JP6542222B2 - ベンゾキノリン化合物の製造方法 - Google Patents

ベンゾキノリン化合物の製造方法 Download PDF

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JP6542222B2
JP6542222B2 JP2016536571A JP2016536571A JP6542222B2 JP 6542222 B2 JP6542222 B2 JP 6542222B2 JP 2016536571 A JP2016536571 A JP 2016536571A JP 2016536571 A JP2016536571 A JP 2016536571A JP 6542222 B2 JP6542222 B2 JP 6542222B2
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certain embodiments
acid
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formula
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JP2017501141A5 (enExample
JP2017501141A (ja
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チェンジ・ジャン
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オースペックス ファーマシューティカルズ インコーポレイテッド
オースペックス ファーマシューティカルズ インコーポレイテッド
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/001—Acyclic or carbocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/002—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C223/00—Compounds containing amino and —CHO groups bound to the same carbon skeleton
    • C07C223/02—Compounds containing amino and —CHO groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
    • C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
JP2016536571A 2013-12-03 2014-11-24 ベンゾキノリン化合物の製造方法 Active JP6542222B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361911214P 2013-12-03 2013-12-03
US61/911,214 2013-12-03
PCT/US2014/067117 WO2015084622A1 (en) 2013-12-03 2014-11-24 Methods of manufacturing benzoquinoline compounds

Publications (3)

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JP2017501141A JP2017501141A (ja) 2017-01-12
JP2017501141A5 JP2017501141A5 (enExample) 2018-01-11
JP6542222B2 true JP6542222B2 (ja) 2019-07-10

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JP2016536571A Active JP6542222B2 (ja) 2013-12-03 2014-11-24 ベンゾキノリン化合物の製造方法

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US (8) US20150152099A1 (enExample)
EP (2) EP3076970A4 (enExample)
JP (1) JP6542222B2 (enExample)
KR (1) KR102391134B1 (enExample)
CN (1) CN105873589B (enExample)
AU (4) AU2014357518A1 (enExample)
BR (1) BR112016012747B1 (enExample)
CA (1) CA2930744A1 (enExample)
EA (2) EA032920B1 (enExample)
HK (1) HK1224222A1 (enExample)
IL (1) IL245539B (enExample)
MX (1) MX369956B (enExample)
NZ (1) NZ720301A (enExample)
WO (1) WO2015084622A1 (enExample)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9550780B2 (en) 2012-09-18 2017-01-24 Auspex Pharmaceuticals, Inc. Formulations pharmacokinetics of deuterated benzoquinoline inhibitors of vesicular monoamine transporter 2
CA2883641C (en) 2012-09-18 2021-09-14 Auspex Pharmaceuticals, Inc. Formulations pharmacokinetics of deuterated benzoquinoline inhibitors of vesicular monoamine transporter 2
CN105873589B (zh) 2013-12-03 2019-11-01 奥斯拜客斯制药有限公司 制造苯并喹啉化合物的方法
CN114767672A (zh) 2015-03-06 2022-07-22 奥斯拜客斯制药有限公司 氘代丁苯那嗪或包含氘代丁苯那嗪的组合物
US10479787B2 (en) * 2016-04-22 2019-11-19 Lupin Limited Process for preparation of tetrabenazine and deutetrabenazine
WO2018130345A1 (en) 2017-01-10 2018-07-19 Sandoz Ag Crystalline valbenazine free base
CA3054238A1 (en) 2017-02-27 2018-08-30 Sandoz Ag Crystalline forms of valbenazine salts
US11813232B2 (en) 2017-03-15 2023-11-14 Auspex Pharmaceuticals, Inc. Analogs of deutetrabenazine, their preparation and use
WO2019130252A2 (en) * 2017-12-29 2019-07-04 Mylan Laboratories Ltd Methods and intermediates for preparing deutetrabenazine
US11505549B2 (en) * 2018-02-01 2022-11-22 Lakshmi Prasad ALAPARTHI Process for preparation of Deutetrabenazine
JP7603199B2 (ja) 2018-10-18 2024-12-20 オンコペプティデス・イノベーション・エービー 重水素を含有する化合物
WO2020086765A1 (en) * 2018-10-24 2020-04-30 Neurocrine Biosciences, Inc. Processes for preparing a vmat2 inhibitor
CN111960999B (zh) * 2020-07-20 2021-11-02 暨明医药科技（苏州）有限公司 一种丁苯那嗪中间体的合成方法

