AR097971A1 - Formas cristalinas de derivado de diazabiciclooctano y proceso de producción de ellas - Google Patents
Formas cristalinas de derivado de diazabiciclooctano y proceso de producción de ellasInfo
- Publication number
- AR097971A1 AR097971A1 ARP140103759A ARP140103759A AR097971A1 AR 097971 A1 AR097971 A1 AR 097971A1 AR P140103759 A ARP140103759 A AR P140103759A AR P140103759 A ARP140103759 A AR P140103759A AR 097971 A1 AR097971 A1 AR 097971A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound represented
- appear
- diffraction pattern
- powder diffraction
- Prior art date
Links
- 239000013078 crystal Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 12
- -1 sulfur trioxylamine Chemical compound 0.000 abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 238000000634 powder X-ray diffraction Methods 0.000 abstract 3
- 125000006239 protecting group Chemical group 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003463 adsorbent Substances 0.000 abstract 1
- 239000003125 aqueous solvent Substances 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000012043 crude product Substances 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 238000011033 desalting Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000010899 nucleation Methods 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Reivindicación 1: Un proceso para producir un compuesto representado por la fórmula (4), caracterizado porque comprende: hacer reaccionar un compuesto representado por la fórmula (1) con un compuesto: R³ONH₂ para obtener un compuesto representado por la fórmula (2) tratar con un catalizador de paladio sobre carbón bajo una atmósfera de hidrógeno, someter simultánea o consecutivamente a una reacción de sulfatación usando complejo de trióxido de azufre-trimetilamina en presencia de una cantidad catalítica de base en un solvente acuoso y tratar con hidrógeno-sulfato de tetrabutilamonio para obtener un compuesto representado por la fórmula (3) seguido, en un caso en que la cadena lateral de R³ONHC(=O)- tenga un grupo protector, eliminación del grupo protector con un ácido y precipitación de un producto crudo por adición de un solvente pobre a la solución de reacción para obtener un compuesto crudo representado por la fórmula (4-CR) seguido alternativamente por adición del compuesto crudo representado por la fórmula (4-CR) y tampón helado para obtener una solución que tiene un pH de 4 a 5,5, concentración después de desalar con un adsorbente sintético de ser necesario, ajuste de la temperatura, siembra de ser necesario y cristalización por adición de un solvente pobre para producir el compuesto representado por la fórmula (4) (en cada una de las fórmulas anteriores, OBn es benciloxi; R¹ es 2,5-dioxopirrolidin-1-ilo, 1,3-dioxo-3a,4,7,7a-tetrahidro-1H-isoindol-2(3H)-ilo, 1,3-dioxohexahidro-1H-isoindol-2(3H)-ilo o 3,5-dioxo-4-azatriciclo[5,2,1,02,6]dec-8-en-4-ilo; R³ es alquilo C₁₋₆ o heterociclilo, R³ se puede modificar con 0 a 5 R⁴; R⁴ se pueden sustituir consecutivamente; aquí, R⁴ es alquilo C₁₋₆, heterociclilo, R⁵(R⁶)N- o un grupo protector; R⁵ y R⁶ son cada uno, de modo independiente, hidrógeno o alquilo C₁₋₆ o forman juntos heterociclilo; por otra parte, R³, R⁵ y R⁶ se pueden someter a cierre del anillo en una posición arbitraria. Reivindicación 12: Una forma cristalina I de un compuesto representado por la fórmula (5) caracterizado porque tiene picos característicos que aparecen en el espaciado reticular (d) de 7,34, 5,66, 5,53, 5,30, 5,02, 4,66, 4,37, 4,28, 4,06, 3,68, 3,62, 3,47, 3,36, 3,30, 3,16, 3,11, 3,03, 2,99 y 2,50 Å en el patrón de difracción de polvos por rayos X. Reivindicación 17: Una forma cristalina II de un compuesto representado por la fórmula (5) caracterizado porque tiene picos característicos que aparecen en el espaciado reticular (d) de 9,46, 5,62, 5,23, 5,10, 5,00, 4,91, 4,67, 4,45, 4,29, 3,96, 3,78, 3,71, 3,52, 3,24, 3,18, 3,10, 3,02, 