CA3032251A1 - Chemoselective thiol-conjugation with alkene or alkyne-phosphonamidates - Google Patents

Chemoselective thiol-conjugation with alkene or alkyne-phosphonamidates Download PDF

Info

Publication number
CA3032251A1
CA3032251A1 CA3032251A CA3032251A CA3032251A1 CA 3032251 A1 CA3032251 A1 CA 3032251A1 CA 3032251 A CA3032251 A CA 3032251A CA 3032251 A CA3032251 A CA 3032251A CA 3032251 A1 CA3032251 A1 CA 3032251A1
Authority
CA
Canada
Prior art keywords
alkyl
formula
compound
phenyl
mmol
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.)
Pending
Application number
CA3032251A
Other languages
English (en)
French (fr)
Inventor
Hackenberger CHRISTIAN
Marc Andre Kasper
Maria GLANZ
Tom SAUER
Dominik SCHUMACHER
Jonas HELMA-SMETS
Heinrich Leonhardt
Andreas STENGL
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.)
Forschungsverbund Berlin FVB eV
Ludwig Maximilians Universitaet Muenchen LMU
Original Assignee
Forschungsverbund Berlin FVB eV
Ludwig Maximilians Universitaet Muenchen LMU
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 Forschungsverbund Berlin FVB eV, Ludwig Maximilians Universitaet Muenchen LMU filed Critical Forschungsverbund Berlin FVB eV
Publication of CA3032251A1 publication Critical patent/CA3032251A1/en
Pending legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
    • A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/07—Tetrapeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/549—Sugars, nucleosides, nucleotides or nucleic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
    • A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
    • A61K47/68031—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug being an auristatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6835—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site
    • A61K47/6849—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site the antibody targeting a receptor, a cell surface antigen or a cell surface determinant
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6835—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site
    • A61K47/6851—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site the antibody targeting a determinant of a tumour cell
    • A61K47/6855—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site the antibody targeting a determinant of a tumour cell the tumour determinant being from breast cancer cell
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6889—Conjugates wherein the antibody being the modifying agent and wherein the linker, binder or spacer confers particular properties to the conjugates, e.g. peptidic enzyme-labile linkers or acid-labile linkers, providing for an acid-labile immuno conjugate wherein the drug may be released from its antibody conjugated part in an acidic, e.g. tumoural or environment
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/44—Amides thereof
    • C07F9/4461—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/44—Amides thereof
    • C07F9/4461—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4473—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic of cycloaliphatic amines
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/44—Amides thereof
    • C07F9/4461—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/448—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic of aralkylamines
    • 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
    • C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
    • C07K1/1072—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups
    • C07K1/1077—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups by covalent attachment of residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/82—Translation products from oncogenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0215—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biochemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Immunology (AREA)
  • Cell Biology (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Oncology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA3032251A 2016-09-01 2017-09-01 Chemoselective thiol-conjugation with alkene or alkyne-phosphonamidates Pending CA3032251A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP16001917.0 2016-09-01
EP16001917 2016-09-01
PCT/EP2017/071937 WO2018041985A1 (en) 2016-09-01 2017-09-01 Chemoselective thiol-conjugation with alkene or alkyne-phosphonamidates

Publications (1)

Publication Number Publication Date
CA3032251A1 true CA3032251A1 (en) 2018-03-08

Family

ID=56888890

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3032251A Pending CA3032251A1 (en) 2016-09-01 2017-09-01 Chemoselective thiol-conjugation with alkene or alkyne-phosphonamidates

Country Status (7)

