CA3079071C - Preparation of crystallized benzimidazole derivative as mek inhibitor and formulation comprising same - Google Patents

Preparation of crystallized benzimidazole derivative as mek inhibitor and formulation comprising same Download PDF

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Publication number
CA3079071C
CA3079071C CA3079071A CA3079071A CA3079071C CA 3079071 C CA3079071 C CA 3079071C CA 3079071 A CA3079071 A CA 3079071A CA 3079071 A CA3079071 A CA 3079071A CA 3079071 C CA3079071 C CA 3079071C
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Prior art keywords
compound
formula
mixture
solution
water
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CA3079071A
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English (en)
French (fr)
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CA3079071A1 (en
Inventor
Christoph Max Krell
Marian Misun
Daniel Andreas Niederer
Werner Heinz Pachinger
Marie-Christine Wolf
Daniel Zimmerman
Weidong Liu
Peter J. Stengel
Paul Nichols
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Array Biopharma Inc
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Array Biopharma Inc
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Publication of CA3079071A1 publication Critical patent/CA3079071A1/en
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • 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
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/41641,3-Diazoles
    • A61K31/41841,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/02Inorganic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12Carboxylic acids; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38Cellulose; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0053Mouth and digestive tract, i.e. intraoral and peroral administration
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2009Inorganic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2013Organic compounds, e.g. phospholipids, fats
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2013Organic compounds, e.g. phospholipids, fats
    • A61K9/2018Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2022Organic macromolecular compounds
    • A61K9/205Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08Radicals containing only hydrogen and carbon atoms
    • CCHEMISTRY; METALLURGY
    • C30CRYSTAL GROWTH
    • C30BSINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
    • C30B29/00Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
    • C30B29/54Organic compounds
    • CCHEMISTRY; METALLURGY
    • C30CRYSTAL GROWTH
    • C30BSINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
    • C30B7/00Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions
    • C30B7/08Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions by cooling of the solution
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13Crystalline forms, e.g. polymorphs

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biophysics (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Metallurgy (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials Engineering (AREA)
  • Biochemistry (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA3079071A 2012-10-19 2013-10-18 Preparation of crystallized benzimidazole derivative as mek inhibitor and formulation comprising same Active CA3079071C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261716169P 2012-10-19 2012-10-19
US61/716,169 2012-10-19
CA2888474A CA2888474C (en) 2012-10-19 2013-10-18 Preparation of and formulation comprising a mek inhibitor

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA2888474A Division CA2888474C (en) 2012-10-19 2013-10-18 Preparation of and formulation comprising a mek inhibitor

Publications (2)

Publication Number Publication Date
CA3079071A1 CA3079071A1 (en) 2014-04-24
CA3079071C true CA3079071C (en) 2022-06-07

Family

ID=50488781

Family Applications (2)

Application Number Title Priority Date Filing Date
CA3079071A Active CA3079071C (en) 2012-10-19 2013-10-18 Preparation of crystallized benzimidazole derivative as mek inhibitor and formulation comprising same
CA2888474A Active CA2888474C (en) 2012-10-19 2013-10-18 Preparation of and formulation comprising a mek inhibitor

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2888474A Active CA2888474C (en) 2012-10-19 2013-10-18 Preparation of and formulation comprising a mek inhibitor

Country Status (23)

