CA2720935C - Improved methods and compositions for f-19 labeling of proteins, peptides and other molecules - Google Patents

Improved methods and compositions for f-19 labeling of proteins, peptides and other molecules Download PDF

Info

Publication number
CA2720935C
CA2720935C CA2720935A CA2720935A CA2720935C CA 2720935 C CA2720935 C CA 2720935C CA 2720935 A CA2720935 A CA 2720935A CA 2720935 A CA2720935 A CA 2720935A CA 2720935 C CA2720935 C CA 2720935C
Authority
CA
Canada
Prior art keywords
imp
peptide
labeled
lys
hsg
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
CA2720935A
Other languages
English (en)
French (fr)
Other versions
CA2720935A1 (en
Inventor
William J. Mcbride
Christopher A. D'souza
David M. Goldenberg
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.)
Immunomedics Inc
Original Assignee
Immunomedics Inc
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
Priority claimed from US12/112,289 external-priority patent/US7563433B2/en
Application filed by Immunomedics Inc filed Critical Immunomedics Inc
Publication of CA2720935A1 publication Critical patent/CA2720935A1/en
Application granted granted Critical
Publication of CA2720935C publication Critical patent/CA2720935C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
    • A61K51/082—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins the peptide being a RGD-containing peptide
    • 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
    • A61K47/6891—Pre-targeting systems involving an antibody for targeting specific cells
    • A61K47/6897—Pre-targeting systems with two or three steps using antibody conjugates; Ligand-antiligand therapies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/0404—Lipids, e.g. triglycerides; Polycationic carriers
    • A61K51/0406—Amines, polyamines, e.g. spermine, spermidine, amino acids, (bis)guanidines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/0491—Sugars, nucleosides, nucleotides, oligonucleotides, nucleic acids, e.g. DNA, RNA, nucleic acid aptamers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
    • A61K51/083—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins the peptide being octreotide or a somatostatin-receptor-binding peptide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
    • A61K51/088—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins conjugates with carriers being peptides, polyamino acids or proteins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
    • A61K51/10—Antibodies or immunoglobulins; Fragments thereof, the carrier being an antibody, an immunoglobulin or a fragment thereof, e.g. a camelised human single domain antibody or the Fc fragment of an antibody
    • A61K51/1084—Antibodies or immunoglobulins; Fragments thereof, the carrier being an antibody, an immunoglobulin or a fragment thereof, e.g. a camelised human single domain antibody or the Fc fragment of an antibody the antibody being a hybrid immunoglobulin
    • A61K51/109—Antibodies or immunoglobulins; Fragments thereof, the carrier being an antibody, an immunoglobulin or a fragment thereof, e.g. a camelised human single domain antibody or the Fc fragment of an antibody the antibody being a hybrid immunoglobulin immunoglobulins having two or more different antigen-binding sites or multifunctional antibodies
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Optics & Photonics (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Nanotechnology (AREA)
  • Immunology (AREA)
  • Organic Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • General Engineering & Computer Science (AREA)
  • Medical Informatics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Peptides Or Proteins (AREA)
CA2720935A 2008-04-30 2009-04-30 Improved methods and compositions for f-19 labeling of proteins, peptides and other molecules Active CA2720935C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US12/112,289 US7563433B2 (en) 2007-01-11 2008-04-30 Methods and compositions for F-18 labeling of proteins, peptides and other molecules
US12/112,289 2008-04-30
US12/343,655 US7993626B2 (en) 2007-01-11 2008-12-24 Methods and compositions for F-18 labeling of proteins, peptides and other molecules
US12/343,655 2008-12-24
PCT/US2009/042333 WO2009135015A2 (en) 2008-04-30 2009-04-30 Improved methods and compositions for f-18 labeling of proteins, peptides and other molecules

Publications (2)

Publication Number Publication Date
CA2720935A1 CA2720935A1 (en) 2009-11-05
CA2720935C true CA2720935C (en) 2018-07-31

