ES2538103T3 - Método de síntesis mejorado para la síntesis de pirfenidona - Google Patents
Método de síntesis mejorado para la síntesis de pirfenidona Download PDFInfo
- Publication number
- ES2538103T3 ES2538103T3 ES10784021.7T ES10784021T ES2538103T3 ES 2538103 T3 ES2538103 T3 ES 2538103T3 ES 10784021 T ES10784021 T ES 10784021T ES 2538103 T3 ES2538103 T3 ES 2538103T3
- Authority
- ES
- Spain
- Prior art keywords
- pirfenidone
- synthesis
- improved
- bromobenzene
- synthesis method
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 title abstract 3
- 229960003073 pirfenidone Drugs 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000001308 synthesis method Methods 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 abstract 4
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 abstract 1
- SOHMZGMHXUQHGE-UHFFFAOYSA-N 5-methyl-1h-pyridin-2-one Chemical compound CC1=CC=C(O)N=C1 SOHMZGMHXUQHGE-UHFFFAOYSA-N 0.000 abstract 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 abstract 1
- 239000005751 Copper oxide Substances 0.000 abstract 1
- 229910000431 copper oxide Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000002194 synthesizing effect 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)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18358809P | 2009-06-03 | 2009-06-03 | |
| US183588P | 2009-06-03 | ||
| PCT/US2010/037090 WO2010141600A2 (en) | 2009-06-03 | 2010-06-02 | Improved method for synthesizing pirfenidone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2538103T3 true ES2538103T3 (es) | 2015-06-17 |
Family
ID=43298478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10784021.7T Active ES2538103T3 (es) | 2009-06-03 | 2010-06-02 | Método de síntesis mejorado para la síntesis de pirfenidona |
Country Status (35)
| Country | Link |
|---|---|
| US (6) | US20110003863A1 (OSRAM) |
| EP (1) | EP2440543B1 (OSRAM) |
| JP (2) | JP5848244B2 (OSRAM) |
| KR (1) | KR101734858B1 (OSRAM) |
| CN (1) | CN102482255A (OSRAM) |
| AP (1) | AP3630A (OSRAM) |
| AR (1) | AR076974A1 (OSRAM) |
| AU (1) | AU2010256693B2 (OSRAM) |
| BR (1) | BRPI1011015B8 (OSRAM) |
| CA (1) | CA2764043C (OSRAM) |
| CL (1) | CL2011003069A1 (OSRAM) |
| DK (1) | DK2440543T3 (OSRAM) |
| EA (1) | EA021826B1 (OSRAM) |
| ES (1) | ES2538103T3 (OSRAM) |
| GE (1) | GEP20156223B (OSRAM) |
| HN (1) | HN2011003187A (OSRAM) |
| HR (1) | HRP20150696T1 (OSRAM) |
| HU (1) | HUE026014T2 (OSRAM) |
| IL (1) | IL216565A (OSRAM) |
| MA (1) | MA33489B1 (OSRAM) |
| MX (1) | MX2011012654A (OSRAM) |
| MY (1) | MY162443A (OSRAM) |
| NI (1) | NI201100211A (OSRAM) |
| NZ (1) | NZ596872A (OSRAM) |
| PE (1) | PE20120398A1 (OSRAM) |
| PL (1) | PL2440543T3 (OSRAM) |
| PT (1) | PT2440543E (OSRAM) |
| RS (1) | RS54031B1 (OSRAM) |
| SG (1) | SG176648A1 (OSRAM) |
| SI (1) | SI2440543T1 (OSRAM) |
| TN (1) | TN2011000615A1 (OSRAM) |
| TW (1) | TWI434833B (OSRAM) |
| UA (1) | UA106759C2 (OSRAM) |
| WO (1) | WO2010141600A2 (OSRAM) |
| ZA (1) | ZA201108794B (OSRAM) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2296653B1 (en) | 2008-06-03 | 2016-01-27 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| US10105356B2 (en) | 2011-01-31 | 2018-10-23 | Avalyn Pharma Inc. | Aerosol pirfenidone and pyridone analog compounds and uses thereof |
| EP4059499A1 (en) | 2011-01-31 | 2022-09-21 | 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 |
| JP7066321B2 (ja) | 2014-01-10 | 2022-05-13 | アヴァリン ファーマ インク． | エアロゾルのピルフェニドン及びピリドンのアナログの化合物、及び、その使用 |
| JP6525437B2 (ja) | 2014-04-02 | 2019-06-05 | インターミューン， インコーポレイテッド | 抗線維性ピリジノン |
| BR112017002980A2 (pt) * | 2014-08-15 | 2017-12-12 | Pixarbio Corp | composição para inibir a inflamação em um indivíduo com um dano na coluna vertebral, método para tratar inflamação em um indivíduo tendo um dano na coluna vertebral e kit para produzir a composição |
| EP3307714A1 (en) * | 2015-01-26 | 2018-04-18 | Ulkar Kimya Sanayii Ve Ticaret A. S. | An improved method for the synthesis and purification of pirfenidone |
