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US5308607A Expired / Lapsed US ⏱️ 0.0 years remaining

Compositions of alkylbenzenes for visualization of the gastrointestinal tract using X-ray contrast

Assignee: GE Healthcare AS
•
Filing: 1993-02-04
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Granted: 1994-05-03
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Expires: 2013-02-04
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Abstract

Abstract Disclosed are contrast agents of the formula <IMAGE> contained in aqueous compositions and methods for their use in diagnostic radiology of the gastrointestinal tract wherein R=C1-C25 alkyl, cycloalkyl, unsaturated allyl or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy, (CR1R2)p-(CR3=CR4)mQ, or (CR1R2)p-C 3BOND C-Q; R1, R2, R3 and R4 are independently H, lower-alkyl, optionally substituted with halo; n is 1-5; m is 1-5; p is 1-10; and Q is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkyl.

Inventors

  • 👤 Kurt A. Josef
  • 👤 Edward R. Bacon
  • 👤 Kimberly G. Estep
  • 👤 Carl R. Illig
  • 👤 Brent D. Douty

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 11:22
CPC Classifications
A; A61; A61K; A61K49/00; A61K49/04; C; C07; C07C; C07C17/00; C07C17/35; C07C17/354; A61K49/0404; A61K49/0409; A61K49/0433; A61K49/0438; A61K49/0447; A61K49/0461; C07C17/093; C07C17/10; C07C17/12; C07C17/26; C07C17/263; C07C17/2635; C07C25/00; C07C25/02; C07C25/24; C07C69/00; C07C69/62; C07C69/65

