AR107418A1 - Proceso para la preparación de ácidos 4-alcoxi-3-hidroxipicolínicos - Google Patents
Proceso para la preparación de ácidos 4-alcoxi-3-hidroxipicolínicosInfo
- Publication number
- AR107418A1 AR107418A1 ARP170100174A ARP170100174A AR107418A1 AR 107418 A1 AR107418 A1 AR 107418A1 AR P170100174 A ARP170100174 A AR P170100174A AR P170100174 A ARP170100174 A AR P170100174A AR 107418 A1 AR107418 A1 AR 107418A1
- Authority
- AR
- Argentina
- Prior art keywords
- mixture
- compound
- formula
- separating
- mineral acid
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 5
- 238000002360 preparation method Methods 0.000 title abstract 4
- 150000007513 acids Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 abstract 28
- 150000001875 compounds Chemical class 0.000 abstract 16
- -1 amine salt Chemical class 0.000 abstract 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- 229910052794 bromium Inorganic materials 0.000 abstract 4
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 4
- 239000011707 mineral Substances 0.000 abstract 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 abstract 2
- 229910017604 nitric acid Inorganic materials 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 239000007800 oxidant agent Substances 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- 235000011007 phosphoric acid Nutrition 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 101001122476 Homo sapiens Mu-type opioid receptor Proteins 0.000 abstract 1
- 102100028647 Mu-type opioid receptor Human genes 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 238000005576 amination reaction Methods 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000010641 nitrile hydrolysis reaction Methods 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- 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
- C07D213/84—Nitriles
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
-
- 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
- C07D213/02—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
- C07D213/803—Processes of preparation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Abstract
Los ácidos 4-alcoxi-3-hidroxipicolínicos pueden prepararse convenientemente a partir de 4,6-dibromo-3-hidroxipicolinonitrilo en una serie de etapas químicas seleccionadas de la sustitución de bromo, hidrólisis del nitrilo y reducción de halógeno que se realizan en un proceso en un único recipiente. El 4,6-dibromo-3-hidroxipicolinonitrilo puede prepararse a partir del furfural en una serie de etapas químicas que se seleccionan de la aminación del ciano, la formación de sal de amina y la brotación-trasposición. Reivindicación 1: Un proceso para la preparación de un compuesto de la fórmula (1) en donde R es alquilo C₁₋₃; a partir de un compuesto de la fórmula (2) que comprende las siguientes etapas: a) crear una primera mezcla que contenga un alcóxido de metal álcali de la fórmula (3): MOR¹ (3) en donde M es Na o K, y R¹ es un alquilo C₁₋₃; y el compuesto de la fórmula (2) y calentar la primera mezcla; b) crear una segunda mezcla agregándole agua, un base fuerte, y metal de zinc a la primera mezcla; c) calentar la segunda mezcla; y d) aislar el compuesto de la fórmula (1). Reivindicación 6: Un proceso para la preparación de un compuesto de la fórmula (2) a partir de un compuesto de la fórmula (4) que comprende las siguientes etapas: a) crear una primera mezcla combinando juntos un sistema de agua-disolvente orgánico de 2 fases, una fuente de amoníaco, una fuente de cianuro y el compuesto de la fórmula (4); b) separar una segunda mezcla a partir de la primera mezcla que contiene un compuesto de la fórmula (5) en la forma de solución en el disolvente orgánico; c) agregar una solución acuosa de ácido mineral a la segunda mezcla para formar una tercera mezcla en donde el ácido mineral es HCl, HBr, H₂SO₄, HNO₃, H₃PO₄; d) separar una cuarta mezcla a partir de la tercera mezcla que es una mezcla acuosa que contiene un compuesto de la fórmula (6); en donde X es Cl, Br, HSO₄, NO₃ o H₂PO₄; e) agregar agente de bromación que incluye bromo, un compuesto de bromuro con un oxidante, y sus mezclas con la cuarta mezcla para formar una quinta mezcla; y f) aislar el compuesto de la fórmula (2) de la quinta mezcla. Reivindicación 12: Un proceso para la preparación de un compuesto de la fórmula (7) a partir de un compuesto de la fórmula (4) que comprende las siguientes etapas: a) crear una primera mezcla combinando juntos un sistema de agua-disolvente orgánico de 2 fases, una fuente de amoníaco, una fuente de cianuro y el compuesto de la fórmula (4); b) separar una segunda mezcla a partir de la primera mezcla que contiene el compuesto de la fórmula (5) en la forma de solución en el disolvente orgánico; c) agregar una solución acuosa de ácido mineral a la segunda mezcla para formar una tercera mezcla en donde el ácido mineral es HCl, HBr, H₂SO₄, HNO₃ o H₃PO₄; d) separar una cuarta mezcla a partir de la tercera mezcla que es una mezcla acuosa que contiene un compuesto de la fórmula (6); en donde X es Cl, Br, HSO₄, NO₃ o H₂PO₄; e) agregar un agente de bromación que incluye un compuesto de bromuro con un oxidante a la cuarta mezcla para formar una quinta mezcla; y f) aislar el compuesto de la fórmula (7) de la quinta mezcla.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662286008P | 2016-01-22 | 2016-01-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR107418A1 true AR107418A1 (es) | 2018-04-25 |
