CA2925137C - Methods and intermediates for preparing pharmaceutical agents useful to modify the pharmacokinetics of a co-administered drug - Google Patents

Methods and intermediates for preparing pharmaceutical agents useful to modify the pharmacokinetics of a co-administered drug Download PDF

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Publication number
CA2925137C
CA2925137C CA2925137A CA2925137A CA2925137C CA 2925137 C CA2925137 C CA 2925137C CA 2925137 A CA2925137 A CA 2925137A CA 2925137 A CA2925137 A CA 2925137A CA 2925137 C CA2925137 C CA 2925137C
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Canada
Prior art keywords
formula
compound
salt
dichloromethane
temperature
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CA2925137A
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English (en)
French (fr)
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CA2925137A1 (en
Inventor
Richard Polniaszek
Steven Pfeiffer
Richard Yu
Aaron Cullen
Eric Dowdy
Duong Tran
Kenneth Kent
Zhongxin Zhou
Doug Cordeau
Leah Easton
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Gilead Sciences Inc
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Gilead Sciences Inc
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Application filed by Gilead Sciences Inc filed Critical Gilead Sciences Inc
Priority to CA3008903A priority Critical patent/CA3008903C/en
Publication of CA2925137A1 publication Critical patent/CA2925137A1/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/28—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • A61P31/12—Antivirals
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C07C209/70—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by reduction of unsaturated amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/34—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C307/02—Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C307/04—Diamides of sulfuric acids
    • C07C307/06—Diamides of sulfuric acids having nitrogen atoms of the sulfamide groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Virology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2925137A 2009-04-03 2010-04-01 Methods and intermediates for preparing pharmaceutical agents useful to modify the pharmacokinetics of a co-administered drug Active CA2925137C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3008903A CA3008903C (en) 2009-04-03 2010-04-01 Methods and intermediates for preparing pharmaceutical agents useful to modify the pharmacokinetics of a co-administered drug

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US16649809P 2009-04-03 2009-04-03
US61/166,498 2009-04-03
CA2754698A CA2754698C (en) 2009-04-03 2010-04-01 Methods and intermediates for preparing pharmaceutical agents

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA2754698A Division CA2754698C (en) 2009-04-03 2010-04-01 Methods and intermediates for preparing pharmaceutical agents

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA3008903A Division CA3008903C (en) 2009-04-03 2010-04-01 Methods and intermediates for preparing pharmaceutical agents useful to modify the pharmacokinetics of a co-administered drug

Publications (2)

Publication Number Publication Date
CA2925137A1 CA2925137A1 (en) 2010-10-07
CA2925137C true CA2925137C (en) 2018-07-31

Family

ID=42634770

Family Applications (4)

Application Number Title Priority Date Filing Date
CA2925137A Active CA2925137C (en) 2009-04-03 2010-04-01 Methods and intermediates for preparing pharmaceutical agents useful to modify the pharmacokinetics of a co-administered drug
CA3083433A Active CA3083433C (en) 2009-04-03 2010-04-01 Methods and intermediates for preparing pharmaceutical agents
CA3008903A Active CA3008903C (en) 2009-04-03 2010-04-01 Methods and intermediates for preparing pharmaceutical agents useful to modify the pharmacokinetics of a co-administered drug
CA2754698A Active CA2754698C (en) 2009-04-03 2010-04-01 Methods and intermediates for preparing pharmaceutical agents

Family Applications After (3)

Application Number Title Priority Date Filing Date
CA3083433A Active CA3083433C (en) 2009-04-03 2010-04-01 Methods and intermediates for preparing pharmaceutical agents
CA3008903A Active CA3008903C (en) 2009-04-03 2010-04-01 Methods and intermediates for preparing pharmaceutical agents useful to modify the pharmacokinetics of a co-administered drug
CA2754698A Active CA2754698C (en) 2009-04-03 2010-04-01 Methods and intermediates for preparing pharmaceutical agents

Country Status (27)

Country Link
US (4) US8497396B2 (https=)
EP (2) EP3009434A1 (https=)
JP (8) JP5612662B2 (https=)
KR (3) KR101874557B1 (https=)
CN (4) CN111217808A (https=)
AP (1) AP2887A (https=)
AR (1) AR076027A1 (https=)
AU (1) AU2010232559B2 (https=)
BR (1) BRPI1012638B8 (https=)
CA (4) CA2925137C (https=)
CL (1) CL2011002370A1 (https=)
CO (1) CO6400216A2 (https=)
EA (2) EA022739B1 (https=)
EC (1) ECSP11011391A (https=)
ES (1) ES2548252T3 (https=)
HK (1) HK1223912A1 (https=)
IL (4) IL215399A (https=)
MX (2) MX338731B (https=)
NZ (4) NZ594864A (https=)
PE (1) PE20120617A1 (https=)
PT (1) PT2414325E (https=)
SG (2) SG10201404926UA (https=)
TW (2) TWI464165B (https=)
UA (1) UA108738C2 (https=)
UY (1) UY32535A (https=)
WO (1) WO2010115000A2 (https=)
ZA (1) ZA201107430B (https=)

