Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II–III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas

Chemical Reviews, Journal Year: 2016, Volume and Issue: 116(2), P. 422 - 518

Published: Jan. 12, 2016

ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTNext Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II–III Clinical Trials Major Pharmaceutical Companies: New Structural Trends and Therapeutic AreasYu Zhou†, Jiang Wang†, Zhanni Gu†, Shuni Wei Zhu†, José Luis Aceña*‡§, Vadim A. Soloshonok*‡∥, Kunisuke Izawa*⊥, Hong Liu*†View Author Information† Key Laboratory Receptor Research, Shanghai Institute Materia Medica, Chinese Academy Sciences, 555 Zu Chong Zhi Road, 201203, China‡ Department Organic Chemistry I, Faculty Chemistry, University the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain§ Autónoma Madrid, Cantoblanco, 28049 Spain∥ IKERBASQUE, Foundation for Science, María Díaz de Haro 48013 Bilbao, Spain⊥ Hamari Chemicals Ltd., 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka, Japan 533-0024*E-mail: [email protected]*E-mail: protected]Cite this: Chem. Rev. 2016, 116, 2, 422–518Publication Date (Web):January 12, 2016Publication History Received6 July 2015Published online12 January 2016Published inissue 27 2016https://pubs.acs.org/doi/10.1021/acs.chemrev.5b00392https://doi.org/10.1021/acs.chemrev.5b00392review-articleACS PublicationsCopyright © 2016 American Chemical SocietyRequest reuse permissionsArticle Views31495Altmetric-Citations2070LEARN ABOUT THESE METRICSArticle Views are COUNTER-compliant sum full text article downloads since November 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated to reflect usage leading up last few days.Citations number other articles citing this article, calculated by Crossref daily. Find more information about citation counts.The Altmetric Attention Score is a quantitative measure attention that research has received online. Clicking on donut icon will load page at altmetric.com with additional details score social media presence given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Chemical structure,Fluorine,Inhibitors,Pharmaceuticals,Reaction products Get e-Alerts

Language: Английский

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Monofluorination of Organic Compounds: 10 Years of Innovation

Chemical Reviews, Journal Year: 2015, Volume and Issue: 115(17), P. 9073 - 9174

Published: April 9, 2015

ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTMonofluorination of Organic Compounds: 10 Years InnovationPier Alexandre Champagne, Justine Desroches, Jean-Denys Hamel, Mathilde Vandamme, and Jean-François Paquin*View Author Information Canada Research Chair in Medicinal Chemistry, CGCC, PROTEO, Département de Chimie, Université Laval, 1045 Avenue la Médecine, Québec (QC), G1V 0A6*E-mail: [email protected]Cite this: Chem. Rev. 2015, 115, 17, 9073–9174Publication Date (Web):April 9, 2015Publication History Received17 December 2014Published online9 April 2015Published inissue 9 September 2015https://pubs.acs.org/doi/10.1021/cr500706ahttps://doi.org/10.1021/cr500706areview-articleACS PublicationsCopyright © 2015 American Chemical SocietyRequest reuse permissionsArticle Views27866Altmetric-Citations766LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum full text article downloads since November 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated to reflect usage leading up last few days.Citations number other articles citing this article, calculated by Crossref daily. Find more information about citation counts.The Altmetric Attention Score is a quantitative measure attention that research has received online. Clicking on donut icon will load page at altmetric.com with additional details score social media presence for given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Anions,Halogenation,Hydrocarbons,Reaction products,Stereoselectivity Get e-Alerts

Language: Английский

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¹⁸F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography

