US 8,410,309 B2Granted

Phenoxy carboxylic acid compounds and compositions for delivering active agents

AssigneeEmisphere Technologies, Inc.

InventorsAndrea Leone-Bay, Kelly Kraft, Destardi Moye-Sherman, David Gschneidner, Maria Aurora P. Boyd, Puchun Liu, Pingwah Tang, Jun Liao, John Smart, John J. Freeman, Jr.

Life of this patent

Estimating the term…

Abstract

Phenoxy carboxylic acid compounds and compositions for the delivery of active agents are provided. Methods of administration and preparation are provided as well.

Claims23

Dependent claims

A compound having the formula

and salts thereof, wherein
R1 is H, —OH, halogen, C2-C4 alkenyl, C1-C4 alkoxy, —C(O)R8, —NO2, —NR9R10, or —N+R9R10R11 (R12)−;
R2 is H, —OH, halogen, C2-C4 alkenyl, C2-C4 alkoxy, —C(O)R8, —NO2, —NR9R10, or —N+R9R10R11 (R12);
R3 is H, halogen, C2-C4 alkenyl, C1-C4 alkoxy, —C(O)R8, —NO2, —NR9R10, or —N+R9R10R11 (R12);
R4 is H, —OH, halogen, C2-C4 alkenyl, C2-C4 alkoxy, —C(O)R8, —NO2, —NR9R10, or —N+R9R10R11 (R12);
R5 is —NO2, halogen, —NR14R15,—N+R14R15R16 (R13)−, amide, C1-C12 alkoxy, C2-C12 alkenyl, carbamate, carbonate, ureido, or —C(O)R18;
R5 is optionally substituted with halogen, —OH, —SH, or —COOH;
R5 is optionally interrupted by O, N, S, or —C(O)—;
R6 is a C4-C12 linear or branched alkyl, C2-C12 linear or branched alkenyl, or aryl;
R6 is optionally substituted with a C1-C4 alkyl, C2-C4 alkenyl, C1-C4 alkoxy, —OH, —SH, halogen, —NH2, or —CO2R8;
R6 is optionally interrupted by O or N;
R7 is a bond or aryl;
R7 is optionally substituted with —OH, halogen, —C(O)CH3, —NR10R11, or —N+R10R11R12 (R13)−;
R8 is C1-C4 alkyl, or C2-C4 alkenyl;
R9, R10, R11, and R12 are independently H or C1-C10 alkyl;
R13 is a halide, hydroxide, sulfate, tetrafluoroborate, or phosphate;
and
R14, R15 and R16 are independently C1-C10 alkyl, C2-C12 alkenyl, —C(O)R7;
R17 is —OH, C1-C10 alkyl, or C2-C12 alkenyl;
and
R18 is C1-C6 alkyl, —OH, —NR14R15, or N+R14R15R16(R13).

