KR102453184B1 - 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도 - Google Patents

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

Info

Publication number
KR102453184B1
KR102453184B1 KR1020217015136A KR20217015136A KR102453184B1 KR 102453184 B1 KR102453184 B1 KR 102453184B1 KR 1020217015136 A KR1020217015136 A KR 1020217015136A KR 20217015136 A KR20217015136 A KR 20217015136A KR 102453184 B1 KR102453184 B1 KR 102453184B1
Authority
KR
South Korea
Prior art keywords
group
oxygen
nitrogen
adjuvant
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
KR1020217015136A
Other languages
English (en)
Korean (ko)
Other versions
KR20210062717A (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 KR20210062717A publication Critical patent/KR20210062717A/ko
Application granted granted Critical
Publication of KR102453184B1 publication Critical patent/KR102453184B1/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
    • 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
    • A61K31/56Compounds 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
    • A61K31/7028Compounds 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

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)
KR1020217015136A 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도 Active KR102453184B1 (ko)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US4319708P 2008-04-08 2008-04-08
US61/043,197 2008-04-08
KR1020207006108A KR102256410B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도
PCT/US2009/039954 WO2009126737A2 (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
KR1020207006108A Division KR102256410B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도

Publications (2)

Publication Number Publication Date
KR20210062717A KR20210062717A (ko) 2021-05-31
KR102453184B1 true KR102453184B1 (ko) 2022-10-07

Family

ID=40875147

Family Applications (6)

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
KR1020107024935A Active KR101651695B1 (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
KR1020197003429A Active KR102085687B1 (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

Family Applications After (5)

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
KR1020187002556A Active KR101947332B1 (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
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

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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Yong-Jae Kim et.al., Synthetic Studies of complex Immunostimulants from Quillajasaponaria~, J.AM.CHEM.SOC., Vol.128, pp.11906-11915(2006.) 1부.*

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
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
CA2993582C (en) 2020-12-15
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
US20240327443A1 (en) Triterpene saponin analogues
JP2022191284A (ja) トリテルペンサポニン類似物
AU2015203675B2 (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
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: 20210520

Application number text: 1020207006108

Filing date: 20200302

PG1501 Laying open of application
PA0201 Request for examination

Patent event code: PA02012R01D

Patent event date: 20210618

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: 20210929

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: 20220830

GRNT Written decision to grant
PR0701 Registration of establishment

Comment text: Registration of Establishment

Patent event date: 20221005

Patent event code: PR07011E01D

PR1002 Payment of registration fee

Payment date: 20221005

End annual number: 3

Start annual number: 1

PG1601 Publication of registration