A short synthesis of argatroban. a potent selective thrombin inhibitor.
Argatroban was synthesized in seven steps from 4-methylpiperidine. The condensation of (+/-)-trans-benzyl 4-methylpipecolic acid ester with N(alpha)-Boc-N(omega)-nitro-L-arginine led to two diastereomers that were separated. One of them is the precursor of argatroban.
Cossy
J
J
Laboratoire de Chimie Organique associé au CNRS, ESPCI, 10 rue Vauquelin, 75231 Cedex 05, Paris, France. janine.cosy@espci.fr
Belotti
D
D
D000991:Antithrombins / Q000138:chemical synthesis* / Q000494:pharmacology*; D001120:Arginine / Q000031:analogs & derivatives; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000494:pharmacology*; D010880:Piperidines / Q000138:chemical synthesis; D012680:Sensitivity and Specificity; D013449:Sulfonamides
D000991:Antithrombins; D004791:Enzyme Inhibitors; D010875:Pipecolic Acids; D010880:Piperidines; D013449:Sulfonamides; C032727:piperidine; D001120:Arginine; C031345:pipecolic acid; C031942:argatroban