CA2974370C - 4-methylsulfonyl-substituted piperidine urea compounds useful for the treatment of cardiac disorders such as dilated cardiomyopathy (dcm) - Google Patents

4-methylsulfonyl-substituted piperidine urea compounds useful for the treatment of cardiac disorders such as dilated cardiomyopathy (dcm) Download PDF

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Publication number
CA2974370C
CA2974370C CA2974370A CA2974370A CA2974370C CA 2974370 C CA2974370 C CA 2974370C CA 2974370 A CA2974370 A CA 2974370A CA 2974370 A CA2974370 A CA 2974370A CA 2974370 C CA2974370 C CA 2974370C
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Prior art keywords
compound
heart failure
pharmaceutically acceptable
acceptable salt
dcm
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English (en)
French (fr)
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CA2974370A1 (en
Inventor
Johan Oslob
Danielle Aubele
Jae Kim
Robert Mcdowell
Yonghong Song
Arvinder Sran
Min Zhong
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Myokardia Inc
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Myokardia Inc
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    • 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
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • 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
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Cardiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2974370A 2015-01-22 2016-01-21 4-methylsulfonyl-substituted piperidine urea compounds useful for the treatment of cardiac disorders such as dilated cardiomyopathy (dcm) Active CA2974370C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562106571P 2015-01-22 2015-01-22
US62/106,571 2015-01-22
PCT/US2016/014365 WO2016118774A1 (en) 2015-01-22 2016-01-21 4-methylsulfonyl-substituted piperidine urea compounds for the treatment of dilated cardiomyopathy (dcm)

Publications (2)

Publication Number Publication Date
CA2974370A1 CA2974370A1 (en) 2016-07-28
CA2974370C true CA2974370C (en) 2023-10-31

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CA2974370A Active CA2974370C (en) 2015-01-22 2016-01-21 4-methylsulfonyl-substituted piperidine urea compounds useful for the treatment of cardiac disorders such as dilated cardiomyopathy (dcm)

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US (1) US9925177B2 (enExample)
EP (2) EP4234017B1 (enExample)
JP (1) JP6712275B2 (enExample)
KR (3) KR102688851B1 (enExample)
CN (3) CN118164961A (enExample)
AU (4) AU2016209200B2 (enExample)
BR (1) BR112017015627B1 (enExample)
CA (1) CA2974370C (enExample)
CL (1) CL2017001871A1 (enExample)
CO (1) CO2017008398A2 (enExample)
CR (1) CR20170370A (enExample)
DK (1) DK3247707T3 (enExample)
DO (2) DOP2017000166A (enExample)
EA (1) EA036923B1 (enExample)
EC (1) ECSP17054181A (enExample)
ES (2) ES2953480T3 (enExample)
FI (1) FI3247707T3 (enExample)
GT (1) GT201700163A (enExample)
HR (1) HRP20230737T1 (enExample)
HU (1) HUE063410T2 (enExample)
IL (6) IL313678A (enExample)
LT (1) LT3247707T (enExample)
MX (3) MX394704B (enExample)
MY (1) MY203427A (enExample)
PE (2) PE20212253A1 (enExample)
PH (2) PH12017501279B1 (enExample)
PL (1) PL3247707T3 (enExample)
PT (1) PT3247707T (enExample)
RS (1) RS64432B1 (enExample)
SG (2) SG11201705928XA (enExample)
SI (1) SI3247707T1 (enExample)
SM (1) SMT202300259T1 (enExample)
TN (1) TN2017000320A1 (enExample)
UA (1) UA119905C2 (enExample)
WO (1) WO2016118774A1 (enExample)
ZA (1) ZA201704777B (enExample)

