US5316755A — Compositions of iodophenoxy alkanes and iodopheny…

Claim 1

Independent Claim 194 words

An orally or rectally administerable aqueous x-ray contrast composition for visualization of the gastrointestinal tract comprising: from about 0.001 to about 75% w/v of a contrast agent having the formula, or a pharmaceutically acceptable salt thereof ##STR39## wherein 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=methyl, ethyl, propyl, C 9 -C 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≡C--Q; R 1 , R 2 , R 3 and R 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 said contrast agent being in the form of an aqueous dispersion in said compostion wherein said dispersion contains from about 0.01 to about 15% w/v of at least one surfactant selected from the group consisting of trimethylammonium bromide, sodium lauryl sulfate, sodium heptadecyl sulphate, an alkyl benzenesulphonic acid, sodium butylnaphthalene sulfonate and sulphosuccinate and zwitterionic surfactants.

Claim 2

Dependent Claim 194 words

An orally or rectally administerable aqueous x-ray contrast composition for visualization of the gastrointestinal tract comprising: from about 0.001 to about 75% w/v of a contrast agent having the formula, or a pharmaceutically acceptable salt thereof ##STR39## wherein 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=methyl, ethyl, propyl, C 9 -C 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≡C--Q; R 1 , R 2 , R 3 and R 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 said contrast agent being in the form of an aqueous dispersion in said compostion wherein said dispersion contains from about 0.01 to about 15% w/v of at least one surfactant selected from the group consisting of trimethylammonium bromide, sodium lauryl sulfate, sodium heptadecyl sulphate, an alkyl benzenesulphonic acid, sodium butylnaphthalene sulfonate and sulphosuccinate and zwitterionic surfactants.

Claim 3

Dependent Claim 30 words

The x-ray contrast composition of claim 1 wherein said contrast agent is selected from the group consisting of: 2-(4-Iodophenoxy)-decane, 2-(2,4,6-triiodophenoxy)-pentadecane, 2-(2,4,6-triiodophenoxy)decane, (2,4,6-triiodophenoxy)-1H, 1H, 2H, 2H - perfluorooctane and 1-(2,4,6-triiodo-3-trifluorophenoxy )octane.

Claim 4

Dependent Claim 13 words

The x-ray contrast composition of claim 1 wherein said contrast agent is 2-(2,4,6-triiodophenoxy)-nonane.

Claim 5

Dependent Claim 24 words

The x-ray contrast composition of claim 1 wherein said contrast agent is selected from the group consisting of: 3-(2,4,6-triiodophenoxy)-nonane, 2-(4-iodophenoxy)-undecane, 2-iodophenoxycyclopentane, 3-iodophenoxycyclopentane and (3,5-dimethyl-2,4,6-triiodophenoxy)cyclopentane.

Claim 6

Dependent Claim 24 words

The x-ray contrast composition of claim 1 wherein said contrast agent is selected from the group consisting of: 2-(4-iodophenoxy)-pentadecane, 4-iodophenoxycyclopentane, 2,4,6-triiodophenoxycyclopentane, 2,4,6-triiodophenoxymethylcyclopentane and 2-(2,4,6-triiodophenoxy)ethylcyclopentane.

Claim 7

Dependent Claim 23 words

The x-ray contrast composition of claim 1 wherein said contrast agent is selected from the group consisting of: (E,E)-1-(2,4,6-triiodophenoxy)-3,7,11-trimethyl-2,6,10-dodecatriene, 1-(2,4,6-triiodophenoxy)-3,7-dimethyl-6-octene, (E)-1-(3,5-dimethyl-2,4,6-triiodophenoxy)-3,7-dimethyl-2,6-octadiene and (E)-1-(2,4,6-triiodophenoxy)-3,7-dimethyl-2,6-octadiene.

Claim 8

Dependent Claim 26 words

The x-ray contrast composition of claim 1 wherein said contrast agent is selected from the group consisting of: 1-(2,4,6-triiodophenoxy)-3-octyne, 2-(2,4,6-triiodophenoxy)-4-octyne, 1-(2,4,6-triiodophenoxy)-3-octyne, diethyl 2-(2,4,6-triiodophenoxy)-1,3-propanedioate and diisopropyl 2-(2,4,6-triiodophenoxy)-1,3-propanedioate.

Claim 9

Dependent Claim 29 words

The x-ray contrast composition of claim 1 wherein said contrast agent is selected from the group consisting of: ethyl 2,2-bis-(3-iodophenoxy)acetate, ethyl-5-(2,4,6-triiodophenoxy)-hexanoate, 5-(2,4,6-triiodophenoxy)-hexan-1-ol, 10-(4-iodophenoxy)-undecan-1-ol, ethyl 5-(2,4,6-triiodophenoxy)-hexyl carbonate and ethyl 10-(3-iodophenoxy)-undecanoate.

Claim 10

Independent Claim 188 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 aqueous x-ray contrast composition comprising: an x-ray contrast agent, or a pharmaceutically acceptable salt thereof, having the formula ##STR40## wherein 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, 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≡C--Q; R 1 , R 2 , R 3 and R 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, said contrast agent being in the form of an aqueous dispersion in said composition wherein said dispersion contains from about 0.01 to about 15% w/v of at least one surfactant selected from the group consisting of cationic, anionic, nonionic and zwitterionic surfactants.

