CA2897055C - Substituted 2-(trifluoromethylsulfonyl)phenylamino compounds and pharmaceutical compositions thereof as bcl-2/bcl-xl inhibitors and therapeutic methods using the same - Google Patents

Substituted 2-(trifluoromethylsulfonyl)phenylamino compounds and pharmaceutical compositions thereof as bcl-2/bcl-xl inhibitors and therapeutic methods using the same Download PDF

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CA2897055C
CA2897055C CA2897055A CA2897055A CA2897055C CA 2897055 C CA2897055 C CA 2897055C CA 2897055 A CA2897055 A CA 2897055A CA 2897055 A CA2897055 A CA 2897055A CA 2897055 C CA2897055 C CA 2897055C
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compound
pharmaceutically acceptable
alkyl
cancer
acceptable salt
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French (fr)
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CA2897055A1 (en
Inventor
Shaomeng Wang
Jianfang Chen
Donna Mceachern
Longchuan Bai
Liu Liu
Duxin Sun
Xiaoqin LI
Angelo AGUILAR
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University of Michigan System
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University of Michigan System
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
    • 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
    • A61K31/495Heterocyclic 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
    • A61K31/496Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/66Phosphorus compounds
    • A61K31/675Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00Medicinal preparations containing inorganic active ingredients
    • A61K33/24Heavy metals; Compounds thereof
    • A61K33/30Zinc; Compounds thereof
    • 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
    • A61NELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
    • A61N5/00Radiation therapy
    • A61N5/10X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
    • 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
    • C07D401/00Heterocyclic 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
    • C07D401/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pathology (AREA)
  • Radiology & Medical Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2897055A 2013-01-16 2014-01-15 Substituted 2-(trifluoromethylsulfonyl)phenylamino compounds and pharmaceutical compositions thereof as bcl-2/bcl-xl inhibitors and therapeutic methods using the same Active CA2897055C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361753066P 2013-01-16 2013-01-16
US61/753,066 2013-01-16
PCT/US2014/011571 WO2014113413A1 (en) 2013-01-16 2014-01-15 Bcl-2bcl-xl inhibitors and therapeutic methods using the same

Publications (2)

Publication Number Publication Date
CA2897055A1 CA2897055A1 (en) 2014-07-24
CA2897055C true CA2897055C (en) 2021-04-20

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CA2897055A Active CA2897055C (en) 2013-01-16 2014-01-15 Substituted 2-(trifluoromethylsulfonyl)phenylamino compounds and pharmaceutical compositions thereof as bcl-2/bcl-xl inhibitors and therapeutic methods using the same

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Country Link
US (2) US9096625B2 (OSRAM)
EP (2) EP3689886A1 (OSRAM)
JP (1) JP6347793B2 (OSRAM)
KR (2) KR102210316B1 (OSRAM)
CN (3) CN110302205B (OSRAM)
AU (1) AU2014207716B2 (OSRAM)
CA (1) CA2897055C (OSRAM)
ES (1) ES2819232T3 (OSRAM)
HK (1) HK1219734A1 (OSRAM)
NZ (1) NZ709635A (OSRAM)
SG (1) SG11201505525UA (OSRAM)
WO (1) WO2014113413A1 (OSRAM)
ZA (1) ZA201504902B (OSRAM)

