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PE20081390A1 - Procedimiento para producir derivados de amina opticamente activos - Google Patents

Procedimiento para producir derivados de amina opticamente activos

Info

Publication number
PE20081390A1
PE20081390A1 PE2008001369A PE2008001369A PE20081390A1 PE 20081390 A1 PE20081390 A1 PE 20081390A1 PE 2008001369 A PE2008001369 A PE 2008001369A PE 2008001369 A PE2008001369 A PE 2008001369A PE 20081390 A1 PE20081390 A1 PE 20081390A1
Authority
PE
Peru
Prior art keywords
optically active
furan
binap
procedure
tetrahidro
Prior art date
Application number
PE2008001369A
Other languages
English (en)
Inventor
Shinichi Urayama
Eigo Mutou
Atsushi Inagaki
Takashi Okada
Shigeharu Sugisaki
Original Assignee
Takeda Pharmaceutical
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=36059992&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=PE20081390(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Takeda Pharmaceutical filed Critical Takeda Pharmaceutical
Publication of PE20081390A1 publication Critical patent/PE20081390A1/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • 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
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • 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
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/80—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Diabetes (AREA)
  • Pain & Pain Management (AREA)
  • Endocrinology (AREA)
  • Psychiatry (AREA)
  • Epidemiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Immunology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Emergency Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Psychology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Reproductive Health (AREA)
  • Hospice & Palliative Care (AREA)
  • Anesthesiology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)

Abstract

REFERIDA A UN PROCEDIMIENTO DE PREPARACION DE CRISTALES DE (S)-N-[2-(1,6,7,8-TETRAHIDRO-2H-INDENO[5,4-b]FURAN-8-IL)ETIL]PROPIONAMIDA, QUE COMPRENDE: a) LA PROPIONILACION DEL GRUPO AMINO DE (S)-2-(1,6,7,8-TETRAHIDRO-2H-INDENO[5,4-b]FURAN-8-IL)ETILAMINA O UNA SAL DEL MISMO OBTENIDA DEL PROCESO DE REDUCIR ASIMETRICAMENTE (E)-2-(1,6,7,8-TETRAHIDRO-2H-INDENO[5,4-b]FURAN-8-ILIDEN)ETILAMINA O UNA SAL DEL MISMO CON UN CATALIZADOR SELECCIONADO DE COMPLEJO FOSFINA RUTENIO OPTICAMENTE ACTIVO (Ru-BINAP), COMPLEJO FOSFINA RODIO OPTICAMENTE ACTIVO (Rh-BINAP) O COMPLEJO IRIDIO FOSFINA OPTICAMENTE ACTIVO (Ir-BINAP) Y REDUCIR CATALITICAMENTE EL PRODUCTO ANTERIOR A UNA TEMPERATURA ENTRE 40ºC Y 100ºC, pH ENTRE 3 Y 9 Y CON UN CATALIZADOR TAL COMO Pd-C, PtO2, Rh-AI2O3 O (RhCl[P(C6H5)3]3), b) CRISTALIZAR AGREGANDO EL SOLVENTE ACUOSO A LA SOLUCION DE REACCION OBTENIDA EN a). TAMBIEN ESTA REFERIDA AL CRISTAL (S)-N-[2-(1,6,7,8-TETRAHIDRO-2H-INDENO[5,4-b]FURAN-8-IL)ETIL]PROPIONAMIDA, DONDE CADA CONTENIDO DE LOS COMPUESTOS DE FORMULAS (I), (II), (III) Y (IV) ES 0,15% EN PESO O MENOS Y EL CONTENIDO TOTAL DE LOS COMPUESTOS (I) A (IV) ES 0,2% EN PESO O MENOS
PE2008001369A 2004-09-13 2005-09-09 Procedimiento para producir derivados de amina opticamente activos PE20081390A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2004265307 2004-09-13

Publications (1)

Publication Number Publication Date
PE20081390A1 true PE20081390A1 (es) 2008-10-24

Family

ID=36059992

Family Applications (3)

Application Number Title Priority Date Filing Date
PE2012001990A PE20130154A1 (es) 2004-09-13 2005-09-09 Procedimiento para producir derivados de amina opticamente activos
PE2008001369A PE20081390A1 (es) 2004-09-13 2005-09-09 Procedimiento para producir derivados de amina opticamente activos
PE2005001052A PE20060662A1 (es) 2004-09-13 2005-09-09 Procedimiento para producir derivados de amina opticamente activos

