BRPI0515998A - compostos heterocìclicos adequados para tratar desordens que respondem à modulação do receptor d3 de dopamina - Google Patents

compostos heterocìclicos adequados para tratar desordens que respondem à modulação do receptor d3 de dopamina

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Publication number
BRPI0515998A
BRPI0515998A BRPI0515998-9A BRPI0515998A BRPI0515998A BR PI0515998 A BRPI0515998 A BR PI0515998A BR PI0515998 A BRPI0515998 A BR PI0515998A BR PI0515998 A BRPI0515998 A BR PI0515998A
Authority
BR
Brazil
Prior art keywords
alkyl
fluorinated
cycloalkyl
dopamine
alkylcarbonyl
Prior art date
Application number
BRPI0515998-9A
Other languages
English (en)
Inventor
Karla Drescher
Andreas Haupt
Liliane Unger
Sean C Turner
Wilfried Braje
Roland Grandel
Christophe Henry
Gisela Backfisch
Armin Beyerbach
Wilfried Lubisch
Original Assignee
Abbott Gmbh & Co Kg
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
Application filed by Abbott Gmbh & Co Kg filed Critical Abbott Gmbh & Co Kg
Publication of BRPI0515998A publication Critical patent/BRPI0515998A/pt

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • 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
    • A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
    • 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
    • A61P25/14—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
    • A61P25/24—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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • C07D211/28—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biomedical Technology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrrole Compounds (AREA)

Abstract

COMPOSTOS HETEROCìCLICOS ADEQUADOS PARA TRATAR DESORDENS QUE RESPONDEM à MODULAçãO DO RECEPTOR D~ 1~ DE DOPAMINA. A invenção diz respeito a compostos da fórmula (I) em que n é 0, 1 ou 2; G é CH~ 2~ ou CHR ; R¬ 1¬ é H, alquila-C~ 1~-C~ 6~, alquila-C~ 1~-C~ 6~ substituído por cicloalquila-C~ 3~-C~ 6~, hidroxialquila-C~ 1~-C~ 6~, alquila-C~ 1~-C~ 6~ fluorado, cicloalquila-C~ 3~-C~ 6~, cicloalquila-C~ 3~-C~ 6~ fluorado, alquenila-C~ 3~-C~ 6~, alquenila-C~ 3~-C~ 6~ fluorado, formila, acetila ou propionila; R¬ 2¬, R¬ 3¬ e R¬ 4¬ são, independentemente um do outro, H, metila, fluormetila, difluormetila, ou trifluormetila; A é fenileno, piridileno, pirimidileno, pirazinileno, piridazinileno ou tiofenileno, que pode ser substituído por um ou mais substituintes selecionados de halogênio, metila, metóxi e CF~ 3~; E NR¬ 5¬ ou CH~ 2~,em que R¬ 5¬ é H ou C~ 1~ -C~ 3~-alquila; Ar é um radical cíclico selecionado do grupo que consiste em fenila, um radical heteroaromático de 5 ou 6 membros compreendendo como membros do anel, 1, ou 3 heteroátomos selecionados de N, O e S e um anel fenila fundido a um anel carbocíclico ou heterocíclico de 5 ou 6 membros saturado ou insaturado, onde o anel heterocíclico compreende como membros do anel, 1, 2 ou 3 heteroátomos selecionados de N, O e S e/ou 1, 2 ou 3 heteroátomos contendo grupos cada qual independentemente selecionados de NR¬ 8¬, onde R¬ 8¬ é H, alquila-C~ 1~-C~ 4~, alquila-C~ 1~-C~ 4~ fluorado, alquilcarbonila-C~ 1~-C~ 4~ ou alquilcarbonila-C~ 1~-C~ 4~ fluorado e onde o radical cíclico Ar pode carregar 1, 2 ou 3 substituintes R¬ a¬, em que o R¬ a¬ variável tem o significado dado nas reivindicações e na descrição; e sais de adição ácida fisiologicamente tolerados destes. A invenção diz respeito ao uso de um composto de fórmula I ou um sal farmaceuticamente aceitável deste para preparar uma composição farmacêutica para o tratamento de uma desordem médica suscetível ao tratamento com um ligante do receptor D~ 3~ de dopamina.
BRPI0515998-9A 2004-10-14 2005-10-14 compostos heterocìclicos adequados para tratar desordens que respondem à modulação do receptor d3 de dopamina BRPI0515998A (pt)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US61887804P 2004-10-14 2004-10-14
PCT/EP2005/011106 WO2006040182A1 (en) 2004-10-14 2005-10-14 Heterocyclic compounds suitable for treating disorders that respond to modulation of the dopamine d3 receptor

Publications (1)

