CA2993582C - Triterpene saponins, methods of synthesis, and uses thereof - Google Patents

Triterpene saponins, methods of synthesis, and uses thereof Download PDF

Info

Publication number
CA2993582C
CA2993582C CA2993582A CA2993582A CA2993582C CA 2993582 C CA2993582 C CA 2993582C CA 2993582 A CA2993582 A CA 2993582A CA 2993582 A CA2993582 A CA 2993582A CA 2993582 C CA2993582 C CA 2993582C
Authority
CA
Canada
Prior art keywords
optionally substituted
nitrogen
oxygen
sulfur
group
Prior art date
Legal status (The legal status 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 status listed.)
Active
Application number
CA2993582A
Other languages
English (en)
French (fr)
Other versions
CA2993582A1 (en
Inventor
David Gin
Michelle Adams
Kai DENG
Nicholas Perl
Annie Won
Philip Livingston
Govind Ragupathi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Memorial Sloan Kettering Cancer Center
Original Assignee
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 Memorial Sloan Kettering Cancer Center filed Critical Memorial Sloan Kettering Cancer Center
Priority to CA3096084A priority Critical patent/CA3096084C/en
Publication of CA2993582A1 publication Critical patent/CA2993582A1/en
Application granted granted Critical
Publication of CA2993582C publication Critical patent/CA2993582C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07H15/256—Polyterpene radicals
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
    • 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
    • A61K31/74—Synthetic polymeric materials
    • A61K31/80—Polymers containing hetero atoms not provided for in groups A61K31/755 - A61K31/795
    • 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
    • A61K39/385—Haptens or antigens, bound to carriers
    • 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
    • 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
    • A61P31/14—Antivirals for RNA viruses
    • 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
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
    • 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
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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
    • 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
    • A61P31/22—Antivirals for DNA viruses for herpes viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • 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
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
    • C07H5/06—Aminosugars
    • 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)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Virology (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Epidemiology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Immunology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • AIDS & HIV (AREA)
  • Pulmonology (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)
  • Pyrane Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines Containing Plant Substances (AREA)
CA2993582A 2008-04-08 2009-04-08 Triterpene saponins, methods of synthesis, and uses thereof Active CA2993582C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3096084A CA3096084C (en) 2008-04-08 2009-04-08 Triterpene saponins, methods of synthesis, and uses thereof

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US4319708P 2008-04-08 2008-04-08
US61/043,197 2008-04-08
CA2720771A CA2720771C (en) 2008-04-08 2009-04-08 Triterpene saponins, methods of synthesis, and uses thereof

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA2720771A Division CA2720771C (en) 2008-04-08 2009-04-08 Triterpene saponins, methods of synthesis, and uses thereof

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA3096084A Division CA3096084C (en) 2008-04-08 2009-04-08 Triterpene saponins, methods of synthesis, and uses thereof

Publications (2)

Publication Number Publication Date
CA2993582A1 CA2993582A1 (en) 2009-10-15
CA2993582C true CA2993582C (en) 2020-12-15

Family

ID=40875147

Family Applications (3)

Application Number Title Priority Date Filing Date
CA2993582A Active CA2993582C (en) 2008-04-08 2009-04-08 Triterpene saponins, methods of synthesis, and uses thereof
CA3096084A Active CA3096084C (en) 2008-04-08 2009-04-08 Triterpene saponins, methods of synthesis, and uses thereof
CA2720771A Active CA2720771C (en) 2008-04-08 2009-04-08 Triterpene saponins, methods of synthesis, and uses thereof

Family Applications After (2)

Application Number Title Priority Date Filing Date
CA3096084A Active CA3096084C (en) 2008-04-08 2009-04-08 Triterpene saponins, methods of synthesis, and uses thereof
CA2720771A Active CA2720771C (en) 2008-04-08 2009-04-08 Triterpene saponins, methods of synthesis, and uses thereof

Country Status (11)