Family

ID=41255806

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2720935A Active CA2720935C (en) 2008-04-30 2009-04-30 Improved methods and compositions for f-19 labeling of proteins, peptides and other molecules

Country Status (7)

Country Link
US (2) US7993626B2 (https=)
EP (1) EP2291678A4 (https=)
JP (1) JP5608914B2 (https=)
CN (1) CN102066974B (https=)
AU (1) AU2009242641B2 (https=)
CA (1) CA2720935C (https=)
WO (1) WO2009135015A2 (https=)

Families Citing this family (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7597876B2 (en) * 2007-01-11 2009-10-06 Immunomedics, Inc. Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules
US8574854B2 (en) * 2002-06-14 2013-11-05 Immunomedics, Inc. Anti-mucin antibodies for early detection and treatment of pancreatic cancer
US7993626B2 (en) * 2007-01-11 2011-08-09 Immunomedics, Inc. Methods and compositions for F-18 labeling of proteins, peptides and other molecules
US7563433B2 (en) * 2007-01-11 2009-07-21 Immunomedics, Inc. Methods and compositions for F-18 labeling of proteins, peptides and other molecules
US8398956B2 (en) * 2007-01-11 2013-03-19 Immunomedics, Inc. In vivo copper-free click chemistry for delivery of therapeutic and/or diagnostic agents
US8709382B2 (en) * 2007-01-11 2014-04-29 Immunomedics, Inc. Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules
US8545809B2 (en) * 2007-01-11 2013-10-01 Immunomedics, Inc. Methods and compositions for improved 18F labeling of proteins, peptides and other molecules
US8889100B2 (en) * 2007-01-11 2014-11-18 Immunomedics, Inc. Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules
US20160045626A1 (en) * 2007-01-11 2016-02-18 Immunomedics, Inc. Methods and Compositions for Improved Labeling of Targeting Peptides
US10556873B2 (en) 2008-02-22 2020-02-11 Illinois Institute Of Technology Bimodal ligands with macrocyclic and acyclic binding moieties, complexes and compositions thereof, and methods of using
US9446995B2 (en) 2012-05-21 2016-09-20 Illinois Institute Of Technology Synthesis of therapeutic and diagnostic drugs centered on regioselective and stereoselective ring opening of aziridinium ions
WO2010011367A2 (en) * 2008-02-22 2010-01-28 Illinois Institute Of Technology Bimodal ligands with macrocyclic and acyclic binding moieties, complexes and compositions thereof, and methods of using
US10189803B2 (en) 2008-02-22 2019-01-29 Illinois Institute Of Technology Synthesis of therapeutic and diagnostic drugs centered on regioselective and stereoselective ring opening of aziridinium ions
US20120165650A1 (en) 2010-12-22 2012-06-28 General Electric Company Her2 binders
CN102666567B (zh) * 2009-12-04 2015-08-26 免疫医疗公司 用于蛋白质、肽和其它分子的改进的f-18标记的方法和组合物
AU2011336396B2 (en) * 2010-12-02 2016-02-04 Immunomedics, Inc. In vivo copper-free click chemistry for delivery of therapeutic and/or diagnostic agents
CA3159948A1 (en) * 2010-12-22 2012-07-19 General Electric Company Radiolabled her2 binding peptides
KR101142153B1 (ko) 2011-02-01 2012-05-10 서울대학교산학협력단 개선된 플루오르-18 표지를 위한 트리아자노난 유도체 또는 이의 약학적으로 허용가능한 염
CN102295685B (zh) * 2011-07-03 2013-07-10 江苏省原子医学研究所 一种18f标记的prgd2化合物、其药盒、药盒制备方法及应用
GB201411569D0 (en) 2014-06-30 2014-08-13 Ge Healthcare Ltd Novel formulation and method of synthesis
KR20140102700A (ko) * 2011-12-21 2014-08-22 지이 헬쓰케어 리미티드 시트레이트 완충제 내 18ｆ―플루시클로빈 조성물
US11534494B2 (en) 2011-12-21 2022-12-27 Ge Healthcare Limited Formulation and method of synthesis
GB201201062D0 (en) * 2012-01-23 2012-03-07 Ge Healthcare Ltd Radiofluorination method
CN104854126B (zh) 2012-11-30 2018-10-16 国立大学法人京都大学 多肽及成像方法
