MX380203B - Procedimiento para la preparación de iopamidol. - Google Patents
Procedimiento para la preparación de iopamidol.Info
- Publication number
- MX380203B MX380203B MX2020010367A MX2020010367A MX380203B MX 380203 B MX380203 B MX 380203B MX 2020010367 A MX2020010367 A MX 2020010367A MX 2020010367 A MX2020010367 A MX 2020010367A MX 380203 B MX380203 B MX 380203B
- Authority
- MX
- Mexico
- Prior art keywords
- group
- butyl
- acetyloxy
- boron
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- XQZXYNRDCRIARQ-LURJTMIESA-N iopamidol Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(=O)NC(CO)CO)=C(I)C(C(=O)NC(CO)CO)=C1I XQZXYNRDCRIARQ-LURJTMIESA-N 0.000 title abstract 2
- 229960004647 iopamidol Drugs 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 2
- 229910052796 boron Inorganic materials 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- -1 (S)-2-(hydroxy)propanoyl group Chemical group 0.000 abstract 1
- ALHZEIINTQJLOT-VKHMYHEASA-N [(2s)-1-chloro-1-oxopropan-2-yl] acetate Chemical compound ClC(=O)[C@H](C)OC(C)=O ALHZEIINTQJLOT-VKHMYHEASA-N 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001638 boron Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 238000011084 recovery Methods 0.000 abstract 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and at least three atoms of bromine or iodine, bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/05—Cyclic compounds having at least one ring containing boron but no carbon in the ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Detergent Compositions (AREA)
Abstract
La presente invención da a conocer un proceso para la preparación de Iopamidol de fórmula II (ver Fórmulas) y que comprende los siguientes pasos: a) hacer reaccionar el Compuesto (I) en donde X es OR2 o R3, y en donde R2 y R3 son un alquilo lineal o ramificado C1-C6, un cicloalquilo C3-C6, un arilo C6, opcionalmente sustituido con un grupo seleccionado del grupo que consiste en metilo, etilo, n-propilo, i-propilo, n-butilo, sec-butilo, t-butilo y fenilo, con el agente acilante cloruro de (S)-2-(acetiloxi)propanoilo en un medio reacción para generar el derivado acetiloxilado del Compuesto (I); b) hidrolizar el intermediario del paso a) con una disolución acuosa a un pH comprendido entre 0 y 7, mediante la adición de agua o una disolución alcalina diluida, tal como hidróxido de sodio o hidróxido de potasio, la liberación de los hidroxilos de los grupos protectores que contienen boro, la obtención de del derivado N-(S)-2- (acetiloxi)propanoilo derivado del Compuesto (II); c) hidrólisis alcalina para restaurar el grupo (S)-2- (hidroxi)propanoílo y para obtener Iopamidol (II) y la recuperación opcional del derivado de boro de la disolución obtenida en el paso b). El grupo protector que contiene boro es versátil, eficaz y reciclable. Se proporciona una síntesis tipo "one pot" sin aislamiento del intermediario, lo que lleva a una disminución de disolventes recuperados y reciclados y a un aumento significativo del rendimiento, lo que representa una ventaja significativa en términos de costo-eficacia de todo el proceso y de conciencia ambiental.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13191551 | 2013-11-05 | ||
| PCT/EP2014/073692 WO2015067601A1 (en) | 2013-11-05 | 2014-11-04 | Process for the preparation of iopamidol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MX2020010367A MX2020010367A (es) | 2021-03-03 |
| MX380203B true MX380203B (es) | 2025-03-12 |
Family
ID=49517391
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2020010367A MX380203B (es) | 2013-11-05 | 2014-11-04 | Procedimiento para la preparación de iopamidol. |
