Novel [f-18]-labelled l-glutamic acid and l-glutamine derivatives (i), their use and processes for their preparation

4) Compounds of the general formula (II):

• in which
• A′ represents
• a) hydroxyl,
• b) branched or straight-chain C1-C5 alkoxy,
• c) branched or straight-chain hydroxy C1-C5 alkoxy,
• d) branched or straight-chain O—C1-C5 alkyl-(O—C1-C4 alkyl)n-O—C1-C4 alkyl,
• e) N(C1-C5 alkyl)2,
• f) NH2,
• g) N(H)-L′,
• h) O-L′,
• G′ represents
• a) hydroxyl,
• b) O—Z′,
• c) branched or straight-chain O—C1-C5 alkyl,
• d) branched or straight-chain O—C2-C5 alkenyl,
• e) branched or straight-chain O-C1-C5 alkyl-(O—C1-C4 alkyl)n-O—C1-C4 alkyl,
• f) branched or straight-chain O—C2-C5 alkynyl or
• g) triphenylmethoxy,
• R1 and R2 represent
• a) hydrogen,
• b) branched or straight-chain 18F—C1-C5 alkoxy,
• c) branched or straight-chain 18F—C1-C5 alkyl,
• d) branched or straight-chain 18F—C2-C5 alkenyl,
• e) branched or straight-chain 18F—C2-C5 alkynyl,
• f) hydroxyl,
• g) branched or straight-chain C1-C5 alkyl or
• h) branched or straight-chain C1-C5 alkoxy,
• alkyl being optionally interrupted by one or more O, S or N,
• with the proviso that exactly one of the substituents R1 or R2 contains exactly one 18F isotope and the respective other substituent contains no 18F isotope, with the proviso that R1 is not hydrogen,
• 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-methoxydiphenylmethyl,
• t) N(H)-di(p-methoxyphenyl)phenylmethyl,
• or
• v) N-(tert-butoxycarbonyl)2,
• L′ represents
• a) branched or straight-chain C1-C5 alkyl,
• b) branched or straight-chain C2-C5 alkenyl,
• c) branched or straight-chain C1-C5 alkyl-(O—C1-C4 alkyl)n-O—C1-C4 alkyl or
• d) branched or straight-chain C2-C5 alkynyl,
• X′ and X″ independently of one another represent
• a) branched or straight-chain C1-C5 alkyl,
• b) substituted or unsubstituted aryl,
• c) substituted or unsubstituted aralkyl or
• d) substituted or unsubstituted heteroaryl,
• Z′ represents a metal cation equivalent, and
• where n=0, 1, 2 or 3.

12) Compounds of the formula (III)

• in which
• A″ represents
• a) branched or straight-chain C1-C5 alkoxy,
• b) branched or straight-chain hydroxy C1-C5 alkoxy,
• c) branched or straight-chain O—C1-C5 alkyl-(O—C1-C4 alkyl)n-O—C1-C4 alkyl,
• d) N(C1-C5 alkyl)2,
• e) NH2,
• f) N(H)—U′
• g) N(H)-L″, or
• h) O-L″,
• G″ represents
• a) O—Z″,
• b) branched or straight-chain O—C1-C5 alkyl,
• c) branched or straight-chain O—C2-C5 alkenyl,
• d) branched or straight-chain O—C1-C5 alkyl-(O—C1-C4 alkyl)n-O—C1-C4 alkyl,
• e) branched or straight-chain O—C2-C5 alkynyl or
• f) triphenylmethoxy,
• R3 and R4 represent
• a) hydrogen,
• b) branched or straight-chain E-C1-C5 alkoxy,
• c) branched or straight-chain E-C1-C5 alkyl,
• d) branched or straight-chain E-C2-C5 alkenyl,
• e) branched or straight-chain E-C2-C5 alkynyl,
• f) hydroxyl,
• g) branched or straight-chain C1-C5 alkyl or
• h) branched or straight-chain C1-C5 alkoxy,
• alkyl being optionally interrupted by one or more O, S or N, with the proviso that exactly one of the substituents R3 or R4 contains an E and the respective other substituent contains no E, with the proviso that R3 is not hydrogen,
• E represents a leaving group,
• 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,
• L″ represents
• a) branched or straight-chain C1-C5 alkyl,
• b) branched or straight-chain C2-C5 alkenyl,
• c) branched or straight-chain C1-C5 alkyl-(O—C1-C4 alkyl)n-O—C1-C4 alkyl or
• d) branched or straight-chain C2-C5 alkynyl,
• X′ and X″ independently of one another represent
• a) branched or straight-chain C1-C5 alkyl,
• b) substituted or unsubstituted aryl,
• c) substituted or unsubstituted alkylaryl or
• d) substituted or unsubstituted heteroaryl,
• Z″ represents a metal cation equivalent, and
• where n=0, 1, 2 or 3.

13) Use of compounds of the formula (IV) for preparing compounds of the formula (I) or (II):

• in which
• G″′ represents
• a) branched or straight-chain O—C1-C5 alkyl,
• b) branched or straight-chain O—C2-C5 alkenyl,
• c) branched or straight-chain O—C1-C5 alkyl-(O—C1-C4 alkyl)n-O—C1-C4 alkyl,
• d) branched or straight-chain O—C2-C5 alkynyl or
• e) triphenylmethoxy,
• R5 and R6 represent
• a) hydrogen,
• b) hydroxyl,
• c) branched or straight-chain C1-C5 alkyl,
• d) branched or straight-chain C1-C5 alkoxy or
• e) R7-E′,
• with the proviso that exactly one of the substituents R5 or R6 contains an E′ and the respective other substituent contains no E′, with the proviso that R5 is not hydrogen,
• E′ represents a leaving group,
• R7 represents
• a) branched or straight-chain C1-C5 alkoxy,
• b) branched or straight-chain C1-C5 alkyl,
• c) branched or straight-chain C2-C5 alkenyl or
• d) branched or straight-chain C2-C5 alkynyl,
• 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,
• s) N-benzoyl,
• t) N(H)-trityl,
• u) N(H)-p-methoxyphenyldiphenylmethyl,
• v) N(H)-di(p-methoxyphenyl)phenylmethyl,
• or
• x) N-(tert-butoxycarbonyl)2,
• X′ and X″ independently of one another represent
• a) branched or straight-chain C1-C5 alkyl,
• b) substituted or unsubstituted aryl,
• c) substituted or unsubstituted alkylaryl or
• d) substituted or unsubstituted heteroaryl, and
• where n=0, 1, 2 or 3.