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Cinnamic acid derivative

  • US 6,025,444 A
  • Filed: 05/27/1997
  • Issued: 02/15/2000
  • Est. Priority Date: 11/17/1994
  • Status: Expired due to Term
First Claim
Patent Images

1. A cinnamic acid-polysaccharide derivative represented by any of the formulas (13)-(15):

  • 
    
    space="preserve" listing-type="equation">R.sup.1 --A--P.sup.1 (

         13)
    
    
    space="preserve" listing-type="equation">R.sup.1 --B--P.sup.2 (

         14)
    
    
    space="preserve" listing-type="equation">R.sup.2 --C--P.sup.1 (

         15)wherein R1 represents a group of the formula (4);

    ##STR21## wherein R3 and R4 independently represent a hydrogen atom, a nitro group, an amino group hydroxyl group or a C1-4 alkoxy group;

    R2 represents a group of the formula (5);

    ##STR22## wherein R3 and R4 are as defined above;

    R5 represents a lower alkyl group;

    --A represents an amino- and hydroxy-containing compound residue represented by any of the formulas (6'"'"')-(9'"'"');

    
    
    space="preserve" listing-type="equation">--O--(CH.sub.2).sub.n --NH (6'"'"')wherein n represents a whole number of 3-18,
    
    
    space="preserve" listing-type="equation">--(O--CH.sub.2 CH.sub.2).sub.m --NH (7'"'"')wherein m represents a whole number of 2-10,
    
    
    space="preserve" listing-type="equation">--O--CHR.sup.6 CH(COOR.sup.7)--NH (8'"'"')wherein R6 represents a hydrogen atom or a lower alkyl group;

    R7 represents a lower alkyl group,
    
    
    space="preserve" listing-type="equation">--O--(CH.sub.2).sub.l --NHCO--CHR.sup.8 --NH (9'"'"')wherein l represents a whole number of 2-18;

    R8 represents the side chain of an α

    -amino acid residue;

    --B represents an amino acid residue of the formula (10'"'"');

    
    
    space="preserve" listing-type="equation">--NH--(CH.sub.2).sub.k --CO (10'"'"')wherein k represents a whole number of 1-18;

    --C represents an amino acid residue of the formula (11'"'"') or (12'"'"');

    
    
    space="preserve" listing-type="equation">--CO--(CH.sub.2).sub.k --NH (11'"'"')wherein k is as defined above,
    
    
    space="preserve" listing-type="equation">--(COCHR.sup.8 NH).sub.i ( 12'"'"')wherein i represents a whole number of 1-6;

    R8 is as defined above;

    P1 represents a carboxy-containing polysaccharide residue;

    P2 represents a hydroxy-containing polysaccharide residue; and

    the A--P1 linkage is the amide bond between the terminal amino residue of the formula (6'"'"'), (7'"'"'), (8'"'"') or (9'"'"') and the carboxyl residue of P1 ;

    the B--P2 linkage is the ester bond formed between the terminal carboxyl residue of the formula (10'"'"') and the hydroxyl residue of P2 ; and

    the C--P1 linkage is the amide bond between the terminal amino residue of the formula (11'"'"') or (12'"'"') and the carboxyl residue of P1 ;

    with the provisos that the polysaccharide is a hyaluronic acid and the photodimerizable-crosslinkable group is introduced into the cinnamic acid-polysaccharide derivative at a degree of substitution of 0.05-5.0% to a repeating constituent saccharide unit of the hyaluronic acid.

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