WO2008010776A1 - Aigialomycine d et ses dérivés et leur utilisation dans le traitement de cancer ou de paludisme ou d'infection microbienne - Google Patents

Aigialomycine d et ses dérivés et leur utilisation dans le traitement de cancer ou de paludisme ou d'infection microbienne Download PDF

Info

Publication number
WO2008010776A1
WO2008010776A1 PCT/SG2007/000216 SG2007000216W WO2008010776A1 WO 2008010776 A1 WO2008010776 A1 WO 2008010776A1 SG 2007000216 W SG2007000216 W SG 2007000216W WO 2008010776 A1 WO2008010776 A1 WO 2008010776A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrogen
group
aigialomycin
carbon atoms
derivative
Prior art date
Application number
PCT/SG2007/000216
Other languages
English (en)
Inventor
Anqi Chen
Quang Vu Nguyen
Original Assignee
Agency For Science, Technology And Research
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 Agency For Science, Technology And Research filed Critical Agency For Science, Technology And Research
Priority to US12/374,610 priority Critical patent/US20100041745A1/en
Publication of WO2008010776A1 publication Critical patent/WO2008010776A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06—Antimalarials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/16—Eight-membered rings
    • C07D313/20—Eight-membered rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
    • 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

Definitions

  • a third synthesis disclosed a solid-phase synthesis strategy for aigialomycin D and analogues modified at the C5'-C6' region whose inhibition on certain kinases was found to be less potent than aigialomycin D itself. The synthesis is difficult to scale up, and is capable of generating only limited analogues of aigialomycin D.
  • Aryl groups may include for example optionally substituted phenyl, naphthyl, anthracyl, biphenyl, terphenyl etc.
  • the terminology (H, H) here indicates that each oxygen atom is attached to a hydrogen atom, i.e. the group incorp is:
  • Suitable solvents include polar aprotic solvents such as diethyl ether, dichloromethane, dichloroethane, chloroform, etc. or mixtures thereof.
  • Other alternatives for the coupling of 4 and 5 are well known in the literature.
  • conversion of benzoic acid 4 to the corresponding benzoyl chloride activates it to reaction with compound 5, either with X being O or X being NR 3 .
  • Other alternatives for this reaction include DCC mediated coupling of an acid to an alcohol.
  • acid 4 may be converted to an anhydride (either symmetrical or a mixed anhydride, for example with a simple acid such as acetic acid) and reaction of the anhydride with olefin 5.
  • non-toxic parenterally acceptable diluents or carriers can include, Ringer's solution, isotonic saline, phosphate buffered saline, ethanol and 1,2 propylene glycol.
  • the emulsions for oral administration may further comprise one or more emulsifying agents.
  • Suitable emulsifying agents include dispersing agents as exemplified above or natural gums such as guar gum, gum acacia or gum tragacanth.
  • Methods for preparing parenterally administrable compositions are apparent to those skilled in the art, and are described in more detail in, for example, Remington's Pharmaceutical Science, 15th ed., Mack Publishing Company, Easton, Pa., hereby incorporated by reference herein.
  • the composition may incorporate any suitable surfactant such as an anionic, cationic or non-ionic surfactant such as sorbitan esters or polyoxyethylene derivatives thereof.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de fabrication d'un composé (2), qui consiste à cycliser un diène (3). Le composé (2) peut être l'aigialomycine D ou un dérivé de celle-ci; il peut en outre être élaboré de manière à obtenir l'aigialomycine ou un dérivé de celle-ci. De plus, le composé (2) ou son dérivé peut être utilisé pour le traitement de cancer, de paludisme ou d'infection microbienne.
PCT/SG2007/000216 2006-07-21 2007-07-20 Aigialomycine d et ses dérivés et leur utilisation dans le traitement de cancer ou de paludisme ou d'infection microbienne WO2008010776A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US12/374,610 US20100041745A1 (en) 2006-10-11 2007-07-20 Aigialomycin D and Derivatives Thereof and Their Use in Treating Cancer or Malaria or a Microbial Infection

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US82900506 2006-07-21
US60/829,005 2006-10-11