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 181 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: ##STR15## wherein R is methyl, ethyl, n-propyl, C 4 -C 25 alkyl, cycloalkyl, unsaturated allyl or halo-lower-alkyl, each of which may be optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl (CR 1 R 2 ) p --(CR 3 ═CR 4 ) m Q, or (CR 1 R 2 ) p --C.tbd.C--Q; R 1 , R 2 , R 3 and R 4 are independently H, lower-alkyl optionally]substituted with halo; n is 2-5; m is 2-5; p is 1-10; and Q is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkyl in an aqueous, pharmaceutically acceptable carrier, said pharmaceutically acceptable carrier containing at least one surfactant selected from the group consisting of a zwitterionic surfactant, trimethylammonium bromide, sodium lauryl sulfate, sodium heptadecyl sulphate, alkyl benzenesulphonic acid, sodium butylnaphthalene sulfonate, sulphosuccinate, carboxylic esters, carboxylic amides, ethoxylated alkylphenols and ethoxylated aliphatic alcohols, sorbitan esters, polyoxyethylene alkyl ethers and polyoxyethylene sorbitan fatty acid esters.
Claim 2
Dependent Claim 181 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: ##STR15## wherein R is methyl, ethyl, n-propyl, C 4 -C 25 alkyl, cycloalkyl, unsaturated allyl or halo-lower-alkyl, each of which may be optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl (CR 1 R 2 ) p --(CR 3 ═CR 4 ) m Q, or (CR 1 R 2 ) p --C.tbd.C--Q; R 1 , R 2 , R 3 and R 4 are independently H, lower-alkyl optionally]substituted with halo; n is 2-5; m is 2-5; p is 1-10; and Q is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkyl in an aqueous, pharmaceutically acceptable carrier, said pharmaceutically acceptable carrier containing at least one surfactant selected from the group consisting of a zwitterionic surfactant, trimethylammonium bromide, sodium lauryl sulfate, sodium heptadecyl sulphate, alkyl benzenesulphonic acid, sodium butylnaphthalene sulfonate, sulphosuccinate, carboxylic esters, carboxylic amides, ethoxylated alkylphenols and ethoxylated aliphatic alcohols, sorbitan esters, polyoxyethylene alkyl ethers and polyoxyethylene sorbitan fatty acid esters.
Claim 3
Dependent Claim 24 words
The x-ray contrast composition of claim 1 wherein said contrast agent is selected from the group consisting of: 1,3,5-triethyl-2,4,6-triiodobenzene, 1,3,5-tri-(3-methylbutyl)-2,4,6-triiodobenzene, 1,3,5-tri-N-pentyl-2,4,6-triiodobenzene, 1,3,5-tri-N-butyl-2,4,6-triiodobenzene and 1,3,5-tri-(4-methylpentyl)-2,4,6-triiodobenzene.
Claim 4
Dependent Claim 33 words
The x-ray contrast composition of claim 1 wherein said contrast agent is selected from the group consisting of: 1,3,5-tri-N-propyl-2,4,6-triiodobenzene, 1,3,5-tri-N-heptyl-2,4,6-triiodobenzene, 1,3,5-tri-N-hexyl -2,4,6-triiodobenzene, 2-(4-iodophenyl)nonane, 9-(p-iodophenyl)-10-undecenoic acid, and ethyl ester and (E)-11-(p-iodophenyl)-9-undecenoic acid, ethyl ester.
Claim 5
Dependent Claim 25 words
The x-ray contrast composition of claim 1 wherein said surfactant is present of from about 0.01% w/v to about 15% w/v in said aqueous composition.
Claim 6
Independent Claim 208 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, having the formula; ##STR16## wherein R is methyl, ethyl, n-propyl, C 4 -C 25 alkyl, cycloalkyl, unsaturated allyl or halo-lower-alkyl, each of which may be optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl (CR 1 R 2 ) p --(CR 3 ═CR 4 ) m Q, or (CR 1 R 2 ) p --C.tbd.C--Q; R 1 , R 2 , R 3 and R 4 are independently H, lower-alkyl optionally]substituted with halo; n is 2-5; m is 2-5; p is 1-10; and Q is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkyl in an aqueous, pharmaceutically acceptable carrier, said pharmaceutically acceptable carrier containing at least one surfactant selected from the group consisting of a zwitterionic surfactant, trimethylammonium bromide, sodium lauryl sulfate, sodium heptadecyl sulphate, alkyl benzenesulphonic acid, sodium butylnaphthalene sulfonate, sulphosuccinate, carboxylic esters, carboxylic amides, ethoxylated alkylphenols and ethoxylated aliphatic alcohols, sorbitan esters, polyoxyethylene alkyl ethers and polyoxyethylene sorbitan fatty acid esters; and performing an x-ray examination of the patient.
Claim 7
Independent Claim 208 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, having the formula; ##STR16## wherein R is methyl, ethyl, n-propyl, C 4 -C 25 alkyl, cycloalkyl, unsaturated allyl or halo-lower-alkyl, each of which may be optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl (CR 1 R 2 ) p --(CR 3 ═CR 4 ) m Q, or (CR 1 R 2 ) p --C.tbd.C--Q; R 1 , R 2 , R 3 and R 4 are independently H, lower-alkyl optionally]substituted with halo; n is 2-5; m is 2-5; p is 1-10; and Q is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkyl in an aqueous, pharmaceutically acceptable carrier, said pharmaceutically acceptable carrier containing at least one surfactant selected from the group consisting of a zwitterionic surfactant, trimethylammonium bromide, sodium lauryl sulfate, sodium heptadecyl sulphate, alkyl benzenesulphonic acid, sodium butylnaphthalene sulfonate, sulphosuccinate, carboxylic esters, carboxylic amides, ethoxylated alkylphenols and ethoxylated aliphatic alcohols, sorbitan esters, polyoxyethylene alkyl ethers and polyoxyethylene sorbitan fatty acid esters; and performing an x-ray examination of the patient.
Claim 8
Dependent Claim 24 words
The method of claim 5 wherein said contrast agent is selected from the group consisting of: 1,3,5-triethyl-2,4,6-triiodobenzene, 1,3,5-tri-(3-methylbutyl) -2,4,6-triiodobenzene, 1,3,5-tri-N-pentyl,2,4,6-triiodobenzene, 1,3,5-tri-N-butyl-2,4,6-triiodobenzene and 1,3,5-tri-(4-methylpentyl) -2,4,6-triiodobenzene.
Claim 9
Dependent Claim 31 words
The method of claim 5 wherein said contrast agent is selected from the group consisting of: 1,3,5-tri-N-propyl-2,4,6-triiodobenzene, 1,3,5-tri-N-heptyl -2,4,6-triiodobenzene, 1,3,5-tri-N-hexyl-2,4,6-triiodobenzene, 2-(4-iodophenyl)nonane, 9-(p-iodophenyl)-10-undecenoic acid, and ethyl ester and (E)-11-(p-iodophenyl)-9-undecenoic acid, ethyl ester.
Claim 10
Dependent Claim 32 words
The method of claim 5 wherein said 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 11
Dependent Claim 32 words
The method of claim 5 wherein said 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.

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