AU2009233757B2 - Triterpene saponins, methods of synthesis, and uses thereof - Google Patents

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

Info

Publication number
AU2009233757B2
AU2009233757B2 AU2009233757A AU2009233757A AU2009233757B2 AU 2009233757 B2 AU2009233757 B2 AU 2009233757B2 AU 2009233757 A AU2009233757 A AU 2009233757A AU 2009233757 A AU2009233757 A AU 2009233757A AU 2009233757 B2 AU2009233757 B2 AU 2009233757B2
Authority
AU
Australia
Prior art keywords
group
bno
nitrogen
oxygen
sulfur
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
AU2009233757A
Other languages
English (en)
Other versions
AU2009233757A1 (en
Inventor
Michelle Adams
Kai DENG
David Gin
Philip Livingston
Nicholas Perl
Govind Ragupathi
Annie Won
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
Publication of AU2009233757A1 publication Critical patent/AU2009233757A1/en
Application granted granted Critical
Publication of AU2009233757B2 publication Critical patent/AU2009233757B2/en
Priority to AU2015203675A priority Critical patent/AU2015203675B2/en
Priority to AU2017258850A priority patent/AU2017258850B2/en
Priority to AU2018201645A priority patent/AU2018201645B2/en
Priority to AU2020202692A priority patent/AU2020202692B2/en
Priority to AU2021266246A priority patent/AU2021266246B2/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
    • 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
    • C07H15/256—Polyterpene radicals
    • 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)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Virology (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Epidemiology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Immunology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • AIDS & HIV (AREA)
  • Pulmonology (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Steroid Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
AU2009233757A 2008-04-08 2009-04-08 Triterpene saponins, methods of synthesis, and uses thereof Active AU2009233757B2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU2015203675A AU2015203675B2 (en) 2008-04-08 2015-06-30 Triterpene saponins, methods of synthesis, and uses thereof
AU2017258850A AU2017258850B2 (en) 2008-04-08 2017-11-07 Triterpene saponins, methods of synthesis, and uses thereof
AU2018201645A AU2018201645B2 (en) 2008-04-08 2018-03-07 Triterpene saponins, methods of synthesis, and uses thereof
AU2020202692A AU2020202692B2 (en) 2008-04-08 2020-04-22 Triterpene saponins, methods of synthesis, and uses thereof
AU2021266246A AU2021266246B2 (en) 2008-04-08 2021-11-10 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
PCT/US2009/039954 WO2009126737A2 (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
AU2015203675A Division AU2015203675B2 (en) 2008-04-08 2015-06-30 Triterpene saponins, methods of synthesis, and uses thereof

Publications (2)

Publication Number Publication Date
AU2009233757A1 AU2009233757A1 (en) 2009-10-15
AU2009233757B2 true AU2009233757B2 (en) 2015-05-07

Family

ID=40875147

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2009233757A Active AU2009233757B2 (en) 2008-04-08 2009-04-08 Triterpene saponins, methods of synthesis, and uses thereof

Country Status (11)

