US2007167606A1PendingUtilityA1
Polyethylene glycol aldehydes
Est. expiryJul 24, 2022(expired)· nominal 20-yr term from priority
Inventors:Chee-Youb Won
C08G 65/324C08G 65/331C08G 65/329C08G 65/2624C08G 65/2615
52
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Claims
Abstract
Polyethylene glycol aldehyde compounds are provided. Methods of making and using such compounds, as well as chemical intermediates are also provided.
Claims
exact text as granted — not AI-modified1 . A compound of formula (l):
R 1 —(CH 2 CH 2 O) n —CH 2 CH 2 —X—Y—NH—(CH 2 ) p —CHO (I)
wherein
R 1 is a capping group,
X is O or NH,
Y is selected from the group consisting of
Z is a side chain of an amino acid,
m is from 1 to 17,
n is from 10 to 10,000, and
p is from 1 to 3.
2 . A compound according to claim 1 , wherein R 1 is selected from the group consisting of halogen, epoxide, maleimide, orthopyridyl disulfide, tosylate, isocyanate, hydrazine hydrate, cyanuric halide, N-succinimidyloxy, sulfo-N-succinimidyloxy, 1-benzotriazolyloxy, 1-imidazolyloxy, p-nitrophenyloxy, and
3 . A compound according to claim 1 , wherein R 1 is selected from the group consisting of hydrogen, hydroxy, lower alkyl, lower alkoxy, lower cycloalkyl, lower alkenyl, aryl, and heteroaryl.
4 . A compound according to claim 1 , wherein R 1 is selected from the group consisting of methoxy, hydroxy, and benzyloxy.
5 . A compound according to claim 2 , wherein R 1 is
6 . A compound according to claim 1 having the formula (III):
7 . A compound according to claim 1 having the formula (IV):
8 . A compound according to claim 1 having the formula (V):
9 . A compound according to claim 1 having the formula (VI):
10 . A compound of formula (Il):
wherein
R 1 is a capping group,
m is from 1 to 17,
n is from 10 to 10,000, and
p is from 1 to 3.
11 . A compound according to claim 10 , wherein p is 3.
12 . A compound according to claim 11 , wherein R 1 is selected from the group consisting of methoxy, hydroxy, and benzyloxy.
13 . A compound according to claim 11 , wherein m is from 1 to 14.
14 . A compound according to claim 13 , wherein m is from 1 to 7.
15 . A compound according to claim 14 , wherein m is from 1 to 4.
16 . A compound according to claim 11 , wherein n is from 20 to 5,000.
17 . A compound according to claim 16 , wherein n is from 50 to 2,500.
18 . A compound according to claim 17 , wherein n is from 75 to 1,000.
19 . A compound according to claim 10 , wherein p is 3, R 1 is methoxy, m is 1, and n is from 100 to 750.
20 . A compound according to claim 10 , wherein p is 2.
21 . A compound according to claim 20 , wherein R 1 is selected from the group consisting of methoxy, hydroxy, or benzyloxy.
22 . A compound according to claim 20 , wherein m is from 1 to 14.
23 . A compound according to claim 22 , wherein m is from 1 to 7.
24 . A compound according to claim 23 , wherein m is from 1 to 4.
25 . A compound according to claim 20 , wherein n is from 20 to 5,000.
26 . A compound according to claim 25 , wherein n is from 50 to 2,500.
27 . A compound according to claim 26 , wherein n is from 75 to 1,000.
28 . A compound according to claim 10 , wherein p is 2, R 1 is methoxy, m is 1, and n is from 100 to 750.
29 . A compound according to claim 10 , wherein p is 1.
30 . A compound according to claim 29 , wherein R 1 is selected from the group consisting of methoxy, hydroxy, or benzyloxy.
31 . A compound according to claim 29 , wherein m is from 1 to 14.
32 . A compound according to claim 31 , wherein m is from 1 to 7.
33 . A compound according to claim 32 , wherein m is from 1 to 4.
34 . A compound according to claim 29 , wherein n is from 20 to 5,000.
35 . A compound according to claim 34 , wherein n is from 50 to 2,500.
36 . A compound according to claim 35 , wherein n is from 75 to 1,000.
