JP5198067B2 - ４−ヒドロキシベンゾモルファン - Google Patents

４−ヒドロキシベンゾモルファン Download PDF

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Publication number
JP5198067B2
JP5198067B2 JP2007540055A JP2007540055A JP5198067B2 JP 5198067 B2 JP5198067 B2 JP 5198067B2 JP 2007540055 A JP2007540055 A JP 2007540055A JP 2007540055 A JP2007540055 A JP 2007540055A JP 5198067 B2 JP5198067 B2 JP 5198067B2
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group
mmol
acid
hydroxy
cdcl
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JP2008519035A5 (enExample
JP2008519035A (ja
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マーク ピー． ヴェントランド
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レンセラール ポリテクニック インスティチュート
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    • 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
    • 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
    • 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

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  • 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)
JP2007540055A 2004-11-05 2005-11-03 ４−ヒドロキシベンゾモルファン Expired - Lifetime JP5198067B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US62534804P 2004-11-05 2004-11-05
US60/625,348 2004-11-05
PCT/US2005/039911 WO2006052710A1 (en) 2004-11-05 2005-11-03 4-hydroxybenzomorphans

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP2012256445A Division JP6058981B2 (ja) 2004-11-05 2012-11-22 ４−ヒドロキシベンゾモルファン

Publications (3)

Publication Number Publication Date
JP2008519035A JP2008519035A (ja) 2008-06-05
JP2008519035A5 JP2008519035A5 (enExample) 2008-11-13
JP5198067B2 true JP5198067B2 (ja) 2013-05-15

Family

ID=36128632

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Application Number Title Priority Date Filing Date
JP2007540055A Expired - Lifetime JP5198067B2 (ja) 2004-11-05 2005-11-03 ４−ヒドロキシベンゾモルファン
JP2012256445A Expired - Lifetime JP6058981B2 (ja) 2004-11-05 2012-11-22 ４−ヒドロキシベンゾモルファン
JP2015159733A Pending JP2016020364A (ja) 2004-11-05 2015-08-12 ４−ヒドロキシベンゾモルファン

Family Applications After (2)

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JP2012256445A Expired - Lifetime JP6058981B2 (ja) 2004-11-05 2012-11-22 ４−ヒドロキシベンゾモルファン
JP2015159733A Pending JP2016020364A (ja) 2004-11-05 2015-08-12 ４−ヒドロキシベンゾモルファン

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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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

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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
JP2008519035A (ja) 2008-06-05
US20130231361A1 (en) 2013-09-05
ATE557006T1 (de) 2012-05-15
CN101090891A (zh) 2007-12-19
AU2005304950B2 (en) 2010-12-09

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