CN103030689B (zh) * 2012-12-27 2014-09-24 无锡米度生物技术有限公司 一种cart多肽化合物及其制备方法和应用
CA2904969C (en) 2013-03-13 2025-06-17 Imaginab, Inc. DIFFERENTIATION CLUSTER ANTIGEN-BINDING GENETIC CONSTRUCTIONS 8
WO2015051362A1 (en) 2013-10-04 2015-04-09 Illinois Institute Of Technology Multifunctional chelators, complexes, and compositions thereof, and methods of using same
WO2015119763A1 (en) * 2014-02-06 2015-08-13 Immunomedics, Inc. Al-f-18-labeled, al-f-19-labeled and ga-68-labeled gastrin-releasing peptide receptor (grpr)-antagonists for imaging of prostate cancer
US11420910B2 (en) * 2014-10-30 2022-08-23 Katholieke Universitet Leuven Methods for low temperature fluorine-18 radiolabeling of biomolecules
US11318163B2 (en) 2015-02-18 2022-05-03 Enlivex Therapeutics Ltd Combination immune therapy and cytokine control therapy for cancer treatment
US11512289B2 (en) 2015-02-18 2022-11-29 Enlivex Therapeutics Rdo Ltd Combination immune therapy and cytokine control therapy for cancer treatment
US11497767B2 (en) 2015-02-18 2022-11-15 Enlivex Therapeutics R&D Ltd Combination immune therapy and cytokine control therapy for cancer treatment
US11000548B2 (en) 2015-02-18 2021-05-11 Enlivex Therapeutics Ltd Combination immune therapy and cytokine control therapy for cancer treatment
WO2016170541A1 (en) 2015-04-21 2016-10-27 Enlivex Therapeutics Ltd. Therapeutic pooled blood apoptotic cell preparations and uses thereof
US11304976B2 (en) 2015-02-18 2022-04-19 Enlivex Therapeutics Ltd Combination immune therapy and cytokine control therapy for cancer treatment
US11596652B2 (en) 2015-02-18 2023-03-07 Enlivex Therapeutics R&D Ltd Early apoptotic cells for use in treating sepsis
CN105277715A (zh) * 2015-05-28 2016-01-27 广州凯拓生物科技开发有限公司 巨噬细胞迁移抑制因子(mif)作为早期阿尔茨海默病血清分子标志物
WO2017027325A1 (en) 2015-08-07 2017-02-16 Imaginab, Inc. Antigen binding constructs to target molecules
CN109069539A (zh) 2016-02-18 2018-12-21 恩立夫克治疗有限责任公司 用于癌症治疗的联合免疫疗法和细胞因子控制疗法
WO2017150549A1 (ja) * 2016-03-01 2017-09-08 国立大学法人 千葉大学 放射性標識薬剤
JP2019522625A (ja) 2016-05-02 2019-08-15 ユニバーシティ オブ ピッツバーグ −オブ ザ コモンウェルス システム オブ ハイヤー エデュケイション 分子画像化及び／又は放射免疫治療のための二量体化戦略及び化合物
TWI794171B (zh) 2016-05-11 2023-03-01 美商滬亞生物國際有限公司 Ｈｄａｃ抑制劑與ｐｄ-ｌ１抑制劑之組合治療
TWI808055B (zh) 2016-05-11 2023-07-11 美商滬亞生物國際有限公司 Hdac 抑制劑與 pd-1 抑制劑之組合治療
TWI651097B (zh) * 2016-10-19 2019-02-21 行政院原子能委員會核能研究所 造影劑前驅物之製備方法
CN107353323B (zh) * 2016-12-26 2021-04-27 南京江原安迪科正电子研究发展有限公司 Al18F标记的PSMA靶向抑制剂及其制备方法与应用
WO2018147960A1 (en) 2017-02-08 2018-08-16 Imaginab, Inc. Extension sequences for diabodies
EP3773670A4 (en) * 2018-04-05 2022-03-09 Tarveda Therapeutics, Inc. Hsp90-targeting conjugates and formulations thereof
AU2019407851B8 (en) 2018-12-18 2025-10-09 Provincial Health Services Authority Dual mode 18f-labelled theranostic compounds and uses thereof
US11396535B2 (en) 2019-03-01 2022-07-26 Provincial Health Services Authority Cyclic peptide analogs of melanocortin and amanitin and methods of making such
WO2020210909A1 (en) 2019-04-17 2020-10-22 Provincial Health Services Authority Novel radiolabelled compounds for diagnosis or treatment of prostate-specific membrane antigen-expressing cancer
JP2022533145A (ja) * 2019-05-13 2022-07-21 シャンハイ ポラリス バイオロジー カンパニー， リミテッド 生体分子を標識するためのタグ
CN113651662B (zh) * 2020-12-31 2023-10-27 复旦大学附属华山医院 一种靶向fgfr的新型肿瘤pet分子探针及其制备方法
CN115433138A (zh) * 2022-10-24 2022-12-06 苏州思萃同位素技术研究所有限公司 一种氘代配体及其制备方法
CN117919452A (zh) * 2023-03-09 2024-04-26 中国科学院宁波材料技术与工程研究所 一种亚细胞器主动靶向成像探针及其制备方法
CN119661643A (zh) * 2024-12-17 2025-03-21 北京肿瘤医院(北京大学肿瘤医院) 一种cd25靶向环状多肽、分子探针及应用

