IL276981B2 - Chemoselective thiol-conjugation with alkene or alkyne-phosphonothiolates and -phosphonates - Google Patents

Chemoselective thiol-conjugation with alkene or alkyne-phosphonothiolates and -phosphonates

Info

Publication number
IL276981B2
IL276981B2 IL276981A IL27698120A IL276981B2 IL 276981 B2 IL276981 B2 IL 276981B2 IL 276981 A IL276981 A IL 276981A IL 27698120 A IL27698120 A IL 27698120A IL 276981 B2 IL276981 B2 IL 276981B2
Authority
IL
Israel
Prior art keywords
alkyl
peptide
oligonucleotide
formula
protein
Prior art date
Application number
IL276981A
Other languages
English (en)
Hebrew (he)
Other versions
IL276981A (en
IL276981B1 (en
Original Assignee
Forschungsverbund Berlin Ev
Univ Muenchen Ludwig Maximilians
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 Ev, Univ Muenchen Ludwig Maximilians filed Critical Forschungsverbund Berlin Ev
Publication of IL276981A publication Critical patent/IL276981A/en
Publication of IL276981B1 publication Critical patent/IL276981B1/en
Publication of IL276981B2 publication Critical patent/IL276981B2/en

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
    • A61K47/68—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
    • 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)]
    • C07F9/40—Esters thereof
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/76—Albumins
    • 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
    • A61K47/6889—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)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • 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)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4015—Esters of acyclic unsaturated acids
    • 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)]
    • C07F9/40—Esters thereof
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4075—Esters with hydroxyalkyl compounds
    • 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)]
    • C07F9/40—Esters thereof
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4087—Esters with arylalkanols
    • 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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings
    • 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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K16/00—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies
    • C07K16/18—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans
    • C07K16/28—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants
    • C07K16/2863—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants against receptors for growth factors, growth regulators
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K16/00—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies
    • C07K16/18—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans
    • C07K16/28—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants
    • C07K16/2878—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants against the NGF-receptor/TNF-receptor superfamily, e.g. CD27, CD30, CD40, CD95
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K16/00—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies
    • C07K16/42—Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against immunoglobulins
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Immunology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Cell Biology (AREA)
  • Toxicology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Zoology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Saccharide Compounds (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)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
IL276981A 2018-03-07 2019-03-06 Chemoselective thiol-conjugation with alkene or alkyne-phosphonothiolates and -phosphonates IL276981B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP18160384 2018-03-07
PCT/EP2019/055509 WO2019170710A2 (en) 2018-03-07 2019-03-06 Chemoselective thiol-conjugation with alkene or alkyne-phosphonothiolates and -phosphonates

Publications (3)

Publication Number Publication Date
IL276981A IL276981A (en) 2020-10-29
IL276981B1 IL276981B1 (en) 2023-12-01
IL276981B2 true IL276981B2 (en) 2024-04-01

Family

ID=61691626

Family Applications (1)

Application Number Title Priority Date Filing Date
IL276981A IL276981B2 (en) 2018-03-07 2019-03-06 Chemoselective thiol-conjugation with alkene or alkyne-phosphonothiolates and -phosphonates

Country Status (11)

Country Link
US (1) US12453779B2 (https=)
EP (1) EP3762423A2 (https=)
JP (1) JP7429191B2 (https=)
KR (1) KR102772724B1 (https=)
CN (2) CN120098033A (https=)
AU (1) AU2019232602B2 (https=)
BR (1) BR112020018093A2 (https=)
CA (1) CA3092286A1 (https=)
IL (1) IL276981B2 (https=)
SG (1) SG11202008186RA (https=)
WO (1) WO2019170710A2 (https=)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20250269046A1 (en) 2021-02-26 2025-08-28 Forschungsverbund Berlin E.V. Cellular uptake of large biomolecules enabled by cell-surface-reactive cell-penetrating peptide additives
EP4326335A1 (en) 2021-04-23 2024-02-28 Forschungsverbund Berlin E.V. Thiol-conjugation with unsaturated phosphorus(v) compounds
TW202339803A (zh) 2021-11-09 2023-10-16 德商圖布里斯有限公司 包含磷(v)及喜樹鹼分子部分的共軛物
CN118302197A (zh) 2021-11-09 2024-07-05 Tubulis 股份有限公司 包含磷(v)和药物部分的偶联物
JP2025506650A (ja) * 2022-02-17 2025-03-13 レボロ バイオセラピューティクス リミテッド シャペロニン６０．１由来のペプチドを作製する方法
CN119451970A (zh) 2022-06-27 2025-02-14 埃维克斯塔生物公司 用于治疗癌症的n-取代的吲哚衍生物及其偶联物
US20240190958A1 (en) 2022-10-18 2024-06-13 Tubulis Gmbh Novel antibody drug conjugates with novel napi2b antibodies, therapeutic methods and uses thereof
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
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
EP4658320A1 (en) 2024-02-27 2025-12-10 Bristol-Myers Squibb Company Anti-ceacam5 antibody drug conjugates

