CO6120150A1 - Nuevo procedimiento de sintesis de la agomelatina - Google Patents
Nuevo procedimiento de sintesis de la agomelatinaInfo
- Publication number
- CO6120150A1 CO6120150A1 CO09080215A CO09080215A CO6120150A1 CO 6120150 A1 CO6120150 A1 CO 6120150A1 CO 09080215 A CO09080215 A CO 09080215A CO 09080215 A CO09080215 A CO 09080215A CO 6120150 A1 CO6120150 A1 CO 6120150A1
- Authority
- CO
- Colombia
- Prior art keywords
- formula
- compound
- give rise
- iii
- defined above
- Prior art date
Links
Classifications
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- 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
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- 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
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- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- 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
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/08—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/90—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated
- C07C233/91—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated with carbon atoms of the carboxamide groups bound to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Reproductive Health (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Gynecology & Obstetrics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Psychology (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Indole Compounds (AREA)
Abstract
Procedimiento de síntesis industrial del compuesto de fórmula (I):caracterizado porque se pone a reaccionar el 7-metoxi-1-naftol de fórmula (II):sobre el que se condensa, en presencia de paladio, después que cuya función hidroxi se transforma en grupo saliente como el grupo halógeno, tosilato o trifluorometanosulfonato, el compuesto de fórmula (III): CH2=CH-R (III): en el que R' y R", idénticos o diferentes, representan cada uno un grupo alquilo (C1-C6) lineal o ramificado, o R' y R" forman juntos una cadena alquileno (C2-C3), el ciclo así formado puede fusionarse con un fenilo, para dar lugar al compuesto de fórmula (IV):en la que R es tal como se ha definido anteriormente, que se somete a una hidrogenación catalítica para dar lugar al compuesto de fórmula (V):en la que R es tal como se ha definido anteriormente, que se somete a una hidrólisis básica o ácida, o a un sistema binario reductor/ácido para dar lugar al compuesto de fórmula (VI) o a su clorhidrato:que se somete sucesivamente a la acción de acetato de sodio y de anhídrido acético para dar lugar al compuesto de fórmula (I) que se aísla en la forma de un sólido.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0804465A FR2934859B1 (fr) | 2008-08-05 | 2008-08-05 | Nouveau procede de synthese de l'agomelatine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CO6120150A1 true CO6120150A1 (es) | 2010-01-29 |
Family
ID=40352219
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CO09080223A CO6120163A1 (es) | 2008-08-05 | 2009-07-31 | Nuevo procedimeinto de sintesis de la agomelatina |
| CO09080215A CO6120150A1 (es) | 2008-08-05 | 2009-07-31 | Nuevo procedimiento de sintesis de la agomelatina |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CO09080223A CO6120163A1 (es) | 2008-08-05 | 2009-07-31 | Nuevo procedimeinto de sintesis de la agomelatina |
Country Status (47)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102190594A (zh) | 2010-03-17 | 2011-09-21 | 上海医药工业研究院 | 阿戈美拉汀氯化氢水合物及其制备方法 |
| WO2011154140A2 (en) | 2010-06-10 | 2011-12-15 | Gador S.A. | New process for the preparation of n-[2-(7-methoxy-1-naphthyl)-ethyl]acetamide and new crystalline form |
| CN102229541A (zh) * | 2010-09-17 | 2011-11-02 | 福建广生堂药业有限公司 | 阿戈美拉汀n-[2-(7-甲氧基萘-1-基)乙基]乙酰胺的制备方法 |
| CN102531956B (zh) * | 2010-12-21 | 2014-07-09 | 浙江九洲药业股份有限公司 | 用于制备阿戈美拉汀的中间体及相关制备方法 |
| FR2970001B1 (fr) * | 2011-01-05 | 2013-01-04 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
| EP2562151A1 (en) * | 2011-08-25 | 2013-02-27 | Dr. Reddy's Laboratories Ltd. | Processes for the preparation of agomelatine and its intermediates |
| ITMI20121444A1 (it) | 2012-08-27 | 2014-02-28 | Procos Spa | Processo per la produzione di agomelatine |
| WO2014072998A1 (en) | 2012-11-07 | 2014-05-15 | Cadila Healthcare Limited | An improved process for preparation of agomelatine |
| JP6159415B2 (ja) * | 2013-11-20 | 2017-07-05 | マナック株式会社 | 含臭素ｎ−フェニルジアクリルイミド誘導体及びその製造方法 |
| FR3014434B1 (fr) * | 2013-12-05 | 2015-12-25 | Servier Lab | Nouveau procede de synthese du 7-methoxy-naphtalene-1-carbaldehyde et application a la synthese de l'agomelatine |
| FR3014437B1 (fr) * | 2013-12-05 | 2016-12-23 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
| CN114394906A (zh) * | 2022-03-24 | 2022-04-26 | 中孚药业股份有限公司 | 一种阿戈美拉汀中间体的制备方法 |
