CA2667684C - Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof - Google Patents

Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof Download PDF

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Publication number
CA2667684C
CA2667684C CA2667684A CA2667684A CA2667684C CA 2667684 C CA2667684 C CA 2667684C CA 2667684 A CA2667684 A CA 2667684A CA 2667684 A CA2667684 A CA 2667684A CA 2667684 C CA2667684 C CA 2667684C
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Prior art keywords
compound
composition
cells
hypoxic
use according
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Expired - Fee Related
Application number
CA2667684A
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English (en)
French (fr)
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CA2667684A1 (en
Inventor
David Y-W Lee
Xiaoshen Ji
James A. Raleigh
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Natural Pharmacia International Inc
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Natural Pharmacia International Inc
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Publication of CA2667684A1 publication Critical patent/CA2667684A1/en
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Expired - Fee Related legal-status Critical Current
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    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
    • A61K41/009—Neutron capture therapy, e.g. using uranium or non-boron material
    • A61K41/0095—Boron neutron capture therapy, i.e. BNCT, e.g. using boronated porphyrins
    • 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
    • A61K51/041—Heterocyclic compounds
    • A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
    • A61K51/0453—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/91—Nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Optics & Photonics (AREA)
  • Physics & Mathematics (AREA)
  • Vascular Medicine (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Urology & Nephrology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
CA2667684A 2006-10-27 2007-10-25 Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof Expired - Fee Related CA2667684C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11/588,634 2006-10-27
US11/588,634 US7842278B2 (en) 2006-10-27 2006-10-27 Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof
PCT/US2007/082548 WO2008070336A2 (en) 2006-10-27 2007-10-25 Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof

Publications (2)

Publication Number Publication Date
CA2667684A1 CA2667684A1 (en) 2008-06-12
CA2667684C true CA2667684C (en) 2015-12-29

Family

ID=39330426

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2667684A Expired - Fee Related CA2667684C (en) 2006-10-27 2007-10-25 Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof

Country Status (6)

Country Link
US (2) US7842278B2 (https=)
EP (1) EP2101825A4 (https=)
JP (1) JP5421114B2 (https=)
CN (1) CN101668547B (https=)
CA (1) CA2667684C (https=)
WO (1) WO2008070336A2 (https=)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9056136B2 (en) * 2006-10-06 2015-06-16 Natural Pharmacia International, Inc. Weakly basic 2-nitroimidazoles for the non-invasive detection of tissue hypoxia
US7842278B2 (en) * 2006-10-27 2010-11-30 Natural Pharmacia International, Inc. Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof
US8344337B2 (en) * 2010-04-21 2013-01-01 Axcelis Technologies, Inc. Silaborane implantation processes
JP5816896B2 (ja) * 2011-01-26 2015-11-18 ステラファーマ株式会社 カルボラン修飾コウジ酸／シクロデキストリン包接錯体およびその製造方法
US8741250B2 (en) 2011-08-05 2014-06-03 The Curators Of The University Of Missouri Hydroxylation of icosahedral boron compounds
US9217002B2 (en) 2011-09-15 2015-12-22 The Curators Of The University Of Missouri Cluster boron compounds and uses thereof
MD4150C1 (ro) * 2011-10-11 2012-09-30 Институт Химии Академии Наук Молдовы Procedeu de obţinere a compuşilor coordinativi ai Co(II), Ni(II) şi Zn(II) cu 2-nitro-4,5-difenilimidazol pornind de la 4,5-difenilimidazol şi nitraţii metalelor respective
US9382267B2 (en) 2011-11-30 2016-07-05 The Curators Of The University Of Missouri Small molecule inhibitors of nicotinamide phosphoribosyltransferase (NAMPT)
WO2013082150A1 (en) * 2011-11-30 2013-06-06 The Curators Of The University Of Missouri Small molecule inhibitors of nicotinamide phosphoribosyltransferase (nampt)
US9655975B2 (en) * 2012-02-13 2017-05-23 University Of Tsukuba Prodrug using nitroimidazole
MD4178C1 (ro) * 2012-02-27 2013-02-28 Институт Химии Академии Наук Молдовы Procedeu de obţinere a 2-nitro-4,5-difenilimidazolului
EP2983674A4 (en) 2013-04-08 2017-05-10 Dennis M. Brown Therapeutic benefit of suboptimally administered chemical compounds
CN105764501A (zh) 2013-07-26 2016-07-13 现代化制药公司 改善比生群治疗效益的组合物
US10076578B2 (en) * 2014-10-01 2018-09-18 Vanderbilt University Probes for imaging of hypoxia
US20180185522A1 (en) * 2014-12-12 2018-07-05 Oxford University Innovation Limited Contrast agent for imaging hypoxia
US10695446B2 (en) * 2015-05-01 2020-06-30 Vanderbilt University Composition and method for detecting hypoxia
CN106928265B (zh) * 2015-09-23 2019-01-15 苏州大学 一种碳硼烷基高氯酸铵的制备方法
WO2017181790A1 (zh) * 2016-04-19 2017-10-26 南京中硼联康医疗科技有限公司 用于消除β淀粉样蛋白沉积斑块的中子捕获治疗系统
CN106977501A (zh) * 2017-03-20 2017-07-25 华东师范大学 一种基于2‑硝基咪唑‑1‑烷基醇的低氧激活前药
CN109959612A (zh) * 2017-12-14 2019-07-02 深圳先进技术研究院 一种光声探针在制备ntr光声检测试剂中的应用
CN109956932A (zh) * 2017-12-14 2019-07-02 深圳先进技术研究院 一种可激活型光敏剂在制备肿瘤光热治疗试剂中的应用
US20240424011A1 (en) * 2021-12-21 2024-12-26 University Of Tsukuba Combination therapy of hypoxia-responsive prodrug of an anticancer drug and radiotherapy, and novel hypoxia-responsive prodrug
CN115581780A (zh) * 2022-11-03 2023-01-10 北京大学深圳研究生院 诊疗一体化核素药物、应用、药物制剂及其制备方法