2,88, 2,81, 2,77, 2,67, 2,50 y 2,45 Å en el patrón de difracción de polvos por rayos X. Reivindicación 22: Una forma cristalina III de un compuesto representado por la fórmula (5) caracterizado porque tiene picos característicos que aparecen en el espaciado reticular (d) de 8,32, 6,10, 5,98, 5,51, 5,16, 5,07, 4,85, 4,70, 4,61, 4,35, 4,20, 4,06, 4,00, 3,95, 3,77, 3,73, 3,65, 3,42, 3,39, 3,36, 3,26, 3,23, 3,13, 3,09, 2,99, 2,81 y 2,52 Å en el patrón de difracción de polvos por rayos X. Reivindicación 27: Una forma cristalina IV de un compuesto representado por la fórmula (5) caracterizado porque tiene picos característicos que aparecen en el espaciado reticular (d) de 7,88, 6,41, 5,20, 4,67, 4,50, 4,02, 3,81, 3,75, 3,70, 3,62, 3,38, 3,23, 3,20 y 2,74 Å en el patrón de difracción de polvos por rayos X.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013211242 | 2013-10-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
AR097971A1 true AR097971A1 (es) | 2016-04-20 |
Family
ID=52813113
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP140103759A AR097971A1 (es) | 2013-10-08 | 2014-10-08 | Formas cristalinas de derivado de diazabiciclooctano y proceso de producción de ellas |
Country Status (21)
Country | Link |
---|---|
US (4) | US10131665B2 (es) |
EP (4) | EP3613740A1 (es) |
JP (3) | JP6617029B2 (es) |
KR (2) | KR102487297B1 (es) |
CN (2) | CN111153903A (es) |
AR (1) | AR097971A1 (es) |
AU (1) | AU2014332960B2 (es) |
BR (2) | BR112016006266B1 (es) |
CA (2) | CA2926071C (es) |
DK (1) | DK3067355T3 (es) |
ES (2) | ES2901198T3 (es) |
HK (2) | HK1219479A1 (es) |
HU (1) | HUE051925T2 (es) |
IL (2) | IL244969B (es) |
MX (1) | MX361659B (es) |
NZ (5) | NZ757222A (es) |
RU (1) | RU2695219C2 (es) |
SG (1) | SG11201602723RA (es) |
TW (1) | TWI673269B (es) |
WO (1) | WO2015053297A1 (es) |
ZA (1) | ZA201602054B (es) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PL2857401T3 (pl) | 2012-05-30 | 2020-02-28 | Meiji Seika Pharma Co., Ltd. | NOWY INHIBITOR ß–LAKTAMAZY I SPOSÓB JEGO WYTWARZANIA |
JP6453222B2 (ja) * | 2013-09-24 | 2019-01-16 | Meiji Seikaファルマ株式会社 | ジアザビシクロオクタン誘導体の製造法とその中間体 |
HUE051925T2 (hu) | 2013-10-08 | 2021-04-28 | Meiji Seika Pharma Co Ltd | Dizabiciklooktán származék kristályai és diazabiciklooktán származék kristályainak elõállítási eljárása |
ES2821826T3 (es) * | 2014-12-05 | 2021-04-27 | Meiji Seika Pharma Co Ltd | Método para producir cristales de derivado de diazabiciclooctano y preparación liofilizada estable |
US10208041B2 (en) * | 2016-10-07 | 2019-02-19 | Hoffman-La Roche Inc. | Diazabicyclooctane compounds |
KR20200030584A (ko) | 2017-07-21 | 2020-03-20 | 앤타바이오 에스에이에스 | 화합물 |
EP3687993A1 (en) * | 2017-09-27 | 2020-08-05 | Meiji Seika Pharma Co., Ltd. | Pharmaceutical forms of diazabicyclooctane derivatives and manufacturing method thereof |
CN111448195A (zh) * | 2017-09-27 | 2020-07-24 | 费多拉制药公司 | 二氮杂二环辛烷衍生物的晶型及其生产方法 |
WO2019064065A1 (en) | 2017-09-27 | 2019-04-04 | F. Hoffmann-La Roche Ag | PHARMACEUTICAL FORMS OF DIAZABICYCLOOCTANE DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF |
CN107941944B (zh) * | 2017-11-23 | 2020-09-15 | 中山奕安泰医药科技有限公司 | 一种(2s,5r)-苄氧胺基哌啶-2-甲酸乙酯草酸盐的检测方法 |
CN107991404B (zh) * | 2017-11-23 | 2021-01-08 | 中山奕安泰医药科技有限公司 | 一种(2s,5r)-苄氧胺基哌啶-2-甲酰胺的检测方法 |
EP3572411A1 (en) | 2018-05-21 | 2019-11-27 | Antabio SAS | Thiazole derivatives as metallo-beta-lactamase inhibitors |
CN112930338A (zh) * | 2018-09-21 | 2021-06-08 | 株式会社Api | 氨基酸衍生物的制备方法 |
WO2022014397A1 (ja) * | 2020-07-13 | 2022-01-20 | 日本碍子株式会社 | 精製方法 |
CN113552250A (zh) * | 2021-06-30 | 2021-10-26 | 海南海灵化学制药有限公司 | 一种盐酸头孢唑兰的杂质检测方法 |
Family Cites Families (33)
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JPH07117533B2 (ja) | 1985-08-28 | 1995-12-18 | 株式会社生体科学研究所 | トランスフエリンおよびその用途 |
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FR2812635B1 (fr) | 2000-08-01 | 2002-10-11 | Aventis Pharma Sa | Nouveaux composes heterocycliques, preparation et utilisation comme medicaments notamment comme anti- bacteriens |
