MA33489B1 - Procédé de synthèse amélioré de la pirfénidone - Google Patents
Procédé de synthèse amélioré de la pirfénidoneInfo
- Publication number
- MA33489B1 MA33489B1 MA34508A MA34508A MA33489B1 MA 33489 B1 MA33489 B1 MA 33489B1 MA 34508 A MA34508 A MA 34508A MA 34508 A MA34508 A MA 34508A MA 33489 B1 MA33489 B1 MA 33489B1
- Authority
- MA
- Morocco
- Prior art keywords
- pirfenidone
- synthesis
- improved process
- synthesizing
- butanol
- Prior art date
Links
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 title abstract 5
- 229960003073 pirfenidone Drugs 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 4
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 4
- 230000002194 synthesizing effect Effects 0.000 abstract 3
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 abstract 2
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 230000014759 maintenance of location Effects 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- 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
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Gastroenterology & Hepatology (AREA)
- Pulmonology (AREA)
- Agronomy & Crop Science (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Cardiology (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Cette invention concerne un procédé de synthèse de pirfénidone à partir d'un bromobenzène contenant moins de 0,15 % en poids environ de dibromobenzène. Des procédés de synthèse de pirfénidone sans utiliser d'acétate d'éthyle ou de n-butanol, et des procédés de synthèse de pirfénidone ayant des teneurs contrôlées d'acétate d'éthyle, de n-butanol, de di-(5-méthyl-2- pyridinone)benzènes, et autres impuretés ayant des temps de rétention spécifiés sont également décrits. Cette invention concerne également des formes pharmaceutiques formulées contenant la pirfénidone décrite.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18358809P | 2009-06-03 | 2009-06-03 | |
| PCT/US2010/037090 WO2010141600A2 (fr) | 2009-06-03 | 2010-06-02 | Procédé de synthèse amélioré de la pirfénidone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MA33489B1 true MA33489B1 (fr) | 2012-08-01 |
Family
ID=43298478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MA34508A MA33489B1 (fr) | 2009-06-03 | 2010-06-02 | Procédé de synthèse amélioré de la pirfénidone |
Country Status (35)
| Country | Link |
|---|---|
| US (6) | US20110003863A1 (fr) |
| EP (1) | EP2440543B1 (fr) |
| JP (2) | JP5848244B2 (fr) |
| KR (1) | KR101734858B1 (fr) |
| CN (1) | CN102482255A (fr) |
| AP (1) | AP3630A (fr) |
| AR (1) | AR076974A1 (fr) |
| AU (1) | AU2010256693B2 (fr) |
| BR (1) | BRPI1011015B8 (fr) |
| CA (1) | CA2764043C (fr) |
| CL (1) | CL2011003069A1 (fr) |
| DK (1) | DK2440543T3 (fr) |
| EA (1) | EA021826B1 (fr) |
| ES (1) | ES2538103T3 (fr) |
| GE (1) | GEP20156223B (fr) |
| HN (1) | HN2011003187A (fr) |
| HR (1) | HRP20150696T1 (fr) |
| HU (1) | HUE026014T2 (fr) |
| IL (1) | IL216565A (fr) |
| MA (1) | MA33489B1 (fr) |
| MX (1) | MX2011012654A (fr) |
| MY (1) | MY162443A (fr) |
| NI (1) | NI201100211A (fr) |
| NZ (1) | NZ596872A (fr) |
| PE (1) | PE20120398A1 (fr) |
| PL (1) | PL2440543T3 (fr) |
| PT (1) | PT2440543E (fr) |
| RS (1) | RS54031B1 (fr) |
| SG (1) | SG176648A1 (fr) |
| SI (1) | SI2440543T1 (fr) |
| TN (1) | TN2011000615A1 (fr) |
| TW (1) | TWI434833B (fr) |
| UA (1) | UA106759C2 (fr) |
| WO (1) | WO2010141600A2 (fr) |
| ZA (1) | ZA201108794B (fr) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102099036B (zh) | 2008-06-03 | 2015-05-27 | 英特芒尼公司 | 用于治疗炎性疾患和纤维化疾患的化合物和方法 |
| WO2012106382A1 (fr) | 2011-01-31 | 2012-08-09 | Genoa Pharmaceuticals, Inc. | Composés analogues de pyridone et de pirfénidone en aérosol, et leurs utilisations |
