US 2013/0157926 A1 · BORONATED POLYMERS

Abstract

The present invention relates to a boronated polymer according to Formula (1): a process for making the boronated polymer according to Formula (1), drug 10 delivery systems, aggregates, nanoparticles and hydrogels comprising the boronated polymer according to Formula (1).

Claims26

Dependent claims

1-19. (canceled)

A boronated polymer according to Formula (1):

wherein:
A is independently selected from a direct carbon-carbon single bond, O, N and S;
R1 is independently selected from H and CH3;
R2 is independently selected from the group consisting of:
(a) C1-C20 alkylene, wherein the alkylene group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein the alkylene group is interrupted by one or more —S—S— groups;
(b) C3-C20 cycloalkylene, wherein the cycloalkylene group is optionally substituted and/or is optionally (partly) unsaturated and/or optionally comprises one or more heteroatoms in the ring, wherein the heteroatoms are independently selected from O, N and S, and/or wherein the cycloalkylene group is interrupted by one or more —S—S-groups outside the ring;
(c) C6-C20 arylene, wherein the arylene group is optionally substituted;
(d) C6-C20 heteroarylene, wherein the heteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(e) C7-C20 alkylarylene wherein the alkylarylene group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein an alkyl part of the alkylarylene group is interrupted by one or more —S—S— groups;
(f) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein an alkyl part of the alkylheteroarylene group is interrupted by one or more —S—S— groups;
and
(g) a group wherein two (hetero)arylene groups and/or alkyl(hetero)arylene groups are connected to each other by a —S—S— group;
D is selected from the group consisting of —(CR42)r- and the groups (a), (b), (c), (d), (e), (f) and (g) defined for R2;
R4 is independently selected from the group consisting of:
(a) H;
(b) C1-C20 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(c) C3-C20 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or optionally comprises one or more heteroatoms in the ring, wherein the heteroatoms are independently selected from O, N and S;
(d) C6-C20 aryl, wherein the aryl group is optionally substituted;
(e) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroaryl group is optionally substituted;
(f) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(g) C7-C20 alkylheteroaryl, wherein the alkylheteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroaryl group is optionally substituted, and/or wherein an alkyl part of the alkylheteroaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R5 is independently selected from the group consisting of H and C1-C20 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
p=1 to 100;
q=0 to 100;
r=2-6;
s=0-5;
R3 has the Formula (2):
wherein:
a is 1 or 2;
R6 is independently selected from
(a) H;
(b) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(c) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(d) C6-C20 aryl, wherein the aryl group is optionally substituted;
(e) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(f) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryle group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(g) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R7 is independently selected from
(a) halogen;
(b) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(c) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(d) C6-C20 aryl, wherein the aryl group is optionally substituted;
(e) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(f) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(g) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
E is independently selected from the group consisting of:
—(CR82)u—N(R9)—C(O)—,
—C(O)—N(R9)—(CR82)u—,
—(CR82)u—N═CR9—,
—CR9═N—(CR82)u—, and
—(CR82)u—N(R9)—(CR82)v—;
t=0-4;
u=1-10;
v=1-4;
R8 is independently selected from the group consisting of H and C1-C20 alkyl;
R9 is independently selected from the group consisting of H and C1-C20 alkyl;
and
when s=0, then R3* is independently selected from the group consisting of
(a) H,
(b) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(c) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(d) C6-C20 aryl, wherein the aryl group is optionally substituted;
(e) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(f) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(g) C7-C20 alkylheteroaryl, wherein the alkylheteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroaryl group is optionally substituted, and/or wherein an alkyl part of the alkylheteroaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
when s=1-5, then R3* is independently selected from the group consisting of
(a) H;
(b) C1-C6 alkyl, wherein the alkyl group is optionally substituted;
(c) C3-C6 cycloalkyl, wherein the cycloalkyl group is optionally substituted;
C6-C12 aryl, wherein the aryl group is optionally substituted;
(d) C6-C12 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(e) C7-C12 alkylaryl wherein the alkylaryl group is optionally substituted;
and
(f) C7-C12 alkylheteroaryl, wherein the alkylheteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroaryl group is optionally substituted.