Family Cites Families (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1222691A (en) * 1981-12-29 1987-06-09 Wilhelmus T. Goedemans Method of preparing radionuclide-labelled proteins, in particular antibodies or antibody fragments
FR2604092B1 (fr) * 1986-09-19 1990-04-13 Immunotech Sa Immunoreactifs destines a cibler les cellules animales pour leur visualisation ou leur destruction in vivo
US5446147A (en) * 1992-04-03 1995-08-29 Trustees Of The University Of Pennsylvania Fluorinated and iodinated dopamine agents
US6187284B1 (en) * 1997-09-03 2001-02-13 Immunomedics, Inc. Fluorination of proteins and peptides for F-18 positron emission tomography
US7387772B1 (en) * 1999-06-22 2008-06-17 Immunimedics, Inc. Chimeric, human and humanized anti-CSAP monoclonal antibodies
US7138103B2 (en) * 1998-06-22 2006-11-21 Immunomedics, Inc. Use of bi-specific antibodies for pre-targeting diagnosis and therapy
US6962702B2 (en) * 1998-06-22 2005-11-08 Immunomedics Inc. Production and use of novel peptide-based agents for use with bi-specific antibodies
US6056939A (en) * 1998-08-28 2000-05-02 Desreux; Jean F. Self-assembling heteropolymetallic chelates as imaging agents and radiopharmaceuticals
DE19846148C2 (de) * 1998-10-01 2002-10-10 Igor Popov Verfahren zur Beurteilung der oxidativen Modifikation proteinhaltiger Stoffe mittels Messung ihrer antiradikalen Aktivität
US6207858B1 (en) * 1999-03-03 2001-03-27 Idec Pharmaceuticals Corporation Regioselective synthesis of DTPA derivatives
WO2001028595A1 (en) * 1999-10-15 2001-04-26 Mayo Foundation For Medical Education And Research Cobalamin conjugates useful as imaging and therapeutic agents
US6605615B2 (en) * 2000-03-01 2003-08-12 Tularik Inc. Hydrazones and analogs as cholesterol lowering agents
US7011816B2 (en) * 2001-12-26 2006-03-14 Immunomedics, Inc. Labeling targeting agents with gallium-68 and gallium-67
WO2003074566A2 (en) * 2002-03-01 2003-09-12 Immunomedics, Inc. Rs7 antibodies
US7081452B2 (en) * 2002-06-03 2006-07-25 The United States Of America As Represented By The Department Of Health And Human Services Scorpionate-like pendant macrocyclic ligands, complexes and compositions thereof, and methods of using same
US7993626B2 (en) * 2007-01-11 2011-08-09 Immunomedics, Inc. Methods and compositions for F-18 labeling of proteins, peptides and other molecules
US7563433B2 (en) * 2007-01-11 2009-07-21 Immunomedics, Inc. Methods and compositions for F-18 labeling of proteins, peptides and other molecules
US7597876B2 (en) * 2007-01-11 2009-10-06 Immunomedics, Inc. Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules
FR2841558B1 (fr) * 2002-07-01 2004-08-13 Commissariat Energie Atomique Peptides marques ayant une affinite pour un phospholipide et utilisations
CA2533878A1 (en) * 2003-07-29 2005-09-22 Immunomedics, Inc. Fluorinated carbohydrate conjugates
CA2555597C (en) * 2004-02-13 2016-06-14 The University Of British Columbia Radiolabeled compounds and compositions, their precursors and methods for their production
DE102004034517A1 (de) * 2004-07-16 2006-02-16 Covion Organic Semiconductors Gmbh Metallkomplexe
WO2006017619A2 (en) * 2004-08-06 2006-02-16 The Regents Of The University Of California Receptor-binding cyclic peptides and methods of use
EP1874824A4 (en) * 2005-04-06 2009-12-30 Ibc Pharmaceuticals Inc METHODS OF GENERATING STABLE COMPOUND RELATED COMPLEXES OF HOMODIMERS, HOMOTRATEERS OR DIMER SIZES AND USES THEREOF
CA2619941C (en) 2005-08-31 2014-04-01 Immunomedics, Inc. F-18 peptides for pre targeted positron emission tomography imaging
EP1884515A1 (en) * 2006-07-31 2008-02-06 Laboratorios del Dr. Esteve S.A. Substituted indanyl sulfonamide compounds, their preparation and use as medicaments
EP2061519B1 (en) * 2006-09-15 2016-03-30 Siemens Medical Solutions USA, Inc. Click chemistry-derived cyclopeptide derivatives as imaging agents for integrins
AU2007343600B2 (en) 2007-01-11 2012-06-28 Immunomedics, Inc. Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules
WO2009033288A1 (en) * 2007-09-11 2009-03-19 Voiceage Corporation Method and device for fast algebraic codebook search in speech and audio coding

