CA3003483C - Triterpene saponin analogues - Google Patents

Triterpene saponin analogues Download PDF

Info

Publication number
CA3003483C
CA3003483C CA3003483A CA3003483A CA3003483C CA 3003483 C CA3003483 C CA 3003483C CA 3003483 A CA3003483 A CA 3003483A CA 3003483 A CA3003483 A CA 3003483A CA 3003483 C CA3003483 C CA 3003483C
Authority
CA
Canada
Prior art keywords
group
antigen
nitrogen
oxygen
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
CA3003483A
Other languages
English (en)
French (fr)
Other versions
CA3003483A1 (en
Inventor
David Y. Gin (Deceased)
Eric CHEA
Alberto FERNANDEZ-TEJADA
Jeffrey Gardner
Jason Lewis
Philip Livingston
J. Tyler Martin
Lars Nordstroem
Naga Vara Kishore PILLARSETTY
Govind Ragupathi
Derek Tan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Memorial Sloan Kettering Cancer Center
Adjuvance Technologies Inc
Original Assignee
Memorial Sloan Kettering Cancer Center
Adjuvance Technologies Inc
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 Memorial Sloan Kettering Cancer Center, Adjuvance Technologies Inc filed Critical Memorial Sloan Kettering Cancer Center
Publication of CA3003483A1 publication Critical patent/CA3003483A1/en
Application granted granted Critical
Publication of CA3003483C publication Critical patent/CA3003483C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • 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
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/02—Bacterial antigens
    • A61K39/08—Clostridium, e.g. Clostridium tetani
    • 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
    • A61K39/02—Bacterial antigens
    • A61K39/099—Bordetella
    • 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
    • A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
    • 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
    • A61P31/20—Antivirals for DNA viruses
    • 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
    • C07H13/04—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 attached to acyclic carbon atoms
    • 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
    • C07H13/04—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 attached to acyclic carbon atoms
    • C07H13/06—Fatty acids
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
    • 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
    • A61K39/02—Bacterial antigens
    • A61K2039/10—Brucella; Bordetella, e.g. Bordetella pertussis; Not used, see subgroups
    • 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
    • A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
    • A61K2039/55511—Organic adjuvants
    • A61K2039/55577—Saponins; Quil A; QS21; ISCOMS
    • 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
    • A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
    • A61K2039/55511—Organic adjuvants
    • A61K2039/55583—Polysaccharides
    • 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)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Immunology (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Virology (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)
  • Medicinal Preparation (AREA)
CA3003483A 2015-11-06 2016-11-04 Triterpene saponin analogues Active CA3003483C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201562252296P 2015-11-06 2015-11-06
US62/252,296 2015-11-06
US201562268837P 2015-12-17 2015-12-17
US62/268,837 2015-12-17
PCT/US2016/060564 WO2017079582A1 (en) 2015-11-06 2016-11-04 Triterpene saponin analogues

Publications (2)

Publication Number Publication Date
CA3003483A1 CA3003483A1 (en) 2017-05-11
CA3003483C true CA3003483C (en) 2022-09-13

Family

ID=58662549

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3003483A Active CA3003483C (en) 2015-11-06 2016-11-04 Triterpene saponin analogues

Country Status (12)

