CA2793526C - Naphthofuran compounds and compositions for targeting cancer stem cells - Google Patents

Naphthofuran compounds and compositions for targeting cancer stem cells Download PDF

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Publication number
CA2793526C
CA2793526C CA2793526A CA2793526A CA2793526C CA 2793526 C CA2793526 C CA 2793526C CA 2793526 A CA2793526 A CA 2793526A CA 2793526 A CA2793526 A CA 2793526A CA 2793526 C CA2793526 C CA 2793526C
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CA
Canada
Prior art keywords
cancer
compound
polymorph
furan
degrees
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Fee Related
Application number
CA2793526A
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English (en)
French (fr)
Other versions
CA2793526A1 (en
Inventor
Chiang Jia Li
David Leggett
Youzhi Li
Wei Li
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Pharma Oncology Inc
Original Assignee
Boston Biomedical Inc
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 Boston Biomedical Inc filed Critical Boston Biomedical Inc
Priority to CA2946890A priority Critical patent/CA2946890A1/en
Priority to CA2959951A priority patent/CA2959951A1/en
Priority to CA2959931A priority patent/CA2959931A1/en
Priority to CA2946899A priority patent/CA2946899C/en
Publication of CA2793526A1 publication Critical patent/CA2793526A1/en
Application granted granted Critical
Publication of CA2793526C publication Critical patent/CA2793526C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/92—Naphthofurans; Hydrogenated naphthofurans
    • 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
    • A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
    • 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
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • 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
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/14—Drugs for genital or sexual disorders; Contraceptives for lactation disorders, e.g. galactorrhoea
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (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)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Immunology (AREA)
  • Emergency Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Rheumatology (AREA)
  • Oncology (AREA)
  • Cardiology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Pregnancy & Childbirth (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Diabetes (AREA)
  • Vascular Medicine (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Pulmonology (AREA)
  • Dermatology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
CA2793526A 2010-03-19 2011-03-21 Naphthofuran compounds and compositions for targeting cancer stem cells Expired - Fee Related CA2793526C (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA2946890A CA2946890A1 (en) 2010-03-19 2011-03-21 Naphthofuran compounds and compositions for targeting cancer stem cells
CA2959951A CA2959951A1 (en) 2010-03-19 2011-03-21 Naphthofuran compounds and compositions for targeting cancer stem cells
CA2959931A CA2959931A1 (en) 2010-03-19 2011-03-21 Naphthofuran compounds and compositions for targeting cancer stem cells
CA2946899A CA2946899C (en) 2010-03-19 2011-03-21 Naphthofuran compounds and compositions for targeting cancer stem cells

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US31588610P 2010-03-19 2010-03-19
US31589010P 2010-03-19 2010-03-19
US61/315,890 2010-03-19
US61/315,886 2010-03-19
US32581410P 2010-04-19 2010-04-19
US61/325,814 2010-04-19
PCT/US2011/029281 WO2011116398A1 (en) 2010-03-19 2011-03-21 Novel compounds and compositions for targeting cancer stem cells

Related Child Applications (4)

Application Number Title Priority Date Filing Date
CA2959931A Division CA2959931A1 (en) 2010-03-19 2011-03-21 Naphthofuran compounds and compositions for targeting cancer stem cells
CA2946899A Division CA2946899C (en) 2010-03-19 2011-03-21 Naphthofuran compounds and compositions for targeting cancer stem cells
CA2959951A Division CA2959951A1 (en) 2010-03-19 2011-03-21 Naphthofuran compounds and compositions for targeting cancer stem cells
CA2946890A Division CA2946890A1 (en) 2010-03-19 2011-03-21 Naphthofuran compounds and compositions for targeting cancer stem cells

Publications (2)

Publication Number Publication Date
CA2793526A1 CA2793526A1 (en) 2011-09-22
CA2793526C true CA2793526C (en) 2018-05-01

Family

ID=47678419

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2793526A Expired - Fee Related CA2793526C (en) 2010-03-19 2011-03-21 Naphthofuran compounds and compositions for targeting cancer stem cells
CA2946899A Expired - Fee Related CA2946899C (en) 2010-03-19 2011-03-21 Naphthofuran compounds and compositions for targeting cancer stem cells

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2946899A Expired - Fee Related CA2946899C (en) 2010-03-19 2011-03-21 Naphthofuran compounds and compositions for targeting cancer stem cells

Country Status (15)

