Pharmacologically active peptides and medicaments containing the same

Claim 2

Pharmacologically active peptides of the following formulas: Tyr 1 -X-A, Tyr 1 X-A-Pro, Tyr 1 -X-A-Pro-B, Tyr 1 -X-A-Pro-B-Pro, Tyr 1 -X-A-Pro-B-Pro-C, Tyr 1 -X-A-Pro-B-Pro-C-Pro and Tyr 1 -X-A-Pro-B-Pro-C-Pro-D wherein X represents D-proline, D-alanine, D-threonine or D-valine; A represents phenylalanine, proline and tyrosine B represents L-glycine, proline and tyrosine, C represents L-isoleucine and D represents L-asparagine, proline and isoleucine.

Claim 3

D-Ala 2 -β-casomorphin-5

Claim 4

D-Ala 2 -β-casomorphin-5

Claim 5

D-Pro 2 -β-casomorphin-5

Claim 6

D-Pro 2 -β-casomorphin-5

Claim 7

Pharmacologically active peptides according to claim 1 in which: (a) the end-positioned L-tyrosine present is of the general formula ##STR8## wherein the individual meaning is: R 1 for hydrogen or an alkyl group with 1 to 4 C-atoms, R 2 for hydrogen or together with R 1 for an ethylene bond, R 3 for hydrogen, an alkyl group with 1 to 4 C-atoms or a R 4 CO-group, R 4 for a saturated or unsaturated straight or branched chain alkyl residue with 1 to 17 C-atoms, a phenyl residue or a phenylalkyl residue with 7 to 12 C-atoms, in which the phenyl residues can be substituted by 1 or 2 substituents of the halogen series, alkyl with 1 to 4 C-atoms or alkoxy with 1 to 4 C-atoms, in which the R 3 O group is in meta or para position to ##STR9## W represents hydrogen, alkyl with 1 to 5 C-atoms, alkenyl with 3 to 5 C-atoms, cyclopropylmethyl, cyclobutylmethyl, R 4 CO--, H--Arg--, H--Lys--, H--Phe--, or H--Tyr--, (b) the L-phenylalanine is of the general formula ##STR10## in which: R 5 represents hydrogen or alkyl with 1 to 4 C-atoms, R 6 represents hydrogen, fluorine, chlorine, bromine, nitro, alkyl with 1 to 4 C-atoms or alkoxy with 1 to 4 C-atoms, Z for 1 or 2. (c) the L-proline (at the 4, 6 or 8 positions of the peptide) have the formula ##STR11## in which: R 7 represents hydrogen, a hydroxy group, an alkyl group or alkoxy group with 1 to 4 C-atoms; an alkyl group or alkoxy group with 1 to 4 C-atoms is bonded at the nitrogen, and one or more keto groups are positioned on the ring; and (d) the end-positioned, C-terminal amino acid positioned to the right of Tyr in the peptide chain is present as an amide or ester.

Claim 8

A pharmacologically active peptide according to claim 1 in which the peptide has an end positioned methionine and the peptide is a tri-, penta-, hepta- or nonapeptide.

Claim 9

A pharmaceutical composition comprising a non-toxic pharmaceutically acceptable carrier and a peptide according to claim 1, or an acid addition salt or metal complex of the peptide, with said peptide constituting about 0.1 to 99.5 weight percent of the composition.

Claim 10

A pharmaceutical composition in unit dosage form comprising a non-toxic pharmaceutically acceptable carrier and about 10 to 300 mg of a peptide according to claim 1, or an acid addition salt or metal complex of the peptide.