18 more elements

A compound selected from the group consisting of

Cpd
#
R1
R2
R3
R4
1
H
H
H
H
2
H
H
H
H
9
H
H
H
H
10
H
H
H
H
11
H
H
H
H
12
H
H
H
H
18
H
H
H
H
19
H
H
H
H
20
H
H
H
H
22
H
H
Cl
H
23
H
H
Cl
H
24
H
H
H
H
25
H
H
H
H
26
H
H
H
H
27
H
H
H
H
28
H
H
H
H
29
H
H
H
H
30
H
H
H
H
31
H
H
H
H
32
H
H
H
H
33
H
H
H
H
34
H
H
H
H
35
H
H
H
H
36
H
H
H
H
37
H
H
H
H
38
H
H
H
OH
39
H
H
H
OCH3
51
H
H
H
H
52
H
H
H
H
54
H
H
H
H
55
H
H
OCH3
H
56
H
OCH3
H
H
57
H
H
OH
H
58
H
H
CH3
H
59
H
H
H
H
61
H
H
H
H
62
H
H
C(O)CH3
H
63
H
H
C(O)CH2CH3
H
64
H
C(O)CH3
H
H
68
H
Cl
H
H
71
H
H
F
H
72
H
H
H
H
73
H
H
H
H
74
H
NO2
H
H
75
H
H
H
H
76
H
H
H
H
77
H
H
H
H
79
H
H
H
H
80
H
H
OCH3
H
81
H
H
OH
H
82
H
H
OH
H
83
H
H
OH
H
84
H
H
OH
H
85
H
H
OCH3
H
86
H
H
OCH3
H
87
H
H
H
H
88
H
H
H
H
89
H
H
Cl
H
90
H
H
H
H
91
H
OCH3
H
H
92
H
H
H
H
93
H
CH3
H
H
94
H
CH3
H
H
Cpd
#
R5
R6
R7
1
C(O)CH3
CH2
para-
Ph
2
OH
CH2
para-
Ph
9
C(O)CH3
(CH2)3
bond
10
C(O)CH3
(CH2)4
bond
11
C(O)CH3
(CH2)5
bond
12
C(O)CH3
(CH2)7
bond
18
CH═CHCH3
(CH2)7
bond
19
NH2
(CH2)7
bond
20
NO2
(CH2)7
bond
22
NH2
(CH2)7
bond
23
NH2
(CH2)4
bond
24
NHC(O)CH3
(CH2)7
bond
25
CH═CHCO2H
(CH2)7
bond
26
C(O)CH2CH3
(CH2)3
bond
27
C(O)CH2CH3
(CH2)5
bond
28
C(O)CH2CH3
(CH2)7
bond
29
C(O)CH2CH3
(CH2)9
bond
30
C(O)NH2
(CH2)7
bond
31
C(O)NHCH3
(CH2)7
bond
32
COOH
(CH2)7
bond
33
C(O)NHCH2CH3
(CH2)7
bond
34
C(O)NHCH(CH3)2
(CH2)7
bond
35
OCH3
(CH2)7
bond
36
CH(OH)CH3
(CH2)7
bond
37
C(CH3)2OH
CH2
para-
Ph
38
C(O)CH3
(CH2)7
bond
39
C(O)CH3
(CH2)7
bond
51
C(O)NHCH3
(CH2)9
bond
52
C(O)NH2
CH2
para-
Ph
54
C(O)CH3
(CH2)9
bond
55
C(O)CH3
(CH2)7
bond
56
C(O)CH3
(CH2)7
bond
57
C(O)CH3
(CH2)7
bond
58
C(O)CH3
(CH2)5
bond
59
C(O)H
CH2
para-
Ph
61
C(O)H
(CH2)7
bond
62
H
(CH2)7
bond
63
H
(CH2)7
bond
64
H
(CH2)7
bond
68
H
(CH2)7
bond
71
F
(CH2)7
bond
72
OH
(CH2)10
bond
73
Cl
(CH2)7
bond
74
OH
(CH2)7
bond
75
F
(CH2)4
bond
76
CF3
(CH2)4
bond
77
F
(CH2)7
bond
79
OH
CH2CH(OH)
para-
Ph
80
H
(CH2)6—CH(CH3)
bond
81
H
(CH2)6—CH(CH3)
bond
82
H
(CH2)6—CH(CH2CH2CH3)
bond
83
H
(CH2)7—(CH3)
bond
84
H
(CH2)7(CH2CH2CH3)
bond
85
H
(CH2)7(CH3)
bond
86
H
(CH2)7
bond
87
—C(O)NH—(CH2)7—COOH
(CH2)7
bond
88
—C(O)NH—(CH2)9—OH
CH2
bond
89
—C(O)NH—(CH2)7—COOH
(CH2)7
bond
90
—C(O)NH—(CH2)9—COOH
(CH2)9
bond
91
—C(O)NH—(CH2)7—COOH
(CH2)7
bond
92
—O(CH2)5COOH
(CH2)5
bond
93
CH3
(CH2)7
bond
94
CH3
(CH2)5
bond
and salts thereof.

