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Compositions of iodophenoxy alkanes and iodophenyl ethers for visualization of the gastrointestinal tract
| Details |
Inventors: Illig, Carl R.; Cooper, Eugene R.; Toner, John L.; Upson, Donald A.; Douty, Brent D.; Caulfield, Thomas J.; Bacon, Edward R.; Estep, Kimberly G.; Josef, Kurt A.; Robinson, Shaughnessy; Spara, Paul P.;
Assignee: Sterling Winthrop Inc. (Malvern, PA)
Primary Examiner: Dees; Jose G.
Assistant Examiner: Jones; Dwayne C.
Attorney, Agent or Firm: Rosenstein; Arthur, Balogh; Imre
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 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 =CR.sub.4).sub.m Q, or (CR.sub.1 R.sub.2).sub.p -C.ident.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 1-4; 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. |
|
DETAILED DESCRIPTION OF THE INVENTION Compounds of the present invention can be made according to the schematic procedure shown or other methods using commercially available starting materials, intermediates and reagents.
Starting materials, reagents and solvents can be obtained from chemical suppliers such as Aldrich, Baker and Eastman Chemical Companies, or they may be prepared by techniques known in the art.
##STR3## wherein X=Halogen, OSO.
sub.
2 CH.
sub.
3 x=1-4 I.
sub.
n, Z and R are as described above.
##STR4## wherein A=--(CR.
sub.
3 =CR.
sub.
4).
sub.
m -- --C.
ident.
C-- Y=Halogen, OSO.
sub.
2 CH.
sub.
3 x=1-4 and I.
sub.
n, Z, R.
sub.
1, R.
sub.
2, R.
sub.
3, R.
sub.
4 and Q are as described above.
The following examples will further illustrate the compounds used in the present invention.
EXAMPLE 1 2-(4-Iodophenoxy)-decane ##STR5## To a solution of 2-decanol (5.
0 ml, 26.
0 mmol) in dry CH.
sub.
2 Cl.
sub.
2 (52 ml) under an N.
sub.
2 atmosphere was added diisopropylethylamine (5.
6 ml, 32.
1 mmol).
The reaction flask was immersed in an ice/water bath.
After stirring for 10 minutes, methanesulfonyl chloride (2.
8 ml, 36.
1 mmol) was added via syringe over a period of 10 minutes.
After stirring for 3 hrs, the reaction was diluted with cold CH.
sub.
2 Cl.
sub.
2 (200 ml) and poured into cold 5% aqueous HCl (100 ml).
The layers were separated and the organic phase washed with cold 5% aqueous HCl (50 ml) followed by brine (2.
times.
50 ml).
The CH.
sub.
2 Cl.
sub.
2 layer was dried (Na.
sub.
2 SO.
sub.
4), filtered and evaporated in vacuo at 25.
degree.
C.
The resulting light yellow oil was pumped under reduced pressure for 2 hrs to provide 2-methanesulfonyloxydecane (6.
5 g, 93.
5%) as a light yellow oil.
Without further purification, the above product (6.
5 g, 24.
3 mmol) was dissolved in 50 ml dry N,N-dimethylformamide (DMF) with stirring.
4-Iodophenol (4.
8 g, 21.
8 mmol) and potassium carbonate (3.
4 g, 24.
6 mmol) were then added to the reaction flask which was immersed in an oil bath and heated to 57.
degree.
C.
over a period of 0.
5 hr
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