Claim 11

Independent Claim 188 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 aqueous x-ray contrast composition comprising: an x-ray contrast agent, or a pharmaceutically acceptable salt thereof, having the formula ##STR40## wherein 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, 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≡C--Q; R 1 , R 2 , R 3 and R 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, said contrast agent being in the form of an aqueous dispersion in said composition wherein said dispersion contains from about 0.01 to about 15% w/v of at least one surfactant selected from the group consisting of cationic, anionic, nonionic and zwitterionic surfactants.

Claim 12

Dependent Claim 27 words

The method of claim 9 wherein said contrast agent is selected from the group consisting of: 2-(4-Iodophenoxy)-decane, 2-(2,4,6-triiodophenoxy)-pentadecane, 2-(2,4,6-triiodophenoxy)decane, (2,4,6-triiodophenoxy)-1H, 1H, 2H, 2H - perfluorooctane and 1-(2,4,6-triiodo-3-trifluorophenoxy)octane.

Claim 13

Dependent Claim 20 words

The method of claim 9 wherein said contrast agent is selected from the group consisting of: 2-(2,4,6-triiodophenoxy)-nonane, 2-ethyl-1-(2,4,6-triiodophenoxy)-hexane and 3,3-diphenyl-1-(2,4,6-triiodophenoxy)propane.

Claim 14

Dependent Claim 22 words

The method of claim 9 wherein said contrast agent is selected from the group consisting of: 3-(2,4,6-triiodophenoxy)-nonane, 2-(4-iodophenoxy)-undecane, 2-iodophenoxycyclopentane, 3-iodophenoxycyclopentane and (3,5-dimethyl-2,4,6-triiodophenoxy)cyclopentane.

Claim 15

Dependent Claim 22 words

The method of claim 9 wherein said contrast agent is selected from the group consisting of: 2-(4-iodophenoxy)-pentadecane, 4-iodophenoxycyclopentane, 2,4,6-triiodophenoxycyclopentane, 2,4,6-triiodophenoxymethylcyclopentane and 2-(2,4,6-triiodophenoxy)ethylcyclopentane.

Claim 16

Dependent Claim 21 words

The method of claim 9 wherein said contrast agent is selected from the group consisting of: (E,E)-1-(2,4,6-triiodophenoxy)-3,7,11-trimethyl-2,6,10-dodecatriene, 1-(2,4,6-triiodophenoxy)-3,7-dimethyl-6-octene, (E)-1-(3,5-dimethyl-2,4,6-triiodophenoxy)-3,7-dimethyl-2,6-octadiene and (E)-1-(2,4,6-triiodophenoxy)-3,7-dimethyl-2,6-octadiene.

Claim 17

Dependent Claim 25 words

The method of claim 9 wherein said contrast agent is selected from the group consisting of: 1-(2,4,6-triiodophenoxy)-3-octyne, 2-(2,4,6- triiodophenoxy)-4-octyne, 1-(2,4,6-triiodophenoxy)-3-octyne, diethyl 2-(2,4,6-triiodophenoxy)-1,3-propanedioate and diisopropyl 2-(2,4,6-triiodophenoxy)-1,3-propanedioate.

Claim 18

Dependent Claim 27 words

The method of claim 9 wherein said contrast agent is selected from the group consisting of: ethyl 2,2-bis-(3-iodophenoxy)acetate, ethyl-5-(2,4,6-triiodophenoxy)-hexanoate, 5-(2,4,6-triiodophenoxy)-hexan-1-ol, 10-(4-iodophenoxy)-undecan-1-ol, ethyl 5-(2,4,6-triiodophenoxy)-hexyl carbonate and ethyl 10-(3-iodophenoxy)-undecanoate.

Claim 19

Dependent Claim 34 words

The method of claim 9 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 20

Dependent Claim 34 words

The method of claim 9 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 21

Dependent Claim 16 words

The method of claim 9 wherein said contrast agent is in the form of an emulsion.

Claim 22

Dependent Claim 13 words

The method of claim 9 wherein said cationic surfactant is cetyl trimethylammonium bromide.

Claim 23

Dependent Claim 31 words

The method 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 sulphosuccinates.

Claim 24

Dependent Claim 39 words

The method of claim 9 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.

Claim 25

Dependent Claim 15 words

The method of claim 9 wherein said X-ray contrast composition further comprises a suspending agent.

Claim 26

Dependent Claim 14 words

The method of claim 9 wherein said X-ray contrast composition further comprises a stabilizer.

Claim 27

Dependent Claim 14 words

The method of claim 9 wherein said X-ray contrast composition further comprises an antioxidant.

Claim 28

Dependent Claim 16 words

The method of claim 9 wherein said X-ray contrast composition further comprises an osmolality adjusting agent.

Claim 29

Dependent Claim 15 words

The method of claim 9 wherein said X-ray contrast composition further comprises a buffering agent.

Claim 30

Dependent Claim 16 words

The method of claim 9 wherein said X-ray contrast composition further comprises a pH adjusting agent.

Claim 31

Dependent Claim 15 words

The method of claim 9 wherein said X-ray contrast composition further comprises a flavoring agent.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1997-05-30	1997-11-29	1998-05-31	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	2001-05-30	2001-11-29	2002-05-31	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2005-05-30	2005-11-29	2006-05-31	$7700.00	Window Closed / Lapsed

Compositions of iodophenoxy alkanes and iodophenyl ethers for visualization of the gastrointestinal tract

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