582 more elements

A pharmaceutical composition comprising:

(A) a biologically active agent;
and
(C) at least one compound having the formula
Cpd
#
R1
R2
R3
R4
1
H
H
H
H
2
H
H
H
H
3
H
H
H
H
4
H
H
H
H
5
H
H
H
H
6
H
H
H
H
7
H
H
H
H
8
H
H
H
H
9
H
H
H
H
10
H
H
H
H
11
H
H
H
H
12
H
H
H
H
13
H
H
H
H
14
H
H
H
H
15
H
H
H
H
16
H
H
H
H
17
H
H
H
H
18
H
H
H
H
19
H
H
H
H
20
H
H
H
H
21
H
H
H
H
22
H
H
Cl
H
23
H
H
Cl
H
24
H
H
H
H
25
H
H
H
H
26
H
H
H
H
27
H
H
H
H
28
H
H
H
H
29
H
H
H
H
30
H
H
H
H
31
H
H
H
H
32
H
H
H
H
33
H
H
H
H
34
H
H
H
H
35
H
H
H
H
36
H
H
H
H
37
H
H
H
H
38
H
H
H
OH
39
H
H
H
OCH3
43
H
OH
H
H
44
H
OH
H
H
45
H
OH
H
H
46
H
OH
H
H
47
H
H
OH
H
48
H
H
OH
H
49
H
H
OH
H
50
H
H
OH
H
51
H
H
H
H
52
H
H
H
H
54
H
H
H
H
55
H
H
OCH3
H
56
H
OCH3
H
H
57
H
H
OH
H
58
H
H
CH3
H
59
H
H
H
H
60
H
H
H
H
61
H
H
H
H
62
H
H
C(O)CH3
H
63
H
H
C(O)CH2CH3
H
64
H
C(O)CH3
H
H
65
H
H
H
H
66
H
H
H
H
67
H
H
OH
H
68
H
Cl
H
H
69
H
OCH3
H
H
71
H
H
F
H
72
H
H
H
H
73
H
H
H
H
74
H
NO2
H
H
75
H
H
H
H
76
H
H
H
H
77
H
H
H
H
78
H
H
H
H
79
H
H
H
H
80
H
H
OCH3
H
81
H
H
OH
H
82
H
H
OH
H
83
H
H
OH
H
84
H
H
OH
H
85
H
H
OCH3
H
86
H
H
OCH3
H
87
H
H
H
H
88
H
H
H
H
89
H
H
Cl
H
90
H
H
H
H
91
H
OCH3
H
H
92
H
H
H
H
93
H
CH3
H
H
94
H
CH3
H
H
95
H
H
NO2
H
96
H
H
NH2
H
97
H
CH3
H
H
Cpd
#
R5
R6
R7
1
C(O)CH3
CH2
para-
Ph
2
OH
CH2
para-
Ph
3
OH
CH2
bond
4
OH
(CH2)3
bond
5
OH
(CH2)5
bond
6
OH
(CH2)6
bond
7
OH
(CH2)7
bond
8
OH
(CH2)9
bond
9
C(O)CH3
(CH2)3
bond
10
C(O)CH3
(CH2)4
bond
11
C(O)CH3
(CH2)5
bond
12
C(O)CH3
(CH2)7
bond
13
H
CH2
bond
14
H
(CH2)3
bond
15
H
(CH2)5
bond
16
H
(CH2)9
bond
17
H
(CH2)10
bond
18
CH═CHCH3
(CH2)7
bond
19
NH2
(CH2)7
bond
20
NO2
(CH2)7
bond
21
NH2
(CH2)4
bond
22
NH2
(CH2)7
bond
23
NH2
(CH2)4
bond
24
NHC(O)CH3
(CH2)7
bond
25
CH═CHCO2H
(CH2)7
bond
26
C(O)CH2CH3
(CH2)3
bond
27
C(O)CH2CH3
(CH2)5
bond
28
C(O)CH2CH3
(CH2)7
bond
29
C(O)CH2CH3
(CH2)9
bond
30
C(O)NH2
(CH2)7
bond
31
C(O)NHCH3
(CH2)7
bond
32
COOH
(CH2)7
bond
33
C(O)NHCH2CH3
(CH2)7
bond
34
C(O)NHCH(CH3)2
(CH2)7
bond
35
OCH3
(CH2)7
bond
36
CH(OH)CH3
(CH2)7
bond
37
C(CH3)2OH
CH2
para-
Ph
38
C(O)CH3
(CH2)7
bond
39
C(O)CH3
(CH2)7
bond
43
H
(CH2)7
bond
44
H
(CH2)9
bond
45
H
(CH2)5
bond
46
H
(CH2)3
bond
47
H
(CH2)7
bond
48
H
(CH2)9
bond
49
H
(CH2)5
bond
50
H
(CH2)3
bond
51
C(O)NHCH3
(CH2)9
bond
52
C(O)NH2
CH2
para-
Ph
54
C(O)CH3
(CH2)9
bond
55
C(O)CH3
(CH2)7
bond
56
C(O)CH3
(CH2)7
bond
57
C(O)CH3
(CH2)7
bond
58
C(O)CH3
(CH2)5
bond
59
C(O)H
CH2
para-
Ph
60
C(O)H
(CH2)5
bond
61
C(O)H
(CH2)7
bond
62
H
(CH2)7
bond
63
H
(CH2)7
bond
64
H
(CH2)7
bond
65
H
(CH2)7
bond
66
H
CH2
para-
Ph
67
H
CH2
para-
Ph
68
H
(CH2)7
bond
69
H
(CH2)7
bond
71
F
(CH2)7
bond
72
OH
(CH2)10
bond
73
Cl
(CH2)7
bond
74
OH
(CH2)7
bond
75
F
(CH2)4
bond
76
CF3
(CH2)4
bond
77
F
(CH2)7
bond
78
Cl
CH2
para-
Ph
79
OH
CH2CH(OH)
para-
Ph
80
H
(CH2)6—CH(CH3)
bond
81
H
(CH2)6—CH(CH3)
bond
82
H
(CH2)6—CH(CH2CH2CH3)
bond
83
H
(CH2)7—(CH3)
bond
84
H
(CH2)7(CH2CH2CH3)
bond
85
H
(CH2)7(CH3)
bond
86
H
(CH2)7
bond
87
—C(O)NH—(CH2)7—COOH
(CH2)7
bond
88
—C(O)NH—(CH2)9—OH
CH2
bond
89
—C(O)NH—(CH2)7—COOH
(CH2)7
bond
90
—C(O)NH—(CH2)9—COOH
(CH2)9
bond
91
—C(O)NH—(CH2)7—COOH
(CH2)7
bond
92
—O(CH2)5COOH
(CH2)5
bond
93
CH3
(CH2)7
bond
94
CH3
(CH2)5
bond
95
H
para-Ph
bond
96
H
para-Ph
bond
97
CH3
(CH2)3—(C(CH3)2)
Bond
and salts thereof.

