[F-18]-LABELED L-GLUTAMIC ACID, [F-18]-LABELED L-GLUTAMINE, DERIVATIVES THEREOF AND USE THEREOF AND PROCESSES FOR THEIR PREPARATION
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.
1 ) A compound of the general formula I
wherein
A represents
a) hydroxyl,
b) branched or unbranched C 1 -C 5 alkoxy,
c) branched or unbranched hydroxy C 1 -C 5 alkoxy,
d) branched or unbranched O—C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -O—C 1 -C 4 alkyl,
e) N(C 1 -C 5 alkyl) 2 ,
f) NH 2 ,
g) N(H)-L,
h) O-L or
i) O—Z,
G represents
a) hydroxyl,
b) O—Z
b) branched or unbranched O—C 1 -C 5 alkyl,
c) branched or unbranched O—C 2 -C 5 alkenyl,
d) branched or unbranched O—C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -O—C 1 -C 4 alkyl or
e) branched or unbranched O—C 2 -C 5 alkynyl,
R 1 and R 2 represent
a) hydrogen,
b) 18 F,
c) branched or unbranched 18 F—C 1 -C 5 alkoxy,
d) branched or unbranched 18 F—C 1 -C 5 alkyl,
e) branched or unbranched 18 F-hydroxy-C 1 -C 5 alkyl,
f) branched or unbranched 18 F-C 2 -C 5 alkenyl, or
g) branched or unbranched 18 F-C 2 -C 5 alkynyl,
h) hydroxyl,
i) branched or unbranched C 1 -C 5 alkyl or
j) branched or unbranched C 1 -C 5 alkoxy,
with the proviso that one of the substituents R 1 or R 2 contains exactly one 18 F isotope and the other substituent in each case contains no 18 F isotope,
L represents
a) branched or unbranched C 1 -C 5 alkyl,
b) branched or unbranched C 2 -C 5 alkenyl,
c) branched or unbranched C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -O—C 1 -C 4 alkyl or
d) branched or unbranched C 2 -C 5 alkynyl,
and
Z represents a metal cation equivalent,
where
n is =0, 1, 2 or 3 and
diastereomers and enantiomers.
2 ) A compound as claimed in claim 1 , characterized in that A represents OH, methoxy or NH 2 .
3 ) A compound as claimed in claim 1 , characterized in that A represents OH.
4 ) A compound as claimed in claim 1 , characterized in that A represents NH 2 .
5 ) A compound as claimed in claim 1 , characterized in that R 1 and R 2 are selected from the group consisting of hydrogen, 18 F, 18 F-methoxy, 18 F-ethoxy, 18 F-propoxy, 18 F-methyl, 18 F-ethyl and 18 F-propyl, with the proviso that one of the substituents R 1 or R 2 contains exactly one 18 F isotope and the other substituent in each case is hydrogen.
6 ) A compound as claimed in claim 1 , characterized in that R 1 is selected from the group consisting of hydroxyl, CH 3 , C 2 H 5 and C 3 H 7 , and R 2 represents 18 F.
7 ) A compound as claimed in claim 1 , characterized in that R 2 is selected from the group consisting of hydroxyl, CH 3 , C 2 H 5 and C 3 H 7 , and R 1 represents 18 F.
8 ) A compound as claimed in claim 1 , characterized in that R 1 represents 18 F and R 2 represents hydrogen.
9 ) A compound as claimed in claim 1 , characterized in that R 2 represents 18 F and R 1 represents hydrogen.
10 ) A compound as claimed in claim 1 , characterized in that G is selected from the group consisting of OH, methoxy or ethoxy.
11 ) A compound as claimed in claim 1 , characterized in that Z is selected from the group consisting of Mg 2+ , Ca 2+ , Na + and K + .
12 ) A compound as claimed in claim 1 , characterized in that A is Ni 2+ .
