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US 7,115,249 B2Granted
Solid-phase electrophilic fluorination
AssigneesGe Healthcare Limited, Hammersmith Imanet Limited
InventorsSajinder Kaur Luthra, Frank Brady, Harry John Wadsworth
Life of this patent
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Abstract
The invention relates to compounds of formula (I); wherein R1 and R2 independently selected from C1-6 alkyl; P1, P2, P3, and P4 are each independently hydrogen or a protecting group; and their use in the preparation of 18F-labelled 6-L-fluorodopa
Claims13
A process for the production of 6-L-18F-fluorodopa (18F-FDOPA) which comprises treatment of a solid support-bound FDOPA precursor of formula (I):
- wherein R1 and R2 independently selected from C1-6 alkyl;
- P1, P2, P3, and P4 are each independently hydrogen or a protecting group;
- with a source of 18F selected from the group consisting of 18F2, 18F—CH3COOF and 18F—OF2;
- to give the labelled tracer of formula (II)
- wherein P1, P2, P3, and P4 are each independently hydrogen or a protecting group;
- optionally followed by:
- (i) removal of excess fluorinating agent and 18F− ions produced in the generation of the fluorinating agent or in the reaction of a compound of formula (I) with a source of 18F;
- and/or
- (ii) removal of any protecting groups;
- and/or
- (iii) removal of organic solvent;
- and/or
- (iv) formulation of the resultant compound of formula (II) as an aqueous solution.
10 more elements
A process for the preparation of a compound of formula (V)
- wherein R1 and R2 are independently C1-6 alkyl, and phenyl ring “A” is optionally substituted with 1 to 5 organic groups selected from the group consisting of (a) halo, cyano, hydroxy, C1-6 alkoxy, C1-6 carboxylic acid or ester, an amine or amide group;
- and (b) saturated or unsaturated straight or branched chain, or cyclic systems comprising from 1 to 12 carbon atoms and 0 to 4 heteroatoms each of which may be optionally substituted by the groups listed in (a);
- which comprises:
- reaction of a compound of formula (III)
- wherein either:
- R1, R2, R3, R4, and R5 are each independently selected from C1-6 alkyl;
- or
- R1, R2, R3, and R5 are each independently selected from C1-6 alkyl and R4 is
- with the corresponding compound of formula (VI)
- wherein phenyl ring “A” is substituted with 1 to 5 organic groups selected from the group consisting of(a) halo, cyano, hydroxy, C1-6 alkoxy, C1-6 carboxylic acid or ester, an amine or amide group;
- and (b) saturated or unsaturated straight or branched chain, or cyclic systems comprising from 1 to 12 carbon atoms and 0 to 4 heteroatoms each of which may be optionally substituted by the groups listed in (a).
8 more elements
Dependencies are inferred from the claim text.