KR102256410B1 - 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도 - Google Patents

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

Info

Publication number
KR102256410B1
KR102256410B1 KR1020207006108A KR20207006108A KR102256410B1 KR 102256410 B1 KR102256410 B1 KR 102256410B1 KR 1020207006108 A KR1020207006108 A KR 1020207006108A KR 20207006108 A KR20207006108 A KR 20207006108A KR 102256410 B1 KR102256410 B1 KR 102256410B1
Authority
KR
South Korea
Prior art keywords
group
mmol
certain embodiments
compound
formula
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
KR1020207006108A
Other languages
English (en)
Korean (ko)
Other versions
KR20200024964A (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
Priority to KR1020217015136A priority Critical patent/KR102453184B1/ko
Publication of KR20200024964A publication Critical patent/KR20200024964A/ko
Application granted granted Critical
Publication of KR102256410B1 publication Critical patent/KR102256410B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • 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
    • 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)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (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)
  • 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)
  • Medicines Containing Plant Substances (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyrane Compounds (AREA)
KR1020207006108A 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도 Active KR102256410B1 (ko)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020217015136A KR102453184B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도

Applications Claiming Priority (4)

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
KR1020197003429A KR102085687B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
KR1020197003429A Division KR102085687B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도

Related Child Applications (1)

Application Number Title Priority Date Filing Date
KR1020217015136A Division KR102453184B1 (ko) 2008-04-08 2009-04-08 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도

Publications (2)

Publication Number Publication Date
KR20200024964A KR20200024964A (ko) 2020-03-09
KR102256410B1 true KR102256410B1 (ko) 2021-05-26

Family

ID=40875147

Family Applications (6)

Application Number Title Priority Date Filing Date
KR1020207006108A Active KR102256410B1 (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
KR1020197003429A Active KR102085687B1 (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
KR1020167022654A Active KR101825315B1 (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

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
KR1020197003429A Active KR102085687B1 (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
KR1020167022654A Active KR101825315B1 (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

Country Status (11)

Country Link
US (6) US8283456B2 (enExample)
EP (3) EP3868771A1 (enExample)
JP (5) JP5706815B2 (enExample)
KR (6) KR102256410B1 (enExample)
CN (2) CN104710487A (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 (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102256410B1 (ko) 2008-04-08 2021-05-26 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
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
BR112015032713B1 (pt) 2013-09-17 2023-03-21 Obi Pharma, Inc Composto, composição farmacêutica, uso de uma quantidade terapeuticamente efetiva da composição farmacêutica, e uso do composto
KR102424785B1 (ko) 2014-05-30 2022-07-25 메모리얼 슬로안 케터링 캔서 센터 최소 사포닌 유사체, 이의 합성법 및 용도
US10676723B2 (en) 2015-05-11 2020-06-09 David Gordon Bermudes Chimeric protein toxins for expression by therapeutic bacteria
US10935544B2 (en) 2015-09-04 2021-03-02 Obi Pharma, Inc. Glycan arrays and method of use
CN108778289B (zh) * 2015-11-06 2020-11-17 佐剂技术公司 三萜皂苷类似物
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
KR20230110820A (ko) 2016-04-22 2023-07-25 오비아이 파머 인코퍼레이티드 글로보 계열 항원을 통한 면역 활성화 또는 면역 조정에의한 암 면역요법
CN110072545A (zh) 2016-07-27 2019-07-30 台湾浩鼎生技股份有限公司 免疫原性/治疗性聚糖组合物及其用途
US11643456B2 (en) 2016-07-29 2023-05-09 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
WO2018191598A1 (en) * 2017-04-13 2018-10-18 Adjuvance Technologies, Inc. Triterpene saponin synthesis, intermediates and adjuvant combinations
CA3061205A1 (en) 2017-04-25 2018-11-01 Memorial Sloan Kettering Cancer Center Triterpene saponin analogues
US20200164065A1 (en) * 2017-04-25 2020-05-28 Adjuvance Technologies, Inc. Triterpene saponin analogues
SG11202001826YA (en) * 2017-10-16 2020-03-30 Adjuvance Technologies Inc Triterpene saponin analogues
KR20200104889A (ko) 2017-12-29 2020-09-04 글리코미메틱스, 인크. E-셀렉틴 및 갈렉틴-3의 이종이기능성 억제제
US12497429B2 (en) * 2018-03-20 2025-12-16 The Uab Research Foundation Saponin-based vaccine adjuvants
TW202504930A (zh) 2018-06-27 2025-02-01 台灣浩鼎生技股份有限公司 用於糖蛋白工程的糖苷合成酶變體及其使用方法
SG11202102106RA (en) 2018-09-06 2021-04-29 Yeda Res & Dev 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
US11845771B2 (en) 2018-12-27 2023-12-19 Glycomimetics, Inc. Heterobifunctional inhibitors of E-selectin and galectin-3
CA3122321A1 (en) 2018-12-27 2020-07-02 Glycomimetics, Inc. Galectin-3 inhibiting c-glycosides
IL292796A (en) * 2019-11-05 2022-07-01 Adjuvance Tech Inc Varicella zoster immunogenic compositions and uses thereof
WO2021195024A1 (en) * 2020-03-23 2021-09-30 Adjuvance Technologies, Inc. Adjuvant compounds, salt forms, and formulations
KR20230044195A (ko) * 2020-06-24 2023-04-03 사프렘 테크놀로지스 비.브이. 항체-약물 접합체와 항체-사포닌 접합체의 조합물
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
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
EP4466278A1 (en) 2022-01-19 2024-11-27 Asociación Centro de Investigación Cooperativa en Biociencias - CIC bioGUNE Saponin-based adjuvants and vaccines
EP4698224A1 (en) 2023-04-20 2026-02-25 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
DK0952771T3 (da) * 1996-12-02 2008-05-19 Antigenics Inc Hidtil ukendte saponinpræparater og anvendelser deraf
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
DE69828507T2 (de) 1997-05-20 2006-01-05 Galenica Pharmaceuticals, Inc. Triterpene-saponin analoga mit adjuvans und immunostimulierender wirkung
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
KR102256410B1 (ko) * 2008-04-08 2021-05-26 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
KR102424785B1 (ko) * 2014-05-30 2022-07-25 메모리얼 슬로안 케터링 캔서 센터 최소 사포닌 유사체, 이의 합성법 및 용도

