Patents by Inventor Chyng-Yann Shiue

Chyng-Yann Shiue 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: 10507250
    Abstract: Method provided for labeling a nuclear medicine for imaging tracing, comprising a labeling precursor of the HDAC inhibitor BNL-26 (C22H23N3O) and the derivatives that are separated into two classes. The first class comprises a BNL-26 (C22H23N3O) and derivatives BNL-26a (C21H21N3O), BNL-26b (C22H22N2O), and other compounds of the labeling precursors which are categorized into two parts, the first part includes BNL-26-CH2CH2OTs (C31H33N3O4S), BNL-26a-CH2CH2OTs (C30H31N3O4S), and BNL-26b-CH2CH2OTs (C31H32N2O4S), which provides labeling precursor through —CH2CH2OTs structure, and the second part includes pre-BNL-26 (C28H34N3O3B), pre-BNL-26a (C27H32N3O3B), pre-BNL-26b (C28H33N2O3B), which provides labeling precursor through 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl structure. The second class includes BNL-26 (C22H23N3O) indole/indoline, which provides a series of derivative labeling precursors derived from a secondary amide bond.
    Type: Grant
    Filed: September 8, 2017
    Date of Patent: December 17, 2019
    Assignee: Institute of Nuclear Energy Research, Atomic Energy Council, Executive Yuan
    Inventors: Ming-Hsin Li, Chyng-Yann Shiue, Han-Chih Chang, Chun-Fang Feng
  • Publication number: 20190076552
    Abstract: Method provided for labeling a nuclear medicine for imaging tracing, comprising a labeling precursor of the HDAC inhibitor BNL-26 (C22H23N3O) and the derivatives that are separated into two classes. The first class comprises a BNL-26 (C22H23N3O) and derivatives BNL-26a (C21H21N3O), BNL-26b (C22H22N2O), and other compounds of the labeling precursors which are categorized into two parts, the first part includes BNL-26-CH2CH2OTs (C31H33N3O4S), BNL-26a-CH2CH2OTs (C30H31N3O4S), and BNL-26b-CH2CH2OTs (C31H32N2O4S), which provides labeling precursor through —CH2CH2OTs structure, and the second part includes pre-BNL-26 (C28H34N3O3B), pre-BNL-26a (C27H32N3O3B), pre-BNL-26b (C28H33N2O3B), which provides labeling precursor through 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl structure. The second class includes BNL-26 (C22H23N3O) indole/indoline, which provides a series of derivative labeling precursors derived from a secondary amide bond.
    Type: Application
    Filed: September 8, 2017
    Publication date: March 14, 2019
    Inventors: Ming-Hsin Li, Chyng-Yann Shiue, Han-Chih Chang, Chun-Fang Feng
  • Patent number: 10059661
    Abstract: A [F-18]FEONM precursor is synthesized. 2-bromoethanol is added to further connect an atom of oxygen at an N terminal of the precursor. Four atoms of carbon can be further connected. Thus, better fat-solubility is obtained along with the increase in carbon. Positioning in brain imaging becomes better.
    Type: Grant
    Filed: July 28, 2017
    Date of Patent: August 28, 2018
    Assignee: INTITUTE OF NUCLEAR ENERGY RESEARCH, ATOMIC ENERGY COUNCIL, Executive Yuan, R.O.C.
    Inventors: Shu-Hung Lin, Sheng-Po Huang, Show-Wen Liu, Cheng-Fang Hsu, Jenn-Tzong Chen, Shiou-Shiow Farn, Wuu-Jyh Lin, Chyng-Yann Shiue
  • Patent number: 10005727
    Abstract: The present invention relates to a group of compounds for nuclear medicine imaging through F-18 labeled histone acetylation inhibitors (HDACi) of indole or indoline benzoyl amine and its derivatives, and provides a series of nuclear medicine imaging agents that bind with HDAC overexpression in vivo for diagnosis of malignant tumors discovered in the nuclear medicine imaging tracing.
    Type: Grant
    Filed: October 6, 2016
    Date of Patent: June 26, 2018
    Assignee: INSTITUTE OF NUCLEAR ENERGY RESEARCH ATOMIC ENERGY COUNCIL EXECUTIVE YUAN
    Inventors: Ming-Hsin Li, Chyng-Yann Shiue, Han-Chih Chang, Chun-Fang Feng
  • Publication number: 20180099933
    Abstract: The present invention relates to a group of compounds for nuclear medicine imaging through F-18 labeled histone acetylation inhibitors (HDACi) of indole or indoline benzoyl amine and its derivatives, and provides a series of nuclear medicine imaging agents that bind with HDAC overexpression in vivo for diagnosis of malignant tumors discovered in the nuclear medicine imaging tracing.
