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Article ; Online: Synthesis of BI 894416 and BI 1342561, two potent and selective spleen tyrosine kinase inhibitors, labeled with carbon 14 and with deuterium.

Latli, Bachir / Hrapchak, Matt J / Samankumara, Lalith P / Fandrick, Daniel R / Pennino, Scott / Lee, Heewon / Song, Jinhua J

Journal of labelled compounds & radiopharmaceuticals

2023 Volume 66, Issue 4-6, Page(s) 155–168

Abstract: R)-4-((R)-1-((6-(1-[tert-butyl]-1H-pyrazol-4-yl)-2-methyl-2H-pyrazolo[3,4-d]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one (BI 894416, 1) and (R)-4-((R)-1-((6-(1-[tert-butyl]-1H-pyrazol-4-yl)-2,3-dimethyl-2H-indazol-4-yl)oxy)ethyl)pyrrolidin-2-one (BI 1342561, ...

Abstract	(R)-4-((R)-1-((6-(1-[tert-butyl]-1H-pyrazol-4-yl)-2-methyl-2H-pyrazolo[3,4-d]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one (BI 894416, 1) and (R)-4-((R)-1-((6-(1-[tert-butyl]-1H-pyrazol-4-yl)-2,3-dimethyl-2H-indazol-4-yl)oxy)ethyl)pyrrolidin-2-one (BI 1342561, 2) are two new potent and selective spleen tyrosine kinase inhibitors developed to treat severe asthma. Both compounds have similar structures and they differ only in the bicyclic moiety 2-methyl-2H-pyrazolo[4,3-c]pyridine in 1 versus 2,3-dimethyl-2H-indazole in 2. In the carbon 14 synthesis, 1-(1-[tert-butyl]-1H-pyrazol-4-yl)ethan-1-one-1-
MeSH term(s)	Carbon Radioisotopes/chemistry ; Deuterium ; Tyrosine Kinase Inhibitors ; Spleen
Chemical Substances	Carbon Radioisotopes ; Deuterium (AR09D82C7G) ; Tyrosine Kinase Inhibitors
Language	English
Publishing date	2023-04-24
Publishing country	England
Document type	Journal Article
ZDB-ID	196095-7
ISSN	1099-1344 ; 0362-4803 ; 0022-2135
ISSN (online)	1099-1344
ISSN	0362-4803 ; 0022-2135
DOI	10.1002/jlcr.4024
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Article ; Online: Practical Synthesis of Terminal Vinyl Fluorides.

Volchkov, Ivan / Powell, Brent V / Zatolochnaya, Olga V / Leung, Joyce C / Pennino, Scott / Wu, Lifen / Gonnella, Nina C / Bhaskararao, Bangaru / Kozlowski, Marisa C / Reeves, Jonathan T

The Journal of organic chemistry

2023 Volume 88, Issue 15, Page(s) 10881–10904

Abstract: The synthesis of di- and trisubstituted vinyl fluorides with high isomeric purity remains a challenge for organic synthesis. While many methods exist to access these compounds, the separation of the desired isomer from the minor isomer and/or starting ... ...

Abstract	The synthesis of di- and trisubstituted vinyl fluorides with high isomeric purity remains a challenge for organic synthesis. While many methods exist to access these compounds, the separation of the desired isomer from the minor isomer and/or starting materials often is difficult. Herein, we report a practical method to access di- and trisubstituted vinyl fluorides via a selective Horner-Wadsworth-Emmons olefination/hydrolysis, which provides crystalline 2-fluoroacrylic acids in high (>98%)
Language	English
Publishing date	2023-07-13
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.3c00917
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Article ; Online: Synthesis of stable isotope-labelled firocoxib.

Latli, Bachir / Gao, Amy / Kvaternick, Valerie / Tecle, Berhane / Pennino, Scott / Yee, Nathan K / Song, Jeff

Journal of labelled compounds & radiopharmaceuticals

2020 Volume 63, Issue 8, Page(s) 386–392

Abstract: Firocoxib (ML-1,785,713) is a nonsteroidal, potent, and selective COX-2 inhibitor, approved for the control of pain and inflammation associated with osteoarthritis in dogs and horses, as well as to control postoperative pain and inflammation in dogs. We ... ...

