JP6739333B2 - 部位特異的化学酵素的タンパク質修飾 - Google Patents

部位特異的化学酵素的タンパク質修飾 Download PDF

Info

Publication number
JP6739333B2
JP6739333B2 JP2016525817A JP2016525817A JP6739333B2 JP 6739333 B2 JP6739333 B2 JP 6739333B2 JP 2016525817 A JP2016525817 A JP 2016525817A JP 2016525817 A JP2016525817 A JP 2016525817A JP 6739333 B2 JP6739333 B2 JP 6739333B2
Authority
JP
Japan
Prior art keywords
protein
acid
mmol
polysaccharide
compound
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.)
Active
Application number
JP2016525817A
Other languages
English (en)
Japanese (ja)
Other versions
JP2016526574A (ja
JP2016526574A5 (cg-RX-API-DMAC7.html
Inventor
ウセラ，エイミー
ロビンソン，ザカリー
コッブ，ジェニファー
Original Assignee
ノバルティス アーゲー
ノバルティス アーゲー
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 ノバルティス アーゲー, ノバルティス アーゲー filed Critical ノバルティス アーゲー
Publication of JP2016526574A publication Critical patent/JP2016526574A/ja
Publication of JP2016526574A5 publication Critical patent/JP2016526574A5/ja
Application granted granted Critical
Publication of JP6739333B2 publication Critical patent/JP6739333B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
    • 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
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
    • C07K5/101—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
    • 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
    • A61K47/6415—Toxins or lectins, e.g. clostridial toxins or Pseudomonas exotoxins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/0002—General or multifunctional contrast agents, e.g. chelated agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D229/00—Heterocyclic compounds containing rings of less than five members having two nitrogen atoms as the only ring hetero atoms
    • C07D229/02—Heterocyclic compounds containing rings of less than five members having two nitrogen atoms as the only ring hetero atoms containing three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/08—Six-membered rings
    • 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
    • C07K1/1075—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 amino acids or peptide residues
    • 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
    • C07K1/13—Labelling of peptides
    • 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
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06043—Leu-amino acid
    • 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
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/02—Linear peptides containing at least one abnormal peptide link
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • 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
    • A61K38/05—Dipeptides
    • 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
    • A61K38/06—Tripeptides
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/24—All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Analytical Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Immunology (AREA)
  • Toxicology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Gastroenterology & Hepatology (AREA)
JP2016525817A 2013-07-11 2014-07-11 部位特異的化学酵素的タンパク質修飾 Active JP6739333B2 (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201361845273P 2013-07-11 2013-07-11
US61/845,273 2013-07-11
US201462016044P 2014-06-23 2014-06-23
US62/016,044 2014-06-23
PCT/US2014/046409 WO2015006728A2 (en) 2013-07-11 2014-07-11 Site-specific chemoenzymatic protein modifications

Publications (3)

Publication Number Publication Date
JP2016526574A JP2016526574A (ja) 2016-09-05
JP2016526574A5 JP2016526574A5 (cg-RX-API-DMAC7.html) 2017-08-24
JP6739333B2 true JP6739333B2 (ja) 2020-08-12

Family

ID=51298955

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2016525817A Active JP6739333B2 (ja) 2013-07-11 2014-07-11 部位特異的化学酵素的タンパク質修飾

Country Status (12)

