Process for manufacture of 1-deamino-8-d-arginine vasopressin

Details Process for manufacture of 1-deamino-8-d-arginine vasopressin Process for manufacture of 1-deamino-8-d-arginine vasopressin

C - Chemistry, Metallurgy

07

K

C07K 7/16 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2166297

A process for the manufacture of 1-deamino-8-D-arginine vasopressin (DDAVP) comprising a preparation of Mpa(R1)-Tyr- Phe-Gln-Asn-Cys(R2)-Pro-OH (SEQ ID NO: 1), where R1 and R2 are sulfhydryl-protecting groups, with the dipeptide (R3)-D-Arg(HCl)-Gly- NH2, where R3 is an acid-sensitive amino-protecting group, to form Mpa(R1)-Tyr-Phe-Gln-Asn-Cys(R2)-Pro-D-Arg(HCl)-Gly-NH2 (SEQ ID NO: 1), which is oxidized with iodine in a protic solvent. The reaction mixture containing the oxidized product can be purified by ion exchange chromatography on a cation exchange resin equilibrated with acid. Also disclosed is high-purity DDAVP obtained by this process and its use for treating diurea.

Procédé de fabrication de vasopressine 1-désamino-8-D-arginine (DDAVP), consistant à faire condenser une préparation de Mpa(R1)-Tyr-Phe-Gln-Asn-Cys(R2)-Pro-OH (SEQ ID NO: 1), où R1 et R2 représentent des groupes protecteurs de sulfhydryle, avec le dipeptide (R3)-D-Arg(HCl)-Gly-NH2, où R3 représente un groupe amino-protecteur sensible aux acides, de manière à former Mpa(R1)-Tyr-Phe-Gln-Asn-Cys(R2)-Pro-D-Arg(HCl)-Gly-NH2 (SEQ ID NO: 1), que l'on fait oxyder avec de l'iode dans un solvant protique. On peut purifier le mélange réactionnel renfermant le produit oxydé, par chromatographie d'échange d'ions sur une résine échangeuse de cations équilibrée à l'aide d'un acide. On a également prévu la DDAVP de grande pureté obtenue grâce à ce procédé, ainsi que son application au traitement de la diurèse.

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