Patents by Inventor Raymond E. Counsell
Raymond E. Counsell 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).
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Patent number: 7582279Abstract: A surface-modified lipoprotein-like oil-in-water emulsion useful as a blood-pool selective delivery vehicle for lipophilic imaging agents or lipophilic derivatives of water-soluble imaging agents. The blood-pool selective delivery vehicle remains in the blood for several hours, shows very little early hepatic sequestration, and is cleared from the blood within 24 hours. The mean diameter of the oil phase is less than 150 nm which minimizes sequestration by the reticuloendothelial system. The surface of the oil phase is modified with a polyethyl glycol-modified phospholipid to prevent normal interactions with the receptor sites of the hepatocytes.Type: GrantFiled: October 23, 2003Date of Patent: September 1, 2009Assignee: The Board of Regents of the University of MichiganInventors: Raymond E. Counsell, Marc A. Longino, Jamey P. Weichert
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Publication number: 20040258744Abstract: A surface-modified lipoprotein-like oil-in-water emulsion useful as a blood-pool selective delivery vehicle for lipophilic imaging agents or lipophilic derivatives of water-soluble imaging agents. The blood-pool selective delivery vehicle remains in the blood for several hours, shows very little early hepatic sequestration, and is cleared from the blood within 24 hours. The mean diameter of the oil phase is less than 150 nm which minimizes sequestration by the reticuloendothelial system. The surface of the oil phase is modified with a polyethyl glycol-modified phospholipid to prevent normal interactions with the receptor sites of the hepatocytes.Type: ApplicationFiled: October 23, 2003Publication date: December 23, 2004Inventors: Raymond E. Counsell, Marc A. Longino, Jamey P. Weichert
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Patent number: 6645463Abstract: A surface-modified lipoprotein-like oil-in-water emulsion useful as a blood-pool selective delivery vehicle for lipophilic imaging agents or lipophilic derivatives of water-soluble imaging agents. The blood-pool selective delivery vehicle remains in the blood for several hours, shows very little early hepatic sequestration, and is cleared from the blood within 24 hours. The mean diameter of the oil phase is less than 150 nm which minimizes sequestration by the reticuloendothelial system. The surface of the oil phase is modified with a polyethyl glycol-modified phospholipid to prevent normal interactions with the receptor sites of the hepatocytes.Type: GrantFiled: April 10, 1998Date of Patent: November 11, 2003Assignee: The Board of Regents of the University of MichiganInventors: Raymond E. Counsell, Marc A. Longino, Jamey P. Weichert
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Patent number: 6417384Abstract: The present invention provides improved radioiodinated phospholipid ether analogs which demonstrate significant tumor avidity and longer plasma half-life than shorter-chain analogs. The radioiodinated phospholipid ether analogs of the present invention provide superior imaging and visualization of neoplastic lesions and tumor-specific cytotoxic cancer therapy.Type: GrantFiled: July 3, 2001Date of Patent: July 9, 2002Assignee: The Regents of the University of MichiganInventors: Raymond E. Counsell, Marc A. Longino, Anatoly N. Pinchuk, Mark A. Rampy, Jamey P. Weichert
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Publication number: 20020065429Abstract: The present invention provides improved radioiodinated phospholipid ether analogs which demonstrate significant tumor avidity and longer plasma half-life than shorter-chain analogs. The radioiodinated phospholipid ether analogs of the present invention provide superior imaging and visualization of neoplastic lesions and tumor-specific cytotoxic cancer therapy.Type: ApplicationFiled: July 3, 2001Publication date: May 30, 2002Applicant: THE REGENTS OF THE UNIVERSITY OF MICHIGANInventors: Raymond E. Counsell, Marc A. Longino, Anatoly N. Pinchuk, Mark A. Rampy, Jamey P. Weichert
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Patent number: 6255519Abstract: Improved radioiodinated phospholipid ether analogs are described which exhibit significant tumor avidity and longer plasma half-life relative to shorter chain analogs. Use of these compounds results in superior imaging and visualization of neoplastic lesions and tumor-specific cytotoxic cancer therapy.Type: GrantFiled: September 20, 1999Date of Patent: July 3, 2001Assignee: Regents of the University of MichiganInventors: Raymond E. Counsell, Marc A. Longino, Anatoly N. Pinchuk, Mark A. Rampy, Jamey P. Weichert
