KR101651695B1 - 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도 - Google Patents

트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도 Download PDF

Info

Publication number
KR101651695B1
KR101651695B1 KR1020107024935A KR20107024935A KR101651695B1 KR 101651695 B1 KR101651695 B1 KR 101651695B1 KR 1020107024935 A KR1020107024935 A KR 1020107024935A KR 20107024935 A KR20107024935 A KR 20107024935A KR 101651695 B1 KR101651695 B1 KR 101651695B1
Authority
KR
South Korea
Prior art keywords
group
mmol
certain embodiments
compound
aliphatic
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
KR1020107024935A
Other languages
English (en)
Korean (ko)
Other versions
KR20110003523A (ko
Inventor
데이비드 진
미셀 아담스
카이 뎅
니콜라스 펄
애니 원
필립 리빙스톤
고빈드 라구파시
Original Assignee
슬로안-케테링인스티튜트퍼캔서리서치
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 슬로안-케테링인스티튜트퍼캔서리서치 filed Critical 슬로안-케테링인스티튜트퍼캔서리서치
Publication of KR20110003523A publication Critical patent/KR20110003523A/ko
Application granted granted Critical
Publication of KR101651695B1 publication Critical patent/KR101651695B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • 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
    • 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
    • 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

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)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (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)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • Pulmonology (AREA)
  • AIDS & HIV (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)
  • Medicines Containing Plant Substances (AREA)
  • Pyrane Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
KR1020107024935A 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도 Active KR101651695B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US4319708P 2008-04-08 2008-04-08
US61/043,197 2008-04-08

Related Child Applications (1)

Application Number Title Priority Date Filing Date
KR1020167022654A Division KR101825315B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도

Publications (2)

Publication Number Publication Date
KR20110003523A KR20110003523A (ko) 2011-01-12
KR101651695B1 true KR101651695B1 (ko) 2016-08-26

Family

ID=40875147

Family Applications (6)

Application Number Title Priority Date Filing Date
KR1020107024935A Active KR101651695B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도
KR1020217015136A Active KR102453184B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도
KR1020187002556A Active KR101947332B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도
KR1020207006108A Active KR102256410B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도
KR1020167022654A Active KR101825315B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도
KR1020197003429A Active KR102085687B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도

Family Applications After (5)

Application Number Title Priority Date Filing Date
KR1020217015136A Active KR102453184B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도
KR1020187002556A Active KR101947332B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도
KR1020207006108A Active KR102256410B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도
KR1020167022654A Active KR101825315B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도
KR1020197003429A Active KR102085687B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도

Country Status (11)

