Synthesis and manufacture of pentostatin and its precursors,...

Details Synthesis and manufacture of pentostatin and its precursors,... Synthesis and manufacture of pentostatin and its precursors,...

C - Chemistry, Metallurgy

07

H

C07H 19/00 (2006.01) C07H 19/16 (2006.01) C07H 19/22 (2006.01)

Patent

CA 2538857

Methods and compositions are provided for efficiently preparing and manufacturing pentostatin. Also provided are novel precursors of pentostatin, pentostatin analogs and derivatives. In one aspect of the invention, a method is provided for total chemical synthesis of pentostatin via a route of heterocyclic ring expansion. For example, a heterocyclic pharmaceutical intermediate for drugs such as pentostatin, e.g., the diazepinone precursor, can be obtained efficiently through a ring expansion of an O-C-N functionality in a hypoxanthine or 2'-deoxyinosine derivative. The methods and compositions can also be used to synthesize and manufacture heterocyclic compounds other than pentostatin, especially pharmaceutically important heterocyclic compounds.

L'invention concerne des méthodes et des compositions permettant la préparation et la production efficaces de pentostatine. Cette invention concerne également de nouveaux précurseurs de la pentostatine ainsi que des analogues et dérivés de cette dernière. Un aspect de ladite invention concerne une méthode de synthèse chimique totale de la pentostatine par expansion d'un hétérocycle. Par exemple, un intermédiaire pharmaceutique hétérocyclique pour des médicaments tels que la pentostatine, p. ex. le précurseur de la diazépinone, peut être obtenu, de manière efficace, par une expansion de cycle d'une fonctionnalité O-C-N dans un dérivé d'hypoxanthine ou de 2'-désoxyinosine. Ces méthodes et compositions peuvent être également utilisées pour synthétiser et produire des composés hétérocycliques autre que la pentostatine, en particulier des composés hétérocycliques importants d'un point de vue pharmaceutique.

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