849 more elements

A pharmaceutical composition comprising:

(A) a compound selected from the group consisting of
Cpd #
R1
R2
R3
R4
R5
R6
R7
5
H
H
H
H
OH
(CH2)5
bond
6
H
H
H
H
OH
(CH2)6
bond
7
H
H
H
H
OH
(CH2)7
bond
8
H
H
H
H
OH
(CH2)9
bond
43
H
OH
H
H
H
(CH2)7
bond
44
H
OH
H
H
H
(CH2)9
bond
45
H
OH
H
H
H
(CH2)5
bond
47
H
H
OH
H
H
(CH2)7
bond
48
H
H
OH
H
H
(CH2)9
bond
and salts thereof;
and
(B) a biologically active agent comprising at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, small polar organic molecule, or lipid.

81 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/458,331Filed 18 Jul 2006 · continuation
Priority: 5 Nov 1999
Published: US 2006/0264513 A123 Nov 2006
Granted: 2 Apr 2013
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07C 59/64
Containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups:…
C07C 59/42
Unsaturated compounds: containing hydroxy or O-metal groups
C07C 59/56
Containing hydroxy or O-metal groups: containing halogen
C07C 59/74
Unsaturated compounds: containing —CHO groups

Family

Application60/163,806Us provisional application · filed 5 Nov 1999
Application60/231,836Us provisional application · filed 6 Sep 2000
Application60/237,233Us provisional application · filed 2 Oct 2000
PCT/US00/30662Parent of this continuation · filed 6 Nov 2000
US 2006/0264513 A1Pre-grant publication · published 23 Nov 2006
Application10/129,467Parent of this continuation
US 7,129,274 B1Parent of this continuation
US 8,410,309 B2This patent

From the US filing history. Foreign family members aren’t listed.

