CA2683434A1 - Development of molecular imaging probes for carbonic anhydrase-ix using click chemistry - Google Patents

Development of molecular imaging probes for carbonic anhydrase-ix using click chemistry Download PDF

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Publication number
CA2683434A1
CA2683434A1 CA002683434A CA2683434A CA2683434A1 CA 2683434 A1 CA2683434 A1 CA 2683434A1 CA 002683434 A CA002683434 A CA 002683434A CA 2683434 A CA2683434 A CA 2683434A CA 2683434 A1 CA2683434 A1 CA 2683434A1
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CA
Canada
Prior art keywords
methyl
triazol
6alkyl
yloxy
phenyl
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.)
Abandoned
Application number
CA002683434A
Other languages
English (en)
French (fr)
Inventor
Hartmuth C Kolb
Joseph C. Walsh
Dhanalakshmi Kasi
Vani Mocharla
Bing Wang
Umesh B. Gangadharmath
Brian A. Duclos
Kai Chen
Wei Zhang
Gang Chen
Henry Clifton Padgett
Farhad Karimi
Peter J. H. Scott
Zhiyong Gao
Qianwa Liang
Thomas Lee Collier
Tieming Zhao
Chunfang Xia
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.)
Siemens Medical Solutions USA Inc
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2683434A1 publication Critical patent/CA2683434A1/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4192—1,2,3-Triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
    • A61K49/10—Organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D403/12—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 chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/48—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving transferase
    • C12Q1/485—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving transferase involving kinase
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2500/00—Screening for compounds of potential therapeutic value
    • G01N2500/04—Screening involving studying the effect of compounds C directly on molecule A (e.g. C are potential ligands for a receptor A, or potential substrates for an enzyme A)
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2500/00—Screening for compounds of potential therapeutic value
    • G01N2500/10—Screening for compounds of potential therapeutic value involving cells

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)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Epidemiology (AREA)
  • Physics & Mathematics (AREA)
  • Biotechnology (AREA)
  • Immunology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Analytical Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Radiology & Medical Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
CA002683434A 2007-04-05 2008-04-07 Development of molecular imaging probes for carbonic anhydrase-ix using click chemistry Abandoned CA2683434A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US92206507P 2007-04-05 2007-04-05
US60/922,065 2007-04-05
PCT/US2008/059599 WO2008124703A2 (en) 2007-04-05 2008-04-07 Development of molecular imaging probes for carbonic anhydrase-ix using click chemistry

Publications (1)

Publication Number Publication Date
CA2683434A1 true CA2683434A1 (en) 2008-10-16

Family

ID=39743771

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002683434A Abandoned CA2683434A1 (en) 2007-04-05 2008-04-07 Development of molecular imaging probes for carbonic anhydrase-ix using click chemistry

Country Status (7)

Country Link
US (2) US7829063B2 (enExample)
EP (2) EP2468734A1 (enExample)
JP (1) JP2010523599A (enExample)
KR (2) KR20090127433A (enExample)
CN (1) CN101679318A (enExample)
CA (1) CA2683434A1 (enExample)
WO (1) WO2008124703A2 (enExample)

