IP Library Granted Patent US 9,308,282
Granted Patent B2
US 9,308,282 · App. 14/173,371 · Granted Apr 12, 2016

[F-18]-labelled L-glutamic acid and L-glutamine derivatives (I), their use and processes for their preparation

Inventors: Matthias Friebe (Berlin, DE); Heribert Schmitt-Willich (Berlin, DE); Matthias Berndt (Berlin, DE); Ludger Dinkelborg (Berlin, DE); Norman Koglin (Berlin, DE); Keith Graham (Berlin, DE)
Assignee: PIRAMAL IMAGING SA
A61K49/0433A61K51/0402C07B59/001C07C227/16C07C229/24C07C231/12C07C237/06C07C269/06C07C271/22C07C309/66C07D207/16C07D207/28
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Quick Facts
Patent No.
US 9,308,282
App. No.
14/173,371
Granted
Apr 12, 2016
Kind
B2
Abstract

What is described are the compounds and the synthesis of [F-18]-labelled L-glutamic acid, [F-18]-labelled L-glutamate, their derivatives of the formula (I) and their use.

Claims (39)

1. A compound of the formula:

2. A process for preparing the compound according to claim 1 , said process comprising:

removing one or more protective groups present in a compound of the formula (II)

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-methoxydiphenylmethyl,

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

or

x) N-(tert-butoxycarbonyl) 2 ,

in which

X′ and X″ independently of one another represent

a) branched or straight-chain C 1 -C 5 alkyl,

b) substituted or unsubstituted aryl,

c) substituted or unsubstituted aralkyl or

d) substituted or unsubstituted heteroaryl.

3. A method of imaging a patient for tumor disorders comprising imaging a patient who has been administered a compound according to claim 1 .

4. An imaging kit, comprising a compound according to claim 1 .

5. A pharmaceutical composition, comprising a compound according to claim 1 and a suitable pharmaceutical carrier substance.

6. A compound according to claim 1 , suitable for imaging in a dosage range of 37-600 MBq.

7. The compound according to claim 6 , suitable for imaging in a dosage range of 150 MBq-370 MBq.

Assignments (4)
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 Jan 20, 2016
From: FRIEBE, MATTHIAS; SCHMITT-WILLICH, HERIBERT; BERNDT, MATTHIAS; DINKELBORG, LUDGER; KOGLIN, NORMAN; GRAHAM, KEITH
To: BAYER SCHERING PHARMA AG
Reel/Frame 037531/0288 →
CHANGE OF NAME Recorded Jan 20, 2016
From: BAYER SCHERING PHARMA AKTIENGESELLSCHAFT
To: BAYER PHARMA AKTIENGESELLSCHAFT
Reel/Frame 037564/0693 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 20, 2016
From: BAYER PHARMA AKTIENGESELLSCHAFT
To: PIRAMAL IMAGING SA
Reel/Frame 037564/0745 →
Priority Claims (1)
EP 08075510 · May 20, 2008 · regional
Continuity (3)
Continuation 12622105 · Nov 19, 2009
Continuation In Part PCTEP2009003420 · May 14, 2009
Related Publication 20140154183A1 · Jun 5, 2014