Country Link
US (7) US9238627B2 (enExample)
EP (3) EP3702351B1 (enExample)
JP (3) JP6385939B2 (enExample)
CN (3) CN109456272A (enExample)
AR (1) AR099630A1 (enExample)
BR (1) BR112015008623B1 (enExample)
CA (2) CA3079071C (enExample)
CY (1) CY1122670T1 (enExample)
DK (2) DK2909182T3 (enExample)
ES (2) ES2971077T3 (enExample)
FI (1) FI3702351T3 (enExample)
HR (1) HRP20240033T1 (enExample)
HU (2) HUE065433T2 (enExample)
JO (1) JOP20130304B1 (enExample)
LT (1) LT3702351T (enExample)
PL (2) PL3702351T3 (enExample)
PT (2) PT2909182T (enExample)
RS (1) RS65117B1 (enExample)
RU (2) RU2669391C2 (enExample)
SI (2) SI2909182T1 (enExample)
SM (1) SMT202400044T1 (enExample)
TW (1) TWI650316B (enExample)
WO (1) WO2014063024A1 (enExample)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SI2909182T1 (sl) 2012-10-19 2020-03-31 Array Biopharma Inc. Priprava inhibitorja MEK in formulacije, ki obsegajo inhibitor MEK
CN105566225A (zh) * 2015-02-16 2016-05-11 苏州晶云药物科技有限公司 一种口服丝裂原活化蛋白激酶抑制剂的晶型及其制备方法
UA125436C2 (uk) 2016-06-03 2022-03-09 Еррей Біофарма, Інк. Фармацевтичні комбінації
CN111646946A (zh) * 2017-11-14 2020-09-11 深圳市塔吉瑞生物医药有限公司 一种取代的苯并咪唑化合物及包含该化合物的组合物
TW201938165A (zh) 2017-12-18 2019-10-01 美商輝瑞股份有限公司 治療癌症的方法及組合療法
US11395823B2 (en) * 2018-01-09 2022-07-26 Duke University Topical administration of MEK inhibiting agents for the treatment of skin disorders
WO2020212832A1 (en) * 2019-04-16 2020-10-22 Alembic Pharmaceuticals Limited Process of preparation of benzimidazole compounds
WO2021116901A1 (en) * 2019-12-09 2021-06-17 Biocon Limited Forms of binimetinib and process for preparation thereof
AU2021358394A1 (en) 2020-10-05 2023-04-13 Pierre Fabre Medicament Combination of encorafenib and binimetinib as adjuvant treatment for resected stage II melanoma
CN112679438A (zh) * 2020-12-31 2021-04-20 武汉九州钰民医药科技有限公司 制备司美替尼的方法
JP2024521788A (ja) 2021-05-27 2024-06-04 ミラティ セラピューティクス, インコーポレイテッド 併用療法
WO2023084489A1 (en) 2021-11-15 2023-05-19 Pfizer Inc. Methods of treating coronavirus disease 2019
WO2023131976A1 (en) * 2022-01-06 2023-07-13 Msn Laboratories Private Limited, R&D Center Improved process for the preparation of 5-[(4-bromo-2-fluorophenyl)amino]-4-fluoro-n-(2hydroxyethoxy)-1-methyl-1h-benzimidazole-6-carboxamide
WO2024003942A1 (en) * 2022-07-01 2024-01-04 Natco Pharma Limited An improved process for the preparation of selumetinib sulfate
TW202508595A (zh) 2023-05-04 2025-03-01 美商銳新醫藥公司 用於ras相關疾病或病症之組合療法
WO2025034702A1 (en) 2023-08-07 2025-02-13 Revolution Medicines, Inc. Rmc-6291 for use in the treatment of ras protein-related disease or disorder
WO2025080946A2 (en) 2023-10-12 2025-04-17 Revolution Medicines, Inc. Ras inhibitors
WO2025171296A1 (en) 2024-02-09 2025-08-14 Revolution Medicines, Inc. Ras inhibitors
FR3159741A1 (fr) 2024-03-04 2025-09-05 Pierre Fabre Medicament Formulation topique comprenant du binimetinib
WO2025240847A1 (en) 2024-05-17 2025-11-20 Revolution Medicines, Inc. Ras inhibitors

