Peptides with para-substituted phenylalanine

Details Peptides with para-substituted phenylalanine Peptides with para-substituted phenylalanine

1978-12-07

1980-07-08

Phillips, Delbert R.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424177, C07C10352, A61K 3700

Patent

active

042116937

ABSTRACT:
Somatostatin peptides are modified by substitution of para-methoxylated Phe or para-halogenated Phe for any Phe in the peptide. The modified somatostatin peptide analogs have the formulae: ##STR1## wherein R is hydrogen or an acyl group; R.sub.1 is selected from the group consisting of Lys or Des R.sub.1 ; R.sub.2 is selected from the group consisting of Asn, Ala or Des R.sub.2. The amino acids of the R.sub.2 group can be either the L-form or the D-form; R.sub.3 is selected from the group consisting of Trp or D-Trp; R.sub.4 is selected from the group consisting of Thr or Des R.sub.4 ; R.sub.5 is selected from the group consisting of Ser, D-Ser, Phe, X or Des R.sub.5 ; and X is selected from the group consisting of Phe, para-halogenated Phe and para-methoxylated Phe. Provided that at least one X is either para-halogenated Phe or para-methoxylated Phe.

REFERENCES:
patent: 4011207 (1977-03-01), Sarantakis
patent: 4062816 (1977-12-01), Shields
patent: 4066827 (1978-01-01), Seita et al.
patent: 4093574 (1978-06-01), Shields
patent: 4105603 (1978-08-01), Vole, Jr. et al.
patent: 4115554 (1978-09-01), Veber
Rivier et al., J. Med. Chem. 1976, 19, 1010-1013.

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