Publication Number Publication Date
BRPI0515998A true BRPI0515998A (pt) 2008-08-19

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ID=35744845

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BRPI0515998-9A BRPI0515998A (pt) 2004-10-14 2005-10-14 compostos heterocìclicos adequados para tratar desordens que respondem à modulação do receptor d3 de dopamina

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Country Link
US (2) US7851463B2 (pt)
EP (3) EP2311803A1 (pt)
JP (1) JP4904277B2 (pt)
KR (1) KR101315192B1 (pt)
CN (1) CN101039904B (pt)
AT (1) ATE504566T1 (pt)
AU (1) AU2005293698B2 (pt)
BR (1) BRPI0515998A (pt)
CA (1) CA2583983C (pt)
DE (1) DE602005027382D1 (pt)
ES (1) ES2364488T3 (pt)
HK (1) HK1111681A1 (pt)
IL (1) IL182431A (pt)
MX (1) MX2007004359A (pt)
NZ (1) NZ555123A (pt)
TW (1) TWI364414B (pt)
WO (1) WO2006040182A1 (pt)
ZA (1) ZA200703061B (pt)

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US20040204422A1 (en) * 2003-04-14 2004-10-14 Abbott Gmbh & Co. Kg. N-[(Piperazinyl)hetaryl]arylsulfonamide compounds
WO2006040182A1 (en) * 2004-10-14 2006-04-20 Abbott Gmbh & Co. Kg Heterocyclic compounds suitable for treating disorders that respond to modulation of the dopamine d3 receptor
EP1922068A4 (en) * 2005-08-16 2010-08-11 Icagen Inc INHIBITORS OF VOLTAGE-CONTROLLED SODIUM CHANNELS
US8642642B2 (en) * 2006-04-19 2014-02-04 Abbott Laboratories Heterocyclic arylsulphones suitable for treating disorders that respond to modulation of the serotonin 5HT6 receptor
CA2648892A1 (en) 2006-04-19 2007-10-25 Abbott Gmbh & Co. Kg Heterocyclic compounds suitable for treating disorders that respond to modulation of the serotonin 5ht6 receptor
DE102007036068A1 (de) 2007-08-01 2009-02-05 Wacker Chemie Ag Verfahren zur Herstellung von Alkyl-methoxymethyl-trimethylsilanylmethylaminen
DE102008022221A1 (de) 2008-05-06 2009-11-12 Universität des Saarlandes Inhibitoren der humanen Aldosteronsynthase CYP11B2
US8541404B2 (en) 2009-11-09 2013-09-24 Elexopharm Gmbh Inhibitors of the human aldosterone synthase CYP11B2
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EP3233799B1 (en) 2014-12-19 2021-05-19 The Broad Institute, Inc. Dopamine d2 receptor ligands
CN109503449A (zh) * 2018-12-17 2019-03-22 天津药明康德新药开发有限公司 一种3-硝基吖丁啶-1-甲酸叔丁酯的合成方法
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WO2023249875A1 (en) * 2022-06-21 2023-12-28 Alkermes, Inc. Substituted pyrrolidinyl and piperidinyl compounds and related methods of treatment

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US8642642B2 (en) * 2006-04-19 2014-02-04 Abbott Laboratories Heterocyclic arylsulphones suitable for treating disorders that respond to modulation of the serotonin 5HT6 receptor

Also Published As

Publication number Publication date
US20080045493A1 (en) 2008-02-21
EP1814849A1 (en) 2007-08-08
WO2006040182A1 (en) 2006-04-20
US20110160176A1 (en) 2011-06-30
HK1111681A1 (en) 2008-08-15
ES2364488T3 (es) 2011-09-05
AU2005293698A1 (en) 2006-04-20
CN101039904A (zh) 2007-09-19
CA2583983A1 (en) 2006-04-20
JP2008516918A (ja) 2008-05-22
TW200619195A (en) 2006-06-16
IL182431A (en) 2012-04-30
US8470810B2 (en) 2013-06-25
AU2005293698B2 (en) 2011-12-15
US7851463B2 (en) 2010-12-14
ZA200703061B (en) 2008-09-25
CA2583983C (en) 2013-07-16
CN101039904B (zh) 2014-09-24
ATE504566T1 (de) 2011-04-15
EP2311802A1 (en) 2011-04-20
TWI364414B (en) 2012-05-21
JP4904277B2 (ja) 2012-03-28
NZ555123A (en) 2011-01-28
IL182431A0 (en) 2007-07-24
KR101315192B1 (ko) 2013-10-10
EP2311803A1 (en) 2011-04-20
MX2007004359A (es) 2007-07-17
EP1814849B1 (en) 2011-04-06
KR20070084208A (ko) 2007-08-24
DE602005027382D1 (de) 2011-05-19

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