| US10105356B2 (en) | 2011-01-31 | 2018-10-23 | Avalyn Pharma Inc. | Aerosol pirfenidone and pyridone analog compounds and uses thereof |
| MX2011007675A (es) | 2011-07-19 | 2012-07-11 | Cell Therapy And Technology S A De C V | Procedimiento para la fabricacion de una composicion farmaceutica en forma de tabletas de liberacion prolongada conteniendo pirfenidona y su aplicacion en la regresion de la insuficiencia renal cronica, contractura capsular mamaria y fibrosis hepatica humanas. |
| MX356551B (es) | 2012-08-23 | 2018-06-04 | Grupo Medifarma S A De C V Star | Composición antiséptica, antiseborreica y exfoliante para eliminar o prevenir el acné. |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| AU2015204558B2 (en) | 2014-01-10 | 2020-04-30 | Avalyn Pharma Inc. | Aerosol pirfenidone and pyridone analog compounds and uses thereof |
| MX382781B (es) | 2014-04-02 | 2025-03-13 | Intermune Inc | Piridinonas anti-fibroticas. |
| CA2958195A1 (fr) * | 2014-08-15 | 2016-02-18 | PixarBio Corporation | Compositions pour inhiber une inflammation chez un sujet presentant une lesion de la moelle epiniere, et procedes d'utilisation de ces compositions |
| EP3307714A1 (fr) * | 2015-01-26 | 2018-04-18 | Ulkar Kimya Sanayii Ve Ticaret A. S. | Procédé amélioré de synthèse et de purification de pirfénidone |
| ITUB20154832A1 (it) * | 2015-10-29 | 2017-04-29 | Procos Spa | Processo per la sintesi di pirfenidone |
| CN105315198A (zh) * | 2015-11-02 | 2016-02-10 | 重庆康乐制药有限公司 | 一种吡非尼酮的晶型及其制备方法 |
| CN105330598B (zh) * | 2015-12-02 | 2017-11-14 | 新发药业有限公司 | 一种吡非尼酮的制备方法 |
| WO2017122139A1 (fr) * | 2016-01-14 | 2017-07-20 | Laurus Labs Limited | Procédé perfectionné de préparation de pirfénidone |
| US11066368B2 (en) | 2016-01-14 | 2021-07-20 | Laurus Labs Limited | Process for the preparation and particle size reduction of pirfenidone |
| WO2017130166A1 (fr) * | 2016-01-31 | 2017-08-03 | Granules India Limited | Procédé amélioré pour la préparation de médicament anti-fibrotique de haute pureté |
| CA2937365C (fr) | 2016-03-29 | 2018-09-18 | F. Hoffmann-La Roche Ag | Formulation en granules de 5-methyl-1-phenyl-2-(1h)-pyridone et methode de fabrication associee |
| IT201600071672A1 (it) * | 2016-07-08 | 2018-01-08 | Dipharma Francis Srl | Metodo per sintetizzare un farmaco immunosoppressore |
| IT201600108927A1 (it) * | 2016-10-27 | 2018-04-27 | Dipharma Francis Srl | Metodo per sintetizzare un farmaco antifibrotico |
| US20180009753A1 (en) * | 2016-07-08 | 2018-01-11 | Dipharma Francis S.R.L. | Method for preparing an antifibrotic agent |
| WO2018083709A1 (fr) * | 2016-11-07 | 2018-05-11 | Msn Laboratories Private Limited, R&D Center | Procédé amélioré pour la préparation de 5-méthyl-1-phényl-2-1 (h)-pyridone pure |
| WO2018178996A1 (fr) * | 2017-03-28 | 2018-10-04 | Natco Pharma Limited | Procédé amélioré pour la préparation de pirfénidone |
| US12365651B2 (en) | 2017-07-31 | 2025-07-22 | Washington University | Use of pirfenidone and derivatives for modulation of B lymphocyte activity and organ protection from acute tissue damage |
| ES2886152T3 (es) | 2017-12-11 | 2021-12-16 | Laurus Labs Ltd | Un procedimiento mejorado para la preparación de pirfenidona |
| CN112409246B (zh) * | 2019-08-21 | 2023-04-07 | 北京凯因科技股份有限公司 | 一种吡非尼酮的晶型及其制备方法 |
| CN115666533B (zh) * | 2020-04-22 | 2024-08-09 | 永进药品工业株式会社 | 具有改善的安全性和稳定性的含吡非尼酮的肠溶包衣制剂及其制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3839346A (en) * | 1972-12-18 | 1974-10-01 | Affiliated Med Res | N-substituted pyridone and general method for preparing pyridones |
| US5356898A (en) * | 1991-01-31 | 1994-10-18 | Warner-Lambert Company | Substituted 4,6-di-tertiary-butyl 5-hydroxy-pyrimidines |
| JPWO2002085858A1 (ja) * | 2001-04-20 | 2004-08-12 | 旭硝子株式会社 | 精製されたピペリジン誘導体の製造方法 |