13 ) A compound as claimed in claim 1 selected from the group consisting of compounds having the formula:
14 ) A compound of the general formula (II):
wherein
A′ represents
a) hydroxyl,
b) branched or unbranched C 1 -C 5 alkoxy,
c) branched or unbranched hydroxy C 1 -C 5 alkoxy,
d) branched or unbranched O—C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -O—C 1 -C 4 alkyl,
e) N(C 1 -C 5 alkyl) 2 ,
f) NH 2 ,
g) N(H)—U,
h) N(H)-L′, or
i) O-L,
G′ represents
a) hydroxyl,
b) O—Z′,
c) branched or unbranched O—C 1 -C 5 alkyl,
d) branched or unbranched O—C 2 -C 5 alkenyl,
e) branched or unbranched O—C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -O—C 1 -C 4 alkyl or
f) branched or unbranched O—C 2 -C 5 alkynyl,
R 1 and R 2 represent
a) hydrogen,
b) 18 F,
c) branched or unbranched 18 F—C 1 -C 5 alkoxy,
d) branched or unbranched 18 F—C 1 -C 5 alkyl,
e) branched or unbranched 18 F-hydroxy-C 1 -C 5 hydroxyalkyl,
f) branched or unbranched 18 F-C 2 -C 5 alkenyl,
g) branched or unbranched 18 F-C 2 -C 5 alkynyl,
h) hydroxyl,
i) branched or unbranched C 1 -C 5 alkyl, or
j) branched or unbranched C 1 -C 5 alkoxy,
with the proviso that one of the substituents R 1 or R 2 contains exactly one 18 F isotope and the other substituent in each case contains no 18 F isotope,
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,
e) N(H)-2,2,2-trichloroethoxycarbonyl,
f) N(H)-1,1-dimethylpropynyl,
g) N(H)-1-methyl-1-phenylethoxycarbonyl,
h) N(H)-1-methyl-1-(4-biphenylyl)ethoxycarbonyl,
i) N(H)-cyclobutylcarbonyl,
j) N(H)-1-methylcyclobutylcarbonyl,
k) N(H)-vinylcarbonyl,
l) N(H)-allylcarbonyl,
m) N(H)-adamantylcarbonyl,
n) N(H)-diphenylmethylcarbonyl,
o) N(H)-cinnamylcarbonyl,
p) N(H)-formyl,
q) N(H)-benzoyl,
r) N(H)-trityl,
s) N(H)-p-methoxyphenyldiphenylmethyl,
t) N(H)-di(p-methoxyphenyl)phenylmethyl,
v) N-(tert-butoxycarbonyl) 2 ,
L′ represents
a) branched or unbranched C 1 -C 5 alkyl,
b) branched or unbranched C 2 -C 5 alkenyl,
c) branched or unbranched C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -O—C 1 -C 4 alkyl, or
d) branched or unbranched C 2 -C 5 alkynyl,
U represents
a) tert-butoxycarbonyl,
b) allyloxycarbonyl,
c) benzyloxycarbonyl,
d) ethoxycarbonyl,
e) methoxycarbonyl, or
f) propoxycarbonyl,
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,
and
Z′ represents a metal cation equivalent,
where n is =0, 1, 2 or 3 and
diastereomers and enantiomers.
15 ) A compound as claimed in claim 14 , characterized in that A′ represents OH, branched or unbranched C 1 -C 5 alkoxy, —NH-tert-butoxycarbonyl or NH 2 .
16 ) A compound as claimed in claim 14 , characterized in that A′ represents ethoxy.
17 ) A compound as claimed in claim 14 , characterized in that A′ represents NH 2 .
18 ) A compound as claimed in claim 14 , characterized in that R 1 and R 2 are selected from the group consisting of hydrogen, 18 F, 18 F-methoxy, 18 F-ethoxy, 18 F-propoxy, 18 F-methyl, 18 F-ethyl and 18 F-propyl, with the proviso that one of the substituents R 1 or R 2 contains exactly one 18 F isotope and the other substituent in each case is hydrogen.
19 ) A compound as claimed in claim 14 , characterized in that R 1 is selected from the group consisting of hydroxyl, CH 3 , C 2 H 5 and C 3 H 7 , and R 2 represents 18 F.
20 ) A compound as claimed in claim 14 , characterized in that R 2 is selected from the group consisting of hydroxyl, CH 3 , C 2 H 5 and C 3 H 7 , and R 1 represents 18 F.
21 ) A compound as claimed in claim 14 , characterized in that R 1 represents 18 F and R 2 represents hydrogen.
22 ) A compound as claimed in claim 14 , characterized in that R 2 represents 18 F and R 1 represents hydrogen.
23 ) A compound as claimed in claim 14 , characterized in that G′ is selected from the group consisting of OH, ethoxy, methoxy and OZ′.
24 ) A compound as claimed in claim 14 , characterized in that G′ represents ethoxy.
25 ) A compound as claimed in claim 14 , characterized in that Z′ is selected from the group consisting of Na + , K + , Ca 2+ and Mg 2+ .
