BRPI0809023B8 - derivados de pleuromutilina, seus usos, e composições farmacêuticas - Google Patents

derivados de pleuromutilina, seus usos, e composições farmacêuticas

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Publication number
BRPI0809023B8
BRPI0809023B8 BRPI0809023A BRPI0809023A BRPI0809023B8 BR PI0809023 B8 BRPI0809023 B8 BR PI0809023B8 BR PI0809023 A BRPI0809023 A BR PI0809023A BR PI0809023 A BRPI0809023 A BR PI0809023A BR PI0809023 B8 BRPI0809023 B8 BR PI0809023B8
Authority
BR
Brazil
Prior art keywords
alkyl
pharmaceutical compositions
cycloalkyl
pleuromutilin derivatives
proviso
Prior art date
Application number
BRPI0809023A
Other languages
English (en)
Inventor
Rama Chandra Murty Bulusu Atchyuta
Strickmann Dirk
Ferencic Mathias
Novak Rodger
Mang Rosemarie
Badegruber Rudolf
Heilmayer Werner
Original Assignee
Nabriva Therapeutics Ag
Nabriva Therapeutics GmbH
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=38668870&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=BRPI0809023(B8) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Nabriva Therapeutics Ag, Nabriva Therapeutics GmbH filed Critical Nabriva Therapeutics Ag
Publication of BRPI0809023A2 publication Critical patent/BRPI0809023A2/pt
Publication of BRPI0809023B1 publication Critical patent/BRPI0809023B1/pt
Publication of BRPI0809023B8 publication Critical patent/BRPI0809023B8/pt

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, 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
    • C07C323/51—Thiols, 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
    • C07C323/57—Thiols, 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
    • C07C323/58—Thiols, 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
    • 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
    • A61K31/535—Heterocyclic 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
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/221—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having an amino group, e.g. acetylcholine, acetylcarnitine
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic 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
    • 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
    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A61P31/06—Antibacterial agents for tuberculosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, 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
    • C07C323/51—Thiols, 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
    • C07C323/52—Thiols, 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, 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
    • C07C323/61—Thiols, 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic 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
    • C07D295/04—Heterocyclic 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
    • C07D295/08—Heterocyclic 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
    • C07D295/096—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/93—Spiro compounds
    • C07C2603/95—Spiro compounds containing "not free" spiro atoms
    • C07C2603/98—Spiro compounds containing "not free" spiro atoms containing at least one ring with more than six ring members
    • C07C2603/99—Spiro 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)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Emergency Medicine (AREA)
  • Communicable Diseases (AREA)
  • Oncology (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)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Hydrogenated Pyridines (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Peptides Or Proteins (AREA)

Abstract

derivados de pleuromutilina, composições farmacêuticas compreendendo os mesmos e seus usos. a presente invenção refere-se a um composto da fórmula (i) em que n é 0 a 4; m é 0 ou 1 com a condição de que o átomo de enxofre e r3 estejam na posição vicinal (se m = 0 então r3 está na posição 2, e se m = 1 então r3 está na posição 1); r é etila ou vinila; r1 é hidrogênio ou (c1-8) alquila, r2 é hidrogênio ou - (c3-6) cicloalquila, ou - (c1-6) alquila não-substituída, ou - (c1-6) alquila substituída por um ou mais de - hidróxi; de preferência um ou dois, - metóxi, - halogênio, - (c3-6) cicloaquila ou r1 e r2 juntamente com o átomo de nitrogênio ao qual eles estão ligados formam um anel heterocíclico de 5 a 7 membros contendo pelo menos 1 átomo de nitrogênio ou 1 nitrogênio e 1 heteroátomo adicional por exemplo, selecionado de n ou o, ou r1 é hidróxi e r2 é formila; r3 é oh, or4, um átomo de halogênio, ou - com a condição de que r3 esteja ligado a 2 r3 representa -o-(ch2)- com p é 2 ou 3; r4 é (c1-6) alquila ou (c3-6) cicloalquila não-substituída.
BRPI0809023A 2007-03-20 2008-03-19 derivados de pleuromutilina, seus usos, e composições farmacêuticas BRPI0809023B8 (pt)

Applications Claiming Priority (3)

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
EP07450053.9 2007-03-20
PCT/AT2008/000097 WO2008113089A1 (en) 2007-03-20 2008-03-19 Pleuromutilin derivatives for the treatment of diseases mediated by microbes

Publications (3)

Publication Number Publication Date
BRPI0809023A2 BRPI0809023A2 (pt) 2014-09-23
BRPI0809023B1 BRPI0809023B1 (pt) 2020-12-01
BRPI0809023B8 true BRPI0809023B8 (pt) 2021-05-25

Family

ID=38668870

Family Applications (1)

Application Number Title Priority Date Filing Date
BRPI0809023A BRPI0809023B8 (pt) 2007-03-20 2008-03-19 derivados de pleuromutilina, seus usos, e composições farmacêuticas

Country Status (31)

