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AssigneeStragen Pharma S.A.
InventorsJean-Pierre Robin, Julie Blanchard, Ludovic Chauviat, Robert Dhal, Jean-Pierre Marie, Nina Radosevic
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The present invention concerns a new general process for asymmetric hemisynthesis of harringtonines and their analogs, that are alkaloids used in chemotherapy. This process comprises direct esterification of a natural cephalotaxine with an acylating compound constituted of a side chain precursor which backbone and functionalization are entirely preformed. The invention also concerns a natural, synthetic or semi-synthetic harringtonines including their tautomeric forms and their salts of the following formula: wherein n=2 (i.e. harringtonine) or n=3 (i.e. homoharringtonine), in which the total content of impurities, possibly including enantiomeric forms, is lower than 1%, and/or the content of the major impurity is lower than 0.9%, and/or the chromatographic assay exhibits a harringtonines content higher than 97.5%.
A natural, synthetic or semi-synthetic harringtonines of the following formula:
A crystalline natural, synthetic or semi-synthetic homoharringtonine having substantially the same DSC curve as set out in FIG. 1.
A crystalline natural, synthetic or semi-synthetic homoharringtonine having substantially the same X-ray diffractogram as set out in FIG. 2, and substantially the same IR spectrum, in KBr as set out in FIG. 3.
A crystalline natural, synthetic or semi-synthetic homoharringtonine having substantially the same DSC curve as set out in FIG. 1, substantially the same X-ray diffractogram as set out in FIG. 2, and substantially the same IR spectrum, in KBr as set out in FIG. 3.
A crystalline natural, synthetic or semi-synthetic harringtonine having substantially the same DSC curve as set out in FIG. 4
A crystalline natural, synthetic or semi-synthetic harringtonine having substantially the same IR spectrum, in KBr as set out in FIG. 5.
A crystalline natural, synthetic or semi-synthetic harringtonine having substantially the same DSC curve as set out in FIG. 4, and substantially the same IR spectrum, in KBr as set out in FIG. 5
Dependencies are inferred from the claim text.