# US 5,344,638 A · Compositions of iodobenzoic acid derivatives for visualization of the gastrointestinal tract

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- Number: US 5,344,638 A
- Document ID: US5344638A
- Status: Granted
- Kind: A
- Application number: 08/031,384
- Filed: 1993-03-11
- Granted: 1994-09-06
- Earliest claimed: 1993-03-11
- Assignees: Sterling Winthrop Inc.
- Inventors: Carl R. Illig; Brent D. Douty
- Web page: https://patentgrep.com/patent/US5344638A

## CPC

- A61K 49/0433: {containing an organic halogenated X-ray contrast-enhancing agent}
- C07C 69/76: Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C 69/92: with etherified hydroxyl groups
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## 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 wherein Z=H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups; R=C.sub.1 -C.sub.25 alkyl, cycloalkyl, or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy, (CR.sub.1 R.sub.2).sub.p --(CR.sub.3 .dbd.CR.sub.4).sub.m Q, or (CR.sub.1 R.sub.2).sub.p --C.tbd.C--Q; R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently lower-alkyl, optionally substituted with halo; x is 1-3 y is 1-4; n is 1-5; m is 1-15; 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.

## Claims

### Claim 1

A compound selected from the group consisting of: 2-octyl 2,3,5-triiodobenzoate, 3,3,4,4,5,5,6,6,7,7,8,8-dodecafluoro-2-octyl 2,3,5-triiodobenzoate and bis (2-hexyl) 2,3,5,6-tetraiodoterephthalate, or a pharmaceutically acceptable salt thereof.

### Claim 2

A compound selected from the group consisting of: ethyl 3-(2-octyloxy-2,4,6-triiodobenzoate and bis(2-octyl) 5-(2-octyloxy)-2,4,6-triiodoisophthalate, or a pharmaceutically acceptable salt thereof.

### Claim 3

An orally or rectally administerable x-ray contrast composition for visualization of the gastrointestinal tract comprising a contrast agent selected from the group consisting of: 2-octyl 2,3,5-triiodobenzoate, 3,3,4,4,5,5,6,6,7,7,8,8-dodecafluoro-2-octyl 2,3,5-triiodobenzoate and bis (2-hexyl) 2,3,5,6-tetraiodoterephthalate, or a pharmaceutically acceptable salt thereof, in an aqueous, pharmaceutically acceptable carrier containing a surfactant selected from the group consisting of cationic, anionic, nonionic and zwitterionic surfactants.

### Claim 4

An orally or rectally administerable x-ray contrast composition for visualization of the gastrointestinal tract comprising a contrast agent selected from the group consisting of: ethyl 3-(2-octyloxy)-2,4,6-triiodo-benzoate and bis(2-octyl) 5-(2-octyloxy)-2,4,6-triiodoisophthalate, or a pharmaceutically acceptable salt thereof, in an aqueous, pharmaceutically acceptable carrier containing a surfactant selected from the group consisting of cationic, anionic, nonionic and zwitterionic surfactants.

### Claim 5

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 a contrast agent selected from the group consisting of: 2-octyl 2,3,5-triiodobenzoate, 3,3,4,4,5,5,6,6,7,7,8,8-dodecafluoro-2-octyl 2,3,5-triiodobenzoate and bis (2-hexyl) 2,3,5,6-tetraiodoterephthalate, or a pharmaceutically acceptable salt thereof, in an aqueous, pharmaceutically acceptable carrier containing a surfactant selected from the group consisting of cationic, anionic, nonionic and zwitterionic surfactants.

### Claim 6

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 a contrast agent selected from the group consisting of: ethyl 3-(2-octyloxy)-2,4,6-triiodobenzoate and bis(2-octyl) 5-(2-octyloxy)-2,4,6-triiodoisophthalate, or a pharmaceutically acceptable salt thereof, in an aqueous, pharmaceutically acceptable carrier containing a surfactant selected from the group consisting of cationic, anionic, nonionic and zwitterionic surfactants.