IP Library Granted Patent US 9,375,497
Granted Patent B2
US 9,375,497 · App. 14/153,491 · Granted Jun 28, 2016

[F-18]-labeled L-glutamic acid, [F-18]-labeled L-glutamine, derivatives thereof and use thereof and processes for their preparation

Inventors: Ludger Dinkelborg (Berlin, DE); Matthias Friebe (Berlin, DE); Nikolaevna Raisa Krasikowa (St. Petersburg, RU); Yuri Belokon (Moscow, RU); Fedorovna Olga Kuznetsova (St. Petersburg, RU); Keith Graham (Berlin, DE); Lutz Lehmann (Wuppertal, DE); Mathias Berndt (Berlin, DE)
Assignee: PIRAMAL IMAGING SA
A61K51/0402C07B59/001C07C227/16C07C229/24C07C251/24C07C271/22C07C309/66C07C309/73C07D207/16C07D207/26C07D207/28C07F15/045C07B2200/05
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Quick Facts
Patent No.
US 9,375,497
App. No.
14/153,491
Granted
Jun 28, 2016
Kind
B2
Abstract

The compounds and the synthesis of [F-18]-labeled L-glutamic acid, [F-18]-labeled L-glutamate, their derivatives as set forth in formula (I) and their uses are described.

Claims (54)

1. A compound of the formula:

2. A process for the preparation of compounds of claim 1 , comprising

reacting a precursor compound of the formula (II)

Wherein

A′ represents hydroxyl, or NH 2 ,

G′ represents hydroxyl,

R 2 represents hydrogen,

R 1 represents unbranched E-C 1 or E-C 3 alkyl, or

unbranched E-C 2 -C 3 alkoxy,

E represents

a) chloro,

b) bromo,

c) mesyloxy,

d) trifluoromesyloxy,

e) nonafluorobutyloxy, or

f) tosyloxy,

Q represents

a) N(H)-tert-butoxycarbonyl,

b) N(H)-allyloxycarbonyl,

c) N(H)-benzyloxycarbonyl,

d) N(H)-ethoxycarbonyl,

e) N(H)-methoxycarbonyl,

f) N(H)-propoxycarbonyl,

g) N(H)-2,2,2-trichloroethoxycarbonyl,

h) N(H)-1,1-dimethylpropynyl,

i) N(H)-1-methyl-1-phenylethoxycarbonyl,

j) N(H)-1-methyl-1-(4-biphenylyl)ethoxycarbonyl,

k) N(H)-cyclobutylcarbonyl,

l) N(H)-1-methylcyclobutylcarbonyl,

m) N(H)-vinylcarbonyl,

n) N(H)-allylcarbonyl,

o) N(H)-adamantylcarbonyl,

p) N(H)-diphenylmethylcarbonyl,

q) N(H)-cinnamylcarbonyl,

r) N(H)-formyl,

s) N(H)-benzoyl,

t) N(H)-trityl,

u) N(H)-p-methoxyphenyldiphenylmethyl,

v) N(H)-di(p-methoxyphenyl)phenylmethyl,

w)

or

x) N-(tert-butoxycarbonyl) 2 ,

X′ and X″ independently of one another represent

a) branched or unbranched C 1 -C 5 alkyl,

b) substituted or unsubstituted aryl or

c) aralkyl,

or diastereomers or enantiomers thereof,

with a F-18 fluoride.

3. A method for the diagnosis of tumors, comprising imaging a patient to whom a compound according to claim 1 has been administered.

4. A compound as claimed in claim 1 , that is suitable for PET diagnostics in a dose range of 37-600 MBq.

5. A compound as claimed in claim 4 , that is suitable in a dose range of 150 MBq-370 MBq.

6. The compound according to claim 1 , of the formula:

7. The compound according to claim 1 , of the formula:

8. The compound according to claim 1 , of the formula:

Assignments (2)
CHANGE OF NAME Recorded May 22, 2019
From: PIRAMAL IMAGING SA
To: LIFE MOLECULAR IMAGING SA
Reel/Frame 049252/0547 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2016
From: DINKELBORG, LUDGER; FRIEBE, MATTHIAS; KRASIKOWA, RAISA NIKOLAEVNA; BELOKON, YURI; KUZNETSOVA, OLGA FEDOROVNA; GRAHAM, KEITH; LEHMANN, LUTZ; BERNDT, MATHIAS
To: PIRAMAL IMAGING SA
Reel/Frame 038698/0280 →
Priority Claims (2)
RU 2006138584 · Nov 1, 2006 · national
EP 06090211 · Nov 18, 2006 · regional
Continuity (2)
Continuation 12513112
Related Publication 20140301948A1 · Oct 9, 2014