WO2003082350A3 - Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands - Google Patents

Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands Download PDF

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Publication number
WO2003082350A3
WO2003082350A3 PCT/EP2003/003240 EP0303240W WO03082350A3 WO 2003082350 A3 WO2003082350 A3 WO 2003082350A3 EP 0303240 W EP0303240 W EP 0303240W WO 03082350 A3 WO03082350 A3 WO 03082350A3
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WO
WIPO (PCT)
Prior art keywords
6alkyl
metabotropic glutamate
12alkyl
halo
glutamate receptor
Prior art date
Application number
PCT/EP2003/003240
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French (fr)
Other versions
WO2003082350A2 (en
Inventor
Anne Simone Josephine Lesage
Francois Paul Bischoff
Cornelus Gerardus Mari Janssen
Hilde Lavreysen
Original Assignee
Janssen Pharmaceutica Nv
Anne Simone Josephine Lesage
Francois Paul Bischoff
Cornelus Gerardus Mari Janssen
Hilde Lavreysen
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 to CN038073870A priority Critical patent/CN1642580B/en
Application filed by Janssen Pharmaceutica Nv, Anne Simone Josephine Lesage, Francois Paul Bischoff, Cornelus Gerardus Mari Janssen, Hilde Lavreysen filed Critical Janssen Pharmaceutica Nv
Priority to KR1020047012247A priority patent/KR101061561B1/en
Priority to EP03745282A priority patent/EP1492571A2/en
Priority to CA2479109A priority patent/CA2479109C/en
Priority to EA200401285A priority patent/EA009334B1/en
Priority to US10/509,069 priority patent/US7517517B2/en
Priority to NZ535438A priority patent/NZ535438A/en
Priority to AU2003226737A priority patent/AU2003226737B2/en
Priority to UA20040907678A priority patent/UA78548C2/en
Priority to BR0308945-2A priority patent/BR0308945A/en
Priority to JP2003579882A priority patent/JP4573533B2/en
Priority to MXPA04009435A priority patent/MXPA04009435A/en
Publication of WO2003082350A2 publication Critical patent/WO2003082350A2/en
Publication of WO2003082350A3 publication Critical patent/WO2003082350A3/en
Priority to HR20040870A priority patent/HRP20040870A2/en
Priority to IL164299A priority patent/IL164299A/en
Priority to ZA2004/07820A priority patent/ZA200407820B/en
Priority to NO20044635A priority patent/NO330688B1/en
Priority to HK05112028.6A priority patent/HK1079700A1/en

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    • A61K51/04—Organic compounds
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    • A61K51/0463—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
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Abstract

The present invention is concerned with radiolabelled quinoline and quinolinone derivatives according Formula (I-A)* or (I-B)* showing metabotropic glutamate receptor antagonistic activity, in particular mGlu1 receptor activity, and their preparation ; it further relates to compositions comprising them, as well as their use for marking and identifying metabotropic glutamate receptor sites and for imaging an organ. In a preferable embodiment, X represents O; R1 represents C1-6alkyl; cyclo3-12alkyl or (cycloC3-12alkyl)C1-6alkyl, wherein one or more hydrogen atoms in a C1-6alkyl-moiety or in a cycloC3-12alkyl-moiety optionally may be replaced by C1-6alkyloxy, aryl, halo or thienyl; R2 represents hydrogen; halo; C1-6alkyl or amino; R3 and R4 each independently represent hydrogen or C1-6alkyl; or R2 and R3 may be taken together to form -R2-R3-, which represents a bivalent radical of formula -Z4-CH2-CH2-CH2- or -Z4-CH2-CH2- with Z4 being O or NR11 wherein R11 is C1-6alkyl; and wherein each bivalent radical is optionally substituted with C1-6alkyl; or R3 and R4 may be taken together to form a bivalent radical of formula -CH2-CH2-CH2-CH2- ; R5 represents hydrogen; Y represents O; and aryl represents phenyl optionally substituted with halo. Most preferred are radiolabelled compounds in which the radioactive isotope is selected from the group of of 3H, 11C and 18F. The invention also relates to their use in a diagnostic method, in perticular for marking and identifying a mGluR1 receptor in biological material, as well as to their use for imaging an organ, in particular using PET.
PCT/EP2003/003240 2002-03-29 2003-03-26 Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands WO2003082350A2 (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
AU2003226737A AU2003226737B2 (en) 2002-03-29 2003-03-26 Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands
KR1020047012247A KR101061561B1 (en) 2002-03-29 2003-03-26 Radiolabeled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands
EP03745282A EP1492571A2 (en) 2002-03-29 2003-03-26 Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands
CA2479109A CA2479109C (en) 2002-03-29 2003-03-26 Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands
EA200401285A EA009334B1 (en) 2002-03-29 2003-03-26 Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands
US10/509,069 US7517517B2 (en) 2002-03-29 2003-03-26 Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands
BR0308945-2A BR0308945A (en) 2002-03-29 2003-03-26 Radiolabeled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands
UA20040907678A UA78548C2 (en) 2002-03-29 2003-03-26 Radiolabelled quinoline and quinolinone derivatives and use thereof as metabotropic ligands of glutamate receptor
NZ535438A NZ535438A (en) 2002-03-29 2003-03-26 Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands
CN038073870A CN1642580B (en) 2002-03-29 2003-03-26 Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands
JP2003579882A JP4573533B2 (en) 2002-03-29 2003-03-26 Radiolabeled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands
MXPA04009435A MXPA04009435A (en) 2002-03-29 2003-03-26 Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands.
HR20040870A HRP20040870A2 (en) 2002-03-29 2004-09-21 Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptorligands
IL164299A IL164299A (en) 2002-03-29 2004-09-27 Radiolabelled quinoline and quinolinone derivatives and their use in diagnostic method as metabotropic glutamate receptor ligands
ZA2004/07820A ZA200407820B (en) 2002-03-29 2004-09-28 Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands
NO20044635A NO330688B1 (en) 2002-03-29 2004-10-27 Radiolabeled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands
HK05112028.6A HK1079700A1 (en) 2002-03-29 2005-12-28 Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP02076254 2002-03-29
EP02076254.8 2002-03-29

Publications (2)

Publication Number Publication Date
WO2003082350A2 WO2003082350A2 (en) 2003-10-09
WO2003082350A3 true WO2003082350A3 (en) 2004-03-04

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PCT/EP2003/003240 WO2003082350A2 (en) 2002-03-29 2003-03-26 Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands

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US (1) US7517517B2 (en)
EP (1) EP1492571A2 (en)
JP (1) JP4573533B2 (en)
KR (1) KR101061561B1 (en)
CN (1) CN1642580B (en)
AU (1) AU2003226737B2 (en)
BR (1) BR0308945A (en)
CA (1) CA2479109C (en)
EA (1) EA009334B1 (en)
HK (1) HK1079700A1 (en)
HR (1) HRP20040870A2 (en)
IL (1) IL164299A (en)
MX (1) MXPA04009435A (en)
NO (1) NO330688B1 (en)
NZ (1) NZ535438A (en)
PL (1) PL218788B1 (en)
UA (1) UA78548C2 (en)
WO (1) WO2003082350A2 (en)
ZA (1) ZA200407820B (en)

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