Abstract	Firocoxib (ML-1,785,713) is a nonsteroidal, potent, and selective COX-2 inhibitor, approved for the control of pain and inflammation associated with osteoarthritis in dogs and horses, as well as to control postoperative pain and inflammation in dogs. We employed a six-step synthesis to prepare firocoxib-[
MeSH term(s)	4-Butyrolactone/analogs & derivatives ; 4-Butyrolactone/chemical synthesis ; 4-Butyrolactone/chemistry ; Animals ; Chemistry Techniques, Synthetic ; Dogs ; Horses ; Isotope Labeling ; Radiochemistry ; Sulfones/chemical synthesis ; Sulfones/chemistry
Chemical Substances	Sulfones ; 4-Butyrolactone (OL659KIY4X) ; firocoxib (Y6V2W4S4WT)
Language	English
Publishing date	2020-05-05
Publishing country	England
Document type	Journal Article
ZDB-ID	196095-7
ISSN	1099-1344 ; 0362-4803 ; 0022-2135
ISSN (online)	1099-1344
ISSN	0362-4803 ; 0022-2135
DOI	10.1002/jlcr.3842
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Article ; Online: Sulfone-Mediated S

Patel, Nitinchandra D / Wei, Xudong / Byrne, Denis / Narayanan, Bikshandarkoil A / Pennino, Scott / Sarvestani, Max / Saha, Anjan / Haddad, Nizar / Kapadia, Suresh / Lorenz, Jon C / DeCroos, Philomen / Ye, Andrew / Lee, Heewon / Grinberg, Nelu / Hossain, Azad / Busacca, Carl A / Yee, Nathan K / Senanayake, Chris H

The Journal of organic chemistry

2020 Volume 85, Issue 13, Page(s) 8339–8351

Abstract: An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive ... ...

Abstract	An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive S
MeSH term(s)	Antiviral Agents ; Ethers ; Hepacivirus ; Hepatitis C ; Humans ; Protease Inhibitors/pharmacology ; Sulfones ; Viral Nonstructural Proteins
Chemical Substances	Antiviral Agents ; Ethers ; Protease Inhibitors ; Sulfones ; Viral Nonstructural Proteins
Language	English
Publishing date	2020-06-19
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.0c00554
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Article ; Online: Automated Solid Phase Extraction (SPE) LC/NMR Applied to the Structural Analysis of Extractable Compounds from a Pharmaceutical Packaging Material of Construction.

Norwood, Daniel L / Mullis, James O / Davis, Mark / Pennino, Scott / Egert, Thomas / Gonnella, Nina C

PDA journal of pharmaceutical science and technology

2013 Volume 67, Issue 3, Page(s) 267–287

Abstract: The structural analysis (i.e., identification) of organic chemical entities leached into drug product formulations has traditionally been accomplished with techniques involving the combination of chromatography with mass spectrometry. These include gas ... ...