Chemical Reviews, Journal Year: 2016, Volume and Issue: 116(2), P. 719 - 766

Published: Jan. 11, 2016

Diverse radiochemistry is an essential component of nuclear medicine; this includes imaging techniques such as positron emission tomography (PET). As such, PET can track diseases at early stage development, help patient care planning through personalized medicine and support drug discovery programs. Fluorine-18 the most frequently used radioisotope in radiopharmaceuticals for both clinical preclinical research. Its physical characteristics (97% β+ decay, 109.8 min half-life, 635 keV energy) high specific activity make it attractive nuclide labeling molecular imaging. Arenes heteroarenes are privileged candidates 18F-incorporation they metabolically robust therefore widely by medicinal chemists radiochemists alike. For many years, range (hetero)arenes amenable to 18F-fluorination was limited lack chemically diverse precursors, radiochemical methods allowing selectivity efficiency (radiochemical yield purity, activity, radio-scalability). The appearance late-stage fluorination reactions catalyzed transition metal or small organic molecules (organocatalysis) has encouraged much research on use these activation manifolds 18F-fluorination. In piece, we review all known date install 18F substituent other key 18F-motifs (e.g., CF3, CHF2, OCF3, SCF3, OCHF2) relevance onto (hetero)arenes. field changed significantly past five current trend suggests that space available applications will expand rapidly near future.

Language: Английский

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Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation

Chemical Reviews, Journal Year: 2016, Volume and Issue: 116(14), P. 8003 - 8104

Published: June 24, 2016

The high utility of halogenated organic compounds has prompted the development a vast number transformations which install carbon-halogen motif. Traditional routes to these building blocks have commonly involved multiple steps, harsh reaction conditions, and use stoichiometric and/or toxic reagents. In this regard, using transition metals catalyze synthesis organohalides become mature field in itself, applying technologies allowed for decrease production waste, higher levels regio- stereoselectivity, ability produce enantioenriched target compounds. Furthermore, offer distinct advantage possessing diverse spectrum mechanistic possibilities translate capability apply new substrate classes afford novel difficult-to-access structures. This Review provides comprehensive coverage modern metal-catalyzed syntheses via array mechanisms. Attention is given seminal organometallic studies led corresponding catalytic processes being realized. By breaking down into aryl, vinyl, alkyl halides, it becomes clear methods surfaced as most favored each individual class. general, pronounced shift toward C-H bonds key functional groups, addition proceed by catalytic, radical-based mechanisms occurred. Although always evolving, appears be heading direction starting materials with significantly lower degree prefunctionalization less expensive abundant metal catalysts.

Language: Английский

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Modern Approaches for Asymmetric Construction of Carbon–Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs

Chemical Reviews, Journal Year: 2018, Volume and Issue: 118(7), P. 3887 - 3964

Published: April 2, 2018

New methods for preparation of tailor-made fluorine-containing compounds are in extremely high demand nearly every sector chemical industry. The asymmetric construction quaternary C-F stereogenic centers is the most synthetically challenging and, consequently, least developed area research. As a reflection this apparent methodological deficit, pharmaceutical drugs featuring constitute less than 1% all medicines currently on market or clinical development. Here we provide comprehensive review current research activity area, including such general directions as electrophilic fluorination via organocatalytic and transition-metal catalyzed reactions, elaboration substrates alkylations, Mannich, Michael, aldol additions, cross-coupling biocatalytic approaches.

Language: Английский

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Key Green Chemistry research areas from a pharmaceutical manufacturers’ perspective revisited

Green Chemistry, Journal Year: 2018, Volume and Issue: 20(22), P. 5082 - 5103

Published: Jan. 1, 2018

The ACS Green Chemistry Institute® Pharmaceutical Roundtable has assembled an updated list of key research areas to highlight transformations and reaction media where more sustainable technologies would be most impactful.