26 ) A compound as claimed in claim 14 , characterized in that Z′ is Ni 2+ .
27 ) A compound as claimed in claim 14 , characterized in that Q is selected from the group consisting of N(H)-tert-butoxycarbonyl, N(H)-benzyloxycarbonyl and
wherein
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.
28 ) A compound as claimed in claim 14 , characterized in that Q represents N(H)-tert-butoxycarbonyl.
29 ) A compound as claimed in claim 14 , characterized in that Q represents
30 ) A compound as claimed in claim 14 selected from the group consisting of compounds having the formula:
31 ) A process for the preparation of compounds of the general formula (I) as claimed in claim 1
by
reacting a precursor compound of the compound as set forth in formula (II)
wherein
A′ represents
a) hydroxyl,
b) branched or unbranched C 1 -C 5 alkoxy,
c) branched or unbranched hydroxy C 1 -C 5 alkoxy,
d) branched or unbranched O—C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -C 1 -C 4 alkyl,
e) N(C 1 -C 5 alkyl) 2 .
f) NH 2 ,
g) N(H)—U,
h) N(H)-L′, or
i) O-L′,
G′ represents
a) hydroxyl,
b) O—Z′,
c) branched or unbranched O—C 1 -C 5 alkyl,
d) branched or unbranched O—C 2 -C 5 alkenyl,
e) branched or unbranched O—C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -C 1 -C 4 alkyl, or
f) branched or unbranched O—C 2 -C 5 alkynyl,
R 1 and R 2 represent
a) hydrogen,
k) 18 F,
l) branched or unbranched 18 F—C 1 -C 5 alkoxy,
m) branched or unbranched 18 F—C 1 -C 5 alkyl,
n) branched or unbranched 18 F—C 1 -C 5 -hydroxyalkyl,
o) branched or unbranched 18 F—C 2 -C 5 alkenyl,
p) branched or unbranched 18 F—C 2 -C 5 alkynyl,
q) hydroxyl,
r) branched or unbranched C 1 -C 5 alkyl, or
s) branched or unbranched C 1 -C 5 alkoxy,
with the proviso that exactly one of the substituents R 1 or R 2 contains exactly one 18 F isotope and the other substituent in each case contains no 18 F isotope,
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,
e) N(H)-2,2,2-trichloroethoxycarbonyl,
f) N(H)-1,1-dimethylpropynyl,
g) N(H)-1-methyl-1-phenylethoxycarbonyl,
h) N(H)-1-methyl-1-(4-biphenylyl)ethoxycarbonyl,
i) N(H)-cyclobutylcarbonyl,
j) N(H)-1-methylcyclobutylcarbonyl,
k) N(H)-vinylcarbonyl,
l) N(H)-allylcarbonyl,
m) N(H)-adamantylcarbonyl,
n) N(H)-diphenylmethylcarbonyl,
o) N(H)-cinnamylcarbonyl,
p) N(H)-formyl,
q) N(H)-benzoyl,
r) N(H)-trityl,
s) N(H)-p-methoxyphenyldiphenylmethyl,
t) N(H)-di(p-methoxyphenyl)phenylmethyl,
v) N-(tert-butoxycarbonyl) 2 .
L′ represents
a) branched or unbranched C 1 -C 5 alkyl,
b) branched or unbranched C 2 -C 5 alkenyl,
c) branched or unbranched C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -C 1 -C 4 alkyl, or
d) branched or unbranched C 2 -C 5 alkynyl,
U represents
a) tert-butoxycarbonyl,
b) allyloxycarbonyl,
c) benzyloxycarbonyl,
d) ethoxycarbonyl,
e) methoxycarbonyl or
f) propoxycarbonyl,
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,
and
Z′ represents a metal cation equivalent,
where n is =0, 1, 2 or 3 and
diastereomers and enantiomers
and F-18 fluoride.