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE47132B1 (en) * 1977-08-19 1983-12-28 Roche Products Ltd Novel nitroimidazoles and pharmaceutical preparations containing these as well as their manufacture
US4282232A (en) 1979-04-26 1981-08-04 Research Corporation Nitroimidazole radiosensitizers for hypoxic tumor cells and compositions thereof
US4631289A (en) * 1982-05-27 1986-12-23 National Research Development Corporation Useful in radiotherapy of chemotherapy 4-aziridino-1-nitroimidazol-1-yl-2,3-butanediols
US4797397A (en) 1987-07-31 1989-01-10 Warner-Lambert Company 2-nitroimidazole derivatives useful as radiosensitizers for hypoxic tumor cells
CA1332738C (en) * 1987-12-04 1994-10-25 Gerald Edward Adams Nitro-substituted aromatic or hetero-aromatic compounds for use in cancer treatment
US5086068A (en) * 1988-02-26 1992-02-04 Alberta Cancer Board Immunochemical detection of hypoxia in normal and tumor tissue
GB9113487D0 (en) * 1991-06-21 1991-08-07 Amersham Int Plc Agents for hypoxic cells
GB9219565D0 (en) * 1992-09-16 1992-10-28 Adams Gerald E Novel bioreductive compounds
US5674693A (en) * 1994-03-18 1997-10-07 Natural Pharmacia International Inc. Derivatives of 2-nitro-imidazoles as hypoxic cell markers
WO2000043004A1 (en) * 1999-01-26 2000-07-27 Fox Chase Cancer Center 1,4,8,11-tetraazacyclotetradecane derivatives as radiodiganostic agents and their use in determining hypoxia and radioresistance of tumors
US9056136B2 (en) 2006-10-06 2015-06-16 Natural Pharmacia International, Inc. Weakly basic 2-nitroimidazoles for the non-invasive detection of tissue hypoxia
US7842278B2 (en) * 2006-10-27 2010-11-30 Natural Pharmacia International, Inc. Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof

Also Published As

Publication number Publication date
WO2008070336A2 (en) 2008-06-12
JP5421114B2 (ja) 2014-02-19
CN101668547B (zh) 2014-08-20
EP2101825A4 (en) 2009-12-23
US20080102026A1 (en) 2008-05-01
JP2010508292A (ja) 2010-03-18
US7842278B2 (en) 2010-11-30
WO2008070336A3 (en) 2008-11-06
EP2101825A2 (en) 2009-09-23
US20110085975A1 (en) 2011-04-14
CN101668547A (zh) 2010-03-10
CA2667684A1 (en) 2008-06-12
US8518371B2 (en) 2013-08-27

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Effective date: 20201026