WO2022094711A1 - Procédé de préparation d'intermédiaire avancé pour la synthèse d'éribuline - Google Patents

Procédé de préparation d'intermédiaire avancé pour la synthèse d'éribuline Download PDF

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Publication number
WO2022094711A1
WO2022094711A1 PCT/CA2021/051567 CA2021051567W WO2022094711A1 WO 2022094711 A1 WO2022094711 A1 WO 2022094711A1 CA 2021051567 W CA2021051567 W CA 2021051567W WO 2022094711 A1 WO2022094711 A1 WO 2022094711A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
formula
converting
protecting group
parts
Prior art date
Application number
PCT/CA2021/051567
Other languages
English (en)
Inventor
Jason BEXRUD
Alena Rudolph
Boris Gorin
Huimin ZHAI
Kiem Nguyen
Anne Luong
Dino Alberico
Original Assignee
Eurofins Cdmo Alphora 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 Eurofins Cdmo Alphora Inc. filed Critical Eurofins Cdmo Alphora Inc.
Publication of WO2022094711A1 publication Critical patent/WO2022094711A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed 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
    • C07D317/72—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 spiro-condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • C07D493/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • 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
    • C07H15/207—Cyclohexane rings not substituted by nitrogen atoms, e.g. kasugamycins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Definitions

  • Halichondrins have been disclosed as having anti-cancer and antimitotic activity (Chem. Rev. 2009, 109, 3044-3079, incorporated herein by reference).
  • Halichondrin B has been reported as a potent anticancer agent that was first isolated from the marine sponge Halichondra okadai (US 5,436,238; Tetrahedron Lett. 1994, 35, 9435 and WO 1993/017690 Al, all incorporated herein by reference). It was further reported that analogs of Halichondrin B bearing only macrocyclic fragment of its molecule (Cl - C30 fragment) and having a ketone function instead of ester at Cl position demonstrate anticancer activity similar to Halichondrin B (Bioorg. Med. Chem.
  • PG 1 can be a benzylidene ketal
  • PG 2 can be benzyl
  • PG 3 can be acetyl
  • the compound of formula 10 can be reacted with a base for removal of the protecting group PG 3 , which can undergo an intramolecular cyclization to form the compound of formula 11.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

L'invention concerne un procédé de préparation d'un composé de formule 13, et des intermédiaires préparés et utilisés dans la préparation du composé de formule 13.
PCT/CA2021/051567 2020-11-05 2021-11-04 Procédé de préparation d'intermédiaire avancé pour la synthèse d'éribuline WO2022094711A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CA3,098,164 2020-11-05
CA3098164A CA3098164A1 (fr) 2020-11-05 2020-11-05 Procede de preparation d'un intermediaire avance pour la synthese d'eribuline

Publications (1)

Publication Number Publication Date
WO2022094711A1 true WO2022094711A1 (fr) 2022-05-12

Family

ID=81393264

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA2021/051567 WO2022094711A1 (fr) 2020-11-05 2021-11-04 Procédé de préparation d'intermédiaire avancé pour la synthèse d'éribuline

Country Status (2)

Country Link
CA (1) CA3098164A1 (fr)
WO (1) WO2022094711A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005118565A1 (fr) * 2004-06-03 2005-12-15 Eisai Co., Ltd. Intermediaires pour la preparation d'halichondrine b
WO2013158746A1 (fr) * 2012-04-18 2013-10-24 Biocryst Pharmaceuticals, Inc. Compositions et procédés d'inhibition d'une polymérase virale
CN110835353A (zh) * 2018-08-15 2020-02-25 上海茂晟康慧科技有限公司 一种艾日布林中间体er804698的合成方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005118565A1 (fr) * 2004-06-03 2005-12-15 Eisai Co., Ltd. Intermediaires pour la preparation d'halichondrine b
WO2013158746A1 (fr) * 2012-04-18 2013-10-24 Biocryst Pharmaceuticals, Inc. Compositions et procédés d'inhibition d'une polymérase virale
CN110835353A (zh) * 2018-08-15 2020-02-25 上海茂晟康慧科技有限公司 一种艾日布林中间体er804698的合成方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHOI, HYEONG-WOOK; DEMEKE, DAMTEW; KANG, FU-AN; KISHI, YOSHITO; NAKAJIMA, KATSUMASA; NOWAK, PAWEL; WAN, ZHAO-KUI; XIE, CHAOYU: "Synthetic studies on the marine natural product halichondrins", PURE & APPLIED CHEMISTRY, vol. 75, no. 1, 1 January 2003 (2003-01-01), GB , pages 1 - 17, XP009138327, ISSN: 0033-4545 *
KIM BOK YOUNG, JOONG BOK AHN, HONG WOO LEE, KYOUNG SIK MOON, TAE BO SIM, JAE SOO SHIN, SOON KIL AHN, AND CHUNG IL HONG: "Synthesis and Antihyperglycemic Activity of Erythrose, Ribose and Substituted Pyrrolidine Containing Thiazolidinedione Derivatives", CHEMICAL AND PHARMACEUTICAL BULLETIN, vol. 51, no. 3, 1 January 2003 (2003-01-01), JP , pages 276 - 285, XP055939957, ISSN: 0009-2363 *

Also Published As

Publication number Publication date
CA3098164A1 (fr) 2022-05-05

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