Country Link
US (5) US20180327436A1 (https=)
EP (2) EP4001290A1 (https=)
JP (3) JP6900385B2 (https=)
KR (1) KR20180077180A (https=)
CN (2) CN112812143A (https=)
AU (1) AU2016349693B2 (https=)
CA (1) CA3003483C (https=)
CL (1) CL2018001192A1 (https=)
IL (3) IL286493B (https=)
SG (2) SG10202012205XA (https=)
WO (1) WO2017079582A1 (https=)
ZA (1) ZA201802891B (https=)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CA3003483C (en) * 2015-11-06 2022-09-13 Adjuvance Technologies, Inc. Triterpene saponin analogues
EP3609505A4 (en) * 2017-04-13 2021-04-28 Adjuvance Technologies, Inc. TRITERPEN-SAPONIN SYNTHESIS, INTERMEDIATES AND COMBINATIONS OF ADJUVANCES
CN110730666A (zh) * 2017-04-25 2020-01-24 佐剂技术公司 三萜皂苷类似物
EP3618836A4 (en) 2017-04-25 2021-01-13 Adjuvance Technologies, Inc. TRITERPENSAPONINALOGA
WO2019079160A1 (en) 2017-10-16 2019-04-25 Adjuvance Technologies, Inc. TRITERPENIC SAPONIN ANALOGS
US20230128815A1 (en) * 2020-03-23 2023-04-27 Adjuvance Technologies, Inc. Adjuvant compounds, salt forms, and formulations
WO2021236809A2 (en) 2020-05-19 2021-11-25 Othair Prothena Limited Multi-epitope vaccine for the treatment of alzheimer's disease
KR20230080397A (ko) 2020-08-07 2023-06-07 오타이르 프로테나 리미티드 알츠하이머 질환을 치료하기 위한 멀티에피토프 백신
WO2023056089A1 (en) 2021-10-03 2023-04-06 Eisai R&D Management Co., Ltd. Immunological adjuvant formulations comprising tlr4 agonist e6020
US20250025550A1 (en) * 2021-11-08 2025-01-23 Adjuvance Technologies, Inc. Adjuvant compounds and formulations
EP4190359A1 (en) 2021-12-03 2023-06-07 Asociación Centro de Investigación Cooperativa en Biociencias - CIC bioGUNE Saponin-based adjuvants and vaccines
WO2023139145A1 (en) 2022-01-19 2023-07-27 Asociación Centro De Investigación Cooperativa En Biociencias-Cic Biogune Saponin-based adjuvants and vaccines
CN117106004A (zh) * 2022-05-17 2023-11-24 北京科兴中维生物技术有限公司 三萜皂苷化合物及其制备方法及应用
WO2024218268A1 (en) 2023-04-20 2024-10-24 Asociación Centro De Investigación Cooperativa En Biociencias-Cic Biogune Saponin derivatives as adjuvants and photoaffinity probes
WO2024261351A2 (en) 2024-05-08 2024-12-26 Vaccine Formulation Institute Ch Ltd. Immunologically active saponin fractions and adjuvant formulations