| CN115872887B (zh) * | 2022-12-30 | 2023-07-07 | 上海国创医药股份有限公司 | 一种阿戈美拉汀的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2658818B1 (fr) * | 1990-02-27 | 1993-12-31 | Adir Cie | Nouveaux derives a structure naphtalenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| DE19825454A1 (de) * | 1998-06-06 | 1999-12-16 | Aventis Res & Tech Gmbh & Co | Verfahren zur Herstellung von aromatischen Olefinen unter Katalyse von Palladiumkatalysatoren mit Phosphitliganden |
| FR2784375B1 (fr) * | 1998-10-12 | 2000-11-24 | Adir | Nouveaux derives cycliques a chaine cycloalkylenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| DE19859684A1 (de) * | 1998-12-23 | 2000-06-29 | Bayer Ag | Verfahren zur Herstellung von Fluor enthaltenden Phenethylaminen sowie neue, Fluor enthalende beta-Iminovinyl- und beta-Iminoethylbenzole |
| DE19931116A1 (de) * | 1999-07-06 | 2001-01-11 | Bayer Ag | Verfahren zur Herstellung von Phenethylaminen und neue chemische Verbindungen |
| FR2866335B1 (fr) * | 2004-02-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
| EP1732531A2 (en) * | 2004-02-25 | 2006-12-20 | La Jolla Pharmaceutical Company | Amines and amides for the treatment of diseases |
| JP4870660B2 (ja) * | 2004-03-15 | 2012-02-08 | アノーメッド インコーポレイティド | Ｃｘｃｒ４アンタゴニストの合成プロセス |
| JP5015016B2 (ja) * | 2006-02-07 | 2012-08-29 | 大正製薬株式会社 | １０ａ−アザライド化合物 |
| CN101638376B (zh) | 2008-07-29 | 2011-04-27 | 江苏恩华药业股份有限公司 | 阿戈美拉汀的制备方法及其中间体 |
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2008
- 2008-08-05 FR FR0804465A patent/FR2934859B1/fr not_active Expired - Fee Related
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2009
- 2009-07-24 PE PE2009000985A patent/PE20100262A1/es not_active Application Discontinuation
- 2009-07-28 UY UY0001032012A patent/UY32012A/es not_active Application Discontinuation
- 2009-07-28 SG SG200905038-6A patent/SG158836A1/en unknown
- 2009-07-29 MY MYPI20093143A patent/MY144936A/en unknown
- 2009-07-29 CR CR10960A patent/CR10960A/es unknown
- 2009-07-29 IL IL200137A patent/IL200137A/en not_active IP Right Cessation
- 2009-07-29 AU AU2009203105A patent/AU2009203105B2/en not_active Ceased
- 2009-07-29 SV SV2009003343A patent/SV2009003343A/es active IP Right Grant
- 2009-07-30 NI NI200900153A patent/NI200900153A/es unknown
- 2009-07-30 ZA ZA200905335A patent/ZA200905335B/xx unknown
- 2009-07-31 MX MX2009008196A patent/MX2009008196A/es active IP Right Grant
- 2009-07-31 CU CU2009000137A patent/CU23859B1/es active IP Right Grant
- 2009-07-31 CO CO09080223A patent/CO6120163A1/es active IP Right Grant
- 2009-07-31 MA MA32134A patent/MA31416B1/fr unknown
- 2009-07-31 CO CO09080215A patent/CO6120150A1/es active IP Right Grant
- 2009-08-03 JO JO2009287A patent/JO2818B1/en active
- 2009-08-03 GE GEAP200911403A patent/GEP20125512B/en unknown
- 2009-08-03 ME MEP-2009-257A patent/ME00928B/me unknown
- 2009-08-03 CA CA2674760A patent/CA2674760C/fr not_active Expired - Fee Related
- 2009-08-03 NZ NZ578825A patent/NZ578825A/en not_active IP Right Cessation
- 2009-08-03 AP AP2009004944A patent/AP3167A/xx active
- 2009-08-03 CL CL2009001686A patent/CL2009001686A1/es unknown
- 2009-08-04 EP EP09290606A patent/EP2151428B1/fr active Active
- 2009-08-04 RS RS20120236A patent/RS52352B/en unknown
- 2009-08-04 AT AT09290606T patent/ATE548345T1/de active
- 2009-08-04 PL PL09290606T patent/PL2151428T3/pl unknown
- 2009-08-04 WO PCT/FR2009/000972 patent/WO2010015745A1/fr active Application Filing
- 2009-08-04 HN HN2009001436A patent/HN2009001436A/es unknown
- 2009-08-04 UA UAA200908227A patent/UA102220C2/ru unknown
- 2009-08-04 DK DK09290606.4T patent/DK2151428T3/da active
- 2009-08-04 US US12/462,469 patent/US8212077B2/en not_active Expired - Fee Related
- 2009-08-04 SA SA109300502A patent/SA109300502B1/ar unknown
- 2009-08-04 AR ARP090102983A patent/AR074888A1/es unknown
- 2009-08-04 TW TW098126191A patent/TWI398428B/zh not_active IP Right Cessation
- 2009-08-04 PT PT09290606T patent/PT2151428E/pt unknown
- 2009-08-04 BR BRPI0902825-0A patent/BRPI0902825A2/pt not_active Application Discontinuation
- 2009-08-04 ES ES09290606T patent/ES2384021T3/es active Active
- 2009-08-04 SI SI200930252T patent/SI2151428T1/sl unknown
- 2009-08-04 KR KR1020090071643A patent/KR101127278B1/ko active IP Right Grant
- 2009-08-04 EA EA200900946A patent/EA017848B1/ru not_active IP Right Cessation
- 2009-08-05 JP JP2009182089A patent/JP5112400B2/ja not_active Expired - Fee Related
- 2009-08-05 EC EC2009009560A patent/ECSP099560A/es unknown
- 2009-08-05 CN CN2009101603096A patent/CN101643434B/zh not_active Expired - Fee Related
- 2009-08-07 GT GT200900222A patent/GT200900222A/es unknown
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2010
- 2010-08-09 HK HK10107582.7A patent/HK1141007A1/xx not_active IP Right Cessation
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2012
- 2012-05-11 HR HRP20120407AT patent/HRP20120407T1/hr unknown
- 2012-06-01 US US13/486,391 patent/US20120245363A1/en not_active Abandoned
- 2012-06-07 CY CY20121100519T patent/CY1112829T1/el unknown
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2015
- 2015-02-05 CR CR20150055A patent/CR20150055A/es unknown
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