | 2018-03-22 | Basf Se | Molluscicide and bait composition comprising a molluscicide |
| US10233155B2 (en) | 2016-12-29 | 2019-03-19 | Dow Agrosciences Llc | Processes for the preparation of pesticide compounds |
| WO2018125815A1 (en) | 2016-12-29 | 2018-07-05 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5219824A (en) * | 1987-02-09 | 1993-06-15 | Monsanto Company | Substituted 2,6-substituted pyridine compounds useful as herbicides |
| RU2083562C1 (ru) * | 1993-02-05 | 1997-07-10 | Исихара Сангио Кайся Лтд. | Производные пиридина, способ их получения, инсектицидная композиция |
| AU5692398A (en) * | 1996-12-09 | 1998-07-03 | Proscript, Inc. | Substituted 5-amino-1,3,4-thiadiazole-2-thiones |
| GB0701426D0 (en) | 2007-01-25 | 2007-03-07 | Univ Sheffield | Compounds and their use |
| UA107791C2 (en) * | 2009-05-05 | 2015-02-25 | Dow Agrosciences Llc | Pesticidal compositions |
| RU2647853C2 (ru) | 2012-06-04 | 2018-03-21 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Способы получения определенных 2-(пиридин-3-ил)тиазолов |
-
2013
- 2013-05-30 RU RU2014153131A patent/RU2647853C2/ru active
- 2013-05-30 US US13/905,220 patent/US9108952B2/en active Active
- 2013-05-30 JP JP2015516068A patent/JP6181166B2/ja active Active
- 2013-05-30 KR KR1020147033734A patent/KR102063532B1/ko active IP Right Grant
- 2013-05-30 WO PCT/US2013/043208 patent/WO2013184476A2/en active Application Filing
- 2013-05-30 CA CA2874110A patent/CA2874110C/en active Active
- 2013-05-30 NZ NZ701950A patent/NZ701950A/en unknown
- 2013-05-30 AU AU2013272007A patent/AU2013272007B2/en active Active
- 2013-05-30 BR BR112014030091-7A patent/BR112014030091B1/pt active IP Right Grant
- 2013-05-30 MX MX2014014882A patent/MX349113B/es active IP Right Grant
- 2013-05-30 PL PL13800850T patent/PL2855467T3/pl unknown
- 2013-05-30 CN CN201380039893.4A patent/CN104507935B/zh active Active
- 2013-05-30 EP EP13800850.3A patent/EP2855467B1/en active Active
- 2013-06-03 AR ARP130101942 patent/AR091246A1/es active IP Right Grant
-
2014
- 2014-11-25 ZA ZA2014/08654A patent/ZA201408654B/en unknown
- 2014-12-02 IL IL236031A patent/IL236031A/en active IP Right Grant
- 2014-12-03 CO CO14265675A patent/CO7141403A2/es unknown
-
2015
- 2015-06-19 US US14/744,673 patent/US20150284377A1/en not_active Abandoned
- 2015-09-23 HK HK15109331.2A patent/HK1208674A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2874110A1 (en) | 2013-12-12 |
| IL236031A (en) | 2016-10-31 |
| CN104507935A (zh) | 2015-04-08 |
| EP2855467B1 (en) | 2016-12-07 |
| US20130324737A1 (en) | 2013-12-05 |
| US9108952B2 (en) | 2015-08-18 |
| HK1208674A1 (en) | 2016-03-11 |
| IL236031A0 (en) | 2015-02-01 |
| NZ701950A (en) | 2016-04-29 |
| AU2013272007A1 (en) | 2014-12-04 |
| JP6181166B2 (ja) | 2017-08-16 |
| AU2013272007B2 (en) | 2017-02-16 |
| EP2855467A2 (en) | 2015-04-08 |
| PL2855467T3 (pl) | 2017-06-30 |
| US20150284377A1 (en) | 2015-10-08 |
| KR20150016297A (ko) | 2015-02-11 |
| MX349113B (es) | 2017-07-12 |
| CN104507935B (zh) | 2016-10-19 |
| WO2013184476A3 (en) | 2014-01-30 |
| JP2015520189A (ja) | 2015-07-16 |
| KR102063532B1 (ko) | 2020-01-09 |
| CO7141403A2 (es) | 2014-12-12 |
| WO2013184476A2 (en) | 2013-12-12 |
| BR112014030091B1 (pt) | 2019-01-15 |
| RU2647853C2 (ru) | 2018-03-21 |
| EP2855467A4 (en) | 2015-12-30 |
| CA2874110C (en) | 2020-07-14 |
| RU2014153131A (ru) | 2016-08-10 |
| ZA201408654B (en) | 2017-06-28 |
| BR112014030091A2 (pt) | 2017-06-27 |
| MX2014014882A (es) | 2015-11-16 |
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