Improved processes for making hydrazides

Details Improved processes for making hydrazides Improved processes for making hydrazides

C - Chemistry, Metallurgy

07

C

C07C 241/04 (2006.01) A61K 47/48 (2006.01) C07C 243/28 (2006.01)

Patent

CA 2687852

A method is disclosed for preparing hydrazides from hydrazine and an acyl chloride which comprises the steps of (a) preparing a stirred substantially uniform slurry comprising hydrazine and an inert solvent at low temperature; and (b) adding an acyl chloride continuously to said slurry. The method avoids or limits production of undesired bis-hydrazide by-products. The method is used to prepare 3-methyl-3-mercaptobutanoic acid hydrazide, a molecule used to link calicheamicin to a monoclonal antibody.

La présente invention concerne un procédé de préparation d'hydrazides à partir d'hydrazine et d'un chlorure d'acyle comprenant les étapes suivantes: (a) la préparation d'une suspension sensiblement uniforme agitée comprenant de l'hydrazine et un solvant inerte à basse température; et (b) l'ajout en continu d'un chlorure d'acyle à la suspension. Le procédé permet d'éviter ou de réduire la production de sous-produits indésirables de bishydrazide. Le procédé est utilisé pour préparer de l'hydrazide de l'acide 3-méthyl-3-mercaptobutanoïque, une molécule utilisée pour lier la calichéamine à un anticorps monoclonal.

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