EA200970868A1 - Производные плевромутилина для лечения заболеваний, опосредуемых микробами - Google Patents

Производные плевромутилина для лечения заболеваний, опосредуемых микробами

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Publication number
EA200970868A1
EA200970868A1 EA200970868A EA200970868A EA200970868A1 EA 200970868 A1 EA200970868 A1 EA 200970868A1 EA 200970868 A EA200970868 A EA 200970868A EA 200970868 A EA200970868 A EA 200970868A EA 200970868 A1 EA200970868 A1 EA 200970868A1
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EA
Eurasian Patent Office
Prior art keywords
atom
alkyl
pleurromutilin
microbes
derivatives
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EA200970868A
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English (en)
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EA018707B1 (ru
Inventor
Роземари Манг
Вернер Хайльмайер
Рудольф Бадегрубер
Дирк Штрикманн
Родгер Новак
Матиас Ференцик
Атхиута Рама Хандра Мурти Булюзу
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Набрива Терапьютикс Аг
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=38668870&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EA200970868(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Набрива Терапьютикс Аг filed Critical Набрива Терапьютикс Аг
Publication of EA200970868A1 publication Critical patent/EA200970868A1/ru
Publication of EA018707B1 publication Critical patent/EA018707B1/ru

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/53751,4-Oxazines, e.g. morpholine
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/21Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/21Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/221Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having an amino group, e.g. acetylcholine, acetylcarnitine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/335Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/10Anti-acne agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • A61P31/06Antibacterial agents for tuberculosis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/61Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D317/00Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/93Spiro compounds
    • C07C2603/95Spiro compounds containing "not free" spiro atoms
    • C07C2603/98Spiro compounds containing "not free" spiro atoms containing at least one ring with more than six ring members
    • C07C2603/99Spiro compounds containing "not free" spiro atoms containing at least one ring with more than six ring members containing eight-membered rings

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Hydrogenated Pyridines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Peptides Or Proteins (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Соединение формулы (I), где n равно числу от 0 до 4; m равно 0 или 1, при условии, что атом серы и Rнаходятся в вицинальном положении (если m=0, тогда Rнаходится в положении 2', а если m=1, тогда Rнаходится в положении 1'); R представляет этил или винил; Rпредставляет атом водорода или (Cалкил; Rпредставляет атом водорода или -(С)циклоалкил, или незамещенный (C)алкил, или (C)алкил, замещенный одной или несколькими группами из числа таких, как гидрокси, предпочтительно одна или две, метокси, атом галогена, (С)циклоалкил, или Rи Rвместе с атомом азота, к которому они присоединены, образуют 5-7-членное гетероциклическое кольцо, содержащее по меньшей мере 1 атом азота или 1 атом азота и 1 дополнительный гетероатом, например, выбранный из N или О, или Rпредставляет гидрокси и Rпредставляет формил; Rпредставляет ОН, OR, атом галогена, или, при условии, что Rприсоединен в положении 2', Rпредставляет -O-(СН)-O- с р равным 2 или 3; Rпредставляет незамещенный (C)алкил или (С)циклоалкил.
EA200970868A 2007-03-20 2008-03-19 Производные плевромутилина для лечения заболеваний, опосредуемых микробами EA018707B1 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP07450053A EP1972618A1 (en) 2007-03-20 2007-03-20 Pleuromutilin derivatives for the treatment of diseases mediated by microbes
PCT/AT2008/000097 WO2008113089A1 (en) 2007-03-20 2008-03-19 Pleuromutilin derivatives for the treatment of diseases mediated by microbes

Publications (2)

Publication Number Publication Date
EA200970868A1 true EA200970868A1 (ru) 2010-02-26
EA018707B1 EA018707B1 (ru) 2013-10-30

Family

ID=38668870

Family Applications (1)

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EA200970868A EA018707B1 (ru) 2007-03-20 2008-03-19 Производные плевромутилина для лечения заболеваний, опосредуемых микробами

Country Status (32)