Country Link
US (6) US8283456B2 (enExample)
EP (3) EP3357931B1 (enExample)
JP (5) JP5706815B2 (enExample)
KR (6) KR102453184B1 (enExample)
CN (2) CN102112484B (enExample)
AU (1) AU2009233757B2 (enExample)
CA (3) CA2993582C (enExample)
ES (1) ES2827804T3 (enExample)
HK (1) HK1211591A1 (enExample)
IL (4) IL208535A (enExample)
WO (1) WO2009126737A2 (enExample)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102453184B1 (ko) 2008-04-08 2022-10-07 슬로안-케테링인스티튜트퍼캔서리서치 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도
CN102068446B (zh) * 2011-01-10 2013-08-21 武汉道一堂医药研究院 三萜皂苷化合物在制备抗病原微生物药物中的应用
AU2013204005B2 (en) * 2012-05-23 2015-04-16 Oncology Research International Limited Improved synthesis
US10517936B2 (en) 2013-01-04 2019-12-31 OBI Pharma., Inc. Vaccines with higher carbohydrate antigen density and novel saponin adjuvant
US10806119B2 (en) 2013-06-05 2020-10-20 Yeda Research And Development Co. Ltd. Plant with altered content of steroidal alkaloids
ES2914176T3 (es) 2013-09-17 2022-06-07 Obi Pharma Inc Composiciones de una vacuna glucídica para inducir respuestas inmunitarias y usos de las mismas en el tratamiento de cáncer
CA2950750C (en) 2014-05-30 2023-01-10 David Y. Gin Minimal saponin analogues, synthesis and use thereof
US10676723B2 (en) 2015-05-11 2020-06-09 David Gordon Bermudes Chimeric protein toxins for expression by therapeutic bacteria
KR20180050339A (ko) 2015-09-04 2018-05-14 오비아이 파머 인코퍼레이티드 글리칸 어레이 및 사용 방법
US20180327436A1 (en) 2015-11-06 2018-11-15 Adjuvance Technologies, Inc. Triterpene saponin analogues
US10980894B2 (en) 2016-03-29 2021-04-20 Obi Pharma, Inc. Antibodies, pharmaceutical compositions and methods
EP3436482A4 (en) 2016-03-29 2020-03-11 OBI Pharma, Inc. ANTIBODIES, PHARMACEUTICAL COMPOSITIONS AND METHODS
JP7544465B2 (ja) 2016-04-22 2024-09-03 オービーアイ ファーマ，インコーポレイテッド グロボシリーズの抗原を介した免疫活性化又は免疫調節によるがん免疫療法
KR20190067765A (ko) 2016-07-27 2019-06-17 오비아이 파머 인코퍼레이티드 면역원성/치료 글리칸 조성물 및 그의 용도
TWI786054B (zh) 2016-07-29 2022-12-11 台灣浩鼎生技股份有限公司 人類抗體、醫藥組合物、及其方法
KR20190077103A (ko) 2016-11-21 2019-07-02 오비아이 파머 인코퍼레이티드 접합된 생물학적 분자, 제약 조성물 및 방법
US11129906B1 (en) 2016-12-07 2021-09-28 David Gordon Bermudes Chimeric protein toxins for expression by therapeutic bacteria
CN110869025A (zh) * 2017-04-13 2020-03-06 佐剂技术公司 三萜皂苷合成、中间体和佐剂组合
SG10202108075YA (en) * 2017-04-25 2021-09-29 Adjuvance Technologies Inc Triterpene saponin analogues
US20200164065A1 (en) * 2017-04-25 2020-05-28 Adjuvance Technologies, Inc. Triterpene saponin analogues
US11324821B2 (en) 2017-10-16 2022-05-10 Adjuvance Technologies, Inc. Triterpene saponin analogues
JP7304863B2 (ja) 2017-12-29 2023-07-07 グリコミメティクス， インコーポレイテッド Ｅ－セレクチンおよびガレクチン－３のヘテロ二機能性阻害剤
US12497429B2 (en) * 2018-03-20 2025-12-16 The Uab Research Foundation Saponin-based vaccine adjuvants
US11203645B2 (en) 2018-06-27 2021-12-21 Obi Pharma, Inc. Glycosynthase variants for glycoprotein engineering and methods of use
CN112969785A (zh) 2018-09-06 2021-06-15 耶达研究及发展有限公司 纤维素合酶样酶及其用途
US11547672B2 (en) 2018-09-14 2023-01-10 Massachusetts Institute Of Technology Nanoparticle vaccine adjuvant and methods of use thereof
US11845771B2 (en) 2018-12-27 2023-12-19 Glycomimetics, Inc. Heterobifunctional inhibitors of E-selectin and galectin-3
AU2019416330A1 (en) 2018-12-27 2021-07-01 Glycomimetics, Inc. Galectin-3 inhibiting c-glycosides
US20220409721A1 (en) * 2019-11-05 2022-12-29 Adjuvance Technologies, Inc. Varicella zoster
US20230128815A1 (en) * 2020-03-23 2023-04-27 Adjuvance Technologies, Inc. Adjuvant compounds, salt forms, and formulations
WO2023052829A1 (en) * 2021-10-02 2023-04-06 Desert King Chile S.A A 3-o-monodesmosidic saponins extract, stable at physiological ph, method for preparing it from a quillaja plant extract cultured with a microbial consortium, uses and such microbial consortium
EP4190359A1 (en) 2021-12-03 2023-06-07 Asociación Centro de Investigación Cooperativa en Biociencias - CIC bioGUNE Saponin-based adjuvants and vaccines
US20230190920A1 (en) 2021-12-19 2023-06-22 Massachusetts Institute Of Technology Compositions and methods for long-lasting germinal center responses to a priming immunization
WO2023139145A1 (en) 2022-01-19 2023-07-27 Asociación Centro De Investigación Cooperativa En Biociencias-Cic Biogune Saponin-based adjuvants and vaccines
WO2024218268A1 (en) 2023-04-20 2024-10-24 Asociación Centro De Investigación Cooperativa En Biociencias-Cic Biogune Saponin derivatives as adjuvants and photoaffinity probes