75 more elements

A process for preparing a boronated polymer according to Formula (1):

wherein:
A is independently selected from a direct carbon-carbon single bond, O, N and S;
R1 is independently selected from H and CH3;
R2 is independently selected from the group consisting of:
(a) C1-C20 alkylene, wherein the alkylene group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein the alkylene group is interrupted by one or more —S—S— groups;
(b) C3-C20 cycloalkylene, wherein the cycloalkylene group is optionally substituted and/or is optionally (partly) unsaturated and/or optionally comprises one or more heteroatoms in the ring, wherein the heteroatoms are independently selected from O, N and S, and/or wherein the cycloalkylene group is interrupted by one or more —S—S-groups outside the ring;
(c) C6-C20 arylene, wherein the arylene group is optionally substituted;
(d) C6-C20 heteroarylene, wherein the heteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(e) C7-C20 alkylarylene wherein the alkylarylene group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein an alkyl part of the alkylarylene group is interrupted by one or more —S—S— groups;
(f) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein an alkyl part of the alkylheteroarylene group is interrupted by one or more —S—S— groups;
and
(g) a group wherein two (hetero)arylene groups and/or alkyl(hetero)arylene groups are connected to each other by a —S—S— group;
D is selected from the group consisting of —(CR42)r- and the groups (a), (b), (c), (d), (e), (f) and (g) defined for R2;
R4 is independently selected from the group consisting of:
(h) H;
(i) C1-C20 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(j) C3-C20 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or optionally comprises one or more heteroatoms in the ring, wherein the heteroatoms are independently selected from O, N and S;
(k) C6-C20 aryl, wherein the aryl group is optionally substituted;
(l) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroaryl group is optionally substituted;
(m) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(n) C7-C20 alkylheteroaryl, wherein the alkylheteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroaryl group is optionally substituted, and/or wherein an alkyl part of the alkylheteroaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R3 is independently selected from the group consisting of H and C1-C20 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
p=1 to 100;
q=0 to 100;
r=2-6;
s=0-5;
R3 has the Formula (2):
wherein:
a is 1 or 2;
R6 is independently selected from
(h) H;
(i) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(j) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(k) C6-C20 aryl, wherein the aryl group is optionally substituted;
(l) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(m) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryle group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(n) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R7 is independently selected from
(h) halogen;
(i) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(j) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(k) C6-C20 aryl, wherein the aryl group is optionally substituted;
(l) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(m) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(n) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
E is independently selected from the group consisting of:
—(CR82)u—N(R9)—C(O)—,
—C(O)—N(R9)—(CR82)u—,
—(CR82)u—N═CR9—,
—CR9═N—(CR8u)u—, and
—(CR82)u—N(R9)—(CR82)v—;
t=0-4;
u=1-10;
v=1-4;
R8 is independently selected from the group consisting of H and C1-C20 alkyl;
R9 is independently selected from the group consisting of H and C1-C20 alkyl;
and
when s=0, then R3* is independently selected from the group consisting of
(h) H,
(i) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(j) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(k) C6-C20 aryl, wherein the aryl group is optionally substituted;
(l) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(m) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(n) C7-C20 alkylheteroaryl, wherein the alkylheteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroaryl group is optionally substituted, and/or wherein an alkyl part of the alkylheteroaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
when s=1-5, then R3* is independently selected from the group consisting of
(g) H;
(h) C1-C6 alkyl, wherein the alkyl group is optionally substituted;
(i) C3-C6 cycloalkyl, wherein the cycloalkyl group is optionally substituted;
C6-C12 aryl, wherein the aryl group is optionally substituted;
(j) C6-C12 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(k) C7-C12 alkylaryl wherein the alkylaryl group is optionally substituted;
and
(l) C7-C12 alkylheteroaryl, wherein the alkylheteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroaryl group is optionally substituted;
said process comprising polymerizing a monomer according to Formula (6):
with a monomer according to Formula (7):
H2N—R3 (7).

78 more elements

A hydrogel comprising a poly(boronic acid) cross-linker according to Formula (14):

wherein:
a=1 or 2;
R6 is independently selected from
(a) H;
(b) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(c) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
C6-C20 aryl, wherein the aryl group is optionally substituted;
(d) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(e) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(f) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R7 is independently selected from
(g) halogen;
(h) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(i) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(j) C6-C20 aryl, wherein the aryl group is optionally substituted;
(k) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(l) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(m) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
E is independently selected from the group consisting of:
—(CR82)u—N(R9)—C(O)—,
—C(O)—N(R9)—(CR82)u—,
—(CR82)u—N═CR9—,
—C(R9)═N—(CR82)u—, and
—(CR82)u—N(R9)—(CR82)v—;
R8 is independently selected from the group consisting of H and C1-C20 alkyl;
R9 is independently selected from the group consisting of H and C1-C20 alkyl;
t=0-4;
u=1-10;
v=1-4;
R12 is independently selected from
(a) C1-C12 alkylene, wherein the alkylene group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(b) C3-C12 cycloalkylene, wherein the cycloalkylene group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(c) C6-C20 arylene, wherein the arylene group is optionally substituted;
(d) C6-C20 heteroarylene, wherein the heteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(e) C7-C20 alkylarylene wherein the alkylarylene group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(f) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(g) Polyalkylene having a weight average molecular weight Mw of about 150 to about 10,000, wherein the polyalkylene group may be linear or branched and is interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S.

