IL293848B2 - Triterpene saponin analogues, methods for their production, compositions containing them and uses thereof - Google Patents

Triterpene saponin analogues, methods for their production, compositions containing them and uses thereof

Info

Publication number
IL293848B2
IL293848B2 IL293848A IL29384822A IL293848B2 IL 293848 B2 IL293848 B2 IL 293848B2 IL 293848 A IL293848 A IL 293848A IL 29384822 A IL29384822 A IL 29384822A IL 293848 B2 IL293848 B2 IL 293848B2
Authority
IL
Israel
Prior art keywords
group
nitrogen
oxygen
sulfur
independently selected
Prior art date
Application number
IL293848A
Other languages
English (en)
Hebrew (he)
Other versions
IL293848A (en
IL293848B1 (en
Original Assignee
Adjuvance Tech Inc
Memorial Sloan Kettering Cancer Center
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Adjuvance Tech Inc, Memorial Sloan Kettering Cancer Center filed Critical Adjuvance Tech Inc
Publication of IL293848A publication Critical patent/IL293848A/en
Publication of IL293848B1 publication Critical patent/IL293848B1/en
Publication of IL293848B2 publication Critical patent/IL293848B2/en

Links

Classifications

    • 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
    • C07H1/00—Processes for the preparation of sugar derivatives
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Immunology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (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)
IL293848A 2015-11-06 2016-11-04 Triterpene saponin analogues, methods for their production, compositions containing them and uses thereof IL293848B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562252296P 2015-11-06 2015-11-06
US201562268837P 2015-12-17 2015-12-17
PCT/US2016/060564 WO2017079582A1 (en) 2015-11-06 2016-11-04 Triterpene saponin analogues

Publications (3)

Publication Number Publication Date
IL293848A IL293848A (en) 2022-08-01
IL293848B1 IL293848B1 (en) 2024-10-01
IL293848B2 true IL293848B2 (en) 2025-02-01

Family

ID=58662549

Family Applications (3)

Application Number Title Priority Date Filing Date
IL293848A IL293848B2 (en) 2015-11-06 2016-11-04 Triterpene saponin analogues, methods for their production, compositions containing them and uses thereof
IL286493A IL286493B (en) 2015-11-06 2016-11-04 Triterpene saponin analogues, methods of producing same, compositions comprising same and uses thereof
IL259145A IL259145B (en) 2015-11-06 2018-05-03 Triterpene saponin analogs, methods for their production, preparations containing them and their uses

Family Applications After (2)

Application Number Title Priority Date Filing Date
IL286493A IL286493B (en) 2015-11-06 2016-11-04 Triterpene saponin analogues, methods of producing same, compositions comprising same and uses thereof
IL259145A IL259145B (en) 2015-11-06 2018-05-03 Triterpene saponin analogs, methods for their production, preparations containing them and their uses

Country Status (12)

Country Link
US (5) US20180327436A1 (enExample)
EP (2) EP4001290A1 (enExample)
JP (3) JP6900385B2 (enExample)
KR (1) KR20180077180A (enExample)
CN (2) CN112812143A (enExample)
AU (1) AU2016349693B2 (enExample)
CA (1) CA3003483C (enExample)
CL (1) CL2018001192A1 (enExample)
IL (3) IL293848B2 (enExample)
SG (2) SG10202012205XA (enExample)
WO (1) WO2017079582A1 (enExample)
ZA (1) ZA201802891B (enExample)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106573951B (zh) * 2014-05-30 2020-09-11 索隆-基特林癌症研究协会 微小皂苷类似物、合成及其用途
JP6900385B2 (ja) 2015-11-06 2021-07-07 アジュバンス・テクノロジーズ・インコーポレーテッド トリテルペンサポニン類似物
KR20190137808A (ko) * 2017-04-13 2019-12-11 아쥬반스 테크놀로지스 인코포레이티드 트리테르펜 사포닌, 중간체 및 보조제 배합물
CN110730666A (zh) * 2017-04-25 2020-01-24 佐剂技术公司 三萜皂苷类似物
SG11201909584QA (en) * 2017-04-25 2019-11-28 Adjuvance Technologies Inc Triterpene saponin analogues
AU2018350887A1 (en) * 2017-10-16 2020-03-05 Adjuvance Technologies, Inc. Triterpene saponin analogues
WO2021195024A1 (en) * 2020-03-23 2021-09-30 Adjuvance Technologies, Inc. Adjuvant compounds, salt forms, and formulations
CN115867304A (zh) 2020-05-19 2023-03-28 欧萨尔普罗席纳有限公司 用于治疗阿兹海默症的多抗原决定基疫苗
EP4192497A4 (en) 2020-08-07 2024-08-21 Othair Prothena Limited MULTI-EPITOPIC 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
US20250025550A1 (en) * 2021-11-08 2025-01-23 Adjuvance Technologies, 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
WO2024218268A1 (en) 2023-04-20 2024-10-24 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
US20150086585A1 (en) * 2008-04-08 2015-03-26 Memorial Sloan-Kettering Institute For Cancer Research Triterpene saponins, methods of synthesis and uses thereof