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6112695A (ja) * 1984-06-28 1986-01-21 Rikagaku Kenkyusho シアル酸誘導体
US5583112A (en) 1987-05-29 1996-12-10 Cambridge Biotech Corporation Saponin-antigen conjugates and the use thereof
US5057540A (en) * 1987-05-29 1991-10-15 Cambridge Biotech Corporation Saponin adjuvant
JPH09169648A (ja) * 1995-12-22 1997-06-30 Nippon Shinyaku Co Ltd 医薬組成物
US6231859B1 (en) 1996-12-02 2001-05-15 Aquila Biopharmaceuticals, Inc. Saponin adjuvant compositions
DE69637435T2 (de) * 1996-12-02 2009-02-19 Antigenics Inc. Saponin-zusammensetzungen und deren verwendung
AU732856B2 (en) 1997-05-20 2001-05-03 Galenica Pharmaceuticals, Inc. Triterpene saponin analogs having adjuvant and immunostimulatory activity
US6080725A (en) 1997-05-20 2000-06-27 Galenica Pharmaceuticals, Inc. Immunostimulating and vaccine compositions employing saponin analog adjuvants and uses thereof
WO1998056415A1 (en) * 1997-06-11 1998-12-17 Aquila Biopharmaceuticals, Inc. Purified saponins as oral adjuvants
WO2000009075A2 (en) 1998-08-14 2000-02-24 Galenica Pharmaceuticals, Inc. Chemically modified saponins and the use thereof as adjuvants
US7457415B2 (en) 1998-08-20 2008-11-25 Akikaze Technologies, Llc Secure information distribution system utilizing information segment scrambling
US6716428B1 (en) 1999-10-06 2004-04-06 The Ohio State University Research Foundation Antigenic modification of polypeptides
WO2004092329A2 (en) 2003-04-08 2004-10-28 Galenica Pharmaceuticals, Inc. Semi-synthetic saponin analogs with carrier and immune stimulatory activities for dna and rna vaccines
CA2606992A1 (en) * 2005-05-04 2006-11-09 National Research Council Of Canada Method for production of saponaria from microspores
CN100335073C (zh) * 2005-08-19 2007-09-05 浙江大学 木鳖子含三萜皂甙成分提取物的制备方法
KR102453184B1 (ko) * 2008-04-08 2022-10-07 슬로안-케테링인스티튜트퍼캔서리서치 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도
CN101322734B (zh) 2008-07-22 2013-05-29 沈阳药科大学 具有抗炎免疫作用的轮叶党参总皂苷及其制备方法
CA2950750C (en) * 2014-05-30 2023-01-10 David Y. Gin Minimal saponin analogues, synthesis and use thereof

