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

1993-06-29

1996-03-19

Warden, Jill

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Peptide containing doai

530315, 530328, A61K 3800, C07K 500, C07K 700, C07K 1700

Patent

active

055004130

ABSTRACT:
A process for the manufacture of 1-deamino-8-D-arginine vasopressin (DDAVP) comprising, condensing a preparation of Mpa(R.sup.1)-Tyr-Phe-Gln-Asn-Cys(R.sup.2)-Pro-OH (SEQ ID NO: 1), where R.sup.1 and R.sup.2 are sulfhydryl-protecting groups, with the dipeptide (R.sup.3)-D-Arg(HCl)-Gly-NH.sub.2, where R.sup.3 is an acid-sensitive amino-protecting group, to form Mpa(R.sup.1)-Tyr-Phe-Gln-Asn-Cys(R.sup.2)-Pro-D-Arg(HCl)-Gly-NH.sub.2 (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.

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Article entitled "Titanium (III) as a Selective Reducing Agent for Nitroarginyl Peptides: Synthesis of Arginine Vasotocine," by Freidinger, J. Org. Chem., 43:4800-4803 (1978).
K.--E. Andersson, B. Bengtsson and O. Paulsen, Desamino-8-D-Argomome Vasopressin (DDAVP): Pharmacology and Clinical Use 1988; 24(7): 509-528.

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