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WO2011095593A1 - Précurseur iodo pour un produit d'imagerie par tep de plaques amyloïdes - Google Patents

Précurseur iodo pour un produit d'imagerie par tep de plaques amyloïdes Download PDF

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Publication number
WO2011095593A1
WO2011095593A1 PCT/EP2011/051660 EP2011051660W WO2011095593A1 WO 2011095593 A1 WO2011095593 A1 WO 2011095593A1 EP 2011051660 W EP2011051660 W EP 2011051660W WO 2011095593 A1 WO2011095593 A1 WO 2011095593A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
formula
precursor
acid
mmol
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.)
Ceased
Application number
PCT/EP2011/051660
Other languages
English (en)
Inventor
Heribert Schmitt-Willich
Tobias Heinrich
Damian Brockschnieder
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.)
Bayer Pharma AG
Original Assignee
Bayer Schering Pharma AG
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 Bayer Schering Pharma AG filed Critical Bayer Schering Pharma AG
Publication of WO2011095593A1 publication Critical patent/WO2011095593A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • 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

Definitions

  • Kryptofix is 4,7, 13, 16,21 ,24-Hexaoxa-1 , 10- diazabicyclo[8.8.8]-hexacosane.
  • the nucleophilic substitution of the precursor works pref- erably in the presence of a base such as Tetrabutylammonium hydroxide (NBu 4 OH), Tetrabutylammonium carbonate ((NBu 4 ) 2 C0 3 ), Tetrabutylammonium hydrogencarbonate (NBu 4 HC0 3 ), K 2 C0 3 etc. and at elevated temperatures.
  • a base such as Tetrabutylammonium hydroxide (NBu 4 OH), Tetrabutylammonium carbonate ((NBu 4 ) 2 C0 3 ), Tetrabutylammonium hydrogencarbonate (NBu 4 HC0 3 ), K 2 C0 3 etc. and at elevated temperatures.
  • the addition of crown ethers such as Kryptofix (K2.2.2) can influence the reaction
  • reaction mixture was refluxed for 6 h and stirred at room temperature overnight. After evaporation of the solvents the residue was chromatographed on silica gel using a dichloro- methane/methanol gradient.
  • the QMA cartridge (Waters) can also be eluted with 2 mL of a tetrabutylammonium hydroxide (TBAOH) solution (1 .5 mL acetonitrile (MeCN), 0.3 mL H 2 0 + 8 ⁇ TBAOH sol. (40 %)) into the reactor.
  • TAAOH tetrabutylammonium hydroxide
  • MeCN acetonitrile
  • Anhydrous MeCN (1 mL) was added and evaporated as before.

Landscapes

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

Abstract

L'invention porte sur un précurseur pour un traceur de TEP marqué par [18F] pour l'imagerie de la maladie d'Alzheimer, sur sa synthèse et sur le procédé permettant de préparer le traceur de TEP marqué par [18F] correspondant.
PCT/EP2011/051660 2010-02-08 2011-02-04 Précurseur iodo pour un produit d'imagerie par tep de plaques amyloïdes Ceased WO2011095593A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP10075054 2010-02-08
EP10075054.6 2010-02-08

Publications (1)

Publication Number Publication Date
WO2011095593A1 true WO2011095593A1 (fr) 2011-08-11

Family

ID=43645878

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2011/051660 Ceased WO2011095593A1 (fr) 2010-02-08 2011-02-04 Précurseur iodo pour un produit d'imagerie par tep de plaques amyloïdes

Country Status (4)

Country Link
AR (1) AR080289A1 (fr)
TW (1) TW201201846A (fr)
UY (1) UY33218A (fr)
WO (1) WO2011095593A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017503012A (ja) * 2013-12-20 2017-01-26 ベイジン ズィボォ バイオメディカル テクノロジー カンパニー、リミテッド フェニルベンジルエーテル系誘導体及びその調製方法と応用
WO2018089491A1 (fr) * 2016-11-08 2018-05-17 The Regents Of The University Of California Procédés destinés à la synthèse multi-dose du [f-18]fddnp destinés à des contextes cliniques