Country Link
US (6) US8283456B2 (enExample)
EP (3) EP2280987B1 (enExample)
JP (5) JP5706815B2 (enExample)
KR (6) KR101651695B1 (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 (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2280987B1 (en) 2008-04-08 2018-05-23 Sloan-Kettering Institute for Cancer Research Triterpene saponins, methods of synthesis, and uses thereof
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
ES2843509T3 (es) 2013-01-04 2021-07-19 Obi Pharma Inc Vacunas con mayor densidad de antígeno carbohidratado y nuevo adyuvante de saponina
US10806119B2 (en) 2013-06-05 2020-10-20 Yeda Research And Development Co. Ltd. Plant with altered content of steroidal alkaloids
RU2666141C2 (ru) 2013-09-17 2018-09-06 Оби Фарма, Инк. Композиции углеводной вакцины для индукции иммунного ответа и их применение при лечении рака
SG11201610004PA (en) * 2014-05-30 2016-12-29 Sloan Kettering Inst Cancer 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
JP2018532990A (ja) 2015-09-04 2018-11-08 オービーアイ ファーマ,インコーポレイテッド グリカンアレイおよび使用の方法
IL286493B (en) * 2015-11-06 2022-07-01 Memorial Sloan Kettering Cancer Center Triterpene saponin analogues, methods of producing same, compositions comprising same and uses thereof
US11041017B2 (en) 2016-03-29 2021-06-22 Obi Pharma, Inc. Antibodies, pharmaceutical compositions and methods
US10980894B2 (en) 2016-03-29 2021-04-20 Obi Pharma, Inc. Antibodies, pharmaceutical compositions and methods
KR20250048399A (ko) 2016-04-22 2025-04-08 오비아이 파머 인코퍼레이티드 글로보 계열 항원을 통한 면역 활성화 또는 면역 조정에 의한 암 면역요법
WO2018022933A1 (en) 2016-07-27 2018-02-01 Obi Pharma, Inc. Immunogenic/therapeutic glycan compositions and uses thereof
EP3491026A4 (en) 2016-07-29 2020-07-29 OBI Pharma, Inc. HUMAN ANTIBODIES, PHARMACEUTICAL COMPOSITIONS AND PROCESSES
JP2019535731A (ja) 2016-11-21 2019-12-12 オービーアイ ファーマ,インコーポレイテッド コンジュゲートさせた生物学的分子、医薬組成物及び方法
US11129906B1 (en) 2016-12-07 2021-09-28 David Gordon Bermudes Chimeric protein toxins for expression by therapeutic bacteria
WO2018191598A1 (en) * 2017-04-13 2018-10-18 Adjuvance Technologies, Inc. Triterpene saponin synthesis, intermediates and adjuvant combinations
AU2018258070A1 (en) 2017-04-25 2019-10-24 Adjuvance Technologies, Inc. Triterpene saponin analogues
WO2018200656A1 (en) * 2017-04-25 2018-11-01 Adjuvance Technologies, Inc. Triterpene saponin analogues
WO2019079160A1 (en) 2017-10-16 2019-04-25 Adjuvance Technologies, Inc. TRITERPENIC SAPONIN ANALOGS
EP3732186A1 (en) 2017-12-29 2020-11-04 GlycoMimetics, Inc. Heterobifunctional inhibitors of e-selectin and galectin-3
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
US12041907B2 (en) 2018-09-06 2024-07-23 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
CA3122321A1 (en) 2018-12-27 2020-07-02 Glycomimetics, Inc. Galectin-3 inhibiting c-glycosides
US11845771B2 (en) 2018-12-27 2023-12-19 Glycomimetics, Inc. Heterobifunctional inhibitors of E-selectin and galectin-3
KR20220097396A (ko) * 2019-11-05 2022-07-07 아쥬반스 테크놀로지스 인코포레이티드 바리셀라 조스터
US20230128815A1 (en) * 2020-03-23 2023-04-27 Adjuvance Technologies, Inc. Adjuvant compounds, salt forms, and formulations
CN116249553A (zh) * 2020-06-24 2023-06-09 萨普雷米科技有限公司 抗体-药物缀合物和抗体-皂苷缀合物的组合
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
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
US20250114448A1 (en) 2022-01-19 2025-04-10 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
CN121852499A (zh) * 2026-03-17 2026-04-14 武汉糖智药业有限公司 Qs-7生物合成乙酰化的方法

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
CA2273922C (en) * 1996-12-02 2008-08-05 Antigenics Inc. Novel saponin compositions and uses thereof
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
WO1998052573A1 (en) 1997-05-20 1998-11-26 Galenica Pharmaceuticals, Inc. Triterpene saponin analogs having adjuvant and immunostimulatory activity
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
EP1876882A4 (en) * 2005-05-04 2009-01-14 Ca Nat Research Council 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
EP2280987B1 (en) * 2008-04-08 2018-05-23 Sloan-Kettering Institute for Cancer Research Triterpene saponins, methods of synthesis, and uses thereof
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
SG11201610004PA (en) * 2014-05-30 2016-12-29 Sloan Kettering Inst Cancer Minimal saponin analogues, synthesis and use thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
J. Am. Chem. Soc. Vol. 128, Pages 11906-11915(공개일: 2006)..*
Vaccine, Vol. 13, No. 15, Pages 1403-1410(공개일: 1995. 1. 1.)