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BR112020004800A2 (pt) 2017-09-13 2020-09-24 Amgen Inc. compostos de bisamida ativantes do sarcômero e seus usos
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MA54677A (fr) 2018-02-01 2021-11-17 Myokardia Inc Composés pyrazoles et leur préparation
JP7438148B2 (ja) 2018-06-26 2024-02-26 サイトキネティックス， インコーポレイテッド 心臓サルコメア阻害剤
EP3814343B1 (en) 2018-06-26 2023-01-11 Cytokinetics, Inc. Cardiac sarcomere inhibitors
GB201813312D0 (en) 2018-08-15 2018-09-26 Modern Biosciences Ltd Compounds and their therapeutic use
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GB201905520D0 (en) 2019-04-18 2019-06-05 Modern Biosciences Ltd Compounds and their therapeutic use
SG11202112723PA (en) * 2019-05-19 2021-12-30 Myokardia Inc Treatment of systolic dysfunction and heart failure with reduced ejection fraction with the compound(r)-4-(1-((3-(difluoromethyl)-1-methyl-1h-pyrazol-4-yl)sulfonyl)-1-fluoroethyl)-n-(isoxazol-3-yl)piperidine-1-carboxamide
US20210053939A1 (en) 2019-07-16 2021-02-25 MyoKardia, Inc. Polymorphic forms of (r)-4-(1-((3-(difluoromethyl)-1-methyl-1h-pyrazol-4-yl)sulfonyl)-1-fluoroethyl)-n-(isoxazol-3-yl)piperidine-1-carboxamide
CN110407744A (zh) * 2019-08-13 2019-11-05 上海毕得医药科技有限公司 一种1-(4-氨基吡啶-2-基)乙酮的合成方法
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KR102698413B1 (ko) 2020-05-05 2024-08-26 뉴베일런트, 아이엔씨. 헤테로방향족 거대환식 에터 화학치료제
JP7832128B2 (ja) * 2020-06-15 2026-03-17 マイオカーディア，インク 心房機能不全の治療
KR102541297B1 (ko) 2020-08-18 2023-06-09 가톨릭대학교 산학협력단 확장성 심근병 모델 및 이의 제조방법
KR20240015622A (ko) 2021-03-04 2024-02-05 싸이토키네틱스, 인코포레이티드 심장 근절 억제제
WO2023049919A1 (en) * 2021-09-27 2023-03-30 The Trustees Of The University Of Pennsylvania Inhibitors of molluscum contagiosum infection and methods using the same
TW202320768A (zh) 2021-10-01 2023-06-01 美商努法倫特公司 雜芳族大環醚化合物之固體形式、醫藥組成物及製備
CN116082326B (zh) * 2022-12-16 2024-12-27 药康众拓(江苏)医药科技有限公司北京分公司 一种氘代吡唑磺酰甲基-哌啶异噁唑脲类化合物及其用途
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DOP2017000166A (es) 2017-10-15
KR20170113578A (ko) 2017-10-12
EA036923B1 (ru) 2021-01-15
US20160243100A1 (en) 2016-08-25
CN107428719B (zh) 2020-03-27
UA119905C2 (uk) 2019-08-27
EP3247707A1 (en) 2017-11-29
JP2018502883A (ja) 2018-02-01
AU2016209200B2 (en) 2020-07-02
AU2023200361B2 (en) 2024-08-22
CL2017001871A1 (es) 2018-04-13
EA201791656A1 (ru) 2017-11-30
MX2017009540A (es) 2017-10-20
MX2021010778A (es) 2022-08-11
EP4234017A3 (en) 2023-10-18
US9925177B2 (en) 2018-03-27
HUE063410T2 (hu) 2024-01-28
CR20170370A (es) 2017-10-20
KR102585550B1 (ko) 2023-10-10
AU2024266781A1 (en) 2024-12-12
AU2016209200A1 (en) 2017-08-10
IL279247A (en) 2021-01-31
MX394704B (es) 2025-03-24
HRP20230737T1 (hr) 2023-10-13
MY203427A (en) 2024-06-27
BR112017015627A2 (pt) 2018-03-13
CN111393414B (zh) 2024-05-07
KR20240119163A (ko) 2024-08-06
ES3075390T3 (en) 2026-08-04
IL253552A0 (en) 2017-09-28
CA2974370A1 (en) 2016-07-28
ES2953480T3 (es) 2023-11-13
KR102688851B1 (ko) 2024-07-29
HK1246775A1 (en) 2018-09-14
WO2016118774A1 (en) 2016-07-28
DK3247707T3 (da) 2023-07-03
EP4234017B1 (en) 2026-04-15
PL3247707T3 (pl) 2023-12-11
IL313678A (en) 2024-08-01
PE20171511A1 (es) 2017-10-20
DOP2022000172A (es) 2022-09-30
KR20230145504A (ko) 2023-10-17
PH12017501279A1 (en) 2018-01-29
IL295547A (en) 2022-10-01
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MX385960B (es) 2025-03-18
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