Country Link
US (4) US9359400B2 (cg-RX-API-DMAC7.html)
EP (2) EP3019515B1 (cg-RX-API-DMAC7.html)
JP (1) JP6739333B2 (cg-RX-API-DMAC7.html)
KR (1) KR20160040556A (cg-RX-API-DMAC7.html)
CN (1) CN105593238B (cg-RX-API-DMAC7.html)
AU (1) AU2014286990A1 (cg-RX-API-DMAC7.html)
BR (1) BR112016000585A2 (cg-RX-API-DMAC7.html)
CA (1) CA2918076A1 (cg-RX-API-DMAC7.html)
EA (1) EA201690205A1 (cg-RX-API-DMAC7.html)
ES (1) ES2756526T3 (cg-RX-API-DMAC7.html)
MX (1) MX2016000393A (cg-RX-API-DMAC7.html)
WO (1) WO2015006728A2 (cg-RX-API-DMAC7.html)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9359400B2 (en) 2013-07-11 2016-06-07 Novartis Ag Site-specific chemoenzymatic protein modifications
US10588980B2 (en) * 2014-06-23 2020-03-17 Novartis Ag Fatty acids and their use in conjugation to biomolecules
MY192987A (en) * 2015-12-18 2022-09-20 Eisai R&D Man Co Ltd C-terminal lysine conjugated immunoglobulins
US11058757B2 (en) 2016-03-31 2021-07-13 Pogona, LLC Saccharide-polypeptide conjugate compositions and methods of use thereof
PE20190340A1 (es) 2016-06-10 2019-03-07 Eisai Randd Man Co Ltd Inmunglobulinas conjugadas con lisina
WO2018045286A1 (en) 2016-09-02 2018-03-08 Sanofi Pasteur, Inc. Neisseria meningitidis vaccine
US11951165B2 (en) 2016-12-30 2024-04-09 Vaxcyte, Inc. Conjugated vaccine carrier proteins
KR20190103256A (ko) 2016-12-30 2019-09-04 수트로박스, 인코포레이티드 비자연 아미노산을 갖는 폴리펩타이드-항원 접합체
WO2019070994A1 (en) 2017-10-04 2019-04-11 Liffey Biotech Limited SACCHARIDE-POLYPEPTIDE CONJUGATE COMPOSITIONS AND METHODS OF USE
AU2020212055B2 (en) * 2019-01-25 2025-10-02 Avedro, Inc. Bis(diazirine) derivatives as photo-crossslinker for treating corneal ectatic disorders
JP2025520445A (ja) * 2022-06-16 2025-07-03 ザ ジェネラル ホスピタル コーポレイション 細胞イメージング用のビシクロノニン試薬
WO2025020905A1 (zh) * 2023-07-26 2025-01-30 菲鹏生物股份有限公司 抗体和抗体缀合物及其用途

