Claims
- 1. Pharmacologically active peptides of the following formulas:
- Tyr.sup.1 -X-A,
- Tyr.sup.1 X-A-Pro,
- Tyr.sup.1 -X-A-Pro-B,
- Tyr.sup.1 -X-A-Pro-B-Pro,
- Tyr.sup.1 -X-A-Pro-B-Pro-C,
- Tyr.sup.1 -X-A-Pro-B-Pro-C-Pro and
- Tyr.sup.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.
- 2. D-Ala.sup.2 -.beta.-casomorphin-5
- 3. D-Pro.sup.2 -.beta.-casomorphin-5
- 4. 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.sub.1 for hydrogen or an alkyl group with 1 to 4 C-atoms,
- R.sub.2 for hydrogen or together with R.sub.1 for an ethylene bond,
- R.sub.3 for hydrogen, an alkyl group with 1 to 4 C-atoms or a R.sub.4 CO-group,
- R.sub.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.sub.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.sub.4 CO--, H--Arg--, H--Lys--, H--Phe--, or H--Tyr--,
- (b) the L-phenylalanine is of the general formula ##STR10## in which: R.sub.5 represents hydrogen or alkyl with 1 to 4 C-atoms,
- R.sub.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.sub.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.
- 5. 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.
- 6. 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.
- 7. 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.
Priority Claims (1)
Number |
Date |
Country |
Kind |
2936099 |
Sep 1979 |
DEX |
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Parent Case Info
This application is a continuation-in-part of our copending patent application Ser. No. 229,577 filed Jan. 22, 1981, the entire contents of which is incorporated herein by reference.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/DE80/00126 |
9/4/1980 |
|
|
4/29/1981 |
4/29/1981 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO81/00712 |
3/19/1981 |
|
|
US Referenced Citations (9)
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
229577 |
Jan 1981 |
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