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
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)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Immunology (AREA)
  • Addiction (AREA)
  • Pulmonology (AREA)
  • Emergency Medicine (AREA)
  • Epidemiology (AREA)
  • Psychiatry (AREA)
  • Obesity (AREA)
  • Child & Adolescent Psychology (AREA)
  • Rheumatology (AREA)
  • Diabetes (AREA)
  • Dermatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Hematology (AREA)
  • Transplantation (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)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Hydrogenated Pyridines (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 (de)
EP (2) EP1817291A1 (de)
JP (3) JP5198067B2 (de)
KR (1) KR101115841B1 (de)
CN (1) CN101090891B (de)
AT (1) ATE557006T1 (de)
AU (1) AU2005304950B2 (de)
BR (1) BRPI0517091B8 (de)
CA (1) CA2587074C (de)
CY (1) CY1112946T1 (de)
DK (1) DK2251330T3 (de)
ES (1) ES2387737T3 (de)
IL (1) IL182983A (de)
MX (1) MX2007005389A (de)
NO (1) NO340204B1 (de)
PL (1) PL2251330T3 (de)
PT (1) PT2251330E (de)
RU (2) RU2415131C2 (de)
SI (1) SI2251330T1 (de)
WO (1) WO2006052710A1 (de)

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DE60109960T2 (de) * 2000-10-31 2006-02-16 Rensselaer Polytechnic Institute 8-substituierte 2,6-methano-3-benzazocine und 3-substituierte morphinane als opioidrezeptorbindende agenzien
CA2587074C (en) * 2004-11-05 2012-09-04 Rensselaer Polytechnic Institute 4-hydroxybenzomorphans
CA2615774C (en) 2005-07-21 2014-12-09 Rensselaer Polytechnic Institute Large substituent, non-phenolic opioids
ES2407033T3 (es) 2007-05-04 2013-06-11 Mallinckrodt Llc Procedimientos mejorados para la preparación de opiáceos 6-alfa-hidroxi-n-alquilados
NZ582668A (en) 2007-07-17 2012-02-24 Mallinckrodt Llc Preparation of n-alkylated opiates by reductive amination
KR101519682B1 (ko) 2007-08-09 2015-05-19 렌슬러 폴리테크닉 인스티튜트 4급 오피오이드 카르복스아미드
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
JP5555890B2 (ja) * 2009-03-19 2014-07-23 アルカーメス ファーマ アイルランド リミテッド 高い経口バイオアベイラビリティを有するモルフィナン誘導体
WO2010118274A1 (en) * 2009-04-09 2010-10-14 Mallinckrodt Inc. Preparation of 6-keto, 3-alkoxy morphinans
EP2440561B1 (de) 2009-06-11 2014-04-30 Mallinckrodt LLC Reduktive aminierung von 6-keto-normorphinanen durch katalytischen wasserstofftransfer
WO2010144641A1 (en) 2009-06-11 2010-12-16 Mallinckrodt Inc. Preparation of 6-alpha-amino n-substituted morphinans by catalytic hydrogen transfer
RS58894B1 (sr) 2009-12-04 2019-08-30 Alkermes Pharma Ireland Ltd Derivati morfinana za lečenje predoziranja lekom
EP2550253B9 (de) 2010-03-22 2016-09-21 Rensselaer Polytechnic Institute Carboxamid-bioisostere von opiaten
AU2011245437B2 (en) * 2010-04-29 2014-10-02 SpecGx 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
HUE041981T2 (hu) 2010-08-23 2019-06-28 Alkermes Pharma Ireland Ltd Eljárások antipszichotikum által kiváltott súlygyarapodás kezelésére
US9029543B2 (en) 2011-04-05 2015-05-12 Alkermes, Inc. Process for the synthesis of quaternary amine compounds
MX2013013634A (es) 2011-06-09 2013-12-12 Mallinckrodt Llc Aminacion reductiva de 6-ceto-morfinanos por transfrencia catalitica de hidrogeno.
JP5981992B2 (ja) 2011-06-29 2016-08-31 アルカーメス，インコーポレイテッド 末梢作用オピオイド化合物
ES2566620T3 (es) 2011-09-08 2016-04-14 Mallinckrodt Llc Procesamiento de alcaloides sin el aislamiento de intermedios
US9211293B2 (en) 2011-12-15 2015-12-15 Alkermes Pharma Ireland Limited Opioid agonist antagonist combinations
MX2014007042A (es) 2011-12-15 2015-01-22 Alkermes Pharma Ireland Ltd Composiciones de la buprenorfina y antagonistas de los receptores opioide-mu.
US9656961B2 (en) 2013-05-24 2017-05-23 Alkermes Pharma Ireland Limited Methods for treating depressive symptoms
AU2014268361B2 (en) 2013-05-24 2018-09-06 Alkermes Pharma Ireland Limited Morphan and morphinan analogues, and methods of use
US20200237720A1 (en) * 2017-03-02 2020-07-30 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
WO2022101444A1 (en) 2020-11-12 2022-05-19 Alkermes Pharma Ireland Limited Immediate release multilayer tablet
KR102663533B1 (ko) * 2021-11-09 2024-05-08 백미선 레이저 치료기기용 온냉각장치

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US3957793A (en) * 1974-09-20 1976-05-18 Sterling Drug Inc. Hydroxyiminobenzazocines
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US4649200A (en) * 1986-05-08 1987-03-10 Regents Of The University Of Minnesota Substituted pyrroles with opioid receptor activity
EP0632041A1 (de) 1993-07-01 1995-01-04 Katholieke Universiteit Nijmegen Neue Morphin Derivate mit verbesserten analgetischen und narkotischen Eigenschaften
WO1997025331A1 (en) 1996-01-10 1997-07-17 Smithkline Beecham S.P.A. Heterocycle-condensed morphinoid derivatives (ii)
DE60109960T2 (de) * 2000-10-31 2006-02-16 Rensselaer Polytechnic Institute 8-substituierte 2,6-methano-3-benzazocine und 3-substituierte morphinane als opioidrezeptorbindende agenzien
WO2004007449A1 (en) 2002-07-16 2004-01-22 Rensselaer Polytechnic Institute Process for conversion of phenols to carboxamides via the succinimide esters
CA2587074C (en) * 2004-11-05 2012-09-04 Rensselaer Polytechnic Institute 4-hydroxybenzomorphans

Also Published As

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

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ES1052088Y (es) Mastil para banderines.