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Patent number: 6126946Abstract: A heat and shelf-stable oil-in-water emulsion useful as a tissue or cell-selective delivery vehicle. Radioactive or stable, synthetic or semi-synthetic polyhalogenated triglycerides, such as 2-oleoylglycerol-1,3-bis[7-(3-amino-2,4,6-triiodophenyl)heptanoate] or 2-oleoylglycerol-1,3-bis[.omega.-(3,5-bis-trifluoromethyl)hepatanoate] or phenyl acetate, can be incorporated into the lipophilic core of a lipoprotein-like emulsion particle. The lipophilic core is surrounded by a phospholipid membrane comprising cholesterol and apolipoproteins. For hepatocyte-selective delivery, the emulsion is chylomicron remnant-like by being in a size range of 50 to 200 nm as measured by number weighting analysis with a narrow size distribution (<2% greater than 300 nm) and having a composition simulating naturally-occurring chylomicron remnants. Use of cholesterol in the emulsion formula facilitates association of apolipoproteins, especially Apo E which are recognized by liver cells and necessary for binding and uptake.Type: GrantFiled: July 23, 1997Date of Patent: October 3, 2000Assignee: University of Michigan, The Board of RegentsInventors: Raymond E. Counsell, Marc A. Longino, Jamey P. Weichert, Douglas A. Bakan
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Patent number: 6103216Abstract: A heat and shelf-stable oil-in-water emulsion useful as a tissue or cell-selective delivery vehicle. Radioactive or stable, synthetic or semi-synthetic polyhalogenated triglycerides, such as 2-oleoylglycerol-1,3-bis[7-(3-amino-2,4,6-triiodophenyl)heptanoate] or 2-oleoylglycerol-1,3-bis[.omega.-(3,5-bis-trifluoromethyl)-heptanoate] or phenyl acetate, can be incorporated into the lipophilic core of a lipoprotein-like emulsion particle. The lipophilic core is surrounded by a phospholipid membrane comprising cholesterol and apolipoproteins. For hepatocyte-selective delivery, the emulsion is chylomicron remnant-like by being in a size range of 50 to 200 nm as measured by number weighting analysis with a narrow size distribution (<2% greater than 300 nm) and having a composition simulating naturally-occurring chylomicron remnants. Use of cholesterol in the emulsion formula facilitates association of apolipoproteins, especially Apo E which are recognized by liver cells and necessary for binding and uptake.Type: GrantFiled: November 15, 1996Date of Patent: August 15, 2000Assignee: The Board of Regents acting for and on behalf of the University of MichiganInventors: Raymond E. Counsell, Marc A. Longino, Jamey P. Weichert, Douglas A. Bakan
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Patent number: 5985941Abstract: A heat and shelf-stable oil-in-water emulsion useful as a tissue or cell-selective delivery vehicle. Radioactive or stable, synthetic or semi-synthetic polyhalogenated triglycerides, such as 2-oleoylglycerol-1,3-bis[7-(3-amino-2,4,6-triiodophenyl)heptanoate] or 2-oleoylglycerol-1,3-bis[.omega.-(3,5-bis-trifluoromethyl)hepatanoate] or phenyl acetate, can be incorporated into the lipophilic core of a lipoprotein-like emulsion particle. The lipophilic core is surrounded by a phospholipid membrane comprising cholesterol and apolipoproteins. For hepatocyte-selective delivery, the emulsion is chylomicron remnant-like by being in a size range of 50 to 200 nm as measured by number weighting analysis with a narrow size distribution (<2% greater than 300 nm) and having a composition simulating naturally-occurring chylomicron remnants. Use of cholesterol in the emulsion formula facilitates association of apolipoproteins, especially Apo E which are recognized by liver cells and necessary for binding and uptake.Type: GrantFiled: June 30, 1995Date of Patent: November 16, 1999Assignee: University of MichiganInventors: Raymond E. Counsell, Marc A. Longino, Jamey P. Weichert, Douglas A. Bakan
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Patent number: 5851510Abstract: A heat and shelf-stable oil-in-water emulsion useful as a tissue or cell-selective delivery vehicle. Radioactive or stable, synthetic or semi-synthetic polyhalogenated triglycerides, such as 2-oleoylglycerol-1,3-bis?7-(3-amino-2,4,6-triiodophenyl)heptanoate! or 2-oleoylglycerol-1,3-bis?.omega.-(3,5-bis-trifluoromethyl)heptanoate! or phenyl acetate, can be incorporated into the lipophilic core of a lipoprotein-like emulsion particle. The lipophilic core is surrounded by a phospholipid membrane comprising cholesterol and apolipoproteins. For hepatocyte-selective delivery, the emulsion is chylomicron remnant-like by being in a size range of 50 to 200 nm as measured by number weighting analysis with a narrow size distribution (<2% greater than 300 nm) and having a composition simulating naturally-occurring chylomicron remnants. Use of cholesterol in the emulsion formula facilitates association of apolipoproteins, especially Apo E which are recognized by liver cells and necessary for binding and uptake.Type: GrantFiled: May 16, 1994Date of Patent: December 22, 1998Assignee: The Board of Regents of The University of MichiganInventors: Raymond E. Counsell, Marc A. Longino, Jamey P. Weichert, Douglas A. Bakan
