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US4563445A
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3-Fucosyl-N-acetyl lactosamine derivatives, and their biological applications
Assignee: Choay SA
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Filing: 1984-01-09
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Granted: 1986-01-07
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Expires: 2004-01-09
Abstract
Abstract The invention relates to substitution derivatives of trisaccharide 3-fucosyl-N-acetyl lactosamine and to the immunological applications of these derivatives and of the trisaccharide itself particularly as diagnostic reagent and in therapy.
Inventors
- 👤 Ten Feizi
- 👤 Hock C. Gooi
- 👤 Pierre G. Sinay
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 17:23
CPC Classifications
C; C07; C07H; C07H13/00; C07H13/02; C07H13/04; C07C; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/178; C07C43/1785; C07H15/00; C07H15/02; C07H15/04; C07H15/08; C07H3/00; C07H3/06; C07K; C07K16/00; C07K16/18; G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/53; G01N33/531; A; A61; A61K; A61K38/00
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
145 words
Trisaccharides of the formula: ##STR32## wherein A is a hydroxy-alkyl group of 2 to 10 carbon atoms, an alkenyl group of 2 to 10 carbon atoms or one of the following substituents: (1):-- (CH.sub.2).sub.n --O--(CH.sub.2).sub.n' --O--(CH.sub.2).sub.m --R (2):-- (CH.sub.2).sub.n" --O--(CH.sub.2)m'--R (3):-- (CH.sub.2).sub.n" --R wherein --n,n' and m, are identical or different each from other and are equal to 1,2,3,4 or 5, with m being further equal to 0, --n" and m' are identical or different each from other, being equal to 1,2,3,4 or 5 with m' being further equal to 0, n"+m' (where m' is not 0) being an integer from 4 to 10, --n"' is an integer from 1 to 10 and --R is hydrogen, where m=0 in (1), OH, and COOR' wherein R' is alkyl or alkenyl of 2-10 carbon atoms, --COOH, --CONH 2 N 3 or --NH 2 and B is hydrogen.
Claim 2
Dependent Claim
145 words
Trisaccharides of the formula: ##STR32## wherein A is a hydroxy-alkyl group of 2 to 10 carbon atoms, an alkenyl group of 2 to 10 carbon atoms or one of the following substituents: (1):-- (CH.sub.2).sub.n --O--(CH.sub.2).sub.n' --O--(CH.sub.2).sub.m --R (2):-- (CH.sub.2).sub.n" --O--(CH.sub.2)m'--R (3):-- (CH.sub.2).sub.n" --R wherein --n,n' and m, are identical or different each from other and are equal to 1,2,3,4 or 5, with m being further equal to 0, --n" and m' are identical or different each from other, being equal to 1,2,3,4 or 5 with m' being further equal to 0, n"+m' (where m' is not 0) being an integer from 4 to 10, --n"' is an integer from 1 to 10 and --R is hydrogen, where m=0 in (1), OH, and COOR' wherein R' is alkyl or alkenyl of 2-10 carbon atoms, --COOH, --CONH 2 N 3 or --NH 2 and B is hydrogen.
Claim 3
Dependent Claim
15 words
Trisaccharides according to claim 1 wherein, the sum n+n'+m is an integer equal to 8.
Claim 4
Dependent Claim
20 words
Trisaccharides according to claim 1, comprising an A substituent of structure (1) or (2) wherein R is a hydrogen atom.
Claim 5
Dependent Claim
39 words
Trisaccharides according to claim 1, wherein A is a chain having structure (1), (2) or (3), R is a --COOR', where R' is an alkyl group with 2 or 3 carbon atoms, or R is a --CONH 2 group.
Claim 6
Dependent Claim
26 words
Trisaccharides according to claim 1 wherein R is a nitrogenous group selected from the group consisting of --NH 2 , --N 3 or --NH--NH 2 .
Claim 7
Dependent Claim
25 words
Trisaccharides according to claim 1 wherein A is the substituent (1) or (2) wherein --R is an alkenyl group of 2 to 10 carbon atoms.
Claim 8
Dependent Claim
17 words
Trisaccharides according to claim 1 wherein n"+m' is equal to 8 provided m' is other than 0.
Claim 9
Dependent Claim
14 words
Trisaccharides according to claim 1 wherein n"' is an integer from 4 to 10.
Claim 10
Dependent Claim
19 words
Trisaccharides according to claim 1 wherein A has the structure (1) or (2) and R is an allyl group.
Claim 11
Dependent Claim
27 words
Trisaccharides according to claim 1 selected from the group consisting of 8-azido-3,6-dioxaoctyl 2-acetamido-3-O [α-L-fucopyranosyl]-4-O [β-D-galactropyranosyl]-2-deoxy-β-D-glycopyranoside; 8-amino 3,6-dioxaoctyl 2 acetamido-3-O [α-L-fucopyranosyl]-4-O-[β-galactopyranosyl]-2-deoxy-β-D-glucopyranoside; 8-methoxy carbonyl octyl 3,6-dioxa 2-acetamido 3-O-[αL -fucopyranosyl]-4-O[β-D-galactopyranosyl]2-deoxy-β-D-glucopyranoside.
Claim 12
Dependent Claim
23 words
An immunological reagent which comprises a reactively effective and detectable amount of trisaccharide according to claim 1 in admixture with a suitable carrier.
Claim 13
Dependent Claim
23 words
A diagnostic reagent which comprises a reactively effective and detectable amount of trisaccharide according to claim 1 in admixture with a suitable carrier.
Claim 14
Dependent Claim
26 words
An artificial antigen composition which comprises a reactively effective and detectable amount of trisaccharide according to claim 1 fixed to a suitable water soluble macromolecular support.
Claim 15
Dependent Claim
24 words
An immunoabsorbant composition which comprises a reactively effective and detectable amount of trisaccharide according to claim 1 fixed to a suitable insoluble macromolecular support.
Claim 16
Dependent Claim
32 words
Antibodies specific with respect to a trisaccharide according to claim 1 formed by a predetermined immunologically active system in response to contact with a trisaccharide according to claim 1 or 3-fucosyl-N-acetyl lactosamine.
Claim 17
Dependent Claim
38 words
A method of detecting anti-3-fucosyl-N-acetyl lactosamine antibodies in serum which comprises contacting the serum to be tested with the artificial antigen composition according to claim 13 or 3-fucosyl-N-acetyl lactosamine and observing the presence or absence of antibody/antigen reaction.
Claim 18
Dependent Claim
46 words
A method of detecting the localizing in vivo gastro intestinal tumors which comprises administering to the host respected of having such tumors, antibodies according to claim 15 labeled with a physiologically acceptable radioactive tracer and observing the location of areas of elevated radioactivity in said subject.
Claim 19
Dependent Claim
44 words
An immunoabsorbant composition which comprises a reactively effective and detectable amount of trisaccharide according to claim 1 fixed to a suitable water insoluble macromolecular support selected from the group consisting of cellulose, agarose or recticulated agarose, silica, glass, latex beads and copolymers of polyacrylamide.
Claim 20
Dependent Claim
33 words
An artificial antigen composition which comprises a reactively effective and detectable amount of trisaccharide according to claim 1 fixed to a suitable water soluble macromolecular support wherein the said support is a protein.
Claim 21
Dependent Claim
21 words
A composition according to claim 19, wherein the protein is selected from poly-L-alanine, -lysine, albumin, bovin serum albumin, thyroglublin and polylysine.
References Cited (Backward Citations)
US4137401A
Cited
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