DERIVATIVES OF AMIDINOPHENYLALANINE, METHOD OF THEIR SYNTHESIS AND AMIDINOPHENYLALANINE DERIVATIVES SHOWING ANTICOAGULATING ACTIVITY Russian patent published in 1997 - IPC

FIELD: organic chemistry, amino acid derivatives. SUBSTANCE: product: derivatives of amidinophenylalanine of the formula (I): R-SO₂-NH-CHR-CO-NH-CH(CH₂C₆H₄CNHNH₂)CONR₂R₃ where: R - naphthalene ring bound at α- or b-position that if necessary can be substituted one or twice with alkoxy-(C₁- C₃)-group, or tetraline ring bound at β-position, or phenyl ring that if necessary can be substituted at 2, 3, 6 positions with (C₁- C₄)-alkyls, at 4 position - with (C₁- C₄)-alkoxy-group; R₁ - the group A-B where A - -(CH₂)_n - ; n = 1-4; β-group is -COOH or SO₃H, or R₁ - the group A-B-C where values A and β were indicated above, and the group C is formed from N-bound beta- or gamma-amino acid or from the group N-glycoside-bound uronic acids, or R₁ - tetrazole; R₂ and R₃ together with nitrogen atom form piperidyl, 3-hydroxy-(C₁- C₄)-alkylpiperidyl. Reagent 1: derivative of D-p-cyanophenylalanine: BOC--HNCH₂/C₆H₄CN/COONR₂R₃ and after BOC-group splitting off product is reacted with reagent 2: (tBu)HNCHR₁COOH and from the obtained product N-α-protective group is split off. Residue is treated with RSO₂Cl and in the obtained compound cyano-group is converted to amidino-group and protective groups were split off, if necessary. EFFECT: improved method of synthesis. 10 cl, 2 tbl