    Type: Application
    Filed: October 6, 2016
    Publication date: April 12, 2018
    Inventors: MING-HSIN LI, Chyng-Yann Shiue, Han-Chih Chang, Chun-Fang Feng
  • Patent number: 9789207
    Abstract: A PET imaging agent is made, by at first, washing out fluoride ions (F-18) adhered on an ion exchange resin to a reaction vessel with potassium carbonate/Kryptofix 2.2.2 in acetonitrile-water. After processing the first azeotropic distillation with helium while water is removed, the temperature is cooled down. Then, acetonitrile is added to the reaction vessel to be heated up. After processing the second azeotropic distillation with helium while water is removed, the temperature is cooled down and excess water is extracted. A precursor is then added to the reaction vessel to be heated up for processing a fluorination reaction. The reaction mixture obtained after the fluorination reaction is cooled down to be flown through a solid-phase extraction column with waste drained into a waste tank. Then, ethanol is used to wash out a product, i.e. [F-18]FEONM, adsorbed by the column, to be collected in a collection vial.
    Type: Grant
    Filed: June 16, 2016
    Date of Patent: October 17, 2017
    Assignee: INSTITUTE OF NUCLEAR ENERGY RESEARCH, ATOMIC ENERGY COUNCIL, Executive Yuan, R.O.C.
    Inventors: Li-Yuan Huang, Yean-Hung Tu, Jenn-Tzong Chen, Chyng-Yann Shiue
  • Patent number: 9603950
    Abstract: A method of synthesizing a compound of imaging agent with HDAC (histone deacetylase) inhibitor consists of two parts, the first part of the method is to provide the inhibitor of HDAC with a compound of imaging agent that includes HDAC inhibitor BNL-26 (C22H23N3O) and its analogs to be labeled with radionuclide F-18, producing a series of new nuclear medicine tracers: BNL-26-CH2CH218F, BNL-26a-CH2CH218FF, BNL-26b-CH2CH218F, BNL-26c-CH2CH218F and BNL-26d-CH2CH218F. These nuclear medicine with imaging agents can be used as a tracer in vivo binding to over-expression HDAC and produce a HDAC nuclear medicine imaging effect to serve for clinical diagnosis. The second part of the method is to provide a slightly adjusted a structural framework of BNL-26 and use pyridine to substitute the benzene ring of the BNL-26 structure, and then synthesize with other substituent to produce a series of additional 30 more HDAC inhibitors, named from Iner-1 to Iner-30 compounds.
    Type: Grant
    Filed: October 25, 2015
    Date of Patent: March 28, 2017
    Assignee: INSTITUTE OF NUCLEAR ENERGY RESEARCH
    Inventors: Ming-Hsin Li, Chyng-Yann Shiue, Han-Chih Chang, Han-Hsiang Chu
  • Patent number: 9186423
    Abstract: A radiocontrast agent for tau protein is provided. The agent is selectively and strongly bound to tau protein and its tangle found in brain diseases like Alzheimer's disease (AD). The agent is especially suitable to be used in PET imaging for brain diseases. Or, the agent can be used to inhibit tau protein overexpressive and, thus, stop the proceeding of brain disease.
    Type: Grant
    Filed: September 22, 2014
    Date of Patent: November 17, 2015
    Assignee: INSTITUTE OF NUCLEAR ENERGY RESEARCH, ATOMIC ENERGY COUNCIL, Executive Yuan, R.O.C.
    Inventors: Wuu-Jyh Lin, Shiou-Shiow Farn, Yean-Hung Tu, Li-Yuan Huang, Dow-Che Chen, Kuo-Yuan Chu, Mao-Hsung Chang, Ting-Shien Duh, Jenn-Tzong Chen, Chyng-Yann Shiue
  • Patent number: 7041851
    Abstract: This invention relates to novel fluorinated phenyl thiphenyl (also named diarylsulfide) derivatives and their use in Positron Emission Tomagraphy (PET) imaging of Serotonin Transporters (SERTS). The present invention also provides diagnostic compositions comprising the novel compounds of the present invention, and a pharmaceutically acceptable carrier or diluent. The invention further provides a method of imaging SERTS, comprising introducing into a patient a detectable quantity of a labeled compound of the present invetion, or a pharmaceutically acceptable salt, ester, amide or prodrug thereof.
