SG10201806450SA - PROCESSES FOR PREPARING (CYCLOPENTYL[d]PYRIMIDIN-4-YL)PIPERAZINE COMPOUNDS - Google Patents

PROCESSES FOR PREPARING (CYCLOPENTYL[d]PYRIMIDIN-4-YL)PIPERAZINE COMPOUNDS

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Publication number
SG10201806450SA
SG10201806450SA SG10201806450SA SG10201806450SA SG10201806450SA SG 10201806450S A SG10201806450S A SG 10201806450SA SG 10201806450S A SG10201806450S A SG 10201806450SA SG 10201806450S A SG10201806450S A SG 10201806450SA SG 10201806450S A SG10201806450S A SG 10201806450SA
Authority
SG
Singapore
Prior art keywords
pyrimidin
preparing
processes
cyclopentyl
piperazine compounds
Prior art date
Application number
SG10201806450SA
Other languages
English (en)
Inventor
Francis Gosselin
Chong Han
Hans Iding
Reinhard Reents
Scott Savage
Beat Wirz
Original Assignee
Hoffmann La Roche
Genentech 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 Hoffmann La Roche, Genentech Inc filed Critical Hoffmann La Roche
Publication of SG10201806450SA publication Critical patent/SG10201806450SA/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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
    • 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
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00Separation of optically-active compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00Preparation of carboxylic acid nitriles
    • C07C253/30Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00Preparation of carboxylic acid nitriles
    • C07C253/32Separation; Purification; Stabilisation; Use of additives
    • C07C253/34Separation; Purification
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00Carboxylic acid nitriles
    • C07C255/01Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/19Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
    • C07C255/22Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton containing cyano groups and at least two carboxyl groups bound to the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/30Halogen atoms or nitro radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/42One nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52Two oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52Two oxygen atoms
    • C07D239/54Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D241/00Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/14Hydrolases (3)
    • C12N9/78Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5)
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12YENZYMES
    • C12Y305/00Hydrolases acting on carbon-nitrogen bonds, other than peptide bonds (3.5)
    • C12Y305/05Hydrolases acting on carbon-nitrogen bonds, other than peptide bonds (3.5) in nitriles (3.5.5)
    • C12Y305/05001Nitrilase (3.5.5.1)
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07Optical isomers
    • 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)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Molecular Biology (AREA)
  • Biomedical Technology (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
SG10201806450SA 2014-09-26 2015-09-25 PROCESSES FOR PREPARING (CYCLOPENTYL[d]PYRIMIDIN-4-YL)PIPERAZINE COMPOUNDS SG10201806450SA (en)

Applications Claiming Priority (1)

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US201462055893P 2014-09-26 2014-09-26

Publications (1)

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SG10201806450SA SG10201806450SA (en) 2014-09-26 2015-09-25 PROCESSES FOR PREPARING (CYCLOPENTYL[d]PYRIMIDIN-4-YL)PIPERAZINE COMPOUNDS
SG11201702324QA SG11201702324QA (en) 2014-09-26 2015-09-25 PROCESSES FOR PREPARING (CYCLOPENTYL[d]PYRIMIDIN-4-YL)PIPERAZINE COMPOUNDS

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Country Status (21)

Country Link
US (2) US10457648B2 (es)
EP (2) EP3626710B1 (es)
JP (3) JP6676043B2 (es)
KR (1) KR102513869B1 (es)
CN (2) CN107001287B (es)
AR (2) AR102088A1 (es)
AU (2) AU2015320510B2 (es)
BR (1) BR112017005931B1 (es)
CA (2) CA3190507A1 (es)
ES (1) ES2749100T3 (es)
HR (1) HRP20191943T1 (es)
IL (2) IL251313B (es)
MA (1) MA51165A (es)
MX (2) MX368298B (es)
MY (1) MY188699A (es)
PL (1) PL3197875T3 (es)
RU (2) RU2712224C2 (es)
SG (2) SG10201806450SA (es)
SI (1) SI3197875T1 (es)
WO (1) WO2016049414A1 (es)
ZA (1) ZA201702769B (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112898210A (zh) 2013-11-15 2021-06-04 豪夫迈·罗氏有限公司 用于制备嘧啶基环戊烷化合物的方法
CN107001287B (zh) * 2014-09-26 2020-09-04 豪夫迈·罗氏有限公司 用于制备(环戊并[d]嘧啶-4-基)哌嗪化合物的方法
EP4165026A1 (en) 2020-06-16 2023-04-19 F. Hoffmann-La Roche AG Process for making hydroxylated cyclopentylpyrimidine compounds
CN112359078A (zh) * 2021-01-12 2021-02-12 凯莱英生命科学技术(天津)有限公司 异丁酸酯类化合物的手性拆分方法

