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

Triterpene saponins, methods of synthesis, and uses thereof

Info

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
Authority
HK
Hong Kong
Prior art keywords
synthesis
methods
triterpene saponins
triterpene
saponins
Prior art date
Application number
HK15112457.4A
Other languages
English (en)
Chinese (zh)
Inventor
戴維‧金
米歇爾‧亞當斯
鄧凱
尼古拉斯‧佩爾
安妮‧汪
菲利普‧利文斯頓
戈文德‧拉古帕蒂
Original Assignee
Sloan Kettering Inst Cancer
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 Sloan Kettering Inst Cancer filed Critical Sloan Kettering Inst Cancer
Publication of HK1211591A1 publication Critical patent/HK1211591A1/xx

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7024—Esters of saccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704—Compounds 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/74—Synthetic polymeric materials
    • A61K31/80—Polymers containing hetero atoms not provided for in groups A61K31/755 - A61K31/795
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/385—Haptens or antigens, bound to carriers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • A61P31/22—Antivirals for DNA viruses for herpes viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/08—Compounds 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C07H15/256—Polyterpene radicals
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against 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)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Virology (AREA)
  • Biotechnology (AREA)
  • Epidemiology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (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)
  • Medicines Containing Plant Substances (AREA)
  • Pyrane Compounds (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 (1)

Application Number Priority Date Filing Date Title
US4319708P 2008-04-08 2008-04-08

Publications (1)

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

Family

ID=40875147

Family Applications (1)

Application Number Title Priority Date Filing Date
HK15112457.4A HK1211591A1 (en) 2008-04-08 2015-12-17 Triterpene saponins, methods of synthesis, and uses thereof

Country Status (11)

Country Link
US (5) US8283456B2 (xx)
EP (3) EP3868771A1 (xx)
JP (5) JP5706815B2 (xx)
KR (6) KR102256410B1 (xx)
CN (2) CN104710487A (xx)
AU (1) AU2009233757B2 (xx)
CA (3) CA2993582C (xx)
ES (1) ES2827804T3 (xx)
HK (1) HK1211591A1 (xx)
IL (4) IL208535A (xx)
WO (1) WO2009126737A2 (xx)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3868771A1 (en) 2008-04-08 2021-08-25 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
TWI572356B (zh) 2013-01-04 2017-03-01 台灣浩鼎生技股份有限公司 具有較高碳水化合物抗原密度之疫苗及新穎皂素佐劑
US10806119B2 (en) 2013-06-05 2020-10-20 Yeda Research And Development Co. Ltd. Plant with altered content of steroidal alkaloids
SG10202106403QA (en) * 2014-05-30 2021-07-29 Memorial Sloan Kettering Cancer Center Minimal saponin analogues, synthesis and use thereof
US10935544B2 (en) 2015-09-04 2021-03-02 Obi Pharma, Inc. Glycan arrays and method of use
EP3370730A4 (en) 2015-11-06 2019-07-31 Adjuvance Technologies, Inc. TRITERPENIC SAPONIN ANALOGS
WO2017172990A1 (en) 2016-03-29 2017-10-05 Obi Pharma, Inc. Antibodies, pharmaceutical compositions and methods
US10980894B2 (en) 2016-03-29 2021-04-20 Obi Pharma, Inc. Antibodies, pharmaceutical compositions and methods
MY200886A (en) 2016-04-22 2024-01-22 Obi Pharma Inc Cancer Immunotherapy by Immune Activation or Immune Modulation Via Globo Series Antigens
EP3490592A4 (en) 2016-07-27 2020-03-25 OBI Pharma, Inc. IMMUNOGENIC / THERAPEUTIC GLYCAN COMPOSITIONS AND USES THEREOF
WO2018023121A1 (en) 2016-07-29 2018-02-01 Obi Pharma, Inc. Human antibodies, pharmaceutical compositions and methods
AU2017361549B2 (en) 2016-11-21 2023-12-21 Obi Pharma, Inc. Conjugated biological molecules, pharmaceutical compositions and methods
US11129906B1 (en) 2016-12-07 2021-09-28 David Gordon Bermudes Chimeric protein toxins for expression by therapeutic bacteria
KR20190137808A (ko) * 2017-04-13 2019-12-11 아쥬반스 테크놀로지스 인코포레이티드 트리테르펜 사포닌, 중간체 및 보조제 배합물
US20200164065A1 (en) * 2017-04-25 2020-05-28 Adjuvance Technologies, Inc. Triterpene saponin analogues
US20210283248A1 (en) * 2017-04-25 2021-09-16 Adjuvance Technologies, Inc. Triterpene saponin analogues
KR20200098476A (ko) * 2017-10-16 2020-08-20 아쥬반스 테크놀로지스 인코포레이티드 트리테르펜 사포닌 유사체
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
WO2019183159A1 (en) * 2018-03-20 2019-09-26 The Uab Research Foundation Saponin-based vaccine adjuvants
WO2020006176A1 (en) 2018-06-27 2020-01-02 Obi Pharma, Inc. Glycosynthase variants for glycoprotein engineering and methods of use
EP3849521A1 (en) 2018-09-14 2021-07-21 Massachusetts Institute Of Technology Nanoparticle vaccine adjuvant and methods of use thereof
KR20210110645A (ko) 2018-12-27 2021-09-08 글리코미메틱스, 인크. 갈렉틴-3 억제 c-글리코사이드
US11845771B2 (en) 2018-12-27 2023-12-19 Glycomimetics, Inc. Heterobifunctional inhibitors of E-selectin and galectin-3
WO2021195024A1 (en) * 2020-03-23 2021-09-30 Adjuvance Technologies, Inc. Adjuvant compounds, salt forms, and formulations
WO2023052829A1 (en) * 2021-10-02 2023-04-06 Desert King Chile S.A A 3-o-monodesmosidic saponins extract, stable at physiological ph, method for preparing it from a quillaja plant extract cultured with a microbial consortium, uses and such microbial consortium
EP4190359A1 (en) 2021-12-03 2023-06-07 Asociación Centro de Investigación Cooperativa en Biociencias - CIC bioGUNE Saponin-based adjuvants and vaccines
US20230190920A1 (en) 2021-12-19 2023-06-22 Massachusetts Institute Of Technology Compositions and methods for long-lasting germinal center responses to a priming immunization
WO2023139145A1 (en) 2022-01-19 2023-07-27 Asociación Centro De Investigación Cooperativa En Biociencias-Cic Biogune Saponin-based adjuvants and vaccines

