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

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

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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
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group
bno
nitrogen
oxygen
sulfur
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AU2009233757A1 (en
Inventor
Michelle Adams
Kai DENG
David Gin
Philip Livingston
Nicholas Perl
Govind Ragupathi
Annie Won
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Memorial Sloan Kettering Cancer Center
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Memorial Sloan Kettering Cancer Center
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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
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20Carbocyclic rings
    • C07H15/24Condensed ring systems having three or more rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/56Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7024Esters of saccharides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704Compounds 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/74Synthetic polymeric materials
    • A61K31/80Polymers containing hetero atoms not provided for in groups A61K31/755 - A61K31/795
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00Medicinal preparations containing antigens or antibodies
    • A61K39/385Haptens or antigens, bound to carriers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • A61P31/16Antivirals for RNA viruses for influenza or rhinoviruses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • A61P31/18Antivirals for RNA viruses for HIV
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/20Antivirals for DNA viruses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/20Antivirals for DNA viruses
    • A61P31/22Antivirals for DNA viruses for herpes viruses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00Antiparasitic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00Antiparasitic agents
    • A61P33/02Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/02Antineoplastic agents specific for leukemia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/04Immunostimulants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56Ring systems containing three or more rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/08Compounds 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20Carbocyclic rings
    • C07H15/24Condensed ring systems having three or more rings
    • C07H15/256Polyterpene radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00Compounds 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
    • C07H5/04Compounds 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
    • C07H5/06Aminosugars
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30Against 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)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (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)
  • AIDS & HIV (AREA)
  • Hematology (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)
  • 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)

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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

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US (6) US8283456B2 (cg-RX-API-DMAC7.html)
EP (3) EP3868771A1 (cg-RX-API-DMAC7.html)
JP (5) JP5706815B2 (cg-RX-API-DMAC7.html)
KR (6) KR101825315B1 (cg-RX-API-DMAC7.html)
CN (2) CN104710487A (cg-RX-API-DMAC7.html)
AU (1) AU2009233757B2 (cg-RX-API-DMAC7.html)
CA (3) CA3096084C (cg-RX-API-DMAC7.html)
ES (1) ES2827804T3 (cg-RX-API-DMAC7.html)
HK (1) HK1211591A1 (cg-RX-API-DMAC7.html)
IL (4) IL208535A (cg-RX-API-DMAC7.html)
WO (1) WO2009126737A2 (cg-RX-API-DMAC7.html)

Families Citing this family (35)

* 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
CN111499679B (zh) 2013-01-04 2021-07-06 台湾浩鼎生技股份有限公司 具有较高碳水化合物抗原密度的疫苗及新颖皂素佐剂
US10806119B2 (en) 2013-06-05 2020-10-20 Yeda Research And Development Co. Ltd. Plant with altered content of steroidal alkaloids
HK1222569A1 (zh) 2013-09-17 2017-07-07 Obi Pharma, Inc. 用於诱导免疫反应的糖疫苗组合物及其治疗癌症的用途
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
US10676723B2 (en) 2015-05-11 2020-06-09 David Gordon Bermudes Chimeric protein toxins for expression by therapeutic bacteria
AR105910A1 (es) 2015-09-04 2017-11-22 Obi Pharma Inc Matrices de glicano y método de uso
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
US10980894B2 (en) 2016-03-29 2021-04-20 Obi Pharma, Inc. Antibodies, pharmaceutical compositions and methods
BR112018070097A2 (pt) 2016-03-29 2019-02-12 Obi Pharma, Inc. anticorpo, hibridoma, composição farmacêutica, método para tratar câncer em um indivíduo, método para inibir a proliferação de células cancerígenas, método para diagnosticar o câncer em um indivíduo, método para tratar um paciente humano, método para fazer imagens de um indivíduo, conjugado de fármaco-anticorpo (adc), método para tratar câncer, anticorpo biespecífico e método para preparar uma população de anticorpos homogêneos
TWI697333B (zh) 2016-04-22 2020-07-01 台灣浩鼎生技股份有限公司 經由Globo系列抗原之免疫活化或免疫調節之癌症免疫療法
JP2019527690A (ja) 2016-07-27 2019-10-03 オービーアイ ファーマ,インコーポレイテッド 免疫原性/治療用グリカン組成物およびその使用
JP7121724B2 (ja) 2016-07-29 2022-08-18 オービーアイ ファーマ,インコーポレイテッド ヒト抗体、医薬組成物及び方法
WO2018094414A1 (en) 2016-11-21 2018-05-24 Obi Pharma, Inc. Conjugated biological molecules, pharmaceutical compositions and methods
US11129906B1 (en) 2016-12-07 2021-09-28 David Gordon Bermudes Chimeric protein toxins for expression by therapeutic bacteria
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
CA3085356A1 (en) 2017-12-29 2019-07-04 Glycomimetics, Inc. Heterobifunctional inhibitors of e-selectin and galectin-3
WO2019183159A1 (en) * 2018-03-20 2019-09-26 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
EP3849521A1 (en) 2018-09-14 2021-07-21 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
WO2020139962A1 (en) 2018-12-27 2020-07-02 Glycomimetics, Inc. Heterobifunctional inhibitors of e-selectin and galectin-3
AU2020379738A1 (en) * 2019-11-05 2022-04-14 Adjuvance Technologies, Inc. Varicella zoster
WO2021195024A1 (en) * 2020-03-23 2021-09-30 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
EP4466278A1 (en) 2022-01-19 2024-11-27 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
DK0952771T3 (da) * 1996-12-02 2008-05-19 Antigenics Inc Hidtil ukendte saponinpræparater og anvendelser deraf
EP0996451B1 (en) 1997-05-20 2005-01-05 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
EP0988053A1 (en) * 1997-06-11 2000-03-29 Aquila Biopharmaceuticals, Inc. Purified saponins as oral adjuvants
US6262029B1 (en) 1998-08-14 2001-07-17 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
WO2006116876A1 (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
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

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 *

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IL239051A0 (en) 2015-07-30
JP2011516566A (ja) 2011-05-26
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IL208535A (en) 2015-06-30
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US20130011421A1 (en) 2013-01-10
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US20110300177A1 (en) 2011-12-08
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IL237505A0 (en) 2015-04-30
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