Patents by Inventor Carl R. Illig

Carl R. Illig has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 5525328
    Abstract: This invention relates to methods of x-ray diagnostic imaging the blood pool and/or lymph system of a mammal comprising administering a contrast effective amount of a particulate iodinated aroyloxy ester contrast agent having the structure: ##STR1## wherein n is an integer from 3 to 20; R.sup.1 is H, alkyl, fluoroalkyl, cycloalkyl, aryl, aralkyl, alkoxyalkyl or acetamidoalkyl;R.sup.2, R.sup.3 and R.sup.4 are independently H, alkyl, fluoroalkyl, alkoxy, aryloxy, halogen, hydroxy, acylamino, acetamidoalkyl, --COO-alkyl, --COO-aryl, --COO-aralkyl, cyano, sulfonyl, carboxamido or sulfonamido;R.sup.5 is H, alkyl, fluoroalkyl, halogen, hydroxy, acylamino, acetamidoalkyl, cyano, sulfonyl, carboxamido or sulfonamido;R.sup.6 and R.sup.7 are independently alkyl, cycloalkyl, aryl or aralkyl; andR.sup.8 and R.sup.9 are independently H or --COR.sup.6.
    Type: Grant
    Filed: June 24, 1994
    Date of Patent: June 11, 1996
    Assignee: NanoSystems L.L.C.
    Inventors: Edward R. Bacon, Carl R. Illig, Irennegbe K. Osifo, Thomas S. Caulfield
  • Patent number: 5525327
    Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising iodinated polymeric, water-insoluble beads having a particle size of from about 0.01 to about 1000.mu. wherein said iodinated polymeric beads comprise a polymer containing repeating units of the formula (I) ##STR1## wherein A is a repeating organic unit in the backbone chain of the polymer; and X is an organic moiety containing or iodinated eromatic group and a hydrophilic group, said moiety having an iodine content within the range of from about 40 to about 80 weight percent based or the molecular weight of X, in a pharmaceutically acceptable carrier comprising a cellulose derivative.
    Type: Grant
    Filed: April 14, 1994
    Date of Patent: June 11, 1996
    Assignee: Sterling Winthrop Inc.
    Inventors: Edward J. Baker, Robert W. Lee, Carl R. Illig, John L. Toner
  • Patent number: 5476644
    Abstract: The present invention provides compounds of the formula ##STR1## chelated with a paramagnetic metal ion wherein Z1 and Z2 each represent the atoms necessary to complete a monocyclic or polycyclic carbocyclic or heterocyclic ring system, said Z1 and Z2 independently optionally substituted with R.sup.6 and R.sup.7, respectively;R.sup.l, R.sup.2, R.sup.3 and R.sup.4 are independently carboxyalkyl (C.sub.1 -C.sub.2), --(CH.sub.2).sub.n --C(.dbd.O)--NH--R.sup.8, or --(CH.sub.2).sub.n --C(.dbd.O)--O--R.sup.8R.sup.5 is carboxyalkyl (C.sub.1 -C.sub.2);R.sup.6 and R.sup.7 are independently hydrogen, benzyl, or benzyloxy, said benzyl or benzyloxy optionally substituted with one, two or three substituents selected from the group consisting of amino, isocyanato (--N.dbd.C.dbd.O), isothiocyanato (--N.dbd.C.dbd.S), --NH--C(.dbd.O)--X or --NH--C(.dbd.S)--X;R.sup.8 is alkyl (C.sub.1 -C.sub.20), --(CH.sub.2).sub.m --Ar, or polyhydroxyalkyl (C.sub.1 -C.sub.
    Type: Grant
    Filed: April 13, 1994
    Date of Patent: December 19, 1995
    Assignee: Sterling Winthrop Inc.
