WO2024258613A3 - Tetrachlorovancomycin and derivatives - Google Patents

Tetrachlorovancomycin and derivatives Download PDF

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Publication number
WO2024258613A3
WO2024258613A3 PCT/US2024/031453 US2024031453W WO2024258613A3 WO 2024258613 A3 WO2024258613 A3 WO 2024258613A3 US 2024031453 W US2024031453 W US 2024031453W WO 2024258613 A3 WO2024258613 A3 WO 2024258613A3
Authority
WO
WIPO (PCT)
Prior art keywords
compound
new class
tetrachlorovancomycin
derivatives
tetrachlorovancomcyin
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.)
Ceased
Application number
PCT/US2024/031453
Other languages
French (fr)
Other versions
WO2024258613A2 (en
WO2024258613A9 (en
Inventor
Dale L. Boger
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.)
Scripps Research Institute
Original Assignee
Scripps Research Institute
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 Scripps Research Institute filed Critical Scripps Research Institute
Publication of WO2024258613A2 publication Critical patent/WO2024258613A2/en
Publication of WO2024258613A3 publication Critical patent/WO2024258613A3/en
Publication of WO2024258613A9 publication Critical patent/WO2024258613A9/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
    • C07K9/006—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure
    • C07K9/008—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure directly attached to a hetero atom of the saccharide radical, e.g. actaplanin, avoparcin, ristomycin, vancomycin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

A total synthesis of a new class of vancomycin analogues of reduced synthetic complexity was developed. The synthesis, achieved by the addition of two aryl chloride substituents to provide tetrachlorovancomcyin aglycon (Compound II), tetrachlorovancomcyin (Compound I ), and their derivatives, permitted a streamlined total synthesis of the new class of glycopeptide antibiotics by removing atropisomer stereochemical control and enabled the simultaneous and further activated SNAr macrocyclizations that establish the tricyclic skeleton of Compound I. In addition to the antimicrobial evaluation of tetrachlorovancomycin (Compound I), the preparation of key binding pocket and peripherally-modi fied derivatives, which overcome vancomycin resistance and introduce independent and synergistic mechanisms of action, revealed their exceptional antimicrobial potency and provide the foundation for use of this new class of synthetic glycopeptide analogues. Also disclosed are a pharmaceutical composition containing bactericidal amount of tetrachlorovancomycin, a derivative thereof or a salt of either dissolved or dispersed in a pharmaceutically acceptable diluent.
PCT/US2024/031453 2023-06-16 2024-05-29 Tetrachlorovancomycin and derivatives Ceased WO2024258613A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202363521400P 2023-06-16 2023-06-16
US63/521,400 2023-06-16

Publications (3)

Publication Number Publication Date
WO2024258613A2 WO2024258613A2 (en) 2024-12-19
WO2024258613A3 true WO2024258613A3 (en) 2025-01-23
WO2024258613A9 WO2024258613A9 (en) 2025-05-30

Family

ID=93852816

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2024/031453 Ceased WO2024258613A2 (en) 2023-06-16 2024-05-29 Tetrachlorovancomycin and derivatives

Country Status (1)

Country Link
WO (1) WO2024258613A2 (en)

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
AKINORI OKANO, ISLEY NICHOLAS A., BOGER DALE L.: "Total Syntheses of Vancomycin-Related Glycopeptide Antibiotics and Key Analogues", CHEMICAL REVIEWS, vol. 117, no. 18, 24 April 2017 (2017-04-24), US , pages 11952 - 11993, XP055694659, ISSN: 0009-2665, DOI: 10.1021/acs.chemrev.6b00820 *
BRENDAN M. CROWLEY, DALE L. BOGER: "Total Synthesis and Evaluation of [psi[ CH 2NH]Tpg4]Vancomycin Aglycon: Reengineering Vancomycin for Dual D-Ala-D-Ala and Dala- D-Lac Binding", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 128, no. 9, 1 March 2006 (2006-03-01), pages 2885 - 2892, XP055143848, ISSN: 00027863, DOI: 10.1021/ja0572912 *
JAMES M. KRAUS, HARI BABU TATIPAKA, SARAH A. MCGUFFIN, NAVEEN KUMAR CHENNAMANENI, MANDANA KARIMI, JENIFER ARIF, CHRISTOPHE L. M. J: "Second Generation Analogues of the Cancer Drug Clinical Candidate Tipifarnib for Anti-Chagas Disease Drug Discovery", JOURNAL OF MEDICINAL CHEMISTRY, vol. 53, no. 10, 27 May 2010 (2010-05-27), pages 3887 - 3898, XP055056989, ISSN: 00222623, DOI: 10.1021/jm9013136 *
NAGARAJAN RAMAKRISHNAN: "Antibacterial Activities and Modes of Action of Vancomycin and Related Glycopeptides", ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, vol. 35, no. 4, 1 April 1991 (1991-04-01), pages 605 - 609, XP093268433 *

Also Published As

Publication number Publication date
WO2024258613A2 (en) 2024-12-19
WO2024258613A9 (en) 2025-05-30

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