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US 8,410,309 B2Granted

Phenoxy carboxylic acid compounds and compositions for delivering active agents

AssigneeEmisphere Technologies, Inc.

InventorsAndrea Leone-Bay, Kelly Kraft, Destardi Moye-Sherman, David Gschneidner, Maria Aurora P. Boyd, Puchun Liu, Pingwah Tang, Jun Liao, John Smart, John J. Freeman, Jr.

Life of this patent

Estimating the term…

Abstract

Phenoxy carboxylic acid compounds and compositions for the delivery of active agents are provided. Methods of administration and preparation are provided as well.

Claims23

Dependent claims

A compound having the formula

and salts thereof, wherein
R1 is H, —OH, halogen, C2-C4 alkenyl, C1-C4 alkoxy, —C(O)R8, —NO2, —NR9R10, or —N+R9R10R11 (R12)−;
R2 is H, —OH, halogen, C2-C4 alkenyl, C2-C4 alkoxy, —C(O)R8, —NO2, —NR9R10, or —N+R9R10R11 (R12);
R3 is H, halogen, C2-C4 alkenyl, C1-C4 alkoxy, —C(O)R8, —NO2, —NR9R10, or —N+R9R10R11 (R12);
R4 is H, —OH, halogen, C2-C4 alkenyl, C2-C4 alkoxy, —C(O)R8, —NO2, —NR9R10, or —N+R9R10R11 (R12);
R5 is —NO2, halogen, —NR14R15,—N+R14R15R16 (R13)−, amide, C1-C12 alkoxy, C2-C12 alkenyl, carbamate, carbonate, ureido, or —C(O)R18;
R5 is optionally substituted with halogen, —OH, —SH, or —COOH;
R5 is optionally interrupted by O, N, S, or —C(O)—;
R6 is a C4-C12 linear or branched alkyl, C2-C12 linear or branched alkenyl, or aryl;
R6 is optionally substituted with a C1-C4 alkyl, C2-C4 alkenyl, C1-C4 alkoxy, —OH, —SH, halogen, —NH2, or —CO2R8;
R6 is optionally interrupted by O or N;
R7 is a bond or aryl;
R7 is optionally substituted with —OH, halogen, —C(O)CH3, —NR10R11, or —N+R10R11R12 (R13)−;
R8 is C1-C4 alkyl, or C2-C4 alkenyl;
R9, R10, R11, and R12 are independently H or C1-C10 alkyl;
R13 is a halide, hydroxide, sulfate, tetrafluoroborate, or phosphate;
and
R14, R15 and R16 are independently C1-C10 alkyl, C2-C12 alkenyl, —C(O)R7;
R17 is —OH, C1-C10 alkyl, or C2-C12 alkenyl;
and
R18 is C1-C6 alkyl, —OH, —NR14R15, or N+R14R15R16(R13).

