EP 2282982 A1 20110216 - NOVEL [F-18]-LABELLED L-GLUTAMIC ACID- AND L-GLUTAMINE DERIVATIVES (I), USE THEREOF AND METHOD FOR THEIR PRODUCTION
Title (en)
NOVEL [F-18]-LABELLED L-GLUTAMIC ACID- AND L-GLUTAMINE DERIVATIVES (I), USE THEREOF AND METHOD FOR THEIR PRODUCTION
Title (de)
NEUE [F-18]-MARKIERTE L-GLUTAMINSÄURE- UND L-GLUTAMINDERIVATE (I), IHRE VERWENDUNG SOWIE VERFAHREN ZU IHRER HERSTELLUNG
Title (fr)
NOUVEAUX DÉRIVÉS (I) D'ACIDE L-GLUTAMIQUE ET DE L-GLUTAMINE MARQUÉS AU [F-18], LEUR UTILISATION ET LEUR PROCÉDÉ DE PRODUCTION
Publication
Application
Priority
- EP 2009003420 W 20090514
- EP 08075510 A 20080520
- EP 09749581 A 20090514
Abstract (en)
[origin: EP2123621A1] Amide compounds (I) are new. Amide compounds of formula (I) are new. A : OH, 1-5C-alkoxy, hydroxy 1-5C-alkoxy, O-1-5C-alkyl-(O-1-4C-alkyl) n-O-1-4C-alkyl, N(1-5C-alkyl) 2, NH 2, N(H)-L, O-L or O-Z; G : OH, O-Z, O-1-5C-alkyl, O-2-5C-alkenyl, O-1-5C-alkyl-(O-1-4C-alkyl) nO-1-4C-alkyl, O-2-5C-alkynyl, or triphenylmethoxy; R 1>, R 2> : H, 1> 8>F-2-5C-alkoxy, 1> 8>F-1-5C-alkyl, 1> 8>F-2-5C-alkenyl, 1> 8>F-2-5C-alkynyl, OH, 1-5C-alkyl or 1-5C-alkoxy; L : 1-5C-alkyl, 2-5C-alkenyl, 1-5C-alkyl-(O-1-4C-alkyl) n-O-1-4C-alkyl or 2-5C-alkynyl; Z : a metal cation equivalent; and n : 0-3. Provided that one of the substituents R 1>or R 2>contains 1> 8>F isotope and the other substitution is free of 1> 8>F isotope and R 1>is not H. Independent claims are included for: (1) a carbonyl compound of formula (II); (2) the preparation of (I); (3) the preparation of (II) comprising reacting a carbonyl compound of formula (III) with F-18 fluoride; (4) the carbonyl compound (III); (5) use of a pyrrolidine compound of formula (IV) for the preparation of (I) or (II); (6) a kit comprising (III) or (IV); and (7) a pharmaceutical composition comprising (I)-(IV) and a suitable carrier. A 1> : OH, 1-5C-alkoxy, hydroxy 1-5C-alkoxy, O-1-5C-alkyl-(O-1-4C-alkyl) n-O-1-4C-alkyl, N(1-5C-alkyl) 2, NH 2, N(H)-L 1>, O-L 1>; G 1> : OH, O-Z 1>, O-1-5C-alkyl, O-2-5C-alkenyl, O-1-5C-alkyl-(O-1-4C-alkyl) nO-1-4C-alkyl, O-2-5C-alkynyl, or triphenylmethoxy; Q : N(H)-tert-butoxycarbonyl, N(H)-benzyloxycarbonyl, -N=C(X 1>)(X 2>) (all preferred), N(H)-allyloxycarbonyl, N(H)-ethoxycarbonyl, N(H)-methoxycarbonyl, N(H)-propoxycarbonyl, N(H)-2,2,2-trichloroethoxycarbonyl, N(H)-1,1-dimethylpropinyl, N(H)-1-methyl-1-phenyl-ethoxycarbonyl, N(H)-1-methyl-1-(4-biphenylyl)-ethoxycarbonyl, N(H)-cyclobutylcarbonyl, N(H)-cyclobutylcarbonyl, N(H)-1-methylcyclobutylcarbonyl, N(H)-vinylcarbonyl, N(H)-allylcarbonyl, N(H)-adamantylcarbonyl, N(H)-diphenylmethylcarbonyl, N(H)-cinnamylcarbonyl, N(H)-formyl, N(H)-benzoyl, N(H)-trityl, N(H)-p-methoxyphenyl-diphenylmethyl, N(H)-di-(p-methoxyphenyl)-phenylmethyl, or N-(tert.butyoxycarbonyl) 2; L 1>, L 2> : L; X 1>, X 2> : aryl, aralkyl or heteroaryl (all optionally substituted) or 1-5C-alkyl; Z 1>, Z 2> : a metal cation equivalent; A 2> : 1-5C-alkoxy, hydroxy 1-5C-alkoxy, O-1-5C-alkyl-(O-1-4C-alkyl) n-O-1-4C-alkyl, N(1-5C-alkyl) 2, NH 2, N(H)-U 1>, N(H)-L 2>or O-L 2>; G 2> : O-Z 2>, O-1-5C-alkyl, O-2-5C-alkenyl, O-1-5C-alkyl-(O-1-4C-alkyl) nO-1-4C-alkyl, O-2-5C-alkynyl, or triphenylmethoxy; R 3>, R 