Family Cites Families (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5341202B2 (enExample) 1974-03-12 1978-11-01
US5231112A (en) 1984-04-12 1993-07-27 The Liposome Company, Inc. Compositions containing tris salt of cholesterol hemisuccinate and antifungal
US5916588A (en) 1984-04-12 1999-06-29 The Liposome Company, Inc. Peptide-containing liposomes, immunogenic liposomes and methods of preparation and use
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
AU687355B2 (en) 1992-07-17 1998-02-26 Merck Sharp & Dohme Corp. 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
DK0929293T3 (da) 1996-08-23 2004-02-02 Sequus Pharm Inc Liposomer indeholdende en cisplatinforbindelse
EP0932390A1 (en) 1996-10-11 1999-08-04 Sequus Pharmaceuticals, Inc. Therapeutic liposome composition and method
US6056973A (en) 1996-10-11 2000-05-02 Sequus Pharmaceuticals, Inc. Therapeutic liposome composition and method of preparation
SK283760B6 (sk) 1996-10-15 2004-01-08 The Liposome Company, Inc. Farmaceutický prostriedok na dopravu bioaktívnych látok
US6080725A (en) * 1997-05-20 2000-06-27 Galenica Pharmaceuticals, Inc. Immunostimulating and vaccine compositions employing saponin analog adjuvants and uses thereof
EP1279401B1 (en) 1997-09-05 2008-01-09 GlaxoSmithKline Biologicals S.A. Oil in water emulsions containing saponins
US6262029B1 (en) * 1998-08-14 2001-07-17 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
UY31101A1 (es) 2007-05-24 2009-01-05 Glaxosmithkline Biologicals Sa Composición antigénica liofilizada
EP2234637A2 (en) 2007-12-21 2010-10-06 GlaxoSmithKline Biologicals S.A. Vaccines for malaria
HUE026586T2 (hu) 2008-04-16 2016-06-28 Glaxosmithkline Biologicals Sa Vakcina
GB0910046D0 (en) 2009-06-10 2009-07-22 Glaxosmithkline Biolog Sa Novel compositions
CN102844047B (zh) 2009-09-02 2017-04-05 诺华股份有限公司 含tlr活性调节剂的免疫原性组合物
CN103781491A (zh) 2011-05-17 2014-05-07 索利吉尼克斯公司 热稳定性疫苗组合物及其制备方法
CA2834834A1 (en) 2011-05-17 2012-11-22 Glaxosmithkline Biologicals S.A. Vaccine against streptococcus pneumoniae
US20130309273A1 (en) 2012-05-17 2013-11-21 Kimberly Hassett Thermostable Vaccine Compositions and Methods of Preparing Same
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
CN106573951B (zh) * 2014-05-30 2020-09-11 索隆-基特林癌症研究协会 微小皂苷类似物、合成及其用途
WO2016096968A1 (en) 2014-12-18 2016-06-23 Glaxosmithkline Biologicals S.A. Vaccination
JP6900385B2 (ja) 2015-11-06 2021-07-07 アジュバンス・テクノロジーズ・インコーポレーテッド トリテルペンサポニン類似物
EP3389669B1 (en) 2015-12-17 2023-03-15 Memorial Sloan-Kettering Cancer Center Triterpene saponin variants, methods of synthesis and use thereof
GB201621686D0 (en) 2016-12-20 2017-02-01 Glaxosmithkline Biologicals Sa Novel methods for inducing an immune response
KR20190137808A (ko) 2017-04-13 2019-12-11 아쥬반스 테크놀로지스 인코포레이티드 트리테르펜 사포닌, 중간체 및 보조제 배합물
CN110730666A (zh) 2017-04-25 2020-01-24 佐剂技术公司 三萜皂苷类似物
SG11201909584QA (en) 2017-04-25 2019-11-28 Adjuvance Technologies Inc Triterpene saponin analogues
US20200276299A1 (en) 2017-09-08 2020-09-03 Infectious Disease Research Institute Liposomal formulations comprising saponin and methods of use
AU2018350887A1 (en) 2017-10-16 2020-03-05 Adjuvance Technologies, Inc. Triterpene saponin analogues
TW202003023A (zh) 2018-03-12 2020-01-16 美商詹森藥物公司 針對尿路感染之疫苗
AU2020379738A1 (en) 2019-11-05 2022-04-14 Adjuvance Technologies, Inc. Varicella zoster

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150086585A1 (en) * 2008-04-08 2015-03-26 Memorial Sloan-Kettering Institute For Cancer Research Triterpene saponins, methods of synthesis and uses thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ALBERTO FERN?NDEZ-TEJADA ET AL,, DEVELOPMENT OF A MINIMAL SAPONIN VACCINE ADJUVANT BASED ON QS-21 (SUPPLEMENTARY INFORMATION), 1 June 2014 (2014-06-01) *

Also Published As

Publication number Publication date
IL286493A (en) 2021-10-31
EP3370730A4 (en) 2019-07-31
US20210002316A1 (en) 2021-01-07
CN112812143A (zh) 2021-05-18
ZA201802891B (en) 2020-01-29
IL259145A (en) 2018-06-28
EP3370730A1 (en) 2018-09-12
WO2017079582A1 (en) 2017-05-11
CA3003483C (en) 2022-09-13
IL259145B (en) 2021-09-30
JP2018537527A (ja) 2018-12-20
SG10202012205XA (en) 2021-01-28
AU2016349693B2 (en) 2022-08-11
CL2018001192A1 (es) 2018-11-23
KR20180077180A (ko) 2018-07-06
IL286493B (en) 2022-07-01
IL293848A (en) 2022-08-01
EP4001290A1 (en) 2022-05-25
CA3003483A1 (en) 2017-05-11
US20240327443A1 (en) 2024-10-03
SG11201803594TA (en) 2018-05-30
CN108778289B (zh) 2020-11-17
JP2023012519A (ja) 2023-01-25
US20180327436A1 (en) 2018-11-15
CN108778289A (zh) 2018-11-09
US10906926B2 (en) 2021-02-02
US12037355B2 (en) 2024-07-16
JP6900385B2 (ja) 2021-07-07
IL293848B1 (en) 2024-10-01
US20200239509A1 (en) 2020-07-30
US20230219991A1 (en) 2023-07-13
JP2021152043A (ja) 2021-09-30
AU2016349693A1 (en) 2018-05-17

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