37 more elements

A hydrogel comprising a poly(boronic acid) cross-linker according to Formula (15):

wherein:
x=3-8;
a=1 or 2;
R6 is independently selected from
(g) H;
(h) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(i) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
C6-C20 aryl, wherein the aryl group is optionally substituted;
(j) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(k) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(l) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R7 is independently selected from
(n) halogen;
(o) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(p) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(q) C6-C20 aryl, wherein the aryl group is optionally substituted;
(r) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(s) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(t) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
E is independently selected from the group consisting of:
—(CR82)u—N(R9)—C(O)—,
—C(O)—N(R9)—(CR82)u—,
—(CR82)u—N═CR9—,
—C(R9)═N—(CR82)u—, and
—(CR82)u—N(R9)—(CR82)v—;
R8 is independently selected from the group consisting of H and C1-C20 alkyl;
R9 is independently selected from the group consisting of H and C1-C20 alkyl;
t=0-4;
u=1-10;
v=1-4;
R12 is a polyalkylene having a weight average molecular weight Mw of about 1,000 to about 50,000, wherein the polyoxyalkylene has a (hyper)branched, multi-arm and/or dendrimeric structure and is interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S.

30 more elements

Dependencies are inferred from the claim text.

Facts

Application

13/704,960Filed 20 Jun 2011

Priority

EP 10166466.218 Jun 2010

Published

20 Jun 2013

Term ends

Not estimatedThe source records don’t support an estimate.

Classification13 codes

A61K 47/34
Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates: macromolecular compounds obtained otherwise than by reactions only…
A61K 9/06
Medicinal preparations characterised by special physical form: ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
A61K 9/5146
Organic macromolecular compounds; Dendrimers: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g.…
C08G 65/337
With organic compounds: containing other elements

Abstract

Claims26

Dependent claims

1-19. (canceled)

A boronated polymer according to Formula (1):

wherein:
A is independently selected from a direct carbon-carbon single bond, O, N and S;
R1 is independently selected from H and CH3;
R2 is independently selected from the group consisting of:
(a) C1-C20 alkylene, wherein the alkylene group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein the alkylene group is interrupted by one or more —S—S— groups;
(b) C3-C20 cycloalkylene, wherein the cycloalkylene group is optionally substituted and/or is optionally (partly) unsaturated and/or optionally comprises one or more heteroatoms in the ring, wherein the heteroatoms are independently selected from O, N and S, and/or wherein the cycloalkylene group is interrupted by one or more —S—S-groups outside the ring;
(c) C6-C20 arylene, wherein the arylene group is optionally substituted;
(d) C6-C20 heteroarylene, wherein the heteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(e) C7-C20 alkylarylene wherein the alkylarylene group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein an alkyl part of the alkylarylene group is interrupted by one or more —S—S— groups;
(f) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein an alkyl part of the alkylheteroarylene group is interrupted by one or more —S—S— groups;
and
(g) a group wherein two (hetero)arylene groups and/or alkyl(hetero)arylene groups are connected to each other by a —S—S— group;
D is selected from the group consisting of —(CR42)r- and the groups (a), (b), (c), (d), (e), (f) and (g) defined for R2;
R4 is independently selected from the group consisting of:
(a) H;
(b) C1-C20 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(c) C3-C20 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or optionally comprises one or more heteroatoms in the ring, wherein the heteroatoms are independently selected from O, N and S;
(d) C6-C20 aryl, wherein the aryl group is optionally substituted;
(e) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroaryl group is optionally substituted;
(f) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(g) C7-C20 alkylheteroaryl, wherein the alkylheteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroaryl group is optionally substituted, and/or wherein an alkyl part of the alkylheteroaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R5 is independently selected from the group consisting of H and C1-C20 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
p=1 to 100;
q=0 to 100;
r=2-6;
s=0-5;
R3 has the Formula (2):
wherein:
a is 1 or 2;
R6 is independently selected from
(a) H;
(b) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(c) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(d) C6-C20 aryl, wherein the aryl group is optionally substituted;
(e) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(f) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryle group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(g) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R7 is independently selected from
(a) halogen;
(b) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(c) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(d) C6-C20 aryl, wherein the aryl group is optionally substituted;
(e) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(f) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(g) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
E is independently selected from the group consisting of:
—(CR82)u—N(R9)—C(O)—,
—C(O)—N(R9)—(CR82)u—,
—(CR82)u—N═CR9—,
—CR9═N—(CR82)u—, and
—(CR82)u—N(R9)—(CR82)v—;
t=0-4;
u=1-10;
v=1-4;
R8 is independently selected from the group consisting of H and C1-C20 alkyl;
R9 is independently selected from the group consisting of H and C1-C20 alkyl;
and
when s=0, then R3* is independently selected from the group consisting of
(a) H,
(b) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(c) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(d) C6-C20 aryl, wherein the aryl group is optionally substituted;
(e) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(f) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(g) C7-C20 alkylheteroaryl, wherein the alkylheteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroaryl group is optionally substituted, and/or wherein an alkyl part of the alkylheteroaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
when s=1-5, then R3* is independently selected from the group consisting of
(a) H;
(b) C1-C6 alkyl, wherein the alkyl group is optionally substituted;
(c) C3-C6 cycloalkyl, wherein the cycloalkyl group is optionally substituted;
C6-C12 aryl, wherein the aryl group is optionally substituted;
(d) C6-C12 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(e) C7-C12 alkylaryl wherein the alkylaryl group is optionally substituted;
and
(f) C7-C12 alkylheteroaryl, wherein the alkylheteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroaryl group is optionally substituted.