| MX2016005829A MX375753B (es) | 2013-11-05 | 2014-11-04 | Procedimiento para la preparacion de iopamidol. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2016005829A MX375753B (es) | 2013-11-05 | 2014-11-04 | Procedimiento para la preparacion de iopamidol. |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US9950991B2 (es) |
| EP (2) | EP3066071B1 (es) |
| JP (1) | JP6454351B2 (es) |
| KR (2) | KR102265049B1 (es) |
| CN (1) | CN105705483B (es) |
| AU (1) | AU2014345727B2 (es) |
| BR (1) | BR112016010223B1 (es) |
| CA (2) | CA2927706C (es) |
| DK (2) | DK3066071T3 (es) |
| ES (2) | ES2862349T3 (es) |
| HR (2) | HRP20181122T1 (es) |
| HU (2) | HUE039440T2 (es) |
| IL (1) | IL245457B (es) |
| LT (2) | LT3369724T (es) |
| MX (2) | MX380203B (es) |
| PL (2) | PL3066071T3 (es) |
| PT (2) | PT3369724T (es) |
| RU (1) | RU2657238C2 (es) |
| SI (2) | SI3066071T1 (es) |
| TR (1) | TR201808527T4 (es) |
| WO (1) | WO2015067601A1 (es) |
| ZA (1) | ZA201602970B (es) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106366015B (zh) * | 2015-07-22 | 2019-01-25 | 正大天晴药业集团股份有限公司 | 一种碘普罗胺的制备方法及其中间体 |
| CN106366016B (zh) * | 2015-07-22 | 2019-03-05 | 连云港润众制药有限公司 | 一种碘普罗胺的制备方法及其中间体 |
| SG11202003762VA (en) | 2017-11-01 | 2020-05-28 | Melinta Therapeutics Inc | Synthesis of boronate ester derivatives and uses thereof |
| CN109293526A (zh) * | 2018-10-23 | 2019-02-01 | 湖北天舒药业有限公司 | 一种碘帕醇的合成及其合成中间体的制备 |
| MX2022009932A (es) * | 2020-02-14 | 2022-11-07 | Solvay | Nuevos espumantes para la recuperacion de minerales y metodos de fabricacion y uso de los mismos. |
| GB202009917D0 (en) * | 2020-06-29 | 2020-08-12 | Ge Healthcare As | Process for the preparation of iopamidol |
| EP4313934B1 (en) * | 2021-03-22 | 2025-05-07 | Bracco Imaging SPA | Industrial synthesis of serinol |
| JP2024545278A (ja) | 2021-12-20 | 2024-12-05 | ブラッコ・イメージング・ソシエタ・ペル・アチオニ | ２，４，６－トリヨードイソフタル酸ビスアミドの製造方法 |
| CN115010617B (zh) * | 2022-07-11 | 2024-06-11 | 安徽普利药业有限公司 | 一种碘帕醇的制备方法 |
| EP4534526A1 (en) | 2023-10-04 | 2025-04-09 | Bracco Imaging SPA | Optimized process for the preparation of iopamidol |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH608189A5 (es) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
| IT1256162B (it) | 1992-10-27 | 1995-11-29 | Zambon Spa | Processo per la preparazione di un intermedio della sintesi organica |
| IT1274027B (it) | 1994-03-03 | 1997-07-14 | Zambon Spa | Processo per la preparazione e purificazione di mezzi di contrasto iodurati |
| IT1274676B (it) * | 1994-04-14 | 1997-07-24 | Zambon Spa | Processo per la preparazione di 5-ammino-2,2-dialchil-1,3-diossani |
| IT1282674B1 (it) | 1996-02-23 | 1998-03-31 | Bracco Spa | Processo per la purificazione di agenti contrastografici opacizzanti |
| CA2195634C (en) | 1995-05-23 | 2008-11-18 | Marina Mauro | Process for the preparation of a dicarboxylic acid dichloride |
| BR9606488A (pt) | 1995-05-23 | 1997-11-25 | Fructamine Spa | Processo para a preparação de um dicloreto de ácido dicarboxílico |
| US5763650A (en) | 1995-05-23 | 1998-06-09 | Fructamine S.P.A. | Process for the preparation of a halosubstituted aromatic acid |
| IT1288114B1 (it) | 1996-06-13 | 1998-09-10 | Fructamine Spa | Processo per la purificazione di un intermedio |
| IT1286522B1 (it) | 1996-12-04 | 1998-07-15 | Dibra Spa | Processo per la preparazione di derivati dell'acido 5-ammino-2,4,6- triiodo-1,3-benzenedicarbossilico |
| IT1289520B1 (it) | 1996-12-24 | 1998-10-15 | Zambon Spa | Processo per la preparazione di un intermedio utile nella sintesi di mezzi di contrasto iodurati |
| GB2331098A (en) | 1997-11-07 | 1999-05-12 | Nycomed Imaging As | An N-Alkylation process |
| IT1299202B1 (it) | 1998-05-08 | 2000-02-29 | Dibra Spa | Processo per la preparazione della s-n,n'-bis (2-idrossi-1- (idrossimetil)etil) -5-((2-idrossi-1-ossopropil)ammino)-2,4,6-triiodo |
| GB9825095D0 (en) | 1998-11-16 | 1999-01-13 | Nycomed Imaging As | Chemical process |
