Methods of synthesis of certain hydroxamic acid compounds

C - Chemistry – Metallurgy – 07 – C

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C07C 311/45 (2006.01)

Patent

CA 2700173

The present invention pertains to the general field of chemical synthesis, and more particularly to methods for the synthesis of certain hydroxamic acid compounds, and in particular, (E)-N- hydroxy-3-(3-phenylsulfamoyl-phenyl)-acrylamide, also known as PXD101 and Belinostat ®, comprising, for example, the steps of: (SAF) sulfonamide formation; (PUR c) optional purification; (AAA) alkenyl acid addition, comprising: either (i): the steps of, in order: (ACAEA) alkenyl carboxylic acid ester addition; (PUR E) optional purification; and (CAD) carboxylic acid deprotection; or (ii): the step of: (ACAA) alkenyl carboxylic acid addition; (PUR F) optional purification; (HAF) hydroxamic acid formation; and (PUR G) optional purification.

La présente invention concerne le domaine général de la synthèse chimique, et plus particulièrement des procédés de synthèse de certains composés d'acide hydroxamique, et notamment le E)-N-hydroxy-3-(3-phénylsulfamoyl-phényl)-acrylamide, également connu sous le nom de PXD101 et de Belinostat®, qui comprend par exemple les étapes suivantes : (SAF) formation de sulfonamide ; (PURC) purification optionnelle ; (AAA) addition d'acide alcénylique, qui comprennent : soit (i) : les étapes suivantes, dans l'ordre : (ACAEA) addition d'un ester d'un acide carboxylique alcénylique ; (PURE) purification optionnelle ; et (CAD) déprotection de l'acide carboxylique ; ou (ii) : les étapes suivantes : (ACAA) addition d'un acide carboxylique alcénylique ; (PURF) purification optionnelle ; (HAF) formation d'un acide hydroxamique ; et (PURG) purification optionnelle.

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