32 ) A process for the preparation of compounds of the general formula (II) as claimed in claim 14
by
reacting a precursor compound of the compound as set forth in formula (III)
wherein
A″ represents
a) hydroxyl,
b) branched or unbranched C 1 -C 5 alkoxy,
c) branched or unbranched hydroxy C 1 -C 5 alkoxy,
d) branched or unbranched O—C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -C 1 -C 4 alkyl,
e) N(C 1 -C 5 alkyl) 2 .
f) NH 2 ,
g) N(H)—U′,
h) N(H)-L″ or
i) O-L″,
G″ represents
a) hydroxyl,
b) O—Z″,
c) branched or unbranched O—C 1 -C 5 alkyl,
d) branched or unbranched O—C 2 -C 5 alkenyl,
e) branched or unbranched O—C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -C 1 -C 4 alkyl,
f) branched or unbranched O—C 2 -C 5 alkynyl, or
g) triphenylmethoxy,
R 3 and R 4 represent
a) hydrogen,
b) branched or unbranched E-C 1 -C 5 alkoxy,
c) branched or unbranched E-C 1 -C 5 alkyl,
d) branched or unbranched E-hydroxy-C 1 -C 5 -alkyl,
e) branched or unbranched E-C 2 -C 5 alkenyl,
f) branched or unbranched E-C 2 -C 5 alkynyl,
g) hydroxyl,
h) branched or unbranched C 1 -C 5 alkyl, or
i) branched or unbranched C 1 -C 5 alkoxy,
with the proviso that exactly one of the substituents R 3 or R 4 contains an E and the other substituent in each case contains no E,
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,
x) N-(tert-butoxycarbonyl) 2 ,
L″ represents
a) branched or unbranched C 1 -C 5 alkyl,
b) branched or unbranched C 2 -C 5 alkenyl,
c) branched or unbranched C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -C 1 -C 4 alkyl or
d) branched or unbranched C 2 -C 5 alkynyl,
U′ represents
a) tert-butoxycarbonyl,
b) allyloxycarbonyl,
c) benzyloxycarbonyl, or
d) ethoxycarbonyl,
X′ and X″ independently of one another represent
a) branched or unbranched C 1 -C 5 alkyl,
b) substituted or unsubstituted aryl,
c) alkylaryl or
d) heteroaryl,
and
Z″ represents a metal cation equivalent,
where n is =0, 1 or 2 and
diastereomers and enantiomers and F-18 fluoride.
33 ) A compound as claimed in claim 1 for use as a medicament.
34 ) A compound as claimed in claim 1 for use in the diagnosis of tumors.
35 ) A method of using the compounds as claimed in claim 1 comprising producing a medicament for the diagnosis of tumors.
36 ) A compound of the formula (III)
wherein
A″ represents
a) hydroxyl,
b) branched or unbranched C 1 -C 5 alkoxy,
c) branched or unbranched hydroxy C 1 -C 5 alkoxy,
d) branched or unbranched O—C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -O—C 1 -C 4 alkyl,
e) N(C 1 -C 5 alkyl) 2 ,
f) NH 2 ,
g) N(H)—U′,
h) N(H)-L″ or
i) O-L″,
G″ represents
a) hydroxyl,
b) O—Z″,
c) branched or unbranched O—C 1 -C 5 alkyl,
d) branched or unbranched O—C 2 -C 5 alkenyl,
e) branched or unbranched O—C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -O—C 1 -C 4 alkyl,
f) branched or unbranched O—C 2 -C 5 alkynyl, or
g) triphenylmethoxy,
R 3 and R 4 represent
a) hydrogen,
b) branched or unbranched E-C 1 -C 5 alkoxy,
c) branched or unbranched E-C 1 -C 5 alkyl,
d) branched or unbranched E-hydroxy-C 1 -C 5 -alkyl,
e) branched or unbranched E-C 2 -C 5 alkenyl,
f) branched or unbranched E-C 2 -C 5 alkynyl,
g) hydroxyl,
h) branched or unbranched C 1 -C 5 alkyl, or
i) branched or unbranched C 1 -C 5 alkoxy,
with the proviso that exactly one of the substituents R 3 or R 4 contains an E and the other substituent in each case contains no E,
E represents
a) chloro,
b) bromo,
c) mesyloxy,
d) trifluoromesyloxy,
e) nonafluorobutyloxy, or
0 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,
x) N-(tert-butoxycarbonyl) 2 ,
L″ represents
a) branched or unbranched C 1 -C 5 alkyl,
b) branched or unbranched C 2 -C 5 alkenyl,
c) branched or unbranched C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -O—C 1 -C 4 alkyl or
d) branched or unbranched C 2 -C 5 alkynyl,
U′ represents
a) tert-butoxycarbonyl,
b) allyloxycarbonyl,
c) benzyloxycarbonyl, or
d) ethoxycarbonyl,
X′ and X″ independently of one another represent
a) branched or unbranched C 1 -C 5 alkyl,
b) substituted or unsubstituted aryl,
c) alkylaryl or
d) heteroaryl,
and
Z″ represents a metal cation equivalent,
where n is =0, 1 or 2 and
diastereomers and enantiomers.