Family Cites Families (70)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2843591A (en) 1958-07-15 Method for preparing same
US2830993A (en) 1958-04-15 Quinolizine derivatives
US2326643A (en) 1941-08-20 1943-08-10 Rohm & Haas Complex polyamino sulphur compound
US3045021A (en) 1959-09-24 1962-07-17 Hoffmann La Roche Preparation of substituted 2-oxobenzoquinolizines
GB999095A (en) * 1961-02-21 1965-07-21 Wellcome Found The preparation of quinolizine derivatives
HU175890B (en) 1977-06-15 1980-11-28 Chinoin Gyogyszer Es Vegyeszet Process for producing new 1,2,3,4,6,7-hexahydro-11-b-alpha-benzo-square bracket-a-square brecket closed-quinolyzine derivatives
US4316897A (en) 1980-09-10 1982-02-23 Hoffmann-La Roche Inc. Method of lowering serum prolactin
DE3407955A1 (de) 1984-03-03 1985-09-05 Dr. Karl Thomae Gmbh, 7950 Biberach Arzneimittel, enthaltend quartaere 3,4-dihydroisochinoliniumsalze
US5451409A (en) 1993-11-22 1995-09-19 Rencher; William F. Sustained release matrix system using hydroxyethyl cellulose and hydroxypropyl cellulose polymer blends
US6221335B1 (en) 1994-03-25 2001-04-24 Isotechnika, Inc. Method of using deuterated calcium channel blockers
CN1087725C (zh) 1994-03-25 2002-07-17 同位素技术有限公司 用氘代方法增强药物效果
GB9817028D0 (en) 1998-08-05 1998-09-30 Smithkline Beecham Plc Novel compounds
US6440710B1 (en) 1998-12-10 2002-08-27 The Scripps Research Institute Antibody-catalyzed deuteration, tritiation, dedeuteration or detritiation of carbonyl compounds
DK1104760T3 (da) 1999-12-03 2003-06-30 Pfizer Prod Inc Sulfamoylheteroarylpyrazolforbindelser som anti-inflammatoriske/analgetiske midler
EP1134290A3 (en) 2000-03-14 2004-01-02 Pfizer Products Inc. Pharmacophore models for the identification of the CYP2D6 inhibitory potency of selective serotonin reuptake inhibitors
US6488962B1 (en) 2000-06-20 2002-12-03 Depomed, Inc. Tablet shapes to enhance gastric retention of swellable controlled-release oral dosage forms
US6287599B1 (en) 2000-12-20 2001-09-11 Shire Laboratories, Inc. Sustained release pharmaceutical dosage forms with minimized pH dependent dissolution profiles
CA2409552A1 (en) 2001-10-25 2003-04-25 Depomed, Inc. Gastric retentive oral dosage form with restricted drug release in the lower gastrointestinal tract
TW200413273A (en) 2002-11-15 2004-08-01 Wako Pure Chem Ind Ltd Heavy hydrogenation method of heterocyclic rings
CA2673334C (en) 2003-06-16 2013-11-12 Andrx Pharmaceuticals, Llc Oral extended-release composition
ES2309594T3 (es) 2003-11-21 2008-12-16 Memory Pharmaceuticals Corporation Composiciones que contienen bloqueadores de los canales de calcio de tipo l e inhibidores de la colinesterasa.
US7367953B2 (en) 2003-11-26 2008-05-06 Ge Medical Systems Global Technology Company Method and system for determining a period of interest using multiple inputs
GB2410947B (en) 2004-02-11 2008-09-17 Cambridge Lab Ltd Pharmaceutical compounds
WO2006053067A2 (en) 2004-11-09 2006-05-18 Prestwick Pharmaceuticals, Inc. Combination of amantadine and a tetrabenazine compound for treating hyperkinetic disorders
JP4801096B2 (ja) 2005-01-19 2011-10-26 ライジェル ファーマシューティカルズ， インコーポレイテッド ２，４−ピリミジンジアミン化合物のプロドラッグおよびそれらの使用
AU2006261893A1 (en) 2005-06-23 2007-01-04 Combinatorx, Incorporated Improved dosage forms for movement disorder treatment
US20080033011A1 (en) 2005-07-29 2008-02-07 Concert Pharmaceuticals Inc. Novel benzo[d][1,3]-dioxol derivatives
US7750168B2 (en) 2006-02-10 2010-07-06 Sigma-Aldrich Co. Stabilized deuteroborane-tetrahydrofuran complex
BRPI0708071A8 (pt) 2006-02-17 2017-12-26 Birds Pharma Gmbh Berolina Innovative Res & Development Services Derivados de catecolamina deuterada e medicamentos compreendendo os ditos compostos
BRPI0711481A8 (pt) 2006-05-02 2017-11-28 Univ Michigan Regents derivados radiomarcados de dihidrotetrabenzeno e seu uso como agente de imagens
HU227610B1 (en) 2006-09-18 2011-09-28 Richter Gedeon Nyrt Pharmaceutical compositions containing rosuvastatin potassium
BRPI0719189A2 (pt) 2006-10-12 2018-08-14 Univ Kyushu Nat Univ Corp uso de ciclosporinas modificadas
DK2081929T3 (da) * 2006-11-08 2013-04-15 Neurocrine Biosciences Inc Substituerede 3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11B-hexahydro-2H-pyrido[2,1-A]isoquinolin-2-ol-forbindelser og fremgangsmåder angående disse