Families Citing this family (58)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3689886A1 (en) * 2013-01-16 2020-08-05 The Regents of The University of Michigan Bcl-2/bcl-xl inhibitors and their use in the treatment of cancer
EP3669881B1 (en) 2014-01-28 2022-03-30 Buck Institute for Research on Aging Compositions for use in the treatment of senescence-assiocated eye disease and disorders
EP3139942B1 (en) 2014-05-05 2019-12-18 Bioventures, Llc COMPOSITIONS AND METHODS FOR INHIBITING ANTIAPOPTOTIC Bcl-2 PROTEINS AS ANTI-AGING AGENTS
US10071087B2 (en) 2014-07-22 2018-09-11 Bioventures, Llc Compositions and methods for selectively depleting senescent cells
CN108025006A (zh) * 2015-02-06 2018-05-11 尤尼蒂生物技术公司 化合物及在治疗衰老相关病症中的用途
US20180000816A1 (en) * 2015-02-06 2018-01-04 Unity Biotechnology, Inc. Use of a Heterocyclic Bcl-xL Inhibitor and Related Analogs for Removing Senescent Cells in the Treatment of Eye Diseases and Other Age-Related Conditions
US11111259B2 (en) 2015-12-18 2021-09-07 Unity Biotechnology, Inc. Acylsulfonamide derivatives for treating senescence-associated diseases and disorders
IL295472B2 (en) 2016-03-28 2024-10-01 Presage Biosciences Inc Pharmaceutical combinations for the treatment of cancer
JP6936498B2 (ja) * 2016-04-21 2021-09-15 バイオベンチャーズ・リミテッド・ライアビリティ・カンパニーBioVentures, LLC 抗アポトーシス性Bcl−2ファミリータンパク質の分解を誘導する化合物及びその使用
CN106177955B (zh) * 2016-08-18 2018-03-16 广州威溶特医药科技有限公司 Bcl‑xL抑制剂和溶瘤病毒在制备抗肿瘤药物中的应用
WO2018098534A1 (en) * 2016-12-02 2018-06-07 Garvan Institute Of Medical Research Methods of treating cancer and reagents thereof
WO2019033122A1 (en) * 2017-08-11 2019-02-14 Unity Biotechnology, Inc. TREATMENT OF PULMONARY DISEASES USING PHARMACEUTICAL AGENTS THAT ELIMINATE SENESCENT CELLS
JP7278257B2 (ja) * 2017-08-11 2023-05-19 ユニティ バイオテクノロジー インコーポレイテッド 老化細胞を排除する薬学的作用物質を用いる、黄斑変性症、緑内障、および糖尿病性網膜症などの眼病態の治療
US20200354336A9 (en) * 2017-08-11 2020-11-12 Unity Biotechnology, Inc. Treatment of Lung Diseases Using Pharmaceutical Agents that Eliminate Senescent Cells
US10588916B2 (en) 2017-10-31 2020-03-17 Unity Biotechnology, Inc. Technology to inhibit vascular changes that lead to vision loss in the eye
AU2018357829B2 (en) 2017-12-30 2019-09-26 Unity Biotechnology, Inc. Peptide-based proteasome inhibitors for treating conditions mediated by senescent cells and for treating cancer
SG11202005785XA (en) 2018-01-10 2020-07-29 Recurium Ip Holdings Llc Benzamide compounds
JP7385284B2 (ja) * 2018-01-22 2023-11-22 バイオベンチャーズ・リミテッド・ライアビリティ・カンパニー 癌処置のためのbcl-2タンパク質分解剤
EP3788042B1 (en) 2018-04-29 2025-02-12 BeiGene Switzerland GmbH Bcl-2 inhibitors
US10738042B2 (en) 2018-04-30 2020-08-11 Unity Biotechnology, Inc. Phosphonamidates that are Bcl family antagonists for use in clinical management of conditions caused or mediated by senescent cells and for treating cancer
WO2019213153A1 (en) * 2018-04-30 2019-11-07 Unity Biotechnology Phospholidines that are bcl family antagonists for use in clinical management of conditions caused or mediated by senescent cells and for treating cancer
CA3056878C (en) 2018-04-30 2021-03-30 Unity Biotechnology Phospholidines that are bcl family antagonists for use in clinical management of conditions caused or mediated by senescent cells and for treating cancer
WO2019221755A1 (en) 2018-05-18 2019-11-21 Bioventures, Llc Piperlongumine analogues and uses thereof
US10717722B2 (en) 2018-06-13 2020-07-21 Unity Biotechnology, Inc. Acyl sulfonamides that are Bcl family antagonists for use in clinical management of conditions caused or mediated by senescent cells and for treating cancer
EA202091963A1 (ru) 2018-07-31 2021-05-13 Эсентейдж Фарма (Сучжоу) Ко., Лтд. СИНЕРГИЧЕСКИЙ ПРОТИВООПУХОЛЕВЫЙ ЭФФЕКТ ИНГИБИТОРА Bcl-2 В СОЧЕТАНИИ С РИТУКСИМАБОМ И/ИЛИ БЕНДАМУСТИНОМ ИЛИ ИНГИБИТОРА Bcl-2 В СОЧЕТАНИИ С CHOP
CN110776507B (zh) 2018-07-31 2020-12-18 苏州亚盛药业有限公司 Bcl-2抑制剂与化疗药的组合产品及其在预防和/或治疗疾病中的用途
US11491168B2 (en) 2018-07-31 2022-11-08 Ascentage Pharma (Suzhou) Co., Ltd. Combination of Bcl-2/Bcl-xL inhibitors and chemotherapeutic agent and use thereof
CN110772521A (zh) * 2018-07-31 2020-02-11 苏州亚盛药业有限公司 Bcl-2抑制剂或Bcl-2/Bcl-xL抑制剂与BTK抑制剂的组合产品及其用途
EP3829593A4 (en) * 2018-07-31 2022-04-13 Ascentage Pharma (Suzhou) Co., Ltd. Combination of bcl-2/bcl-xl inhibitors and chemotherapeutic agent and use thereof
UA126098C2 (uk) 2018-07-31 2022-08-10 Есентейдж Фарма (Сучжоу) Ко., Лтд. КОМБІНОВАНИЙ ПРОДУКТ НА ОСНОВІ ІНГІБІТОРА Bcl-2 ТА ІНГІБІТОРА MDM2 ТА ЙОГО ЗАСТОСУВАННЯ В ПОПЕРЕДЖЕННІ ТА/АБО ЛІКУВАННІ ЗАХВОРЮВАНЬ
US11903950B2 (en) 2018-08-22 2024-02-20 Newave Pharmaceutical Inc. BCL-2 inhibitors
US11872237B2 (en) * 2018-12-28 2024-01-16 Ascentage Pharma (Suzhou) Co., Ltd. Pharmaceutical composition and preparation method thereof
TWI729662B (zh) * 2019-01-04 2021-06-01 大陸商蘇州亞盛藥業有限公司 一種磺胺類化合物及製備磺胺類化合物的製程
EP3906235B1 (en) 2019-01-04 2023-03-15 Ascentage Pharma (Suzhou) Co., Ltd. Method for preparing sulfonamides drugs
TWI770503B (zh) * 2019-05-13 2022-07-11 大陸商蘇州亞盛藥業有限公司 用於預測bcl-2/bcl-xl抑制劑對癌症的功效的方法和組合物
WO2021000899A1 (en) * 2019-07-02 2021-01-07 Ascentage Pharma (Suzhou) Co., Ltd. A PHARMACEUTICAL COMBINATION CONTAINING mTOR INHIBITOR AND USE THEREOF
JP2021535129A (ja) * 2019-07-31 2021-12-16 アセンテージ ファーマ(スーチョウ)カンパニー,リミティド Bcl−2/Bcl−xL阻害剤及び化学療法剤の組み合わせ製品、並びに疾患の予防及び/又は治療におけるその使用
US20220372042A1 (en) 2019-10-03 2022-11-24 Newave Pharmaceutical Inc. Condensed heterocycles as bcl-2 inhibitors
CN112707900B (zh) * 2019-10-24 2022-06-10 上海科技大学 蛋白降解剂及其在疾病治疗中的应用
EP4051676A4 (en) 2019-10-28 2023-11-22 BeiGene, Ltd. BCL-2 INHIBITORS
WO2021104442A1 (en) * 2019-11-27 2021-06-03 Ascentage Pharma (Suzhou) Co., Ltd. Method and compositions for predicting anti-cancer efficacy of compounds targeting apoptosis pathway
CN118766921A (zh) * 2019-12-04 2024-10-15 苏州亚盛药业有限公司 药物组合及其用途
US20230025865A1 (en) * 2019-12-11 2023-01-26 The Regents Of The University Of Michigan COMPOSITIONS AND METHODS FOR SYSTEMIC DELIVERY OF Bcl-2 AND Bcl-xL ANTAGONISTS
CN113350281B (zh) * 2020-03-02 2023-08-15 苏州亚盛药业有限公司 载药聚合物胶束及其制剂和制备方法
EP3914257B1 (en) * 2020-04-10 2023-12-27 Ascentage Pharma (Suzhou) Co., Ltd. Combination of a bcl-2/bcl-xl inhibitor with osimertinib
WO2021208963A1 (en) 2020-04-15 2021-10-21 Beigene, Ltd. Bcl-2 inhibitor
WO2021233948A1 (en) 2020-05-19 2021-11-25 INSERM (Institut National de la Santé et de la Recherche Médicale) Method to treat a pathogen lung infection
WO2022008464A1 (en) 2020-07-06 2022-01-13 INSERM (Institut National de la Santé et de la Recherche Médicale) Combination of antineoplastic antibiotics and bcl-2 inhibitors for the treatment of npm-1-driven acute myeloid leukemia (aml)
US12528832B2 (en) 2020-07-13 2026-01-20 Ascentage Pharma (Suzhou) Co., Ltd. Crystalline or amorphous form of Bcl-2/Bcl-xL inhibitor compound or its salts
WO2022022706A1 (en) * 2020-07-31 2022-02-03 Ascentage Pharma (Suzhou) Co., Ltd. Compositions and methods for treating lung diseases
KR20230145313A (ko) * 2020-11-10 2023-10-17 유니티 바이오테크놀로지, 인크. Bcl의 결정성 고체 메글루민 염 억제제 및 이의 제조 방법 및 이의 사용 방법
WO2022111647A1 (en) * 2020-11-27 2022-06-02 Ascentage Pharma (Suzhou) Co., Ltd. Formulation combination containing freeze-dried formulation and reconstituted solvent, preparation method and application thereof
WO2022120114A1 (en) 2020-12-04 2022-06-09 University Of Notre Dame Du Lac Method of encapsulating single cells utilizing an alternating current electrospray
WO2023011488A1 (zh) * 2021-08-02 2023-02-09 苏州亚盛药业有限公司 一种药物组合及其用途
CN120265288A (zh) * 2022-08-02 2025-07-04 北京星奇原生物科技有限公司 Bcl-xl降解化合物
WO2024051741A1 (zh) * 2022-09-06 2024-03-14 西藏海思科制药有限公司 一种抑制Bcl-2或Bcl-xL的化合物及其在医药上的应用
WO2024245312A1 (en) * 2023-05-30 2024-12-05 Ascentage Pharma (Suzhou) Co., Ltd. Bcl-2/bcl-xl protein degrader and use thereof
WO2025087879A2 (en) 2023-10-23 2025-05-01 Institut National de la Santé et de la Recherche Médicale Suppressing the pi3kgamma/akt signalling pathway for the treatment of acute myeloid leukemia

