Process for producing triglycyl-lysine vasopressin and intermediates therefor

US4093610A · kind A · utility

Assignee

• Amerimas Home Products, Inc. · US

Inventors

• Nedumparambil A. Abraham · Dollard-Des-Ormeaux, CA
• Hans U. Immer · Mount Royal, CA
• Kazimir Sestanj · Mont-Laurier, CA

Key dates

• Filing date: Jan 31, 1977
• Grant date: Jun 6, 1978
• Expiry date: Jan 31, 1997

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y10S930/15
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

A new process for preparing the cyclic dodecapeptide triglycyl-lysine vasopressin of the formula ##STR1## which comprises the preparation of a first hexapeptide of formula Boc--Gly--Gly--Gly--Cys(Trt)--Tyr--Phe--NHNH.sub.2 and a second hexapeptide of formula H--Gln(Mbh)--Asn(Mbh)--Cys(Trt)--Pro--Lys(Boc)--Gly--NH.sub.2 by a series of condensations involving the reaction of an appropriately protected peptide unit having an activated carboxyl with an appropriately protected peptide having a free amino group. Subsequently, the first and second hexapeptides are condensed according to the azide coupling method to obtain the linear protected dodecapeptide of formula Boc--Gly--Gly--Gly--Cys(Trt)--Tyr--Phe--Gln(Mbh)--Asn(Mbh)--Cys(Trt)--Pro- -Lys(Boc)--Gly--NH.sub.2 ; thereafter the linear protected dodecapeptide is transformed into the desired cyclic dodecapeptide, triglycyllysine vasopressin, by oxidizing and deprotecting processes.