Radio-methyl vorozole and methods for making and using the same

Kim, Sung Won; Biegon, Anat; Fowler, Joanna S.

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Title: Radio-methyl vorozole and methods for making and using the same

Abstract

Radiotracer vorozole compounds for in vivo and in vitro assaying, studying and imaging cytochrome P450 aromatase enzymes in humans, animals, and tissues and methods for making and using the same are provided. [N-radio-methyl] vorozole substantially separated from an N-3 radio-methyl isomer of vorozole is provided. Separation is accomplished through use of chromatography resins providing multiple mechanisms of selectivity.

Inventors:: Kim, Sung Won; Biegon, Anat; Fowler, Joanna S.

Issue Date:: Tue Aug 05 00:00:00 EDT 2014

Research Org.:: Brookhaven National Laboratory (BNL), Upton, NY (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1150009

Patent Number(s):: 8795629

Application Number:: 12/704,114

Assignee:: Brookhaven Science Associates, LLC (Upton, NY)

Patent Classifications (CPCs):: A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61K - PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07B - GENERAL METHODS OF ORGANIC CHEMISTRY

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A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61K - PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
A61K51/0453 - {having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole}

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07B - GENERAL METHODS OF ORGANIC CHEMISTRY
C07B2200/05 - Isotopically modified compounds, e.g. labelled

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
C07D403/06 - linked by a carbon chain containing only aliphatic carbon atoms
C07D403/10 - linked by a carbon chain containing aromatic rings

G - PHYSICS G01 - MEASURING G01N - INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
G01N2333/90245 - acting on paired donors with incorporation of molecular oxygen
G01N2800/52 - Predicting or monitoring the response to treatment
G01N33/573 - for enzymes or isoenzymes

Show less

DOE Contract Number:: AC02-98CH10886

Resource Type:: Patent

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Kim, Sung Won, Biegon, Anat, and Fowler, Joanna S. Radio-methyl vorozole and methods for making and using the same.  United States: N. p., 2014. 
        Web.

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                    Kim, Sung Won, Biegon, Anat, & Fowler, Joanna S. Radio-methyl vorozole and methods for making and using the same.  United States.

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                    Kim, Sung Won, Biegon, Anat, and Fowler, Joanna S. Tue .  
        "Radio-methyl vorozole and methods for making and using the same".  United States.  https://www.osti.gov/servlets/purl/1150009.

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@article{osti_1150009,

  title        = {Radio-methyl vorozole and methods for making and using the same},

  author       = {Kim, Sung Won and Biegon, Anat and Fowler, Joanna S.},

  abstractNote = {Radiotracer vorozole compounds for in vivo and in vitro assaying, studying and imaging cytochrome P450 aromatase enzymes in humans, animals, and tissues and methods for making and using the same are provided. [N-radio-methyl] vorozole substantially separated from an N-3 radio-methyl isomer of vorozole is provided. Separation is accomplished through use of chromatography resins providing multiple mechanisms of selectivity.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {Tue Aug 05 00:00:00 EDT 2014},

  month        = {Tue Aug 05 00:00:00 EDT 2014}

}

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Works referenced in this record:

(1H-azol-1-ylmethyl) substituted benzotriazole derivatives and pharmaceutical compositions containing them
patent, July 1990

Raeymaekers, Alfons H. M.; Freyne, Eddy Jean Edgard; Van Gelder, Josephu L. H.
US Patent Document 4,943,574
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Process for preparing enantiomerically pure 6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl) methyl]-1-methyl-1H-benzotrizole
patent, September 1997

Willemsens, Albert Louis Anna; Verstappen, Walter Louis Antoine; Copmans, Alex Herman
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Preparation and comparison of a pentafluorophenyl stationary phase for reversed-phase liquid chromatography
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Csató, Edit; Fülöp, Nándor; Szabó, Gyula
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Chromatographic classification and comparison of commercially available reversed-phase liquid chromatographic columns containing phenyl moieties using principal component analysis
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Euerby, Melvin R.; Petersson, Patrik; Campbell, William
Journal of Chromatography A, Vol. 1154, Issue 1-2, p. 138-151
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Distribution of Aromatase Cytochrome P450 Messenger Ribonucleic Acid in Adult Rhesus Monkey Brains1
journal, October 1997

Abdelgadir, Salah E.; Roselli, Charles E.; Choate, Jerome V. A.
Biology of Reproduction, Vol. 57, Issue 4
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Unique distribution of aromatase in the human brain: In vivo studies with PET and [N-methyl-11C]vorozole
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Biegon, Anat; Kim, Sung Won; Alexoff, David L.
Synapse, Vol. 64, Issue 11
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Development Summary towards a Manufacturable Process for R 83842 [( S )-6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole] ^†
journal, May 2000