Language: Английский

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Polymeric Nanostructures for Imaging and Therapy

Chemical Reviews, Journal Year: 2015, Volume and Issue: 115(19), P. 10967 - 11011

Published: Aug. 4, 2015

ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTPolymeric Nanostructures for Imaging and TherapyMahmoud Elsabahy*†‡§, Gyu Seong Heo†, Soon-Mi Lim†, Guorong Sun†, Karen L. Wooley*†View Author Information† Department of Chemistry, Chemical Engineering, Materials Science & Laboratory Synthetic-Biologic Interactions, Texas A&M University, P.O. Box 30012, 3255 TAMU, College Station, 77842-3012, United States‡ Pharmaceutics, Faculty Pharmacy, Assiut International Center Nanomedicine, Al-Rajhy Liver Hospital, 71515 Assiut, Egypt§ Misr University Technology, Sixth October City, Giza, Egypt*E-mail: [email protected]. Tel.: +2 088 2 2080711. Fax: 0882 2080774.*E-mail: +1 979 845 4077. 862 1137.Cite this: Chem. Rev. 2015, 115, 19, 10967–11011Publication Date (Web):August 4, 2015Publication History Received4 March 2015Published online4 August inissue 14 2015https://pubs.acs.org/doi/10.1021/acs.chemrev.5b00135https://doi.org/10.1021/acs.chemrev.5b00135review-articleACS PublicationsCopyright © 2015 American SocietyRequest reuse permissionsArticle Views11913Altmetric-Citations413LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum full text article downloads since November 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated to reflect usage leading up last few days.Citations number other articles citing this article, calculated by Crossref daily. Find more information about citation counts.The Altmetric Attention Score is a quantitative measure attention that research has received online. Clicking on donut icon will load page at altmetric.com with additional details score social media presence given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Biological imaging,Cancer therapy,Nanoparticles,Pharmaceuticals,Polymers Get e-Alerts

Language: Английский

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Self‐Protective Room‐Temperature Phosphorescence of Fluorine and Nitrogen Codoped Carbon Dots

Advanced Functional Materials, Journal Year: 2018, Volume and Issue: 28(37)

Published: July 25, 2018

Abstract The unstable triplet excited state is a core problem when developing self‐protective room temperature phosphorescence (RTP) in carbon dots (CDs). Here, fluorine and nitrogen codoped (FNCDs) with long‐lived states, emitting pH‐stabilized blue fluorescence pH‐responsive green RTP, are reported for the first time. RTP of FNCDs arises from n–π * electron transitions CN/CN bonds small energy gap between singlet states at temperature. Moreover, interdot/intradot hydrogen steric protection CF reduce quenching by oxygen emission shows outstanding reversibility, while has good pH stability. Based on these FNCDs, data encoding/reading strategy advanced anticounterfeiting proposed via time‐resolved luminescence imaging techniques, as well steganography complex patterns.

Language: Английский

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A Perspective on Continuous Flow Chemistry in the Pharmaceutical Industry

Organic Process Research & Development, Journal Year: 2020, Volume and Issue: 24(10), P. 1802 - 1813

Published: Jan. 10, 2020

Continuous flow manufacture is an innovative technology platform, which gaining momentum within the pharmaceutical industry. The key advantages of continuous include faster and safer reactions, can be more environmentally friendly, smaller footprint, better quality product, critically, ability to perform chemistry that difficult or impossible do in batch mode. Globally, significant efforts have been made develop manufacturing flexibility robustness processes used produce chemicals a way, yet despite these scientific developments, major challenge for industry established application commercially relevant examples. identification opportunities apply solutions current also critical success this new fine chemical companies. This review highlights industrial hurdles importance education showcases recent (2018–2019) examples where utilization has successfully performed.

Language: Английский

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Toolbox for Distal C–H Bond Functionalizations in Organic Molecules

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(6), P. 5682 - 5841

Published: Oct. 18, 2021

Transition-metal-catalyzed C–H activation has developed a contemporary approach to the omnipresent area of retrosynthetic disconnection. Scientific researchers have been tempted take help this methodology plan their synthetic discourses. This paradigm shift helped in development industrial units as well, making synthesis natural products and pharmaceutical drugs step-economical. In vast zone bond activation, functionalization proximal bonds gained utmost popularity. Unlike bonds, distal is more strenuous requires distinctly specialized techniques. review, we compiled various methods adopted functionalize mechanistic insights within each these procedures, scope methodology. With give complete overview expeditious progress made field organic chemistry while also highlighting its pitfalls, thus leaving open for further modifications.

Language: Английский

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