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PE2012001990A PE20130154A1 (es) 2004-09-13 2005-09-09 Procedimiento para producir derivados de amina opticamente activos

Family Applications After (1)

Application Number Title Priority Date Filing Date
PE2005001052A PE20060662A1 (es) 2004-09-13 2005-09-09 Procedimiento para producir derivados de amina opticamente activos

Country Status (32)

Country Link
US (4) US8097737B2 (es)
EP (2) EP1792899B1 (es)
JP (2) JP5127228B2 (es)
KR (1) KR101298335B1 (es)
CN (2) CN101056867B (es)
AR (1) AR050737A1 (es)
AU (1) AU2005283521B2 (es)
BR (1) BRPI0515170A (es)
CA (2) CA2579121C (es)
CR (2) CR8975A (es)
EC (1) ECSP077317A (es)
ES (1) ES2485890T3 (es)
GE (1) GEP20094725B (es)
GT (2) GT200500257A (es)
HN (1) HN2005000548A (es)
IL (2) IL181462A (es)
MA (1) MA28855B1 (es)
MX (1) MX2007002822A (es)
MY (2) MY147822A (es)
NO (1) NO20071866L (es)
NZ (1) NZ553562A (es)
PA (1) PA8645701A1 (es)
PE (3) PE20130154A1 (es)
PH (1) PH12012501172A1 (es)
RU (1) RU2385318C2 (es)
SA (1) SA05260347A (es)
SG (1) SG151330A1 (es)
TW (1) TWI400220B (es)
UA (1) UA95598C2 (es)
UY (1) UY29118A1 (es)
WO (1) WO2006030739A1 (es)
ZA (1) ZA200701724B (es)

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JP5450056B2 (ja) * 2007-03-19 2014-03-26 武田薬品工業株式会社 アリルアミン不斉水素化法
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US8084630B2 (en) 2007-05-31 2011-12-27 Teva Pharmaceutical Industries Ltd. Process for the synthesis of ramelteon and its intermediates
US20090105490A1 (en) * 2007-07-12 2009-04-23 Nurit Perlman Polymorphic forms of ramelteon and processes for preparation thereof
CN101531647B (zh) * 2008-03-13 2012-10-31 常州亚邦制药有限公司 (±)-2-(1,6,7,8-四氢-2H-茚并[5,4-b]呋喃-8-基)乙胺的拆分方法
AU2009272802A1 (en) * 2008-07-14 2010-01-21 Lek Pharmaceuticals D.D. Synthesis of 6,7-dihydro-1H-indeno[5,4-b]furan-8(2H)-one as intermediate in the preparation of ramelteon
WO2010045565A1 (en) * 2008-10-16 2010-04-22 Teva Pharmaceutical Industries Ltd. Process for the synthesis of ramelteon and its intermediates
WO2010092107A1 (en) 2009-02-12 2010-08-19 Lek Pharmaceuticals D.D. Synthesis of (s)-n-[2-(1,6,7,8-tetrahydro-2h-indeno-[5,4-b]furan-8-yl)ethyl]propionamide
CN101824012B (zh) * 2009-03-02 2011-12-07 四川大学 2-(1,6,7,8-四氢-2H-茚并-[5,4-b]呋喃-8-基)乙腈及其制备方法和用途
CA2754802A1 (en) 2009-03-10 2010-09-16 Industriale Chimica S.R.L. Process for the preparation of ramelteon
EP2243775A1 (en) 2009-04-07 2010-10-27 LEK Pharmaceuticals d.d. Synthesis of 1-(2,3-Dihydrobenzofuran-4-YL)ethanone as intermediate in the preparation of ramelteon
WO2011027323A1 (en) 2009-09-03 2011-03-10 Ranbaxy Laboratories Limited Process for the preparation of ramelteon
WO2011027319A1 (en) 2009-09-03 2011-03-10 Ranbaxy Laboratories Limited Process for the preparation of an intermediate for ramelteon
CN101648931B (zh) * 2009-09-21 2012-05-09 四川大学 一种3-(2,3-二氢苯并呋喃-5-基)-丙酸的制备方法
CN101665477B (zh) * 2009-09-21 2012-05-09 四川大学 (e)-3-(苯并呋喃-5-基)丙烯酸酯类化合物、其制备方法和用途
WO2011044990A1 (en) 2009-09-29 2011-04-21 Lonza Ltd Process for preparing 1,2,6,7-tetrahydro-8h-indeno[5,4-b]furan-8-one
WO2012035303A2 (en) 2010-09-17 2012-03-22 Cipla Limited Et Al A novel process for synthesis of ramelteon, and key intermediates for the synthesis of ramelteon
CN103664849B (zh) * 2012-08-31 2017-03-29 上海阳帆医药科技有限公司 制备2‑(1,6,7,8‑四氢‑2H‑茚并[5,4‑b]呋喃‑8‑亚基乙胺的方法
CN102924410A (zh) * 2012-10-29 2013-02-13 华润赛科药业有限责任公司 一种雷美替胺的制备方法及其中间体
CN103396387A (zh) * 2013-08-07 2013-11-20 安徽联创药物化学有限公司 雷美替胺中间体的制备方法
CN105277628B (zh) * 2014-07-07 2017-05-31 南京长澳医药科技有限公司 通过高效液相色谱法分离测定雷美替胺及其杂质的方法
CN104402848B (zh) * 2014-09-22 2017-02-08 珠海联邦制药股份有限公司 雷美替胺中的杂质化合物的制备方法及制备的标准品
CN105622557B (zh) * 2014-11-05 2018-12-04 上海医药工业研究院 雷美替胺中间体及其制备方法
KR102359229B1 (ko) 2020-04-16 2022-02-07 제이투에이치바이오텍 (주) 라멜테온의 제조 방법 및 이러한 제조 방법에 이용되는 중간체 화합물
CN115477628A (zh) * 2022-10-17 2022-12-16 江苏海悦康医药科技有限公司 一种雷美替胺二聚体的合成方法

