Anticoagulant peptides

Details Anticoagulant peptides Anticoagulant peptides

C - Chemistry, Metallurgy

07

K

C07K 7/08 (2006.01) A61K 38/03 (2006.01) A61K 38/08 (2006.01) A61K 38/10 (2006.01) A61K 38/58 (2006.01) C07K 4/12 (2006.01) C07K 7/06 (2006.01) C07K 14/815 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2086243

This invention relates to peptide analogs of the form- ula X-A1-A2-A3-A4-A5-A6-A7-A8-A9-A10-A11-A12-Y wherein X is an amino terminal residue selected from hydro- gen, one or two alkyl groups of from 1 to 6 carbon atoms, one or two acyl groups of from 2 to 10 car- bon atoms, carbobenzyloxy, H2NC(=NH)-, or a t- butyloxy carbonyl group; A1 is a band or is a peptide fragment containing from 1 to 11 residues of any ammo acid; A2 is a bond or is a group of the formula (see formula I) wherein Y2 = O, NR2', S, bond, Z2 = -SO3H, (see formula II), -COOR2", n is an integer of from 1 to 5 and wherein R2' and R2" are each independently an H or a (C1-C4)alkyl group; A3 is Phe, SubPhe, .beta.-(2- and 3-thienyl)alanine, .beta.-(2- and 3-furanyl)alanine, .beta.-(2-, 3- and 4-pyridyl)ala nine, .beta.-benzothienyl-2- and 3-yl)alanine, .beta.-(1- and 2-naphthyl)alanine, Tyr, Tyr(Me) and Trp; A4 is a bond or is a group of the formula (see formula III) wherein Y4 = bond O, NR4', S, Z4 = -SO3H, COOR4", (see formula IV), m is an integer of 1 to 5 and wherein R4' and R4" are each independently an H or a (C1-C4)- alkyl group; A5 is any amino acid; A6 is Tyr, Trp, Phe, Leu, Nle, Ile, Val, Cha or Pro; A7 is Pro, Ser, Ala or Thr; A8 is Tyr, tyr, Trp, trp, Phe, phe, Leu, leu, Nle, nle, Ile, ile, Va.l, val, Cha, cha, Pro or pro; A9 is any amino acid; A10 is any amino acid; A11, is Tyr, Trp, Phe, Leu, Nle, Ile, Val, Cha and Pro; A12 is a bond or is a peptide fragment containing from one to ten residues of any amino acid; and Y is a carboxy terminal residue selected from OH, C1- C6 alkoxy, amino, mono- or di-(C1-C4)alkyl substi- tuted amino, or benzylamino; or a pharmaceutically acceptable salt thereof, which are use- ful as anticoagulant agents.

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