    Type: Grant
    Filed: March 14, 2003
    Date of Patent: May 9, 2006
    Assignee: The Trustees of the University of Pennsylvania
    Inventors: Hank F. Kung, Chyng-Yann Shiue, Shunichi Oya, Seok Rye Choi, Grace G. Shiue, Ping Fang
  • Patent number: 6864393
    Abstract: This invention relates to novel fluorinated phenyl thiphenyl (also named diarylsulfide) derivatives and their use in Positron Emission Tomagraphy (PET) imaging of Serotonin Transporters (SERTS). The present invention also provides diagnostic compositions comprising the novel compounds of the present invention, and a pharmaceutically acceptable carrier or diluent. The invention further provides a method of imaging SERTS, comprising introducing into a patient a detectable quantity of a labeled compound of the present invetion, or a pharmaceutically acceptable salt, ester, amide or prodrug thereof.
    Type: Grant
    Filed: March 14, 2003
    Date of Patent: March 8, 2005
    Assignee: The Trustees of the University of Pennsylvania
    Inventors: Hank F. Kung, Chyng-Yann Shiue, Shunichi Oya, Seok Rye Choi, Grace G. Shiue, Ping Fang
  • Patent number: 6855828
    Abstract: Nitroaromatic compounds and immunogenic conjugates comprising a novel nitroaromatic compound and a carrier protein are disclosed. The invention further presents monoclonal antibodies highly specific for the claimed nitroaromatic compounds, the compounds' protein conjugates, the compounds' reductive byproducts, and adducts formed between the compounds and mammalian hypoxic cell tissue proteins. The invention is further directed to methods for detecting tissue hypoxia using immunohistological techniques, non-invasive nuclear medicinal methods, or nuclear magnetic resonance. Diagnostic kits useful in practicing the methods of claimed invention are also provided.
    Type: Grant
    Filed: August 25, 2000
    Date of Patent: February 15, 2005
    Assignee: The Trustees of the University of Pennsylvania
    Inventors: Cameron J. Koch, Alexander V. Kachur, Sydney M. Evans, Chyng-Yann Shiue, Ian R. Baird, Kirsten A. Skov, William R. Dolbier, Jr., An-Rong Li, Brian R. James
  • Publication number: 20050026974
    Abstract: Novel nitroaromatic compounds and immunogenic conjugates comprising a novel nitroaromatic compound and a carrier protein are disclosed. The invention further presents monoclonal antibodies highly specific for the claimed nitroaromatic compounds, the compounds' protein conjugates, the compounds' reductive byproducts, and adducts formed between the compounds and mammalian hypoxic cell tissue proteins. The invention is further directed to methods for detecting tissue hypoxia using immunohistological techniques, non-invasive nuclear medicinal methods, or nuclear magnetic resonance. Diagnostic kits useful in practicing the methods of claimed invention are also provided.
    Type: Application
    Filed: August 27, 2004
    Publication date: February 3, 2005
    Inventors: Cameron Koch, Alexander Kachur, Sydney Evans, Chyng-Yann Shiue, Ian Baird, Kirsten Skov, William Dolbier, An-Rong Li, Brian James
  • Publication number: 20030236234
    Abstract: This invention relates to novel fluorinated phenyl thiphenyl (also named diarylsulfide) derivatives and their use in Positron Emission Tomagraphy (PET) imaging of Serotonin Transporters (SERTS). The present invention also provides diagnostic compositions comprising the novel compounds of the present invention, and a pharmaceutically acceptable carrier or diluent. The invention further provides a method of imaging SERTS, comprising introducing into a patient a detectable quantity of a labeled compound of the present invetion, or a pharmaceutically acceptable salt, ester, amide or prodrug thereof.
    Type: Application
    Filed: March 14, 2003
    Publication date: December 25, 2003
    Inventors: Hank F. Kung, Chyng-Yann Shiue, Shunichi Oya, Seok Rye Choi, Grace G. Shiue, Ping Fang
  • Patent number: 6252087
    Abstract: Nitroaromatic compounds and immunogenic conjugates comprising a novel nitroaromatic compound and a carrier protein are disclosed. The invention further presents monoclonal antibodies highly specific for the claimed nitroaromatic compounds, the compounds' protein conjugates, the compounds' reductive byproducts, and adducts formed between the compounds and mammalian hypoxic cell tissue proteins. The invention is further directed to methods for detecting tissue hypoxia using immunohistological techniques, non-invasive nuclear medicinal methods, or nuclear magnetic resonance. Diagnostic kits useful in practicing the methods of claimed invention are also provided.