Country Link
US (12) US20090118366A1 (ru)
EP (3) EP1972618A1 (ru)
JP (2) JP5479114B2 (ru)
KR (1) KR101478593B1 (ru)
CN (2) CN101668738B (ru)
AT (1) ATE523486T1 (ru)
AU (1) AU2008229609B2 (ru)
BR (1) BRPI0809023B8 (ru)
CA (1) CA2678795C (ru)
CY (2) CY1117482T1 (ru)
DK (2) DK2137143T3 (ru)
EA (1) EA018707B1 (ru)
ES (2) ES2620459T3 (ru)
FI (1) FIC20200038I1 (ru)
HK (1) HK1140185A1 (ru)
HR (1) HRP20110869T1 (ru)
HU (1) HUS2100001I1 (ru)
IL (1) IL200440A (ru)
LT (1) LTPA2020531I1 (ru)
MA (1) MA31314B1 (ru)
MY (1) MY148916A (ru)
NL (1) NL301086I2 (ru)
NO (1) NO2021002I1 (ru)
NZ (1) NZ579011A (ru)
PL (1) PL2137143T3 (ru)
PT (2) PT2380874T (ru)
SI (1) SI2137143T1 (ru)
TN (1) TN2009000347A1 (ru)
TW (1) TWI406657B (ru)
UA (1) UA97836C2 (ru)
WO (1) WO2008113089A1 (ru)
ZA (1) ZA200905590B (ru)

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EP1808431A1 (en) * 2006-01-16 2007-07-18 Nabriva Therapeutics Forschungs GmbH Mutilin derivatives and their use as pharmaceutical
EP1972618A1 (en) 2007-03-20 2008-09-24 Nabriva Therapeutics AG Pleuromutilin derivatives for the treatment of diseases mediated by microbes
EP2159220A1 (en) * 2008-09-02 2010-03-03 Nabriva Therapeutics AG Organic compounds
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EP2399904A1 (en) 2010-05-26 2011-12-28 Nabriva Therapeutics AG Process for the preparation of pleuromutilins
EP2390245A1 (en) * 2010-05-26 2011-11-30 Nabriva Therapeutics AG Enantiomerically pure amines
EP2433926A1 (en) 2010-09-09 2012-03-28 Nabriva Therapeutics AG Pleuromutilin derivatives for use in the treatment of diseases mediated by microbes
JP5906314B2 (ja) 2011-07-15 2016-04-20 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH 2,3−ジフェニル−バレロニトリル誘導体、それらを製造する方法並びに除草剤及び植物成長調節剤としてのそれらの使用
CN103265487A (zh) * 2013-06-05 2013-08-28 北京理工大学 截短侧耳素扩环衍生物及其制备方法和用途
CN104803911B (zh) * 2014-01-23 2018-01-05 中国科学院上海药物研究所 一类截短侧耳素化合物、其药物组合物、合成方法与用途
ES2553929B1 (es) * 2014-06-11 2016-09-26 Antonio Javier MORENO CASTRO Dispositivo de modificación/destrucción selectiva de tejidos orgánicos
UA121240C2 (uk) * 2015-06-17 2020-04-27 Набріва Терапютикс Гмбх Ін'єкційна фармацевтична композиція лефамуліну
CN116077455A (zh) 2015-06-18 2023-05-09 埃斯特拉有限责任公司 含雌四醇组分的口腔分散剂量单位
CA2988498C (en) 2015-06-18 2022-02-08 Mithra Pharmaceuticals S.A. Orodispersible dosage unit containing an estetrol component
TWI762573B (zh) 2017-02-10 2022-05-01 奧地利商納畢瓦治療有限責任公司 截短側耳素之純化
TWI801561B (zh) 2018-04-19 2023-05-11 比利時商依思特拉私人有限責任公司 化合物及其用於緩解絕經相關症狀的用途
JOP20200260A1 (ar) 2018-04-19 2019-10-19 Estetra Sprl مركبات واستخداماتها للتخفيف من الأعراض المصاحبة لانقطاع الطمث
CN111170911A (zh) * 2019-09-29 2020-05-19 安帝康(无锡)生物科技有限公司 用于治疗细菌感染性疾病的截短侧耳素类化合物
CN111170893B (zh) * 2020-01-19 2022-04-26 郑州依米花手性药物研究有限公司 Lefamulin的中间体化合物及其在Lefamulin制备中的应用
BR112022020007A2 (pt) 2020-04-17 2022-11-22 Nabriva Therapeutics GmbH Uso terapêutico de pleuromutilinas
WO2021209173A1 (en) 2020-04-17 2021-10-21 Nabriva Therapeutics GmbH Novel therapeutic use of pleuromutilins
CN115413238A (zh) 2020-04-17 2022-11-29 纳布里瓦治疗有限责任公司 截短侧耳素类化合物的治疗用途
WO2023152115A1 (en) 2022-02-09 2023-08-17 Nabriva Therapeutics GmbH Lefamulin and its derivatives for use in the treatment of a spiral shaped bacteria
EP4338732A1 (en) 2022-09-16 2024-03-20 Nabriva Therapeutics GMBH Lefamulin and its derivatives for use in the treatment of tularemia