Abstract	The structural analysis (i.e., identification) of organic chemical entities leached into drug product formulations has traditionally been accomplished with techniques involving the combination of chromatography with mass spectrometry. These include gas chromatography/mass spectrometry (GC/MS) for volatile and semi-volatile compounds, and various forms of liquid chromatography/mass spectrometry (LC/MS or HPLC/MS) for semi-volatile and relatively non-volatile compounds. GC/MS and LC/MS techniques are complementary for structural analysis of leachables and potentially leachable organic compounds produced via laboratory extraction of pharmaceutical container closure/delivery system components and corresponding materials of construction. Both hyphenated analytical techniques possess the separating capability, compound specific detection attributes, and sensitivity required to effectively analyze complex mixtures of trace level organic compounds. However, hyphenated techniques based on mass spectrometry are limited by the inability to determine complete bond connectivity, the inability to distinguish between many types of structural isomers, and the inability to unambiguously determine aromatic substitution patterns. Nuclear magnetic resonance spectroscopy (NMR) does not have these limitations; hence it can serve as a complement to mass spectrometry. However, NMR technology is inherently insensitive and its ability to interface with chromatography has been historically challenging. This article describes the application of NMR coupled with liquid chromatography and automated solid phase extraction (SPE-LC/NMR) to the structural analysis of extractable organic compounds from a pharmaceutical packaging material of construction. The SPE-LC/NMR technology combined with micro-cryoprobe technology afforded the sensitivity and sample mass required for full structure elucidation. Optimization of the SPE-LC/NMR analytical method was achieved using a series of model compounds representing the chemical diversity of extractables. This study demonstrates the complementary nature of SPE-LC/NMR with LC/MS for this particular pharmaceutical application. Lay abstract: The identification of impurities leached into drugs from the components and materials associated with pharmaceutical containers, packaging components, and materials has historically been done using laboratory techniques based on the combination of chromatography with mass spectrometry. Such analytical techniques are widely recognized as having the selectivity and sensitivity required to separate the complex mixtures of impurities often encountered in such identification studies, including both the identification of leachable impurities as well as potential leachable impurities produced by laboratory extraction of packaging components and materials. However, while mass spectrometry-based analytical techniques have limitations for this application, newer analytical techniques based on the combination of chromatography with nuclear magnetic resonance spectroscopy provide an added dimension of structural definition. This article describes the development, optimization, and application of an analytical technique based on the combination of chromatography and nuclear magnetic resonance spectroscopy to the identification of potential leachable impurities from a pharmaceutical packaging material. The complementary nature of the analytical techniques for this particular pharmaceutical application is demonstrated.
MeSH term(s)	Chromatography, Liquid ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Pharmaceutical Preparations ; Solid Phase Extraction ; Solid Phase Microextraction
Chemical Substances	Pharmaceutical Preparations
Language	English
Publishing date	2013-03-26
Publishing country	United States
Document type	Journal Article
ZDB-ID	1205009-x
ISSN	1948-2124 ; 0277-3406 ; 1076-397X ; 0279-7976 ; 1079-7440
ISSN (online)	1948-2124
ISSN	0277-3406 ; 1076-397X ; 0279-7976 ; 1079-7440
DOI	10.5731/pdajpst.2013.00920
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Zs.B 766: Show issues			Location: Je nach Verfügbarkeit (siehe Angabe bei Bestand) bis Jg. 2021: Bestellungen von Artikeln über das Online-Bestellformular ab Jg. 2022: Lesesaal (EG)
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Article: Sulfone-Mediated SNAr Reaction as a Powerful Tool for the Synthesis of 4-Quinolinyl Ethers and More—Application to the Synthesis of HCV NS3/4a Protease Inhibitor BI 201420

Patel, Nitinchandra D. / Wei, Xudong / Byrne, Denis / Narayanan, Bikshandarkoil A. / Pennino, Scott / Sarvestani, Max / Saha, Anjan / Haddad, Nizar / Kapadia, Suresh / Lorenz, Jon C. / DeCroos, Philomen / Ye, Andrew / Lee, Heewon / Grinberg, Nelu / Hossain, Azad / Busacca, Carl A. / Yee, Nathan K. / Senanayake, Chris H.

Journal of organic chemistry. 2020 May 28, v. 85, no. 13

2020

Abstract: An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive SNAr reaction of 4-quinolinyl sulfones with a range of structurally diversified 1°, 2°, and 3° alcohols with a wide substrate scope and high ... ...

Abstract	An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive SNAr reaction of 4-quinolinyl sulfones with a range of structurally diversified 1°, 2°, and 3° alcohols with a wide substrate scope and high yields. By adapting this methodology, a convergent synthesis of a complex target of HCV NS3/4a protease inhibitor BI 201420 was accomplished.
Keywords	alcohols ; ethers ; journals ; organic chemistry ; proteinase inhibitors
Language	English
Dates of publication	2020-0528
Size	p. 8339-8351.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.0c00554
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Article ; Online: Identification of a process impurity formed during synthesis of a nevirapine analogue HIV NNRT inhibitor using LC/MS and forced degradation studies.

Qiu, Fenghe / Pennino, Scott / Busacca, Carl A / Norwood, Daniel L

Journal of pharmaceutical and biomedical analysis

2009 Volume 49, Issue 3, Page(s) 733–738

Abstract: Impurities in pharmaceutical products do not enhance the desired therapeutic effect and may, of course, have adverse effects. Impurities must therefore be limited or controlled for quality and safety considerations. Structural identification of an ... ...

