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US RE30,731 EGranted
Enkephalin analogues
OwnerDerek Hudson, Robert Sharpe +1inventors
InventorsDerek Hudson, Robert Sharpe, Michael Szelke
Life of this patent
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Abstract
Compounds corresponding in structure to enkephalin or polypeptide analogues thereof, wherein one or more peptide links of the enkephalin or analogue is represented by a group or groups the same or different selected from dimethylene, methylene-imino and keto-methylene groups.
Claims8
Compounds having the general formula
- R--Tyr--X--Gly--B--Y--Z
- where
- (a) --X is a Gly or any D-amino acid residue
- --B is a Phe or N-methyl Phe residue
- --Y is Leu, Met (as such or in the form of its sulphoxide), Pro, or Hypro, or formal derivatives thereof in which the [carbonyl oxygen of the] terminal [carboxyl] ##STR23## group is replaced by [hydrogen atoms] --CH.sub.2 --Z --Z is NHR or OR
- (b) The peptide link between one or more of the residues is represented by a group or groups the same or different selected from dimethylene (except where X=Gly and the Gly-Gly link is involved) , methylene-imino and ketomethylene groups.
- (c) R is hydrogen or methyl, ethyl, propyl, cyclopropyl, butyl, allyl or other protective aliphatic group.
4 more elements
The compound NH.sub.2 --CH(CH.sub.2 C.sub.6 H.sub.4 OH)--CH.sub.2 --CH.sub.2 --CH.sub.2 --CO--Gly--Phe--Met--NH.sub.2.
[7. The compound H--Tyr--NH--CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2
- --CO--Phe--Met--NH.sub.2.] 8. The compound NH.sub.2 --CH(CH.sub.2 C.sub.6 H.sub.4 OH)--CH.sub.2 --NH--CH.sub.2
- --CO--Gly--Phe--Met--NH.sub.2. 9. The compound NH.sub.2 --CH(CH.sub.2
- C.sub.6 H.sub.4 OH)--CH.sub.2 --NH--CH.sub.2 --CO--Gly--Phe--Metol. 10. The compound H--Tyr--NH--CH.sub.2 --CO--CH.sub.2 --CH.sub.2
- CO--Phe--Met--OH. 11. The compound H--Tyr--NH--CH.sub.2 --CH.sub.2
- --NH--CH.sub.2 CO--Phe--Met--OH. 12. The compound H--Tyr--NH--CH.sub.2
- --CH.sub.2 --NH--CH.sub.2 --CO--Phe--Metol. 13. The compound H--Tyr--NH--CH.sub.2 --CH.sub.2 --NH--CH.sub.2 --CO--Phe--Met--NH.sub.2.
- . A pharmaceutical composition comprising as the active ingredient compounds of claim 1 or pharmaceutically acceptable N-protected or salt
- forms thereof in a pharmaceutically acceptable diluent or carrier. 15. A pharmaceutical composition according to claim 14 wherein the active
- ingredient is a compound wherein X is gly D-ala or D-met. 16. A pharmaceutically active composition according to claim 14 wherein the active ingredients is a compound wherein the Phe or N-methyl Phe residue representing B is substituted with a hydroxy group or halogen in the
- aromatic ring. 17. A pharmaceutical composition according to claim 14 wherein the active ingredient is a compound wherein Y is Leu, Met (as such or in the form of its sulphoxide), Pro, or Hypro, or formal derivatives thereof in which the carbonyl oxygen of the terminal carboxyl group is
- replaced by hydrogen atoms. 18. A pharmaceutical composition according to claim 14 wherein the active ingredient is a compound wherein one or more of the remaining peptide links and/or any methylene-inimo group(s) present is in N-substituted form carrying a methyl, ethyl, propyl, cyclopropyl,
- butyl, allyl or other protective aliphatic group. 19. A pharmaceutical composition according to claim 14 wherein the active ingredient is NH.sub.2 --CH(CH.sub.2 C.sub.6 H.sub.4 OH)--CH.sub.2 --CH.sub.2 --CH.sub.2 --CO--Gly--Phe--Met--NH.sub.2.
9 more elements
[20. A pharmaceutical composition according to claim 14 wherein the active ingredient is H--Tyr--NH--CH.sub.2 --CH.sub.2 --CH.sub.2 --CO--Phe--Met--NH.sub.2.]
- A pharmaceutical composition according to claim 14 wherein the active ingredient is NH.sub.2 --CH(CH.sub.2 C.sub.6 H.sub.4 OH)--CH.sub.2
- --NH--CH.sub.2 --CO--Gly--Phe--Met--NH.sub.2. 22. A pharmaceutical composition according to claim 14 wherein the active ingredient is NH.sub.2 --CH(CH.sub.2 C.sub.6 H.sub.4 OH)--CH.sub.2 --NH--CH.sub.2
- CO--Gly--Phe--Metol. 23. A pharmaceutical composition according to claim 14 wherein the active ingredient is [H--Try--NH--CH.sub.2 --CO--CH.sub.2 --CH.sub.2 --CO--Phe--Met--OH] H--Tyr--NH--CH.sub.2 --CO--CH.sub.2
- --CH.sub.2 --CO--Phe--Met--OH . 24. A pharmaceutical composition according to claim 14 wherein the active ingredient is [H--Tyr--NH--CH.sub.2 --CO--CH.sub.2 --CH.sub.2 --CO--Phe--Met--OH] H--Tyr--NH--CH.sub.2 --CH.sub.2 --NH--CH.sub.2
- CO--Phe--Met--OH . 25. A pharmaceutical composition according to claim 14 wherein the active ingredient is H--Tyr--NH--CH.sub.2 --CH.sub.2
- --NH--CH.sub.2 --CO--Phe--Metol. 26. A pharmaceutical composition according to claim 14 wherein the active ingredient is H--Tyr--NH--CH.sub.2 --CH.sub.2 --NH--CH.sub.2 --CO--Phe--Met--NH.sub.2.
3 more elements
Dependencies are inferred from the claim text.