Family Cites Families (56)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4179337A (en) 1973-07-20 1979-12-18 Davis Frank F Non-immunogenic polypeptides
JPH0665280B2 (ja) 1987-03-04 1994-08-24 味の素株式会社 タンパクゲル化剤及びそれを用いるタンパクのゲル化方法
DE4022267C2 (de) * 1990-07-12 1994-09-15 Degussa N-Acyldipeptide und deren Verwendung
JP2849773B2 (ja) 1990-08-27 1999-01-27 天野製薬株式会社 ストレプトミセス属由来のトランスグルタミナーゼの製造法
US5153312A (en) 1990-09-28 1992-10-06 American Cyanamid Company Oligosaccharide conjugate vaccines
US5425946A (en) 1992-08-31 1995-06-20 North American Vaccine, Inc. Vaccines against group C Neisseria meningitidis
ES2171418T3 (es) 1992-08-31 2002-09-16 Baxter Healthcare Sa Vacunas contra neisseria meningitidis del grupo c.
US5508191A (en) 1993-07-05 1996-04-16 Takeda Chemical Industries, Ltd. Mutant strains of agrobacterium for producing β-1,3-glucan
ES2267103T3 (es) 1994-08-26 2007-03-01 Novozymes A/S Transglutaminasas microbianas, su produccion y uso.
EP0785276A4 (en) 1994-09-29 2002-01-09 Ajinomoto Kk MODIFICATION OF A PEPTIDE AND A PROTEIN
NZ298746A (en) 1995-01-19 1998-07-28 Novo Nordisk As Transglutaminases from oomcyetes
JP3669390B2 (ja) 1995-02-09 2005-07-06 味の素株式会社 バチルス属細菌由来のトランスグルタミナーゼ
US6284884B1 (en) 1995-06-07 2001-09-04 North American Vaccine, Inc. Antigenic group B streptococcus type II and type III polysaccharide fragments having a 2,5-anhydro-D-mannose terminal structure and conjugate vaccine thereof
EP0815833B1 (en) * 1996-06-24 2003-04-09 Givaudan SA Malodour preventing agents
WO1998013381A1 (fr) 1996-09-26 1998-04-02 Ajinomoto Co., Inc. Proteines modifiees physiologiquement actives et compositions medicamenteuses les contenant
US6299881B1 (en) 1997-03-24 2001-10-09 Henry M. Jackson Foundation For The Advancement Of Military Medicine Uronium salts for activating hydroxyls, carboxyls, and polysaccharides, and conjugate vaccines, immunogens, and other useful immunological reagents produced using uronium salts
JP3981525B2 (ja) 1998-01-20 2007-09-26 ハワード・グリーン 組織への物質のトランスグルタミナーゼ連結
US6919076B1 (en) 1998-01-20 2005-07-19 Pericor Science, Inc. Conjugates of agents and transglutaminase substrate linking molecules
US6958148B1 (en) 1998-01-20 2005-10-25 Pericor Science, Inc. Linkage of agents to body tissue using microparticles and transglutaminase
US6936258B1 (en) 1999-03-19 2005-08-30 Nabi Biopharmaceuticals Staphylococcus antigen and vaccine
EP2332581B1 (en) 2001-01-23 2015-07-01 Sanofi Pasteur Inc. Tri- or tetravalent meningococcal polysaccharide-CRM197 conjugate vaccine
US7605175B2 (en) 2001-03-02 2009-10-20 Gpc Biotech Ag Inhibitors of cyclin-dependent kinases, compositions and uses related thereto
GB0115176D0 (en) 2001-06-20 2001-08-15 Chiron Spa Capular polysaccharide solubilisation and combination vaccines
JP2003199569A (ja) 2001-12-17 2003-07-15 Food Industry Research & Development Inst ストレプトベルティシリウム・ラダカヌムのトランスグルタミナーゼ遺伝子及び該遺伝子によってコードされるトランスグルタミナーゼ
WO2003080678A1 (en) 2002-03-26 2003-10-02 Chiron Srl Modified saccharides having improved stability in water
GB0211118D0 (en) 2002-05-15 2002-06-26 Polonelli Luciano Vaccines
GB0323103D0 (en) 2003-10-02 2003-11-05 Chiron Srl De-acetylated saccharides
WO2006028129A1 (ja) 2004-09-10 2006-03-16 Toray Industries, Inc. 医薬品製剤
AU2005302269B2 (en) 2004-11-01 2011-05-19 The Brigham And Women's Hospital, Inc. Modified streptococcal polysaccharides and uses thereof
GB0502096D0 (en) 2005-02-01 2005-03-09 Chiron Srl Purification of streptococcal capsular polysaccharide
TW200716179A (en) * 2005-06-15 2007-05-01 Novo Nordisk As Transglutaminase mediated conjugation of growth hormone
GB0700562D0 (en) 2007-01-11 2007-02-21 Novartis Vaccines & Diagnostic Modified Saccharides
CN101809032A (zh) * 2007-08-24 2010-08-18 诺沃-诺迪斯克有限公司 用于选择性修饰蛋白质的方法
US8426179B2 (en) * 2007-08-30 2013-04-23 Northwestern University Synthetic peptide and peptide conjugates and related tissue coupling methods via transglutaminase enzyme
DE102007044296A1 (de) * 2007-09-17 2009-03-19 Hans-Lothar Prof. Dr. Fuchsbauer Strukturmodulator von Proteinen
US8137925B2 (en) * 2007-11-09 2012-03-20 Massachusetts Institute Of Technology Methods and compositions for protein labeling using lipoic acid ligases
GB0818453D0 (en) 2008-10-08 2008-11-12 Novartis Ag Fermentation processes for cultivating streptococci and purification processes for obtaining cps therefrom
JPWO2010002042A1 (ja) 2008-07-04 2011-12-22 国立大学法人九州大学 タンパク質ラベル化用酵素基質
CN102333788A (zh) * 2009-02-19 2012-01-25 诺沃—诺迪斯克有限公司 因子viii的修饰
FR2947269B1 (fr) 2009-06-29 2013-01-18 Sanofi Aventis Nouveaux composes anticancereux
WO2011002852A2 (en) 2009-06-30 2011-01-06 The Regents Of The University Of Michigan Pro-drug complexes and related methods of use
US20110020837A1 (en) 2009-07-07 2011-01-27 Universiteit Utrecht Holding B.V. Method for isolating or identifying a target protein interacting with a lipid in a cell
WO2011079315A1 (en) 2009-12-23 2011-06-30 The Scripps Research Institute Tyrosine bioconjugation through aqueous ene-like reactions
ES2527536T7 (es) 2010-04-27 2016-03-08 Synaffix B.V. Compuestos de ciclooctina fusionada y su uso en reacciones clic sin metales
WO2012006475A1 (en) 2010-07-07 2012-01-12 Ardelyx, Inc. Compounds and methods for inhibiting phosphate transport
EP2590989A2 (en) 2010-07-09 2013-05-15 Universite de Bretagne Occidentale Modular construction of lipophospholipids
EP2633062B1 (en) 2010-10-29 2017-12-27 Life Technologies Corporation Biotin derivatives
EP2635310A2 (en) 2010-11-05 2013-09-11 Rinat Neuroscience Corp. Engineered polypeptide conjugates and methods for making thereof using transglutaminase
EP2649099A4 (en) 2010-12-07 2016-10-19 Univ Yale SMALL MOLECULAR HYDROPHOBIC LABELING OF FUSION PROTEINS AND INDUCED REMOVAL FROM THIS
CA2814953A1 (en) 2010-12-13 2012-06-21 Immunomedics, Inc. Methods and compositions for improved f-18 labeling of proteins, peptides and other molecules
WO2012142659A1 (en) 2011-04-19 2012-10-26 Baker Idi Heart And Diabetes Institute Holdings Limited Site-selective modification of proteins
FR2981352B1 (fr) 2011-10-17 2015-07-03 Centre Nat Rech Scient Procede de synthese de proteines
JP2015505824A (ja) 2011-12-01 2015-02-26 アンジオケム インコーポレーテッド 標的化リソソーム酵素化合物
JP5509440B2 (ja) * 2012-06-22 2014-06-04 国立大学法人九州大学 タンパク質−核酸複合体の製造方法および標的物の検出方法
CN105517577A (zh) * 2013-06-21 2016-04-20 先天制药公司 多肽的酶促偶联
US9359400B2 (en) * 2013-07-11 2016-06-07 Novartis Ag Site-specific chemoenzymatic protein modifications