75 more elements

A process for preparing a boronated polymer according to Formula (1):

wherein:
A is independently selected from a direct carbon-carbon single bond, O, N and S;
R1 is independently selected from H and CH3;
R2 is independently selected from the group consisting of:
(a) C1-C20 alkylene, wherein the alkylene group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein the alkylene group is interrupted by one or more —S—S— groups;
(b) C3-C20 cycloalkylene, wherein the cycloalkylene group is optionally substituted and/or is optionally (partly) unsaturated and/or optionally comprises one or more heteroatoms in the ring, wherein the heteroatoms are independently selected from O, N and S, and/or wherein the cycloalkylene group is interrupted by one or more —S—S-groups outside the ring;
(c) C6-C20 arylene, wherein the arylene group is optionally substituted;
(d) C6-C20 heteroarylene, wherein the heteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(e) C7-C20 alkylarylene wherein the alkylarylene group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein an alkyl part of the alkylarylene group is interrupted by one or more —S—S— groups;
(f) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein an alkyl part of the alkylheteroarylene group is interrupted by one or more —S—S— groups;
and
(g) a group wherein two (hetero)arylene groups and/or alkyl(hetero)arylene groups are connected to each other by a —S—S— group;
D is selected from the group consisting of —(CR42)r- and the groups (a), (b), (c), (d), (e), (f) and (g) defined for R2;
R4 is independently selected from the group consisting of:
(h) H;
(i) C1-C20 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(j) C3-C20 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or optionally comprises one or more heteroatoms in the ring, wherein the heteroatoms are independently selected from O, N and S;
(k) C6-C20 aryl, wherein the aryl group is optionally substituted;
(l) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroaryl group is optionally substituted;
(m) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(n) C7-C20 alkylheteroaryl, wherein the alkylheteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroaryl group is optionally substituted, and/or wherein an alkyl part of the alkylheteroaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R3 is independently selected from the group consisting of H and C1-C20 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
p=1 to 100;
q=0 to 100;
r=2-6;
s=0-5;
R3 has the Formula (2):
wherein:
a is 1 or 2;
R6 is independently selected from
(h) H;
(i) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(j) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(k) C6-C20 aryl, wherein the aryl group is optionally substituted;
(l) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(m) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryle group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(n) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R7 is independently selected from
(h) halogen;
(i) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(j) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(k) C6-C20 aryl, wherein the aryl group is optionally substituted;
(l) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(m) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(n) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
E is independently selected from the group consisting of:
—(CR82)u—N(R9)—C(O)—,
—C(O)—N(R9)—(CR82)u—,
—(CR82)u—N═CR9—,
—CR9═N—(CR8u)u—, and
—(CR82)u—N(R9)—(CR82)v—;
t=0-4;
u=1-10;
v=1-4;
R8 is independently selected from the group consisting of H and C1-C20 alkyl;
R9 is independently selected from the group consisting of H and C1-C20 alkyl;
and
when s=0, then R3* is independently selected from the group consisting of
(h) H,
(i) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(j) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(k) C6-C20 aryl, wherein the aryl group is optionally substituted;
(l) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(m) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(n) C7-C20 alkylheteroaryl, wherein the alkylheteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroaryl group is optionally substituted, and/or wherein an alkyl part of the alkylheteroaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
when s=1-5, then R3* is independently selected from the group consisting of
(g) H;
(h) C1-C6 alkyl, wherein the alkyl group is optionally substituted;
(i) C3-C6 cycloalkyl, wherein the cycloalkyl group is optionally substituted;
C6-C12 aryl, wherein the aryl group is optionally substituted;
(j) C6-C12 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(k) C7-C12 alkylaryl wherein the alkylaryl group is optionally substituted;
and
(l) C7-C12 alkylheteroaryl, wherein the alkylheteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroaryl group is optionally substituted;
said process comprising polymerizing a monomer according to Formula (6):
with a monomer according to Formula (7):
H2N—R3 (7).

