CN108778289B - 三萜皂苷类似物 - Google Patents

三萜皂苷类似物 Download PDF

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Publication number
CN108778289B
CN108778289B CN201680078068.9A CN201680078068A CN108778289B CN 108778289 B CN108778289 B CN 108778289B CN 201680078068 A CN201680078068 A CN 201680078068A CN 108778289 B CN108778289 B CN 108778289B
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oxygen
nitrogen
sulfur
antigen
independently selected
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CN108778289A (zh
Inventor
D.Y.金
E.切亚
A.弗南德斯-特雅达
J.加德纳
J.刘易斯
P.利文斯顿
J.T.马丁
L.诺德斯特龙
N.V.K.皮拉塞蒂
G.拉古帕蒂
D.坦
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Adjuvant Technology Co
Memorial Sloan Kettering Cancer Center
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Memorial Sloan Kettering Cancer Center
Adjuvance Technologies Inc
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Publication of CN108778289A publication Critical patent/CN108778289A/zh
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7024—Esters of saccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/02—Bacterial antigens
    • A61K39/08—Clostridium, e.g. Clostridium tetani
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/02—Bacterial antigens
    • A61K39/099—Bordetella
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C07H13/06—Fatty acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/02—Bacterial antigens
    • A61K2039/10—Brucella; Bordetella, e.g. Bordetella pertussis; Not used, see subgroups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
    • A61K2039/55511—Organic adjuvants
    • A61K2039/55577—Saponins; Quil A; QS21; ISCOMS
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
    • A61K2039/55511—Organic adjuvants
    • A61K2039/55583—Polysaccharides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Health & Medical Sciences (AREA)
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  • Molecular Biology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
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  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Virology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Saccharide Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Medicinal Preparation (AREA)
CN201680078068.9A 2015-11-06 2016-11-04 三萜皂苷类似物 Active CN108778289B (zh)

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CN202011417416.5A CN112812143A (zh) 2015-11-06 2016-11-04 三萜皂苷类似物

Applications Claiming Priority (5)

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US201562252296P 2015-11-06 2015-11-06
US62/252296 2015-11-06
US201562268837P 2015-12-17 2015-12-17
US62/268837 2015-12-17
PCT/US2016/060564 WO2017079582A1 (en) 2015-11-06 2016-11-04 Triterpene saponin analogues

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CN108778289A CN108778289A (zh) 2018-11-09
CN108778289B true CN108778289B (zh) 2020-11-17

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US (5) US20180327436A1 (https=)
EP (2) EP3370730A4 (https=)
JP (3) JP6900385B2 (https=)
KR (1) KR20180077180A (https=)
CN (2) CN108778289B (https=)
AU (1) AU2016349693B2 (https=)
CA (1) CA3003483C (https=)
CL (1) CL2018001192A1 (https=)
IL (3) IL286493B (https=)
SG (2) SG10202012205XA (https=)
WO (1) WO2017079582A1 (https=)
ZA (1) ZA201802891B (https=)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102424785B1 (ko) * 2014-05-30 2022-07-25 메모리얼 슬로안 케터링 캔서 센터 최소 사포닌 유사체, 이의 합성법 및 용도
CN108778289B (zh) * 2015-11-06 2020-11-17 佐剂技术公司 三萜皂苷类似物
WO2018191598A1 (en) * 2017-04-13 2018-10-18 Adjuvance Technologies, Inc. Triterpene saponin synthesis, intermediates and adjuvant combinations
US20200164065A1 (en) * 2017-04-25 2020-05-28 Adjuvance Technologies, Inc. Triterpene saponin analogues
CA3061205A1 (en) 2017-04-25 2018-11-01 Memorial Sloan Kettering Cancer Center Triterpene saponin analogues
SG11202001826YA (en) * 2017-10-16 2020-03-30 Adjuvance Technologies Inc Triterpene saponin analogues
WO2021195024A1 (en) * 2020-03-23 2021-09-30 Adjuvance Technologies, Inc. Adjuvant compounds, salt forms, and formulations
BR112022023366A2 (pt) 2020-05-19 2023-05-02 Othair Prothena Ltd Vacina com múltiplos epítopos para o tratamento de mal de alzheimer
WO2022032166A1 (en) 2020-08-07 2022-02-10 Othair Prothena Limited Multiepitope vaccine for the treatment of alzheimer's disease
WO2023056089A1 (en) 2021-10-03 2023-04-06 Eisai R&D Management Co., Ltd. Immunological adjuvant formulations comprising tlr4 agonist e6020
EP4429674A4 (en) * 2021-11-08 2025-10-08 Adjuvance Tech Inc ADJUVANT COMPOUNDS AND FORMULATIONS
EP4190359A1 (en) 2021-12-03 2023-06-07 Asociación Centro de Investigación Cooperativa en Biociencias - CIC bioGUNE Saponin-based adjuvants and vaccines
EP4466278A1 (en) 2022-01-19 2024-11-27 Asociación Centro de Investigación Cooperativa en Biociencias - CIC bioGUNE Saponin-based adjuvants and vaccines
CN117106004A (zh) * 2022-05-17 2023-11-24 北京科兴中维生物技术有限公司 三萜皂苷化合物及其制备方法及应用
EP4698224A1 (en) 2023-04-20 2026-02-25 Asociación Centro de Investigación Cooperativa en Biociencias - CIC bioGUNE Saponin derivatives as adjuvants and photoaffinity probes
WO2024261351A2 (en) 2024-05-08 2024-12-26 Vaccine Formulation Institute Ch Ltd. Immunologically active saponin fractions and adjuvant formulations