Citations (3)

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Publication number Priority date Publication date Assignee Title
DE1064512B (de) * 1958-03-26 1959-09-03 Bayer Ag Verfahren zur Herstellung von beta-Alkylmercaptovinylphosphon-saeurethiolestern
US2918488A (en) * 1957-06-24 1959-12-22 Bayer Ag Phosphonic acid esters and a process for their production
DE1136334B (de) * 1960-03-09 1962-09-13 Bayer Ag Verfahren zur Herstellung von Thionothiol- bzw. Thiolphosphon- und -phosphinsaeureestern

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US2535174A (en) 1949-04-07 1950-12-26 Us Rubber Co Mercaptoethanephosphonates
GB1346045A (en) 1955-11-03 1974-02-06 Aviat Minister Of Manufacture of organic phosphorus compounds
CH410942A (de) 1957-06-05 1966-04-15 Bayer Ag Verfahren zur Herstellung von Phosphonsäurethiolestern
US3014943A (en) * 1957-06-24 1961-12-26 Bayer Ag Phosphonic acid esters
US3223754A (en) 1959-12-04 1965-12-14 Bayer Ag Alkyl mercapto alkyl esters of substituted phosphonic acids
US3121662A (en) 1960-03-09 1964-02-18 Bayer Ag (thiono)-thiolphosphonic and-thiolphosphinic acid esters and a process for their production
GB917085A (en) 1960-12-08 1963-01-30 Bayer Ag Phosphonic and thiophosphonic acid esters
US3904710A (en) 1971-08-19 1975-09-09 Exxon Research Engineering Co Pesticidal O,S{40 -dialkyl S-phenylthioalkyl dithiophosphates and preparation thereof
AU725609C (en) 1995-08-18 2002-01-03 Morphosys Ag Protein/(poly)peptide libraries
SI1545613T1 (sl) 2002-07-31 2011-11-30 Seattle Genetics Inc Avristatinski konjugati in njihova uporaba za zdravljenje raka avtoimunske bolezni ali infekcijskebolezni
JP5388856B2 (ja) * 2007-10-18 2014-01-15 片山化学工業株式会社 含リン化合物と含イオウ化合物の触媒
EP2683420B1 (en) 2011-03-11 2018-05-23 W. L. Gore & Associates, Inc. Improvements to immobilised biological entities
WO2015169784A1 (de) 2014-05-09 2015-11-12 Bayer Pharma Aktiengesellschaft Verfahren zur gezielten konjugation von peptiden und proteinen mittels paarweiser c2-verbrückung von cystein-aminosäuren
AU2017320913B2 (en) 2016-09-01 2024-08-15 Forschungsverbund Berlin E.V. Chemoselective thiol-conjugation with alkene or alkyne-phosphonamidates

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2918488A (en) * 1957-06-24 1959-12-22 Bayer Ag Phosphonic acid esters and a process for their production
DE1064512B (de) * 1958-03-26 1959-09-03 Bayer Ag Verfahren zur Herstellung von beta-Alkylmercaptovinylphosphon-saeurethiolestern
DE1136334B (de) * 1960-03-09 1962-09-13 Bayer Ag Verfahren zur Herstellung von Thionothiol- bzw. Thiolphosphon- und -phosphinsaeureestern

Also Published As

Publication number Publication date
CN112088168B (zh) 2025-02-14
AU2019232602B2 (en) 2025-03-27
JP7429191B2 (ja) 2024-02-07
EP3762423A2 (en) 2021-01-13
CN120098033A (zh) 2025-06-06
IL276981A (en) 2020-10-29
KR102772724B1 (ko) 2025-02-24
JP2021516959A (ja) 2021-07-15
US20200390901A1 (en) 2020-12-17
AU2019232602A1 (en) 2020-09-17
SG11202008186RA (en) 2020-09-29
WO2019170710A2 (en) 2019-09-12
CN112088168A (zh) 2020-12-15
IL276981B1 (en) 2023-12-01
CA3092286A1 (en) 2019-09-12
BR112020018093A2 (pt) 2020-12-22
KR20200138750A (ko) 2020-12-10
WO2019170710A3 (en) 2019-10-24
US12453779B2 (en) 2025-10-28
RU2020128767A (ru) 2022-04-07

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