AMD070, a CXCR4 chemokine receptor antagonist: Practical large-scale laboratory synthesis
An efficient and convergent four-step synthetic route to the CXCR4 chemokine receptor antagonist AMD070 (1) has been developed which employs only a single chromatographic step in the entire sequence. Novel reductive amination methods have been developed for the coupling of 2 and 3 in which a dehydrative imine formation is followed by reduction with an attenuated borohydride reagent (zinc chloride and sodium borohydride). Selective extraction methods were employed to purify synthetic intermediates and remove reagents and impurities. A procedure has also been developed to isolate 1 in a pure crystalline form.
Crawford, Jason B.,Chen, Gang,Gauthier, David,Wilson, Trevor,Carpenter, Bryon,Baird, Ian R.,McEachern, Ernie,Kaller, Alan,Harwig, Curtis,Atsma, Bem,Skerlj, Renato T.,Bridger, Gary J.
p. 823 - 830
(2013/01/03)
Chemokine combinations to mobilize progenitor/stem cells
Methods to elevate progenitor and stem cell counts in animal subjects using compounds which bind to the chemokine receptor CXCR4 in combination with the CXCR2 chemokine GROβ, including its modified forms, are disclosed.
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Page/Page column 25
(2008/06/13)
Process for the synthesis of CXCR4 antagonist
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′
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Page/Page column 11
(2010/02/14)
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