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
NZ500779A (en) 1997-05-20 2001-06-29 Galenica Pharmaceuticals Inc Triterpene saponin analogs having adjuvant and immunostimulatory activity
US6080725A (en) 1997-05-20 2000-06-27 Galenica Pharmaceuticals, Inc. Immunostimulating and vaccine compositions employing saponin analog adjuvants and uses thereof
EP0988053A1 (en) * 1997-06-11 2000-03-29 Aquila Biopharmaceuticals, Inc. Purified saponins as oral adjuvants
US6262029B1 (en) 1998-08-14 2001-07-17 Galenica Pharmaceuticals, Inc. Chemically modified saponins and the use thereof as adjuvants
US7457415B2 (en) 1998-08-20 2008-11-25 Akikaze Technologies, Llc Secure information distribution system utilizing information segment scrambling
US6716428B1 (en) 1999-10-06 2004-04-06 The Ohio State University Research Foundation Antigenic modification of polypeptides
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 PROCESS FOR PRODUCING SAPONARY 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
EP3868771A1 (en) * 2008-04-08 2021-08-25 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
SG10202106403QA (en) * 2014-05-30 2021-07-29 Memorial Sloan Kettering Cancer Center Minimal saponin analogues, synthesis and use thereof

Also Published As

Publication number Publication date
US20230131867A1 (en) 2023-04-27
IL237505A (en) 2017-06-29
CN102112484A (zh) 2011-06-29
IL239051A0 (en) 2015-07-30
AU2009233757B2 (en) 2015-05-07
IL208535A (en) 2015-06-30
US20150086585A1 (en) 2015-03-26
US20110300177A1 (en) 2011-12-08
EP2280987A2 (en) 2011-02-09
CN102112484B (zh) 2015-03-04
CN104710487A (zh) 2015-06-17
AU2009233757A1 (en) 2009-10-15
US8283456B2 (en) 2012-10-09
KR20160103156A (ko) 2016-08-31
CA2720771C (en) 2018-03-20
IL208535A0 (en) 2010-12-30
JP5706815B2 (ja) 2015-04-22
US9718850B2 (en) 2017-08-01
US20130011421A1 (en) 2013-01-10
CA2993582C (en) 2020-12-15
KR102085687B1 (ko) 2020-03-06
KR102256410B1 (ko) 2021-05-26
US8889842B2 (en) 2014-11-18
EP3357931B1 (en) 2020-07-22
KR101825315B1 (ko) 2018-02-02
JP2020169206A (ja) 2020-10-15
EP3868771A1 (en) 2021-08-25
IL281261B (en) 2022-11-01
JP2017114876A (ja) 2017-06-29
JP2015134793A (ja) 2015-07-27
CA3096084C (en) 2022-12-20
IL237505A0 (en) 2015-04-30
KR20190016595A (ko) 2019-02-18
KR101947332B1 (ko) 2019-02-12
IL281261A (en) 2021-04-29
US20170283450A1 (en) 2017-10-05
IL281261B2 (en) 2023-03-01
KR20180014211A (ko) 2018-02-07
WO2009126737A3 (en) 2010-01-14
CA3096084A1 (en) 2009-10-15
