ATE557006T1 - 4-hydroxybenzomorphane - Google Patents

4-hydroxybenzomorphane

Info

Publication number
ATE557006T1
ATE557006T1 AT10008474T AT10008474T ATE557006T1 AT E557006 T1 ATE557006 T1 AT E557006T1 AT 10008474 T AT10008474 T AT 10008474T AT 10008474 T AT10008474 T AT 10008474T AT E557006 T1 ATE557006 T1 AT E557006T1
Authority
AT
Austria
Prior art keywords
hydroxybenzomorphanes
hydroxybenzomorphans
thiocarboxamide
antitussives
anticonvulsants
Prior art date
Application number
AT10008474T
Other languages
German (de)
English (en)
Inventor
Mark P Wentland
Original Assignee
Rensselaer Polytech Inst
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 Rensselaer Polytech Inst filed Critical Rensselaer Polytech Inst
Application granted granted Critical
Publication of ATE557006T1 publication Critical patent/ATE557006T1/de

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
    • C07D221/28—Morphinans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
    • C07D221/26—Benzomorphans
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/485—Morphinan derivatives, e.g. morphine, codeine
    • 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
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • A61P1/12—Antidiarrhoeals
    • 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
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/14—Antitussive agents
    • 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
    • A61P17/04—Antipruritics
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36—Opioid-abuse
    • 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
    • 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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • C07D489/06—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with a hetero atom directly attached in position 14
    • C07D489/08—Oxygen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Addiction (AREA)
  • Immunology (AREA)
  • Emergency Medicine (AREA)
  • Psychiatry (AREA)
  • Epidemiology (AREA)
  • Pulmonology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Transplantation (AREA)
  • Obesity (AREA)
  • Dermatology (AREA)
  • Hematology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Rheumatology (AREA)
  • Diabetes (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
AT10008474T 2004-11-05 2005-11-03 4-hydroxybenzomorphane ATE557006T1 (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US62534804P 2004-11-05 2004-11-05

Publications (1)

Publication Number Publication Date
ATE557006T1 true ATE557006T1 (de) 2012-05-15

Family

ID=36128632

Family Applications (1)

Application Number Title Priority Date Filing Date
AT10008474T ATE557006T1 (de) 2004-11-05 2005-11-03 4-hydroxybenzomorphane

Country Status (20)

Country Link
US (7) US7262298B2 (enExample)
EP (2) EP1817291A1 (enExample)
JP (3) JP5198067B2 (enExample)
KR (1) KR101115841B1 (enExample)
CN (1) CN101090891B (enExample)
AT (1) ATE557006T1 (enExample)
AU (1) AU2005304950B2 (enExample)
BR (1) BRPI0517091B8 (enExample)
CA (1) CA2587074C (enExample)
CY (1) CY1112946T1 (enExample)
DK (1) DK2251330T3 (enExample)
ES (1) ES2387737T3 (enExample)
IL (1) IL182983A (enExample)
MX (1) MX2007005389A (enExample)
NO (1) NO340204B1 (enExample)
PL (1) PL2251330T3 (enExample)
PT (1) PT2251330E (enExample)
RU (2) RU2480455C2 (enExample)
SI (1) SI2251330T1 (enExample)
WO (1) WO2006052710A1 (enExample)