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7432304B2 (en) 2001-05-30 2008-10-07 The Regents Of The University Of Michigan Small molecule antagonists of Bcl-2 family proteins
US7973161B2 (en) * 2003-11-13 2011-07-05 Abbott Laboratories Apoptosis promoters
KR20070046180A (ko) 2004-08-20 2007-05-02 더 리젠츠 오브 더 유니버시티 오브 미시간 항세포사멸 bcl-2군 구성원의 소분자 억제제 및 이의용도
NZ561609A (en) 2005-05-12 2010-03-26 Abbott Lab 3-((trifluoromethyl)sulfonyl)benzenesulfonamide and 3-((chloro(difluoro)methyl)sulfonyl)benzenesulfonamide apoptosis promoters
JP2009515997A (ja) 2005-11-18 2009-04-16 タケダ サン ディエゴ インコーポレイテッド グルコキナーゼ活性剤
CA2662320C (en) * 2006-09-05 2014-07-22 Abbott Laboratories Bcl inhibitors treating platelet excess
BRPI0916356B1 (pt) 2008-07-24 2022-08-23 Nerviano Medical Sciences S.R.L 3,4-diaril pirazois como inibidores da proteína quinase
US20100278921A1 (en) 2009-04-30 2010-11-04 Fischer Cristina M Solid oral formulation of abt-263
TWI535712B (zh) 2010-08-06 2016-06-01 阿斯特捷利康公司 化合物
EP3459945A1 (en) * 2011-01-25 2019-03-27 The Regents of The University of Michigan Bcl-2/bcl-xl inhibitors for use in the treatment of cancer
EP3689886A1 (en) * 2013-01-16 2020-08-05 The Regents of The University of Michigan Bcl-2/bcl-xl inhibitors and their use in the treatment of cancer