Country Link
US (6) US8283456B2 (https=)
EP (3) EP3868771A1 (https=)
JP (5) JP5706815B2 (https=)
KR (6) KR101651695B1 (https=)
CN (2) CN104710487A (https=)
AU (1) AU2009233757B2 (https=)
CA (3) CA3096084C (https=)
ES (1) ES2827804T3 (https=)
HK (1) HK1211591A1 (https=)
IL (4) IL208535A (https=)
WO (1) WO2009126737A2 (https=)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5706815B2 (ja) 2008-04-08 2015-04-22 スローン − ケタリング・インスティテュート・フォー・キャンサー・リサーチ トリテルペンであるサポニン、その合成法および使用
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
EP3792272A1 (en) 2013-01-04 2021-03-17 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
AU2014391422A1 (en) 2013-09-17 2015-12-17 Obi Pharma, Inc. Compositions of a carbohydrate vaccine for inducing immune responses and uses thereof in cancer treatment
CN112028951A (zh) * 2014-05-30 2020-12-04 索隆-基特林癌症研究协会 微小皂苷类似物、合成及其用途
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
CA3003483C (en) * 2015-11-06 2022-09-13 Adjuvance Technologies, Inc. Triterpene saponin analogues
AU2017239637A1 (en) 2016-03-29 2018-11-15 Obi Pharma, Inc. Antibodies, pharmaceutical compositions and methods
US10980894B2 (en) 2016-03-29 2021-04-20 Obi Pharma, Inc. Antibodies, pharmaceutical compositions and methods
CN109379889A (zh) 2016-04-22 2019-02-22 台湾浩鼎生技股份有限公司 通过经由globo系列抗原的免疫激活或免疫调节的癌症免疫疗法
KR20230117482A (ko) 2016-07-27 2023-08-08 오비아이 파머 인코퍼레이티드 면역원성/치료 글리칸 조성물 및 그의 용도
WO2018023121A1 (en) 2016-07-29 2018-02-01 Obi Pharma, Inc. Human antibodies, pharmaceutical compositions and methods
TWI822055B (zh) 2016-11-21 2023-11-11 台灣浩鼎生技股份有限公司 共軛生物分子、醫藥組成物及方法
US11129906B1 (en) 2016-12-07 2021-09-28 David Gordon Bermudes Chimeric protein toxins for expression by therapeutic bacteria
EP3609505A4 (en) * 2017-04-13 2021-04-28 Adjuvance Technologies, Inc. TRITERPEN-SAPONIN SYNTHESIS, INTERMEDIATES AND COMBINATIONS OF ADJUVANCES
EP3618836A4 (en) 2017-04-25 2021-01-13 Adjuvance Technologies, Inc. TRITERPENSAPONINALOGA
CN110730666A (zh) * 2017-04-25 2020-01-24 佐剂技术公司 三萜皂苷类似物
WO2019079160A1 (en) 2017-10-16 2019-04-25 Adjuvance Technologies, Inc. TRITERPENIC SAPONIN ANALOGS
CN111566117A (zh) 2017-12-29 2020-08-21 糖模拟物有限公司 E-选择蛋白和半乳凝素-3的异双功能抑制剂
US12497429B2 (en) * 2018-03-20 2025-12-16 The Uab Research Foundation Saponin-based vaccine adjuvants
WO2020006176A1 (en) 2018-06-27 2020-01-02 Obi Pharma, Inc. Glycosynthase variants for glycoprotein engineering and methods of use
CA3111386A1 (en) 2018-09-06 2020-03-12 Yeda Research And Development Co. Ltd. Cellulose-synthase-like enzymes and uses thereof
WO2020055503A1 (en) 2018-09-14 2020-03-19 Massachusetts Institute Of Technology Nanoparticle vaccine adjuvant and methods of use thereof
CN118373810A (zh) 2018-12-27 2024-07-23 糖模拟物有限公司 抑制c-糖苷的半乳凝素-3
US11845771B2 (en) 2018-12-27 2023-12-19 Glycomimetics, Inc. Heterobifunctional inhibitors of E-selectin and galectin-3
CA3157372A1 (en) * 2019-11-05 2021-05-14 Adjuvance Technologies, Inc. Varicella zoster
US20230128815A1 (en) * 2020-03-23 2023-04-27 Adjuvance Technologies, Inc. Adjuvant compounds, salt forms, and formulations
EP4171642A1 (en) * 2020-06-24 2023-05-03 Sapreme Technologies B.V. Combination of an antibody-drug conjugate and an antibody-saponin conjugate
US20250282811A1 (en) * 2021-10-02 2025-09-11 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
WO2023114570A1 (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
DE69637435T2 (de) * 1996-12-02 2009-02-19 Antigenics Inc. Saponin-zusammensetzungen und deren verwendung
US6231859B1 (en) 1996-12-02 2001-05-15 Aquila Biopharmaceuticals, Inc. Saponin adjuvant compositions
US6080725A (en) 1997-05-20 2000-06-27 Galenica Pharmaceuticals, Inc. Immunostimulating and vaccine compositions employing saponin analog adjuvants and uses thereof
BR9809149A (pt) 1997-05-20 2000-08-01 Galenica Pharmaceuticals Inc Análogos de triterpeno saponina dotados de adjuvante e atividade imonoestimulatória
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
US20040242502A1 (en) * 2003-04-08 2004-12-02 Galenica Pharmaceuticals, Inc. Semi-synthetic saponin analogs with carrier and immune stimulatory activities for DNA and RNA vaccines
AU2006243737A1 (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
JP5706815B2 (ja) 2008-04-08 2015-04-22 スローン − ケタリング・インスティテュート・フォー・キャンサー・リサーチ トリテルペンであるサポニン、その合成法および使用
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
CN112028951A (zh) * 2014-05-30 2020-12-04 索隆-基特林癌症研究协会 微小皂苷类似物、合成及其用途