78 more elements

A hydrogel comprising a poly(boronic acid) cross-linker according to Formula (14):

wherein:
a=1 or 2;
R6 is independently selected from
(a) H;
(b) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(c) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
C6-C20 aryl, wherein the aryl group is optionally substituted;
(d) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(e) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(f) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R7 is independently selected from
(g) halogen;
(h) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(i) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(j) C6-C20 aryl, wherein the aryl group is optionally substituted;
(k) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(l) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(m) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
E is independently selected from the group consisting of:
—(CR82)u—N(R9)—C(O)—,
—C(O)—N(R9)—(CR82)u—,
—(CR82)u—N═CR9—,
—C(R9)═N—(CR82)u—, and
—(CR82)u—N(R9)—(CR82)v—;
R8 is independently selected from the group consisting of H and C1-C20 alkyl;
R9 is independently selected from the group consisting of H and C1-C20 alkyl;
t=0-4;
u=1-10;
v=1-4;
R12 is independently selected from
(a) C1-C12 alkylene, wherein the alkylene group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(b) C3-C12 cycloalkylene, wherein the cycloalkylene group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(c) C6-C20 arylene, wherein the arylene group is optionally substituted;
(d) C6-C20 heteroarylene, wherein the heteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(e) C7-C20 alkylarylene wherein the alkylarylene group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(f) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(g) Polyalkylene having a weight average molecular weight Mw of about 150 to about 10,000, wherein the polyalkylene group may be linear or branched and is interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S.

37 more elements

A hydrogel comprising a poly(boronic acid) cross-linker according to Formula (15):

wherein:
x=3-8;
a=1 or 2;
R6 is independently selected from
(g) H;
(h) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(i) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
C6-C20 aryl, wherein the aryl group is optionally substituted;
(j) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(k) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(l) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R7 is independently selected from
(n) halogen;
(o) C1-C12 alkyl, wherein the alkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(p) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(q) C6-C20 aryl, wherein the aryl group is optionally substituted;
(r) C6-C20 heteroaryl, wherein the heteroaryl group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(s) C7-C20 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylaryl group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(t) C7-C20 alkylheteroarylene, wherein the alkylheteroarylene group comprises 1-3 heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is optionally (partly) unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
E is independently selected from the group consisting of:
—(CR82)u—N(R9)—C(O)—,
—C(O)—N(R9)—(CR82)u—,
—(CR82)u—N═CR9—,
—C(R9)═N—(CR82)u—, and
—(CR82)u—N(R9)—(CR82)v—;
R8 is independently selected from the group consisting of H and C1-C20 alkyl;
R9 is independently selected from the group consisting of H and C1-C20 alkyl;
t=0-4;
u=1-10;
v=1-4;
R12 is a polyalkylene having a weight average molecular weight Mw of about 1,000 to about 50,000, wherein the polyoxyalkylene has a (hyper)branched, multi-arm and/or dendrimeric structure and is interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S.

30 more elements

Dependencies are inferred from the claim text.

Boronated polymers

Life of this patent

Abstract

Claims26

Boronated polymers

Life of this patent

Abstract

Claims26