Process for the synthesis of a cxcr4 antagonist

Details Process for the synthesis of a cxcr4 antagonist Process for the synthesis of a cxcr4 antagonist

C - Chemistry, Metallurgy

07

D

C07D 215/38 (2006.01) A61K 31/4709 (2006.01)

Patent

CA 2558389

This invention relates to a process for synthesizing heterocyclic pharmaceutical compound which binds to the CXCR4 chemokine receptor. In one embodiment, the process comprises: a) reacting a 5,6,7,8- tetrahydroquinolinylamine and an alkyl aldehyde bearing a phthalimide or a di- tertiary-butoxycarbonyl (di-BOC) protecting group to form an imine; b) reducing the imine to form a secondary amine; c) reacting the secondary amine with a haloalkyl substituted heterocyclic compound, to form a phthalimido- protected or di-tert-butoxycarbonyl protected tertiary amine; and d) hydrolyzing the protected amine to obtain a compound having Formula (I~).

L'invention concerne un procédé destiné à synthétiser un composé pharmaceutique hétérocyclique qui se lie au récepteur de la chimiokine CXCR4. Dans un mode de réalisation, le procédé consiste (a) à faire réagir une 5,6,7,8-tétrahydroquinolinylamine et un alkyle aldéhyde supportant un phtalimide ou un groupe protecteur di-tertiaire-butoxycarbonyle (di-BOC) de sorte à former une imine, (b) à réduire cette imine de manière à former une amine secondaire, (c) à faire réagir l'amine secondaire avec un composé hétérocyclique à substitution haloalkyle de façon à former une amine tertiaire protégée par phtalimido ou par di-tert-butoxycarbonyle, et (d) à hydrolyser l'amine protégée en vue de l'obtention d'un composé de formule (I').

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