    Inventors: Carl R. Illig, Thomas J. Caulfield, John L. Toner, Peng Guo, David L. Ladd
  • Patent number: 5472683
    Abstract: This invention relates to methods of x-ray diagnostic imaging the blood pool, liver, spleen, and/or lymph system of a mammal comprising administering a contrast effective amount of a mixed carbamic anhydride as a contrast agent having the structure ##STR1## X is H, NR.sup.1 R.sup.2 or CONR.sup.1 R.sup.3, R.sup.1 is H or alkylR.sup.2 is COR.sup.3R.sup.3 is H, alkyl or arylY is NR.sup.1 R.sup.2 or CONR.sup.1 R.sup.3 andN is NR.sup.1 R.sup.4 andR.sup.4 is H, alkyl, aryl or CH(R.sup.5)CO.sub.2 R.sup.1.This invention further relates to novel mixed carbamic anhydride contrast agents having the above structure to x-ray contrast compositions comprising such agents, and to methods of x-ray diagnostic imaging utilizing such agents.
    Type: Grant
    Filed: March 9, 1995
    Date of Patent: December 5, 1995
    Assignee: Eastman Kodak Company
    Inventor: Carl R. Illig
  • Patent number: 5468466
    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 ##STR2## 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, 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; andw=1-4in an aqueous pharmaceutically acceptable carrier.
    Type: Grant
    Filed: February 1, 1994
    Date of Patent: November 21, 1995
    Assignee: Sterling Winthrop, Inc.
    Inventors: Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig
  • Patent number: 5466435
    Abstract: Disclosed are contrast agents of the formula ##STR1## wherein Z is H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, alkoxycarbonyl, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R is C.sub.1 -C.sub.25 alkyl, cycloalkyl, ##STR2## or halo-lower-alkyl; each of which may be 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 H or lower-alkyl, optionally substituted with halo;x is 1-4;n is 1-4;m is 1-15;p is 1-20; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkyl;in an aqueous, pharmaceutically acceptable carrier comprising a cellulose derivative.
    Type: Grant
    Filed: April 4, 1994
    Date of Patent: November 14, 1995
    Assignee: Sterling Winthrop Inc.
    Inventors: Edward J. Baker, Edward R Bacon, Carl R. Illig, Thomas J. Caulfield, Brent D. Douty, Kurt A. Josef, John L. Toner, Robert W. Lee
  • Patent number: 5466715
    Abstract: Certain 3,4-disubstituted phenols and pharmaceutically acceptable salts thereof are provided which mimic IL-1 activity by inducing IL-2 synthesis and subsequent IL-2 receptor expression. Specifically, the invention provides compounds of Formula I and acid addition salts thereof: ##STR1## wherein Y is ##STR2## NHSO.sub.2 or SO.sub.2 NH where R.sup.4 is H; Z is --O--, --NH--, --NR--, --S--, or other heteroatoms capable of hydrogen bonding with R.sup.4 to give a preferred conformation;R is alkyl;R.sup.1 is --OH;R.sup.2 is H, alkyl, cycloalkyl, aralkyl, substituted or unsubstituted aryl, or a substituted or unsubstituted nitrogen heterocyclic group having 4 to 5 nuclear carbon atoms; andR.sup.3 is a lipophilic moiety selected from the group consisting of substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.16 cycloalkyl and 2,4-di-t-pentylphenyl.
    Type: Grant
    Filed: March 8, 1994
    Date of Patent: November 14, 1995
    Assignee: Sterling Winthrop Inc.
    Inventors: William N. Washburn, Barbara B. Lussier, Carl R. Illig, Lee H. Latimer
  • Patent number: 5449691
    Abstract: A method for inducing the production of interleukin 2 in a warm blooded animal by administering an effective amount of a compound of the formula (I) ##STR1## wherein Y is ##STR2## NHSO.sub.2 or SO.sub.2 NH where R.sup.4 is H; Z is --O--, --NH--, --NR--, --S--, or other heteroatoms capable of hydrogen bonding with R.sup.4 to give a preferred conformation;R is alkyl;R.sup.1 is --NH.sub.2 or --NHCH.sub.3 ;R.sup.2 is H, alkyl, cycloalkyl, aralkyl, substituted or unsubstituted aryl, or a substituted or unsubstituted nitrogen heterocyclic group having 4 to 5 nuclear carbon atoms; andR.sup.3 is a lipophilic moiety.