FR2825705B1 (fr) | 2001-06-08 | 2005-05-20 | Aventis Pharma Sa | Nouveaux composes heterocycliques, leur preparation et leur utilisation comme medicaments, notamment comme anti-bacteriens |
FR2835186B1 (fr) | 2002-01-28 | 2006-10-20 | Aventis Pharma Sa | Nouveaux composes heterocycliques, actifs comme inhibiteurs de beta-lactamases |
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ES2533826T3 (es) | 2008-01-18 | 2015-04-15 | Merck Sharp & Dohme Corp. | Inhibidores de beta-lactamasa |
FR2930553B1 (fr) | 2008-04-29 | 2010-05-21 | Novexel | Composes azabicycliques, leur preparation et leur utilisation comme medicaments, notamment inhibiteurs de beta-lactamases |
FR2936798B1 (fr) | 2008-10-03 | 2012-09-28 | Novexel | Nouveaux composes heterocycliques azotes, leur preparation et leur utilisation comme medicaments antibacteriens. |
US20120053350A1 (en) | 2009-04-30 | 2012-03-01 | Ian Mangion | Preparation of alkyl esters of n-protected oxo-azacycloalkylcarboxylic acids |
FR2951171A1 (fr) | 2009-10-09 | 2011-04-15 | Novexel | Nouveau sel de sodium d'un compose azabicyclique sous forme enantiomere cristallisee et nouvelles formes polymorphes et pseudopolymorphes ainsi que leur preparation |
JP2012122603A (ja) * | 2010-11-15 | 2012-06-28 | Nifco Inc | コネクタ装置 |
CA2822758C (en) | 2010-12-22 | 2018-03-20 | Meiji Seika Pharma Co., Ltd. | Optically active diazabicyclooctane derivative and process for preparing the same |
US8772490B2 (en) | 2010-12-22 | 2014-07-08 | Meiji Seika Pharma Co., Ltd. | Optically active diazabicyclooctane derivatives and process for preparing the same |
BR112013032415B1 (pt) * | 2011-06-17 | 2021-07-27 | Pfizer Anti-Infectives Ab | Processos para preparar compostos e compostos |
AU2012303691B2 (en) | 2011-08-27 | 2014-06-19 | Wockhardt Limited | 1,6- diazabicyclo [3,2,1] octan-7-one derivatives and their use in the treatment of bacterial infections |
AU2012303693B2 (en) | 2011-08-30 | 2014-07-03 | Wockhardt Limited | 1,6- diazabicyclo [3,2,1] octan- 7 - one derivatives and their use in the treatment of bacterial infections |
BR112014003476A2 (pt) | 2011-09-13 | 2017-03-01 | Wockhardt Ltd | compostos contendo nitrogênio e seu uso |
US9505761B2 (en) | 2011-12-02 | 2016-11-29 | Fedora Pharmaceuticals Inc. | Bicyclic compounds and their use as antibacterial agents and beta-lactamase inhibitors |
US8796257B2 (en) | 2011-12-02 | 2014-08-05 | Naeja Pharmaceutical Inc. | Bicyclic compounds and their use as antibacterial agents and β-lactamase inhibitors |
PL2857401T3 (pl) | 2012-05-30 | 2020-02-28 | Meiji Seika Pharma Co., Ltd. | NOWY INHIBITOR ß–LAKTAMAZY I SPOSÓB JEGO WYTWARZANIA |
AU2013308127B2 (en) * | 2012-08-25 | 2015-08-13 | Wockhardt Limited | 1,6- Diazabicyclo [3,2,1] octan- 7- one derivatives and their use in the treatment of bacterial infections |
JP6453222B2 (ja) * | 2013-09-24 | 2019-01-16 | Meiji Seikaファルマ株式会社 | ジアザビシクロオクタン誘導体の製造法とその中間体 |
HUE051925T2 (hu) | 2013-10-08 | 2021-04-28 | Meiji Seika Pharma Co Ltd | Dizabiciklooktán származék kristályai és diazabiciklooktán származék kristályainak elõállítási eljárása |
ES2821826T3 (es) | 2014-12-05 | 2021-04-27 | Meiji Seika Pharma Co Ltd | Método para producir cristales de derivado de diazabiciclooctano y preparación liofilizada estable |
-
2014
- 2014-10-08 HU HUE14852849A patent/HUE051925T2/hu unknown
- 2014-10-08 RU RU2016116501A patent/RU2695219C2/ru active
- 2014-10-08 US US15/027,956 patent/US10131665B2/en active Active
- 2014-10-08 BR BR112016006266-3A patent/BR112016006266B1/pt active IP Right Grant
- 2014-10-08 NZ NZ757222A patent/NZ757222A/en unknown
- 2014-10-08 AR ARP140103759A patent/AR097971A1/es not_active Application Discontinuation
- 2014-10-08 EP EP19202412.3A patent/EP3613740A1/en not_active Withdrawn
- 2014-10-08 CA CA2926071A patent/CA2926071C/en active Active
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