CY1123670T1 - Κρυσταλλικο παραγωγο 6,7-ακορεστης-7-καρβαμοϋλ μορφινανης, και μεθοδος για την παραγωγη αυτου - Google Patents

Κρυσταλλικο παραγωγο 6,7-ακορεστης-7-καρβαμοϋλ μορφινανης, και μεθοδος για την παραγωγη αυτου

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Publication number
CY1123670T1
CY1123670T1 CY20191101018T CY191101018T CY1123670T1 CY 1123670 T1 CY1123670 T1 CY 1123670T1 CY 20191101018 T CY20191101018 T CY 20191101018T CY 191101018 T CY191101018 T CY 191101018T CY 1123670 T1 CY1123670 T1 CY 1123670T1
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CY
Cyprus
Prior art keywords
unsaturated
carbamoyl
morpfinane
production
crystalline derivative
Prior art date
Application number
CY20191101018T
Other languages
English (en)
Inventor
Yoshinori Tamura
Kouichi Noguchi
Masanao Inagaki
Kenji Morimoto
Nobuhiro Haga
Shinichi Oda
Sohei Omura
Original Assignee
Shionogi & Co., Ltd.
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 Shionogi & Co., Ltd. filed Critical Shionogi & Co., Ltd.
Publication of CY1123670T1 publication Critical patent/CY1123670T1/el

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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D489/00Heterocyclic 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:
    • C07D489/06Heterocyclic 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
    • C07D489/08Oxygen atom
    • 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
    • A61K31/435Heterocyclic 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
    • A61K31/47Quinolines; Isoquinolines
    • A61K31/485Morphinan derivatives, e.g. morphine, codeine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/14Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605Excipients; Inactive ingredients
    • A61K9/1629Organic macromolecular compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/10Laxatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/14Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/04Centrally acting analgesics, e.g. opioids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32Alcohol-abuse
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A61P29/02Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/02Nutrients, e.g. vitamins, minerals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00General protective or antinoxious agents
    • A61P39/02Antidotes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/06Antianaemics
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06Halogens; Compounds thereof
    • B01J27/08Halides
    • B01J27/10Chlorides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01Sulfonic acids
    • C07C309/28Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/29Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
    • C07C309/30Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
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    • C07C51/412Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07D271/061,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
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    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13Crystalline forms, e.g. polymorphs
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Nutrition Science (AREA)
  • Hematology (AREA)
  • Addiction (AREA)
  • Emergency Medicine (AREA)
  • Diabetes (AREA)
  • Rheumatology (AREA)
  • Toxicology (AREA)
  • Hospice & Palliative Care (AREA)
  • Otolaryngology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Psychiatry (AREA)
  • Obesity (AREA)
  • Materials Engineering (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Σταθερές κρυσταλλικές μορφές μιας ένωσης που αντιπροσωπεύεται από τον τύπο (ΙΑ): ένα άλας προσθήκης οξέος, ή/και ένα επιδιαλύτωμα αυτής παρέχονται από την παρούσα εφεύρεση. Οι εν λόγω κρυσταλλικές μορφές είναι εξαιρετικά χρήσιμες ως υλικά για την παρασκευή φαρμάκων. Νέες διαδικασίες για την παρασκευή παραγώγων 6,7-ακόρεστης-7-καρβαμοϋλ μορφινάνης παρέχονται επίσης από την παρούσα εφεύρεση.
CY20191101018T 2010-11-12 2019-09-26 Κρυσταλλικο παραγωγο 6,7-ακορεστης-7-καρβαμοϋλ μορφινανης, και μεθοδος για την παραγωγη αυτου CY1123670T1 (el)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010253688 2010-11-12
PCT/JP2011/076034 WO2012063933A1 (ja) 2010-11-12 2011-11-11 6,7-不飽和-7-カルバモイルモルヒナン誘導体の結晶およびその製造方法

Publications (1)

Publication Number Publication Date
CY1123670T1 true CY1123670T1 (el) 2021-10-29

Family

ID=46051070

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CY20191101018T CY1123670T1 (el) 2010-11-12 2019-09-26 Κρυσταλλικο παραγωγο 6,7-ακορεστης-7-καρβαμοϋλ μορφινανης, και μεθοδος για την παραγωγη αυτου