4> : H, E-2-5C-alkoxy, E-1-5C-alkyl, E-2-5C-alkenyl, E-2-5C-alkynyl, OH, 1-5C-alkyl, or 1-5C-alkoxy; E : Cl, Br, methanesulfonyloxy, trifluoromethanesulfonyloxy, nonafluorobutyloxy, tosyloxy or I; Q 1>, Q 3> : Q; G 3> : O-1-5C-alkyl, O-2-5C-alkenyl, O-1-5C-alkyl-(O-1-4C-alkyl) nO-1-4C-alkyl, O-2-5C-alkynyl, or triphenylmethoxy; R 5>, R 6> : H, OH, 1-5C-alkyl, 1-5C-alkoxy or R 7>-E 1>; E 1> : E; and R 7> : 2-5C-alkoxy, 1-5C-alkyl, 2-5C-alkenyl or 2-5C-alkynyl. Provided that: one of the substituent R 3>or R 4>contains E and the other substituent is free of E and R 3>is not H; and one of the substituents of R 5>or R 6>contains E 1>, and the other substituent is free of E 1>and R 5>is not H. [Image] [Image].
IPC 8 full level
C07B 59/00 (2006.01); A61K 31/04 (2006.01); A61K 31/195 (2006.01); A61K 51/04 (2006.01); C07C 229/24 (2006.01); C07C 237/06 (2006.01)
CPC (source: EP US)
A61K 49/0433 (2013.01 - US); A61K 51/0402 (2013.01 - EP US); A61P 35/00 (2017.12 - EP); A61P 43/00 (2017.12 - EP); C07B 59/001 (2013.01 - EP US); C07C 227/16 (2013.01 - US); C07C 229/24 (2013.01 - EP US); C07C 231/12 (2013.01 - US); C07C 237/06 (2013.01 - EP US); C07C 269/06 (2013.01 - US); C07C 271/22 (2013.01 - EP US); C07C 309/66 (2013.01 - US); C07D 207/16 (2013.01 - EP US); C07D 207/28 (2013.01 - EP US)
Citation (search report)
See references of WO 2009141091A1
Designated contracting state (EPC)
AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK TR
Designated extension state (EPC)
AL BA RS
DOCDB simple family (publication)
EP 2123621 A1 20091125; AR 073845 A1 20101209; AU 2009250130 A1 20091126; AU 2009250130 B2 20140821; BR PI0913128 A2 20160105; CA 2723596 A1 20091126; CA 2723596 C 20160802; CL 2009001240 A1 20100719; CN 102083772 A 20110601; CN 104356019 A 20150218; CO 6331330 A2 20111020; CR 11800 A 20110112; DO P2010000358 A 20101231; EA 025217 B1 20161230; EA 201001766 A1 20111230; EC SP10010617 A 20101230; EP 2282982 A1 20110216; HK 1205099 A1 20151211; IL 208662 A0 20101230; JP 2011520932 A 20110721; JP 2015042671 A 20150305; KR 101636245 B1 20160707; KR 20110009165 A 20110127; MX 2010012636 A 20101206; NZ 589350 A 20120831; PA 8827401 A1 20091216; PE 20091956 A1 20100205; SV 2010003739 A 20110406; TW 201008585 A 20100301; TW 201439043 A 20141016; US 2010290991 A1 20101118; US 2011165076 A1 20110707; US 2014154183 A1 20140605; US 9308282 B2 20160412; UY 31835 A 20100105; WO 2009141091 A1 20091126; WO 2009141091 A8 20101111
DOCDB simple family (application)
EP 08075510 A 20080520; AR P090101805 A 20090520; AU 2009250130 A 20090514; BR PI0913128 A 20090514; CA 2723596 A 20090514; CL 2009001240 A 20090520; CN 200980118538 A 20090514; CN 201410079216 A 20090514; CO 10145570 A 20101119; CR 11800 A 20101119; DO 2010000358 A 20101119; EA 201001766 A 20090514; EC SP10010617 A 20101119; EP 09749581 A 20090514; EP 2009003420 W 20090514; HK 15105833 A 20150618; IL 20866210 A 20101012; JP 2011509884 A 20090514; JP 2014222536 A 20141031; KR 20107025962 A 20090514; MX 2010012636 A 20090514; NZ 58935009 A 20090514; PA 8827401 A 20090520; PE 2009000704 A 20090520; SV 2010003739 A 20101119; TW 103123067 A 20090520; TW 98116758 A 20090520; US 201414173371 A 20140205; US 62210509 A 20091119; US 99349409 A 20090514; UY 31835 A 20090520