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CA2703981A1 (en) * 2007-10-29 2009-05-07 Schering Corporation Heterocyclic urea and thiourea derivatives and methods of use thereof
EP2823826A3 (en) * 2008-01-09 2015-03-25 Molecular Insight Pharmaceuticals, Inc. Inhibitors of carbonic anhydrase IX
WO2010065899A2 (en) 2008-12-05 2010-06-10 Molecular Insight Pharmaceuticals, Inc. Technetium-and rhenium-bis(heteroaryl)complexes and methods of use thereof
NZ593110A (en) 2008-12-09 2013-06-28 Gilead Sciences Inc pteridinone derivatives as MODULATORS OF TOLL-LIKE RECEPTORS
US8465725B2 (en) 2009-06-15 2013-06-18 Molecular Insight Pharmaceuticlas, Inc. Process for production of heterodimers of glutamic acid
WO2011018798A2 (en) * 2009-08-14 2011-02-17 Indian Association For The Cultivation Of Science Morpholino-based antisense agent
CA2777071A1 (en) * 2009-10-21 2011-04-28 Bayer Pharma Aktiengesellschaft Substituted halophenoxybenzamide derivatives
WO2011127345A1 (en) * 2010-04-08 2011-10-13 Siemens Medical Solutions Usa, Inc. Synthesis of 18f-labeled tracers in hydrous organic solvents
US10639608B2 (en) 2010-04-08 2020-05-05 Siemens Medical Solutions Usa, Inc. System, device and method for preparing tracers and transferring materials during radiosynthesis
WO2012057312A1 (ja) * 2010-10-29 2012-05-03 クリノ株式会社 タウイメージングプローブ
ES2703498T3 (es) * 2010-11-13 2019-03-11 Innocrin Pharmaceuticals Inc 1-(6,7-Bis(difluorometoxi)naftalen-2-il)-2-metil-1-(1H-1,2,3-triazol-4-il)propan-1-ol como inhibidor de CYP17 para el tratamiento de enfermedades dependientes de andrógenos como el cáncer de próstata
WO2012118715A2 (en) * 2011-02-28 2012-09-07 The Board Of Trustees Of Leland Stanford Junior University Non-peptidic quenched fluorescent imaging probes
CN102219753B (zh) * 2011-04-21 2012-10-31 山东大学 一种三氮唑类化合物及其制备方法与应用
AU2012253502C1 (en) 2011-05-09 2017-12-14 Visen Medical, Inc. Carbonic anhydrase targeting agents and methods of using same
JP2014156400A (ja) * 2011-05-24 2014-08-28 Astellas Pharma Inc 腫瘍の画像診断用標識誘導体
EP2800471A4 (en) 2012-01-06 2015-11-04 Molecular Insight Pharm Inc METAL COMPLEX OF POLY (CARBOXYL) AMINE CONTAINING LIGANDS HAVING AFFINITY FOR CARBON IX ANHYDRASE
WO2013148319A1 (en) 2012-03-30 2013-10-03 Visen Medical, Inc. Bacterial imaging agents and methods of using same
JP6468602B2 (ja) 2013-01-14 2019-02-13 モレキュラ インサイト ファーマシューティカルズ インコーポレイテッド トリアジン系放射性医薬品及び放射線造影剤
BR112016010164A2 (pt) 2013-11-05 2017-08-08 Bayer Cropscience Ag novos compostos para o combate aos ártropodes
EA201790024A1 (ru) 2014-07-11 2017-07-31 Джилид Сайэнс, Инк. Модуляторы toll-подобных рецепторов для лечения вич
CN104212440B (zh) * 2014-09-03 2016-03-30 无锡艾德美特生物科技有限公司 一类喹唑啉类荧光探针及其制备和应用
JP6373490B2 (ja) * 2014-09-16 2018-08-15 ギリアード サイエンシーズ， インコーポレイテッド Ｔｏｌｌ様受容体モジュレーターを調製する方法
US9738646B2 (en) 2014-09-16 2017-08-22 Gilead Sciences, Inc. Solid forms of a toll-like receptor modulator
WO2016150953A1 (en) 2015-03-24 2016-09-29 H. Lundbeck A/S Manufacture of 4,5,6,7-tetrahydroisozaxolo[5,4-c]pyridin-3-ol
LT6401B (lt) 2015-07-28 2017-06-12 Vilniaus Universitetas Karboanhidrazės selektyvūs inhibitoriai
CN105541825A (zh) * 2015-12-28 2016-05-04 中国药科大学 三氮唑衍生物制备方法及其作为药物的用途
KR102531494B1 (ko) * 2016-05-13 2023-05-10 더 존스 홉킨스 유니버시티 탄산 탈수효소 ix를 표적으로 하는 핵 영상화 및 방사선치료 제제 및 이의 용도
US10695450B2 (en) 2016-07-26 2020-06-30 Laboratoires Cyclopharma Synthesis of a radioactive agent composition
EP3612526A2 (en) * 2017-04-20 2020-02-26 The Regents of the University of California K-ras modulators
PL3668856T3 (pl) 2017-08-17 2021-12-13 Glaxosmithkline Intellectual Property Development Limited Nowe związki tetrazolu i ich zastosowanie w leczeniu gruźlicy
KR102147971B1 (ko) * 2019-11-22 2020-08-25 국방과학연구소 반응용매에 대한 혼화성 차이를 이용한 화학선택적 트리아졸의 제조방법
WO2025113696A1 (zh) * 2023-11-30 2025-06-05 赣州和美药业股份有限公司 一种化合物及其应用

Family Cites Families (7)

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Publication number Priority date Publication date Assignee Title
US6562319B2 (en) * 2001-03-12 2003-05-13 Yissum Research Development Company Of The Hebrew University Of Jerusalem Radiolabeled irreversible inhibitors of epidermal growth factor receptor tyrosine kinase and their use in radioimaging and radiotherapy
US7550424B2 (en) * 2002-11-26 2009-06-23 Institute Of Virology Slovak Academy Of Sciences CA IX-specific inhibitors
US20060269942A1 (en) * 2005-04-27 2006-11-30 Kolb Hartmuth C In situ click chemistry method for screening high affinity molecular imaging probes
EP1733742A1 (en) 2005-06-17 2006-12-20 Universiteit Utrecht Holding B.V. Dendrimers multivalently substituted with active groups
AU2006277117B2 (en) 2005-08-05 2013-01-10 Syntarga B.V. Triazole-containing releasable linkers and conjugates comprising the same
US8470587B2 (en) 2006-08-28 2013-06-25 The Trustees Of The University Of Pennsylvania 129Xe biosensors and their use
US20080213175A1 (en) 2006-09-15 2008-09-04 Kolb Hartmuth C Click chemistry-derived cyclic peptidomimetics as integrin markers

Also Published As

Publication number Publication date
EP2468734A1 (en) 2012-06-27
WO2008124703A3 (en) 2009-02-05
JP2010523599A (ja) 2010-07-15
US20090123372A1 (en) 2009-05-14
US7829063B2 (en) 2010-11-09
KR20090127433A (ko) 2009-12-11
US8354092B2 (en) 2013-01-15
CN101679318A (zh) 2010-03-24
EP2129666A2 (en) 2009-12-09
WO2008124703A2 (en) 2008-10-16
US20100317842A1 (en) 2010-12-16
KR20120003499A (ko) 2012-01-10

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Effective date: 20121217