Country Status (26)

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US (6) US9108975B2 (el)
EP (2) EP3560929B1 (el)
JP (2) JP5070364B2 (el)
KR (2) KR101486686B1 (el)
CN (2) CN103298819B (el)
AU (2) AU2011327113B9 (el)
BR (1) BR112013011593B1 (el)
CA (1) CA2814195C (el)
CY (1) CY1123670T1 (el)
DK (1) DK2639234T3 (el)
ES (1) ES2746207T3 (el)
HR (1) HRP20191597T1 (el)
HU (1) HUE044933T2 (el)
IL (2) IL225725A (el)
LT (1) LT2639234T (el)
MX (2) MX348228B (el)
PH (2) PH12013500740A1 (el)
PL (1) PL2639234T3 (el)
PT (1) PT2639234T (el)
RS (1) RS59256B1 (el)
RU (2) RU2607084C2 (el)
SI (1) SI2639234T1 (el)
TW (2) TWI545124B (el)
UA (1) UA115028C2 (el)
WO (1) WO2012063933A1 (el)
ZA (1) ZA201301726B (el)

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WO2006126529A1 (ja) 2005-05-25 2006-11-30 Shionogi & Co., Ltd. 6,7-不飽和-7-カルバモイル置換モルヒナン誘導体
TWI545124B (zh) * 2010-11-12 2016-08-11 鹽野義製藥股份有限公司 6,7-不飽合-7-胺甲醯基嗎啡喃衍生物之結晶及其製造方法
US10952968B2 (en) 2012-05-14 2021-03-23 Shionogi & Co., Ltd. Preparation containing 6,7-unsaturated-7-carbamoyl morphinan derivatives
JOP20130273B1 (ar) 2012-09-11 2021-08-17 Genzyme Corp مثبطات انزيم (سينثاز) غلوكوسيل سيراميد
EP2931725B1 (en) 2012-12-14 2017-02-15 Purdue Pharma LP Nitrogen containing morphinan derivatives and the use thereof
US8980906B2 (en) 2012-12-14 2015-03-17 Purdue Pharma L.P. Pyridonemorphinan analogs and biological activity on opioid receptors
TW201441198A (zh) 2012-12-28 2014-11-01 Purdue Pharma Lp 7,8-環嗎啡喃類似物
EP2941431B1 (en) 2012-12-28 2017-10-25 Purdue Pharma L.P. Substituted morphinans and the use thereof
ES2968073T3 (es) * 2013-03-15 2024-05-07 Genzyme Corp Método de preparación de inhibidores de la glucosilceramida sintasa
ES2784690T3 (es) 2013-12-05 2020-09-29 Univ Bath Nuevos compuestos opioides y sus usos
US9340542B2 (en) 2013-12-26 2016-05-17 Purdue Pharma L.P. Propellane-based compounds and the use thereof
WO2018124062A1 (ja) 2016-12-26 2018-07-05 塩野義製薬株式会社 含量均一性を改善した製剤の製造方法
KR102201609B1 (ko) * 2019-04-19 2021-01-12 연성정밀화학(주) 날데메딘의 제조방법
WO2021100728A1 (ja) 2019-11-20 2021-05-27 塩野義製薬株式会社 6,7-不飽和-7-カルバモイルモルヒナン誘導体含有固形製剤
AU2021215396A1 (en) 2020-02-03 2022-09-29 Genzyme Corporation Methods for treating neurological symptoms associated with lysosomal storage diseases
BR112023000798A2 (pt) 2020-07-24 2023-02-07 Genzyme Corp Composições farmacêuticas compreendendo venglustat
IT202300009864A1 (it) * 2023-05-16 2024-11-16 Procos Spa Processo per la preparazione di naldemedina

