NZ617773A - Method of preparing an inhibitor of cytochrome p450 monooxygenase, and intermediates involved - Google Patents

Method of preparing an inhibitor of cytochrome p450 monooxygenase, and intermediates involved

Info

Publication number
NZ617773A
NZ617773A NZ617773A NZ61777310A NZ617773A NZ 617773 A NZ617773 A NZ 617773A NZ 617773 A NZ617773 A NZ 617773A NZ 61777310 A NZ61777310 A NZ 61777310A NZ 617773 A NZ617773 A NZ 617773A
Authority
NZ
New Zealand
Prior art keywords
monooxygenase
cytochrome
inhibitor
preparing
coupling
Prior art date
Application number
NZ617773A
Other languages
English (en)
Inventor
Kenneth Kent
Doug Cordeau
Richard Yu
Leah Easton
Duong Tran
Steven Pfeiffer
Aaron Cullen
Richard Polniaszek
Eric Dowdy
Zhongxin Zhou
Original Assignee
Gilead Sciences 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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=42634770&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NZ617773(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Gilead Sciences Inc filed Critical Gilead Sciences Inc
Priority to NZ708978A priority Critical patent/NZ708978A/en
Publication of NZ617773A publication Critical patent/NZ617773A/en

Links

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)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Virology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (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)
NZ617773A 2009-04-03 2010-04-01 Method of preparing an inhibitor of cytochrome p450 monooxygenase, and intermediates involved NZ617773A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
NZ708978A NZ708978A (en) 2009-04-03 2010-04-01 Method of preparing an inhibitor of cytochrome p450 monoxygenase, and intermediates involved

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US16649809P 2009-04-03 2009-04-03
NZ59486410A NZ594864A (en) 2009-04-03 2010-04-01 Method of preparing an inhibitor of cytochrome p450 monooxygenase, and intermediates involved

Publications (1)

Publication Number Publication Date
NZ617773A true NZ617773A (en) 2016-02-26

Family

ID=42634770

Family Applications (4)

Application Number Title Priority Date Filing Date
NZ617773A NZ617773A (en) 2009-04-03 2010-04-01 Method of preparing an inhibitor of cytochrome p450 monooxygenase, and intermediates involved
NZ726536A NZ726536A (en) 2009-04-03 2010-04-01 Method of preparing an inhibitor of cytochrome p450 monoxygenase, and intermediates involved
NZ708978A NZ708978A (en) 2009-04-03 2010-04-01 Method of preparing an inhibitor of cytochrome p450 monoxygenase, and intermediates involved
NZ59486410A NZ594864A (en) 2009-04-03 2010-04-01 Method of preparing an inhibitor of cytochrome p450 monooxygenase, and intermediates involved

Family Applications After (3)

Application Number Title Priority Date Filing Date
NZ726536A NZ726536A (en) 2009-04-03 2010-04-01 Method of preparing an inhibitor of cytochrome p450 monoxygenase, and intermediates involved
NZ708978A NZ708978A (en) 2009-04-03 2010-04-01 Method of preparing an inhibitor of cytochrome p450 monoxygenase, and intermediates involved
NZ59486410A NZ594864A (en) 2009-04-03 2010-04-01 Method of preparing an inhibitor of cytochrome p450 monooxygenase, and intermediates involved

Country Status (27)

Country Link
US (4) US8497396B2 (enExample)
EP (2) EP2414325B1 (enExample)
JP (8) JP5612662B2 (enExample)
KR (3) KR20180077324A (enExample)
CN (4) CN104876888B (enExample)
AP (1) AP2887A (enExample)
AR (1) AR076027A1 (enExample)
AU (1) AU2010232559B2 (enExample)
BR (1) BRPI1012638B8 (enExample)
CA (4) CA2925137C (enExample)
CL (1) CL2011002370A1 (enExample)
CO (1) CO6400216A2 (enExample)
EA (2) EA201590979A1 (enExample)
EC (1) ECSP11011391A (enExample)
ES (1) ES2548252T3 (enExample)
HK (1) HK1223912A1 (enExample)
IL (4) IL215399A (enExample)
MX (2) MX2011010397A (enExample)
NZ (4) NZ617773A (enExample)
PE (1) PE20120617A1 (enExample)
PT (1) PT2414325E (enExample)
SG (2) SG174585A1 (enExample)
TW (2) TW201518283A (enExample)
UA (1) UA108738C2 (enExample)
UY (1) UY32535A (enExample)
WO (1) WO2010115000A2 (enExample)
ZA (1) ZA201107430B (enExample)

