JP6805232B2 - (1r,2r,5r)−5−アミノ−2−メチルシクロヘキサノール塩酸塩の合成方法及びそれに有用な中間体 - Google Patents

(1r,2r,5r)−5−アミノ−2−メチルシクロヘキサノール塩酸塩の合成方法及びそれに有用な中間体 Download PDF

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JP6805232B2
JP6805232B2 JP2018503482A JP2018503482A JP6805232B2 JP 6805232 B2 JP6805232 B2 JP 6805232B2 JP 2018503482 A JP2018503482 A JP 2018503482A JP 2018503482 A JP2018503482 A JP 2018503482A JP 6805232 B2 JP6805232 B2 JP 6805232B2
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naoh
dcm
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JP2018521085A (ja
JP2018521085A5 (enExample
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ジョセフ コノリー テレンス
ジョセフ コノリー テレンス
マン ホン‐ワフ
マン ホン‐ワフ
ナガラジャン ペリヤンディ
ナガラジャン ペリヤンディ
ラジェンディラン チンナピライ
ラジェンディラン チンナピライ
ヴェンカテスワルル ジャスティ
ヴェンカテスワルル ジャスティ
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Celgene Corp
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/54Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions
    • C07C209/58Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions from or via amides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/82Purification; Separation; Stabilisation; Use of additives
    • C07C209/86Separation
    • C07C209/88Separation of optical isomers
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/39Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
    • C07C211/40Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing only non-condensed rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00Preparation of carboxylic acid amides
    • C07C231/02Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/04Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/30Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07Optical isomers
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
JP2018503482A 2015-07-24 2016-07-22 (1r,2r,5r)−5−アミノ−2−メチルシクロヘキサノール塩酸塩の合成方法及びそれに有用な中間体 Active JP6805232B2 (ja)

Applications Claiming Priority (3)

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US201562196363P 2015-07-24 2015-07-24
US62/196,363 2015-07-24
PCT/US2016/043511 WO2017019487A1 (en) 2015-07-24 2016-07-22 Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein

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JP2018521085A5 JP2018521085A5 (enExample) 2019-08-22
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JP2020200723A Active JP7165178B2 (ja) 2015-07-24 2020-12-03 (1r,2r,5r)-5-アミノ-2-メチルシクロヘキサノール塩酸塩の合成方法及びそれに有用な中間体

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US (4) US10252981B2 (enExample)
EP (2) EP3325432B1 (enExample)
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CN (1) CN107922287B (enExample)
AU (2) AU2016297784B2 (enExample)
CA (2) CA3208587A1 (enExample)
ES (2) ES2994877T3 (enExample)
MX (2) MX2018001004A (enExample)
WO (1) WO2017019487A1 (enExample)

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EP3250557B1 (en) 2015-01-29 2024-11-20 Signal Pharmaceuticals, LLC Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide
CN107922287B (zh) 2015-07-24 2021-04-09 细胞基因公司 合成(1r,2r,5r)-5-氨基-2-甲基环己醇盐酸盐的方法和其中可用的中间体
CN111848423B (zh) * 2019-04-30 2022-10-14 尚科生物医药(上海)有限公司 3-氧代环丁基氨基甲酸叔丁酯的制备方法