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CA2426942C (en) * 2000-10-31 2014-06-03 Mark P. Wentland 8-carboxamido-2,6-methano-3-benzazocines
PT2251330E (pt) * 2004-11-05 2012-07-20 Rensselaer Polytech Inst 4-hidroxibenzomorfanos
EP2266959B1 (en) 2005-07-21 2013-05-01 Rensselaer Polytechnic Institute 8-carboxamido-substituted-2, 6-methano-3-benzazocines and 3-carboxamido-substituted morphanes as opioid receptor binding agents
AU2008207580B2 (en) 2007-05-04 2011-04-14 SpecGx LLC Improved process for the preparation of 6-alpha-hydroxy-N-alkylated opiates
EP2167505B1 (en) 2007-07-17 2012-11-28 Mallinckrodt LLC Preparation of n-alkylated opiates by reductive amination
EP2190819B1 (en) 2007-08-09 2016-05-25 Rensselaer Polytechnic Institute Quaternary opioid carboxamides
WO2010039222A2 (en) 2008-09-30 2010-04-08 Mallinckrodt Inc. Processes for the selective amination of ketomorphinans
US8946419B2 (en) 2009-02-23 2015-02-03 Mallinckrodt Llc (+)-6-hydroxy-morphinan or (+)-6-amino-morphinan derivatives
EP3170395A1 (en) * 2009-03-19 2017-05-24 Alkermes Pharma Ireland Limited Morphinan derivatives with high oral bioavailability
WO2010118274A1 (en) * 2009-04-09 2010-10-14 Mallinckrodt Inc. Preparation of 6-keto, 3-alkoxy morphinans
JP5680069B2 (ja) 2009-06-11 2015-03-04 マリンクロッド エルエルシー 触媒的水素移動による６−ケトノルモルフィナンの還元アミノ化
EP2440562B1 (en) 2009-06-11 2016-08-10 Mallinckrodt LLC Preparation of 6-alpha-amino n-substituted morphinans by catalytic hydrogen transfer
NZ600379A (en) * 2009-12-04 2014-05-30 Alkermes Pharma Ireland Ltd Morphinan derivatives for the treatment of drug overdose
US8436175B2 (en) * 2010-03-22 2013-05-07 Rensselaer Polytechnic Institute Carboxamide bioisosteres of opiates
EP2563793B1 (en) * 2010-04-29 2014-10-22 Mallinckrodt LLC Preparation of saturated ketone morphinan compounds having low metal content
WO2012005795A1 (en) 2010-07-08 2012-01-12 Alkermes, Inc. Process for the synthesis of substituted morphinans
SI3446565T1 (sl) 2010-08-23 2024-03-29 Alkermes Pharma Ireland Limited Metode zdravljenja povečanja teže, povzročene z antipsihotiki
WO2012138888A1 (en) 2011-04-05 2012-10-11 Alkermes, Inc. Process for the synthesis of quaternary amine compounds
RU2013157298A (ru) 2011-06-09 2015-07-20 МАЛЛИНКРОДТ Эл-Эл-Си Восстановительное аминирование 6-кетоморфинанов посредством каталитического переноса водорода
RS56181B1 (sr) 2011-06-29 2017-11-30 Alkermes Inc Periferno delujuća opioidna jedinjenja
JP2014526467A (ja) 2011-09-08 2014-10-06 マリンクロッド エルエルシー 中間体の単離なしでのアルカロイドの調製
HUE041883T2 (hu) 2011-12-15 2019-06-28 Alkermes Pharma Ireland Ltd Samidorphan (ALKS 33) és buprenorfin kombináció, depressziós zavarok kezelésére
US9211293B2 (en) 2011-12-15 2015-12-15 Alkermes Pharma Ireland Limited Opioid agonist antagonist combinations
US9656961B2 (en) 2013-05-24 2017-05-23 Alkermes Pharma Ireland Limited Methods for treating depressive symptoms
JP2016519161A (ja) 2013-05-24 2016-06-30 アルカームス ファーマ アイルランド リミテッド モルファン及びモルフィナン類似物及び使用の方法
CA3054122A1 (en) * 2017-03-02 2018-09-07 Sanwa Kagaku Kenkyusho Co., Ltd. Therapeutic agent for alcohol use disorders
CN107089948B (zh) * 2017-04-28 2020-07-17 云南大学 吗吩衍生物及其制备方法和应用
CN111978252A (zh) * 2019-05-21 2020-11-24 复旦大学 手性苯并吗吩烷类衍生物及其制备方法和在药学上的应用
CN113248435B (zh) * 2020-02-13 2024-06-04 上海翰森生物医药科技有限公司 3-甲酰胺基-4-羟基纳曲酮氘代衍生物、其制备方法及其在医药上的应用
CN111205151B (zh) * 2020-02-29 2021-03-05 深圳市祥根生物科技有限公司 一种布洛芬杂质i的环保制备方法
EP4243768A1 (en) 2020-11-12 2023-09-20 Alkermes Pharma Ireland Limited Immediate release multilayer tablet
CN114621238A (zh) * 2020-12-10 2022-06-14 鲁南制药集团股份有限公司 一种制备纳呋拉啡的方法
KR102663533B1 (ko) * 2021-11-09 2024-05-08 백미선 레이저 치료기기용 온냉각장치

