DK2408802T3 - Cykliske aminosyremolekyler og fremgangsmåder til fremstilling heraf - Google Patents

Cykliske aminosyremolekyler og fremgangsmåder til fremstilling heraf Download PDF

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Publication number
DK2408802T3
DK2408802T3 DK10753047.9T DK10753047T DK2408802T3 DK 2408802 T3 DK2408802 T3 DK 2408802T3 DK 10753047 T DK10753047 T DK 10753047T DK 2408802 T3 DK2408802 T3 DK 2408802T3
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DK
Denmark
Prior art keywords
amino acid
peptide
cyclic
aryl
nmr
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DK10753047.9T
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English (en)
Inventor
Andrei Yudin
Ryan Hili
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Governing Council Univ Toronto
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Publication of DK2408802T3 publication Critical patent/DK2408802T3/da

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/64—Cyclic peptides containing only normal peptide links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/003—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by transforming the C-terminal amino acid to amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/006—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain amino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
    • C07K5/123—Tripeptides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
    • C07K5/126—Tetrapeptides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Analytical Chemistry (AREA)
  • Peptides Or Proteins (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (13)

1. Fremgangsmåde til dannelse af et cyklisk peptid, hvilken fremgangsmåde omfatter følgende trin: (i) omsætning afen aminendegruppe af et peptid eller en aminosyre med at aziridinaldehyd med følgende struktur:
(ii) omsætning af blandingen i trin (i) med et isocyanid.
2. Fremgangsmåde ifølge krav 1, hvor aziridinaldehydet er aziridinaldehydbisulfit.
3. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 2, hvor isocyanidet er tertiær-butyl isocyanid.
4. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvor fremgangsmåden er en ettrinsfremgangsmåde.
5. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvor omsætningerne finder sted under støkiometriske betingelser.
6. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvor omsætningen foretages med en aminosyre i vand.
7. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvilken fremgangsmåde yderligere omfatter følgende trin: (iii) omsætning af blandingen i trin (ii) med henblik på at åbne aziridinringen.
8. Fremgangsmåde ifølge krav 7, hvor blandingen i trin (ii) omsættes til en thioester.
9. Fremgangsmåde ifølge krav 7, hvorthiolsyren er thiobenzoesyre.
10. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvilken fremgangsmåde yderligere omfatter det trin, at der inkorporeres fluorescerende mærker i det cykliske peptid ved nukleofil ringåbning af aziridingruppen.
11. Forbindelse ifølge nedenstående almene formel:
hvor, R1 og Rn hver især uafhængigt af hinanden er valgt fra en aminosyresidekædegruppe, og R2 er en alkylgruppe.
12. Forbindelse ifølge krav 11, hvor R2 er en tertiær-butylgruppe.
13. Forbindelse med en formel ifølge formel (I) til (VII):
DK10753047.9T 2009-03-16 2010-03-16 Cykliske aminosyremolekyler og fremgangsmåder til fremstilling heraf DK2408802T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US16057109P 2009-03-16 2009-03-16
PCT/CA2010/000408 WO2010105363A1 (en) 2009-03-16 2010-03-16 Cyclic amino acid molecules and methods of preparing the same

Publications (1)

Publication Number Publication Date
DK2408802T3 true DK2408802T3 (da) 2017-08-28

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Family Applications (1)

Application Number Title Priority Date Filing Date
DK10753047.9T DK2408802T3 (da) 2009-03-16 2010-03-16 Cykliske aminosyremolekyler og fremgangsmåder til fremstilling heraf

Country Status (10)

Country Link
US (2) US9260479B2 (da)
EP (1) EP2408802B1 (da)
JP (1) JP5866277B2 (da)
CN (1) CN102498124B (da)
AU (1) AU2010225426B2 (da)
CA (1) CA2756804C (da)
DK (1) DK2408802T3 (da)
ES (1) ES2634431T3 (da)
PT (1) PT2408802T (da)
WO (1) WO2010105363A1 (da)

