Separation material

Patent metadata

Field	Value
Publication number	US-9844621-B2
Application number	US-201214236921-A
Country	US
Kind code	B2
Filing date	Aug 7, 2012
Priority date	Aug 8, 2011
Publication date	Dec 19, 2017
Grant date	Dec 19, 2017

Abstract

A separation material includes a matrix that is bound to a saccharide, enabling the separation from a liquid of substances that selectively bind the saccharide. A method for preparing the separation material and a method for separating substances from a liquid that selectively bind a saccharide of the separation material are also described. A device employs the separation material for separating from a liquid substances that selectively bind to the saccharide of the separation material.

First claim

The invention claimed is:

1. A separation material of formula (VI) for selective separation of a blood group A determinant and/or a blood group B determinant from blood, blood plasma, or a blood product

wherein
saccharide represents a blood group A determinant and/or a blood group B determinant;
R 1 represents, independently of one another, straight- chain or branched C 1 -C 10 alkyl, wherein the alkyl group can be unsubstituted, or substituted with at least one substituent, selected from the group of substituents comprising halogen, alkyl, alkoxy, haloalkyl, cyano, nitro, amino, amidino, hydroxy, thiol, acylamino, alkoxycarbonylamino, haloalkoxycarbonylamino or alkylsulfonylamino;
R a represents —H, methyl or ethyl;
K represents —CO—, —NH— or —CH 2 —;
L represents —CH 2 —, —NH— or —O—;
R b represents, independently of one another, straight-chain or branched C 1 -C 10 alkyl such as methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, n- pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl or n- decyl, wherein the alkyl group can be unsubstituted, or substituted with at least one suitable substituent, selected from the group of substituents consisting of halogen, alkyl, alkoxy, haloalkyl, cyano, nitro, amino, amidino, hydroxy, thiol, acylamino, alkoxycarbonylamino, haloalkoxycarbonylamino or alkylsulfonylamino;
F 2 represents —NH—, —CH 2 —, —C(O)—, —N═, —O—, —CH═, —CH(OH)—or CH 2 —CH(OH)—;
c and d independently of each other represent 0 or 1;
M 1 represents —NH—, —CH 2 —, —C(O)—, —N═, —O— or —CH═;
R 2 represents, independently of one another, straight-chain or branched C 1 -C 10 alkyl, wherein the alkyl group can be unsubstituted, or substituted with at least one suitable substituent, selected from the group of substituents consisting of halogen, alkyl, alkoxy, haloalkyl, cyano, nitro, amino, hydroxy, thiol, acylamino, alkoxycarbonylamino, haloalkoxycarbonylamino or alkylsulfonylamino;
R 3 represents, independently of each other, —CO—NH—, —NH—CO—, —CO—NH—NH—, —NH—NH—CO—, —CH═N—NH—, —NH—N═CH—, —N═CH—, —CH═N — or triazolyl,
r represents 0 or an integer from 1-10;
w represents —O—, —S—, —CH 2 — or —NR′—, wherein R′ represents H, or methyl;
x represents an integer from 1-50.

2. A method for producing a separation material according to claim 1 , comprising
a) providing a matrix of the formula (I)
N 1 -matrix  (I),

wherein
N 1 represents H 2 N—, NH 2 —NH — or epoxy;
b) providing a thermally labile radical initiator of the formula (II)
HO 2 C—R 1 —Y—R 1 —CO 2 H  (II),

wherein
Y represents —N═N— or —O—O—, and
R 1 represents, independently of one another, straight-chain or branched C 1 -C 10 alkyl such as methyl, ethyl, n- or isopropyl, n-, iso- , sec- or tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl or n-decyl, wherein the alkyl group can be unsubstituted, or substituted with at least one suitable substituent, selected from the group of substituents consisting of halogen, alkyl, alkoxy, haloalkyl, cyano, nitro, amino, amidino, hydroxy, thiol, acylamino, alkoxycarbonylamino, haloalkoxycarbonylamino or alkylsulfonylamino ;
c) providing at least one polymerizable monomer of formula (III)
H 2 C═C(R a )—K-L-R b c —F 1 d   (III)

wherein
R a represents —H, methyl or ethyl,
K represents —CO—, —NH— or —CH 2 —,
L represents —H, —NH— or —O—,
R b represents, independently of one another, straight-chain or branched C 1 -C 10 alkyl such as methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl or n-decyl, wherein the alkyl group can be unsubstituted, or substituted with at least one suitable substituent, selected from the group of substituents consisting of halogen, alkyl, alkoxy, haloalkyl, cyano, nitro, amino, amidino, hydroxy, thiol, acylamino, alkoxycarbonylamino, haloalkoxycarbonylamino or alkylsulfonylamino,
c and d represent, independently of one another, 0 or 1, and
F 1 represents —OH, —NH 2 , —H, —N 3 , —CO 2 H, —CHO, —NH—NH 2 , —C≡CH or epoxy;
d) providing at least one saccharide having the formula (V)
saccharide-W—R 2 —(R 3 —R 2 ) r -M  (V),