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2801509A1 (de) * 1978-01-12 1979-07-19 Schering Ag 1,2,4-oxadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel
US4668685A (en) 1984-07-05 1987-05-26 E.I. Du Pont De Nemours And Company Substituted benzoate ester prodrug derivatives of 3-hydroxymorphinans, which are analgesics or narcotic antagonists
AU5891600A (en) * 1999-07-01 2001-01-22 Chemrx Advanced Technologies, Inc. Process for synthesizing oxadiazoles
DE10161963A1 (de) * 2001-12-17 2003-07-03 Johannes Schuetz 6-Aminomorphinanderivate, Herstellungsverfahren dafür und deren Verwendung
WO2006126529A1 (ja) * 2005-05-25 2006-11-30 Shionogi & Co., Ltd. 6,7-不飽和-7-カルバモイル置換モルヒナン誘導体
TWI545124B (zh) * 2010-11-12 2016-08-11 鹽野義製藥股份有限公司 6,7-不飽合-7-胺甲醯基嗎啡喃衍生物之結晶及其製造方法

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AU2011327113B8 (en) 2015-07-16
US9951082B2 (en) 2018-04-24
JPWO2012063933A1 (ja) 2014-05-12
RU2607084C2 (ru) 2017-01-10
KR101500915B1 (ko) 2015-03-10
WO2012063933A1 (ja) 2012-05-18
AU2011327113B2 (en) 2015-06-25
EP2639234A4 (en) 2014-04-23
IL243188A (en) 2017-12-31
EP2639234A1 (en) 2013-09-18
IL225725A0 (en) 2013-06-27
US9315512B2 (en) 2016-04-19
CN103298819A (zh) 2013-09-11
CN103298819B (zh) 2015-07-08
PH12015501226A1 (en) 2015-09-07
US20130231485A1 (en) 2013-09-05
ES2746207T3 (es) 2020-03-05
CA2814195A1 (en) 2012-05-18
US20170066774A1 (en) 2017-03-09
HRP20191597T1 (hr) 2019-11-29
AU2011327113A8 (en) 2015-07-16
US20160031896A1 (en) 2016-02-04
IL225725A (en) 2017-09-28
RS59256B1 (sr) 2019-10-31
MX338392B (es) 2016-04-13
BR112013011593A2 (pt) 2016-08-09
AU2011327113A1 (en) 2013-05-02
EP2639234B1 (en) 2019-07-03
TW201704239A (zh) 2017-02-01
AU2015221439A1 (en) 2015-09-17
TWI545124B (zh) 2016-08-11
PL2639234T3 (pl) 2019-12-31
US9902732B2 (en) 2018-02-27
US20160024102A1 (en) 2016-01-28
BR112013011593B1 (pt) 2022-02-22
KR101486686B1 (ko) 2015-01-26
CN105131003A (zh) 2015-12-09
KR20130121119A (ko) 2013-11-05
CN105131003B (zh) 2017-09-26
AU2011327113B9 (en) 2015-07-30
PH12015501226B1 (en) 2015-09-07
EP3560929A3 (en) 2020-01-01
SI2639234T1 (sl) 2019-10-30
EP3560929B1 (en) 2021-05-19
PH12013500740A1 (en) 2013-05-20
CA2814195C (en) 2020-03-10
US9108975B2 (en) 2015-08-18
JP2012162527A (ja) 2012-08-30
DK2639234T3 (da) 2019-09-23
US9296756B2 (en) 2016-03-29
MX348228B (es) 2017-05-31
US20180072748A1 (en) 2018-03-15
HUE044933T2 (hu) 2019-11-28
TW201300392A (zh) 2013-01-01
ZA201301726B (en) 2014-08-27
JP5070364B2 (ja) 2012-11-14
TWI597282B (zh) 2017-09-01
UA115028C2 (uk) 2017-09-11
LT2639234T (lt) 2019-09-25
RU2643807C1 (ru) 2018-02-06
JP5191574B2 (ja) 2013-05-08
AU2015221439B2 (en) 2016-07-14
RU2013126801A (ru) 2014-12-20
US20160194333A1 (en) 2016-07-07
PT2639234T (pt) 2019-09-27
KR20140057410A (ko) 2014-05-12
MX2013005241A (es) 2013-05-28
EP3560929A2 (en) 2019-10-30
US9464094B2 (en) 2016-10-11

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