De Knaep, A. G. M.; Vandendriessche, A. M. J.; Daemen, D. J. E.
Organic Process Research & Development, Vol. 4, Issue 3
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Comparative evaluation of positron emission tomography radiotracers for imaging the norepinephrine transporter: (S,S) and (R,R) enantiomers of reboxetine analogs ([11C]methylreboxetine, 3-Cl-[11C]methylreboxetine and [18F]fluororeboxetine), (R)-[11C]nisox: Norepinephrine transporter radiotracers for PET
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Ding, Yu-Shin; Lin, Kuo-Shyan; Logan, Jean
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Synthesis and PET studies of [¹¹C-cyano]letrozole (Femara), an aromatase inhibitor drug
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Kil, Kun-Eek; Biegon, Anat; Ding, Yu-Shin
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Controversies of aromatase localization in human breast cancer—Stromal versus parenchymal cells
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Miki, Yasuhiro; Suzuki, Takashi; Sasano, Hironobu
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Aromatase inhibition by R 76713: Experimental and clinical pharmacology
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Comparative effects of the aromatase inhibitor R76713 and of its enantiomers R83839 and R83842 on steroid biosynthesis in vitro and in vivo
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1H,6H-Triazolo[4,5-e]benzotriazole-3-oxides and 5,5’-(Z)-Diazene-1,2-diylbis(2-methyl-2H-1,2,3-benzotriazole) Derived from Chloronitrobenzotriazoles and Hydrazine
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Carta, Antonio; Piras, Sandra; Boatto, Gianpiero
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Nuclear Medicine and Biology, Vol. 36, Issue 3, p. 323-334
https://doi.org/10.1016/j.nucmedbio.2008.12.013

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Similar Records

Title: Radio-methyl vorozole and methods for making and using the same

Abstract

Citation Formats

(1H-azol-1-ylmethyl) substituted benzotriazole derivatives and pharmaceutical compositions containing them patent, July 1990

Process for preparing enantiomerically pure 6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl) methyl]-1-methyl-1H-benzotrizole patent, September 1997

Preparation and comparison of a pentafluorophenyl stationary phase for reversed-phase liquid chromatography journal, January 1990

Chromatographic classification and comparison of commercially available reversed-phase liquid chromatographic columns containing phenyl moieties using principal component analysis journal, June 2007

Distribution of Aromatase Cytochrome P450 Messenger Ribonucleic Acid in Adult Rhesus Monkey Brains1 journal, October 1997

Unique distribution of aromatase in the human brain: In vivo studies with PET and [N-methyl-11C]vorozole journal, April 2010

Development Summary towards a Manufacturable Process for R 83842 [( S )-6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole] † journal, May 2000

Synthesis and PET studies of [11C-cyano]letrozole (Femara), an aromatase inhibitor drug journal, February 2009

Synthesis and activity of 1H-benzimidazole and 1H-benzotriazole derivatives as inhibitors of Acanthamoeba castellanii journal, May 2004

Controversies of aromatase localization in human breast cancer—Stromal versus parenchymal cells journal, August 2007

Aromatase inhibition by R 76713: Experimental and clinical pharmacology journal, January 1989

R 76713, a new specific non-steroidal aromatase inhibitor journal, June 1989

Comparative effects of the aromatase inhibitor R76713 and of its enantiomers R83839 and R83842 on steroid biosynthesis in vitro and in vivo journal, December 1990

1H,6H-Triazolo[4,5-e]benzotriazole-3-oxides and 5,5’-(Z)-Diazene-1,2-diylbis(2-methyl-2H-1,2,3-benzotriazole) Derived from Chloronitrobenzotriazoles and Hydrazine journal, August 2005

Reinvestigation of the synthesis and evaluation of [N-methyl-11C]vorozole, a radiotracer targeting cytochrome P450 aromatase journal, April 2009

(1H-azol-1-ylmethyl) substituted benzotriazole derivatives and pharmaceutical compositions containing them
patent, July 1990

Process for preparing enantiomerically pure 6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl) methyl]-1-methyl-1H-benzotrizole
patent, September 1997

Preparation and comparison of a pentafluorophenyl stationary phase for reversed-phase liquid chromatography
journal, January 1990

Chromatographic classification and comparison of commercially available reversed-phase liquid chromatographic columns containing phenyl moieties using principal component analysis
journal, June 2007

Distribution of Aromatase Cytochrome P450 Messenger Ribonucleic Acid in Adult Rhesus Monkey Brains1
journal, October 1997

Unique distribution of aromatase in the human brain: In vivo studies with PET and [N-methyl-11C]vorozole
journal, April 2010

Development Summary towards a Manufacturable Process for R 83842 [( S )-6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole] ^†
journal, May 2000

Synthesis and PET studies of [¹¹C-cyano]letrozole (Femara), an aromatase inhibitor drug
journal, February 2009

Synthesis and activity of 1H-benzimidazole and 1H-benzotriazole derivatives as inhibitors of Acanthamoeba castellanii
journal, May 2004

Controversies of aromatase localization in human breast cancer—Stromal versus parenchymal cells
journal, August 2007

Aromatase inhibition by R 76713: Experimental and clinical pharmacology
journal, January 1989

R 76713, a new specific non-steroidal aromatase inhibitor
journal, June 1989

Comparative effects of the aromatase inhibitor R76713 and of its enantiomers R83839 and R83842 on steroid biosynthesis in vitro and in vivo
journal, December 1990

1H,6H-Triazolo[4,5-e]benzotriazole-3-oxides and 5,5’-(Z)-Diazene-1,2-diylbis(2-methyl-2H-1,2,3-benzotriazole) Derived from Chloronitrobenzotriazoles and Hydrazine
journal, August 2005

Reinvestigation of the synthesis and evaluation of [N-methyl-¹¹C]vorozole, a radiotracer targeting cytochrome P450 aromatase
journal, April 2009