37 . A compound according to claim 10 , wherein p is 1, R 1 is methoxy, m is 1, and n is from 100 to 750.
38 . A compound of formula (VIII):
wherein
m is from 1 to 17,
n is from 10 to 10,000, and
p is from 1 to 3.
39 . A compound according to claim 38 , wherein m is from 1 to 14.
40 . A compound according to claim 39 , wherein m is from 1 to 7.
41 . A compound according to claim 40 , wherein m is from 1 to 4.
42 . A compound according to claim 38 , wherein n is from 20 to 5,000.
43 . A compound according to claim 42 , wherein n is from 50 to 2,500.
44 . A compound according to claim 43 , wherein n is from 75 to 1,000.
45 . A compound according to claim 38 , wherein p is 3, m is 1 and n is from 100 to 750.
46 . A compound of formula (IX):
R 1 —(CH 2 —CH 2 —O) n —CH 2 13 CH 2 —X—Y—NH—(CH 2 ) p —CH(OCH 2 —CH 3 ) 2 (IX)
wherein
R 1 is a capping group,
X is O or NH,
Y is selected from the group consisting of
Z is a side chain of an amino acid,
m is from 1 to 17,
n is from 10 to 10,000, and
p is from 1 to 3.
47 . A compound according to claim 46 , wherein R 1 is selected from the group consisting of halogen, epoxide, maleimide, orthopyridyl disulfide, tosylate, isocyanate, hydrazine hydrate, cyanuric halide, N-succinimidyloxy, sulfo-N-succinimidyloxy, 1-benzotriazolyloxy, 1-imidazolyloxy, p-nitrophenyloxy, and
48 . A compound according to claim 46 , wherein R 1 is selected from the group consisting of hydrogen, hydroxy, lower alkyl, lower alkoxy, lower cycloalkyl, lower alkenyl, aryl, and heteroaryl.
49 . A compound according to claim 46 , wherein R 1 is selected from the group consisting of methoxy, hydroxy, and benzyloxy.
50 . A compound according to claim 46 , wherein R 1 is
51 . A compound according to claim 46 , wherein m is from 1 to 14.
52 . A compound according to claim 51 , wherein m is from 1 to 7.
53 . A compound according to claim 52 , wherein m is from 1 to 4.
54 . A compound according to claim 46 , wherein n is from 20 to 5,000.
55 . A compound according to claim 54 , wherein n is from 50 to 2,500.
56 . A compound according to claim 55 , wherein n is from 75 to 1,000.
57 . A compound according to claim 46 , wherein R 1 is methoxy, p is 3, m is 1, and n is from 100 to 750.
58 . A compound of formula (X):
wherein
R 1 is a capping group,
m is from 1 to 17,
n is from 10 to 10,000, and
p is from 1 to 3.
59 . A compound according to claim 58 , wherein R 1 is selected from the group consisting of halogen, epoxide, maleimide, orthopyridyl disulfide, tosylate, isocyanate, hydrazine hydrate, cyanuric halide, N-succinimidyloxy, sulfo-N-succinimidyloxy, 1-benzotriazolyloxy, 1-imidazolyloxy, p-nitrophenyloxy, and
60 . A compound according to claim 58 , wherein R 1 is selected from the group consisting of hydrogen, hydroxy, lower alkyl, lower alkoxy, lower cycloalkyl, lower alkenyl, aryl, and heteroaryl.
61 . A compound according to claim 58 , wherein R 1 is selected from the group consisting of methoxy, hydroxy, and benzyloxy.
62 . A compound according to claim 58 , wherein R 1 is
63 . A compound according to claim 62 , wherein m is from 1 to 14.
64 . A compound according to claim 63 , wherein m is from 1 to 7.
65 . A compound according to claim 64 , wherein m is from 1 to 4.
66 . A compound according to claim 58 , wherein n is from 20 to 5,000.
67 . A compound according to claim 66 , wherein n is from 50 to 2,500.
68 . A compound according to claim 67 , wherein n is from 75 to 1,000.
69 . A compound according to claim 58 , wherein R 1 is methoxy, p is 3, m is 1, and n is from 100 to 750.
70 . A compound of formula (XI):
wherein
m is from 1 to 17,
n is from 10 to 10,000, and
p is from 1 to 3.
