CA2865944C - Process for making piperidinone carboxamide indane and azainane cgrp receptor antagonists - Google Patents

Process for making piperidinone carboxamide indane and azainane cgrp receptor antagonists Download PDF

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Publication number
CA2865944C
CA2865944C CA2865944A CA2865944A CA2865944C CA 2865944 C CA2865944 C CA 2865944C CA 2865944 A CA2865944 A CA 2865944A CA 2865944 A CA2865944 A CA 2865944A CA 2865944 C CA2865944 C CA 2865944C
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formula
compound
yield
process according
group
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French (fr)
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CA2865944A1 (en
Inventor
Kevin M. Belyk
Edward Cleator
Shen-Chun Kuo
Peter Emmanuel Maligres
Bangping Xiang
Nobuyoshi Yasuda
Jianguo Yin
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Merck Sharp & Dohme LLC
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Merck Sharp & Dohme LLC
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36—Opioid-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic 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
    • C07D405/02—Heterocyclic 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
    • C07D405/06—Heterocyclic 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 linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic 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
    • C07D405/02—Heterocyclic 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
    • C07D405/12—Heterocyclic 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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/20—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Pulmonology (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Psychiatry (AREA)
  • Addiction (AREA)
  • Rheumatology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Dermatology (AREA)
  • Immunology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Epidemiology (AREA)
  • Peptides Or Proteins (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2865944A 2012-03-14 2013-03-13 Process for making piperidinone carboxamide indane and azainane cgrp receptor antagonists Active CA2865944C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201261610746P 2012-03-14 2012-03-14
US61/610,746 2012-03-14
US201261644648P 2012-05-09 2012-05-09
US61/644,648 2012-05-09
PCT/US2013/030696 WO2013138418A2 (en) 2012-03-14 2013-03-13 Process for making cgrp receptor antagonists

Publications (2)

Publication Number Publication Date
CA2865944A1 CA2865944A1 (en) 2013-09-19
CA2865944C true CA2865944C (en) 2020-12-08

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CA2865944A Active CA2865944C (en) 2012-03-14 2013-03-13 Process for making piperidinone carboxamide indane and azainane cgrp receptor antagonists

Country Status (11)

Country Link
US (1) US9487523B2 (enExample)
EP (1) EP2825044B1 (enExample)
JP (3) JP6212534B2 (enExample)
KR (7) KR20220164616A (enExample)
CN (1) CN104168768B (enExample)
AU (1) AU2013232196C1 (enExample)
BR (1) BR112014022542A8 (enExample)
CA (1) CA2865944C (enExample)
MX (1) MX346252B (enExample)
RU (1) RU2672056C2 (enExample)
WO (1) WO2013138418A2 (enExample)