ES2380551T3 (es) 2006-11-21 2012-05-16 Rigel Pharmaceuticals, Inc. Sales de profármaco de compuestos de 2,4-pirimidindiamina y sus usos
WO2008112278A2 (en) 2007-03-12 2008-09-18 The Trustees Of Columbia University In The City Of New York Methods and compositions for modulating insulin secretion and glucose metabolism
US8008500B2 (en) 2007-06-08 2011-08-30 General Electric Company Intermediates useful for making tetrabenazine compounds
DK2173344T3 (en) 2007-06-29 2016-07-25 Clarencew Pty Ltd TREATMENT OR PROPHYLAXIS OF NEUROLOGICAL OR NEURO PSYCHIATRIC DISORDERS USING ocular administration
US8053578B2 (en) 2007-11-29 2011-11-08 General Electric Company Alpha-fluoroalkyl dihydrotetrabenazine imaging agents and probes
US7902364B2 (en) 2007-11-29 2011-03-08 General Electric Company Alpha-fluoroalkyl tetrabenazine and dihydrotetrabenazine imaging agents and probes
WO2009124357A1 (en) 2008-04-10 2009-10-15 Malvin Leonard Eutick Fast dissolving oral formulations for critical drugs
US9012471B2 (en) 2008-04-11 2015-04-21 The Trustees Of Columbia University In The City Of New York Glucose metabolism modulating compounds
CN201204923Y (zh) 2008-04-14 2009-03-11 云南省烟草公司昆明市公司 鲜烟叶编叶机
ES2732453T3 (es) 2008-07-01 2019-11-22 Curemark Llc Métodos y composiciones para el tratamiento de síntomas de trastornos neurológicos y de salud mental
DE102008040212A1 (de) 2008-07-07 2010-01-14 Zf Friedrichshafen Ag Radaufhängung für ein Fahrzeug
GB2462611A (en) 2008-08-12 2010-02-17 Cambridge Lab Pharmaceutical composition comprising tetrabenazine
US20110053866A1 (en) 2008-08-12 2011-03-03 Biovail Laboratories International (Barbados) S.R.L. Pharmaceutical compositions
CA2736409C (en) 2008-09-18 2017-07-11 Auspex Pharmaceutical, Inc. Benzoquinoline inhibitors of vesicular monoamine transporter 2
US20100113496A1 (en) 2008-09-25 2010-05-06 Auspex Pharmaceuticals, Inc. Piperidine modulators of vmat2
US20120053159A1 (en) 2009-02-11 2012-03-01 Muller George W Isotopologues of lenalidomide
JP2013501810A (ja) 2009-08-12 2013-01-17 ヴァリーント インターナショナル（バルバドス）エスアールエル 医薬組成物
JP4679658B2 (ja) 2009-10-10 2011-04-27 株式会社オーバル フィールド機器の光電センシング感度調整
CN102120742B (zh) 2010-01-08 2013-03-13 中国药科大学 一种丁苯那嗪的制备方法
US20110206782A1 (en) 2010-02-24 2011-08-25 Auspex Pharmaceuticals, Inc. Piperidine modulators of dopamine receptor
CA2790199A1 (en) 2010-02-24 2011-09-01 Auspex Pharmaceuticals, Inc. Trimethoxyphenyl inhibitors of tyrosine kinase
CA2801061A1 (en) * 2010-06-01 2011-12-08 Auspex Pharmaceuticals, Inc. Benzoquinolone inhibitors of vmat2
WO2012006551A2 (en) 2010-07-08 2012-01-12 The Brigham And Women's Hospital, Inc. Neuroprotective molecules and methods of treating neurological disorders and inducing stress granules
WO2012079022A1 (en) 2010-12-10 2012-06-14 Concert Pharmaceuticals, Inc. Substituted dioxopiperidinyl phthalimide derivatives
WO2012081031A1 (en) 2010-12-15 2012-06-21 Enaltec Labs Pvt. Ltd. Process for preparing tetrabenazine
CN102260255B (zh) 2011-07-07 2013-07-10 江苏省原子医学研究所 一种9,10-二甲氧基-1,3,4,6,7,11b-六氢-3-异丁基-2H-苯并[a]喹嗪-2-酮的简便合成方法
WO2013061161A2 (en) 2011-10-28 2013-05-02 Green Bcn Consulting Services Sl New combination therapies for treating neurological disorders
KR101362482B1 (ko) 2012-01-31 2014-02-12 한국과학기술연구원 테트라베나진과 다이하이드로테트라베나진의 제조방법
US9901564B2 (en) 2012-03-23 2018-02-27 Cardero Therapeutics, Inc. Compounds and compositions for the treatment of muscular disorders
CA2883641C (en) 2012-09-18 2021-09-14 Auspex Pharmaceuticals, Inc. Formulations pharmacokinetics of deuterated benzoquinoline inhibitors of vesicular monoamine transporter 2
CN102936246A (zh) * 2012-11-08 2013-02-20 江苏暨明医药科技有限公司 丁苯那嗪的合成方法
WO2014120654A1 (en) 2013-01-31 2014-08-07 Auspex Pharmaceuticals, Inc. Benzoquinolone inhibitors of vmat2
HK1221645A1 (zh) 2013-09-27 2017-06-09 Auspex Pharmaceuticals, Inc. Vmat2的苯并喹啉抑制剂
WO2015077521A1 (en) 2013-11-22 2015-05-28 Auspex Pharmaceuticals, Inc. Benzoquinoline inhibitors of vesicular monoamine transporter 2
WO2015077520A1 (en) 2013-11-22 2015-05-28 Auspex Pharmaceuticals, Inc. Methods of treating abnormal muscular activity
CN105873589B (zh) 2013-12-03 2019-11-01 奥斯拜客斯制药有限公司 制造苯并喹啉化合物的方法
CA2936823A1 (en) 2014-01-27 2015-07-30 Auspex Pharmaceuticals, Inc. Benzoquinoline inhibitors of vesicular monoamine transporter 2