18 more elements

A compound selected from the group consisting of

Cpd
#
R1
R2
R3
R4
1
H
H
H
H
2
H
H
H
H
9
H
H
H
H
10
H
H
H
H
11
H
H
H
H
12
H
H
H
H
18
H
H
H
H
19
H
H
H
H
20
H
H
H
H
22
H
H
Cl
H
23
H
H
Cl
H
24
H
H
H
H
25
H
H
H
H
26
H
H
H
H
27
H
H
H
H
28
H
H
H
H
29
H
H
H
H
30
H
H
H
H
31
H
H
H
H
32
H
H
H
H
33
H
H
H
H
34
H
H
H
H
35
H
H
H
H
36
H
H
H
H
37
H
H
H
H
38
H
H
H
OH
39
H
H
H
OCH3
51
H
H
H
H
52
H
H
H
H
54
H
H
H
H
55
H
H
OCH3
H
56
H
OCH3
H
H
57
H
H
OH
H
58
H
H
CH3
H
59
H
H
H
H
61
H
H
H
H
62
H
H
C(O)CH3
H
63
H
H
C(O)CH2CH3
H
64
H
C(O)CH3
H
H
68
H
Cl
H
H
71
H
H
F
H
72
H
H
H
H
73
H
H
H
H
74
H
NO2
H
H
75
H
H
H
H
76
H
H
H
H
77
H
H
H
H
79
H
H
H
H
80
H
H
OCH3
H
81
H
H
OH
H
82
H
H
OH
H
83
H
H
OH
H
84
H
H
OH
H
85
H
H
OCH3
H
86
H
H
OCH3
H
87
H
H
H
H
88
H
H
H
H
89
H
H
Cl
H
90
H
H
H
H
91
H
OCH3
H
H
92
H
H
H
H
93
H
CH3
H
H
94
H
CH3
H
H
Cpd
#
R5
R6
R7
1
C(O)CH3
CH2
para-
Ph
2
OH
CH2
para-
Ph
9
C(O)CH3
(CH2)3
bond
10
C(O)CH3
(CH2)4
bond
11
C(O)CH3
(CH2)5
bond
12
C(O)CH3
(CH2)7
bond
18
CH═CHCH3
(CH2)7
bond
19
NH2
(CH2)7
bond
20
NO2
(CH2)7
bond
22
NH2
(CH2)7
bond
23
NH2
(CH2)4
bond
24
NHC(O)CH3
(CH2)7
bond
25
CH═CHCO2H
(CH2)7
bond
26
C(O)CH2CH3
(CH2)3
bond
27
C(O)CH2CH3
(CH2)5
bond
28
C(O)CH2CH3
(CH2)7
bond
29
C(O)CH2CH3
(CH2)9
bond
30
C(O)NH2
(CH2)7
bond
31
C(O)NHCH3
(CH2)7
bond
32
COOH
(CH2)7
bond
33
C(O)NHCH2CH3
(CH2)7
bond
34
C(O)NHCH(CH3)2
(CH2)7
bond
35
OCH3
(CH2)7
bond
36
CH(OH)CH3
(CH2)7
bond
37
C(CH3)2OH
CH2
para-
Ph
38
C(O)CH3
(CH2)7
bond
39
C(O)CH3
(CH2)7
bond
51
C(O)NHCH3
(CH2)9
bond
52
C(O)NH2
CH2
para-
Ph
54
C(O)CH3
(CH2)9
bond
55
C(O)CH3
(CH2)7
bond
56
C(O)CH3
(CH2)7
bond
57
C(O)CH3
(CH2)7
bond
58
C(O)CH3
(CH2)5
bond
59
C(O)H
CH2
para-
Ph
61
C(O)H
(CH2)7
bond
62
H
(CH2)7
bond
63
H
(CH2)7
bond
64
H
(CH2)7
bond
68
H
(CH2)7
bond
71
F
(CH2)7
bond
72
OH
(CH2)10
bond
73
Cl
(CH2)7
bond
74
OH
(CH2)7
bond
75
F
(CH2)4
bond
76
CF3
(CH2)4
bond
77
F
(CH2)7
bond
79
OH
CH2CH(OH)
para-
Ph
80
H
(CH2)6—CH(CH3)
bond
81
H
(CH2)6—CH(CH3)
bond
82
H
(CH2)6—CH(CH2CH2CH3)
bond
83
H
(CH2)7—(CH3)
bond
84
H
(CH2)7(CH2CH2CH3)
bond
85
H
(CH2)7(CH3)
bond
86
H
(CH2)7
bond
87
—C(O)NH—(CH2)7—COOH
(CH2)7
bond
88
—C(O)NH—(CH2)9—OH
CH2
bond
89
—C(O)NH—(CH2)7—COOH
(CH2)7
bond
90
—C(O)NH—(CH2)9—COOH
(CH2)9
bond
91
—C(O)NH—(CH2)7—COOH
(CH2)7
bond
92
—O(CH2)5COOH
(CH2)5
bond
93
CH3
(CH2)7
bond
94
CH3
(CH2)5
bond
and salts thereof.