Publications (1)

Publication Number Publication Date
WO2008010776A1 true WO2008010776A1 (fr) 2008-01-24

Family

ID=38957035

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SG2007/000216 WO2008010776A1 (fr) 2006-07-21 2007-07-20 Aigialomycine d et ses dérivés et leur utilisation dans le traitement de cancer ou de paludisme ou d'infection microbienne

Country Status (1)

Country Link
WO (1) WO2008010776A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105683198A (zh) * 2013-11-04 2016-06-15 卫材R&D管理有限公司 软海绵素b的类似物合成中有用的大环化反应和中间体
US9802953B2 (en) 2007-10-03 2017-10-31 Eisai R&D Management Co., Ltd. Intermediates and methods for the synthesis of halichondrin B analogs
US9856276B2 (en) 2010-01-26 2018-01-02 Eisai R&D Management Co., Ltd. Compounds useful in the synthesis of halichondrin B analogs
CN107849057A (zh) * 2015-05-07 2018-03-27 卫材R&D管理有限公司 用于合成软海绵素大环内酯的大环化反应及中间体和其他片段
US10030032B2 (en) 2013-12-06 2018-07-24 Eisai R&D Management Co., Ltd. Methods useful in the synthesis of halichondrin B analogs
JP2018526602A (ja) * 2015-07-23 2018-09-13 キュンドン ナビエン シーオー．，エルティーディー． 熱交換器
USRE47797E1 (en) 2004-06-03 2020-01-07 Eisai R&D Management Co., Ltd. Intermediates for the preparation of analogs of halichondrin B
US10676481B2 (en) 2016-02-12 2020-06-09 Eisai R&D Management Co., Ltd. Intermediates in the synthesis of eribulin and related methods of synthesis
US11136335B2 (en) 2016-06-30 2021-10-05 Eisai R&D Management Co., Ltd. Prins reaction and intermediates useful in the synthesis of halichondrin macrolides and analogs thereof
US11542269B2 (en) 2018-01-03 2023-01-03 Eisai R&D Management Co., Ltd. Prins reaction and compounds useful in the synthesis of halichondrin macrolides and analogs thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005061481A1 (fr) * 2003-12-19 2005-07-07 Sloan-Kettering Institute For Cancer Research Nouveaux macrocycles et leurs utilisations

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005061481A1 (fr) * 2003-12-19 2005-07-07 Sloan-Kettering Institute For Cancer Research Nouveaux macrocycles et leurs utilisations

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
BARLUENGA S. ET AL.: "Modular Asymmetric Synthesis of Aigialomycin D, Kinase-Inhibitory Scaffold", ANGEW. CHEM. INT. ED., vol. 45, 2006, pages 3951 - 3954 *
GENG X. ET AL.: "Total Synthesis of Aigialomycin D", J. ORG. LETT., vol. 6, no. 3, 2004, pages 413 - 416 *
ISAKA M. ET AL.: "Aigialomycins A-E, New Resorcinylic Macrolides from the Marine Mangrove Fungus Aigialus parvus", J. ORG. CHEM., vol. 67, no. 5, 2002, pages 1561 - 1566 *
LU J. ET AL.: "Enantioselective Total Synthesis of Aigialomycin D", TETRAHEDRON: ASYMMETRY, vol. 17, no. 7, 2006, pages 1066 - 1073, XP024962126, DOI: doi:10.1016/j.tetasy.2006.03.027 *
VONGVILAI P.J. ET AL.: "Ketene Acetal and Spiroacetal Constituents of the Marine Fungus Aigialus parvus BCC 5311", J. NAT. PROD., vol. 67, no. 3, 2004, pages 457 - 460, XP008117853, DOI: doi:10.1021/np030344d *
YANG Z.-Q. ET AL.: "New Efficient Synthesis of Resorcinylic Macrolides via Ynolides: Establishment of Cycloproparadicicol as Synthetically Feasible Preclinical Anticancer Agent Based on Hsp90 as the Target", JACS, vol. 126, no. 25, 2004, pages 7881 - 7889 *