Country Link
US (12) US20090118366A1 (pt)
EP (3) EP1972618A1 (pt)
JP (2) JP5479114B2 (pt)
KR (1) KR101478593B1 (pt)
CN (2) CN104211624B (pt)
AT (1) ATE523486T1 (pt)
AU (1) AU2008229609B2 (pt)
BR (1) BRPI0809023B8 (pt)
CA (1) CA2678795C (pt)
CY (2) CY1117482T1 (pt)
DK (2) DK2137143T3 (pt)
EA (1) EA018707B1 (pt)
ES (2) ES2375503T3 (pt)
FI (1) FIC20200038I1 (pt)
HR (1) HRP20110869T1 (pt)
HU (1) HUS2100001I1 (pt)
IL (1) IL200440A (pt)
LT (1) LTC2137143I2 (pt)
MA (1) MA31314B1 (pt)
MY (1) MY148916A (pt)
NL (1) NL301086I2 (pt)
NO (1) NO2021002I1 (pt)
NZ (1) NZ579011A (pt)
PL (1) PL2137143T3 (pt)
PT (2) PT2380874T (pt)
SI (1) SI2137143T1 (pt)
TN (1) TN2009000347A1 (pt)
TW (1) TWI406657B (pt)
UA (1) UA97836C2 (pt)
WO (1) WO2008113089A1 (pt)
ZA (1) ZA200905590B (pt)

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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
KR102656841B1 (ko) * 2015-06-17 2024-04-12 나브리바 테라퓨틱스 게엠베하 레파뮬린의 주사가능한 약제학적 제형
RS57328B1 (sr) 2015-06-18 2018-08-31 Mithra Pharmaceuticals S A Orodisperzibilna dozna jedinica koja sadrži estetrolsku komponentu
NZ737945A (en) 2015-06-18 2023-06-30 Estetra Sprl 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
CR20200486A (es) 2018-04-19 2021-01-27 Estetra Sprl Compuestos y sus usos para aliviar los síntomas asociados a la menopausa
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
TWI893101B (zh) 2020-04-16 2025-08-11 比利時商埃斯特拉有限責任公司 具有降低之副作用之避孕組成物
JP2023522644A (ja) * 2020-04-17 2023-05-31 ナブリバ セラピューティクス ゲーエムベーハー プレウロムチリンの治療的使用
EP4135681B1 (en) 2020-04-17 2025-06-25 Nabriva Therapeutics GMBH Antiviral use of pleuromutilins
ES3056228T3 (en) 2020-04-17 2026-02-19 Ariva Med Gmbh Antiviral use of pleuromutilins
EP4475834A1 (en) 2022-02-09 2024-12-18 Nabriva Therapeutics GMBH Lefamulin and its derivatives for use in the treatment of a spiral shaped bacteria
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EA200970868A1 (ru) 2010-02-26
US20130040954A1 (en) 2013-02-14
CN101668738B (zh) 2014-10-15
CA2678795C (en) 2014-11-18
ES2620459T3 (es) 2017-06-28
JP5479114B2 (ja) 2014-04-23
US20220218713A1 (en) 2022-07-14
TWI406657B (zh) 2013-09-01
ES2375503T3 (es) 2012-03-01
ATE523486T1 (de) 2011-09-15
HRP20110869T1 (hr) 2011-12-31
WO2008113089A1 (en) 2008-09-25
EP2137143A1 (en) 2009-12-30
EP2137143B1 (en) 2011-09-07
HK1140185A1 (en) 2010-10-08
CY2020032I1 (el) 2020-11-25
TW200904402A (en) 2009-02-01
US20210113571A1 (en) 2021-04-22
SI2137143T1 (sl) 2012-01-31
UA97836C2 (ru) 2012-03-26
CY1117482T1 (el) 2017-04-26
HUS2100001I1 (hu) 2021-03-01
LTC2137143I2 (lt) 2023-10-10
AU2008229609B2 (en) 2012-03-29
PL2137143T3 (pl) 2012-02-29
BRPI0809023A2 (pt) 2014-09-23
KR101478593B1 (ko) 2015-01-02
NO2021002I1 (no) 2021-01-15
CN101668738A (zh) 2010-03-10
DK2137143T3 (da) 2012-01-02
DK2380874T3 (en) 2017-03-27
AU2008229609A1 (en) 2008-09-25
LTPA2020531I1 (lt) 2020-11-10
US20100035987A1 (en) 2010-02-11
CY2020032I2 (el) 2020-11-25
EP1972618A1 (en) 2008-09-24
JP2014159416A (ja) 2014-09-04
US20170266194A1 (en) 2017-09-21
US20190175603A1 (en) 2019-06-13
EP2380874B1 (en) 2016-12-28
US20200030335A1 (en) 2020-01-30
US20140256731A1 (en) 2014-09-11
PT2380874T (pt) 2017-04-03
CN104211624B (zh) 2017-12-15
TN2009000347A1 (fr) 2010-12-31
MA31314B1 (fr) 2010-04-01
BRPI0809023B1 (pt) 2020-12-01
US20090118366A1 (en) 2009-05-07
CN104211624A (zh) 2014-12-17
JP5893651B2 (ja) 2016-03-23
CA2678795A1 (en) 2008-09-25
IL200440A0 (en) 2010-04-29
NZ579011A (en) 2011-03-31
PT2137143E (pt) 2011-12-22
IL200440A (en) 2013-09-30
ZA200905590B (en) 2010-10-27
US20120029072A1 (en) 2012-02-02
NL301086I2 (nl) 2021-01-28
EP2380874A2 (en) 2011-10-26
KR20090123882A (ko) 2009-12-02
MY148916A (en) 2013-06-14
FIC20200038I1 (fi) 2020-10-01
US8071643B2 (en) 2011-12-06
EP2380874A3 (en) 2011-12-07
US20180303842A1 (en) 2018-10-25
US8153689B2 (en) 2012-04-10
EA018707B1 (ru) 2013-10-30
JP2010522143A (ja) 2010-07-01
US20200281933A1 (en) 2020-09-10

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