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Publication number Publication date
CA2897055A1 (en) 2014-07-24
AU2014207716B2 (en) 2017-07-27
JP6347793B2 (ja) 2018-06-27
SG11201505525UA (en) 2015-08-28
CN110305162A (zh) 2019-10-08
ES2819232T3 (es) 2021-04-15
CN110302205B (zh) 2020-06-09
US9096625B2 (en) 2015-08-04
KR102210316B1 (ko) 2021-01-29
ZA201504902B (en) 2016-07-27
HK1219734A1 (zh) 2017-04-13
KR20210002126A (ko) 2021-01-06
US9403856B2 (en) 2016-08-02
AU2014207716A1 (en) 2015-07-23
JP2016506916A (ja) 2016-03-07
EP3689886A1 (en) 2020-08-05
US20150336994A1 (en) 2015-11-26
EP2945940B1 (en) 2020-07-15
NZ709635A (en) 2019-10-25
EP2945940A1 (en) 2015-11-25
KR20150104631A (ko) 2015-09-15
EP2945940A4 (en) 2016-07-06
WO2014113413A1 (en) 2014-07-24
KR102318204B1 (ko) 2021-10-26
CN105246882A (zh) 2016-01-13
CN110302205A (zh) 2019-10-08
US20140199234A1 (en) 2014-07-17

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