MX369956B - Metodos para preparar compuestos de benzoquinolina. - Google Patents

Metodos para preparar compuestos de benzoquinolina.

Info

Publication number
MX369956B
MX369956B MX2016007056A MX2016007056A MX369956B MX 369956 B MX369956 B MX 369956B MX 2016007056 A MX2016007056 A MX 2016007056A MX 2016007056 A MX2016007056 A MX 2016007056A MX 369956 B MX369956 B MX 369956B
Authority
MX
Mexico
Prior art keywords
tetrabenazine
methods
deuterated
manufacturing
vmat2
Prior art date
Application number
MX2016007056A
Other languages
English (en)
Other versions
MX2016007056A (es
Inventor
Zhang Chengzhi
Original Assignee
Auspex Pharmaceuticals 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 Auspex Pharmaceuticals Inc filed Critical Auspex Pharmaceuticals Inc
Publication of MX2016007056A publication Critical patent/MX2016007056A/es
Publication of MX369956B publication Critical patent/MX369956B/es

Links

Classifications

    • 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

Landscapes

  • 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)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La presenta invención se refiere a nuevos métodos para preparar inhibidores de benzoquinolina del transportador 2 de monoamina vesicular (VMAT2), e intermediarios de los mismos. Se describen en la presente métodos novedosos para preparar compuestos de benzoquinolina de la fórmula (I), incluyendo tetrabenazina y análogos de tetrabenazina deuterados tal como d6-tetrabenazina. La tetrabenazina es un inhibidor de transportador 2 de monoamina vesicular (VMAT2) y se prescribe comúnmente para el tratamiento de enfermedad de Huntington. La d6-Tetrabenazina es un análogo deuterado de tetrabenazina que tiene propiedades farmacocinéticas mejoradas cuando se compara con el fármaco no deuterado y está actualmente bajo desarrollo clínico.
MX2016007056A 2013-12-03 2014-11-24 Metodos para preparar compuestos de benzoquinolina. MX369956B (es)

Applications Claiming Priority (2)

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

Publications (2)

Publication Number Publication Date
MX2016007056A MX2016007056A (es) 2017-01-06
MX369956B true MX369956B (es) 2019-11-27

Family

ID=53264424

Family Applications (1)

Application Number Title Priority Date Filing Date
MX2016007056A MX369956B (es) 2013-12-03 2014-11-24 Metodos para preparar compuestos de benzoquinolina.

Country Status (14)

Country Link
US (8) US20150152099A1 (es)
EP (2) EP3424504A1 (es)
JP (1) JP6542222B2 (es)
KR (1) KR102391134B1 (es)
CN (1) CN105873589B (es)
AU (4) AU2014357518A1 (es)
BR (1) BR112016012747B1 (es)
CA (1) CA2930744A1 (es)
EA (2) EA032920B1 (es)
HK (2) HK1223020A1 (es)
IL (1) IL245539B (es)
MX (1) MX369956B (es)
NZ (1) NZ720301A (es)
WO (1) WO2015084622A1 (es)

Families Citing this family (12)

