Cinnamic acid derivative
First Claim
Patent Images
1. A cinnamic acid-polysaccharide derivative represented by any of the formulas (13)-(15):
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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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Abstract
The invention provides a cinnamic acid derivative having a novel spacer introduced into cinnamic acid which is photodimerizable, a cinnamic acid-polysaccharide derivative photocurable with high sensitivity and efficiency obtainable by introducing the above cinnamic acid derivative into a host polysaccharide such as a glycosaminoglycan, and a photocrosslinked cinnamic acid-polysaccharide derivative obtainable by exposing the same cinnamic acid-polysaccharide derivative to ultraviolet light irradiation.
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Citations
5 Claims
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1. A cinnamic acid-polysaccharide derivative represented by any of the formulas (13)-(15):
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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; andthe 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. - View Dependent Claims (2, 3, 4, 5)
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Specification