| 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 (en) * | 2016-01-14 | 2017-07-20 | Laurus Labs Limited | An improved process for the preparation of pirfenidone |
| US11066368B2 (en) | 2016-01-14 | 2021-07-20 | Laurus Labs Limited | Process for the preparation and particle size reduction of pirfenidone |
| WO2017130166A1 (en) * | 2016-01-31 | 2017-08-03 | Granules India Limited | An improved process for the preparation of highly pure anti-fibrotic drug |
| CA2937365C (en) | 2016-03-29 | 2018-09-18 | F. Hoffmann-La Roche Ag | Granulate formulation of 5-methyl-1-phenyl-2-(1h)-pyridone and method of making the same |
| 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 (en) * | 2016-11-07 | 2018-05-11 | Msn Laboratories Private Limited, R&D Center | Improved process for the preparation of pure 5-methyl-1-phenyl-2-1 (h)-pyridone |
| WO2018178996A1 (en) * | 2017-03-28 | 2018-10-04 | Natco Pharma Limited | Improved process for the preparation of pirfenidone |
| WO2019028062A1 (en) | 2017-07-31 | 2019-02-07 | Washington University | PIRFENIDONE DERIVATIVES FOR MODULATION OF B-LYMPHOCYTE ACTIVITY AND PROTECTION OF ORGANS |
| EP3494965B1 (en) | 2017-12-11 | 2021-06-02 | Laurus Labs Limited | An improved process for the preparation of pirfenidone |
| 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 |
| WO1992013844A1 (en) * | 1991-01-31 | 1992-08-20 | 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 |
| WO2003014087A1 (fr) * | 2001-08-06 | 2003-02-20 | Asahi Glass Company, Limited | Procede de preparation de 5-methyl-1-phenyl-2(1h)-pyridinone |
| 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. |
| CN101842355A (zh) * | 2007-06-20 | 2010-09-22 | 奥斯拜客斯制药有限公司 | 作为纤维化抑制剂的取代的n-芳基吡啶酮 |
| US20090131485A1 (en) * | 2007-09-10 | 2009-05-21 | Concert Pharmaceuticals, Inc. | Deuterated pirfenidone |
-
2010
- 2010-06-01 TW TW099117538A patent/TWI434833B/zh active
- 2010-06-02 CN CN2010800245047A patent/CN102482255A/zh active Pending
- 2010-06-02 HR HRP20150696TT patent/HRP20150696T1/hr unknown
- 2010-06-02 ES ES10784021.7T patent/ES2538103T3/es active Active
- 2010-06-02 UA UAA201115405A patent/UA106759C2/uk unknown
- 2010-06-02 PL PL10784021T patent/PL2440543T3/pl unknown
- 2010-06-02 EP EP10784021.7A patent/EP2440543B1/en active Active
- 2010-06-02 CA CA2764043A patent/CA2764043C/en 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 NZ NZ596872A patent/NZ596872A/en not_active IP Right Cessation
- 2010-06-02 US US12/792,387 patent/US20110003863A1/en not_active Abandoned
- 2010-06-02 BR BRPI1011015A patent/BRPI1011015B8/pt not_active IP Right Cessation
- 2010-06-02 AP AP2012006052A patent/AP3630A/xx active
- 2010-06-02 EA EA201101695A patent/EA021826B1/ru not_active IP Right Cessation
- 2010-06-02 PT PT107840217T patent/PT2440543E/pt unknown
- 2010-06-02 MX MX2011012654A patent/MX2011012654A/es active IP Right Grant
- 2010-06-02 RS RS20150376A patent/RS54031B1/sr unknown
- 2010-06-02 KR KR1020117029855A patent/KR101734858B1/ko active Active
- 2010-06-02 AU AU2010256693A patent/AU2010256693B2/en not_active Revoked
- 2010-06-02 WO PCT/US2010/037090 patent/WO2010141600A2/en not_active Ceased
- 2010-06-02 DK DK10784021.7T patent/DK2440543T3/en active
- 2010-06-02 MA MA34508A patent/MA33489B1/fr unknown
- 2010-06-02 SG SG2011089455A patent/SG176648A1/en unknown
- 2010-06-02 SI SI201030938T patent/SI2440543T1/sl unknown
- 2010-06-02 GE GEAP201012512A patent/GEP20156223B/en unknown
- 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 HN HN2011003187A patent/HN2011003187A/es unknown
- 2011-12-05 NI NI201100211A patent/NI201100211A/es unknown
-
2013
- 2013-07-22 US US13/947,643 patent/US20130345430A1/en not_active Abandoned
-
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
-
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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