Novel peptide dimers as agonists of the erythropoietin (epo)...

C - Chemistry – Metallurgy – 07 – K

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C07K 14/47 (2006.01) A61K 38/16 (2006.01) A61K 47/48 (2006.01) C07K 1/107 (2006.01) C07K 14/505 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2370322

Novel peptide dimers are provided that bind and activate the erythropoietin receptor (EPO-R) or otherwise act as an EPO agonist. The novel compounds have a first peptide chain R1 and a second peptide chain R2, wherein R1 and R2 may be the same or different, and are linked through a linking moiety. R1 is approximately 10 to 40 amino acid residues in length and comprises the sequence X3X4X5GPX6TX7X8X9 (SEQ ID NO: 1) wherein X3 is C or Hoc, X4 is R, H, L or W, X5 is M, F, I or nor-leucine (J), X6 is any one of the 20 genetically coded L-amino acids or J, X7 is W, 1-naphthylalanine (B) or 2-naphthylalanine (U), X8 is D, E, I, L or V, and X9 is C or Hoc. Similarly, R2 comprises the sequence X'3X'4X'5GPX'6TX'7X'8X'9 (SEQ ID NO: 2) wherein X'3 is C or Hoc, X'4 is R, H, L or W, X'5 is M, F, I or J, x'6 is any one of the 20 genetically coded L-amino acids or J, X'7 is W, B or U, X'8 is D, E, I, L or V and X'9 is C or Hoc. Methods for synthesizing the compounds are provided as well, as are pharmaceutical compositions and methods of use.

L'invention concerne de nouveaux dimères peptidiques qui lient et activent le récepteur d'érythropoïétine (EPO-R) ou agissent d'une autre manière comme un agoniste d'EPO. Les nouveaux composés ont une première chaîne peptidique R?1¿ et une deuxième chaîne peptidique R?2¿, les chaînes R?1¿ et R?2¿ pouvant être identiques ou différentes et étant reliées par le biais d'un groupe fonctionnel de liaison. R?1¿ a une longueur d'à peu près 10 à 40 résidus d'acides aminés et comprend la séquence X¿3?X¿4?X5GPX¿6?TX¿7?X¿8?X9 (SEQ ID NO: 1) dans laquelle X¿3? est C ou Hoc, X¿4? est R, H, L ou W, X¿5? est M, F, I ou nor-leucine (J), X¿6? est n'importe lequel des 20 acides aminés L génétiquement codés ou J, X¿7? est W, 1-naphthylalanine (B) ou 2-naphthylalanine (U), X¿8? est D, E, I, L ou V et X¿9? est C ou Hoc. De façon similaire, R2 comprend la séquence X'3X'4X'5GPX'6TX'7X'8X'9 (SEQ ID NO: 2) dans laquelle X'¿3? est C ou Hoc, X'¿4? est R, H, L ou W, X'¿5? est M, F, I ou J, X'¿6? est n'importe lequel des 20 acides aminés L génétiquement codés ou J, X'¿7? est W, B ou U, X'¿8? est D, E, I, L ou V et X¿'9? est C ou Hoc. L'invention concerne des procédés pour synthétiser des composés ainsi que des compositions pharmaceutiques et des procédés d'utilisation.

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