US4810784A
Expired / Lapsed
US
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Process for covalent coupling for the production of conjugates, and products hereby obtained
Assignee: Individual
•
Filing: 1987-09-17
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Granted: 1989-03-07
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Expires: 2007-09-17
Abstract
Abstract A process to produce by covalent binding conjugates of a substance containing a 2-amino-2-deoxyglycopyranosyl residue the NH 2 -function of which in its most stable conformation is equatorially oriented, and a substrate containing a primary amino group. This is done by subjecting the substrate to degradation by diazotation to form a substance fragment having a free terminal aldehyde group, said fragment through its aldehydo group being reacted with the amino group of the substrate to form a Schiffs base which is then by reduction converted to a secondary amine. The substance is preferably selected from oligo and polysaccharides containing glucosamine or galactose amine units. The substrate is suitably selected from surface-aminated plastic objects, aminated gels and proteins. The conjugate described consists of an 1-deoxy-2,5-anhydrohexitol unit which constitutes terminal unit in an oligo or polysaccharide and which in 1-position is covalently bound to an amino group associated with a substrate.
Inventors
- 👤 Olle Larm
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 17:36
CPC Classifications
C; C08; C08B; C08B37/00; C08B37/006; C08B37/0063; C08B37/0075; A; A61; A61L; A61L33/00; A61L33/0005; A61L33/0011; A61L33/0029; A61L33/06; A61L33/08; A61P; A61P7/00; A61P7/02; B; B01; B01J; B01J20/00; B01J20/30; B01J20/3085; B01J20/32; B01J20/3202; B01J20/3206; B01J20/3208; B01J20/321; B01J20/3212; B01J20/3214; B01J20/3217; B01J20/3231; B01J20/3242; B01J20/3268; B01J20/3272; B01J20/3274; B01J20/3289; C08B37/0006; C08B37/0024; C08B37/0027; B01J2220/00; B01J2220/50; B01J2220/58; B01J2220/64
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
81 words
A process to produce by covalent binding conjugates of a substance containing a 2-amino-2-deoxy-glycopyranosyl unit the NH 2 -function of which in its most stable conformation is equatorially oriented, and a substrate containing a primary amino group, comprising degrading said substance by diazotation to form a substance fragment having a free terminal aldehyde group, reacting said fragment through its aldehyde group with the amino group of the substrate to form a Schiff's base, and reducing the base to a secondary amine.
Claim 2
Dependent Claim
81 words
A process to produce by covalent binding conjugates of a substance containing a 2-amino-2-deoxy-glycopyranosyl unit the NH 2 -function of which in its most stable conformation is equatorially oriented, and a substrate containing a primary amino group, comprising degrading said substance by diazotation to form a substance fragment having a free terminal aldehyde group, reacting said fragment through its aldehyde group with the amino group of the substrate to form a Schiff's base, and reducing the base to a secondary amine.
Claim 3
Dependent Claim
25 words
A process according to claim 1, wherein the diazotation is performed in aqueous solution with an agent having the ability to form NO + -ions.
Claim 4
Dependent Claim
24 words
The process according to claim 2 wherein the reaction of aldehydo and amino groups is performed in an organic solvent or an aqueous solution.
Claim 5
Dependent Claim
23 words
The process according to claim 2 wherein the agent has the ability to form NO + -ions in sodium nitrite or butyl nitrite.
Claim 6
Dependent Claim
24 words
A process according to claim 1 wherein the reaction of aldehydo and amino groups is performed in an organic solvent or an aqueous solution.
Claim 7
Dependent Claim
17 words
A process according to claim 1 wherein the reduction of the Schiff's base is performed with cyanoborohydride.
Claim 8
Dependent Claim
20 words
A process according to claim 1 wherein said substance is selected from oligo or polysaccharides containing glucosamine or galactosamine residues.
Claim 9
Dependent Claim
30 words
A process according to claim 7 wherein said substance is selected from heparin and heparin derivatives, at least partially deacetylated dermatan sulfate, chitosan and at least partially deacetylated hyaluronic acid.
Claim 10
Dependent Claim
19 words
A process according to claim 1 wherein the substrate is selected from surface-aminated plastic objects, aminated gels and proteins.
