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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    • 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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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
JP2015508638A (ja) * 2012-02-03 2015-03-23 ザ ガバナーズ オブ ザ ユニバーシティ オブ アルバータ ファージディスプレイを用いてペプチド誘導体ライブラリーを定量化するための方法
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
US11072616B2 (en) 2015-11-11 2021-07-27 Universite De Montreal Cyclic peptides targeting alpha-4-beta-7 integrin
ES2884107T3 (es) 2016-11-11 2021-12-10 Zealand Pharma As Multímeros de péptidos cíclicos con diana en la integrina alfa-4 beta-7
US11286281B2 (en) 2017-05-10 2022-03-29 Zealand Pharma A/S Homodetic cyclic peptides targeting alpha-4-beta-7 integrin
SG11202100721SA (en) 2018-07-23 2021-02-25 Univ Alberta Genetically-encoded bicyclic peptide libraries
JP7189368B2 (ja) 2018-10-30 2022-12-13 ギリアード サイエンシーズ， インコーポレイテッド アルファ４ベータ７インテグリンの阻害のための化合物
FI3873884T3 (fi) 2018-10-30 2025-02-24 Gilead Sciences Inc 3-(kinolin-8-yyli)-1,4-dihydropyrido[3,4-d]pyrimidiini-2,4-dionijohdannaisia alfa-4-beta-7-integriinin estäjinä tulehdussairauksien hoidossa
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
EP3873605B1 (en) 2018-10-30 2024-10-23 Gilead Sciences, Inc. Compounds for inhibition of alpha4beta7 integrin
WO2020122182A1 (ja) * 2018-12-12 2020-06-18 中外製薬株式会社 分子内水素結合可能な官能基を有するアミノ酸とそれらのアミノ酸を含むペプチド化合物、およびそれらの製造方法
WO2021030438A1 (en) 2019-08-14 2021-02-18 Gilead Sciences, Inc. Compounds for inhibition of alpha 4 beta 7 integrin
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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US5705481A (en) * 1992-11-06 1998-01-06 Merck Patent Gesellschaft Mit Beschrankter Haftung Cyclopeptides
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CA2702605C (en) * 2006-10-20 2015-03-24 Ryan Hili Unprotected amino aldehydes and applications for same

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

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