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE47797E1 (en) 2004-06-03 2020-01-07 Eisai R&D Management Co., Ltd. Intermediates for the preparation of analogs of halichondrin B
US10717743B2 (en) 2007-10-03 2020-07-21 Eisai R&D Management Co., Ltd. Intermediates and methods for the synthesis of halichondrin B analogs
US10214539B2 (en) 2007-10-03 2019-02-26 Eisai R&D Management Co., Ltd. Intermediates and methods for the synthesis of halichondrin B analogs
US9802953B2 (en) 2007-10-03 2017-10-31 Eisai R&D Management Co., Ltd. Intermediates and methods for the synthesis of halichondrin B analogs
US10494388B2 (en) 2010-01-26 2019-12-03 Eisai R&D Management Co., Ltd. Compounds useful in the synthesis of halichondrin B analogs
US9856276B2 (en) 2010-01-26 2018-01-02 Eisai R&D Management Co., Ltd. Compounds useful in the synthesis of halichondrin B analogs
US11643418B2 (en) 2013-11-04 2023-05-09 Eisai R&D Management Co., Ltd. Macrocyclization reactions and intermediates and other fragments useful in the synthesis of analogs of halichondrin B
CN105683198A (zh) * 2013-11-04 2016-06-15 卫材R&D管理有限公司 软海绵素b的类似物合成中有用的大环化反应和中间体
US9783549B2 (en) 2013-11-04 2017-10-10 Eisai R&D Management Co., Ltd. Macrocyclization reactions and intermediates useful in the synthesis of analogs of halichondrin B
US10221189B2 (en) 2013-11-04 2019-03-05 Eisai R&D Management Co., Ltd. Macrocyclization reactions and intermediates useful in the synthesis of analogs of halichondrin B
CN105683198B (zh) * 2013-11-04 2019-03-12 卫材R&D管理有限公司 软海绵素b的类似物合成中有用的大环化反应和中间体
US10934307B2 (en) 2013-11-04 2021-03-02 Eisai R&D Management Co., Ltd. Macrocyclization reactions and intermediates and other fragments useful in the synthesis of analogs of halichondrin B
EP3066102A4 (fr) * 2013-11-04 2017-04-26 Eisai R&D Management Co., Ltd. Réactions de macrocyclisation et intermédiaires utiles dans la synthèse d'analogues de l'halichondrine b
EP3066102A1 (fr) * 2013-11-04 2016-09-14 Eisai R&D Management Co., Ltd. Réactions de macrocyclisation et intermédiaires utiles dans la synthèse d'analogues de l'halichondrine b
US10611773B2 (en) 2013-11-04 2020-04-07 Eisai R&D Management Co., Ltd. Macrocyclization reactions and intermediates and other fragments useful in the synthesis of analogs of halichondrin B
US10030032B2 (en) 2013-12-06 2018-07-24 Eisai R&D Management Co., Ltd. Methods useful in the synthesis of halichondrin B analogs
US10450324B2 (en) 2013-12-06 2019-10-22 Eisai R&D Management Co., Ltd. Methods useful in the synthesis of halichondrin B analogs
CN107849057A (zh) * 2015-05-07 2018-03-27 卫材R&D管理有限公司 用于合成软海绵素大环内酯的大环化反应及中间体和其他片段
CN107849057B (zh) * 2015-05-07 2020-11-10 卫材R&D管理有限公司 用于合成软海绵素大环内酯的大环化反应及中间体和其他片段
US10913749B2 (en) 2015-05-07 2021-02-09 Eisai R&D Management Co., Ltd. Macrocyclization reactions and intermediates and other fragments useful in the synthesis of halichondrin macrolides
US10308661B2 (en) 2015-05-07 2019-06-04 Eisai R&D Management Co., Ltd. Macrocyclization reactions and intermediates and other fragments useful in the synthesis of halichondrin macrolides
JP2018526602A (ja) * 2015-07-23 2018-09-13 キュンドン ナビエン シーオー．，エルティーディー． 熱交換器
US10676481B2 (en) 2016-02-12 2020-06-09 Eisai R&D Management Co., Ltd. Intermediates in the synthesis of eribulin and related methods of synthesis
US11136335B2 (en) 2016-06-30 2021-10-05 Eisai R&D Management Co., Ltd. Prins reaction and intermediates useful in the synthesis of halichondrin macrolides and analogs thereof
US11542269B2 (en) 2018-01-03 2023-01-03 Eisai R&D Management Co., Ltd. Prins reaction and compounds useful in the synthesis of halichondrin macrolides and analogs thereof

