Stereoselective synthesis of amino acid analogs for tumor...

Details Stereoselective synthesis of amino acid analogs for tumor... Stereoselective synthesis of amino acid analogs for tumor...

C - Chemistry, Metallurgy

07

C

C07C 229/48 (2006.01) A61K 51/04 (2006.01) C07B 59/00 (2006.01) C07C 227/32 (2006.01)

Patent

CA 2612187

The radiolabeled non-natural amino acid 1-amino-3- cyclobutane-1-carboxylic acid (ACBC) and its analogs are candidate tumor imaging agents useful for positron emission tomography and single photon emission computed tomography due to their selective affinity for tumor cells. The present invention provides methods for stereo-selective synthesis of syn-ACBC analogs. The disclosed synthetic strategy is reliable and efficient and can be used to synthesize a gram quantity of various syn-isomers of the ACBC analogs, particularly, syn- [18F]-1-amino-3-fluorocyclobutane-1-carboxylic acid (FACBC) and syn- [123I]-1-amino-3-iodocyclobutane-1-carboxylic (IACBC) acid analogs.

La présente invention concerne un acide aminé radio-marqué d'origine non naturelle, l'acide 1-amino-3-cyclobutane-1-carboxylique (ACBC) et ses analogues qui sont des agents candidats pour l'imagerie des tumeurs utilisables dans la tomographie par émission de positons et la tomographie informatisée par émission à photon unique en raison de leur affinité sélective pour les cellules tumorales. La présente invention concerne des procédés de synthèse stéréo-sélective d'analogues de syn-ACBC. La stratégie de synthèse présentée est fiable et efficace et elle peut être utilisée pour synthétiser une quantité de l'ordre du gramme de divers syn-isomères d'analogues d'ACBC, en particulier l'acide syn-[18F]-1-amino-3-fluorocyclobutane-1-carboxylique (FACBC) et les analogues de l'acide syn-[123I]-1-amino-3-iodocyclobutane-1-carboxylique (IACBC).

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