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KIM, Y-J. et al, "Synthetic Studies of Complex Immunostimulants from Quillaja saponaria: Synthesis of the Potent Clinical Immunoadjuvant QS-21Aapi", Journal of the Americal Chemical Society, Vol. 128, 2006, pp 11906-11915 *

Also Published As

Publication number Publication date
US8283456B2 (en) 2012-10-09
JP2011516566A (ja) 2011-05-26
CN102112484A (zh) 2011-06-29
IL208535A (en) 2015-06-30
JP2015134793A (ja) 2015-07-27
JP6770596B2 (ja) 2020-10-14
WO2009126737A2 (en) 2009-10-15
IL239051A0 (en) 2015-07-30
IL237505A0 (en) 2015-04-30
KR102453184B1 (ko) 2022-10-07
EP3357931A1 (en) 2018-08-08
ES2827804T3 (es) 2021-05-24
US20250188109A1 (en) 2025-06-12
US9718850B2 (en) 2017-08-01
US12227535B2 (en) 2025-02-18
IL237505A (en) 2017-06-29
CA2993582C (en) 2020-12-15
KR20160103156A (ko) 2016-08-31
IL281261B (en) 2022-11-01
KR20200024964A (ko) 2020-03-09
CN102112484B (zh) 2015-03-04
US20230131867A1 (en) 2023-04-27
CA3096084A1 (en) 2009-10-15
HK1211591A1 (en) 2016-05-27
EP2280987B1 (en) 2018-05-23
JP6786410B2 (ja) 2020-11-18
KR101825315B1 (ko) 2018-02-02
CA2720771C (en) 2018-03-20
IL208535A0 (en) 2010-12-30
KR101651695B1 (ko) 2016-08-26
IL239051B (en) 2021-03-25
CN104710487A (zh) 2015-06-17
US8889842B2 (en) 2014-11-18
IL281261B2 (en) 2023-03-01
AU2009233757A1 (en) 2009-10-15
JP2020169206A (ja) 2020-10-15
US20130011421A1 (en) 2013-01-10
JP2019073530A (ja) 2019-05-16
KR20180014211A (ko) 2018-02-07
KR20190016595A (ko) 2019-02-18
KR102085687B1 (ko) 2020-03-06
IL281261A (en) 2021-04-29
US20170283450A1 (en) 2017-10-05
JP5706815B2 (ja) 2015-04-22
US11447515B2 (en) 2022-09-20
EP3357931B1 (en) 2020-07-22
CA2720771A1 (en) 2009-10-15
JP2017114876A (ja) 2017-06-29
KR102256410B1 (ko) 2021-05-26
KR20210062717A (ko) 2021-05-31
CA2993582A1 (en) 2009-10-15
KR20110003523A (ko) 2011-01-12
US20110300177A1 (en) 2011-12-08
US20150086585A1 (en) 2015-03-26
WO2009126737A3 (en) 2010-01-14
KR101947332B1 (ko) 2019-02-12
CA3096084C (en) 2022-12-20
EP2280987A2 (en) 2011-02-09
EP3868771A1 (en) 2021-08-25

Similar Documents

Publication Publication Date Title
AU2009233757B2 (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
HK1153746B (en) Triterpene saponins, methods of synthesis, and uses thereof
HK1153746A (en) Triterpene saponins, methods of synthesis, and uses thereof

Legal Events

Date Code Title Description
FGA Letters patent sealed or granted (standard patent)