wherein
W represents O, S, CH 2 or NR′, wherein R′ represents H, methyl or a suitable amino protecting group,
R 2 represents, independently of one another, straight-chain or branched C 1 -C 10 alkyl such as methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl or n-decyl, wherein the alkyl group can be unsubstituted, or substituted with at least one suitable substituent, selected from the group of substituents consisting of halogen, alkyl, alkoxy, haloalkyl, cyano, nitro, amino, hydroxy, thiol, acylamino, alkoxycarbonylamino, haloalkoxycarbonylamino or alkylsulfonylamino,
R 3 represents, independently of each other, —CO—NH—, —NH—CO—, —CO—NH—NH—, —NH—NH—CO—, —CH═N—NH—, —NH—N═CH—, —N═CH—, —CH═N— or triazolyl,
M represents —COOH, —NH 2 , —C≡C, —N 3 , —NH—NH 2 or —OH,
r represents 0 or an integer from 1-10;
e) coupling the matrix of formula (I) to the thermally labile radical initiator of formula (II),
f) reacting the resulting matrix surface with a solution of the at least one polymerizable monomer of formula (III) under conditions which allow thermally initiated graft copolymerization and/or polymerization of the at least one monomer, wherein functional polymer chains are created on the surface of the matrix, and
g) coupling the at least one saccharide of formula (V) to the functional polymer chains on the surface of the matrix.

3. The method of claim 2 further comprising providing a compound of formula (IV)
R 4A —R 2 —(R 4 —R 2 ) n -E 1   (IV),

wherein
R 2 is defined as in claim 1 ,
R 4 independently of one another represents —O—, —S—, —CO—NH—, —NH—CO—, —N═CH— or —CH═N—,
R 4A represents HOOC—, H 2 N—, C≡C, N 3 —, NH 2 —NH— or OH—,
E 1 represents —COOH, —CHO, —NH 2 , —SH, —OH, —N 3 , —NH—NH 2 or —C≡C,
n represents 0 or an integer from 1-600,
and wherein in step (g) the compound of formula (IV) is first attached via its terminal functional group to the functional polymer chains on the matrix, and the resulting product is then coupled to the saccharide of formula (V).

4. The method according to claim 3 wherein
N 1 represents H 2 N— or epoxy,
Y represents —N═N—,
K represents —CO— or —NH—,
R b represents, independently of one another, straight-chain or branched C 1 -C 10 alkyl such as methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl or n-decyl, wherein the alkyl group can be unsubstituted, or substituted with at least one suitable substituent, selected from the group of substituents comprising halogen, alkyl, alkoxy, haloalkyl, cyano, nitro, amino, amidino, hydroxyl or thiol,
c and d represent, independently of each other, 0 or 1,
W represents O, S or NR′, wherein R′ represents H, methyl or a suitable amino protecting group,
R 3 independently of one another represents —CO—NH—, —NH—CO—, —CO—NH—NH—, —NH—NH—CO—, —N═CH— or —CH═N—, and
M represents —COOH, —NH 2 , —C≡C, —N 3 or —NH—NH 2 .

5. The method according to claim 3 wherein
R 2 represents, independently of one another, straight-chain or branched C 1 -C 10 alkyl such as methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl or n-decyl, wherein the alkyl group can be unsubstituted, or substituted with at least one suitable substituent, selected from the group of substituents comprising halogen, alkyl, alkoxy, haloalkyl, cyano, nitro, amino, hydroxyl or thi

Assignees

• Rempfer Martin
• Freudemann Wolfgang
• Winz Cornelia
• Flieg Ralf
• Storr Markus
• Homeyer Sandra
• Knoer Torsten
• Gambro Lundia Ab

Inventors

• Rempfer Martin
• Freudemann Wolfgang
• Winz Cornelia
• Flieg Ralf
• Storr Markus
• Homeyer Sandra
• Knoer Torsten

Classifications

• B01J20/3212

  consisting of a polymer obtained by reactions otherwise than involving only carbon to carbon unsaturated bonds · CPC title

• B01J20/3274

  Proteins, nucleic acids, polysaccharides, antibodies or antigens · CPC title

• B01J20/3278

  Polymers being grafted on the carrier · CPC title

• B01J20/289

  bonded via a spacer · CPC title

• B01J20/3219

  involving a particular spacer or linking group, e.g. for attaching an active group · CPC title