Family Cites Families (80)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2859239A (en) * 1956-08-17 1958-11-04 Dow Chemical Co Acrylic acid compounds
CH549339A (de) 1971-05-12 1974-05-31 Ciba Geigy Ag Herbizides mittel.
US5763647A (en) * 1990-03-30 1998-06-09 Shionogi & Co., Ltd. Preparation of optically active 1,4-bridged-cyclohexane carboxylic acid derivatives
EP0520419A3 (en) * 1991-06-26 1993-06-16 Union Carbide Chemicals & Plastics Technology Corporation Production of unsaturated cycloaliphatic esters and derivatives thereof
WO1999031073A1 (en) 1997-12-15 1999-06-24 Yamanouchi Pharmaceutical Co., Ltd. Novel pyrimidine-5-carboxamide derivatives
EP1107957B1 (en) 1998-08-29 2006-10-18 AstraZeneca AB Pyrimidine compounds
EP1184376B1 (en) 1999-06-09 2005-02-02 Yamanouchi Pharmaceutical Co. Ltd. Novel heterocyclic carboxamide derivatives
WO2000076980A1 (en) 1999-06-10 2000-12-21 Yamanouchi Pharmaceutical Co., Ltd. Novel nitrogen-contaiing heterocyclic derivatives or salts thereof
CA2383546A1 (en) 1999-06-30 2001-01-04 William H. Parsons Src kinase inhibitor compounds
NZ517694A (en) 1999-08-13 2005-03-24 Vertex Pharma Inhibitors of c-Jun N-terminal kinases (JNK) and other protein kinases
TWI329105B (en) 2002-02-01 2010-08-21 Rigel Pharmaceuticals Inc 2,4-pyrimidinediamine compounds and their uses
GB0206215D0 (en) 2002-03-15 2002-05-01 Novartis Ag Organic compounds
JPWO2003082855A1 (ja) 2002-03-28 2005-08-04 協和醗酵工業株式会社 抗炎症剤
CN1665789A (zh) 2002-06-28 2005-09-07 山之内制药株式会社 二氨基嘧啶酰胺衍生物
ATE451104T1 (de) 2002-07-29 2009-12-15 Rigel Pharmaceuticals Inc Verfahren zur behandlung oder pruvention von autoimmunkrankheiten mit 2,4-pyrimidindiamin- verbindungen
WO2004054617A1 (ja) 2002-12-13 2004-07-01 Kyowa Hakko Kogyo Co., Ltd. 中枢疾患の予防および/または治療剤
EP1586551A4 (en) * 2003-01-16 2006-07-26 Toray Finechemicals Co Ltd METHOD FOR OBTAINING OPTICALLY ACTIVE DIACYLTARTIC ACIDS
JP2006516561A (ja) 2003-01-17 2006-07-06 ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー 細胞増殖の阻害剤としての2−アミノピリジン置換ヘテロ環類
EP1590334B1 (en) 2003-01-30 2009-08-19 Boehringer Ingelheim Pharmaceuticals Inc. 2,4-diaminopyrimidine derivatives useful as inhibitors of pkc-theta
DK2287156T3 (da) 2003-08-15 2013-08-26 Novartis Ag 2,4-Di(phenylamino)-pyrimidiner egnede i behandling af neoplastiske sygdomme, inflammatoriske lidelser og lidelser i immunsystemet
EP1663241B1 (en) 2003-09-24 2009-05-27 Wyeth Holdings Corporation 5-arylpyrimidines as anticancer agents
EP1749827A4 (en) 2004-03-30 2010-04-21 Kyowa Hakko Kirin Co Ltd ANTITUMOR AGENTS
JP2008505910A (ja) 2004-07-08 2008-02-28 ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド Pkc−シータのインヒビターとして有用なピリミジン誘導体
JP2008512429A (ja) 2004-09-10 2008-04-24 ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング ロフルミラストとsykインヒビターとの組合せ物並びにその使用方法
CA2579007A1 (en) 2004-09-10 2006-03-16 Altana Pharma Ag Ciclesonide and syk inhibitor combination and methods of use thereof
JP2006124387A (ja) 2004-09-30 2006-05-18 Taisho Pharmaceut Co Ltd 新規なキノリン、テトラヒドロキナゾリン、及びピリミジン誘導体と、これらを使用することに関連した治療方法
EP1797047B1 (en) 2004-09-30 2012-01-25 Tibotec Pharmaceuticals Hiv inhibiting 5-substituted pyrimidines
WO2006091737A1 (en) 2005-02-24 2006-08-31 Kemia, Inc. Modulators of gsk-3 activity
GT200600105A (es) 2005-03-10 2007-02-14 Derivados de pirimidina para el tratamiento de trastornos hiperproliferativos.
WO2007032445A1 (ja) 2005-09-16 2007-03-22 Kyowa Hakko Kogyo Co., Ltd. タンパク質キナーゼ阻害剤
WO2008009458A1 (en) 2006-07-21 2008-01-24 Novartis Ag 2, 4 -di (arylaminio) -pyrimidine-5-carboxamide compounds as jak kinases inhibitors
US8188113B2 (en) 2006-09-14 2012-05-29 Deciphera Pharmaceuticals, Inc. Dihydropyridopyrimidinyl, dihydronaphthyidinyl and related compounds useful as kinase inhibitors for the treatment of proliferative diseases
US20080139531A1 (en) 2006-12-04 2008-06-12 Alcon Manufacturing Ltd. Use of connective tissue mast cell stabilizers to facilitate ocular surface re-epithelization and wound repair
CL2007003693A1 (es) * 2006-12-22 2008-06-27 Actelion Pharmaceuticals Ltd Compuestos derivados de pirido [3,2-b] [1,4] tiazina; composicion farmaceutica que contiene dichos compuestos; y su uso en el tratamiento de infecciones bacterianas.
WO2008129380A1 (en) 2007-04-18 2008-10-30 Pfizer Products Inc. Sulfonyl amide derivatives for the treatment of abnormal cell growth
NZ581397A (en) 2007-04-27 2012-02-24 Astrazeneca Ab Pyrimidine compounds for the inhibition of Eph receptors and for the treatment of cancer
CN101796046A (zh) 2007-07-16 2010-08-04 阿斯利康(瑞典)有限公司 嘧啶衍生物934
WO2009012421A1 (en) 2007-07-17 2009-01-22 Rigel Pharmaceuticals, Inc. Cyclic amine substituted pyrimidinediamines as pkc inhibitors
JP5269444B2 (ja) * 2008-03-11 2013-08-21 東ソー・ファインケム株式会社 固体ルイス酸触媒、それを用いたディールスアルダー付加物の製造方法