* 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
US9346800B2 (en) 2012-09-18 2016-05-24 Auspex Pharmaceuticals, Inc. Formulations pharmacokinetics of deuterated benzoquinoline inhibitors of vesicular monoamine transporter 2
JP6542222B2 (ja) 2013-12-03 2019-07-10 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 ベンゾキノリン化合物の製造方法
KR20240049625A (ko) 2015-03-06 2024-04-16 오스펙스 파마슈티칼스, 인코포레이티드 비정상적 불수의 운동 장애의 치료 방법
US10479787B2 (en) * 2016-04-22 2019-11-19 Lupin Limited Process for preparation of tetrabenazine and deutetrabenazine
US10703750B2 (en) 2017-01-10 2020-07-07 Sandoz Ag Crystalline valbenazine free base
US10954235B2 (en) 2017-02-27 2021-03-23 Sandoz Ag Crystalline forms of valbenazine salts
BR112019018966A2 (pt) * 2017-03-15 2020-04-22 Auspex Pharmaceuticals Inc analógicos da deutetrabenazina, sua preparação e uso
WO2019130252A2 (en) * 2017-12-29 2019-07-04 Mylan Laboratories Ltd Methods and intermediates for preparing deutetrabenazine
WO2019150387A1 (en) * 2018-02-01 2019-08-08 Alaparthi Lakshmi Prasad A novel process for preparation of deutetrabenazine
TW202033521A (zh) * 2018-10-24 2020-09-16 美商紐羅克里生物科學有限公司 製備囊泡單胺轉運蛋白2(vmat2)抑制劑之方法
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
US2830993A (en) 1958-04-15 Quinolizine derivatives
US2843591A (en) 1958-07-15 Method for preparing same
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
KR20040068613A (ko) 1994-03-25 2004-07-31 이소테크니카 인코포레이티드 중수소화된 화합물 이를 포함하는 고혈압 치료용 조성물
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
ES2193921T3 (es) 1999-12-03 2003-11-16 Pfizer Prod Inc Compuestos de sulfamoilheteroaril-pirazol como agentes antinflamatorios/analgesicos.
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
PL1638529T3 (pl) 2003-06-16 2017-03-31 Andrx Pharmaceuticals, Llc. Kompozycja doustna o przedłużonym uwalnianiu
JP2007512338A (ja) 2003-11-21 2007-05-17 メモリー・ファーマシューティカルズ・コーポレイション Ｌ型カルシウムチャンネルブロッカーとコリンエステラーゼ阻害剤を用いた組成物及び処置方法
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
BRPI0606318B8 (pt) 2005-01-19 2021-05-25 Rigel Pharmaceuticals Inc composto, composição, e, uso de um composto
US20070148238A1 (en) 2005-06-23 2007-06-28 Spherics, Inc. 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
EA017983B1 (ru) 2006-02-17 2013-04-30 Бедс Фарма Гмбх Беролина Инновейтив Ресёч Энд Девелопмент Сёвисиз Дейтерированные производные катехоламина и лекарственные средства, содержащие указанные соединения
MX2008014064A (es) 2006-05-02 2009-06-12 Univ Pennsylvania Derivados radiomarcados de dihidrotetrabenazina y su uso como agentes de diagnostico por imagenes.
HU227610B1 (en) 2006-09-18 2011-09-28 Richter Gedeon Nyrt Pharmaceutical compositions containing rosuvastatin potassium
WO2008043797A1 (en) 2006-10-12 2008-04-17 Novartis Ag Use of modified cyclosporins
BRPI0718247B1 (pt) 2006-11-08 2021-09-21 Neurocrine Biosciences, Inc. Composto usado como inibidor do transportador de monoamina vesicular 2, composição farmacêutica compreendendo o dito composto e uso da dita composição farmacêutica no tratamento de transtornos hipercinéticos
ATE540041T1 (de) 2006-11-21 2012-01-15 Rigel Pharmaceuticals Inc Prodrug-salze von 2,4-pyrimidindiaminverbindungen und anwendungen davon
US20100204258A1 (en) 2007-03-12 2010-08-12 The Trustees Of Columbia University In The City Of New York Methods and compositions for modulating insulin secretion and glucose metabolism
US7897768B2 (en) * 2007-06-08 2011-03-01 General Electric Company Method for making tetrabenazine compounds
KR101760139B1 (ko) 2007-06-29 2017-07-31 클라렌슈 피티와이 리미티드 안투여를 통한 신경 또는 신경정신 장애의 치료 또는 예방용 약학 조성물
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
WO2009126305A1 (en) 2008-04-11 2009-10-15 The Trustees Of Columbia University 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
WO2010002972A1 (en) 2008-07-01 2010-01-07 Curemark, Llc Methods and compositions for the treatment of symptoms of neurological and mental health disorders
DE102008040212A1 (de) 2008-07-07 2010-01-14 Zf Friedrichshafen Ag Radaufhängung für ein Fahrzeug
US20110053866A1 (en) 2008-08-12 2011-03-03 Biovail Laboratories International (Barbados) S.R.L. Pharmaceutical compositions
GB2462611A (en) 2008-08-12 2010-02-17 Cambridge Lab Pharmaceutical composition comprising tetrabenazine
BRPI0913457B8 (pt) 2008-09-18 2021-08-31 Auspex Pharmaceutical Inc Composto e composição farmacêutica
US20100113496A1 (en) 2008-09-25 2010-05-06 Auspex Pharmaceuticals, Inc. Piperidine modulators of vmat2
WO2010093434A1 (en) 2009-02-11 2010-08-19 Celgene Corporation 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
CA2790199A1 (en) 2010-02-24 2011-09-01 Auspex Pharmaceuticals, Inc. Trimethoxyphenyl inhibitors of tyrosine kinase
US20110206782A1 (en) 2010-02-24 2011-08-25 Auspex Pharmaceuticals, Inc. Piperidine modulators of dopamine receptor
CN104744456A (zh) 2010-06-01 2015-07-01 奥斯拜客斯制药有限公司 Vmat2的苯并喹啉酮抑制剂
US9676810B2 (en) 2010-07-08 2017-06-13 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
WO2013142816A1 (en) 2012-03-23 2013-09-26 Cardero Therapeutics, Inc. Compounds and compositions for the treatment of muscular disorders
US9346800B2 (en) 2012-09-18 2016-05-24 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
EA201500801A1 (ru) 2013-01-31 2016-01-29 Ауспекс Фармацетикалс, Инк. Бензохинолоновые ингибиторы vmat2
WO2015048370A1 (en) 2013-09-27 2015-04-02 Auspex Pharmaceuticals, Inc. Benzoquinolone inhibitors of vmat2
WO2015077521A1 (en) 2013-11-22 2015-05-28 Auspex Pharmaceuticals, Inc. Benzoquinoline inhibitors of vesicular monoamine transporter 2
JP2017503756A (ja) 2013-11-22 2017-02-02 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 異常な筋活動を処置する方法
JP6542222B2 (ja) 2013-12-03 2019-07-10 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 ベンゾキノリン化合物の製造方法
MX2016009817A (es) 2014-01-27 2017-02-28 Auspex Pharmaceuticals Inc Inhibidores de benzoquinolina del transportador vesicular de monoaminas 2.