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UA108738C2 (uk) 2009-04-03 2015-06-10 Спосіб одержання інгібітора цитохром р450 монооксигенази та залучені проміжні сполуки
JP2012140390A (ja) * 2011-01-06 2012-07-26 Sumitomo Chemical Co Ltd α−アミノ−γ−ブチロラクトンの製造方法
JP2014513123A (ja) * 2011-05-02 2014-05-29 ギリアード サイエンシーズ， インコーポレイテッド 無定形固体の塩
SG10201509336RA (en) 2012-02-03 2015-12-30 Gilead Sciences Inc Methods and intermediates for preparing pharmaceutical agents
CN103694196A (zh) * 2012-09-27 2014-04-02 上海迪赛诺化学制药有限公司 细胞色素p450单加氧酶抑制剂中间体及其制法和用途
WO2014047849A1 (zh) * 2012-09-27 2014-04-03 上海迪赛诺化学制药有限公司 细胞色素p450单加氧酶抑制剂中间体及其制法和用途
WO2014057498A2 (en) 2012-10-08 2014-04-17 Mylan Laboratories Ltd. Process for the preparation of cobicistat intermediates
JP2016504364A (ja) * 2012-12-26 2016-02-12 アッシア・ケミカル・インダストリーズ・リミテッド コビシスタット塩
CN104370777A (zh) * 2013-08-13 2015-02-25 上海迪赛诺化学制药有限公司 合成(2r,5r)-1,6-二苯基己烷-2,5-二胺及其盐的中间体及所述中间体的制备方法和应用
US20170035911A1 (en) * 2013-11-29 2017-02-09 Mylan Laboratories Ltd. Amorphous Cobicistat Solid Dispersion
WO2015083066A1 (en) 2013-12-03 2015-06-11 Mylan Laboratories Ltd. Preparation of cobicistat intermediates
CN104193643B (zh) * 2014-09-12 2016-02-10 宁波九胜创新医药科技有限公司 用于合成抗艾滋病药物增强剂cobicistat的中间体
CN104447472A (zh) * 2014-11-06 2015-03-25 江苏森萱医药化工股份有限公司 D)-2-苄基-n,n-二甲基氮杂环丙烷基-1-磺酰胺合成方法
CN104557565B (zh) * 2015-01-08 2016-07-06 浙江工业大学 抗艾滋病药物增强剂Cobicistat关键中间体盐酸盐的制备方法
US10454867B2 (en) * 2015-02-09 2019-10-22 Airwatch Llc Enhanced e-mail delivery to mobile devices
WO2016132378A2 (en) * 2015-02-18 2016-08-25 Msn Laboratories Private Limited Novel process for the preparation of 1,3-thiazol-5-ylmethyl [(2r,5r)-5-{[(2s)-2- [(methyl{[2-(propan-2-yl)- 1,3-thiazol-4-yl] methyl} carbamoyl) amino] -4-(morpholin-4-yl)butanoyl]amino}-1,6-diphenylhexan-2-yl] carbamate
CN107674039A (zh) * 2016-08-01 2018-02-09 上海朴颐化学科技有限公司 一种可比西他中间体的制备方法
WO2018064071A1 (en) 2016-09-27 2018-04-05 Gilead Sciences, Inc. Therapeutic compositions for treatment of human immunodeficiency virus
CN109912530A (zh) * 2017-12-13 2019-06-21 上海奥博生物医药技术有限公司 一种可比司他原料杂质的制备方法
CN109232301B (zh) * 2018-10-15 2021-01-01 天津希恩思生化科技有限公司 一种四异丙基肼的制备方法
CN110642721B (zh) * 2018-12-21 2022-09-30 安徽贝克生物制药有限公司 盐酸司来吉兰的制备方法
CN110878071A (zh) * 2019-11-21 2020-03-13 华南农业大学 一种α-氨基-γ-丁内酯及其盐的制备方法

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ATE332132T1 (de) * 1999-06-04 2006-07-15 Abbott Lab Verbesserte arzneizubereitungen enthaltend ritonavir
US20030153771A1 (en) 2001-09-27 2003-08-14 Kolb Hartmuth C. Large scale synthesis of optically pure aziridines
WO2003106445A1 (en) * 2002-06-12 2003-12-24 Qsi Pharma A/S Compounds and methods for controlling bacterial virulence
EP1771536A1 (en) * 2004-07-23 2007-04-11 The Procter and Gamble Company Liquid detergent composition for improved low temperature grease cleaning and starch soil cleaning
US7786153B2 (en) * 2005-03-02 2010-08-31 Abbott Laboratories Inc. Compounds that are useful for improving pharmacokinetics
SG183007A1 (en) 2006-07-07 2012-08-30 Gilead Sciences Inc Modulators of pharmacokinetic properties of therapeutics
PL3150586T3 (pl) * 2007-02-23 2020-06-01 Gilead Sciences, Inc. Modulatory farmakokinetycznych właściwości środków terapeutycznych
EP2170851B1 (en) * 2007-07-06 2013-09-04 Gilead Sciences, Inc. Modulators of pharmacokinetic properties of therapeutics
PT2231628E (pt) * 2008-01-04 2015-12-29 Gilead Sciences Inc Inibidores de citocromo p450
HRP20151357T1 (hr) 2008-05-02 2016-01-29 Gilead Sciences, Inc. Upotreba äśestica äśvrstog nosaäśa kako bi se poboljšala procesabilnost farmaceutskog agensa
UA108738C2 (uk) 2009-04-03 2015-06-10 Спосіб одержання інгібітора цитохром р450 монооксигенази та залучені проміжні сполуки

