Anticoagulant peptides

Details Anticoagulant peptides Anticoagulant peptides

C - Chemistry, Metallurgy

07

K

C07K 14/815 (2006.01) A61K 38/08 (2006.01) A61K 38/10 (2006.01) A61K 38/58 (2006.01) C07K 7/04 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2026376

This invention relates to a peptide derivative of the formula X-A1-A2-A3-A4-A5-A6-A7-A8-A9-A10-Y wherein X is an amino terminal residue selected from hydrogen, one or two alkyl groups of from 1 to 10 carbon atoms, one or two aryl groups of from 2 to 10 carbon atoms, carboben- zyloxy or t-butyloxy carbonyl; A1 is sequences of hirudin or its natural variants or por- tions thereof, a bond, or is a peptide containing from 1 to 11 residues of any amino acid; A2 is a bond or is Phe, SubPhe, pChoroPhe, D-Phe, NMePhe, Pgl, Tha, His, Cin, Nap, Leu, Gln, 3,4-dihydroCin, .beta.-(2- and 3-thienyl)alanine, .beta.-(2- and 3-furanyl)alanine, .beta.-(2-, 3- and 4-pyridyl)alanine, .beta.-(benzothienyl-2- and 3-)alanine, .beta.-(1- and 2-naphthyl)alanine, Tyr or Trp; A3 is a bond, or is Glu, Asp or Ala; A4 is a bond, or is any amino acid; A5 is a bond, or i.s Ile, Val, Leu, Nle, Phe, Ala or D-Leu; A6 is a bond, or is Pro, Hyp, 3,4-dihydroPro, thiazolidine- 4-carboxylate, Sar, NMePgl, Azt, Pip, Ala or D-Ala; A7 is a bond, or is any amino acid; A8 is a bond, or is any amino acid; A9 is a bonds or is a Tyr, I-Tyr, D-Tyr, His, Ala, Met, Trp, Phe, Leu, Nle, Ile, Val, Cha and Pro or is a dipeptide containing at least one of these amino acids or lipo- philic amino acids; A10 is sequences of hirudin or its natural variants or por- tions thereof, a bond, or is a peptide containing from 1 to 11 residues of any amino acid; Y is a carboxy terminal residue selected from OH, (C1-C8) alkoxy, amino, mono- or di-(C1-C4) alkyl substituted amino acids, or Y is an alcohol terminal residue; and where at least one of the positions in A3 through A9 is a bond; which is useful as an anticoagulant.

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