Non-pressurized methods for the preparation of conjugrated solid supports for boronic acids
First Claim
Patent Images
1. A method for preparing a dihydroxyalklylaminoalkyl or a dihydroxyaminobenzyl-conjugated solid support under non-pressurized conditions comprising the following steps:
- (a) providing an alkyl halide, a substituted alkyl halide or a benzyl halide conjugated to a solid support, wherein the alkyl halide has a formula —
(CH2)m—
X and m is an integer between 1 to about 20, and X is the halide and is chloride, bromide, iodide or an equivalent thereof;
(b) providing a composition comprising a secondary amine comprising two hydroxyalkyl substituents, wherein the composition has a formula HO(CH2)xHN(CH2)yOH and x and y are integers between 1 to about 20;
(c) providing a halide salt selected from the group consisting of an iodide salt, a bromide salt and equivalents thereof; and
, (d) mixing the conjugated solid support of step (a) with the composition of step (b) and the halide salt of step (c) under non-pressurized conditions, thereby forming a dihydroxyalkylaminoalkyl or a dihydroxyaminobenzyl-conjugated solid support.
1 Assignment
0 Petitions
Accused Products
Abstract
The methods of the invention are directed to preparation of dihydroxyalkylaminoalkyl-conjugated solid supports, such as a diethanolamine- or a dipropanolamine-conjugated resin or polystyrene under non-pressurized conditions. The invention also provides novel methods for immobilizing boronic acids. The invention also provides a novel class of solid supports comprising dihydroxyalkyl-aminoalkyl groups
-
Citations
73 Claims
-
1. A method for preparing a dihydroxyalklylaminoalkyl or a dihydroxyaminobenzyl-conjugated solid support under non-pressurized conditions comprising the following steps:
-
(a) providing an alkyl halide, a substituted alkyl halide or a benzyl halide conjugated to a solid support, wherein the alkyl halide has a formula —
(CH2)m—
X and m is an integer between 1 to about 20, and X is the halide and is chloride, bromide, iodide or an equivalent thereof;
(b) providing a composition comprising a secondary amine comprising two hydroxyalkyl substituents, wherein the composition has a formula HO(CH2)xHN(CH2)yOH and x and y are integers between 1 to about 20;
(c) providing a halide salt selected from the group consisting of an iodide salt, a bromide salt and equivalents thereof; and
,(d) mixing the conjugated solid support of step (a) with the composition of step (b) and the halide salt of step (c) under non-pressurized conditions, thereby forming a dihydroxyalkylaminoalkyl or a dihydroxyaminobenzyl-conjugated solid support. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 73)
-
-
40. A method for preparing a diethanolaminomethyl-conjugated solid support under non-pressurized conditions comprising the following steps:
-
(a) providing a chloromethylated polystyrene solid support;
(b) providing diethanolamine;
(c) providing a halide salt, wherein the halide salt comprises sodium iodide or an equivalent thereof; and
,(d) mixing the chloromethylated polystyrene solid support of step (a) with the diethanolamine of step (b) and the halide salt of step (c) under non-pressurized conditions, thereby forming the diethanolaminomethyl-conjugated solid support. - View Dependent Claims (41)
-
-
42. A method for preparing a dihydroxyalkylaminoalkyl-conjugated solid support under non-pressurized conditions comprising the following steps:
-
(a) providing a solid support conjugated with a primary amino group;
(b) providing a composition comprising a halogenated alcohol, wherein the composition has a formula HO(CH2)xY and x is an integer between 1 to about 20 and Y is a halide selected from the group consisting of chloride, bromide, and iodide and equivalents thereof;
(c) providing a halide salt selected from the group consisting of an iodide salt or a bromide salt or an equivalent thereof;
(d) providing a base; and
(e) mixing the conjugated solid support of step (a) with the composition of step (b) and the halide salt of step (c) and the base of step (d) under non-pressurized conditions, thereby forming a dihydroxyalkylaminoalkyl-conjugated solid support. - View Dependent Claims (43, 44, 45, 46, 47)
-
-
48. A method for making a solid-supported boronic acid ester comprising the following steps:
-
(a) providing a conjugated solid support prepared by the following steps;
(i) providing an alkyl halide or a substituted alkyl halide or a benzyl halide conjugated to a solid support, wherein the alkyl halide has a formula —
(CH2)m—
X and m is an integer between 1 to about 20, and X is the halide and is chloride, bromide, iodide, or an equivalent thereof;
(ii) providing a composition comprising a secondary amine comprising two hydroxyalkyl substituents, wherein the composition has a formula HO(CH2)xHN(CH2)yOH and x and y are integers between 1 to about 20;
(iii) providing a halide salt, wherein the halide salt is a bromide salt, an iodide salt, or an equivalent thereof; and
,(iv) mixing the conjugated solid support of step (i) with the composition of step (ii) and the halide salt of step (iii) under non-pressurized conditions, thereby forming a dihydroxyalkylaminoalkyl conjugate;
(b) providing a boronic acid solution; and
(c) mixing the dihydroxyalkylaminoalkyl-conjugated solid support of step (a) with the boronic acid solution of step (b), thereby forming a solid-supported boronic acid ester. - View Dependent Claims (50, 51, 52, 53, 54)
-
-
49. A method for immobilizing a boronic acid comprising the following steps:
-
(a) providing a conjugate prepared by the following steps;
(i) providing an alkyl halide or a substituted alkyl halide or a benzyl halide conjugated to an solid support, wherein the alkyl halide has a formula —
(CH2)m—
X and m is an integer between 1 to about 20 and the halide is chloride, bromide, iodide, or an equivalent thereof;
(ii) providing a composition comprising a secondary amine comprising two hydroxyalkyl substituents, wherein the composition has a formula HO(CH2)xHN(CH2)yOH and x and y are integers between 1 to about 20;
(iii) providing a halide salt, wherein the halide salt is a bromide salt or an iodide salt, or an equivalent thereof; and
,(iv) mixing the conjugate of step (a) with the composition of step (b) and the halide salt of step (c) under non-pressurized conditions, thereby forming the conjugate;
(b) providing a boronic acid solution; and
(c) mixing the dihydroxyalkylaminoalkyl conjugate of step (a) with the boronic acid solution of step (b), thereby immobilizing the boronic acid.
