HK1211591A1 - Triterpene saponins, methods of synthesis, and uses thereof - Google Patents

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

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Publication number
HK1211591A1
HK1211591A1 HK15112457.4A HK15112457A HK1211591A1 HK 1211591 A1 HK1211591 A1 HK 1211591A1 HK 15112457 A HK15112457 A HK 15112457A HK 1211591 A1 HK1211591 A1 HK 1211591A1
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Hong Kong
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group
nitrogen
oxygen
sulfur
independently selected
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HK15112457.4A
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English (en)
Chinese (zh)
Inventor
戴維‧金
戴维‧金
米歇爾‧亞當斯
米歇尔‧亚当斯
鄧凱
邓凯
尼古拉斯‧佩爾
尼古拉斯‧佩尔
安妮‧汪
菲利普‧利文斯頓
菲利普‧利文斯顿
戈文德‧拉古帕蒂
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索隆-基特林癌症研究协会
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Publication of HK1211591A1 publication Critical patent/HK1211591A1/xx

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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
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    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
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    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • AHUMAN NECESSITIES
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    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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)
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  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • 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)
HK15112457.4A 2008-04-08 2015-12-17 Triterpene saponins, methods of synthesis, and uses thereof HK1211591A1 (en)

Applications Claiming Priority (2)

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

Publications (1)

Publication Number Publication Date
HK1211591A1 true HK1211591A1 (en) 2016-05-27

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HK15112457.4A HK1211591A1 (en) 2008-04-08 2015-12-17 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

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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
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
AU2009233757B2 (en) 2015-05-07
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

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