BRPI0517091B8 - composto 4-hidroxibenzomorfano substituído na posição-3 por carboxamida ou tiocarboxamida - Google Patents

composto 4-hidroxibenzomorfano substituído na posição-3 por carboxamida ou tiocarboxamida

Info

Publication number
BRPI0517091B8
BRPI0517091B8 BRPI0517091A BRPI0517091A BRPI0517091B8 BR PI0517091 B8 BRPI0517091 B8 BR PI0517091B8 BR PI0517091 A BRPI0517091 A BR PI0517091A BR PI0517091 A BRPI0517091 A BR PI0517091A BR PI0517091 B8 BRPI0517091 B8 BR PI0517091B8
Authority
BR
Brazil
Prior art keywords
thiocarboxamide
compound
carboxamide
hydroxybenzomorphan
substituted
Prior art date
Application number
BRPI0517091A
Other languages
English (en)
Portuguese (pt)
Inventor
P Wentland Mark
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
Publication of BRPI0517091A publication Critical patent/BRPI0517091A/pt
Publication of BRPI0517091B1 publication Critical patent/BRPI0517091B1/pt
Publication of BRPI0517091B8 publication Critical patent/BRPI0517091B8/pt

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
    • 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
    • C07D221/26—Benzomorphans
    • 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)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Addiction (AREA)
  • Immunology (AREA)
  • Pulmonology (AREA)
  • Psychiatry (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Obesity (AREA)
  • Transplantation (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Hydrogenated Pyridines (AREA)
BRPI0517091A 2004-11-05 2005-11-03 composto 4-hidroxibenzomorfano substituído na posição-3 por carboxamida ou tiocarboxamida BRPI0517091B8 (pt)

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

Publications (3)

Publication Number Publication Date
BRPI0517091A BRPI0517091A (pt) 2008-09-30
BRPI0517091B1 BRPI0517091B1 (pt) 2019-10-08
BRPI0517091B8 true BRPI0517091B8 (pt) 2021-05-25

Family

ID=36128632

Family Applications (1)

Application Number Title Priority Date Filing Date
BRPI0517091A BRPI0517091B8 (pt) 2004-11-05 2005-11-03 composto 4-hidroxibenzomorfano substituído na posição-3 por carboxamida ou tiocarboxamida

Country Status (20)

Country Link
US (7) US7262298B2 (cg-RX-API-DMAC10.html)
EP (2) EP2251330B1 (cg-RX-API-DMAC10.html)
JP (3) JP5198067B2 (cg-RX-API-DMAC10.html)
KR (1) KR101115841B1 (cg-RX-API-DMAC10.html)
CN (1) CN101090891B (cg-RX-API-DMAC10.html)
AT (1) ATE557006T1 (cg-RX-API-DMAC10.html)
AU (1) AU2005304950B2 (cg-RX-API-DMAC10.html)
BR (1) BRPI0517091B8 (cg-RX-API-DMAC10.html)
CA (1) CA2587074C (cg-RX-API-DMAC10.html)
CY (1) CY1112946T1 (cg-RX-API-DMAC10.html)
DK (1) DK2251330T3 (cg-RX-API-DMAC10.html)
ES (1) ES2387737T3 (cg-RX-API-DMAC10.html)
IL (1) IL182983A (cg-RX-API-DMAC10.html)
MX (1) MX2007005389A (cg-RX-API-DMAC10.html)
NO (1) NO340204B1 (cg-RX-API-DMAC10.html)
PL (1) PL2251330T3 (cg-RX-API-DMAC10.html)
PT (1) PT2251330E (cg-RX-API-DMAC10.html)
RU (2) RU2415131C2 (cg-RX-API-DMAC10.html)
SI (1) SI2251330T1 (cg-RX-API-DMAC10.html)
WO (1) WO2006052710A1 (cg-RX-API-DMAC10.html)