-
-
55. A method for preparing a conjugated resin comprising the following steps:
-
(a) providing an alkyl halide or a substituted alkyl halide or a benzyl halide conjugated to an resin, wherein the alkyl halide has a formula —
(CH2)m—
X and m is an integer between 1 to about 20,and the halide is chloride, bromide, iodide, or an equivalent thereof;
(b) providing a composition comprising a secondary amine comprising two hydroxyalkyl substituents, wherein the composition has a formula HO(CH2)xHN(CH2)yOH and x and y are integers between 1 to about 20;
(c) providing a halide salt, wherein the halide salt is a bromide salt or an iodide salt or an equivalent thereof; and
,(d) mixing the conjugated resin of step (a) with the composition of step (b) and the halide salt of step (c) under non-pressurized conditions, thereby forming a dihydroxyalkylaminoalkyl-conjugated resin. - View Dependent Claims (58, 59, 60)
-
-
56. A method for preparing a conjugated polystyrene bead comprising the following steps:
-
(a) providing an alkyl halide or a substituted alkyl halide or a benzyl halide conjugated to a polystyrene bead, wherein the alkyl halide has a formula —
(CH2)m—
X and m is an integer between 1 to about 20, and the halide is chloride, bromide, iodide, or an equivalent thereof;
(b) providing a composition comprising a secondary amine comprising two hydroxyalkyl substituents, wherein the composition has a formula HO(CH2)xHN(CH2)yOH and x and y are integers between 1 to about 20;
(c) providing a halide salt, wherein the halide salt is a bromide salt or an iodide salt or an equivalent thereof; and
,(d) mixing the conjugated polystyrene bead of step (a) with the composition of step (b) and the halide salt of step (c) under non-pressurized conditions for about 24 to about 48 hours, thereby forming the dihydroxyalkylaminoalkyl-conjugated polystyrene beads.
-
-
57. A method for preparing a dihydroxyalkylaminoalkyl-conjugated scavenger resin comprising the following steps:
-
(a) providing an alkyl halide or a substituted alkyl halide or a benzyl halide conjugated to a resin, wherein the alkyl halide has a formula —
(CH2)m—
X and m is an integer between 1 to about 20, and the halide is chloride, bromide, iodide, or an equivalent thereof;
(b) providing a composition comprising a secondary amine comprising two hydroxyalkyl substituents, wherein the composition has a formula HO(CH2)xHN(CH2)yOH and x and y are integers between 1 to about 20;
(c) providing a halide salt, wherein the halide salt is a bromide salt or an iodide salt or an equivalent thereof; and
,(d) mixing the conjugated resin of step (a) with the composition of step (b) and the halide salt of step (c) under non-pressurized conditions, thereby forming a dihydroxyalkylaminoalkyl-conjugated scavenger resin.
-
- 61. A solid support derivatized with a dihydroxyalkylaminoalkyl group wherein the dihydroxyalkylaminoalkyl comprises a tertiary amine having two hydroxyalkyl substituents having a formula HO(CH2)xN (CH2)yOH, wherein x and y are integers between 1 to about 20.
- 68. The use of an iodide or bromide salt for the formation under non-pressurized conditions of a dihydroxyalkylaminoalkyl-conjugated solid support from an alkyl halide, a substituted alkyl halide or a benzyl halide conjugated to a solid support and a secondary amine comprising two hydroxyalkyl substituents, wherein the secondary amine has a formula HO(CH2)xHN(CH2)yOH and x and y are integers between 1 to about 20.
-
72. A method for preparing a conjugated support under non-pressurized conditions comprising the following steps:
-
(a) providing an alkyl halide, a substituted alkyl halide or a benzyl halide conjugated to a solid support, wherein the alkyl halide has a formula —
(CH2)m—
X and m is an integer between 1 to about 20, and the halide is chloride, bromide, iodide or an equivalent thereof;
(b) providing a composition comprising a secondary amine comprising two hydroxyalkyl substituents, wherein the composition has a formula HO(CH2)xHN(CH2)yOH and x and y are integers between 1 to about 20;
(c) providing a halide salt selected from the group consisting of an iodide salt, a bromide salt and equivalents thereof; and
,(d) mixing the conjugated solid support of step (a) with the composition of step (b) and the halide salt of step (c) under non-pressurized conditions, thereby forming a dihydroxyalkylaminoalkyl or a dihydroxyaminobenzyl-conjugated solid support.
-
Specification