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102112484A (zh) * 2008-04-08 2011-06-29 索隆-基特林癌症研究协会 三萜皂苷、其合成方法和用途

Family Cites Families (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5341202B2 (https=) 1974-03-12 1978-11-01
US5916588A (en) 1984-04-12 1999-06-29 The Liposome Company, Inc. Peptide-containing liposomes, immunogenic liposomes and methods of preparation and use
US5231112A (en) 1984-04-12 1993-07-27 The Liposome Company, Inc. Compositions containing tris salt of cholesterol hemisuccinate and antifungal
US4769239A (en) 1984-08-21 1988-09-06 Merck & Co., Inc. Vaccine against varicella-zoster virus
US4684479A (en) 1985-08-14 1987-08-04 Arrigo Joseph S D Surfactant mixtures, stable gas-in-liquid emulsions, and methods for the production of such emulsions from said mixtures
US6759057B1 (en) 1986-06-12 2004-07-06 The Liposome Company, Inc. Methods and compositions using liposome-encapsulated non-steroidal anti-inflammatory drugs
IE60901B1 (en) 1986-08-21 1994-08-24 Vestar Inc Improved treatment of systemic fungal infections with phospholipid particles encapsulating polyene antifungal antibiotics
US6406713B1 (en) 1987-03-05 2002-06-18 The Liposome Company, Inc. Methods of preparing low-toxicity drug-lipid complexes
US5583112A (en) 1987-05-29 1996-12-10 Cambridge Biotech Corporation Saponin-antigen conjugates and the use thereof
AU598958B2 (en) 1987-11-12 1990-07-05 Vestar, Inc. Improved amphotericin b liposome preparation
US5215680A (en) 1990-07-10 1993-06-01 Cavitation-Control Technology, Inc. Method for the production of medical-grade lipid-coated microbubbles, paramagnetic labeling of such microbubbles and therapeutic uses of microbubbles
WO1994002596A1 (en) 1992-07-17 1994-02-03 Merck & Co., Inc. Method for preventing zoster or alleviating varicella related post-herpetic neuralgia
UA56132C2 (uk) 1995-04-25 2003-05-15 Смітклайн Бічем Байолоджікалс С.А. Композиція вакцини (варіанти), спосіб стабілізації qs21 відносно гідролізу (варіанти), спосіб приготування композиції вакцини
ATE252372T1 (de) 1996-08-23 2003-11-15 Sequus Pharm Inc Liposome enthaltend cisplatin
JP2001503396A (ja) 1996-10-11 2001-03-13 アルザ コーポレイション 治療用リポソーム組成物および方法
US6056973A (en) 1996-10-11 2000-05-02 Sequus Pharmaceuticals, Inc. Therapeutic liposome composition and method of preparation
HUP0000522A3 (en) 1996-10-15 2000-10-30 Transave Inc Monmouth Junction N-acyl phoshpatidylethanolamine-mediated liposomal drug delivery
US6080725A (en) * 1997-05-20 2000-06-27 Galenica Pharmaceuticals, Inc. Immunostimulating and vaccine compositions employing saponin analog adjuvants and uses thereof
AU1145699A (en) 1997-09-05 1999-03-22 Smithkline Beecham Biologicals (Sa) Oil in water emulsions containing saponins
WO2000009075A2 (en) * 1998-08-14 2000-02-24 Galenica Pharmaceuticals, Inc. Chemically modified saponins and the use thereof as adjuvants
AU7085400A (en) 1999-09-02 2001-03-26 Antigenics, Inc. Compositions of immunostimulatory polymers and saponin adjuvants and uses thereof
GB0401239D0 (en) 2004-01-21 2004-02-25 Molecularnature Ltd Adjuvant compositions
GB0504436D0 (en) 2005-03-03 2005-04-06 Glaxosmithkline Biolog Sa Vaccine
TWI457133B (zh) 2005-12-13 2014-10-21 Glaxosmithkline Biolog Sa 新穎組合物
GB0700562D0 (en) * 2007-01-11 2007-02-21 Novartis Vaccines & Diagnostic Modified Saccharides
JP5331105B2 (ja) 2007-05-24 2013-10-30 グラクソスミスクライン バイオロジカルズ ソシエテ アノニム 凍結乾燥抗原組成物
AU2008339980A1 (en) 2007-12-21 2009-07-02 Glaxosmithkline Biologicals S.A. Vaccines for malaria
ES2553113T3 (es) 2008-04-16 2015-12-04 Glaxosmithkline Biologicals S.A. Vacuna
GB0910046D0 (en) 2009-06-10 2009-07-22 Glaxosmithkline Biolog Sa Novel compositions
WO2011027222A2 (en) 2009-09-02 2011-03-10 Novartis Ag Immunogenic compositions including tlr activity modulators
CN103533953A (zh) 2011-05-17 2014-01-22 葛兰素史密丝克莱恩生物有限公司 针对肺炎链球菌的疫苗
US20130309273A1 (en) 2012-05-17 2013-11-21 Kimberly Hassett Thermostable Vaccine Compositions and Methods of Preparing Same
CN107625958A (zh) 2011-05-17 2018-01-26 索利吉尼克斯公司 热稳定性疫苗组合物及其制备方法
WO2014124860A1 (en) 2013-02-14 2014-08-21 Boehringer Ingelheim International Gmbh Specific pde4b-inhibitors for the treatment of diabetes mellitus
US20150037374A1 (en) 2013-07-31 2015-02-05 Csl Limited Anti-tumor compositions and uses thereof
KR102424785B1 (ko) * 2014-05-30 2022-07-25 메모리얼 슬로안 케터링 캔서 센터 최소 사포닌 유사체, 이의 합성법 및 용도
EP3233118A1 (en) 2014-12-18 2017-10-25 GlaxoSmithKline Biologicals S.A. Vaccination
CN108778289B (zh) 2015-11-06 2020-11-17 佐剂技术公司 三萜皂苷类似物
ES2944947T3 (es) 2015-12-17 2023-06-27 Memorial Sloan Kettering Cancer Center Variantes de triterpeno-saponina, métodos de síntesis y uso de las mismas
GB201621686D0 (en) 2016-12-20 2017-02-01 Glaxosmithkline Biologicals Sa Novel methods for inducing an immune response
WO2018191598A1 (en) 2017-04-13 2018-10-18 Adjuvance Technologies, Inc. Triterpene saponin synthesis, intermediates and adjuvant combinations
US20200164065A1 (en) 2017-04-25 2020-05-28 Adjuvance Technologies, Inc. Triterpene saponin analogues
CA3061205A1 (en) 2017-04-25 2018-11-01 Memorial Sloan Kettering Cancer Center Triterpene saponin analogues
WO2019051149A1 (en) 2017-09-08 2019-03-14 Infectious Disease Research Institute LIPOSOMAL FORMULATIONS COMPRISING SAPONIN AND METHODS OF USE
SG11202001826YA (en) 2017-10-16 2020-03-30 Adjuvance Technologies Inc Triterpene saponin analogues
WO2019175147A1 (en) 2018-03-12 2019-09-19 Janssen Vaccines & Prevention B.V. Vaccines against intra-abdominal infections
IL292796A (en) 2019-11-05 2022-07-01 Adjuvance Tech Inc Varicella zoster immunogenic compositions and uses thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102112484A (zh) * 2008-04-08 2011-06-29 索隆-基特林癌症研究协会 三萜皂苷、其合成方法和用途
CN104710487A (zh) * 2008-04-08 2015-06-17 索隆-基特林癌症研究协会 三萜皂苷、其合成方法和用途

