US5318769A
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Compositions of iodophenyl esters for X-ray visualization of the gastrointestinal tract
Assignee: GE Healthcare AS
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Filing: 1993-03-31
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Granted: 1994-06-07
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Expires: 2013-03-31
Abstract
Abstract Disclosed are contrast agents of the formula ##STR1## contained in aqueous compositions and methods for their use in diagnostic radiology of the gastrointestinal tract wherein X= ##STR2## Z=H, halo, C 1 -C 20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups; R=C 1 -C 25 alkyl, cycloalkyl, aryl, or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene, lower-alkoxy-carbonyloxy; n=1-5; y=0-4; and w=1-4 in an aqueous pharmaceutically acceptable carrier.
Inventors
- 👤 Edward R. Bacon
- 👤 Sol J. Daum
- 👤 Kimberly G. Estep
- 👤 Kurt A. Josef
- 👤 Brent D. Douty
- 👤 Carl R. Illig
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 15:54
CPC Classifications
B; B82; B82Y; B82Y5/00; A; A61; A61K; A61K49/00; A61K49/04; A61K49/0404; A61K49/0409; A61K49/0433; C; C07; C07C; C07C309/00; C07C309/63; C07C309/64; C07C309/65; C07C69/00; C07C69/017; C07C69/62; C07C69/63; C07C69/74
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
82 words
A compound of the formula or a pharmaceutically acceptable salt thereof ##STR19## wherein X is ##STR20## Z is H, halo, C 5 -C 20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups; R is C 1 -C 25 alkyl, cycloalkyl, or aryl each of which may be optionally substituted with lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene or lower-alkoxy-carbonyloxy, n is 1-5; y is 0-4; and w is 1-4.
Claim 2
Dependent Claim
82 words
A compound of the formula or a pharmaceutically acceptable salt thereof ##STR19## wherein X is ##STR20## Z is H, halo, C 5 -C 20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups; R is C 1 -C 25 alkyl, cycloalkyl, or aryl each of which may be optionally substituted with lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene or lower-alkoxy-carbonyloxy, n is 1-5; y is 0-4; and w is 1-4.
Claim 3
Dependent Claim
22 words
A compound according to claim 1, selected from the group consisting of: 2,4,6-triiodophenyl 2-ethylhexanoate, 2,4,6-triiodophenyl 2-methylpentanoate, 2,4,6-triiodophenyl 3-cyclopentyl propionate, and 2,4,6-triiodophenyl (2-propyl)pentanoate.
Claim 4
Dependent Claim
17 words
A compound according to claim 1, selected from the group consisting of: 2,4,6-triiodophenyltris-(2-ethylhexanoate), 2,4,6-triiodophenyl dodecanoate, and 2,4,6-triiodophenyl-bis-(2-methylpentanoate).
Claim 5
Dependent Claim
98 words
An orally or rectally administerable x-ray contrast composition for visualization of the gastrointestinal tract comprising a contrast agent having the formula, or a pharmaceutically acceptable salt thereof: ##STR21## wherein X is ##STR22## Z is H, halo, C 5 -C 20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups; R is C 1 -C 25 alkyl, cycloalkyl, or aryl each of which may be optionally substituted with lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene or lower-alkoxy-carbonyloxy, n is 1-5; y is 0-4; and w is 1-4.
Claim 6
Dependent Claim
98 words
An orally or rectally administerable x-ray contrast composition for visualization of the gastrointestinal tract comprising a contrast agent having the formula, or a pharmaceutically acceptable salt thereof: ##STR21## wherein X is ##STR22## Z is H, halo, C 5 -C 20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups; R is C 1 -C 25 alkyl, cycloalkyl, or aryl each of which may be optionally substituted with lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene or lower-alkoxy-carbonyloxy, n is 1-5; y is 0-4; and w is 1-4.
Claim 7
Dependent Claim
27 words
The x-ray contrast composition of claim 4 wherein said contrast agent is selected from the group consisting of: 2,4,6-triiodophenyl 2-ethylhexanoate, 2,4,6-triiodophenyl 2-methylpentanoate, 2,4,6-triiodophenyl 3-cyclopentylpropionate, and 2,4,6-triiodophenyl (2-propyl)pentanoate.
Claim 8
Dependent Claim
23 words
The x-ray contrast composition of claim 5 wherein said contrast agent is selected from the group consisting of: 2,4,6-triiodophenyl-tris-(2-ethylhexanoate), 2,4,6-triiodophenyl dodecanoate, and 2,4,6-triiodophenyl-bis-(2-methylpentanoate).
Claim 9
Dependent Claim
12 words
The x-ray contrast composition of claim 4 containing at least one surfactant.
Claim 10
Dependent Claim
12 words
The x-ray contrast composition of claim 7 wherein said surfactant is cationic.
Claim 11
Dependent Claim
12 words
The x-ray contrast composition of claim 7 wherein said surfactant is anionic.