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Also Published As

Publication number Publication date
KR101298335B1 (ko) 2013-08-20
SG151330A1 (en) 2009-04-30
GT200500257A (es) 2006-04-17
ECSP077317A (es) 2007-04-26
US20120088826A1 (en) 2012-04-12
CN102516211A (zh) 2012-06-27
JPWO2006030739A1 (ja) 2008-05-15
GEP20094725B (en) 2009-07-10
PH12012501172A1 (en) 2014-04-28
UY29118A1 (es) 2006-06-30
EP1792899B1 (en) 2014-07-09
NO20071866L (no) 2007-05-29
RU2007113811A (ru) 2008-10-20
HN2005000548A (es) 2007-04-20
IL181462A (en) 2011-12-29
AR050737A1 (es) 2006-11-15
WO2006030739A1 (ja) 2006-03-23
US20130079397A1 (en) 2013-03-28
NZ553562A (en) 2010-08-27
CA2579121A1 (en) 2006-03-23
IL181462A0 (en) 2007-07-04
KR20070054200A (ko) 2007-05-28
CA2764314C (en) 2014-06-17
CR20110698A (es) 2012-03-08
ZA200701724B (en) 2008-08-27
US8097737B2 (en) 2012-01-17
MY158073A (en) 2016-08-30
TW200613239A (en) 2006-05-01
PA8645701A1 (es) 2006-09-22
MX2007002822A (es) 2007-04-23
RU2385318C2 (ru) 2010-03-27
US8609871B2 (en) 2013-12-17
CN101056867A (zh) 2007-10-17
EP1792899A4 (en) 2009-12-16
US20090036521A1 (en) 2009-02-05
PE20130154A1 (es) 2013-02-27
MY147822A (en) 2013-01-31
ES2485890T3 (es) 2014-08-14
TWI400220B (zh) 2013-07-01
GT200500257AA (es) 2008-07-28
SA05260347A (ar) 2005-12-03
US20140066499A1 (en) 2014-03-06
AU2005283521A1 (en) 2006-03-23
EP1792899A1 (en) 2007-06-06
CN101056867B (zh) 2011-12-07
JP5615304B2 (ja) 2014-10-29
MA28855B1 (fr) 2007-09-03
JP5127228B2 (ja) 2013-01-23
PE20060662A1 (es) 2006-08-22
UA95598C2 (ru) 2011-08-25
CA2764314A1 (en) 2006-03-23
CA2579121C (en) 2013-07-30
IL207510A (en) 2013-02-28
BRPI0515170A (pt) 2008-07-08
AU2005283521B2 (en) 2011-10-13
EP2537842A1 (en) 2012-12-26
JP2012116848A (ja) 2012-06-21
CR8975A (es) 2007-08-28

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