Also Published As

Publication number Publication date
JP5706815B2 (ja) 2015-04-22
JP2011516566A (ja) 2011-05-26
KR20200024964A (ko) 2020-03-09
CA2720771C (en) 2018-03-20
IL281261B (en) 2022-11-01
IL281261A (en) 2021-04-29
KR20160103156A (ko) 2016-08-31
WO2009126737A2 (en) 2009-10-15
JP2017114876A (ja) 2017-06-29
WO2009126737A3 (en) 2010-01-14
EP2280987B1 (en) 2018-05-23
JP6786410B2 (ja) 2020-11-18
CA2720771A1 (en) 2009-10-15
KR20210062717A (ko) 2021-05-31
US8283456B2 (en) 2012-10-09
KR20190016595A (ko) 2019-02-18
HK1211591A1 (en) 2016-05-27
US11447515B2 (en) 2022-09-20
EP3868771A1 (en) 2021-08-25
CA3096084C (en) 2022-12-20
JP2015134793A (ja) 2015-07-27
US20150086585A1 (en) 2015-03-26
CA2993582C (en) 2020-12-15
KR20180014211A (ko) 2018-02-07
KR102453184B1 (ko) 2022-10-07
KR20110003523A (ko) 2011-01-12
US20230131867A1 (en) 2023-04-27
US9718850B2 (en) 2017-08-01
EP3357931B1 (en) 2020-07-22
CN104710487A (zh) 2015-06-17
US12227535B2 (en) 2025-02-18
EP3357931A1 (en) 2018-08-08
IL281261B2 (en) 2023-03-01
ES2827804T3 (es) 2021-05-24
AU2009233757A1 (en) 2009-10-15
JP2020169206A (ja) 2020-10-15
JP2019073530A (ja) 2019-05-16
CN102112484B (zh) 2015-03-04
KR102085687B1 (ko) 2020-03-06
US8889842B2 (en) 2014-11-18
IL239051A0 (en) 2015-07-30
CA2993582A1 (en) 2009-10-15
KR101947332B1 (ko) 2019-02-12
KR102256410B1 (ko) 2021-05-26
US20250188109A1 (en) 2025-06-12
IL239051B (en) 2021-03-25
US20110300177A1 (en) 2011-12-08
KR101825315B1 (ko) 2018-02-02
US20170283450A1 (en) 2017-10-05
JP6770596B2 (ja) 2020-10-14
EP2280987A2 (en) 2011-02-09
IL237505A (en) 2017-06-29
IL208535A (en) 2015-06-30
IL208535A0 (en) 2010-12-30
US20130011421A1 (en) 2013-01-10
IL237505A0 (en) 2015-04-30
CN102112484A (zh) 2011-06-29
AU2009233757B2 (en) 2015-05-07
CA3096084A1 (en) 2009-10-15

Similar Documents

Publication Publication Date Title
KR101825315B1 (ko) 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도
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
PA0105 International application

Patent event date: 20101105

Patent event code: PA01051R01D

Comment text: International Patent Application

PG1501 Laying open of application
A201 Request for examination
PA0201 Request for examination

Patent event code: PA02012R01D

Patent event date: 20140408

Comment text: Request for Examination of Application

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

Comment text: Notification of reason for refusal

Patent event date: 20151218

Patent event code: PE09021S01D

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

Patent event code: PE07011S01D

Comment text: Decision to Grant Registration

Patent event date: 20160524

A107 Divisional application of patent
PA0104 Divisional application for international application

Comment text: Divisional Application for International Patent

Patent event code: PA01041R01D

Patent event date: 20160819

GRNT Written decision to grant
PR0701 Registration of establishment

Comment text: Registration of Establishment

Patent event date: 20160822

Patent event code: PR07011E01D

PR1002 Payment of registration fee

Payment date: 20160822

End annual number: 3

Start annual number: 1

PG1601 Publication of registration
FPAY Annual fee payment

Payment date: 20190729

Year of fee payment: 4

PR1001 Payment of annual fee

Payment date: 20190729

Start annual number: 4

End annual number: 4

PR1001 Payment of annual fee

Payment date: 20210728

Start annual number: 6

End annual number: 6

PR1001 Payment of annual fee

Payment date: 20220718

Start annual number: 7

End annual number: 7

PR1001 Payment of annual fee

Payment date: 20230705

Start annual number: 8

End annual number: 8

PR1001 Payment of annual fee

Payment date: 20240718

Start annual number: 9

End annual number: 9