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Patent number: 5795561Abstract: Novel radioiodinated analogues of naturally-occurring phospholipid ethers are tumor-specific and have a triglycerol backbone structure which, in certain embodiments, is substituted at the 3-position with an alkyl phosphocholine and include a monoiodinated benzoyl side chain substituted at the 2-position in accordance with the general formula: ##STR1## where n=1-15 ##STR2## M=0-15; Z=.sup.123 I, .sup.125 I, and .sup.131 I; Y=NH.sub.2, NR.sub.2, and NR.sub.3, and R=alkyl, aralkyl.Type: GrantFiled: September 12, 1994Date of Patent: August 18, 1998Assignee: The Board of Regents of the University of MichiganInventors: Raymond E. Counsell, Karen L. Meyer, Susan W. Schwendner, Terushi Haradahira
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Patent number: 5347030Abstract: Novel radioiodinated analogues of naturally-occurring phospholipid ethers are tumor-specific and have a triglycerol backbone structure which, in certain embodiments, is substituted at the 3-position with an alkyl phosphocholine and include a monoiodinated benzoyl side chain substituted at the 2-position in accordance with the general formula: ##STR1## where n= 1-15 ##STR2## m= 0-15; Z=.sup.123 I, .sup.125 I, and .sup.131 I; Y=NH.sub.2, NR.sub.2, and NR.sub.3, and R=alkyl, aralkyl.Type: GrantFiled: February 10, 1992Date of Patent: September 13, 1994Assignee: The Board of Regents of The University of MichiganInventors: Raymond E. Counsell, Karen L. Meyer, Susan W. Schwendner, Terushi Haradahira
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Patent number: 5093042Abstract: Novel iodinated arylaliphatic triglyceride analogs as radiologic agents are liver and hepatocyte site-specific. The triglyceride backbone structure is preferably 1,3-disubstituted or 1,2,3-trisubstituted with, in some embodiments, a 3-substituted-2,4,6-triiodophenyl aliphatic chain wherein the chain has a structure similar to naturally occurring fatty acids. In another embodiment, a monoiodophenyl aliphatic chain is utilized. Any position remaining on the triglyceride backbone is substituted with a saturated or unsaturated aliphatic hydrocarbon chain of the type found in naturally occurring fatty acids. The triglyceride analogs can be radioiodinated. In a preferred embodiment, a lipid emulsion is provided as the carrier vehicle.Type: GrantFiled: April 20, 1990Date of Patent: March 3, 1992Assignee: The University of MichiganInventors: Raymond E. Counsell, Marc A. Longino, Jamey P. Weichert, Susan P. Schwendner
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Patent number: 5087721Abstract: Novel radioiodinated analogues of naturally-occurring phospholipid ethers are tumor-specific and have a triglycerol backbone structure which is substituted at the 3-position with an alkyl phosphocholine and include a monoiodinated benzoyl side chain substituted at either the 1- or 2-position. In some embodiments of the invention, the monoiodinated aralkyl side chain may be substituted directly onto alkyl phosphocholine in accordance with general Formula: provided that one and only one of X or Y is a monoiodinated aralkyl ##STR1## where Y=NH.sub.2, NR.sub.2, NR.sub.3, NR.sub.2 R'R=alkyl, aralkylR'=a monoiodinated aralkyl, such as ##STR2## Z=.sup.122 I, .sup.123 I, .sup.125 I, and .sup.131 I n=1-15X=a monoiodinated aralkyl, like R', where n=1-15; or an alkyl, such as --CH.sub.2 --(CH).sub.m --CH.sub.3, where m=1-15.Type: GrantFiled: October 22, 1990Date of Patent: February 11, 1992Assignee: The University of MichiganInventors: Raymond E. Counsell, Karen L. Meyer, Susan W. Schwendner, Terushi Haradahira
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Patent number: 4965391Abstract: Novel radioiodinated analogues of naturally occurring phospholipid ethers are tumor-specific to enable selective visualization of neoplastic lesions by gamma-camera scintigraphy. The novel compounds enable a physician to differentiate neoplastic lesions from non-neoplastic lesions in a manner not heretofore available.Type: GrantFiled: October 23, 1987Date of Patent: October 23, 1990Assignee: The University of MichiganInventors: Raymond E. Counsell, Karen L. Meyer, Susan W. Schwendner
