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US 6,673,769 B2Granted
Lanthionine bridged peptides
AssigneeWinfried Kolbeck
InventorsMurray Goodman, George Osapay
Life of this patent
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Abstract
Disclosed are lanthionine bridged peptides having the structure methods of their preparation and their use as pharmacologically active agents.
Claims6
Lanthionine-bridged peptides of the formula:
- wherein R1 is a tetrapeptide selected from the group consisting of
- Tyr-Phe-Gln-Asn, Phe-D-Trp-Lys-Thr, Phe-D-Trp-Lys-Val, Tyr-lleu-Gln-Asn, and Tyr-D-Trp-Lys-Val;
- R2 represents en amino acid selected from the group consisting of D-Phe, D-β-Nal, Tyr, TrpNH2, Thr NH2, Thr(ol), or represents H, acyl or aracyl with 2 to 12 carbon atoms;
- or an amino acid sequence selected from the group consisting of Pro-Arg-Gly and Pro-u-Gly
- R3 is selected from the group consisting of —OH, NH3;
- TrpNH2, ThrNH2, Thr(ol), Leu, Arg, where the -C terminal —COOH is present or is replaced by —CONH2 or —CH2OH;
- and
- may be replaced by CH2OH;
- and with the proviso that when R1 is Phe-Trp-Lys-Thr R2 is not Phe and/or R3 is not Thr;
- R4, R5, R7 and R8 independently represent hydrogen, a methyl group or a C1-10 alkyl group,
7 more elements
The Lanthionine-bridged peptides:
- (a) H-D-Phe-c[AlaLPhe-D-Trp-Lys-Thr-AlaL]-OH
- (b) H-D-Phe-c[AlaLPhe-D-Trp-Lys-Thr-AlaL]-Thr-ol
- (c) H-D-Phe-c[AlaLPhe-D-Trp-Lys-Thr-AlaL]-Thr-NH2.
Dependencies are inferred from the claim text.