Des-(ser13)-srif and intermediates

Claim 2

A tridecapeptide selected from those of the formula ##EQU4## and the non-toxic acid addition salts thereof, said amino acid residues in said tridecapeptide having an asymmetric α-carbon atom being of the L-configuration.

Claim 3

A peptide according to claim 1 which is: L-alanylglycyl-L-cysteinyl-L-lysyl-L-asparaginyl-L-phenylalanyl-L-phenylalanyl-L-tryptophyl-L-lysyl-L-threonyl-L-phenylalanyl-L-threonyl-L-cysteine and a non-toxic acid addition salt thereof.

Claim 4

A peptide according to claim 1 which is: L-alanylglycyl-L-cysteinyl-L-lysyl-L-asparaginyl-L-phenylalanyl-L-phenylalanyl-L-tryptrophyl-L-lysyl-L-threonyl-L-phenylalanyl-L-threonyl-L-cysteine (cyclic 1, 13 disulfide) and a non-toxic acid addition salt thereof.

Claim 5

A tridecapeptide of the formula: R-Ala-Gly-Cys(R.sup.1)-Lys(R.sup.6)-Asn-Phe-Phe-Trp-Lys(R.sup.2)-Thr(R.sup.3)-Phe-Thr(R.sup.4)-Cys(R.sup.5)-X wherein: R is selected from the group consisting of hydrogen and an α-amino protecting group; R 1 and R 5 are protecting groups for the sulfhydryl group on the cysteinyl amino acid residue selected from the group consisting of benzyl, trityl, benzyloxycarbonyl, benzhydryl, tetrahydropyranyl, acetamidomethyl, benzoyl, benzylthiomethyl, ethylcarbamyl, thioethyl, p-methoxybenzyloxycarbonyl, s-sulfonate salt and substituted benzyl wherein said substituent is selected from the group consisting of methyl, methoxy and nitro; R 2 and R 6 are selected from the group consisting of hydrogen and a protecting group for the side chain amino substituent of the lysine residue selected from benzyloxycarbonyl, tosyl, diisopropylmethyloxycarbonyl, t-amyloxycarbonyl, t-butyloxycarbonyl and substituted benzyloxycarbonyl wherein said substituent is selected from halo and nitro; R 3 and R 4 are selected from the group consisting of hydrogen and a protecting group for the alcoholic hydroxyl group of the threonine residue selected from acetyl, benzoyl, tert-butyl, trityl, benzyl, 2,6-dichlorobenzyl and benzyloxycarbonyl; X is selected from the class consisting of hydroxy, methoxy and ##EQU5## wherein said polystyrene is cross linked through the phenyl group on each second carbon atom of the alkyl chain of said polystyrene.

Claim 6

A tridecapeptide of the formula: R-Ala-Gly-Cys(R.sup.1)-Lys(R.sup.6)-Asn-Phe-Phe-Trp-Lys(R.sup.2)-Thr(R.sup.3)-Phe-Thr(R.sup.4)-Cys(R.sup.5)-X wherein: R is selected from the group consisting of hydrogen and an α-amino protecting group; R 1 and R 5 are protecting groups for the sulfhydryl group on the cysteinyl amino acid residue selected from the group consisting of benzyl, trityl, benzyloxycarbonyl, benzhydryl, tetrahydropyranyl, acetamidomethyl, benzoyl, benzylthiomethyl, ethylcarbamyl, thioethyl, p-methoxybenzyloxycarbonyl, s-sulfonate salt and substituted benzyl wherein said substituent is selected from the group consisting of methyl, methoxy and nitro; R 2 and R 6 are selected from the group consisting of hydrogen and a protecting group for the side chain amino substituent of the lysine residue selected from benzyloxycarbonyl, tosyl, diisopropylmethyloxycarbonyl, t-amyloxycarbonyl, t-butyloxycarbonyl and substituted benzyloxycarbonyl wherein said substituent is selected from halo and nitro; R 3 and R 4 are selected from the group consisting of hydrogen and a protecting group for the alcoholic hydroxyl group of the threonine residue selected from acetyl, benzoyl, tert-butyl, trityl, benzyl, 2,6-dichlorobenzyl and benzyloxycarbonyl; X is selected from the class consisting of hydroxy, methoxy and ##EQU5## wherein said polystyrene is cross linked through the phenyl group on each second carbon atom of the alkyl chain of said polystyrene.

Claim 7

A compound according to claim 4 wherein R is tert-butyloxycarbonyl.

Claim 8

A compound according to claim 5 wherein: R 1 is pmethoxybenzyl; R 2 and R 6 are 2-chlorobenzyloxycarbonyl; R 3 and R 4 are each benzyl and R 5 is 3,4-dimethylbenzyl.