Similar Documents

Publication Publication Date Title
WO2008010776A1 (fr) Aigialomycine d et ses dérivés et leur utilisation dans le traitement de cancer ou de paludisme ou d'infection microbienne
Abelman et al. Construction of quaternary carbon centers by palladium-catalyzed intramolecular alkene insertions. Total synthesis of the Amaryllidaceae alkaloids (.+-.)-tazettine and (.+-.)-6a-epipretazettine
Cases et al. Synthetic studies towards furanocembrane diterpenes. A total synthesis of bis-deoxylophotoxin
KR20180061159A (ko) 베라프로스트의 제조 방법
US20090093651A1 (en) Process for preparation of 13,14-dihydro-pgf2 alpha derivatives
Schwenter et al. A New, Non‐Iterative Asymmetric Synthesis of Long‐Chain 1, 3‐Polyols
Jung et al. Synthesis of a trans, syn, trans-Dodecahydrophenanthrene via a Bicyclic Transannular Diels− Alder Reaction: Intermediate for the Synthesis of Fusidic Acid
RU2478630C2 (ru) Промежуточные соединения и способы получения зеараленоновых макролидных аналогов
US20100041745A1 (en) Aigialomycin D and Derivatives Thereof and Their Use in Treating Cancer or Malaria or a Microbial Infection
Veeranjaneyulu et al. Stereoselective total synthesis of botryolide E
Chen et al. Total synthesis of γ-trifluoromethylated analogs of goniothalamin and their derivatives
Reddy et al. Stereoselective Total Synthesis of the Natural Oxylipin (6R, 7E, 9R, 10S)-6, 9, 10-Trihydroxyoctadec-7-enoic Acid1
WO2006083417A2 (fr) Procedes de preparation de tashironine sesquiterpenoide, ses analogues et leurs utilisations
Wang et al. Asymmetric Total Synthesis of (−)‐Cladospolide B
JP5698128B2 (ja) ジヒドロキシヘキセン酸エステル及びその製造方法
Yip Total Synthesis of Maltepolide E and Congeners Using Diene-Ene Ring-Closing Mathesis as the Key Step
WO2024032799A1 (fr) Procédé de préparation de tétrodotoxine et de son analogue
Salva Reddy et al. Stereoselective Total Synthesis of the Natural Oxylipin (6R, 7E, 9R, 10S)‐6, 9, 10‐Trihydroxyoctadec‐7‐enoic Acid
KR101123847B1 (ko) 오셀타미비어(타미플루)의 제조 방법
Roushanbakhti Synthesis of the EFG-ring system of pectenotoxin-4
Dubasi et al. Studies towards the Total Synthesis of (+)-Discodermolide: Desymmetrization Approach
Yudhipratama Synthetic Studies towards Opaliferin, a Tetracyclic Polyketide Metabolite
Narasimhaswamy et al. Studies toward the total synthesis of (+)-Discodermolide: Desymmetrization approach
Pollard Synthetic Efforts Towards the Synthesis of Prostaglandin PGF2a
JP3785849B2 (ja) 光学活性ノルボルネンアルデヒド類の製造法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07794230

Country of ref document: EP

Kind code of ref document: A1

DPE1 Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101)
NENP Non-entry into the national phase

Ref country code: DE

NENP Non-entry into the national phase

Ref country code: RU

WWE Wipo information: entry into national phase

Ref document number: 12374610

Country of ref document: US

122 Ep: pct application non-entry in european phase

Ref document number: 07794230

Country of ref document: EP

Kind code of ref document: A1

DPE1 Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101)