Also Published As

Publication number Publication date
CA2918076A1 (en) 2015-01-15
US10975120B2 (en) 2021-04-13
CN105593238A (zh) 2016-05-18
WO2015006728A2 (en) 2015-01-15
CN105593238B (zh) 2020-09-08
EP3019515B1 (en) 2019-08-21
EA201690205A1 (ru) 2016-12-30
US20220089639A1 (en) 2022-03-24
US20150017192A1 (en) 2015-01-15
JP2016526574A (ja) 2016-09-05
MX2016000393A (es) 2016-10-26
EP3019515A2 (en) 2016-05-18
WO2015006728A3 (en) 2015-03-12
AU2014286990A1 (en) 2016-02-11
ES2756526T3 (es) 2020-04-27
US20160237116A1 (en) 2016-08-18
US20190300570A1 (en) 2019-10-03
BR112016000585A2 (pt) 2018-03-20
EP3613755A1 (en) 2020-02-26
US9359400B2 (en) 2016-06-07
KR20160040556A (ko) 2016-04-14

Similar Documents

Publication Publication Date Title
JP6739333B2 (ja) 部位特異的化学酵素的タンパク質修飾
CN110366428B (zh) 具有非天然氨基酸的多肽-抗原缀合物
JP4097691B2 (ja) Ｃ群髄膜炎菌に対するワクチン
EP0959905B1 (en) Polysaccharide-peptide-conjugates
JP6170932B2 (ja) ｓｐｒ００９６抗原およびｓｐｒ２０２１抗原を含むキャリア分子
US7700551B2 (en) Hydrolysable polymeric FMOC-linker
JP7439174B2 (ja) 免疫原性コンジュゲート及びその使用
CN108064174A (zh) 抗原的载体分子
BR112020018974A2 (pt) Glicoconjugados de precisão como ferramentas terapêuticas
WO2020010016A1 (en) Self-adjuvanted immunogenic conjugates
KR101266552B1 (ko) 그룹 ｙ 수막염균에 대한 백신 및 그의 수막염균성 조합
WO2012106251A2 (en) Pertussis vaccine
CN105188725A (zh) 靶向真菌细胞壁多糖的抗体
WO2010019890A2 (en) Vaccine for shigella
US20200405871A1 (en) Immunogenic compositions
US10772946B2 (en) Immunogenic compositions against S. aureus
CA2513024A1 (en) Vibrio cholerae lps detoxified derivatives and immunogenic compositions containing them
EA044044B1 (ru) Иммуногенные композиции, содержащие конъюгаты полипептид-антиген с неприродными аминокислотами
MXPA98007617A (es) Conjugados de polisacaridos peptidos

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A821

Effective date: 20160301

A711 Notification of change in applicant

Free format text: JAPANESE INTERMEDIATE CODE: A711

Effective date: 20160301

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20160829

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20170710

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20170710

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20180704

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20180926

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20181220

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20190522

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20190819

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A821

Effective date: 20191122

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20200409

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20200615

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20200624

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20200721

R150 Certificate of patent or registration of utility model

Ref document number: 6739333

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250