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US4032529A (en) 1974-09-20 1977-06-28 Sterling Drug Inc. Aminomethanobenzazocine intermediates
SU635868A3 (ru) * 1974-11-12 1978-11-30 Бристол Мейерз Компани (Фирма) Способ получени морфиновых производных или их солей
US4205171A (en) 1976-01-12 1980-05-27 Sterling Drug Inc. Aminomethanobenzazocines and nitromethanobenzazocines
US4373139A (en) 1979-04-30 1983-02-08 Motorola, Inc. Detectors
US4649200A (en) 1986-05-08 1987-03-10 Regents Of The University Of Minnesota Substituted pyrroles with opioid receptor activity
EP0632041A1 (en) 1993-07-01 1995-01-04 Katholieke Universiteit Nijmegen New morphine derivatives having improved analgesic and narcotic properties
AU706370B2 (en) 1996-01-10 1999-06-17 Smithkline Beecham Spa Heterocycle-condensed morphinoid derivatives (II)
CA2426942C (en) 2000-10-31 2014-06-03 Mark P. Wentland 8-carboxamido-2,6-methano-3-benzazocines
AU2003281060A1 (en) 2002-07-16 2004-02-02 Rensselaer Polytechnic Institute Process for conversion of phenols to carboxamides via the succinimide esters
PT2251330E (pt) * 2004-11-05 2012-07-20 Rensselaer Polytech Inst 4-hidroxibenzomorfanos

Also Published As

Publication number Publication date
KR101115841B1 (ko) 2012-03-09
WO2006052710A1 (en) 2006-05-18
EP2251330B1 (en) 2012-05-09
US20240092740A1 (en) 2024-03-21
JP6058981B2 (ja) 2017-01-11
ES2387737T3 (es) 2012-10-01
US8680112B2 (en) 2014-03-25
SI2251330T1 (sl) 2012-09-28
DK2251330T3 (da) 2012-08-06
US7262298B2 (en) 2007-08-28
BRPI0517091B8 (pt) 2021-05-25
NO340204B1 (no) 2017-03-20
BRPI0517091B1 (pt) 2019-10-08
IL182983A0 (en) 2007-08-19
CY1112946T1 (el) 2016-04-13
RU2480455C2 (ru) 2013-04-27
CA2587074A1 (en) 2006-05-18
US20160075658A1 (en) 2016-03-17
EP2251330A1 (en) 2010-11-17
US20060111384A1 (en) 2006-05-25
RU2010147915A (ru) 2012-05-27
KR20070085723A (ko) 2007-08-27
RU2415131C2 (ru) 2011-03-27
US20070238748A1 (en) 2007-10-11
JP2016020364A (ja) 2016-02-04
RU2007120759A (ru) 2008-12-10
BRPI0517091A (pt) 2008-09-30
NO20072839L (no) 2007-08-03
US8802655B2 (en) 2014-08-12
CA2587074C (en) 2012-09-04
MX2007005389A (es) 2007-12-07
JP2013067636A (ja) 2013-04-18
IL182983A (en) 2012-06-28
PT2251330E (pt) 2012-07-20
US20150011768A1 (en) 2015-01-08
AU2005304950A1 (en) 2006-05-18
PL2251330T3 (pl) 2012-12-31
EP1817291A1 (en) 2007-08-15
CN101090891B (zh) 2012-08-01
US20140148475A1 (en) 2014-05-29
JP5198067B2 (ja) 2013-05-15
JP2008519035A (ja) 2008-06-05
US20130231361A1 (en) 2013-09-05
CN101090891A (zh) 2007-12-19
AU2005304950B2 (en) 2010-12-09

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