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Somatostatin analogs with dissociated biological activities

  • US 4,133,782 A
  • Filed: 04/07/1977
  • Issued: 01/09/1979
  • Est. Priority Date: 06/07/1976
  • Status: Expired due to Term
First Claim
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1. A peptide selected from those of the formulae:

  • ##STR4## and the non-toxic salts thereof, wherein X1 is selected from Asn and des-Asn;

    X2 is selected from Trp and D-Trp;

    X3 is selected from Ser and D-Ser; and

    X4 is selected from Cys and D-Cys with the proviso that X1 is des-Asn when X2 is D-Trp, X3 is Ser and X4 is Cys;

    X3 is D-Ser when X1 is Asn and X4 is Cys; and

    X4 is D-Cys when X1 is Asn and X3 is Ser;

    R is selected from the class consisting of H and an alpha-amino protecting group;

    R1 and R7 are selected from the group consisting of H and a protecting group for Cys selected from S-p-methoxybenzyl, S-p-methylbenzyl, S-acetamidomethyl, S-trityl and S-benzyl;

    R2 and R3 are selected from the group consisting of H and a side chain amino protecting group for Lys selected from the group consisting of benzyl, chlorobenzyloxycarbonyl, benzyloxycarbonyl, tosyl, t-amyloxycarbonyl, t-butyloxycarbonyl, R4, R5 and R6 are selected from the group consisting of H and a hydroxyl protecting group selected from the group consisting of acetyl, benzoyl, tert-butyl, trityl, benzyl and benzyloxycarbonyl;

    with the proviso that at least one of R, R1, R2, R3, R4, R5, R6 and R7 is other than hydrogen; and

    X5 is selected from the group consisting of hydroxy, methoxy, esters, amides, hydrozides, -O-CH2 -polystyrene resin support and O-CH2 -benzyl-polystyrene resin support.

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