Secretin intermediates and derivatives

Claim 2

A compound which is a peptide selected from the group consisting of (a) [6-TYR] Secretin and its salts; and (b) 6-(radioiodinated-TYR) secretin, wherein the amino acid residues of the compound are in L-form and the radioiodine is selected from the group consisting of 125 I, 131 I and 123 I.

Claim 3

The compound of claim 1 wherein the peptide is [6-TYR] Secretin in L-form.

Claim 4

The compound of claim 1 wherein the peptide is 6-(radioiodinated-TYR) Secretin in L-form.

Claim 5

The compound of claim 1 wherein the compound is 6-(3 1 -iodo 125 I-tyrosyl) Secretin in L-form.

Claim 6

The compound of claim 1 wherein the compound is 6-(3 1 , 5 1 -diiodo - 125 I 2 - tyrosyl) Secretin in L-form.

Claim 7

The compound of claim 1 wherein the compound is 6 - (3 1 - iodo 131 I - tyrosyl) Secretin in L-form.

Claim 8

The compound of claim 1 wherein the compound is 6 - (3 1 - diiodo 131 I 2 - tyrosyl) Secretin in L-form.

Claim 9

A compound of the formula: ##SPC3## wherein R 1 is a solid polymer selected from the group consisting of polystyrene and polystyrene crosslinked with divinyl benzene, said polymer being linked through its phenyl ring; Y is selected from the group consisting of hydrogen and lower alkoxy; Z is selected from the group consisting of hydrogen, lower alkoxy and nitro, and X is selected from the group consisting of the following protected and unprotected amino acid residues, in L-form, and salts thereof, 1. TYR-THR-SER-GLU-LEU-SER-ARG-LEU-ARG-LEU-ARG-ASP-SER-ALA-ARG-LEU-GLN-ARG-LEU-LEU-GLN-GLY-LEU-VAL- 2. thr-tyr-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 3. gly-thr-tyr-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 4. asp-gly-thr-tyr-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val-

Claim 10

A compound of the formula: ##SPC3## wherein R 1 is a solid polymer selected from the group consisting of polystyrene and polystyrene crosslinked with divinyl benzene, said polymer being linked through its phenyl ring; Y is selected from the group consisting of hydrogen and lower alkoxy; Z is selected from the group consisting of hydrogen, lower alkoxy and nitro, and X is selected from the group consisting of the following protected and unprotected amino acid residues, in L-form, and salts thereof, 1. TYR-THR-SER-GLU-LEU-SER-ARG-LEU-ARG-LEU-ARG-ASP-SER-ALA-ARG-LEU-GLN-ARG-LEU-LEU-GLN-GLY-LEU-VAL- 2. thr-tyr-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 3. gly-thr-tyr-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 4. asp-gly-thr-tyr-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val-

Claim 11

ser-asp-gly-thr-tyr-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 6. his-ser-asp-gly-thr-tyr-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 7. phe-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 8. thr-phe-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 9. gly-thr-phe-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 10. asp-gly-thr-phe-thr-ser-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 11. ser-asp-gly-thr-phe-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 12. his-ser-asp-gly-thr-phe-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-arg-leu-leu-gln-gly-leu-val- 13. thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 14. ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 15. glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val-

Claim 12

ser-asp-gly-thr-tyr-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 6. his-ser-asp-gly-thr-tyr-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 7. phe-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 8. thr-phe-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 9. gly-thr-phe-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 10. asp-gly-thr-phe-thr-ser-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 11. ser-asp-gly-thr-phe-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 12. his-ser-asp-gly-thr-phe-thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-arg-leu-leu-gln-gly-leu-val- 13. thr-ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 14. ser-glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 15. glu-leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val-

Claim 13

leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val 17. ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 18. arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 19. leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 20. arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 21. asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 22. ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 23. ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 24. arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 25. leu-gln-arg-leu-leu-gln-gly-leu-val- 26. gln-arg-leu-leu-gln-gly-leu-val- 27. arg-leu-leu-gln-gly-leu-val- 28. leu-leu-gln-gly-leu-val- 29. leu-gln-gly-leu-val- 30. gln-gly-leu-val- 31. gly-leu-val- 32. gly-leu-val- 33. leu-val-

Claim 14

leu-ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val 17. ser-arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 18. arg-leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 19. leu-arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 20. arg-asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 21. asp-ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 22. ser-ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 23. ala-arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 24. arg-leu-gln-arg-leu-leu-gln-gly-leu-val- 25. leu-gln-arg-leu-leu-gln-gly-leu-val- 26. gln-arg-leu-leu-gln-gly-leu-val- 27. arg-leu-leu-gln-gly-leu-val- 28. leu-leu-gln-gly-leu-val- 29. leu-gln-gly-leu-val- 30. gln-gly-leu-val- 31. gly-leu-val- 32. gly-leu-val- 33. leu-val-

Claim 15

the compound of claim 8 wherein X is selected from the group consisting of protected and unprotected, HIS-SER-ASP-GLY-THR-TYR-THR-SER-GLU-LEU-SER-ARG-LEU-ARG-ASP-SER-ALA-ARG-LEU-GLN-ARG-LEU-LEU-GLN-GLY-LEU-VAL-

Claim 16

The compound of claim 8 wherein X is selected from the group consisting of protected and unprotected HIS-SER-ASP-GLY-THR-PHE-THR-SER-GLU-LEU-SER-ARG-LEU-ARG-ASP-SER-ALA-ARG-LEU-GLN-ARG-LEU-LEU-GLN-GLY-LEU-VAL-

Claim 17

The compound of claim 9 wherein the peptide is unprotected.

Claim 18

The compound of claim 10 wherein the peptide is unprotected.

Claim 19

The compound of claim 11 wherein Y and Z are hydrogen.

Claim 20

The compound of claim 12 wherein Y and Z are hydrogen.

Claim 21

The compound of claim 9 wherein the guanidine group of ARG is protected with a guanidine protecting group, the hydroxyl groups of SER, THR and TYR are protected with hydroxyl protecting groups, the carboxyl groups of ASP and GLU protected by carboxyl protecting groups, GLY, LEU, ALA, GLN and VAL are unprotected and HIS is selected from the group consisting of unprotected HIS, amino protected HIS, imidazole protected HIS and amino and imidazole protected HIS.

Claim 22

The compound of claim 10 wherein the guanidine group of ARG is protected with a guanidine protecting group, the hydroxyl groups of SER and THR are protected with hydroxyl protecting groups, the carboxyl groups of ASP and GLU protected by carboxyl protecting groups, GLY, LEU, PHE, ALA, GLN and VAL are unprotected and HIS is selected from the group consisting of unprotected HIS, amino protected HIS, imidazole protected HIS and amino and imidazole protected HIS.