GB2463436A - (11C)methoxy-radiolabelled 2,3',4,5'-tetramethylstilbene (TMS) and its preparation and use - Google Patents

(11C)methoxy-radiolabelled 2,3',4,5'-tetramethylstilbene (TMS) and its preparation and use Download PDF

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Publication number
GB2463436A
GB2463436A GB1001001A GB201001001A GB2463436A GB 2463436 A GB2463436 A GB 2463436A GB 1001001 A GB1001001 A GB 1001001A GB 201001001 A GB201001001 A GB 201001001A GB 2463436 A GB2463436 A GB 2463436A
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United Kingdom
Prior art keywords
methoxy
radiolabelled
tms
methods
tetramethoxystilbene
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.)
Withdrawn
Application number
GB1001001A
Other versions
GB201001001D0 (en
Inventor
Timothy Smith
Lutz F Schweiger
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.)
University of Aberdeen
Original Assignee
University of Aberdeen
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 University of Aberdeen filed Critical University of Aberdeen
Publication of GB201001001D0 publication Critical patent/GB201001001D0/en
Publication of GB2463436A publication Critical patent/GB2463436A/en
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A61K31/075—Ethers or acetals
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • A61K31/09—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon having two or more such linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/001—Acyclic or carbocyclic compounds
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

This invention pertains generally to the field of radiochemical synthesis, and more specifically to methods of preparing [11C]methoxy-radiolabelled 2,3',4,5' -tetramethoxystilbene (TMS) from an unlabelled hydroxy precursor of 2,3',4,5' -tetramethoxystilbene (TMS) that has a pendant hydroxyl group, by reaction with [11C]methyl trifluoromethanesulfonate (CF3SO2O11CH3), also known as [11C]methyl triflate, or [11C]methyl iodide (11CH3I). This reaction converts the pendant hydroxyl group into a pendant [11C]methoxy group. The resulting [11C]methoxy-radiolabelled product is useful, for example, as an in vivo positron emission tomography (PET) tracer, for example, for tumours (e.g., cancer tumours) and/or beta amyloid plaques (e.g., Alzheimer's disease). The present invention also pertains to the resulting [11C]methoxy radiolabelled products, compositions comprising them, their use in methods of (e.g., PET) imaging, their use in methods of medical treatment and diagnosis, etc.
GB1001001A 2007-06-22 2008-06-20 (11C)methoxy-radiolabelled 2,3',4,5'-tetramethylstilbene (TMS) and its preparation and use Withdrawn GB2463436A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US94562507P 2007-06-22 2007-06-22
PCT/GB2008/002111 WO2009001046A2 (en) 2007-06-22 2008-06-20 [11c]methoxy-radiolabelled 2,3',4,5'-tetramethylstilbene (tms) and its preparation and use

Publications (2)

Publication Number Publication Date
GB201001001D0 GB201001001D0 (en) 2010-03-10
GB2463436A true GB2463436A (en) 2010-03-17

Family

ID=39816887

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1001001A Withdrawn GB2463436A (en) 2007-06-22 2008-06-20 (11C)methoxy-radiolabelled 2,3',4,5'-tetramethylstilbene (TMS) and its preparation and use

Country Status (2)

Country Link
GB (1) GB2463436A (en)
WO (1) WO2009001046A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI644665B (en) * 2017-12-08 2018-12-21 衛生福利部國家中醫藥研究所 Use of stilbene and benzofuran derivatives for the treatment of neurological diseases

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003018013A1 (en) * 2001-08-31 2003-03-06 Promeditech, Inc. Stilbene derivative having cytochrome p450 1b1 inhibitory activity, pharmaceutically acceptable salt thereof, method for preparing the same, and composition including the same
WO2006066104A2 (en) * 2004-12-17 2006-06-22 The Trustees Of The University Of Pennsylvania Stilbene derivatives and their use for binding and imaging amyloid plaques

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003018013A1 (en) * 2001-08-31 2003-03-06 Promeditech, Inc. Stilbene derivative having cytochrome p450 1b1 inhibitory activity, pharmaceutically acceptable salt thereof, method for preparing the same, and composition including the same
WO2006066104A2 (en) * 2004-12-17 2006-06-22 The Trustees Of The University Of Pennsylvania Stilbene derivatives and their use for binding and imaging amyloid plaques

Also Published As

Publication number Publication date
WO2009001046A2 (en) 2008-12-31
WO2009001046A3 (en) 2009-02-26
GB201001001D0 (en) 2010-03-10

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Legal Events

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WAP Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1)