Family Cites Families (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5341202B2 (https=) 1974-03-12 1978-11-01
US5231112A (en) 1984-04-12 1993-07-27 The Liposome Company, Inc. Compositions containing tris salt of cholesterol hemisuccinate and antifungal
US5916588A (en) 1984-04-12 1999-06-29 The Liposome Company, Inc. Peptide-containing liposomes, immunogenic liposomes and methods of preparation and use
US4769239A (en) 1984-08-21 1988-09-06 Merck & Co., Inc. Vaccine against varicella-zoster virus
US4684479A (en) 1985-08-14 1987-08-04 Arrigo Joseph S D Surfactant mixtures, stable gas-in-liquid emulsions, and methods for the production of such emulsions from said mixtures
US6759057B1 (en) 1986-06-12 2004-07-06 The Liposome Company, Inc. Methods and compositions using liposome-encapsulated non-steroidal anti-inflammatory drugs
IE60901B1 (en) 1986-08-21 1994-08-24 Vestar Inc Improved treatment of systemic fungal infections with phospholipid particles encapsulating polyene antifungal antibiotics
US6406713B1 (en) 1987-03-05 2002-06-18 The Liposome Company, Inc. Methods of preparing low-toxicity drug-lipid complexes
US5583112A (en) 1987-05-29 1996-12-10 Cambridge Biotech Corporation Saponin-antigen conjugates and the use thereof
AU598958B2 (en) 1987-11-12 1990-07-05 Vestar, Inc. Improved amphotericin b liposome preparation
US5215680A (en) 1990-07-10 1993-06-01 Cavitation-Control Technology, Inc. Method for the production of medical-grade lipid-coated microbubbles, paramagnetic labeling of such microbubbles and therapeutic uses of microbubbles
AU687355B2 (en) 1992-07-17 1998-02-26 Merck Sharp & Dohme Corp. Method for preventing zoster or alleviating varicella related post-herpetic neuralgia
UA56132C2 (uk) 1995-04-25 2003-05-15 Смітклайн Бічем Байолоджікалс С.А. Композиція вакцини (варіанти), спосіб стабілізації qs21 відносно гідролізу (варіанти), спосіб приготування композиції вакцини
CA2263455C (en) 1996-08-23 2002-10-29 Sequus Pharmaceuticals, Inc. Liposomes containing a cisplatin compound
US6056973A (en) 1996-10-11 2000-05-02 Sequus Pharmaceuticals, Inc. Therapeutic liposome composition and method of preparation
EP0932390A1 (en) 1996-10-11 1999-08-04 Sequus Pharmaceuticals, Inc. Therapeutic liposome composition and method
SK283760B6 (sk) 1996-10-15 2004-01-08 The Liposome Company, Inc. Farmaceutický prostriedok na dopravu bioaktívnych látok
US6080725A (en) * 1997-05-20 2000-06-27 Galenica Pharmaceuticals, Inc. Immunostimulating and vaccine compositions employing saponin analog adjuvants and uses thereof
ES2298316T3 (es) 1997-09-05 2008-05-16 Glaxosmithkline Biologicals S.A. Emulsiones de aceite en agua que contienen saponinas.
WO2000009075A2 (en) * 1998-08-14 2000-02-24 Galenica Pharmaceuticals, Inc. Chemically modified saponins and the use thereof as adjuvants
AU7085400A (en) 1999-09-02 2001-03-26 Antigenics, Inc. Compositions of immunostimulatory polymers and saponin adjuvants and uses thereof
GB0401239D0 (en) 2004-01-21 2004-02-25 Molecularnature Ltd Adjuvant compositions
GB0504436D0 (en) 2005-03-03 2005-04-06 Glaxosmithkline Biolog Sa Vaccine
TWI457133B (zh) 2005-12-13 2014-10-21 Glaxosmithkline Biolog Sa 新穎組合物
GB0700562D0 (en) * 2007-01-11 2007-02-21 Novartis Vaccines & Diagnostic Modified Saccharides
BRPI0811228A2 (pt) 2007-05-24 2014-10-21 Glaxonsmithkline Biolog S A Composição liofilizada, e, métodos para produzir uma composição liofilizada e para produzir uma composição imunológica.
CA2708716A1 (en) 2007-12-21 2009-07-02 Glaxosmithkline Biologicals S.A. Vaccines for malaria
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
SI2271360T1 (sl) 2008-04-16 2015-12-31 Glaxosmithkline Biologicals S.A. Cepivo
GB0910046D0 (en) 2009-06-10 2009-07-22 Glaxosmithkline Biolog Sa Novel compositions
ES2443952T3 (es) 2009-09-02 2014-02-21 Novartis Ag Composiciones inmunógenas que incluyen moduladores de la actividad de TLR
AU2012255132B2 (en) 2011-05-17 2017-05-25 Soligenix, Inc. Thermostable vaccine compositions and methods of preparing same
WO2012156391A1 (en) 2011-05-17 2012-11-22 Glaxosmithkline Biologicals S.A. Vaccine against streptococcus pneumoniae
US20130309273A1 (en) 2012-05-17 2013-11-21 Kimberly Hassett Thermostable Vaccine Compositions and Methods of Preparing Same
WO2014124860A1 (en) 2013-02-14 2014-08-21 Boehringer Ingelheim International Gmbh Specific pde4b-inhibitors for the treatment of diabetes mellitus
US20150037374A1 (en) 2013-07-31 2015-02-05 Csl Limited Anti-tumor compositions and uses thereof
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
WO2016096968A1 (en) 2014-12-18 2016-06-23 Glaxosmithkline Biologicals S.A. Vaccination
CA3003483C (en) 2015-11-06 2022-09-13 Adjuvance Technologies, Inc. Triterpene saponin analogues
US11629162B2 (en) 2015-12-17 2023-04-18 Memorial Sloan-Kettering Cancer Center Triterpene saponin variants, methods of synthesis and use thereof
GB201621686D0 (en) 2016-12-20 2017-02-01 Glaxosmithkline Biologicals Sa Novel methods for inducing an immune response
EP3609505A4 (en) 2017-04-13 2021-04-28 Adjuvance Technologies, Inc. TRITERPEN-SAPONIN SYNTHESIS, INTERMEDIATES AND COMBINATIONS OF ADJUVANCES
CN110730666A (zh) 2017-04-25 2020-01-24 佐剂技术公司 三萜皂苷类似物
EP3618836A4 (en) 2017-04-25 2021-01-13 Adjuvance Technologies, Inc. TRITERPENSAPONINALOGA
CA3078223A1 (en) 2017-09-08 2019-03-14 Infectious Disease Research Institute Liposomal formulations comprising saponin and methods of use
WO2019079160A1 (en) 2017-10-16 2019-04-25 Adjuvance Technologies, Inc. TRITERPENIC SAPONIN ANALOGS
US20190275134A1 (en) 2018-03-12 2019-09-12 Janssen Pharmaceuticals, Inc Vaccines against urinary tract infections
CA3157372A1 (en) 2019-11-05 2021-05-14 Adjuvance Technologies, Inc. Varicella zoster