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Patent number: 4957729Abstract: Novel iodinated arylaliphatic triglyceride analogs as radiologic agents are liver and hepatocyte site-specific. The triglyceride backbone structure is preferably 1,3-disubstituted or 1,2,3-trisubstituted with, in some embodiments, a 3-substituted-2,4,6-triiodophenyl aliphatic chain wherein the chain has a structure similar to naturally occuring fatty acids. In another embodiment, a monoiodophenyl aliphatic chain is utilized. Any position remaining on the triglyceride backbone is substituted with a saturated or unsaturated aliphatic hydrocarbon chain of the type found in naturally occurring fatty acids. The triglyceride analogs can be radioiodinated. In a preferred embodiment, a lipid emulsion is provided as the carrier vehicle.Type: GrantFiled: May 30, 1989Date of Patent: September 18, 1990Assignee: The University of MichiganInventors: Raymond E. Counsell, Marc A. Longino, Jamey P. Weichert, Susan P. Schwendner
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Patent number: 4933157Abstract: Novel radioiodinated analogues of naturally-occurring cholestrol esters, arylaliphatic cholesteryl ethers, are selective for low density lipoproteins and have been shown to be successful imaging agents for adrenal glands. The arylaliphatic cholesteryl ethers have the general formula: ##STR1## where X is a radioactive isotope of iodine and n is an integer between 1 and 20. Two illustrative examples, m-iodobenzyl cholesteryl ether and 12-(m-iodophenyl) dodecyl cholesteryl ether, were radiolabeled with .sup.125 I by an isotope exchange reaction. Tissue distribution studies indicate significant accumulation of the cholesteryl ethers in the adrenal glands, and to a lesser extent in the liver. The cholesteryl ethers selectively incorporate into plasma lipoproteins as determined by polyacrylamide gel electrophoresis.Type: GrantFiled: June 27, 1988Date of Patent: June 12, 1990Assignee: The University of MichiganInventors: Raymond E. Counsell, Mohamed K. Ruyan, Susan W. Schwendner, Laura E. Deforge
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Patent number: 4925649Abstract: Novel iodinated and radioiodinated 1,2-diacylglycerol analogues are biological reagents for studying the effect of diacylglycerols in the activation of protein kinase C. This calcium-requiring enzyme may be involved in tumor promotion by phorbol diesters and related compounds. Iodinated and radioiodinated 1,2-diacylglycerol analogues, in accordance with the invention, are useful as imaging agents, such as radiopaques and radiopharmaceuticals, and have the general formula: ##STR1## The triglycerol backbone structure is 1,2-disubstituted with one position being occupied by an iodine-containing substituent, preferably an amino-substituted-2,4,6-triiodophenyl aliphatic chain, such as iopanoic acid, or by a monoiodiphenyl aliphatic chain, such as (m-iodophenyl)propanoic acid. The other position may be substituted with saturated and unsaturated long and short aliphatic chains.Type: GrantFiled: June 12, 1987Date of Patent: May 15, 1990Assignee: The University of MichiganInventors: Raymond E. Counsell, Laurie Strawn
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Patent number: 4883649Abstract: Iodinated clonidine derivatives useful, inter alia, as a probe for identification and characterization of .alpha..sub.2 -adrenergic receptor sites and as tracers for imaging techniques such as positron emission tomography or computer assisted tomography. Binding competition studies have indicated that p-iodoclonidine, for example, is a particularly efficacious binder for .alpha..sub.2 -adrenergic sites.Type: GrantFiled: October 13, 1988Date of Patent: November 28, 1989Assignee: The University of MichiganInventors: Raymond E. Counsell, Marcian Van Dort, Richard Neubig
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Patent number: 4873075Abstract: Novel iodinated arylaliphatic triglyceride analogs, as radiologic agents are liver and hepatocyte site-specific. The triglyceride backbone structure is preferably 1,3-disubstituted or 1,2,3-trisubstituted with, in some embodiments, a 3-substituted-2,4,6-triiodophenyl aliphatic chain wherein the chain has a structure similar to naturally occurring fatty acids. In another embodiment, a monoiodophenyl aliphatic chain is utilized. Any position remaining on the triglyceride backbone is substituted with a saturated or unsaturated aliphatic hydrocarbon chain of the type found in naturally occurring fatty acids. The triglyceride analogs can be radioiodinated. In a preferred embodiment, a lipid emulsion is provided as the carrier vehicle.Type: GrantFiled: September 10, 1985Date of Patent: October 10, 1989Assignee: The University of MichiganInventors: Raymond E. Counsell, Marc A. Longino, Jamey P. Weichert, Susan P. Schwendner