Also Published As

Publication number Publication date
CN102066974B (zh) 2014-12-17
JP2011523697A (ja) 2011-08-18
US8147800B2 (en) 2012-04-03
US7993626B2 (en) 2011-08-09
US20090155166A1 (en) 2009-06-18
CN102066974A (zh) 2011-05-18
AU2009242641B2 (en) 2015-07-30
AU2009242641A1 (en) 2009-11-05
EP2291678A4 (en) 2013-11-20
WO2009135015A8 (en) 2010-04-08
US20110280801A1 (en) 2011-11-17
WO2009135015A2 (en) 2009-11-05
EP2291678A2 (en) 2011-03-09
WO2009135015A3 (en) 2010-01-07
CA2720935A1 (en) 2009-11-05
JP5608914B2 (ja) 2014-10-22

Similar Documents

Publication Publication Date Title
CA2720935C (en) Improved methods and compositions for f-19 labeling of proteins, peptides and other molecules
US8617518B2 (en) Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules
US8153100B2 (en) Methods and compositions for F-18 labeling of proteins, peptides and other molecules
US9028800B2 (en) Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules
EP2651411B1 (en) Methods and compositions for improved f-18 labeling of proteins, peptides and other molecules
US8709382B2 (en) Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules
US9115172B2 (en) Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20140317

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 16TH ANNIV.) - STANDARD

Year of fee payment: 16

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20241221

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT

Effective date: 20241221

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20241221

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 17TH ANNIV.) - STANDARD

Year of fee payment: 17

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20260310

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20260310