| JP4342940B2 (ja) * | 2001-08-06 | 2009-10-14 | 塩野義製薬株式会社 | ５−メチル−１−フェニル−２（１ｈ）ピリジノンの製造方法 |
| CN1218942C (zh) | 2002-06-11 | 2005-09-14 | 中南大学湘雅医学院 | 抗纤维化吡啶酮化合物及其生产工艺方法 |
| CN100396669C (zh) * | 2006-03-15 | 2008-06-25 | 浙江省医学科学院 | 一种抗纤维化药物吡非尼酮的制备方法 |
| MX2007006349A (es) * | 2007-05-29 | 2009-02-18 | Cell Therapy And Technology S | Nuevo proceso de sintesis para la obtencion de 5-metil-1-fenil-2-(ih)-piridona, composicion y uso de la misma. |
| WO2008157786A1 (fr) | 2007-06-20 | 2008-12-24 | Auspex Pharmaceutical, Inc. | N-aryle pyridinones substituees a fonction d'inhibiteurs fibrogenes |
| WO2009035598A1 (fr) * | 2007-09-10 | 2009-03-19 | Concert Pharmaceuticals, Inc. | Pirfénidone déutérée |
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2010
- 2010-06-01 TW TW099117538A patent/TWI434833B/zh active
- 2010-06-02 NZ NZ596872A patent/NZ596872A/en not_active IP Right Cessation
- 2010-06-02 EA EA201101695A patent/EA021826B1/ru not_active IP Right Cessation
- 2010-06-02 GE GEAP201012512A patent/GEP20156223B/en unknown
- 2010-06-02 WO PCT/US2010/037090 patent/WO2010141600A2/fr not_active Ceased
- 2010-06-02 UA UAA201115405A patent/UA106759C2/uk unknown
- 2010-06-02 SG SG2011089455A patent/SG176648A1/en unknown
- 2010-06-02 RS RS20150376A patent/RS54031B1/sr unknown
- 2010-06-02 CN CN2010800245047A patent/CN102482255A/zh active Pending
- 2010-06-02 ES ES10784021.7T patent/ES2538103T3/es active Active
- 2010-06-02 BR BRPI1011015A patent/BRPI1011015B8/pt not_active IP Right Cessation
- 2010-06-02 MA MA34508A patent/MA33489B1/fr unknown
- 2010-06-02 PT PT107840217T patent/PT2440543E/pt unknown
- 2010-06-02 EP EP10784021.7A patent/EP2440543B1/fr active Active
- 2010-06-02 HU HUE10784021A patent/HUE026014T2/en unknown
- 2010-06-02 JP JP2012514087A patent/JP5848244B2/ja active Active
- 2010-06-02 PE PE2011002044A patent/PE20120398A1/es not_active Application Discontinuation
- 2010-06-02 HR HRP20150696TT patent/HRP20150696T1/hr unknown
- 2010-06-02 SI SI201030938T patent/SI2440543T1/sl unknown
- 2010-06-02 CA CA2764043A patent/CA2764043C/fr active Active
- 2010-06-02 AU AU2010256693A patent/AU2010256693B2/en not_active Revoked
- 2010-06-02 DK DK10784021.7T patent/DK2440543T3/en active
- 2010-06-02 PL PL10784021T patent/PL2440543T3/pl unknown
- 2010-06-02 AP AP2012006052A patent/AP3630A/xx active
- 2010-06-02 MX MX2011012654A patent/MX2011012654A/es active IP Right Grant
- 2010-06-02 KR KR1020117029855A patent/KR101734858B1/ko active Active
- 2010-06-02 US US12/792,387 patent/US20110003863A1/en not_active Abandoned
- 2010-06-02 MY MYPI2011005818A patent/MY162443A/en unknown
- 2010-06-03 AR ARP100101971A patent/AR076974A1/es active IP Right Grant
-
2011
- 2011-09-26 US US13/244,786 patent/US8519140B2/en active Active
- 2011-11-23 IL IL216565A patent/IL216565A/en active IP Right Grant
- 2011-11-30 ZA ZA2011/08794A patent/ZA201108794B/en unknown
- 2011-12-01 TN TNP2011000615A patent/TN2011000615A1/en unknown
- 2011-12-02 CL CL2011003069A patent/CL2011003069A1/es unknown
- 2011-12-05 NI NI201100211A patent/NI201100211A/es unknown
- 2011-12-05 HN HN2011003187A patent/HN2011003187A/es unknown
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2013
- 2013-07-22 US US13/947,643 patent/US20130345430A1/en not_active Abandoned
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2014
- 2014-04-08 US US14/247,357 patent/US20140221660A1/en not_active Abandoned
- 2014-11-11 US US14/538,426 patent/US20150065720A1/en not_active Abandoned
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2015
- 2015-08-20 US US14/830,999 patent/US20150368200A1/en not_active Abandoned
- 2015-10-15 JP JP2015203886A patent/JP2016026196A/ja active Pending
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