Novel highly potent agonists of growth hormone releasing...

Details Novel highly potent agonists of growth hormone releasing... Novel highly potent agonists of growth hormone releasing...

C - Chemistry, Metallurgy

07

K

C07K 14/60 (2006.01) A61K 38/25 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2211122

Synthetic peptides which have the sequence: Q1-CO-Ala2-Asp3-Ala4-Ile5-Phe6- Thr7-R8-Ser9-Tyr10-Arg11-R12-Val13-Leu14-R15-Gln16-Leu17-Ser18-Ala19-Arg20-R21- Leu22-Leu23-GIn24-Asp25-Ile26-R27-R28-NH-Q2 wherein Q1 is an omega or alpha- omega substituted alkyl of structure (I), where: [.PHI. is phenyl; Y is H, -NH2, CH3CONH- or CH3NH-; Z is H or CH3; m is 1 or 2; n is 0, 1 or 2; R8 is Asn, Ser, Gln or Thr, R12 is Lys or Orn; R15 is Gly, Ala, or Abu; R21 is Lys or Orn; R27 is Met or Nle; R28 is Ser or Asp; and Q2 is a lower omega-guanidino-alkyl group having a formula: -(CH2)p-NH-C(NH2) - NH wherein p is 2-6, and the pharmaceutically acceptable addition salts thereof with the pharmaceutically acceptable organic or inorganic bases or acids.

L'invention se rapporte à des peptides synthétiques qui ont la séquence: Q<1>-CO-Ala<2>-Asp<3>-Ala<4>-Ile<5>-Phe<6>-Thr<7>-R<8>-Ser<9>-Tyr<10>-Arg<11>-R<12>-Val<13>-Leu<14>-R<15>-Gln<16>-Leu<17>-Ser<18>-Ala<19>-Arg<20>-R<21>-Leu<22>-Leu<23>-Gln<24>-Asp<25>-Ile<26>-R<27>-R<28>-NH-Q<2> dans laquelle Q<1> représente un alkyle substitué par oméga ou alpha-oméga de la structure (I) dans laquelle [ PHI ] représente phényle; Y représente H, -NH2, CH3CONH- ou CH3NH; Z représente H ou CH3; m représente 1 ou 2; n vaut 0, 1 ou 2; R<8> représente Asn, Ser, Gln ou Thr; R<12> représente Lys ou Orn; R<15> représente Gly, Ala ou Abu; R<21> représente Lys ou Orn; R<27> représente Met ou Nle; R<28> représente Ser ou Asp; et Q<2> représente un groupe oméga-guanidino-alkyle inférieur ayant la formule: -(CH2)p-NH-C(NH2) = NH dans laquelle p vaut de 2 à 6. L'invention se rapporte également aux sels d'addition pharmaceutiquement acceptables de ces peptides ainsi qu'aux bases ou acides organiques ou inorganiques pharmaceutiquement acceptables.

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