Fibronectin adhesion inhibitors

C - Chemistry – Metallurgy – 07 – K

Patent

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Details

C07K 14/78 (2006.01) A61K 38/12 (2006.01) A61K 38/39 (2006.01) C07K 1/06 (2006.01) C07K 7/54 (2006.01) C07K 7/64 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2204793

Cyclic peptides of formula (1) wherein: AA1 is an <u>L</u> or <u>D</u> amino acid selected form Ile and Leu or amino acid analogue thereof; AA2 is an <u>L</u> amino acid selected from Leu or amino acid analogue thereof; AA3 is an <u>L</u> amino acid selected from Asp or amino acid analogue thereof containing a carboxyl group in its side chain; AA4 is an <u>L</u> amino acid selected from Val or amino acid analogue thereof and; LINKER represents a linking moiety for linking N terminus of AA1 to C terminus of AA4 to form a cyclic peptide containing a heterocyclic ring having 17 to 30 members. The cyclic peptides inhibit the interaction of vascular cell adhesion molecule-1 and fibronectin with integrin very late antigen 4 and have therapeutic applications such as in rheumatoid arthritis or multiple sclerosis.

L'invention concerne des peptides cycliques de la formule (1). Dans cette formule, AA1 est un acide aminé <u>L</u> ou <u>D</u> choisi parmi les acides aminés Ile ou Leu ou des analogues de ceux-ci; AA2 est l'acide aminé <u>L</u>-Leu ou un analogue de celui-ci; AA3 est l'acide aminé <u>L</u>-Asp ou un analogue de celui-ci portant un groupe carboxylique sur sa chaîne latérale; AA4 est l'acide aminé <u>L</u>-Val ou un analogue de celui-ci; et "ELEMENT DE LIAISON" représente un groupe liant l'extrémité N-terminale de AA1 à l'extrémité C-terminale de AA4, pour former un peptide cyclique avec un hétérocycle ayant de 17 à 30 éléments. Ces peptides cycliques inhibent l'interaction de la molécule vasculaire d'adhésion cellulaire 1 (VCAM-1) et de la fibronectine avec les intégrines de la classe des antigènes très tardifs 4 (VLA-4). Ces peptides sont utiles dans les thérapies dirigées contre la polyarthrite rhumatoïde et la sclérose en plaques.

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