Country Link
US (4) US11161873B2 (enExample)
EP (1) EP3506949A1 (enExample)
JP (2) JP7217225B2 (enExample)
CN (2) CN117903297A (enExample)
AU (1) AU2017320913B2 (enExample)
CA (1) CA3032251A1 (enExample)
WO (1) WO2018041985A1 (enExample)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019170710A2 (en) * 2018-03-07 2019-09-12 Forschungsverbund Berlin E.V. Chemoselective thiol-conjugation with alkene or alkyne-phosphonothiolates and -phosphonates
CN109666044B (zh) * 2018-07-04 2021-03-05 浙江大学 基于[2.2]对环芳烷骨架的有机磷化合物及其中间体和制备方法与用途
WO2021102359A2 (en) * 2019-11-22 2021-05-27 The Regents Of The University Of California Taspase1 inhibitors and uses thereof
US20230250461A1 (en) * 2020-06-26 2023-08-10 Yale University Compositions and Methods for Selective Detection and/or Inhibition of Bacterial Pathogens in Microbial Communities
EP4297794A2 (en) 2021-02-26 2024-01-03 Forschungsverbund Berlin E.V. Cellular uptake of large biomolecules enabled by cell-surface-reactive cell-penetrating peptide additives
US20240350655A1 (en) 2021-04-23 2024-10-24 Forschungsverbund Berlin E.V. Thiol-conjugation with unsaturated phosphorus(v) compounds
PE20242107A1 (es) 2021-11-09 2024-10-28 Tubulis Gmbh Conjugados que comprenden fosforo (v) y una fraccion molecular de droga
DE22817180T1 (de) 2021-11-09 2024-12-12 Tubulis Gmbh Konjugate mit einem phosphor (v) und einem camptothecinteil
WO2023105087A1 (en) 2021-12-10 2023-06-15 Tubulis Gmbh Novel flt3 antibodies and antibody-drug-conjugates based thereon, therapeutic methods and uses thereof in combination with tyrosine kinase inhibitors
JP2025521735A (ja) 2022-06-27 2025-07-10 イヴクスタ・バイオ がんの処置のためのｎ－置換インドール誘導体及びコンジュゲート
WO2024083953A1 (en) 2022-10-18 2024-04-25 Tubulis Gmbh Novel anti-tpbg antibody and antibody-drug-conjugates based thereon, therapeutic methods and uses thereof
PE20251880A1 (es) 2022-10-18 2025-07-22 Tubulis Gmbh Novedosos anticuerpos anti-napi2b y conjugados-anticuerpo-droga basados en ellos, metodos terapeuticos y usos de los mismos
AU2023364103A1 (en) 2022-10-18 2025-05-29 Tubulis Gmbh Novel antibody drug conjugates with novel napi2b antibodies, therapeutic methods and uses thereof
WO2024133845A1 (en) 2022-12-22 2024-06-27 Tubulis Gmbh Conjugates comprising a phosphorus(v) moiety and a drug
WO2025046090A1 (en) 2023-09-01 2025-03-06 Tubulis Gmbh Methods of preparing phosphonamidate compounds
WO2025146313A1 (en) 2024-01-04 2025-07-10 Deutsches Krebsforschungszentrum Phosphinites as reductive disulfide rebridging agents
EP4658320A1 (en) 2024-02-27 2025-12-10 Bristol-Myers Squibb Company Anti-ceacam5 antibody drug conjugates
CN119391070A (zh) * 2024-11-28 2025-02-07 宁波卡倍亿新材料科技有限公司 一种新能源汽车耐高温阻燃电缆料及其制备方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2535174A (en) 1949-04-07 1950-12-26 Us Rubber Co Mercaptoethanephosphonates
DE2024250A1 (de) * 1970-05-19 1971-12-02 Farbwerke Hoechst AG, vorm. Meister Lucius & Brüning, 6000 Frankfurt Antimikrobielle grenzflächenaktive Mittel
CA2229043C (en) 1995-08-18 2016-06-07 Morphosys Gesellschaft Fur Proteinoptimierung Mbh Protein/(poly)peptide libraries
US9023834B2 (en) 2008-11-13 2015-05-05 Taigen Biotechnology Co., Ltd. Lyophilization formulation
CN102058547A (zh) * 2009-11-12 2011-05-18 太景生物科技股份有限公司 冻干制剂
EP3564259A3 (en) * 2012-11-09 2020-02-12 Innate Pharma Recognition tags for tgase-mediated conjugation
JP2016538877A (ja) 2013-10-14 2016-12-15 シンアフィックス ビー．ブイ． 修飾糖タンパク質、タンパク質コンジュゲート及びそれらの調製方法
EP3140321A1 (de) 2014-05-09 2017-03-15 Bayer Pharma Aktiengesellschaft Verfahren zur gezielten konjugation von peptiden und proteinen mittels paarweiser c2-verbrückung von cystein-aminosäuren

Also Published As

Publication number Publication date
CN109689112A (zh) 2019-04-26
JP7217225B2 (ja) 2023-02-02
US12171837B2 (en) 2024-12-24
US20220106356A1 (en) 2022-04-07
US11746124B2 (en) 2023-09-05
US11161873B2 (en) 2021-11-02
CN109689112B (zh) 2023-10-13
US20250090672A1 (en) 2025-03-20
EP3506949A1 (en) 2019-07-10
US20230348529A1 (en) 2023-11-02
WO2018041985A1 (en) 2018-03-08
AU2017320913B2 (en) 2024-08-15
AU2017320913A1 (en) 2019-02-07
US20190330264A1 (en) 2019-10-31
JP2023055766A (ja) 2023-04-18
CN117903297A (zh) 2024-04-19
JP2019532041A (ja) 2019-11-07

Similar Documents

Publication Publication Date Title
US12171837B2 (en) Chemoselective thiol-conjugation with alkene or alkyne-phosphonamidates
AU2019232602B2 (en) Chemoselective thiol-conjugation with alkene or alkyne-phosphonothiolates and -phosphonates
ES2910699T3 (es) Inmunoglobulinas conjugadas con lisina C-terminal
ES2905842T3 (es) Derivados de 6-amino-7,9-dihidro-8h-purin-8-ona como agonistas del receptor tipo Toll 7 (TLR7) como inmunoestimulantes
US20240350655A1 (en) Thiol-conjugation with unsaturated phosphorus(v) compounds
Roy et al. Prodrugs of nucleoside 5'-monophosphate analogues: Overview of the recent literature concerning their synthesis and applications
US11293060B2 (en) Method for labeling of aldehyde containing target molecules
Peyrottes et al. S-acyl-2-thioethyl aryl phosphotriester derivatives of AZT: Synthesis, antiviral activity, and stability study
Dirin et al. Fragment-based solid-phase assembly of oligonucleotide conjugates with peptide and polyethylene glycol ligands
RU2825582C2 (ru) Хемоселективная тиол-конъюгация с алкен- или алкин-фосфонотиолатами и -фосфонатами
RU2825582C9 (ru) Хемоселективная тиол-конъюгация с алкен- или алкин-фосфонотиолатами и -фосфонатами
Palte Characterization and Exploitation of the Glycocalyx for Drug Delivery

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20220830

EEER Examination request

Effective date: 20220830

EEER Examination request

Effective date: 20220830

EEER Examination request

Effective date: 20220830