71 . A compound according to claim 70 , wherein m is from 1 to 14.
72 . A compound according to claim 71 , wherein m is from 1 to 7.
73 . A compound according to claim 72 , wherein m is from 1 to 4.
74 . A compound according to claim 70 , wherein n is from 20 to 5,000.
75 . A compound according to claim 74 , wherein n is from 50 to 2,500.
76 . A compound according to claim 75 , wherein n is from 75 to 1,000.
77 . A compound according to claim 70 , wherein p is 3, m is 1 and n is from 100 to 750.
78 . A method of making a polyethylene glycol aldehyde comprising hydrolyzing a compound of formula (IX):
R 1 —(CH 2 —CH 2 —O) n —CH 2 CH 2 —X—Y—NH—(CH 2 ) p —CH—(OCH 2 —CH 3 ) 2 (IX)
to produce a polyethylene glycol aldehyde of formula (I):
R 1 —(CH 2 CH 2 O) n —CH 2 CH 2 —X—Y—NH—(CH 2 ) p —CHO (I)
wherein
R 1 is a capping group,
X is O or NH,
Y is selected from the group consisting of
Z is a side chain of an amino acid,
m is from 1 to 17,
n is from 10 to 10,000, and
p is from 1 to 3.
79 . A method of making a polyethylene glycol aldehyde comprising hydrolyzing a compound of formula (X):
to produce a polyethylene glycol aldehyde of formula (II):
wherein
R 1 is a capping group,
m is from 1 to 17,
n is from 10 to 10,000, and
p is from 1 to 3.
80 . A method according to claim 79 wherein the compound of formula (X) is produced by reacting a compound of formula (XII):
R 1 —(CH 2 —CH 2 —O) n —CH 2 CH 2 —O—(CH 2 ) m —COOH (XII)
with a compound of formula (XIII):
H 2 N—(CH 2 ) p —CH—(OCH 2 —CH 3 ) 2 (XIII).
81 . A method according to claim 80 wherein the compound of formula (XII) is produced by hydrolyzing a compound of formula (XIV):
R 1 —O—(CH 2 —CH 2 —O) n —CH 2 CH 2 —O—(CH 2 ) m —COOR 3 (XIV)
wherein R 3 is a branched or unbranched C 1 -C 4 alkyl.
82 . A method according to claim 81 wherein the compound of formula (XIV) is produced by reacting a compound of formula (XV):
R 1 —(CH 2 —CH 2 —O) n —CH 2 CH 2 —OH (XV)
with a compound of formula (XVI):
R 2 —(CH 2 ) m —COOR 3 (XVI)
wherein R 2 is halogen.
83 . A method of making a polyethylene glycol aldehyde comprising hydrolyzing a compound of formula (XVII):
to produce a polyethylene glycol of formula (Vil):
wherein
m is from 1 to 17,
n is from 10 to 10,000, and
p is from 1 to 3.
84 . A method according to claim 83 wherein the compound of formula (VIII) is produced by reacting a compound of formula (XVIII):
HOOC—(CH 2 ) m —O—CH 2 CH 2 —(CH 2 —CH 2 —O) n —CH 2 CH 2 —O—(CH 2 ) m —COOH (XVIII)
with a compound of formula (XIX):
H 2 N—(CH 2 ) p —CH—(OCH 2 —CH 3 ) 2 (XIX).
85 . A method according to claim 84 wherein the compound of formula (XVIII) is produced by hydrolyzing a compound of formula (XX):
R 3 OOC—(CH 2 ) m —CH 2 CH 2 —O—(CH 2 —CH 2 —O) n —CH 2 CH 2 —O—(CH 2 ) m —COOR 3 (XXI)
wherein R 3 is a branched or unbranched C 1 -C 4 alkyl.
86 . A method according to claim 85 wherein the compound of formula (XX) is produced by reacting a compound of formula (XXI):
HO—CH 2 CH 2 —(CH 2 —CH 2 —O) n —CH 2 CH 2 —OH (XXI)
with a compound of formula (XVI):
R 2 —(CH 2 ) m —COOR 3 (XVI)
wherein R 2 is halogen.Cited by (0)
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