PE20120398A1 - Metodo mejorado para sintetizar pirfenidona - Google Patents
Metodo mejorado para sintetizar pirfenidonaInfo
- Publication number
- PE20120398A1 PE20120398A1 PE2011002044A PE2011002044A PE20120398A1 PE 20120398 A1 PE20120398 A1 PE 20120398A1 PE 2011002044 A PE2011002044 A PE 2011002044A PE 2011002044 A PE2011002044 A PE 2011002044A PE 20120398 A1 PE20120398 A1 PE 20120398A1
- Authority
- PE
- Peru
- Prior art keywords
- pyrphenidone
- solvent
- purified
- toluene
- extraction
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 5
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 9
- 239000002904 solvent Substances 0.000 abstract 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 238000000605 extraction Methods 0.000 abstract 3
- 239000011877 solvent mixture Substances 0.000 abstract 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 2
- 239000003637 basic solution Substances 0.000 abstract 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- SOHMZGMHXUQHGE-UHFFFAOYSA-N 5-methyl-1h-pyridin-2-one Chemical compound CC1=CC=C(O)N=C1 SOHMZGMHXUQHGE-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 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)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Agronomy & Crop Science (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (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
REFERIDA A UN METODO PARA SINTETIZAR PIRFENIDONA QUE COMPRENDE MEZCLAR BROMOBENCENO, 5-METIL-2-PIRIDONA, OXIDO CUPROSO, UN SOLVENTE ORGANICO TAL COMO DIMETILFORMAMIDA Y UNA BASE INORGANICA TAL COMO CARBONATO DE POTASIO Y LA EXTRACCION DE LA PIRFENIDONA CON UN SOLVENTE DE EXTRACCION ORGANICO QUE COMPRENDE TOLUENO. TAMBIEN ESTA REFERIDA A UN METODO DE CRISTALIZACION DE PIRFENIDONA DESDE UNA MEZCLA DE SOLVENTES QUE COMPRENDE HEPTANOS Y TOLUENO Y UN METODO DE RECRISTALIZACION QUE COMPRENDE DISOLVER UNA PORCION DE PIRFENIDONA PURIFICADA EN UNA SOLUCION ACUOSA ACIDA, QUE COMPRENDE ACIDO CLORHIDRICO, A ALTA TEMPERATURA PARA FORMAR UNA SOLUCION DE PIRFENIDONA, A LA CUAL SE LE AGREGA UNA SOLUCION BASICA HASTA OBTENER UN PH DE 11 Y LUEGO ENFRIAR LA SOLUCION BASICA HASTA UNA TEMPERATURA MENOR DE 20 ºC, OBTENIENDOSE LA PIRFENIDONA RECRISTALIZADA
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18358809P | 2009-06-03 | 2009-06-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20120398A1 true PE20120398A1 (es) | 2012-05-13 |
Family
ID=43298478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2011002044A PE20120398A1 (es) | 2009-06-03 | 2010-06-02 | Metodo mejorado para sintetizar pirfenidona |
Country Status (35)
| Country | Link |
|---|---|
| US (6) | US20110003863A1 (es) |
| EP (1) | EP2440543B1 (es) |
| JP (2) | JP5848244B2 (es) |
| KR (1) | KR101734858B1 (es) |
| CN (1) | CN102482255A (es) |
| AP (1) | AP3630A (es) |
| AR (1) | AR076974A1 (es) |
| AU (1) | AU2010256693B2 (es) |
| BR (1) | BRPI1011015B8 (es) |
| CA (1) | CA2764043C (es) |
| CL (1) | CL2011003069A1 (es) |
| DK (1) | DK2440543T3 (es) |
| EA (1) | EA021826B1 (es) |
| ES (1) | ES2538103T3 (es) |
| GE (1) | GEP20156223B (es) |
| HN (1) | HN2011003187A (es) |
| HR (1) | HRP20150696T1 (es) |
| HU (1) | HUE026014T2 (es) |
| IL (1) | IL216565A (es) |
| MA (1) | MA33489B1 (es) |
| MX (1) | MX2011012654A (es) |
| MY (1) | MY162443A (es) |
| NI (1) | NI201100211A (es) |
| NZ (1) | NZ596872A (es) |
| PE (1) | PE20120398A1 (es) |
| PL (1) | PL2440543T3 (es) |
| PT (1) | PT2440543E (es) |
| RS (1) | RS54031B1 (es) |
| SG (1) | SG176648A1 (es) |
| SI (1) | SI2440543T1 (es) |
| TN (1) | TN2011000615A1 (es) |
| TW (1) | TWI434833B (es) |
| UA (1) | UA106759C2 (es) |
| WO (1) | WO2010141600A2 (es) |
