Somatostatin analogs with dissociated biological activities
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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Abstract
The present invention relates to peptides having dissociated biological activity in respect to the inhibition of growth hormone, insulin, and glucagon secretion. The peptides are analogs of somatostatin.
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Citations
20 Claims
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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. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20)
- ##STR4## and the non-toxic salts thereof, wherein X1 is selected from Asn and des-Asn;
Specification