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US1045764A (en) 1912-04-30 1912-11-26 Samuel Allen Guiberson Jr Casing-elevator.
GB9400889D0 (en) 1994-01-18 1994-03-16 Sandoz Ltd Novel compounds
CN1898246B (zh) * 2003-10-28 2010-10-27 先灵公司 制备取代的5-氨基-吡唑并[4,3-e]-1,2,4-三唑并[1,5-c]嘧啶的方法
US20080004269A1 (en) 2004-11-04 2008-01-03 Yuelian Xu Pyrazolylmethy Heteroaryl Derivatives
WO2006053112A1 (en) * 2004-11-10 2006-05-18 Synta Pharmaceuticals Corp. Process for preparing trisubstituted pyrimidine compounds
US8063050B2 (en) 2006-07-06 2011-11-22 Array Biopharma Inc. Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors
UA95641C2 (en) 2006-07-06 2011-08-25 Эррей Биофарма Инк. Hydroxylated cyclopenta [d] pyrimidines as akt protein kinase inhibitors
WO2010002954A1 (en) * 2008-07-02 2010-01-07 Wyeth (2-aryl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)morpholine compounds, their use as mtor kinase and pi3 kinase inhibitors, and their syntheses
US8703581B2 (en) 2011-06-15 2014-04-22 Applied Materials, Inc. Water soluble mask for substrate dicing by laser and plasma etch
DE102011080205A1 (de) 2011-08-01 2013-02-07 Bayerische Motoren Werke Aktiengesellschaft Verfahren zur Herstellung faserverstärkter keramischer Formkörper
WO2013068785A1 (en) * 2011-11-09 2013-05-16 Actelion Pharmaceuticals Ltd Indanone and indandione derivatives and heterocyclic analogs
CN104471070B (zh) * 2012-05-17 2018-09-25 基因泰克公司 制备羟基化环戊并嘧啶化合物和其盐的方法
WO2013173736A1 (en) 2012-05-17 2013-11-21 Array Biopharma Inc. Process for making hydroxylated cyclopentylpyrimidine compounds
RU2643146C2 (ru) 2012-05-17 2018-01-31 Дженентек, Инк. Способ получения аминокислотных соединений
JP6284928B2 (ja) 2012-05-17 2018-02-28 アレイ バイオファーマ、インコーポレイテッド ヒドロキシル化シクロペンチルピリミジン化合物を作製するためのプロセス
CN112898210A (zh) 2013-11-15 2021-06-04 豪夫迈·罗氏有限公司 用于制备嘧啶基环戊烷化合物的方法
US9437599B2 (en) * 2014-08-12 2016-09-06 Kabushiki Kaisha Toshiba Nonvolatile semiconductor memory device and method of manufacturing the same
CN107001287B (zh) * 2014-09-26 2020-09-04 豪夫迈·罗氏有限公司 用于制备(环戊并[d]嘧啶-4-基)哌嗪化合物的方法
KR102256602B1 (ko) 2017-12-14 2021-05-26 주식회사 엘지에너지솔루션 전압 측정 장치 및 방법

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CN112062727A (zh) 2020-12-11
PL3197875T3 (pl) 2020-03-31
US10870626B2 (en) 2020-12-22
KR102513869B1 (ko) 2023-03-23
RU2017114035A3 (es) 2019-04-22
EP3197875B1 (en) 2019-08-14
MA51165A (fr) 2020-10-21
MX2017003791A (es) 2017-08-02
US20200010428A1 (en) 2020-01-09
AU2019253849B2 (en) 2020-07-09
IL251313B (en) 2019-08-29
BR112017005931B1 (pt) 2024-04-30
MX2019011513A (es) 2019-11-18
EP3626710B1 (en) 2022-02-16
SI3197875T1 (sl) 2019-12-31
EP3197875A1 (en) 2017-08-02
CN112062727B (zh) 2023-10-31
NZ731073A (en) 2021-11-26
JP2017529371A (ja) 2017-10-05
AU2019253849A1 (en) 2019-11-14
EP3626710A1 (en) 2020-03-25
IL251313A0 (en) 2017-05-29
CN107001287A (zh) 2017-08-01
CA3190507A1 (en) 2016-03-31
US20170247338A1 (en) 2017-08-31
RU2732404C2 (ru) 2020-09-16
CA2962901A1 (en) 2016-03-31
ES2749100T3 (es) 2020-03-19
MY188699A (en) 2021-12-23
JP2020059762A (ja) 2020-04-16
SG11201702324QA (en) 2017-04-27
AR102088A1 (es) 2017-02-01
JP6926254B2 (ja) 2021-08-25
KR20170063809A (ko) 2017-06-08
JP2021169535A (ja) 2021-10-28
US10457648B2 (en) 2019-10-29
AU2015320510A1 (en) 2017-05-04
BR112017005931A2 (pt) 2017-12-19
RU2020101483A (ru) 2020-03-13
JP6676043B2 (ja) 2020-04-08
AR124856A2 (es) 2023-05-10
RU2017114035A (ru) 2018-10-26
IL267756B (en) 2020-06-30
AU2015320510B2 (en) 2019-11-21
RU2020101483A3 (es) 2020-05-12
IL267756A (en) 2019-08-29
MX368298B (es) 2019-09-27
RU2712224C2 (ru) 2020-01-27
WO2016049414A1 (en) 2016-03-31
HRP20191943T1 (hr) 2020-01-10
ZA201702769B (en) 2019-07-31
CN107001287B (zh) 2020-09-04

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