Abstract	Impurities in pharmaceutical products do not enhance the desired therapeutic effect and may, of course, have adverse effects. Impurities must therefore be limited or controlled for quality and safety considerations. Structural identification of an impurity is the first step in understanding the chemistry of its formation and subsequently controlling the impurity. In this article, the chemical structure of an unknown by-product formed during the synthesis of a nevirapine analogue HIV NNRT inhibitor was identified using a combination of low resolution, high resolution and H/D exchange LC/MS and LC/MS/MS. The origin of the impurity was investigated through a series of photo- and oxidative stress studies. It was concluded that this impurity is formed via a side-reaction of the last intermediate with the oxidant used in the synthesis.
MeSH term(s)	Chromatography, High Pressure Liquid ; Drug Contamination ; Light ; Mass Spectrometry ; Nevirapine/analogs & derivatives ; Nevirapine/analysis ; Nevirapine/chemical synthesis ; Oxidants/chemistry ; Oxidation-Reduction ; Oxidative Stress ; Photochemistry ; Reverse Transcriptase Inhibitors/analysis ; Reverse Transcriptase Inhibitors/chemical synthesis ; Solutions ; Solvents
Chemical Substances	Oxidants ; Reverse Transcriptase Inhibitors ; Solutions ; Solvents ; Nevirapine (99DK7FVK1H)
Language	English
Publishing date	2009-04-05
Publishing country	England
Document type	Journal Article
ZDB-ID	604917-5
ISSN	1873-264X ; 0731-7085
ISSN (online)	1873-264X
ISSN	0731-7085
DOI	10.1016/j.jpba.2009.01.010
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Article: Enantioselective Synthesis of α-(Hetero)aryl Piperidines through Asymmetric Hydrogenation of Pyridinium Salts and Its Mechanistic Insights

Organic letters. 2018 Mar. 02, v. 20, no. 5

2018

Abstract: Enantioselective synthesis of α-aryl and α-heteroaryl piperidines is reported. The key step is an iridium-catalyzed asymmetric hydrogenation of substituted N-benzylpyridinium salts. High levels of enantioselectivity up to 99.3:0.7 er were obtained for a ... ...

Abstract	Enantioselective synthesis of α-aryl and α-heteroaryl piperidines is reported. The key step is an iridium-catalyzed asymmetric hydrogenation of substituted N-benzylpyridinium salts. High levels of enantioselectivity up to 99.3:0.7 er were obtained for a range of α-heteroaryl piperidines. DFT calculations support an outersphere dissociative mechanism for the pyridinium reduction. Notably, initial protonation of the final enamine intermediate determines the stereochemical outcome of the transformation rather than hydride reduction of the resultant iminium intermediate.
Keywords	chemical structure ; enamines ; enantioselective synthesis ; enantioselectivity ; hydrides ; hydrogenation ; piperidines ; salts ; stereochemistry
Language	English
Dates of publication	2018-0302
Size	p. 1333-1337.
Publishing place	American Chemical Society
Document type	Article
ISSN	1523-7052
DOI	10.1021/acs.orglett.8b00067
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Article: Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra-

ACS catalysis

2018 Volume 8, Issue 11, Page(s) 10190–10209

Abstract: Metal-catalyzed cross-coupling reactions are extensively employed in both academia and industry for the synthesis of biaryl derivatives for applications to both medicine and material science. Application of these methods to prepare tetra- ...

Abstract	Metal-catalyzed cross-coupling reactions are extensively employed in both academia and industry for the synthesis of biaryl derivatives for applications to both medicine and material science. Application of these methods to prepare tetra-
Language	English
Publishing date	2018-09-20
Publishing country	United States
Document type	Journal Article
ISSN	2155-5435
ISSN	2155-5435
DOI	10.1021/acscatal.8b02509
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Article ; Online: Enantioselective Synthesis of α-(Hetero)aryl Piperidines through Asymmetric Hydrogenation of Pyridinium Salts and Its Mechanistic Insights.

Organic letters

2018 Volume 20, Issue 5, Page(s) 1333–1337

Abstract	Enantioselective synthesis of α-aryl and α-heteroaryl piperidines is reported. The key step is an iridium-catalyzed asymmetric hydrogenation of substituted N-benzylpyridinium salts. High levels of enantioselectivity up to 99.3:0.7 er were obtained for a range of α-heteroaryl piperidines. DFT calculations support an outersphere dissociative mechanism for the pyridinium reduction. Notably, initial protonation of the final enamine intermediate determines the stereochemical outcome of the transformation rather than hydride reduction of the resultant iminium intermediate.
MeSH term(s)	Catalysis ; Hydrogenation ; Iridium ; Models, Chemical ; Molecular Structure ; Oxidation-Reduction ; Piperidines/chemical synthesis ; Pyridinium Compounds/chemistry ; Stereoisomerism
Chemical Substances	Piperidines ; Pyridinium Compounds ; Iridium (44448S9773)
Language	English
Publishing date	2018-02-20
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
ISSN	1523-7052
ISSN (online)	1523-7052
DOI	10.1021/acs.orglett.8b00067
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