Process for production of the somatostatin analog, octreotide

Details Process for production of the somatostatin analog, octreotide Process for production of the somatostatin analog, octreotide

2006-01-17

2006-01-17

Tate, Christopher R. (Department: 1654)

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

8 to 10 amino acid residues in defined sequence

C530S317000, C530S333000, C424S177100

Reexamination Certificate

active

06987167

ABSTRACT:
The present invention relates to a process for commercial production of octreotide using solution peptide chemistry and inexpensive amino acid derivatives. Thus the hexapeptide (Boc) D-Phe-Cys(Acm)-Phe-D-Trp-Lys(Boc)-Thr-OMe is synthesized by condensation of two tripeptide fragments, saponified and condensed with Cys(Acm)-Thr-OL to give the linear octapeptide alcohol. The linear peptide alcohol is treated with iodine, after removal of Boc groups, to give the cyclic peptide octreotide. The linear octapeptide alcohol can alternately be made by condensation of the protected hexapeptide acid with the dipeptide Cys(Acm)-Thr-OMe, followed by reduction with sodium borohydride.

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