Claim 12
Dependent Claim
12 words
The x-ray contrast composition of claim 7 wherein said surfactant is zwitterionic.
Claim 13
Dependent Claim
12 words
The x-ray contrast composition of claim 7 wherein said surfactant is nonionic.
Claim 14
Dependent Claim
16 words
The x-ray contrast composition of claim 8 wherein said cationic surfactant is cetyl trimethyl ammonium bromide.
Claim 15
Dependent Claim
33 words
The x-ray contrast composition of claim 9 wherein said anionic surfactant is selected from the group consisting of sodium lauryl sulfate, sodium heptadecyl sulphate, an alkyl benzenesulphonic acid, sodium butylnaphthalene sulfonate and sulphosuccinate.
Claim 16
Dependent Claim
39 words
The x-ray contrast composition of claim 11 wherein said nonionic surfactant is selected from the group consisting of carboxylic esters, carboxylic amides, ethoxylated alkylphenols and ethoxylated aliphatic alcohols, sorbitan esters, polyoxyethylene alkyl ethers and polyoxyethylene sorbitan fatty acid esters.
Claim 17
Independent Claim
119 words
A method of carrying out x-ray examination of the gastrointestinal tract of a patient in need of such examination which comprises orally or rectally administering to the patient an x-ray contrast composition comprising: an x-ray contrast agent, or a pharmaceutically acceptable salt thereof ##STR23## wherein X is ##STR24## Z is H, halo, C 5 -C 20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups; R is C 1 -C 25 alkyl, cycloalkyl, or aryl each of which may be optionally substituted with lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene or lower-alkoxy-carbonyloxy, n is 1-5; y is 0-4; and w is 1-4 in a pharmaceutically acceptable carrier.
Claim 18
Independent Claim
119 words
A method of carrying out x-ray examination of the gastrointestinal tract of a patient in need of such examination which comprises orally or rectally administering to the patient an x-ray contrast composition comprising: an x-ray contrast agent, or a pharmaceutically acceptable salt thereof ##STR23## wherein X is ##STR24## Z is H, halo, C 5 -C 20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups; R is C 1 -C 25 alkyl, cycloalkyl, or aryl each of which may be optionally substituted with lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene or lower-alkoxy-carbonyloxy, n is 1-5; y is 0-4; and w is 1-4 in a pharmaceutically acceptable carrier.
Claim 19
Dependent Claim
25 words
The method of claim 15 wherein said contrast agent is selected from the group consisting of: 2,4,6-triiodophenyl 2-ethylhexanoate, 2,4,6-triiodophenyl 2-methylpentanoate, 2,4,6-triiodophenyl 3-cyclopentylpropionate, and 2,4,6-triiodophenyl (2-propyl)pentanoate.
Claim 20
Dependent Claim
21 words
The method of claim 15 wherein said contrast agent is selected from the group consisting of: 2,4,6-triiodophenyl-tris-(2-ethylhexanoate), 2,4,6-triiodophenyl dodecanoate, and 2,4,6-triiodophenyl-bis-(2-methylpentanoate).
Claim 21
Dependent Claim
34 words
The method of claim 15 wherein the amount of contrast agent administered to said patient contains from about 0.1 to about 16 g iodine/kg body weight for regular x-ray visualization of the gastrointestinal tract.
Claim 22
Dependent Claim
34 words
The method of claim 15 wherein the amount of contrast agent administered to said patient contains from about 1 to about 600 mg iodine/kg body weight for CT scan visualization of the gastrointestinal tract.
Claim 23
Dependent Claim
13 words
The method of claim 15 wherein said dispersion contains at least one surfactant.
Claim 24
Dependent Claim
10 words
The method of claim 20 wherein said surfactant is cationic.
Claim 25
Dependent Claim
10 words
The method of claim 20 wherein said surfactant is anionic.
Claim 26
Dependent Claim
10 words
The method of claim 20 wherein said surfactant is zwitterionic.
Claim 27
Dependent Claim
10 words
The method of claim 20 wherein said surfactant is nonionic.
Claim 28
Dependent Claim
13 words
The method of claim 21 wherein said cationic surfactant is cetyl trimethylammonium bromide.
Claim 29
Dependent Claim
31 words
The method of claim 22 wherein said anionic surfactant is selected from the group consisting of sodium lauryl sulfate; sodium heptadecyl sulphate, an alkyl benzenesulphonic acid, sodium butylnaphthalene sulfonate and sulphosuccinates.
Claim 30
Dependent Claim
39 words
The method of claim 24 wherein said nonionic surface active agent is selected from the group consisting of carboxylic esters, carboxylic amides, ethoxylated alkylphenols and ethoxylated aliphatic alcohols, sorbitan esters, polyoxyethylene alkyl ethers and polyoxyethylene sorbitan fatty acid esters.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1997-06-06 | 1997-12-06 | 1998-06-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-06-06 | 2001-12-06 | 2002-06-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-06-06 | 2005-12-06 | 2006-06-07 | $7700.00 | Window Closed / Lapsed |