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IL245539B (en) 2021-06-30
BR112016012747B1 (pt) 2022-07-12
EA201791466A1 (ru) 2017-11-30
AU2023203246A1 (en) 2023-06-15
AU2021209150A1 (en) 2021-08-19
AU2020201091B2 (en) 2021-04-29
EP3076970A4 (en) 2017-07-26
US20170190654A1 (en) 2017-07-06
EP3424504A1 (en) 2019-01-09
CA2930744A1 (en) 2015-06-11
AU2023203246B2 (en) 2025-02-27
US20230060294A1 (en) 2023-03-02
KR20160087904A (ko) 2016-07-22
US12077487B2 (en) 2024-09-03
EA201691162A1 (ru) 2016-11-30
HK1224222A1 (zh) 2017-08-18
US20190092719A1 (en) 2019-03-28
EA032920B1 (ru) 2019-08-30
HK1223020A1 (zh) 2017-07-21
BR112016012747A2 (enExample) 2017-08-08
WO2015084622A1 (en) 2015-06-11
CN105873589B (zh) 2019-11-01
US20200347008A1 (en) 2020-11-05
CN105873589A (zh) 2016-08-17
MX2016007056A (es) 2017-01-06
US20170197957A1 (en) 2017-07-13
US20180230083A1 (en) 2018-08-16
US20200331846A1 (en) 2020-10-22
MX369956B (es) 2019-11-27
AU2020201091A1 (en) 2020-03-05
JP2017501141A (ja) 2017-01-12
AU2014357518A1 (en) 2016-06-09
US10513488B2 (en) 2019-12-24
IL245539A0 (en) 2016-06-30
NZ720301A (en) 2022-01-28
KR102391134B1 (ko) 2022-04-28
EP3076970A1 (en) 2016-10-12
US20150152099A1 (en) 2015-06-04

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