Also Published As

Publication number Publication date
US20240327443A1 (en) 2024-10-03
US20180327436A1 (en) 2018-11-15
ZA201802891B (en) 2020-01-29
US10906926B2 (en) 2021-02-02
IL293848B2 (en) 2025-02-01
CN108778289A (zh) 2018-11-09
US12037355B2 (en) 2024-07-16
EP3370730A1 (en) 2018-09-12
JP2021152043A (ja) 2021-09-30
AU2016349693B2 (en) 2022-08-11
IL293848A (en) 2022-08-01
CL2018001192A1 (es) 2018-11-23
KR20180077180A (ko) 2018-07-06
IL259145B (en) 2021-09-30
CN112812143A (zh) 2021-05-18
IL286493B (en) 2022-07-01
CA3003483A1 (en) 2017-05-11
SG10202012205XA (en) 2021-01-28
EP3370730A4 (en) 2019-07-31
US20200239509A1 (en) 2020-07-30
CN108778289B (zh) 2020-11-17
IL293848B1 (en) 2024-10-01
EP4001290A1 (en) 2022-05-25
JP6900385B2 (ja) 2021-07-07
JP2018537527A (ja) 2018-12-20
IL286493A (en) 2021-10-31
SG11201803594TA (en) 2018-05-30
AU2016349693A1 (en) 2018-05-17
US20210002316A1 (en) 2021-01-07
JP2023012519A (ja) 2023-01-25
US20230219991A1 (en) 2023-07-13
IL259145A (en) 2018-06-28
WO2017079582A1 (en) 2017-05-11

Similar Documents

Publication Publication Date Title
US12037355B2 (en) Triterpene saponin analogues
US20230357300A1 (en) Triterpene saponin synthesis, intermediates and adjuvant combinations
JP7177082B2 (ja) トリテルペンサポニン類似物
US12569554B2 (en) Triterpene saponin analogues
JP2021152043A5 (https=)
US20260115281A1 (en) Triterpene saponin analogues
HK40042493A (en) Triterpene saponin analogues
HK40016648A (en) Triterpene saponin analogues
HK1260769A1 (en) Triterpene saponin analogues
HK1260769B (en) Triterpene saponin analogues

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20191211

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 8TH ANNIV.) - STANDARD

Year of fee payment: 8

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20241028

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT

Effective date: 20241028

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20241028

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 9TH ANNIV.) - STANDARD

Year of fee payment: 9

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20251107

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20251107

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-4-4-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20251217