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
US20150086585A1 (en) 2015-03-26
KR20110003523A (ko) 2011-01-12
KR20200024964A (ko) 2020-03-09
US11447515B2 (en) 2022-09-20
EP2280987A2 (en) 2011-02-09
KR102085687B1 (ko) 2020-03-06
IL208535A0 (en) 2010-12-30
IL237505A0 (en) 2015-04-30
KR101651695B1 (ko) 2016-08-26
AU2009233757A1 (en) 2009-10-15
CA2720771A1 (en) 2009-10-15
CA3096084C (en) 2022-12-20
JP2017114876A (ja) 2017-06-29
WO2009126737A2 (en) 2009-10-15
US8283456B2 (en) 2012-10-09
US20250188109A1 (en) 2025-06-12
KR102453184B1 (ko) 2022-10-07
US20110300177A1 (en) 2011-12-08
US8889842B2 (en) 2014-11-18
US20130011421A1 (en) 2013-01-10
ES2827804T3 (es) 2021-05-24
IL208535A (en) 2015-06-30
CN102112484A (zh) 2011-06-29
IL281261A (en) 2021-04-29
CN104710487A (zh) 2015-06-17
CA3096084A1 (en) 2009-10-15
IL281261B2 (en) 2023-03-01
KR20210062717A (ko) 2021-05-31
JP2019073530A (ja) 2019-05-16
IL239051B (en) 2021-03-25
KR20160103156A (ko) 2016-08-31
US20170283450A1 (en) 2017-10-05
CN102112484B (zh) 2015-03-04
CA2993582C (en) 2020-12-15
JP6770596B2 (ja) 2020-10-14
KR20180014211A (ko) 2018-02-07
JP2011516566A (ja) 2011-05-26
HK1211591A1 (en) 2016-05-27
AU2009233757B2 (en) 2015-05-07
IL281261B (en) 2022-11-01
EP3357931A1 (en) 2018-08-08
JP2015134793A (ja) 2015-07-27
EP3357931B1 (en) 2020-07-22
EP3868771A1 (en) 2021-08-25
US9718850B2 (en) 2017-08-01
CA2993582A1 (en) 2009-10-15
KR20190016595A (ko) 2019-02-18
JP2020169206A (ja) 2020-10-15
IL237505A (en) 2017-06-29
US20230131867A1 (en) 2023-04-27
CA2720771C (en) 2018-03-20
WO2009126737A3 (en) 2010-01-14
EP2280987B1 (en) 2018-05-23
KR101947332B1 (ko) 2019-02-12
JP6786410B2 (ja) 2020-11-18
US12227535B2 (en) 2025-02-18
KR101825315B1 (ko) 2018-02-02
IL239051A0 (en) 2015-07-30
JP5706815B2 (ja) 2015-04-22

Similar Documents

Publication Publication Date Title
US12227535B2 (en) Triterpene saponins, methods of synthesis and uses thereof
AU2017258850B2 (en) Triterpene saponins, methods of synthesis, and uses thereof
HK40061427A (en) Triterpene saponins, methods of synthesis, and uses thereof
HK1259568A1 (en) Methods of synthesis of triterpene prosapogenins and triterpene saponins
HK1259568B (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

St.27 status event code: A-0-1-A10-A18-div-PA0104

St.27 status event code: A-0-1-A10-A16-div-PA0104

PG1501 Laying open of application

St.27 status event code: A-1-1-Q10-Q12-nap-PG1501

A201 Request for examination
P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PA0201 Request for examination

St.27 status event code: A-1-2-D10-D11-exm-PA0201

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

St.27 status event code: A-1-2-D10-D21-exm-PE0902

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

E13-X000 Pre-grant limitation requested

St.27 status event code: A-2-3-E10-E13-lim-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

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

St.27 status event code: A-1-2-D10-D22-exm-PE0701

A107 Divisional application of patent
GRNT Written decision to grant
PA0104 Divisional application for international application

St.27 status event code: A-0-1-A10-A18-div-PA0104

St.27 status event code: A-0-1-A10-A16-div-PA0104

PR0701 Registration of establishment

St.27 status event code: A-2-4-F10-F11-exm-PR0701

PR1002 Payment of registration fee

St.27 status event code: A-2-2-U10-U12-oth-PR1002

Fee payment year number: 1

PG1601 Publication of registration

St.27 status event code: A-4-4-Q10-Q13-nap-PG1601

R17-X000 Change to representative recorded

St.27 status event code: A-5-5-R10-R17-oth-X000

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 4

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 5

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 6

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-OTH-PR1001 (AS PROVIDED BY THE NATIONAL OFFICE)

Year of fee payment: 6