    Type: Grant
    Filed: June 24, 1993
    Date of Patent: September 12, 1995
    Assignee: Sterling Winthrop Inc.
    Inventors: William N. Washburn, Lee H. Latimer, Barbara B. Lussier, Carl R. Illig, Alexander L. Weis
  • Patent number: 5443814
    Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a nonionic x-ray producing agent in combination with a cellulose derivative in a pharmaceutically acceptable carrier; and methods for their use in diagnostic radiology of the gastrointestinal tract.
    Type: Grant
    Filed: March 4, 1994
    Date of Patent: August 22, 1995
    Assignee: Sterling Winthrop, Inc.
    Inventors: Carl R. Illig, John L. Toner, Robert W. Lee, Edward J. Baker
  • Patent number: 5422114
    Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising an x-ray producing agent of the formula or a pharmaceutically acceptable salt thereof ##STR1## and methods for their use in diagnostic radiology of the gastrointestinal tract, whereinZ is 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.sub.1 and R.sub.2 are independently H, C.sub.1 -C.sub.25 alkyl, cycloalkyl, acetyl or halo-lower-alkyl, wherein said C.sub.1 -C.sub.
    Type: Grant
    Filed: February 25, 1994
    Date of Patent: June 6, 1995
    Assignee: Sterling Winthrop Inc.
    Inventors: Carl R. Illig, Thomas J. Caulfield, Robert W. Lee, Edward J. Baker
  • Patent number: 5405600
    Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a polymeric material capable of forming a coating on the gastrointestinal tract and a nonionic x-ray producing agent in a pharmaceutically acceptable carrier; and methods for their use in diagnostic radiology of the gastrointestinal tract.
    Type: Grant
    Filed: August 11, 1993
    Date of Patent: April 11, 1995
    Assignee: Sterling Winthrop Inc.
    Inventors: Carl R. Illig, John L. Toner
  • Patent number: 5385722
    Abstract: Disclosed are contrast agents of the formula ##STR1## wherein ##STR2## Z is H, halo, C.sub.5 -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 is C.sub.1 -C.sub.25 alkyl, cycloalkyl, aryl or halo-lower-alkyl, 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; andw is 1-4;in a pharmaceutically acceptable carrier comprising a cellulose derivative.
    Type: Grant
    Filed: April 18, 1994
    Date of Patent: January 31, 1995
    Assignee: Sterling Winthrop Inc.
    Inventors: Edward J. Baker, Robert W. Lee, Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig, John L. Toner
  • Patent number: 5385721
    Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising an x-ray producing agent of the formula or a pharmaceutically acceptable salt thereof ##STR1## wherein R is methyl, ethyl, n-propyl, C.sub.4 -C.sub.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.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 H, lower-alkyl, optionally substituted with halo;n is 2-5;m is 2-5;p is 1-10; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkyl;in a pharmaceutically acceptable carrier comprising a cellulose derivative.
    Type: Grant
    Filed: March 22, 1994
    Date of Patent: January 31, 1995
    Assignee: Sterling Winthrop Inc.
    Inventors: Edward J. Baker, Kurt A. Josef, Edward R. Bacon, Kimberly G. Estep, Carl R. Illig, Brent D. Douty, John L. Toner, Robert W. Lee
  • Patent number: 5385720
    Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising an x-ray producing agent of the formula or a pharmaceutically acceptable salt thereof ##STR1## wherein Z is 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 is C.sub.1 -C.sub.25 alkyl, cycloalkyl, or halo-lower-alkyl, each of which may be 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.dbd.C--Q;R.sub.1, R.sub.2, R.sub.3 and R.sub.