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002036581A1 (fr) * 2000-11-06 2002-05-10 Schering Aktiengesellschaft Produits radiopharmaceutiques pour le diagnostic de la maladie d'alzheimer
WO2010028776A1 (fr) * 2008-09-12 2010-03-18 Bayer Schering Pharma Aktiengesellschaft Composés de liaison et d'imagerie pour plaques amyloïdes et leur utilisation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002036581A1 (fr) * 2000-11-06 2002-05-10 Schering Aktiengesellschaft Produits radiopharmaceutiques pour le diagnostic de la maladie d'alzheimer
WO2010028776A1 (fr) * 2008-09-12 2010-03-18 Bayer Schering Pharma Aktiengesellschaft Composés de liaison et d'imagerie pour plaques amyloïdes et leur utilisation

Non-Patent Citations (18)

* Cited by examiner, † Cited by third party
Title
BLENNOW ET AL., LANCET., vol. 368, no. 9533, 29 July 2006 (2006-07-29), pages 387 - 403
CHITI ET AL., ANNU REV BIOCHEM., vol. 75, 2006, pages 333 - 366
COHEN, MOL. IMAGING BIOL., vol. 9, 2007, pages 204 - 216
DOLLE F.: "Fluoropyridines: From conventional radiotracers to the labeling of macromolecules such as proteins and oligonucleotides", ERNST SCHERING RESEARCH FOUNDATION WORKSHOP, vol. 62, 2007, pages 113 - 157, XP009145775, DOI: doi:10.1007/978-3-540-49527-7_5
ERNST SCHERING RESEARCH FOUNDATION WORKSHOP:THE DRIVING FORCE IN MOLECULAR IMAGING SPRINGER-VERLAG BERLIN, HEIDELBERGER PLATZ 3, D-14197 BERLIN, GERMANY SERIES : ERNST SCHERING RESEARCH FOUNDATION WORKSHOP (ISSN 0947-6075(PRINT)), 2007, 62ND ERNST-SCHERING-RESEARCH-FOUNDATION ON PET CHEMISTRY; BERLIN, GERMANY; DECEMBER 05 -07, 2005, pages 113 - 157, XP009145775 *
FARRAR, TURKU PET SYMPOSIUM, 2007
HENRIKSEN ET AL., EUR. J. NUCL. MED. MOL. IMAGING, 2007
KLUNK, ANN NEUROL., vol. 55, 2004, pages 306 - 319
KUDO, J NUCL. MED, vol. 49, 2007, pages 554 - 561
LOCKHARDT, DRUG DISCOV TODAY, vol. 11, 2006, pages 1093 - 1099
NORDBERG, CURR. OPIN BIOL., vol. 20, 2007, pages 398 - 402
NORDBERG, EUR. J. NUCL. MED. MOL. IMAGING, vol. 35, 2008, pages S46 - S50
PETRELLA JR ET AL., RADIOLOGY., vol. 226, 2003, pages 315 - 336
ROWE ET AL., LANCET NEUROL, vol. 7, 2008, pages 129 - 135
SHOGHI-JADID, AM J GERIATR PSYCHIATRY, vol. 10, 2002, pages 24 - 35
SMALL ET AL., NEUROLOGY, vol. 7, 2008, pages 161 - 172
VERHOEFF, AM J GERIATR PSYCHIATRY, vol. 12, 2004, pages 584 - 595
ZHANG Y.: "Synthesis of 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2-[18F]fluoropyridin-4-yl)pyridine ([18F]NIDA522131), a novel potential radioligand for studying extrathalamic nicotinic acetylcholine receptors by PET", J LABEL COMPD RADIOPHARM, vol. 47, 2004, pages 947 - 952

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017503012A (ja) * 2013-12-20 2017-01-26 ベイジン ズィボォ バイオメディカル テクノロジー カンパニー、リミテッド フェニルベンジルエーテル系誘導体及びその調製方法と応用
WO2018089491A1 (fr) * 2016-11-08 2018-05-17 The Regents Of The University Of California Procédés destinés à la synthèse multi-dose du [f-18]fddnp destinés à des contextes cliniques
US10377701B2 (en) 2016-11-08 2019-08-13 The Regents Of The University Of California Methods for multi-dose synthesis of [F-18]FDDNP for clinical settings
US10626083B2 (en) 2016-11-08 2020-04-21 The Regents Of The University Of California Methods for multi-dose synthesis of [F-18]FDDNP for clinical settings

Also Published As

Publication number Publication date
AR080289A1 (es) 2012-03-28
UY33218A (es) 2011-09-30
TW201201846A (en) 2012-01-16

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