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TWI501968B (zh) * 2010-11-12 2015-10-01 Merck Sharp & Dohme 六氫吡啶酮甲醯胺氮雜茚滿ｃｇｒｐ受體拮抗劑
WO2013138413A1 (en) 2012-03-14 2013-09-19 Merck Sharp & Dohme Corp. Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts
US9174989B2 (en) * 2012-05-09 2015-11-03 Merck Sharp & Dohme Corp. Process for making CGRP receptor antagonists
US12168004B2 (en) 2014-02-05 2024-12-17 Merck Sharp & Dohme Llc Treatment of migraine
US10117836B2 (en) 2014-02-05 2018-11-06 Merck Sharp & Dohme Corp. Tablet formulation for CGRP active compounds
CN105037210A (zh) * 2015-05-27 2015-11-11 江苏大学 一种α，β-脱氢-α-氨基酸的合成方法
GB201707938D0 (en) 2017-05-17 2017-06-28 Univ Sheffield Compounds
US12383545B1 (en) 2018-06-08 2025-08-12 Allergan Pharmaceuticals International Limited Treatment of migraine
JP7690493B2 (ja) * 2020-05-04 2025-06-10 大鵬薬品工業株式会社 Ｉａｐアンタゴニスト化合物及びその中間体、並びにそれを合成する方法
MX2023001071A (es) 2020-07-29 2023-05-12 Allergan Pharmaceuticals Int Ltd Tratamiento de la migraña.
CA3206184A1 (en) 2020-12-22 2022-06-30 Allergan Pharmaceuticals International Limited Treatment of migraine
JP2024533756A (ja) 2021-09-27 2024-09-12 アラガン ファーマスーティカルズ インターナショナル リミテッド アトゲパントを含む片頭痛の併用療法
WO2024134683A1 (en) * 2022-12-21 2024-06-27 Msn Laboratories Private Limited, R&D Center Novel process for the preparation of intermediate compounds used in the treatment of migraine
CN117603205A (zh) * 2023-12-20 2024-02-27 杭州澳赛诺生物科技有限公司 一种奎尼丁衍生物手性相转移催化剂的合成方法及应用
CN119431222B (zh) * 2024-11-04 2025-10-17 杭州澳赛诺生物科技有限公司 一种不对称合成乌布吉泮手性中间体的方法
CN119350337A (zh) * 2024-12-24 2025-01-24 药康众拓(北京)医药科技有限公司 一类氘代哌啶酮酸酰胺氮杂茚满类cgrp抑制剂药物及用途
CN120398716A (zh) * 2025-04-17 2025-08-01 珠海奥博凯生物医药技术有限公司 一种基于连续流反应技术合成5-氰基-2-氟苯基化合物的方法

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ATE520661T1 (de) * 2003-06-27 2011-09-15 Univ Maryland Heterocyclische verbindungen mit quaternärem stickstoff zum nachweis von wässrigen monosacchariden in physiologischen flüssigkeiten
CN101124217A (zh) * 2004-01-29 2008-02-13 默克公司 Cgrp受体拮抗剂
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TWI501968B (zh) * 2010-11-12 2015-10-01 Merck Sharp & Dohme 六氫吡啶酮甲醯胺氮雜茚滿ｃｇｒｐ受體拮抗劑
WO2012064911A1 (en) 2010-11-12 2012-05-18 Merck Sharp & Dohme Corp. Piperidinone carboxamide indane cgrp receptor antagonists
WO2013138413A1 (en) 2012-03-14 2013-09-19 Merck Sharp & Dohme Corp. Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts
US9174989B2 (en) 2012-05-09 2015-11-03 Merck Sharp & Dohme Corp. Process for making CGRP receptor antagonists

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AU2013232196C1 (en) 2017-03-16
US20150038707A1 (en) 2015-02-05
KR20240010553A (ko) 2024-01-23
JP2018030858A (ja) 2018-03-01
JP6572273B2 (ja) 2019-09-04
KR102071278B1 (ko) 2020-03-03
RU2672056C2 (ru) 2018-11-09
AU2013232196B2 (en) 2016-12-01
CN104168768A (zh) 2014-11-26
WO2013138418A2 (en) 2013-09-19
WO2013138418A3 (en) 2014-05-30
EP2825044A4 (en) 2015-12-02
EP2825044B1 (en) 2018-08-15
JP2015516946A (ja) 2015-06-18
CN104168768B (zh) 2017-03-01
EP2825044A2 (en) 2015-01-21
JP2019206586A (ja) 2019-12-05
KR20140138705A (ko) 2014-12-04
CA2865944A1 (en) 2013-09-19
US9487523B2 (en) 2016-11-08
KR20220164616A (ko) 2022-12-13
KR102220242B1 (ko) 2021-02-25
AU2013232196A1 (en) 2014-08-21
JP6743256B2 (ja) 2020-08-19
BR112014022542A2 (enExample) 2017-06-20
MX346252B (es) 2017-03-10
KR20200011559A (ko) 2020-02-03
KR20210116717A (ko) 2021-09-27
KR20250028525A (ko) 2025-02-28
RU2014141158A (ru) 2016-05-10
JP6212534B2 (ja) 2017-10-11
KR20210022150A (ko) 2021-03-02
MX2014011000A (es) 2014-10-13
BR112014022542A8 (pt) 2023-04-11

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