CN117903297A - 化学选择性的巯基与烯基或炔基磷酰胺的偶联 - Google Patents

化学选择性的巯基与烯基或炔基磷酰胺的偶联 Download PDF

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Publication number
CN117903297A
CN117903297A CN202311230447.3A CN202311230447A CN117903297A CN 117903297 A CN117903297 A CN 117903297A CN 202311230447 A CN202311230447 A CN 202311230447A CN 117903297 A CN117903297 A CN 117903297A
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China
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alkyl
formula
compound
mmol
phenyl
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CN202311230447.3A
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English (en)
Chinese (zh)
Inventor
H·克里斯蒂安
M·A·卡斯帕
M·格兰仕
T·索尔
D·舒马赫
J·赫尔马-斯梅茨
H·莱昂哈特
A·斯滕格尔
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Forschungsverbund Berlin FVB eV
Ludwig Maximilians Universitaet Muenchen LMU
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Forschungsverbund Berlin FVB eV
Ludwig Maximilians Universitaet Muenchen LMU
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Publication of CN117903297A publication Critical patent/CN117903297A/zh
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    • 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
    • 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
    • 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
    • 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

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  • 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)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (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)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (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)
CN202311230447.3A 2016-09-01 2017-09-01 化学选择性的巯基与烯基或炔基磷酰胺的偶联 Pending CN117903297A (zh)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP16001917.0 2016-09-01
EP16001917 2016-09-01
CN201780053946.6A CN109689112B (zh) 2016-09-01 2017-09-01 化学选择性的巯基与烯基或炔基磷酰胺的偶联
PCT/EP2017/071937 WO2018041985A1 (en) 2016-09-01 2017-09-01 Chemoselective thiol-conjugation with alkene or alkyne-phosphonamidates

Related Parent Applications (1)

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Publication Number Publication Date
CN117903297A true CN117903297A (zh) 2024-04-19

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CN202311230447.3A Pending CN117903297A (zh) 2016-09-01 2017-09-01 化学选择性的巯基与烯基或炔基磷酰胺的偶联
CN201780053946.6A Active CN109689112B (zh) 2016-09-01 2017-09-01 化学选择性的巯基与烯基或炔基磷酰胺的偶联

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Country Status (6)

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US (4) US11161873B2 (https=)
EP (1) EP3506949A1 (https=)
JP (2) JP7217225B2 (https=)
CN (2) CN117903297A (https=)
AU (1) AU2017320913B2 (https=)
WO (1) WO2018041985A1 (https=)

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KR102772724B1 (ko) 2018-03-07 2025-02-24 포슝스베르분드 베를린 에.베. 알켄 또는 알킨-포스포노티올레이트 및 -포스포네이트로의 화학선택적 티올-접합
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
EP4065112A4 (en) * 2019-11-22 2023-12-27 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
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
WO2023083900A1 (en) 2021-11-09 2023-05-19 Tubulis Gmbh Conjugates comprising a phosphorus (v) and a drug moiety
ES3001145T1 (es) 2021-11-09 2025-03-04 Tubulis Gmbh Conjugados que comprenden un fosforo (v) y un resto de camptotecina
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
EP4543893A1 (en) 2022-06-27 2025-04-30 Evexta Bio N-substituted indole derivatives and conjugates for the treatment of cancer
PE20251849A1 (es) 2022-10-18 2025-07-22 Tubulis Gmbh Novedosos anticuerpo anti-tpbg y conjugados-anticuerpo-droga basados en el mismo, metodos terapeuticos y usos de los mismos
JP2025536308A (ja) 2022-10-18 2025-11-05 テューブリス ゲーエムベーハー 新規なＮａＰｉ２ｂ抗体を有する新規な抗体－薬物コンジュゲート、治療的方法、ならびにそれらの使用
IL320284A (en) 2022-10-18 2025-06-01 Tubulis Gmbh Novel anti-napi2b antibodies and antibody-drug-conjugates based thereon, therapeutic methods and uses thereof
EP4637832A1 (en) 2022-12-22 2025-10-29 Tubulis GmbH Conjugates comprising a phosphorus(v) moiety and a drug
AU2024332412A1 (en) 2023-09-01 2026-03-12 Tubulis Gmbh Methods of preparing phosphonamidate compounds
WO2025146313A1 (en) 2024-01-04 2025-07-10 Deutsches Krebsforschungszentrum Phosphinites as reductive disulfide rebridging agents
US12521446B2 (en) 2024-02-27 2026-01-13 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

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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
ES2176484T3 (es) 1995-08-18 2002-12-01 Morphosys Ag Bancos de proteinas/(poli)peptidos.
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
WO2015057063A1 (en) 2013-10-14 2015-04-23 Synaffix B.V. Modified glycoprotein, protein-conjugate and process for the preparation thereof
CA2948082A1 (en) 2014-05-09 2015-11-12 Bayer Pharma Aktiengesellschaft Method for targeted conjugation of peptides and proteins by paired c2 bridging of cysteine amino acids

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AU2017320913B2 (en) 2024-08-15
CA3032251A1 (en) 2018-03-08
US11746124B2 (en) 2023-09-05
JP2023055766A (ja) 2023-04-18
US11161873B2 (en) 2021-11-02
JP7217225B2 (ja) 2023-02-02
US20250090672A1 (en) 2025-03-20
AU2017320913A1 (en) 2019-02-07
WO2018041985A1 (en) 2018-03-08
JP2019532041A (ja) 2019-11-07
CN109689112B (zh) 2023-10-13
CN109689112A (zh) 2019-04-26
EP3506949A1 (en) 2019-07-10
US20230348529A1 (en) 2023-11-02
US12171837B2 (en) 2024-12-24
US20190330264A1 (en) 2019-10-31
US20220106356A1 (en) 2022-04-07

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