582 more elements

A pharmaceutical composition comprising:

(A) a biologically active agent;
and
(C) at least one compound having the formula
Cpd
#
R1
R2
R3
R4
1
H
H
H
H
2
H
H
H
H
3
H
H
H
H
4
H
H
H
H
5
H
H
H
H
6
H
H
H
H
7
H
H
H
H
8
H
H
H
H
9
H
H
H
H
10
H
H
H
H
11
H
H
H
H
12
H
H
H
H
13
H
H
H
H
14
H
H
H
H
15
H
H
H
H
16
H
H
H
H
17
H
H
H
H
18
H
H
H
H
19
H
H
H
H
20
H
H
H
H
21
H
H
H
H
22
H
H
Cl
H
23
H
H
Cl
H
24
H
H
H
H
25
H
H
H
H
26
H
H
H
H
27
H
H
H
H
28
H
H
H
H
29
H
H
H
H
30
H
H
H
H
31
H
H
H
H
32
H
H
H
H
33
H
H
H
H
34
H
H
H
H
35
H
H
H
H
36
H
H
H
H
37
H
H
H
H
38
H
H
H
OH
39
H
H
H
OCH3
43
H
OH
H
H
44
H
OH
H
H
45
H
OH
H
H
46
H
OH
H
H
47
H
H
OH
H
48
H
H
OH
H
49
H
H
OH
H
50
H
H
OH
H
51
H
H
H
H
52
H
H
H
H
54
H
H
H
H
55
H
H
OCH3
H
56
H
OCH3
H
H
57
H
H
OH
H
58
H
H
CH3
H
59
H
H
H
H
60
H
H
H
H
61
H
H
H
H
62
H
H
C(O)CH3
H
63
H
H
C(O)CH2CH3
H
64
H
C(O)CH3
H
H
65
H
H
H
H
66
H
H
H
H
67
H
H
OH
H
68
H
Cl
H
H
69
H
OCH3
H
H
71
H
H
F
H
72
H
H
H
H
73
H
H
H
H
74
H
NO2
H
H
75
H
H
H
H
76
H
H
H
H
77
H
H
H
H
78
H
H
H
H
79
H
H
H
H
80
H
H
OCH3
H
81
H
H
OH
H
82
H
H
OH
H
83
H
H
OH
H
84
H
H
OH
H
85
H
H
OCH3
H
86
H
H
OCH3
H
87
H
H
H
H
88
H
H
H
H
89
H
H
Cl
H
90
H
H
H
H
91
H
OCH3
H
H
92
H
H
H
H
93
H
CH3
H
H
94
H
CH3
H
H
95
H
H
NO2
H
96
H
H
NH2
H
97
H
CH3
H
H
Cpd
#
R5
R6
R7
1
C(O)CH3
CH2
para-
Ph
2
OH
CH2
para-
Ph
3
OH
CH2
bond
4
OH
(CH2)3
bond
5
OH
(CH2)5
bond
6
OH
(CH2)6
bond
7
OH
(CH2)7
bond
8
OH
(CH2)9
bond
9
C(O)CH3
(CH2)3
bond
10
C(O)CH3
(CH2)4
bond
11
C(O)CH3
(CH2)5
bond
12
C(O)CH3
(CH2)7
bond
13
H
CH2
bond
14
H
(CH2)3
bond
15
H
(CH2)5
bond
16
H
(CH2)9
bond
17
H
(CH2)10
bond
18
CH═CHCH3
(CH2)7
bond
19
NH2
(CH2)7
bond
20
NO2
(CH2)7
bond
21
NH2
(CH2)4
bond
22
NH2
(CH2)7
bond
23
NH2
(CH2)4
bond
24
NHC(O)CH3
(CH2)7
bond
25
CH═CHCO2H
(CH2)7
bond
26
C(O)CH2CH3
(CH2)3
bond
27
C(O)CH2CH3
(CH2)5
bond
28
C(O)CH2CH3
(CH2)7
bond
29
C(O)CH2CH3
(CH2)9
bond
30
C(O)NH2
(CH2)7
bond
31
C(O)NHCH3
(CH2)7
bond
32
COOH
(CH2)7
bond
33
C(O)NHCH2CH3
(CH2)7
bond
34
C(O)NHCH(CH3)2
(CH2)7
bond
35
OCH3
(CH2)7
bond
36
CH(OH)CH3
(CH2)7
bond
37
C(CH3)2OH
CH2
para-
Ph
38
C(O)CH3
(CH2)7
bond
39
C(O)CH3
(CH2)7
bond
43
H
(CH2)7
bond
44
H
(CH2)9
bond
45
H
(CH2)5
bond
46
H
(CH2)3
bond
47
H
(CH2)7
bond
48
H
(CH2)9
bond
49
H
(CH2)5
bond
50
H
(CH2)3
bond
51
C(O)NHCH3
(CH2)9
bond
52
C(O)NH2
CH2
para-
Ph
54
C(O)CH3
(CH2)9
bond
55
C(O)CH3
(CH2)7
bond
56
C(O)CH3
(CH2)7
bond
57
C(O)CH3
(CH2)7
bond
58
C(O)CH3
(CH2)5
bond
59
C(O)H
CH2
para-
Ph
60
C(O)H
(CH2)5
bond
61
C(O)H
(CH2)7
bond
62
H
(CH2)7
bond
63
H
(CH2)7
bond
64
H
(CH2)7
bond
65
H
(CH2)7
bond
66
H
CH2
para-
Ph
67
H
CH2
para-
Ph
68
H
(CH2)7
bond
69
H
(CH2)7
bond
71
F
(CH2)7
bond
72
OH
(CH2)10
bond
73
Cl
(CH2)7
bond
74
OH
(CH2)7
bond
75
F
(CH2)4
bond
76
CF3
(CH2)4
bond
77
F
(CH2)7
bond
78
Cl
CH2
para-
Ph
79
OH
CH2CH(OH)
para-
Ph
80
H
(CH2)6—CH(CH3)
bond
81
H
(CH2)6—CH(CH3)
bond
82
H
(CH2)6—CH(CH2CH2CH3)
bond
83
H
(CH2)7—(CH3)
bond
84
H
(CH2)7(CH2CH2CH3)
bond
85
H
(CH2)7(CH3)
bond
86
H
(CH2)7
bond
87
—C(O)NH—(CH2)7—COOH
(CH2)7
bond
88
—C(O)NH—(CH2)9—OH
CH2
bond
89
—C(O)NH—(CH2)7—COOH
(CH2)7
bond
90
—C(O)NH—(CH2)9—COOH
(CH2)9
bond
91
—C(O)NH—(CH2)7—COOH
(CH2)7
bond
92
—O(CH2)5COOH
(CH2)5
bond
93
CH3
(CH2)7
bond
94
CH3
(CH2)5
bond
95
H
para-Ph
bond
96
H
para-Ph
bond
97
CH3
(CH2)3—(C(CH3)2)
Bond
and salts thereof.