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US7262298B2 (en) * 2004-11-05 2007-08-28 Rensselaer Polytechnic Institute 4-hydroxybenzomorphans
AU2006272773B2 (en) 2005-07-21 2012-03-08 Rensselaer Polytechnic Institute 8-carboxamido-substituted-2 , 6-methano-3-benzazocines and 3 - carboxamido- substituted morphanes as opioid receptor binding agents
ATE493416T1 (de) 2007-05-04 2011-01-15 Mallinckrodt Inc Verbessertes verfahren zur herstellung von 6- alpha-hydroxy-n-alkylierten opiaten
JP2010533719A (ja) 2007-07-17 2010-10-28 マリンクロッド・インコーポレイテッド 還元的アミノ化によるn−アルキル化オピエートの調製
WO2009023567A1 (en) 2007-08-09 2009-02-19 Rensselaer Polytechnic Institute Quaternary opioid carboxamides
CA2738628C (en) 2008-09-30 2017-07-04 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
WO2010107457A1 (en) * 2009-03-19 2010-09-23 Alkermes, Inc. Morphinan derivatives with high oral bioavailability
WO2010118274A1 (en) * 2009-04-09 2010-10-14 Mallinckrodt Inc. Preparation of 6-keto, 3-alkoxy morphinans
US8471023B2 (en) 2009-06-11 2013-06-25 Mallinckrodt Llc Reductive amination of 6-keto normorphinans by catalytic hydrogen transfer
CA2764915C (en) 2009-06-11 2017-07-11 Mallinckrodt Llc Preparation of 6-alpha-amino n-substituted morphinans by catalytic hydrogen transfer
HUE043963T2 (hu) * 2009-12-04 2019-09-30 Alkermes Pharma Ireland Ltd Morfinán származékok gyógyszer-túladagolás kezelésére
WO2011119605A2 (en) 2010-03-22 2011-09-29 Rensselaer Polytechnic Institute Carboxamide biosiosteres of opiates
WO2011137086A1 (en) * 2010-04-29 2011-11-03 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
EP2608670B1 (en) 2010-08-23 2018-10-31 Alkermes Pharma Ireland Limited Methods for treating antipsychotic-induced weight gain
US9029543B2 (en) 2011-04-05 2015-05-12 Alkermes, Inc. Process for the synthesis of quaternary amine compounds
ES2698408T3 (es) 2011-06-09 2019-02-04 SpecGx LLC Aminación reductora de 6-ceto morfinanos por transferencia de hidrógeno catalítico
CA2840643C (en) 2011-06-29 2017-11-21 Alkermes, Inc. Peripherally acting opioid compounds
KR20140063763A (ko) 2011-09-08 2014-05-27 말린크로트 엘엘씨 중간체를 단리하지 않는 알칼로이드의 제조 방법
SMT201800664T1 (it) 2011-12-15 2019-01-11 Alkermes Pharma Ireland Ltd Samidorphan (alks 33) in combinazione con buprenorfina per il trattamento di disturbi depressivi
US9211293B2 (en) 2011-12-15 2015-12-15 Alkermes Pharma Ireland Limited Opioid agonist antagonist combinations
ES2770978T3 (es) 2013-05-24 2020-07-06 Alkermes Pharma Ireland Ltd Análogos de morfanos y morfinanos y métodos de uso
US9656961B2 (en) 2013-05-24 2017-05-23 Alkermes Pharma Ireland Limited Methods for treating depressive symptoms
KR20190120212A (ko) * 2017-03-02 2019-10-23 가부시키가이샤산와카가쿠켄큐쇼 알코올 사용 장해의 치료약
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
TW202140009A (zh) * 2020-02-13 2021-11-01 大陸商上海翰森生物醫藥科技有限公司 3-甲醯胺基-4-羥基納曲酮氘代衍生物、其製備方法及其在醫藥上的應用
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
WO2022101444A1 (en) 2020-11-12 2022-05-19 Alkermes Pharma Ireland Limited Immediate release multilayer tablet
CN114621238B (zh) * 2020-12-10 2026-02-03 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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Also Published As

Publication number Publication date
ATE557006T1 (de) 2012-05-15
DK2251330T3 (da) 2012-08-06
EP2251330B1 (en) 2012-05-09
RU2480455C2 (ru) 2013-04-27
AU2005304950A1 (en) 2006-05-18
EP2251330A1 (en) 2010-11-17
IL182983A0 (en) 2007-08-19
CY1112946T1 (el) 2016-04-13
ES2387737T3 (es) 2012-10-01
BRPI0517091A (pt) 2008-09-30
JP6058981B2 (ja) 2017-01-11
NO20072839L (no) 2007-08-03
CA2587074C (en) 2012-09-04
US20240092740A1 (en) 2024-03-21
US7262298B2 (en) 2007-08-28
RU2415131C2 (ru) 2011-03-27
US20140148475A1 (en) 2014-05-29
WO2006052710A1 (en) 2006-05-18
US20150011768A1 (en) 2015-01-08
CA2587074A1 (en) 2006-05-18
MX2007005389A (es) 2007-12-07
CN101090891B (zh) 2012-08-01
US20070238748A1 (en) 2007-10-11
US20060111384A1 (en) 2006-05-25
RU2010147915A (ru) 2012-05-27
CN101090891A (zh) 2007-12-19
NO340204B1 (no) 2017-03-20
BRPI0517091B1 (pt) 2019-10-08
KR20070085723A (ko) 2007-08-27
AU2005304950B2 (en) 2010-12-09
US8680112B2 (en) 2014-03-25
SI2251330T1 (sl) 2012-09-28
JP2013067636A (ja) 2013-04-18
IL182983A (en) 2012-06-28
JP2016020364A (ja) 2016-02-04
PT2251330E (pt) 2012-07-20
US20160075658A1 (en) 2016-03-17
JP5198067B2 (ja) 2013-05-15
US8802655B2 (en) 2014-08-12
US20130231361A1 (en) 2013-09-05
KR101115841B1 (ko) 2012-03-09
JP2008519035A (ja) 2008-06-05
RU2007120759A (ru) 2008-12-10
PL2251330T3 (pl) 2012-12-31
EP1817291A1 (en) 2007-08-15

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