CN102066339B (zh) 2008-04-16 2014-09-24 波托拉医药品公司 作为syk或jak蛋白激酶抑制剂的2,6-二氨基-嘧啶-5-基甲酰胺类化合物
CA2960692C (en) 2008-04-16 2019-09-24 Portola Pharmaceuticals, Inc. 2,6-diamino-pyrimidin-5-yl-carboxamides as syk or jak kinase inhibitors
NZ588830A (en) 2008-04-22 2012-11-30 Portola Pharm Inc Inhibitors of protein kinases
CA2719868A1 (en) 2008-04-29 2009-11-05 F. Hoffmann-La Roche Ag Pyrimidinyl pyridone inhibitors of jnk.
PL2300013T5 (pl) 2008-05-21 2025-04-28 Takeda Pharmaceutical Company Limited Pochodne fosforu jako inhibitor kinazy
UY31929A (es) 2008-06-25 2010-01-05 Irm Llc Compuestos y composiciones como inhibidores de cinasa
US8338439B2 (en) 2008-06-27 2012-12-25 Celgene Avilomics Research, Inc. 2,4-disubstituted pyrimidines useful as kinase inhibitors
TWI458721B (zh) 2008-06-27 2014-11-01 Celgene Avilomics Res Inc 雜芳基化合物及其用途
CN102137848A (zh) 2008-09-01 2011-07-27 安斯泰来制药株式会社 2,4-二氨基嘧啶化合物
EP2159220A1 (en) * 2008-09-02 2010-03-03 Nabriva Therapeutics AG Organic compounds
TWI453207B (zh) * 2008-09-08 2014-09-21 Signal Pharm Llc 胺基三唑并吡啶,其組合物及使用其之治療方法
EP2331507A2 (en) 2008-09-18 2011-06-15 Astellas Pharma Inc. Heterocyclic carboxamide compounds
TW201016676A (en) 2008-10-03 2010-05-01 Astrazeneca Ab Heterocyclic derivatives and methods of use thereof
RU2522001C2 (ru) 2008-10-31 2014-07-10 Сентокор Орто Байотек Инк. Дифференцирование человеческих эмбриональных стволовых клеток в линию панкреатических эндокринных клеток
WO2010068863A2 (en) 2008-12-12 2010-06-17 Cystic Fibrosis Foundation Therapeutics, Inc. Pyrimidine compounds and methods of making and using same
WO2010080864A1 (en) 2009-01-12 2010-07-15 Array Biopharma Inc. Piperidine-containing compounds and use thereof
CA2749403A1 (en) 2009-01-13 2010-09-02 Glaxo Group Limited Pyrimidinecarboxamide derivatives as inhibitors of syk kinase
US8377924B2 (en) 2009-01-21 2013-02-19 Rigel Pharmaceuticals Inc. Protein kinase C inhibitors and uses thereof
US8367689B2 (en) 2009-05-06 2013-02-05 Portola Pharmaceuticals, Inc. Inhibitors of JAK
DK2428508T3 (en) 2009-05-08 2016-02-01 Astellas Pharma Inc Diamino heterocyclic carboxamide COMPOUND
JP2012148977A (ja) 2009-05-20 2012-08-09 Astellas Pharma Inc アミノシクロヘキシルアルキル基を有する2,4−ジアミノピリミジン化合物
MX2011013325A (es) 2009-06-10 2012-04-30 Abbott Lab 2-(lh-pirazol-4-ilamino)-pirimidina como inhibidores de cinasa.
JP2012197231A (ja) 2009-08-06 2012-10-18 Oncotherapy Science Ltd Ttk阻害作用を有するピリジンおよびピリミジン誘導体
WO2011065800A2 (ko) 2009-11-30 2011-06-03 주식회사 오스코텍 피리미딘 유도체, 이의 제조방법 및 이를 함유하는 약학적 조성물
CA2780759A1 (en) 2009-12-01 2011-06-09 Rigel Pharmaceuticals, Inc. Protein kinase c inhibitors and uses thereof
JP2013533866A (ja) * 2010-06-17 2013-08-29 ドクター レディズ ラボラトリーズ リミテッド 3−アミノピペリジンジヒドロクロリドの単一の鏡像異性体を調製するための方法
CA2801781C (en) 2010-07-21 2018-02-27 Rigel Pharmaceuticals, Inc. Protein kinase c inhibitors and uses thereof
US8580805B2 (en) 2010-08-31 2013-11-12 Hubert Maehr Pyrimidine carboxamide derivatives
US20130244963A1 (en) 2010-09-30 2013-09-19 Portola Pharmaceuticals, Inc. Combination therapy with 4-(3-(2h-1,2,3-triazol-2-yl)phenylamino)-2-((1r,2s)-2-aminocyclohexylamino)pyrimidine-5-carboxamide
WO2012045010A1 (en) 2010-09-30 2012-04-05 Portola Pharmaceuticals, Inc. Combinations of 4-(3-(2h-1,2,3-triazo-2-yl) phenylamino)-2-((1r,2s)-2-aminocyclohexylamino) pyrimidine-5-carboxamide and fludarabine
SG194086A1 (en) 2011-04-22 2013-11-29 Signal Pharm Llc Substituted diaminocarboxamide and diaminocarbonitrile pyrimidines, compositions thereof, and methods of treatment therewith
WO2014019166A1 (zh) * 2012-08-01 2014-02-06 上海威智医药科技有限公司 高活性硼烷类化合物的工业化生产方法
JP2014031327A (ja) * 2012-08-02 2014-02-20 Kaneka Corp 光学活性シス−2−アミノ−シクロヘキサンカルボン酸誘導体およびその前駆体の製造法
MX2016007898A (es) 2013-12-20 2016-10-07 Signal Pharm Llc Compuestos diaminopirimidilo sustituidos, las composiciones de estos y los metodos de tratamiento con estos.
NZ715903A (en) * 2014-01-30 2017-06-30 Signal Pharm Llc Solid forms of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide, compositions thereof and methods of their use
TWI523838B (zh) * 2014-03-21 2016-03-01 Far Eastern New Century Corp Terephthalic acid and 4-methyl-3-cyclohexene-1-carboxylic acid Ester preparation method
CN113248506A (zh) 2014-10-06 2021-08-13 西格诺药品有限公司 取代的氨基嘌呤化合物、其组合物及其治疗方法
SG11201704827UA (en) 2014-12-16 2017-07-28 Signal Pharm Llc Formulations of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methycyclohexylamino)-pyrimidine-5-carboxamide
WO2016100308A1 (en) 2014-12-16 2016-06-23 Signal Pharmaceuticals, Llc Methods for measurement of inhibition of c-jun n-terminal kinase in skin
EP3250557B1 (en) 2015-01-29 2024-11-20 Signal Pharmaceuticals, LLC Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide
CN107922287B (zh) * 2015-07-24 2021-04-09 细胞基因公司 合成(1r,2r,5r)-5-氨基-2-甲基环己醇盐酸盐的方法和其中可用的中间体