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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
ES2543923T3 (es) * 2011-05-02 2015-08-25 Gilead Sciences, Inc. Sales sólidas amorfas de Cobicistat (GS-9350)
MX2014009344A (es) * 2012-02-03 2015-05-11 Gilead Sciences Inc Metodos e intermediarios para preparar agentes farmaceuticos.
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
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
WO2014057498A2 (en) 2012-10-08 2014-04-17 Mylan Laboratories Ltd. Process for the preparation of cobicistat intermediates
WO2014105777A1 (en) * 2012-12-26 2014-07-03 Assia Chemical Industries Ltd. Cobicostat dichlohydrate salt
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
JP2016538312A (ja) * 2013-11-29 2016-12-08 マイラン ラボラトリーズ リミテッドＭｙｌａｎ Ｌａｂｏｒａｔｏｒｉｅｓ Ｌｉｍｉｔｅｄ 非晶質のコビシスタットの固体分散体
EP3077373B1 (en) 2013-12-03 2018-09-12 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
US10351556B2 (en) * 2015-02-18 2019-07-16 Msn Laboratories Private Limited Process for the preparation of 1,3-thiazol-5-ylmethyl [(2R,5R)-5-{[(2s)-2-[(methyl{[2-(propan-2-yl)-1,3-thiazol-4YL] 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
US20180085387A1 (en) 2016-09-27 2018-03-29 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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US20030153771A1 (en) 2001-09-27 2003-08-14 Kolb Hartmuth C. Large scale synthesis of optically pure aziridines
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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
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KR101477822B1 (ko) * 2006-07-07 2015-01-02 길리애드 사이언시즈, 인코포레이티드 치료제의 약동학 특성의 모듈레이터
PT3150586T (pt) * 2007-02-23 2020-03-31 Gilead Sciences Inc Moduladores de propriedades farmacocinéticas de agentes terapêuticos
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PT2231628E (pt) * 2008-01-04 2015-12-29 Gilead Sciences Inc Inibidores de citocromo p450
EA201591353A1 (ru) 2008-05-02 2016-01-29 Джилид Сайэнс, Инк. Применение частиц твердого носителя для улучшения технологических характеристик фармацевтического агента
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
JP6491706B2 (ja) 2019-03-27
NZ708978A (en) 2017-01-27
US9428473B2 (en) 2016-08-30
HK1223912A1 (en) 2017-08-11
TWI464165B (zh) 2014-12-11
MX338731B (es) 2016-04-28
IL237643A (en) 2017-01-31
ECSP11011391A (es) 2012-03-30
TW201518283A (zh) 2015-05-16
IL237642A0 (en) 2015-04-30
JP2020189861A (ja) 2020-11-26
IL250068A0 (en) 2017-03-30
WO2010115000A3 (en) 2011-09-22
EA201590979A1 (ru) 2016-02-29
CA3083433A1 (en) 2010-10-07
KR20120006035A (ko) 2012-01-17
ES2548252T3 (es) 2015-10-15
US8497396B2 (en) 2013-07-30
AU2010232559B2 (en) 2015-06-18
US20140088304A1 (en) 2014-03-27
CN104876888B (zh) 2018-06-15
CL2011002370A1 (es) 2012-05-25
CA2925137C (en) 2018-07-31
US8853210B2 (en) 2014-10-07
JP2018162274A (ja) 2018-10-18
HK1214265A1 (zh) 2016-07-22
JP6336161B2 (ja) 2018-06-06
EA201190179A1 (ru) 2013-01-30
PE20120617A1 (es) 2012-05-26
CN111217808A (zh) 2020-06-02
US20100256366A1 (en) 2010-10-07
SG174585A1 (en) 2011-10-28
EP2414325B1 (en) 2015-08-26
US20150005493A1 (en) 2015-01-01
CN102438982A (zh) 2012-05-02
US20160002186A1 (en) 2016-01-07
NZ594864A (en) 2014-03-28
ZA201107430B (en) 2012-12-27
WO2010115000A2 (en) 2010-10-07
AU2010232559A1 (en) 2011-10-06
NZ726536A (en) 2018-04-27
CA2925137A1 (en) 2010-10-07
EP2414325A2 (en) 2012-02-08
CA2754698C (en) 2016-06-07
IL237643A0 (en) 2015-04-30
KR20180077324A (ko) 2018-07-06
BRPI1012638B8 (pt) 2021-05-25
JP6180561B2 (ja) 2017-08-16
CA2754698A1 (en) 2010-10-07
CN107382997A (zh) 2017-11-24
SG10201404926UA (en) 2015-02-27
BRPI1012638A2 (pt) 2016-04-05
AP2011005864A0 (en) 2011-10-31
JP2014193897A (ja) 2014-10-09
TW201100412A (en) 2011-01-01
KR20170043672A (ko) 2017-04-21
CA3008903A1 (en) 2010-10-07
JP5986599B2 (ja) 2016-09-06
UA108738C2 (uk) 2015-06-10
UY32535A (es) 2010-10-29
EP3009434A1 (en) 2016-04-20
JP2023002679A (ja) 2023-01-10
MX2011010397A (es) 2011-10-24
CA3008903C (en) 2021-06-08
HK1166976A1 (zh) 2012-11-16
CN107382997B (zh) 2021-02-26
JP2017122107A (ja) 2017-07-13
CO6400216A2 (es) 2012-03-15
KR101874557B1 (ko) 2018-07-04
KR101728375B1 (ko) 2017-04-19
PT2414325E (pt) 2015-10-29
IL215399A0 (en) 2011-12-29
IL215399A (en) 2015-11-30
CN104876888A (zh) 2015-09-02
JP5612662B2 (ja) 2014-10-22
US9115100B2 (en) 2015-08-25
AU2010232559A8 (en) 2011-11-10
AR076027A1 (es) 2011-05-11
JP2012522797A (ja) 2012-09-27
HK1245785A1 (zh) 2018-08-31
CN102438982B (zh) 2015-05-06
JP2018008983A (ja) 2018-01-18
IL237642A (en) 2017-01-31
JP2016128476A (ja) 2016-07-14
BRPI1012638B1 (pt) 2021-04-20
AP2887A (en) 2014-05-31
CA3083433C (en) 2022-08-09
EA022739B1 (ru) 2016-02-29

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