Also Published As

Publication number Publication date
US12077487B2 (en) 2024-09-03
IL245539A0 (en) 2016-06-30
HK1223020A1 (zh) 2017-07-21
AU2014357518A1 (en) 2016-06-09
EA032920B1 (ru) 2019-08-30
EA201791466A1 (ru) 2017-11-30
JP2017501141A (ja) 2017-01-12
EP3424504A1 (en) 2019-01-09
US20170190654A1 (en) 2017-07-06
NZ720301A (en) 2022-01-28
EP3076970A4 (en) 2017-07-26
MX2016007056A (es) 2017-01-06
US20170197957A1 (en) 2017-07-13
HK1224222A1 (zh) 2017-08-18
US20230060294A1 (en) 2023-03-02
US20180230083A1 (en) 2018-08-16
AU2020201091B2 (en) 2021-04-29
EA201691162A1 (ru) 2016-11-30
US20200331846A1 (en) 2020-10-22
US10513488B2 (en) 2019-12-24
KR102391134B1 (ko) 2022-04-28
CN105873589A (zh) 2016-08-17
CA2930744A1 (en) 2015-06-11
JP6542222B2 (ja) 2019-07-10
AU2023203246A1 (en) 2023-06-15
KR20160087904A (ko) 2016-07-22
BR112016012747B1 (pt) 2022-07-12
CN105873589B (zh) 2019-11-01
WO2015084622A1 (en) 2015-06-11
US20150152099A1 (en) 2015-06-04
US20190092719A1 (en) 2019-03-28
BR112016012747A2 (es) 2017-08-08
US20200347008A1 (en) 2020-11-05
IL245539B (en) 2021-06-30
EP3076970A1 (en) 2016-10-12
AU2021209150A1 (en) 2021-08-19
AU2020201091A1 (en) 2020-03-05

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