Cyclic peptide surface feature mimics of endothelin

Details Cyclic peptide surface feature mimics of endothelin Cyclic peptide surface feature mimics of endothelin

1994-11-10

1998-04-07

Tsang, Cecilia J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Peptide containing doai

514 17, 530317, 530330, 930270, A61K 3800, C07K 500

Patent

active

057365091

ABSTRACT:
Cyclic peptides and pharmaceutically acceptable salts and esters thereof are provided. The cyclic peptides and pharmaceutically acceptable salts and esters thereof mimic surface features of the C-terminus of endothelin and thereby can be used modulate or alter the activity of the endothelin family of peptides. More particularly, cyclic pentapeptides, cyclic hexapeptides, cyclic heptapeptides and pharmaceutically acceptable derivatives of the peptides that specifically inhibit the activity of endothelin are provided. Among the cyclic peptides are those that have the formula: cyclo(X.sup.1 -X.sup.2 -X.sup.3 -X.sup.4 -D-Trp): X.sup.1 is D-Tyr or D-Asp; X.sup.2 is Phe, Ala, Ac.sub.3 c or Pro; X.sup.3 is D-His, D-Ala, D-Val, Gly or .beta.-Ala; and X.sup.4 is His, Ala, .beta.-Ala, Aib, Gly, D-His-gly or Leu; cyclo(X.sup.1 -L-Phe-X.sup.3 -X.sup.4 -X.sup.5) in which X.sup.1 is D-Tyr, D-Asp or D-Glu, X.sup.3 is selected from among D-His, .beta.-Ala-D-His or gly-D-His; X.sup.4 is Ser, Gly or .beta.-Ala, and X.sup.5 is D-Trp or N-Me-D-Trp; cyclo(X.sup.1 -X.sup.2 -X.sup.3 -X.sup.4 -L-Trp) in which X.sup.1 is D-Ala, Aib, Gly, D-Val, D-Leu, D-lle, D-Nva, D-Nle, or D-Alle; X.sup.2 is D-Val, D-Leu, D-lle, D-Ala, D-Gln, Gly, Aib, D-Nva, D-Nle, or D-Alle; X.sup.3 is Pro, Gly, Aib, Val, Leu, L-Nva, L-Nle, L-Alle or L-Hyp and X.sup.4 is D-Asp, D-Glu, D-Ser, D-Thr, D-Tyr, D-Cys(O.sub.3 H) or D-Pen(O.sub.3 H); and cyclo(X.sup.1 -X.sup.2 -X.sup.3 -X.sup.4 -L-Trp) in which X.sup.1 is D-Leu, D-Val, D-lle, D-Ala, Gly, Aib, D-Nva, D-Nle or D-Alle; X.sup.2 is Val, lle, Leu, Ala, Gln, Gly, Aib, L-Nva, L-Nle or L-Alle; X.sup.3 is D-Pro, D-Hyp, D-Ala, D-Val, D-lle, Gly, Aib, D-Nva, D-Nle or D-Alle; and X.sup.4 is Asp, Glu, Tyr, Ser, Thr, L-Cys(O.sub.3 H) or L-Pen(O.sub.3 H). Pharmaceutical compositions containing the peptides and methods of modulating the activity of endothelin peptides are also provided.

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