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US (4) US9084766B2 (enExample)
EP (1) EP2547334B1 (enExample)
JP (1) JP5602935B2 (enExample)
KR (2) KR101908208B1 (enExample)
CN (3) CN107375260B (enExample)
AU (2) AU2011227022C1 (enExample)
BR (2) BR112012023661A2 (enExample)
CA (2) CA2793526C (enExample)
DK (1) DK2547334T3 (enExample)
ES (1) ES2659541T3 (enExample)
MX (2) MX370721B (enExample)
NZ (1) NZ602328A (enExample)
RU (1) RU2571661C2 (enExample)
SG (1) SG184063A1 (enExample)
WO (1) WO2011116398A1 (enExample)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2190429B1 (en) 2007-09-10 2016-04-20 Boston Biomedical, Inc. A novel group of stat3 pathway inhibitors and cancer stem cell pathway inhibitors
NZ602328A (en) * 2010-03-19 2014-11-28 Boston Biomedical Inc Novel compounds and compositions for targeting cancer stem cells
CN104016951B (zh) * 2010-03-19 2016-07-13 北京强新生物科技有限公司 靶向癌症干细胞的化合物和组合物
US20160030384A1 (en) * 2013-04-09 2016-02-04 Boston Biomedical, Inc. 2-acetylnaphtho[2,3-b]furan -4,9-dione for use on treating cancer
CN106163284A (zh) * 2014-02-07 2016-11-23 北京强新生物科技有限公司 3‑取代的羰基萘并[2,3‑b]呋喃衍生物或其药学上可接受的盐
EP3153508B1 (en) 2014-06-09 2020-03-18 Kyoto Pharmaceutical Industries, Ltd. Naphthofuran derivatives for use as anticancer agents
WO2016168857A1 (en) 2015-04-17 2016-10-20 Boston Biomedical, Inc. Methods for treating cancer
JP2018511643A (ja) 2015-04-17 2018-04-26 ボストン バイオメディカル, インコーポレイテッド 癌を治療するための方法
WO2016196935A1 (en) * 2015-06-03 2016-12-08 Boston Biomedical, Inc. Compositions comprising a cancer stemness inhibitor and an immunotherapeutic agent for use in treating cancer
US10329267B2 (en) 2015-07-17 2019-06-25 Sumitomo Dainippon Pharma Co., Ltd. Method for producing 2-acetyl-4H,9H-naphtho[2,3-b]furan-4,9-dione
WO2017079864A1 (en) * 2015-11-12 2017-05-18 Hangzhou Yier Biotech Co., Ltd. Treatment of cancers related to chronically active ras
WO2017132049A1 (en) 2016-01-20 2017-08-03 Boston Biomedical, Inc. Methods for treating cancer
WO2017160978A1 (en) 2016-03-15 2017-09-21 Boston Biomedical, Inc. Cell cultures and use thereof
WO2018005444A2 (en) 2016-06-28 2018-01-04 Boston Biomedical, Inc. Methods for treating cancer
WO2018098352A2 (en) 2016-11-22 2018-05-31 Jun Oishi Targeting kras induced immune checkpoint expression
CA3045306A1 (en) 2016-11-29 2018-06-07 Boston Biomedical, Inc. Naphthofuran derivatives, preparation, and methods of use thereof
JP2020512377A (ja) 2017-03-30 2020-04-23 ボストン バイオメディカル, インコーポレイテッド がんを処置および/または防止するための組成物
JP2020520923A (ja) 2017-05-17 2020-07-16 ボストン バイオメディカル, インコーポレイテッド がんを処置するための方法
MX2021004151A (es) 2018-10-12 2021-09-08 1Globe Biomedical Co Ltd Nueva solución de combinación para el tratamiento contra cáncer refractario a la quimioterapia.

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1049490A1 (ru) * 1982-05-18 1983-10-23 Ордена Трудового Красного Знамени Институт Химии Ан Мсср (3 @ ,9 @ ,9 @ )-6,6,9 @ -Триметилтранспергидронафто(2,1- @ )фуран,в качестве душистого компонента парфюмерной композиции
JPH1121284A (ja) 1997-06-30 1999-01-26 Kotobuki:Kk フラノナフトキノン誘導体及びこれを含有する医薬
WO2004026253A2 (en) * 2002-09-17 2004-04-01 Arqule, Inc. Novel lapacho compounds and methods of use thereof
US20070238770A1 (en) * 2006-04-05 2007-10-11 Bristol-Myers Squibb Company Process for preparing novel crystalline forms of peliglitazar, novel stable forms produced therein and formulations
EP2190429B1 (en) * 2007-09-10 2016-04-20 Boston Biomedical, Inc. A novel group of stat3 pathway inhibitors and cancer stem cell pathway inhibitors
WO2009060282A2 (en) * 2007-11-06 2009-05-14 Orchid Research Laboratories Limited Stilbene derivatives as pstat3/il-6 inhibitors
NZ602328A (en) * 2010-03-19 2014-11-28 Boston Biomedical Inc Novel compounds and compositions for targeting cancer stem cells

Also Published As

Publication number Publication date
CA2946899A1 (en) 2011-09-22
US20130034591A1 (en) 2013-02-07
KR101714819B1 (ko) 2017-03-09
CN107375260A (zh) 2017-11-24
RU2012144421A (ru) 2014-04-27
SG184063A1 (en) 2012-10-30
AU2016200953A1 (en) 2016-03-03
CA2793526A1 (en) 2011-09-22
ES2659541T3 (es) 2018-03-16
KR101908208B1 (ko) 2018-10-15
WO2011116398A1 (en) 2011-09-22
CN107721958A (zh) 2018-02-23
AU2011227022C1 (en) 2016-04-21
US20150183756A1 (en) 2015-07-02
CN103002890A (zh) 2013-03-27
US20180193303A1 (en) 2018-07-12
CN107375260B (zh) 2023-10-24
JP5602935B2 (ja) 2014-10-08
MX370721B (es) 2019-12-20
DK2547334T3 (en) 2018-02-19
BR112012023661A2 (pt) 2020-11-24
AU2011227022B2 (en) 2015-11-19
MX394137B (es) 2025-03-24
BR122021025776B1 (pt) 2022-12-27
AU2016200953B2 (en) 2017-07-27
KR20130056227A (ko) 2013-05-29
RU2571661C2 (ru) 2015-12-20
NZ602328A (en) 2014-11-28
MX2012010434A (es) 2013-01-29
EP2547334B1 (en) 2017-11-15
EP2547334A1 (en) 2013-01-23
US9084766B2 (en) 2015-07-21
JP2013522325A (ja) 2013-06-13
US9381184B2 (en) 2016-07-05
KR20160135375A (ko) 2016-11-25
AU2011227022A1 (en) 2012-09-27
CA2946899C (en) 2018-03-06
US20160271099A1 (en) 2016-09-22
EP2547334A4 (en) 2013-08-14
CN107721958B (zh) 2024-08-23

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