37 ) A method of using the compounds of the formula (IV) comprising preparing compounds of the formula (I) or (II):
wherein
A′″ represents
a) hydroxyl,
b) branched or unbranched C 1 -C 5 alkoxy,
c) branched or unbranched hydroxy C 1 -C 5 alkoxy,
d) branched or unbranched O—C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -O—C 1 -C 4 alkyl,
e) N(C 1 -C 5 alkyl) 2 ,
f) NH 2 ,
g) N(H)—U″,
h) N(H)-L′″ or
i) O-L′″,
G″ represents
a) hydroxyl,
b) branched or unbranched O—C 1 -C 5 alkyl,
c) branched or unbranched O—C 2 -C 5 alkenyl,
d) branched or unbranched O—C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -O—C 1 -C 4 alkyl,
e) branched or unbranched O—C 2 -C 5 alkynyl, or
f) triphenylmethoxy,
R 5 and R 6 represent
a) hydrogen or
b) E′,
with the proviso that exactly one of the substituents R 5 or R 6 contains E′ and the other substituent in each case contains hydrogen,
E′ represents
a) chloro,
b) bromo,
c) mesyloxy,
d) trifluoromesyloxy,
e) nonafluorobutyloxy or
tosyloxy,
Q″ represents
a) N(H)-tert-butoxycarbonyl,
b) N(H)-allyloxycarbonyl,
c) N(H)-benzyloxycarbonyl,
d) N(H)-ethoxycarbonyl,
e) N(H)-methoxycarbonyl,
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,
x) N-(tert-butoxycarbonyl) 2 ,
L′″ represents
a) branched or unbranched C 1 -C 5 alkyl,
b) branched or unbranched C 2 -C 5 alkenyl,
c) branched or unbranched C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -O—C 1 -C 4 alkyl, or
d) branched or unbranched C 2 -C 5 alkynyl,
U″ represents
a) tert-butoxycarbonyl,
b) allyloxycarbonyl,
c) benzyloxycarbonyl, or
d) ethoxycarbonyl,
X″ and X′″ independently of one another represent
a) branched or unbranched C 1 -C 5 alkyl,
b) substituted or unsubstituted aryl,
c) alkylaryl, or
d) heteroaryl,
where n is =0, 1 or 2 and
diastereomers and enantiomers.
38 ) A method of using the compounds of the formula (V) for the preparation of compounds of the formula (I) or (II):
wherein
G′″ represents
a) hydroxyl,
b) branched or unbranched O—C 1 -C 5 alkyl,
c) branched or unbranched O—C 2 -C 5 alkenyl,
d) branched or unbranched O—C 1 -C 5 alkyl-(O—C 1 -C 4 alkyl) n -O—C 1 -C 4 alkyl,
e) branched or unbranched O—C 2 -C 5 alkynyl, or
f) triphenylmethoxy,
R 5 and R 6 represent
c) hydrogen or
d) E′,
with the proviso that exactly one of the substituents R 5 or R 6 contains an E and the other substituent in each case contains no E,
E′ represents
a) chloro,
b) bromo,
c) mesyloxy,
d) trifluoromesyloxy,
e) nonafluorobutyloxy or
f) tosyloxy,
Q′″ represents
a) N-tert-butoxycarbonyl,
b) N-allyloxycarbonyl,
c) N-benzyloxycarbonyl,
d) N-ethoxycarbonyl,
e) N-methoxycarbonyl,
f) N-propoxycarbonyl,
g) N-2,2,2-trichloroethoxycarbonyl,
h) hydrogen,
i) N-1-methyl-1-phenylethoxycarbonyl,
j) N-1-methyl-1-(4-biphenylyl)ethoxycarbonyl,
k) N-cyclobutylcarbonyl,
l) N-1-methylcyclobutylcarbonyl,
m) N-vinylcarbonyl,
n) N-allylcarbonyl,
o) N-adamantylcarbonyl,
p) N-diphenylmethylcarbonyl,
q) N-cinnamylcarbonyl,
r) N-formyl, or
s) N-benzoyl,
where n is =0, 1, 2 or 3 and all possible diastereomers and enantiomers.
39 ) A compound as claimed in claim 1 , characterized in that the compounds are suitable for PET diagnostics in a dose range of 37-600 MBq.
40 ) A compound as claimed in claim 39 , characterized in that the compounds are particularly suitable in a dose range of 150 MBq-370 MBq.