Claim 11
Dependent Claim
12 words
A process according to claim 1 wherein said substance possesses biological activity.
Claim 12
Dependent Claim
39 words
A conjugate comprising a substrate and, attached thereto, an oligo or polysaccharide, said saccharide having as a terminal unit a 1-deoxy-2,5-anhydrohexitol entity, said entity being covalently bound in the 1-position thereof to an amino group associated with the substrate.
Claim 13
Dependent Claim
39 words
A conjugate comprising a substrate and, attached thereto, an oligo or polysaccharide, said saccharide having as a terminal unit a 1-deoxy-2,5-anhydrohexitol entity, said entity being covalently bound in the 1-position thereof to an amino group associated with the substrate.
Claim 14
Dependent Claim
14 words
The conjugate according to claim 11 wherein the hexitol entity is a mannitol unit.
Claim 15
Dependent Claim
13 words
The conjugate according to claim 12 wherein the polysaccharide is derived from chitosan.
Claim 16
Dependent Claim
17 words
The conjugate according to claim 12 wherein the substrate is selected from plastic objects, gels and proteins.
Claim 17
Dependent Claim
13 words
The conjugate according to claim 12 wherein the polysaccharide is derived from heparin.
Claim 18
Dependent Claim
17 words
The conjugate according to claim 15 wherein the substrate is selected from plastic objects, gels and proteins.
Claim 19
Dependent Claim
14 words
The conjugate according to claim 15 wherein the polysaccharide is derived from hyaluronic acid.
Claim 20
Dependent Claim
17 words
The conjugate according to claim 17 wherein the substrate is selected from plastic objects, gels and proteins.
Claim 21
Dependent Claim
14 words
The conjugate according to claim 11 wherein the hexitol entity is a talitol entity.
Claim 22
Dependent Claim
14 words
The conjugate according to claim 19 wherein the polysaccharide is derived from dermatan sulfate.
Claim 23
Dependent Claim
17 words
The conjugate according to claim 11 wherein the substrate is selected from plastic objects, gels and proteins.
Claim 24
Independent Claim
99 words
A method of attaching a substance containing a 2-amino-2-deoxyglycopyranosyl unit, the NH 2 -function of which in its most stable conformation is equatorially oriented, to a substrate containing a primary amino group, wherein said substance is selected from the group consisting of heparin, deacetylated dermatan sulfate, chitosan, deacetylated hyaluronic acid, and biologically active derivatives thereof, comprising degrading said substance by diazotation to form a substance fragment having a free terminal aldehyde group, reacting said fragment through its aldehyde group with the amino group of the substrate to form a Schiff's base, and reducing the base to a secondary amine.
Claim 25
Independent Claim
99 words
A method of attaching a substance containing a 2-amino-2-deoxyglycopyranosyl unit, the NH 2 -function of which in its most stable conformation is equatorially oriented, to a substrate containing a primary amino group, wherein said substance is selected from the group consisting of heparin, deacetylated dermatan sulfate, chitosan, deacetylated hyaluronic acid, and biologically active derivatives thereof, comprising degrading said substance by diazotation to form a substance fragment having a free terminal aldehyde group, reacting said fragment through its aldehyde group with the amino group of the substrate to form a Schiff's base, and reducing the base to a secondary amine.
Claim 26
Dependent Claim
25 words
The method according to claim 22 wherein the diazotation is performed in aqueous solution with an agent having the ability to form NO + -ions.
Claim 27
Dependent Claim
24 words
The method according to claim 22 wherein the reaction of aldehydo and amino groups is performed in an organic solvent or an aqueous solution.
Claim 28
Dependent Claim
17 words
The method according to claim 22 wherein the reduction of the Schiff's base is performed with cyanoborohydride.
References Cited (Backward Citations)
US2016962A
Cited
US2918462A
Cited
US3673612A
Cited
SE365710B
Cited
US3826678A
Cited
FR2250795A1
Cited
US3947352A
Cited
FR2309245A1
Cited
SE400173B
Cited
US4118485A
Cited
GB2041377A
Cited
US4301067A
Cited
US4329383A
Cited
US4424346A
Cited
US4613665A
Cited
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