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EP1972618A1 (en) 2007-03-20 2008-09-24 Nabriva Therapeutics AG Pleuromutilin derivatives for the treatment of diseases mediated by microbes

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ES2620459T3 (es) 2017-06-28
US20100035987A1 (en) 2010-02-11
US20140256731A1 (en) 2014-09-11
CN101668738B (zh) 2014-10-15
IL200440A (en) 2013-09-30
PT2137143E (pt) 2011-12-22
PL2137143T3 (pl) 2012-02-29
MA31314B1 (fr) 2010-04-01
JP2014159416A (ja) 2014-09-04
CN104211624B (zh) 2017-12-15
DK2137143T3 (da) 2012-01-02
EP2137143B1 (en) 2011-09-07
US8153689B2 (en) 2012-04-10
US8071643B2 (en) 2011-12-06
UA97836C2 (ru) 2012-03-26
EP2380874A3 (en) 2011-12-07
AU2008229609A1 (en) 2008-09-25
US20200281933A1 (en) 2020-09-10
CN104211624A (zh) 2014-12-17
FIC20200038I1 (fi) 2020-10-01
TN2009000347A1 (fr) 2010-12-31
US20090118366A1 (en) 2009-05-07
TW200904402A (en) 2009-02-01
CY2020032I1 (el) 2020-11-25
US20180303842A1 (en) 2018-10-25
SI2137143T1 (sl) 2012-01-31
US20200030335A1 (en) 2020-01-30
EP2137143A1 (en) 2009-12-30
BRPI0809023B1 (pt) 2020-12-01
EP1972618A1 (en) 2008-09-24
TWI406657B (zh) 2013-09-01
MY148916A (en) 2013-06-14
BRPI0809023B8 (pt) 2021-05-25
US20170266194A1 (en) 2017-09-21
EP2380874A2 (en) 2011-10-26
WO2008113089A1 (en) 2008-09-25
US20120029072A1 (en) 2012-02-02
NO2021002I1 (no) 2021-01-15
CN101668738A (zh) 2010-03-10
CY1117482T1 (el) 2017-04-26
US20220218713A1 (en) 2022-07-14
NZ579011A (en) 2011-03-31
EP2380874B1 (en) 2016-12-28
US20190175603A1 (en) 2019-06-13
LTPA2020531I1 (lt) 2020-11-10
DK2380874T3 (en) 2017-03-27
PT2380874T (pt) 2017-04-03
US20210113571A1 (en) 2021-04-22
KR101478593B1 (ko) 2015-01-02
JP5893651B2 (ja) 2016-03-23
CY2020032I2 (el) 2020-11-25
KR20090123882A (ko) 2009-12-02
HK1140185A1 (en) 2010-10-08
EA018707B1 (ru) 2013-10-30
US20130040954A1 (en) 2013-02-14
HUS2100001I1 (hu) 2021-03-01
CA2678795A1 (en) 2008-09-25
JP2010522143A (ja) 2010-07-01
ES2375503T3 (es) 2012-03-01
JP5479114B2 (ja) 2014-04-23
NL301086I2 (nl) 2021-01-28
AU2008229609B2 (en) 2012-03-29
IL200440A0 (en) 2010-04-29
BRPI0809023A2 (pt) 2014-09-23
HRP20110869T1 (hr) 2011-12-31
ATE523486T1 (de) 2011-09-15
ZA200905590B (en) 2010-10-27
CA2678795C (en) 2014-11-18

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