| ZA (1) | ZA201108794B (es) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3034994A1 (en) | 2008-06-03 | 2009-12-10 | Intermune, Inc. | Substituted aryl-2 pyridone compounds and use thereof 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 |
| CA2824432C (en) | 2011-01-31 | 2021-10-19 | Genoa Pharmaceuticals, 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 |
| NZ722927A (en) | 2014-01-10 | 2022-07-29 | Avalyn Pharma Inc | Aerosol pirfenidone and pyridone analog compounds and uses thereof |
| CA2943363A1 (en) | 2014-04-02 | 2015-10-08 | Intermune, Inc. | Anti-fibrotic pyridinones |
| CA2958195A1 (en) * | 2014-08-15 | 2016-02-18 | PixarBio Corporation | Compositions for inhibiting inflammation in a subject with a spinal cord injury and methods of using the same |
| 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 |
| CA3108048A1 (en) | 2017-07-31 | 2019-02-07 | Washington University | Pirfenidone derivatives for modulation of b lymphocyte activity and organ protection |
| 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 |
| WO2021215856A1 (ko) * | 2020-04-22 | 2021-10-28 | 영진약품 주식회사 | 안전성과 안정성이 개선된 피르페니돈을 포함하는 장용성 제제 및 이의 제조방법 |
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 |
| WO2002085858A1 (en) * | 2001-04-20 | 2002-10-31 | Asahi Glass Company, Limited | Process for producing purified piperidine derivative |
| 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. |
| JP5587184B2 (ja) * | 2007-06-20 | 2014-09-10 | オースペックス・ファーマシューティカルズ・インコーポレイテッド | 繊維症阻害剤としての置換ｎ−アリールピリジノン |
| US20090131485A1 (en) * | 2007-09-10 | 2009-05-21 | Concert Pharmaceuticals, Inc. | Deuterated pirfenidone |
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2010
- 2010-06-01 TW TW099117538A patent/TWI434833B/zh active
- 2010-06-02 KR KR1020117029855A patent/KR101734858B1/ko active Active
- 2010-06-02 DK DK10784021.7T patent/DK2440543T3/en active
- 2010-06-02 RS RS20150376A patent/RS54031B1/sr unknown
- 2010-06-02 UA UAA201115405A patent/UA106759C2/uk unknown
- 2010-06-02 MY MYPI2011005818A patent/MY162443A/en unknown
- 2010-06-02 GE GEAP201012512A patent/GEP20156223B/en unknown
- 2010-06-02 EP EP10784021.7A patent/EP2440543B1/en active Active
- 2010-06-02 SI SI201030938T patent/SI2440543T1/sl unknown
- 2010-06-02 NZ NZ596872A patent/NZ596872A/en not_active IP Right Cessation
- 2010-06-02 AU AU2010256693A patent/AU2010256693B2/en not_active Revoked
- 2010-06-02 AP AP2012006052A patent/AP3630A/xx active
- 2010-06-02 MX MX2011012654A patent/MX2011012654A/es active IP Right Grant
- 2010-06-02 PT PT107840217T patent/PT2440543E/pt unknown
- 2010-06-02 US US12/792,387 patent/US20110003863A1/en not_active Abandoned
- 2010-06-02 PE PE2011002044A patent/PE20120398A1/es not_active Application Discontinuation
- 2010-06-02 SG SG2011089455A patent/SG176648A1/en unknown
- 2010-06-02 MA MA34508A patent/MA33489B1/fr unknown
- 2010-06-02 BR BRPI1011015A patent/BRPI1011015B8/pt not_active IP Right Cessation
- 2010-06-02 HU HUE10784021A patent/HUE026014T2/en unknown
- 2010-06-02 EA EA201101695A patent/EA021826B1/ru not_active IP Right Cessation
- 2010-06-02 HR HRP20150696TT patent/HRP20150696T1/hr unknown
- 2010-06-02 JP JP2012514087A patent/JP5848244B2/ja active Active
- 2010-06-02 ES ES10784021.7T patent/ES2538103T3/es active Active
- 2010-06-02 PL PL10784021T patent/PL2440543T3/pl unknown
- 2010-06-02 CN CN2010800245047A patent/CN102482255A/zh active Pending
- 2010-06-02 CA CA2764043A patent/CA2764043C/en active Active
- 2010-06-02 WO PCT/US2010/037090 patent/WO2010141600A2/en not_active Ceased
- 2010-06-03 AR ARP100101971A patent/AR076974A1/es active IP Right Grant
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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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