Novel mu opioid receptor ligands: agonists and antagonists

Details Novel mu opioid receptor ligands: agonists and antagonists Novel mu opioid receptor ligands: agonists and antagonists

C - Chemistry, Metallurgy

07

K

C07K 7/06 (2006.01) C07K 5/087 (2006.01) C07K 5/10 (2006.01) C07K 5/107 (2006.01) C07K 5/117 (2006.01) C07K 14/665 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2223428

The present invention provides novel opioid peptides. Disclosed are opioid peptides having the general structure Ac-Phe-Arg-Trp-Trp-Tyr-Xaa-NH2 (SEQ ID No. 1); Ac-Arg-Trp-Ile-Gly-Trp-Xaa-NH2 (SEQ ID No. 2); Trp-Trp-Pro-Lys/Arg- Hisz-Xaaz-NH2 (SEQ ID No. 222); Tyr-Pro-Phe-Gly-Phe-Xaa-NH2 (SEQ ID No. 5); (D)Ile-(D)Met-(D)Ser-(D)Trp-(D)Trp-Glyn-Xaa-NH2 (SEQ ID No. 6); and (D)Ile- (D)Met-(D)Thr-(D)Trp-Gly-Xaa-NH2 (SEQ ID No. 7). Within each genus, Xaa is substituted by a specific amino acid. The invention also relates to an opioid peptide having general structure Tyr-A1-B2-C3-NH2 (SEQ ID No. 8), wherein A is D-Nve or D-Nle, B is Gly, Phe, or Trp, and C is Trp or Nap. Also included within the invention are opioid compounds of the general structure MexHyN-Tyr- Tyr-Phez-Proz-NH2 (SEQ ID No. 221) which are peptides modified by permethylation, perallylation, perethylation, perbenzylation or pernaphthylation and which be further modified by reduction.

L'invention concerne de nouveaux peptides opioïdes de structures générales Ac-Phe-Arg-Trp-Trp-Tyr-Xaa-NH¿2? (No. d'identification de séquence 1); Ac-Arg-Trp-Ile-Gly-Trp-Xaa-NH¿2? (No. d'identification de séquence 2); Trp-Trp-Pro-Lsy/Arg-His¿z?-Xaa¿z?-NH¿2? (No. d'identification de séquence 222); Tyr-Pro-Phe-Gly-Phe-Xaa-NH¿2? (No. d'identification de séquence 5); (D)Ile-(D)-Met-(D)Ser-(D)Trp-(D)Trp-Gly¿n?-Xaa-NH¿2? (No. d'identification de séquence 6); et (D)Ile-(D)Met-(D)Thr-(D)Trp-Gly-Xaa-NH¿2? (No. d'identification de séquence 7). Dans chaque genre, Xaa est substitué par un acide aminé spécifique. L'invention concerne également un peptide opioïde de structure générale Tyr-Al-B2-C3-NH¿2? (No. d'identification de séquence 8), dans laquelle A désigne D-Nve ou D-Nle, B désigne Gly, Phe ou Trp, et C désigne Trp ou Nap, et des composés opioïdes de structure générale Me¿x?H¿Y?N-Tyr-Tyr-Phe¿z?-Pro¿z?-NH¿2? (No, d'identification de séquence 221), qui sont des peptides modifiés par perméthylation, perallylation, peréthylation, perbenzylation ou pernaphtylation et qui peuvent être encore modifiés par réduction.

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