PE20100262A1 - Nuevo procedimiento de sintesis de la agomelatina - Google Patents

Nuevo procedimiento de sintesis de la agomelatina

Info

Publication number
PE20100262A1
PE20100262A1 PE2009000985A PE2009000985A PE20100262A1 PE 20100262 A1 PE20100262 A1 PE 20100262A1 PE 2009000985 A PE2009000985 A PE 2009000985A PE 2009000985 A PE2009000985 A PE 2009000985A PE 20100262 A1 PE20100262 A1 PE 20100262A1
Authority
PE
Peru
Prior art keywords
compound
agomelatin
chuesulphonate
synthesis
reaction
Prior art date
Application number
PE2009000985A
Other languages
English (en)
Inventor
Christophe Hardouin
Nicolas Bragnier
Jean-Pierre Lecouve
Original Assignee
Servier Lab
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=40352219&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=PE20100262(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Servier Lab filed Critical Servier Lab
Publication of PE20100262A1 publication Critical patent/PE20100262A1/es

Links

Classifications

    • 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
    • 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
    • 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
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • 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
    • 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
    • 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
    • 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

SE REFIERE A UN PROCESO QUE COMPRENDE: REACCION DE 7-METOXI-1-NAFTOL, SOBRE EL QUE SE CONDENSA, EN PRESENCIA DE PALADIO DONDE EL GRUPO HIDROXI SE TRANSFORMA EN UN GRUPO SALIENTE COMO HALO, TOSILATO O TRIFLUOROMETANOSULFONATO Y EL COMPUESTO CH2=CH-R, DONDE R ES ACETAMIDA O (a); R´Y R´´ SON CADA UNO ALQUILO (C1-C6) O JUNTOS FORMAN ALQUILENO (C2-C3) PARA FORMAR EL COMPUESTO (IV), QUE SE SOMETE A UNA HIDROGENACION CATALITICA Y LUEGO MEDIANTE UNA HIDROLISIS BASICA O ACIDA Y REACCION CON EL ACETATO DE SODIO Y DE ANHIDRIDO ACETICO DA LUGAR AL COMPUESTO AGOMELATINA. DICHO COMPUESTO ES UTIL EN EL TRATAMIENTO DE TRASTORNOS DEL SISTEMA NERVIOSO CENTRAL
PE2009000985A 2008-08-05 2009-07-24 Nuevo procedimiento de sintesis de la agomelatina PE20100262A1 (es)

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
PE20100262A1 true PE20100262A1 (es) 2010-04-10

Family

ID=40352219

Family Applications (1)

Application Number Title Priority Date Filing Date
PE2009000985A PE20100262A1 (es) 2008-08-05 2009-07-24 Nuevo procedimiento de sintesis de la agomelatina

Country Status (47)

Country Link
US (2) US8212077B2 (es)
EP (1) EP2151428B1 (es)
JP (1) JP5112400B2 (es)
KR (1) KR101127278B1 (es)
CN (1) CN101643434B (es)
AP (1) AP3167A (es)
AR (1) AR074888A1 (es)
AT (1) ATE548345T1 (es)
AU (1) AU2009203105B2 (es)
BR (1) BRPI0902825A2 (es)
CA (1) CA2674760C (es)
CL (1) CL2009001686A1 (es)
CO (2) CO6120163A1 (es)
CR (2) CR10960A (es)
CU (1) CU23859B1 (es)
CY (1) CY1112829T1 (es)
DK (1) DK2151428T3 (es)
EA (1) EA017848B1 (es)
EC (1) ECSP099560A (es)
ES (1) ES2384021T3 (es)
FR (1) FR2934859B1 (es)
GE (1) GEP20125512B (es)
GT (1) GT200900222A (es)
HK (1) HK1141007A1 (es)
HN (1) HN2009001436A (es)
HR (1) HRP20120407T1 (es)
IL (1) IL200137A (es)
JO (1) JO2818B1 (es)
MA (1) MA31416B1 (es)
ME (1) ME00928B (es)
MX (1) MX2009008196A (es)
MY (1) MY144936A (es)
NI (1) NI200900153A (es)
NZ (1) NZ578825A (es)
PE (1) PE20100262A1 (es)
PL (1) PL2151428T3 (es)
PT (1) PT2151428E (es)
RS (1) RS52352B (es)
SA (1) SA109300502B1 (es)
SG (1) SG158836A1 (es)
SI (1) SI2151428T1 (es)
SV (1) SV2009003343A (es)
TW (1) TWI398428B (es)
UA (1) UA102220C2 (es)
UY (1) UY32012A (es)
WO (1) WO2010015745A1 (es)
ZA (1) ZA200905335B (es)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
ECSP099560A (es) 2010-03-31
MX2009008196A (es) 2010-03-01
UA102220C2 (ru) 2013-06-25
EP2151428B1 (fr) 2012-03-07
PT2151428E (pt) 2012-04-18
SA109300502B1 (ar) 2013-11-27
US20120245363A1 (en) 2012-09-27
CO6120150A1 (es) 2010-01-29
EA017848B1 (ru) 2013-03-29
IL200137A0 (en) 2010-05-31
IL200137A (en) 2013-03-24
CR10960A (es) 2009-09-14
WO2010015745A1 (fr) 2010-02-11
GT200900222A (es) 2010-03-15
CR20150055A (es) 2015-05-18
HRP20120407T1 (hr) 2012-06-30
FR2934859A1 (fr) 2010-02-12
SG158836A1 (en) 2010-02-26
AP3167A (en) 2015-03-31
JP2010059153A (ja) 2010-03-18
PL2151428T3 (pl) 2012-07-31
ZA200905335B (en) 2010-05-26
FR2934859B1 (fr) 2010-08-13
RS52352B (en) 2012-12-31
AU2009203105B2 (en) 2013-09-05
HK1141007A1 (en) 2010-10-29
AR074888A1 (es) 2011-02-23
ATE548345T1 (de) 2012-03-15
JO2818B1 (en) 2014-09-15
AU2009203105A1 (en) 2010-02-25
AP2009004944A0 (en) 2009-08-31
CA2674760C (fr) 2012-04-17
ES2384021T3 (es) 2012-06-28
BRPI0902825A2 (pt) 2011-04-26
GEP20125512B (en) 2012-05-10
CO6120163A1 (es) 2010-01-29
HN2009001436A (es) 2011-09-22
CY1112829T1 (el) 2016-02-10
US8212077B2 (en) 2012-07-03
EP2151428A1 (fr) 2010-02-10
MA31416B1 (fr) 2010-06-01
US20100036162A1 (en) 2010-02-11
NI200900153A (es) 2010-03-25
UY32012A (es) 2010-01-29
SV2009003343A (es) 2010-02-01
ME00928B (me) 2012-06-20
MY144936A (en) 2011-11-29
EA200900946A1 (ru) 2010-04-30
CA2674760A1 (fr) 2010-02-05
CN101643434B (zh) 2012-07-25
CN101643434A (zh) 2010-02-10
CU20090137A7 (es) 2012-03-15
CU23859B1 (es) 2013-02-26
DK2151428T3 (da) 2012-07-02
NZ578825A (en) 2010-12-24
TWI398428B (zh) 2013-06-11
TW201008899A (en) 2010-03-01
KR20100017069A (ko) 2010-02-16
CL2009001686A1 (es) 2010-07-19
KR101127278B1 (ko) 2012-04-12
JP5112400B2 (ja) 2013-01-09
SI2151428T1 (sl) 2012-06-29

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