Family
ID=59362166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP170100174A AR107418A1 (es) | 2016-01-22 | 2017-01-24 | Proceso para la preparación de ácidos 4-alcoxi-3-hidroxipicolínicos |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US10550083B2 (es) |
| EP (1) | EP3405034B1 (es) |
| JP (1) | JP2019502732A (es) |
| CN (2) | CN114057633A (es) |
| AR (1) | AR107418A1 (es) |
| AU (1) | AU2017209458B2 (es) |
| BR (1) | BR112018014763B8 (es) |
| CA (1) | CA3011928A1 (es) |
| ES (1) | ES2883118T3 (es) |
| PL (1) | PL3405034T3 (es) |
| RU (1) | RU2744834C2 (es) |
| WO (1) | WO2017127794A1 (es) |
| ZA (1) | ZA201804877B (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2018130270A (ru) * | 2016-01-22 | 2020-02-25 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Способ получения 4-алкокси-3-ацетоксипиколиновых кислот |
| WO2024018354A1 (en) | 2022-07-18 | 2024-01-25 | Pi Industries Ltd. | A process for the synthesis of 4-alkoxy-3-hydroxypicolinic acids and intermediates thereof |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2772302A (en) | 1952-08-07 | 1956-11-27 | Perfogit Spa | Process for the production of 11-bromoundecanoic acid |
| FR2283089A1 (fr) | 1974-08-02 | 1976-03-26 | Ugine Kuhlmann | Procede de fabrication du brome |
| US3956338A (en) * | 1975-01-17 | 1976-05-11 | The Dow Chemical Company | 4,6-Dibromo-5-hydroxy-2-pyridine nitrile compounds and method of preparation |
| GB2095237B (en) | 1981-03-19 | 1985-04-03 | Ici Plc | Herbicidal and fungicidal substituted n-furyl or thienyl-methyl amides |
| US5266295A (en) | 1989-04-27 | 1993-11-30 | Akzo American Inc. | Hydrogen peroxide oxidation of bromide to bromide |
| WO2000049008A1 (en) * | 1999-02-20 | 2000-08-24 | Astrazeneca Ab | Di- and tripeptide nitrile derivatives as inhibitors of cathepsin l and cathepsin s |
| JP2003528806A (ja) | 1999-07-20 | 2003-09-30 | ダウ・アグロサイエンス・エル・エル・シー | 殺菌・殺カビ性複素環式芳香族アミドおよびそれらの組成物、使用および製造方法 |
| FR2803592A1 (fr) * | 2000-01-06 | 2001-07-13 | Aventis Cropscience Sa | Nouveaux derives de l'acide 3-hydroxypicolinique, leur procede de preparation et compositions fongicides les contenant. |
| WO2016007532A1 (en) * | 2014-07-08 | 2016-01-14 | Dow Agrosciences Llc | Process for the preparation of 3-hydroxypicolinic acids |
| JP6513178B2 (ja) * | 2014-07-08 | 2019-05-15 | ダウ アグロサイエンシィズ エルエルシー | ４−アルコキシ−３−ヒドロキシピコリン酸の製造方法 |
| RU2018130270A (ru) * | 2016-01-22 | 2020-02-25 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Способ получения 4-алкокси-3-ацетоксипиколиновых кислот |
| TW201733985A (zh) * | 2016-02-29 | 2017-10-01 | 陶氏農業科學公司 | 用於製備4-烷氧基-3-羥基吡啶甲酸之方法 |
-
2017
- 2017-01-23 AU AU2017209458A patent/AU2017209458B2/en active Active
- 2017-01-23 CA CA3011928A patent/CA3011928A1/en active Pending
- 2017-01-23 EP EP17742095.7A patent/EP3405034B1/en active Active
- 2017-01-23 PL PL17742095T patent/PL3405034T3/pl unknown
- 2017-01-23 CN CN202111230303.9A patent/CN114057633A/zh active Pending
- 2017-01-23 WO PCT/US2017/014532 patent/WO2017127794A1/en active Application Filing
- 2017-01-23 US US16/071,516 patent/US10550083B2/en active Active
- 2017-01-23 RU RU2018130160A patent/RU2744834C2/ru active
- 2017-01-23 ES ES17742095T patent/ES2883118T3/es active Active
- 2017-01-23 CN CN201780007857.8A patent/CN108495555A/zh active Pending
- 2017-01-23 JP JP2018538104A patent/JP2019502732A/ja active Pending
- 2017-01-23 BR BR112018014763A patent/BR112018014763B8/pt active IP Right Grant
- 2017-01-24 AR ARP170100174A patent/AR107418A1/es active IP Right Grant
-
2018
- 2018-07-19 ZA ZA2018/04877A patent/ZA201804877B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2883118T3 (es) | 2021-12-07 |
| CA3011928A1 (en) | 2017-07-27 |
| US20190112271A1 (en) | 2019-04-18 |
| WO2017127794A1 (en) | 2017-07-27 |
| EP3405034B1 (en) | 2021-05-12 |
| BR112018014763A2 (pt) | 2018-12-11 |
| RU2744834C2 (ru) | 2021-03-16 |
| AU2017209458B2 (en) | 2020-09-10 |
| AU2017209458A1 (en) | 2018-08-02 |
| US10550083B2 (en) | 2020-02-04 |
| CN108495555A (zh) | 2018-09-04 |
| EP3405034A4 (en) | 2019-10-23 |
| JP2019502732A (ja) | 2019-01-31 |
| RU2018130160A3 (es) | 2020-09-24 |
| CN114057633A (zh) | 2022-02-18 |
| EP3405034A1 (en) | 2018-11-28 |
| PL3405034T3 (pl) | 2021-11-22 |
| RU2018130160A (ru) | 2020-02-25 |
| BR112018014763B8 (pt) | 2023-05-16 |
| BR112018014763B1 (pt) | 2022-07-19 |
| ZA201804877B (en) | 2019-09-25 |
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