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HUP0105113A3 (en) * 1999-01-13 2004-11-29 Warner Lambert Co Benzoheterocycles and their use as mek inhibitors and pharmaceutical compositions containing the compounds
AU6068600A (en) * 1999-07-16 2001-02-05 Warner-Lambert Company Method for treating chronic pain using mek inhibitors
PL401638A1 (pl) * 2002-03-13 2013-05-27 Array Biopharma Inc. N3 alkilowane pochodne benzimidazolu jako inhibitory MEK
US7235537B2 (en) * 2002-03-13 2007-06-26 Array Biopharma, Inc. N3 alkylated benzimidazole derivatives as MEK inhibitors
WO2005009975A2 (en) * 2003-07-24 2005-02-03 Warner-Lambert Company Llc Benzimidazole derivatives as mek inhibitors
EP1797881B1 (en) 2004-09-17 2009-04-15 Eisai R&D Management Co., Ltd. Medicinal composition with improved stability and reduced gelation properties
EP1904061B1 (en) 2005-06-23 2018-12-26 Array Biopharma, Inc. SNAr PROCESS FOR PREPARING BENZIMIDAZOLE COMPOUNDS
US8039637B2 (en) 2005-06-23 2011-10-18 Array Biopharma Inc. Process for preparing benzimidazole compounds
TWI405756B (zh) * 2005-12-21 2013-08-21 Array Biopharma Inc 新穎硫酸氫鹽
US20090030058A1 (en) * 2005-12-21 2009-01-29 Mohammed Pervez Tosylate salt of 6- (4-br0m0-2-chl0r0phenylamin0) -7-fluoro-n- (2-hydroxyethoxy) -3-methyl-3h-benzimi dazole- 5 - carboxamide , mek inhibitor useful in the treatment of cancer
AU2008282338B2 (en) * 2007-07-30 2015-02-12 Ardea Biosciences, Inc. Derivatives of N-(arylamino) sulfonamides including polymorphs as inhibitors of MEK as well as compositions, methods of use and methods for preparing the same
US8022057B2 (en) * 2007-11-12 2011-09-20 Takeda Pharmaceutical Company Limited MAPK/ERK kinase inhibitors
JP2012524114A (ja) * 2009-04-21 2012-10-11 ノバルティス アーゲー Mek阻害剤としてのヘテロ環式化合物
WO2012145503A1 (en) 2011-04-21 2012-10-26 Novartis Ag Pharmaceutical combinations
MX2014002480A (es) 2011-09-01 2014-03-27 Novartis Ag Uso del compuesto organico para el tratamiento del sindrome de noonan.
SI2909182T1 (sl) 2012-10-19 2020-03-31 Array Biopharma Inc. Priprava inhibitorja MEK in formulacije, ki obsegajo inhibitor MEK

Also Published As

Publication number Publication date
CA3079071A1 (en) 2014-04-24
US9598376B2 (en) 2017-03-21
PT2909182T (pt) 2020-03-02
HUE065433T2 (hu) 2024-05-28
US20140128442A1 (en) 2014-05-08
CA2888474A1 (en) 2014-04-24
CN104870427B (zh) 2018-10-23
PT3702351T (pt) 2024-01-17
CY1122670T1 (el) 2021-03-12
EP2909182A1 (en) 2015-08-26
SI2909182T1 (sl) 2020-03-31
TW201427956A (zh) 2014-07-16
JP2016503391A (ja) 2016-02-04
US9562016B2 (en) 2017-02-07
DK3702351T3 (da) 2024-01-29
RS65117B1 (sr) 2024-02-29
PL3702351T3 (pl) 2024-04-02
US10398683B2 (en) 2019-09-03
JP2018135399A (ja) 2018-08-30
ES2772498T3 (es) 2020-07-07
LT3702351T (lt) 2024-01-10
ES2971077T3 (es) 2024-06-03
JOP20130304B1 (ar) 2021-08-17
CN109336824B (zh) 2022-11-11
RU2018127873A (ru) 2019-03-14
US20200171002A1 (en) 2020-06-04
BR112015008623B1 (pt) 2022-10-25
EP3702351B1 (en) 2023-11-22
AR099630A1 (es) 2016-08-10
CN109456272A (zh) 2019-03-12
DK2909182T3 (da) 2020-02-17
US20160168103A1 (en) 2016-06-16
US9382212B1 (en) 2016-07-05
US20180296533A1 (en) 2018-10-18
HK1214254A1 (en) 2016-07-22
BR112015008623A2 (pt) 2017-07-04
TWI650316B (zh) 2019-02-11
SI3702351T1 (sl) 2024-03-29
US20170231963A1 (en) 2017-08-17
JP2019194272A (ja) 2019-11-07
CA2888474C (en) 2021-03-02
HRP20240033T1 (hr) 2024-03-29
HUE047708T2 (hu) 2020-05-28
EP4306171A2 (en) 2024-01-17
US20160168102A1 (en) 2016-06-16
US10729678B2 (en) 2020-08-04
PL2909182T3 (pl) 2020-06-01
US9980944B2 (en) 2018-05-29
WO2014063024A1 (en) 2014-04-24
EP3702351A1 (en) 2020-09-02
RU2015118572A (ru) 2016-12-20
US9238627B2 (en) 2016-01-19
EP4306171A3 (en) 2024-04-03
FI3702351T3 (fi) 2024-01-24
CN109336824A (zh) 2019-02-15
JP6737838B2 (ja) 2020-08-12
JP6385939B2 (ja) 2018-09-05
US20160168104A1 (en) 2016-06-16
EP2909182B1 (en) 2019-12-04
SMT202400044T1 (it) 2024-03-13
RU2669391C2 (ru) 2018-10-11
CN104870427A (zh) 2015-08-26
EP2909182A4 (en) 2016-07-06

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