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JP2021046426A (ja) 2021-03-25
EP3795553B1 (en) 2024-05-15
CN107922287A (zh) 2018-04-17
ES2994877T3 (en) 2025-02-03
CA2993173A1 (en) 2017-02-02
CN107922287B (zh) 2021-04-09
JP2018521085A (ja) 2018-08-02
MX2018001004A (es) 2018-06-07
EP3325432A1 (en) 2018-05-30
US10252981B2 (en) 2019-04-09
AU2021201493B2 (en) 2022-07-14
AU2021201493A1 (en) 2021-03-25
US11192847B2 (en) 2021-12-07
HK1255553A1 (en) 2019-08-23
US20220234990A1 (en) 2022-07-28
JP7165178B2 (ja) 2022-11-02
EP3795553A1 (en) 2021-03-24
AU2016297784A1 (en) 2018-02-08
US10774033B2 (en) 2020-09-15
MX385379B (es) 2025-03-18
AU2016297784B2 (en) 2020-12-24
EP3325432B1 (en) 2020-09-02
CA3208587A1 (en) 2017-02-02
US20190152893A1 (en) 2019-05-23
MX2020001720A (es) 2021-08-13
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EP3325432A4 (en) 2019-04-24
CA2993173C (en) 2023-10-03
US20180215700A1 (en) 2018-08-02
US11780801B2 (en) 2023-10-10
WO2017019487A1 (en) 2017-02-02
US20200369600A1 (en) 2020-11-26

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