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| Nucleoside compounds |
| Where the following terms are used in this specification, they are used as defined below. The ... |
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| Where the following terms are used in this specification, they are used as defined below. The term ... |
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Phospholipid- or lipid-linked glycosaminoglycan and process for producing the same
| Details |
Inventors: Sakurai, Katsukiyo; Sugiura, Nobuo; Kimata, Koji; Suzuki, Sakaru;
Assignee: Seikagaku Kogyo Kabushiki Kaisha (Tokyo, JP)
Primary Examiner: Robinson; Douglas W.
Assistant Examiner: Fonda; Kathleeen Kahler
Attorney, Agent or Firm: Sughrue, Mion, Zinn, Macpeak & Seas
This invention relates to compounds prepared by linking glycosaminoglycan to phospholipid or lipid, which are expected to exert a pharmacological effect for inhibiting metastasis because of their excellent function to inhibit adhesion of cancer cells to blood vessel endothelial cells and extracellular matrix. This phospholipid- or lipid-linked glycosaminoglycan can be produced for example by: cleaving and oxidizing reducing terminal group of glycosaminoglycan, and allowing an aldehyde group or a lactone compound of the thus-formed derivative or a carboxyl group in the glycosaminoglycan chain to react with a primary amino group of a phospholipid; or linking a glycosaminoglycan derivative to a phospholipid or a lipid by allowing a primary amino group of the derivative to react with a carboxyl group of the phospholipid or lipid. This phospholipid- or lipid-linked glycosaminoglycan is useful as a metastasis inhibitor because it has no toxicity. |
|
DETAILED DESCRIPTION What is claimed is: 1.
A process for producing a phospholipid- or lipid-linked glycosaminoglycan represented by the following formula (VI), ##STR122## or a salt thereof, which comprises the steps of: (a) reacting an aldehyde compound represented by the following formula (II-3) ##STR123## with an alkylene diamine thereby obtaining a compound of formula (16) ##STR124## wherein (1) R.
sup.
1 is --NHCOCH.
sub.
3 and R.
sup.
3 is an --OH group when GAG is a glycosaminoglycan residue of hyaluronic acid or chondroitin, wherein the reducing terminal hexosamine thereof has been removed, (2) R.
sup.
1 is --NHCOCH.
sub.
3 and R.
sup.
3 is an --OSO.
sub.
3 H group when GAG is a glycosaminoglycan residue of chondroitin sulfate A or K, chondroitin polysulfate or dermatan sulfate, wherein the reducing terminal hexosamine moiety thereof has been removed, and (3) each of R.
sup.
1 and R.
sup.
3 is an --OH group when GAG is a glycosaminoglycan residue of keratan sulfate or keratan polysulfate, wherein the reducing terminal galactose moiety thereof has been removed, and m is an integer of 1 to 8 and l is an integer of 1 to 10; (b) separately reacting a phospholipid or lipid (P.
sup.
2), wherein P.
sup.
2 is a phospholipid or a lipid represented by the following formulae: ##STR125## wherein R.
sup.
8 is hydrogen, R.
sup.
9 is an alkyl group, R.
sup.
10 is --CH.
dbd.
CHR.
sup.
6 or --COR.
sup.
7, wherein each of R.
sup.
6 and R.
sup.
7 is a C.
sub.
6-24 alkyl group, m is an integer of 1 to 8 and l is an integer of 1 to 10, and X is --CH.
sub.
2 CH.
sub.
2 N.
sup.
+ (CH.
sub.
3).
sub.
3 or an inositol residue, and GAG is a glycosaminoglycan residue of hyaluronic acid, chondroitin, chondroitin sulfate A, chondroitin sulfate K, chondroitin polysulfate, dermatan sulfate, keratan sulfate or keratan polysulfate, with a dicarboxylic acid or a dicarboxylic acid anhydride to obtain a phospholipid or lipid having a carboxyl group; and (c) reacting a primary amino group in the resulting compound of formula (16) with the resulting carboxyl group in the phospholipid or lipid
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