    Type: Grant
    Filed: July 28, 1998
    Date of Patent: June 26, 2001
    Assignee: The Trustees of the University of Pennsylvania
    Inventors: Cameron J. Koch, Alexander V. Kachur, Sydney M. Evans, Chyng-Yann Shiue, Ian R. Baird, Kirsten A. Skov, William R. Dolbier, Jr., An-Rong Li, Brian R. James
  • Patent number: 4871527
    Abstract: There is disclosed radioligands labeled with the position emitting radionuclide [.sup.18 F] suitable for dynamic study in living humans with position emission transaxial tomography. These new [.sup.18 F]-N-fluoroalkylspiroperidols, wherein the alkyl group contains from 2-6 carbon atoms, exhibit extremely high affinity for the dopamine receptors and provide enhanced uptake and retention in the brain concomitant with reduced radiation burden. These characteristics all combine to make these new radioligands useful for mapping dopamine receptors in normal and disease states in the living brain. Additionally, a new synthetic procedure for these radioligands as well as a new procedure for preparing the radiolabeled alkyl halide alkylating reagents are also disclosed.
    Type: Grant
    Filed: April 29, 1987
    Date of Patent: October 3, 1989
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Chyng-Yann Shiue, Alfred P. Wolf, Lan-Qin Bai, Ren-Tui Teng
  • Patent number: 4617386
    Abstract: Process for the production of 2-deoxy-2-fluoro-D-glucose and the corresponding .sup.18 F-compound in which methyl 4,6-O-benzylidine-3-O-methyl-2-O-trifluoromethanesulfonyl-.beta.-D-mannopy ranoside is reacted with a triflating reagent, the resulting compound reacted with CsHF.sub.2, RbF or the corresponding .sup.18 F-compounds, and thereafter the alkyl groups removed by hydrolysis.
    Type: Grant
    Filed: April 25, 1983
    Date of Patent: October 14, 1986
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: David R. Elmaleh, Shlomo Levy, Chyng-Yann Shiue, Alfred P. Wolf
  • Patent number: 4439414
    Abstract: The novel compounds 1-.sup.11 C-D-glucose, 1-.sup.11 C-D-mannose, 1-.sup.11 C-D-galactose, 2-.sup.11 C-D-glucose, 2-.sup.11 C-D-mannose and 2-.sup.11 C-D-galactose which can be used in nuclear medicine to monitor the metabolism of glucose and galactose can be rapidly prepared by reaction of the appropriate aldose substrate with an alkali metal .sup.11 C-labeled cyanide followed by reduction with a Raney alloy in formic acid.
    Type: Grant
    Filed: January 26, 1982
    Date of Patent: March 27, 1984
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Chyng-Yann Shiue, Alfred P. Wolf
  • Patent number: 4436717
    Abstract: The novel radioactive compound .sup.18 F-4-fluoroantipyrine having high specific activity which can be used in nuclear medicine in diagnostic applications, prepared by the direct fluorination of antipyrine in acetic acid with radioactive fluorine at room temperature and purifying said radioactive compound by means of gel chromatography with ethyl acetate as eluent is disclosed. The non-radioactive 4-fluoroantipyrine can also be prepared by the direct fluorination of antipyrine in acetic acid with molecular fluorine at room temperature and purified by means of gel chromotography with ethyl acetate eluent.
    Type: Grant
    Filed: May 29, 1981
    Date of Patent: March 13, 1984
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Chyng-Yann Shiue, Alfred P. Wolf
  • Patent number: H74
    Abstract: Process for the production of 2-deoxy-2-fluoro-D-glucose and the corresponding .sup.18 F-compound by the reaction of acetyl hypofluorite or the corresponding .sup.18 F-compound with 3,4,6-tri-O-acetyl-D-glucal followed by hydrolysis. Process includes the production of the hypofluorite compound at ambient temperature.
    Type: Grant
    Filed: February 24, 1983
    Date of Patent: June 3, 1986
    Assignee: The United States of America as represented by The United States Department of Energy
    Inventors: Chyng-Yann Shiue, Piero A. Salvadori, Alfred P. Wolf, Joanna S. Fowler, Robert R. MacGregor
  • Patent number: H1209
    Abstract: There is disclosed a radioligand labeled with a positron emitting radionuclide suitable for dynamic study in living humans with positron emission transaxial tomography. [.sup.18 F]-N-methylspiroperidol, exhibiting extremely high affinity for the dopamine receptors, provides enhanced uptake and retention in the brain concomitant with reduced radiation burden. These characteristics all combine to provide [.sup.18 F]-N-methylspiroperidol as a radioligand superior to known radioligands for mapping dopamine receptors in normal and disease states in the living brain. Additionally, a new synthetic procedure for this material is disclosed.
    Type: Grant
    Filed: October 4, 1985
    Date of Patent: July 6, 1993
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Chyng-Yann Shiue, Joanna S. Fowler, Alfred P. Wolf