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EP3370730A1 (en) 2018-09-12
ZA201802891B (en) 2020-01-29
CN112812143A (zh) 2021-05-18
AU2016349693A1 (en) 2018-05-17
SG11201803594TA (en) 2018-05-30
US20230219991A1 (en) 2023-07-13
CA3003483A1 (en) 2017-05-11
IL293848B1 (en) 2024-10-01
IL293848A (en) 2022-08-01
IL259145A (en) 2018-06-28
IL286493A (en) 2021-10-31
US10906926B2 (en) 2021-02-02
KR20180077180A (ko) 2018-07-06
EP3370730A4 (en) 2019-07-31
WO2017079582A1 (en) 2017-05-11
US20180327436A1 (en) 2018-11-15
US20240327443A1 (en) 2024-10-03
JP6900385B2 (ja) 2021-07-07
SG10202012205XA (en) 2021-01-28
CL2018001192A1 (es) 2018-11-23
JP2021152043A (ja) 2021-09-30
JP2023012519A (ja) 2023-01-25
US20210002316A1 (en) 2021-01-07
IL259145B (en) 2021-09-30
IL293848B2 (en) 2025-02-01
AU2016349693B2 (en) 2022-08-11
CN108778289A (zh) 2018-11-09
IL286493B (en) 2022-07-01
EP4001290A1 (en) 2022-05-25
US12037355B2 (en) 2024-07-16
US20200239509A1 (en) 2020-07-30
CA3003483C (en) 2022-09-13
JP2018537527A (ja) 2018-12-20

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