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WO2012109735A1 (en) * 2011-02-17 2012-08-23 The Governing Council Of The University Of Toronto Methods of preparing cyclic amino acid molecules using arylboronic or arylborinic acid catalysts
CA2861137C (en) * 2012-02-03 2022-03-22 The Governors Of The University Of Alberta Method of quantifying peptide-derivative libraries using phage display
US20170320908A1 (en) * 2014-11-19 2017-11-09 Encycle Therapeutics Solid phase synthesis of cyclic amino acid molecules
CN105087709B (zh) * 2015-08-20 2019-09-17 江苏省原子医学研究所 一种酶催化多组分反应合成环肽的方法
EP3387004B1 (en) 2015-11-11 2021-10-06 Zealand Pharma A/S Cyclic peptides targeting alpha4 beta7 integrin
US11111273B2 (en) 2016-11-11 2021-09-07 Zealand Pharma A/S Cyclic peptides multimers targeting alpha-4-beta-7 integrin
EP3577258B1 (en) 2017-01-31 2024-11-27 48Hour Discovery Inc. Display of molecules on silently genetically encoded nanoscale carriers for determining synergistic molecular interactions
CA3062385A1 (en) 2017-05-10 2018-11-15 Encycle Therapeutics, Inc. Homodetic cyclic peptides targeting a4s7 1ntegrin
SG11202100721SA (en) 2018-07-23 2021-02-25 Univ Alberta Genetically-encoded bicyclic peptide libraries
KR102630416B1 (ko) 2018-10-30 2024-02-01 길리애드 사이언시즈, 인코포레이티드 알파4베타7 인테그린 억제제로서의 퀴놀린 유도체
AU2019373242B2 (en) 2018-10-30 2023-07-13 Gilead Sciences, Inc. Compounds for inhibition of alpha 4 beta 7 integrin
ES3013256T3 (en) 2018-10-30 2025-04-11 Gilead Sciences Inc Imidazo[1,2-a]pyridine derivatives as alpha4beta7 integrin inhibitors for the treatment of inflammatory diseases
US11179383B2 (en) 2018-10-30 2021-11-23 Gilead Sciences, Inc. Compounds for inhibition of α4β7 integrin
CN118184532A (zh) * 2018-12-12 2024-06-14 中外制药株式会社 具有能形成分子内氢键的官能团的氨基酸、包含该氨基酸的肽化合物、及其制备方法
CN114222730B (zh) 2019-08-14 2024-09-10 吉利德科学公司 用于抑制α4β7整合素的化合物
CN118440136B (zh) * 2024-05-08 2025-02-18 武昌理工学院 一种蛋白质赖氨酸选择性修饰的方法及其应用

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AU638264B2 (en) * 1989-08-10 1993-06-24 Aventis Inc. Cyclic neurokinin a antagonists
US5705481A (en) * 1992-11-06 1998-01-06 Merck Patent Gesellschaft Mit Beschrankter Haftung Cyclopeptides
AU681119B2 (en) * 1993-05-17 1997-08-21 Fujisawa Pharmaceutical Co., Ltd. New polypeptide compound and a process for preparation thereof
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US8143375B2 (en) * 2006-10-20 2012-03-27 The Governing Council Of The University Of Toronto Aziridine aldehydes, aziridine-conjugated amino derivatives, aziridine-conjugated biomolecules and processes for their preparation

Also Published As

Publication number Publication date
US9260479B2 (en) 2016-02-16
US10385099B2 (en) 2019-08-20
WO2010105363A1 (en) 2010-09-23
CA2756804A1 (en) 2010-09-23
EP2408802B1 (en) 2017-05-03
CA2756804C (en) 2020-12-22
EP2408802A1 (en) 2012-01-25
AU2010225426A8 (en) 2014-04-03
US20160222062A1 (en) 2016-08-04
JP2012520330A (ja) 2012-09-06
ES2634431T3 (es) 2017-09-27
CN102498124A (zh) 2012-06-13
JP5866277B2 (ja) 2016-02-17
EP2408802A4 (en) 2013-04-17
HK1172036A1 (en) 2013-04-12
AU2010225426A1 (en) 2011-10-13
CN102498124B (zh) 2015-05-13
US20120065366A1 (en) 2012-03-15
AU2010225426B2 (en) 2015-09-03
PT2408802T (pt) 2017-08-03

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