Novel peptide derivatives, preparation and therapeutic and...

C - Chemistry – Metallurgy – 07 – K

Patent

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Details

C07K 14/685 (2006.01) A61K 38/34 (2006.01) A61P 17/00 (2006.01) C07K 7/06 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2474719

The invention relates to peptides of formula (1) R-V ?l¿-Ala?2¿-His?3¿-X?4¿-Y?5¿-Trp ?5¿-NH2 wherein R represents a hydrogen atom or a protective group which can be chosen from among a benzoyl group, a tosyl group, a benzene sulfonyl group, a benzyloxycarbonyl group or a pyridinepropionyl group; V represents a natural amino acid or not chosen from among norleucine, norvaline and 2-N-Me-norleucine, X represents a natural amino acid or not having an aromatic character chosen from among phenylalanine, 1-naphtylalanine, 2-naphtylalanine, phenylglycine, benzothienylalanine, 4,4'-biphenylalanine, 3,3-diphenylalanine, homophenylalanine, indanylglycine, 4-methylphenylalanine, thienylalanine, p-nitrophenylalanine, halogenophenylalanine of configuration L or D; Y represents a natural amino acid of configuration L, having a basic character chosen from among arginine, lysine or ornithine, the enantiometers or diastereoisomers, and the mixtures thereof, including racemic mixtures. The invention also relates to a method for the preparation and application thereof in the field of therapeutics or cosmetics.

L'invention concerne des Peptide répondant à la formule (1) R-V l-Ala2-His3-X4- Y5-Trp 5-NH2 (1) dans laquelle R représente un atome d'hydrogène ou un groupe protecteur pouvant être choisi parmi un groupe acétyle, un groupe benzoyle, un groupe tosyle, un groupe benzène sulfonyle, un groupe benzyloxycarbonyle ou un groupe pyridinepropionyle; V représente un acide aminé naturel ou non choisi parmi la norleucine, la norvaline et la 2-N-Me-norleucine, X représente un acide aminé naturel ou non à caractère aromatique choisi parmi phénylalanine, 1-naphtylalanine, 2-naphtylalanine, phénylglycine, benzothiénylalanine, 4,4'- biphénylalanine, 3,3-diphénylalanine, homophénylalanine, indanylglycine, 4- méthylphénylalanine, thiénylalanine, p-nitrophénylalanine, halogénophénylalanine de configuration L ou D; Y représente un acide aminé naturel de configuration L, à caractère basique choisi parmi arginine, lysine ou ornithine, leurs énantiomères ou diastéréoisomères, ainsi que leurs mélanges, y compris les mélanges racémiques. Procédé de préparation et application en thérapeutique et en cosmétique.

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