    Type: Grant
    Filed: March 23, 1994
    Date of Patent: January 31, 1995
    Assignee: Sterling Winthrop Inc.
    Inventors: Edward J. Baker, Robert W. Lee, Carl R. Illig, Brent D. Douty, John L. Toner
  • Patent number: 5384107
    Abstract: Compounds having the structure ##STR1## wherein (Z--COO is the residue of an iodinated aromatic acid; n is an integer from 0 to 6;R.sup.1 and R.sup.2 are independently H, alkyl, fluoroalkyl, cycloalkyl, aryl, aralkyl, alkoxy or aryloxy;R.sup.3 and R.sup.4 are independently H, alkyl, fluoroalkyl, cycloalkyl, aryl, aralkyl, alkoxy, aryloxy, halogen, hydroxy or acylamino;Q represents the atoms necessary to complete a carbocyclic or heterocyclic unsaturated mono- or bicyclic aromatic ring; andR.sup.5 is H, alkyl, cycloalkyl, aryl, aralkyl, alkoxy, aryloxy, halogen, hydroxy, amino, acylamino, alkoxyalkyl, fluoroalkyl, acetamidoalkyl, COO-alkyl, cyano, carboxamido, sulfonate, sulfonamido, ureido, or carbamyl are useful as contrast agents in x-ray imaging compositions and methods.
    Type: Grant
    Filed: August 3, 1994
    Date of Patent: January 24, 1995
    Assignee: Sterling Winthrop Inc.
    Inventors: Baldev Singh, Edward R. Bacon, Carl R. Illig
  • Patent number: 5372800
    Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a polymeric material capable of forming a coating on the gastrointestinal tract and an x-ray producing agent of the formula ##STR1## and methods for their use in diagnostic radiology of the gastrointestinal tract whereinX= ##STR2## 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, 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 or lower-alkoxy-carbonyloxy,n is 1-5;y is 0-4; andw is 1-4.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: December 13, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig
  • Patent number: 5368837
    Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a crystalline contrast agent in a pharmaceutically acceptable carrier comprising a cellulose derivative; and methods for their use in diagnostic radiology of the gastrointestinal tract.
    Type: Grant
    Filed: April 14, 1994
    Date of Patent: November 29, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: Edward J. Baker, Robert W. Lee, Eugene R. Cooper, John L. Toner, Carl R. Illig
  • Patent number: 5360604
    Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a crystalline organic constrast agent in combination with a pharmaceutically acceptable clay in a pharmaceutically acceptable carrier; and methods for their use in diagnostic radiology of the gastrointestinal tract.
    Type: Grant
    Filed: May 23, 1994
    Date of Patent: November 1, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: Stephen B. Ruddy, Mary E. Roberts, Gregory L. McIntire, Eugene R. Cooper, Carl R. Illig
  • Patent number: 5348727
    Abstract: A compound of the formula: ##STR1## wherein Z.dbd.H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, alkoxycarbonyl, cyano, wherein thealkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R.dbd.C.sub.1 -C.sub.25 alkyl, cycloalkyl, ##STR2## or halo-lower-alkyl; each of which may be 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 H, or lower-alkyl, optionally substituted with halo;x is 1-4;n is [1-5]1-4;m is 1-15;p is 1-20; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, these compounds are useful as X-ray contrast agents or aryl-lower alkyl.
    Type: Grant
    Filed: March 11, 1993
    Date of Patent: September 20, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: Edward R. Bacon, Carl R. Illig, Thomas J. Caulfield, Brent D. Douty, Kurt A. Josef
  • Patent number: 5344638
    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 whereinwhereinZ=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 1-3y is 1-4;n is 1-5;m is 1-15;p is 1-10; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkylin an aqueous, pharmaceutically acceptable carrier.
    Type: Grant
    Filed: March 11, 1993
    Date of Patent: September 6, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: Carl R. Illig, Brent D. Douty