Also Published As

Publication number Publication date
US8889842B2 (en) 2014-11-18
KR101825315B1 (ko) 2018-02-02
JP6786410B2 (ja) 2020-11-18
EP3868771A1 (en) 2021-08-25
CA3096084C (en) 2022-12-20
WO2009126737A3 (en) 2010-01-14
IL208535A (en) 2015-06-30
ES2827804T3 (es) 2021-05-24
AU2009233757B2 (en) 2015-05-07
JP2011516566A (ja) 2011-05-26
IL208535A0 (en) 2010-12-30
US20130011421A1 (en) 2013-01-10
JP2015134793A (ja) 2015-07-27
KR101651695B1 (ko) 2016-08-26
CN102112484A (zh) 2011-06-29
CA3096084A1 (en) 2009-10-15
KR102453184B1 (ko) 2022-10-07
IL237505A0 (en) 2015-04-30
WO2009126737A2 (en) 2009-10-15
KR101947332B1 (ko) 2019-02-12
CA2720771A1 (en) 2009-10-15
KR20210062717A (ko) 2021-05-31
KR20190016595A (ko) 2019-02-18
IL281261A (en) 2021-04-29
US8283456B2 (en) 2012-10-09
KR102085687B1 (ko) 2020-03-06
JP6770596B2 (ja) 2020-10-14
US20110300177A1 (en) 2011-12-08
IL237505A (en) 2017-06-29
KR20200024964A (ko) 2020-03-09
KR102256410B1 (ko) 2021-05-26
KR20160103156A (ko) 2016-08-31
US20150086585A1 (en) 2015-03-26
IL239051B (en) 2021-03-25
EP3357931B1 (en) 2020-07-22
EP2280987B1 (en) 2018-05-23
US20230131867A1 (en) 2023-04-27
JP5706815B2 (ja) 2015-04-22
US12227535B2 (en) 2025-02-18
CA2993582A1 (en) 2009-10-15
JP2017114876A (ja) 2017-06-29
US9718850B2 (en) 2017-08-01
IL281261B2 (en) 2023-03-01
IL239051A0 (en) 2015-07-30
IL281261B (en) 2022-11-01
EP3357931A1 (en) 2018-08-08
JP2020169206A (ja) 2020-10-15
US20170283450A1 (en) 2017-10-05
US20250188109A1 (en) 2025-06-12
JP2019073530A (ja) 2019-05-16
KR20110003523A (ko) 2011-01-12
CN102112484B (zh) 2015-03-04
AU2009233757A1 (en) 2009-10-15
CA2720771C (en) 2018-03-20
CN104710487A (zh) 2015-06-17
US11447515B2 (en) 2022-09-20
EP2280987A2 (en) 2011-02-09
HK1211591A1 (en) 2016-05-27
KR20180014211A (ko) 2018-02-07

Similar Documents

Publication Publication Date Title
US12227535B2 (en) Triterpene saponins, methods of synthesis and uses thereof
AU2021266246B2 (en) Triterpene saponins, methods of synthesis, and uses thereof
HK40061427A (en) Triterpene saponins, methods of synthesis, and uses thereof
HK1259568B (en) Methods of synthesis of triterpene prosapogenins and triterpene saponins
HK1259568A1 (en) Methods of synthesis of triterpene prosapogenins and triterpene saponins
HK1153746A (en) Triterpene saponins, methods of synthesis, and uses thereof
HK1153746B (en) Triterpene saponins, methods of synthesis, and uses thereof

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20180131