849 more elements

A pharmaceutical composition comprising:

(A) a compound selected from the group consisting of
Cpd #
R1
R2
R3
R4
R5
R6
R7
5
H
H
H
H
OH
(CH2)5
bond
6
H
H
H
H
OH
(CH2)6
bond
7
H
H
H
H
OH
(CH2)7
bond
8
H
H
H
H
OH
(CH2)9
bond
43
H
OH
H
H
H
(CH2)7
bond
44
H
OH
H
H
H
(CH2)9
bond
45
H
OH
H
H
H
(CH2)5
bond
47
H
H
OH
H
H
(CH2)7
bond
48
H
H
OH
H
H
(CH2)9
bond
and salts thereof;
and
(B) a biologically active agent comprising at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, small polar organic molecule, or lipid.

81 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/458,331Filed 18 Jul 2006 · continuation
Priority: 5 Nov 1999
Published: US 2006/0264513 A123 Nov 2006
Granted: 2 Apr 2013
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07C 59/64
Containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups:…
C07C 59/42
Unsaturated compounds: containing hydroxy or O-metal groups
C07C 59/56
Containing hydroxy or O-metal groups: containing halogen
C07C 59/74
Unsaturated compounds: containing —CHO groups

Family

Application60/163,806Us provisional application · filed 5 Nov 1999
Application60/231,836Us provisional application · filed 6 Sep 2000
Application60/237,233Us provisional application · filed 2 Oct 2000
PCT/US00/30662Parent of this continuation · filed 6 Nov 2000
US 2006/0264513 A1Pre-grant publication · published 23 Nov 2006
Application10/129,467Parent of this continuation
US 7,129,274 B1Parent of this continuation
US 8,410,309 B2This patent

From the US filing history. Foreign family members aren’t listed.