| US6803485B2 (en) * | 1999-02-26 | 2004-10-12 | Bracco Imaging S.P.A. | Process for the preparation of iopamidol |
| IT1319671B1 (it) | 2000-12-01 | 2003-10-23 | Bracco Spa | Processo per la preparazione di (s)-n,n'-bis(2-idrossi-1-(idrossimetil)etil)-5-((2-idrossi-1-ossopropil)ammino) |
| IT1319670B1 (it) * | 2000-12-01 | 2003-10-23 | Bracco Spa | Processo per la preparazione di 5-ammino-n,n'-bis(2-idrossi-1-(idrossimetil)etil))-1,3-benzendicarbossammide (i) e 5-ammino-n,n'- |
| WO2005019229A1 (en) * | 2003-08-26 | 2005-03-03 | Biocon Limited | Process for purification of boronic acid and its derivatives |
| ES2380549T3 (es) | 2005-10-21 | 2012-05-16 | Video Taped Transcripts Pty. Ltd. | Un método para producir una guarnición retrorreflectante perforada |
| EP2093206A1 (en) | 2008-02-20 | 2009-08-26 | BRACCO IMAGING S.p.A. | Process for the iodination of aromatic compounds |
| DK2365963T3 (en) | 2008-11-18 | 2017-10-09 | Bracco Imaging Spa | PROCEDURE FOR THE PREPARATION OF IODATED CONTRACTOR |
| EP2243767A1 (en) | 2009-04-21 | 2010-10-27 | Bracco Imaging S.p.A | Process for the iodination of aromatic compounds |
| EP2451994B1 (en) | 2009-07-07 | 2013-10-23 | Bracco Imaging SPA | Process for the preparation of a iodinating agent |
| EP2394984A1 (en) | 2010-06-10 | 2011-12-14 | Bracco Imaging S.p.A | Process for the iodination of phenolic derivatives |
-
2014
- 2014-11-04 BR BR112016010223-1A patent/BR112016010223B1/pt active IP Right Grant
- 2014-11-04 DK DK14796024.9T patent/DK3066071T3/en active
- 2014-11-04 PT PT181624826T patent/PT3369724T/pt unknown
- 2014-11-04 EP EP14796024.9A patent/EP3066071B1/en active Active
- 2014-11-04 EP EP18162482.6A patent/EP3369724B1/en active Active
- 2014-11-04 CA CA2927706A patent/CA2927706C/en active Active
- 2014-11-04 LT LTEP18162482.6T patent/LT3369724T/lt unknown
- 2014-11-04 KR KR1020167014721A patent/KR102265049B1/ko active Active
- 2014-11-04 PT PT147960249T patent/PT3066071T/pt unknown
- 2014-11-04 CA CA3001399A patent/CA3001399C/en active Active
- 2014-11-04 HU HUE14796024A patent/HUE039440T2/hu unknown
- 2014-11-04 LT LTEP14796024.9T patent/LT3066071T/lt unknown
- 2014-11-04 DK DK18162482.6T patent/DK3369724T3/da active
- 2014-11-04 AU AU2014345727A patent/AU2014345727B2/en active Active
- 2014-11-04 PL PL14796024T patent/PL3066071T3/pl unknown
- 2014-11-04 SI SI201430793T patent/SI3066071T1/en unknown
- 2014-11-04 JP JP2016551022A patent/JP6454351B2/ja active Active
- 2014-11-04 HU HUE18162482A patent/HUE053751T2/hu unknown
- 2014-11-04 TR TR2018/08527T patent/TR201808527T4/tr unknown
- 2014-11-04 US US15/033,737 patent/US9950991B2/en active Active
- 2014-11-04 SI SI201431776T patent/SI3369724T1/sl unknown
- 2014-11-04 PL PL18162482T patent/PL3369724T3/pl unknown
- 2014-11-04 MX MX2020010367A patent/MX380203B/es unknown
- 2014-11-04 KR KR1020217017633A patent/KR102382351B1/ko active Active
- 2014-11-04 ES ES18162482T patent/ES2862349T3/es active Active
- 2014-11-04 ES ES14796024.9T patent/ES2674279T3/es active Active
- 2014-11-04 WO PCT/EP2014/073692 patent/WO2015067601A1/en not_active Ceased
- 2014-11-04 RU RU2016122022A patent/RU2657238C2/ru active
- 2014-11-04 HR HRP20181122TT patent/HRP20181122T1/hr unknown
- 2014-11-04 MX MX2016005829A patent/MX375753B/es active IP Right Grant
- 2014-11-04 CN CN201480060539.4A patent/CN105705483B/zh active Active
-
2016
- 2016-05-03 IL IL245457A patent/IL245457B/en active IP Right Grant
- 2016-05-04 ZA ZA2016/02970A patent/ZA201602970B/en unknown
-
2018
- 2018-03-06 US US15/912,772 patent/US10377700B2/en active Active
- 2018-08-02 US US16/052,695 patent/US20190077745A1/en not_active Abandoned
-
2021
- 2021-02-25 HR HRP20210324TT patent/HRP20210324T1/hr unknown
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