KR101651695B1 (ko) 2016-08-26
KR20110003523A (ko) 2011-01-12
JP2019073530A (ja) 2019-05-16
KR102453184B1 (ko) 2022-10-07
KR20210062717A (ko) 2021-05-31
US11447515B2 (en) 2022-09-20
JP6770596B2 (ja) 2020-10-14
JP2011516566A (ja) 2011-05-26
JP6786410B2 (ja) 2020-11-18
CA2720771A1 (en) 2009-10-15
EP3357931A1 (en) 2018-08-08
CA2993582A1 (en) 2009-10-15
IL239051B (en) 2021-03-25
KR20200024964A (ko) 2020-03-09
ES2827804T3 (es) 2021-05-24
EP2280987B1 (en) 2018-05-23
WO2009126737A2 (en) 2009-10-15

Similar Documents

Publication Publication Date Title
IL281261A (en) Triterpene saponins, methods of preparation and uses thereof
HK1168099A1 (zh) 糖苷衍生物及其用途
IL209188A (en) Sweetener, preparations containing it and methods of manufacture
IL211541A0 (en) Co-crystal compositions, methods of producing the same and uses thereof
HK1194071A1 (en) Certain triazolopyrazines, compositions thereof and methods of use therefor
EP2445894A4 (en) KETAL COMPOUNDS AND USES THEREOF
HK1144772A1 (en) Protopanaxadiol-type ginsenoside compositions and uses thereof
IL218814A0 (en) Pyrazoline dione derivatives, processes for producing the same, compositions comprising the same and uses thereof
EP2349305A4 (en) PHYTOCHEMICAL COMPOSITIONS AND METHOD FOR AMP-KINASE ACTIVATION
HK1167240A1 (zh) 使用芳基哌嗪類化合物的組合，合成和方法
ZA201008553B (en) Steroidal compounds as melanogenesis modifiers and uses thereof
EP2460812A4 (en) STEROL DERIVATIVES AND THEIR SYNTHESIS AND USE
EP2375911A4 (en) CHOCOLATE EXTRACT, METHOD OF MAKING SAME, AND USES THEREOF
EP2296675A4 (en) ECHINODERM EXTRACTS, MANUFACTURING METHODS AND ITS USES
EP2240190A4 (en) NUTRITIONAL COMPOSITION AND METHOD OF USE
EP2350212A4 (en) POLYAMINO-ACETONITRILES, PROCESSES FOR PREPARING THEM AND USE THEREOF
EP2231173A4 (en) NUTRITIONAL COMPOSITION AND METHOD OF USE
EP2567966A4 (en) NEW SYNTHESIS DERIVATIVE OF ECDYSTERONE, PREPARATION METHOD AND USE OF SAID DERIVATIVE
PL383867A1 (pl) Sposób otrzymywania 4-N-furfurylocytozyny, kompozycja antystarzeniowa oraz zastosowanie 4-N-furfurylocytozyny do wytwarzania kompozycji antystarzeniowej
AU2009904624A0 (en) Herbal mixtures, methods of making them and methods of using them
AU2008904917A0 (en) Herbal mixtures, methods of making them and methods of using them
HK1101487A2 (en) The extractive of aweto and process for its preparation and uses
EP2475436A4 (en) COMPOSITIONS, MATERIALS INCORPORATING COMPOSITIONS AND METHODS OF USE OF COMPOSITIONS AND MATERIALS