Also Published As

Publication number Publication date
PT2414325E (pt) 2015-10-29
ES2548252T3 (es) 2015-10-15
WO2010115000A3 (en) 2011-09-22
IL215399A (en) 2015-11-30
EP3009434A1 (en) 2016-04-20
CA2754698C (en) 2016-06-07
EP2414325A2 (en) 2012-02-08
HK1245785A1 (zh) 2018-08-31
IL237643A0 (en) 2015-04-30
JP6180561B2 (ja) 2017-08-16
US20150005493A1 (en) 2015-01-01
JP2012522797A (ja) 2012-09-27
EP2414325B1 (en) 2015-08-26
SG174585A1 (en) 2011-10-28
JP6336161B2 (ja) 2018-06-06
JP2018162274A (ja) 2018-10-18
KR101728375B1 (ko) 2017-04-19
KR101874557B1 (ko) 2018-07-04
CA3083433A1 (en) 2010-10-07
CN104876888A (zh) 2015-09-02
CA3083433C (en) 2022-08-09
CN107382997B (zh) 2021-02-26
IL237643A (en) 2017-01-31
CN102438982A (zh) 2012-05-02
MX338731B (es) 2016-04-28
ZA201107430B (en) 2012-12-27
JP2023002679A (ja) 2023-01-10
WO2010115000A2 (en) 2010-10-07
JP5986599B2 (ja) 2016-09-06
AP2011005864A0 (en) 2011-10-31
NZ726536A (en) 2018-04-27
PE20120617A1 (es) 2012-05-26
IL237642A (en) 2017-01-31
JP2016128476A (ja) 2016-07-14
NZ617773A (en) 2016-02-26
AU2010232559B2 (en) 2015-06-18
US20140088304A1 (en) 2014-03-27
EA022739B1 (ru) 2016-02-29
TW201100412A (en) 2011-01-01
NZ594864A (en) 2014-03-28
EA201190179A1 (ru) 2013-01-30
EA201590979A1 (ru) 2016-02-29
IL237642A0 (en) 2015-04-30
HK1166976A1 (zh) 2012-11-16
CO6400216A2 (es) 2012-03-15
JP2017122107A (ja) 2017-07-13
SG10201404926UA (en) 2015-02-27
AR076027A1 (es) 2011-05-11
CN104876888B (zh) 2018-06-15
JP2018008983A (ja) 2018-01-18
ECSP11011391A (es) 2012-03-30
JP2020189861A (ja) 2020-11-26
JP5612662B2 (ja) 2014-10-22
IL215399A0 (en) 2011-12-29
TWI464165B (zh) 2014-12-11
AP2887A (en) 2014-05-31
CN111217808A (zh) 2020-06-02
US9115100B2 (en) 2015-08-25
US8497396B2 (en) 2013-07-30
CA3008903C (en) 2021-06-08
KR20170043672A (ko) 2017-04-21
BRPI1012638A2 (pt) 2016-04-05
HK1223912A1 (en) 2017-08-11
KR20120006035A (ko) 2012-01-17
BRPI1012638B8 (pt) 2021-05-25
CA3008903A1 (en) 2010-10-07
CA2925137A1 (en) 2010-10-07
CA2754698A1 (en) 2010-10-07
CL2011002370A1 (es) 2012-05-25
UY32535A (es) 2010-10-29
KR20180077324A (ko) 2018-07-06
HK1214265A1 (zh) 2016-07-22
BRPI1012638B1 (pt) 2021-04-20
US20100256366A1 (en) 2010-10-07
AU2010232559A8 (en) 2011-11-10
US8853210B2 (en) 2014-10-07
JP2014193897A (ja) 2014-10-09
US20160002186A1 (en) 2016-01-07
JP6491706B2 (ja) 2019-03-27
TW201518283A (zh) 2015-05-16
MX2011010397A (es) 2011-10-24
UA108738C2 (uk) 2015-06-10
US9428473B2 (en) 2016-08-30
CN102438982B (zh) 2015-05-06
AU2010232559A1 (en) 2011-10-06
NZ708978A (en) 2017-01-27
IL250068A0 (en) 2017-03-30
CN107382997A (zh) 2017-11-24

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