Synthetic Approaches to the New Drugs Approved During 2015

Flick, Andrew C.; Ding, Hong X.; Leverett, Carolyn A.; Kyne, Robert E.; Liu, Kevin K.‐C.; Fink, Sarah; O’Donnell, Christopher J

doi:10.1021/acs.jmedchem.7b00010

Cited by 118 publications

(56 citation statements)

References 144 publications

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“…[3,4,6,7] However,t hese solvents are still commonly and widelyu sed in many laboratories because there are no alternatives effective enough for certain reaction cases.E ven in recent industrial processes to make pharmaceuticals,DCM is still occasionally used. [53,54] We therefore studied the application of 4-MeTHPi nr eactions where DCM is typically adopted, specifically,i no xidation, epoxidation, condensation, and olefin metathesis reactions (Scheme 10).…”

Section: Applications Of 4-methp As As Ubstitute For Halogenated Solvmentioning

confidence: 99%

4‐Methyltetrahydropyran (4‐MeTHP): Application as an Organic Reaction Solvent

Kobayashi

Tamura

Yoshimoto

et al. 2019

Chemistry An Asian Journal

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4-Methyltetrahydropyran (4-MeTHP) is ah ydrophobic cyclic ether with potential for industrial applications. We herein report, for the first time, ac omprehensive study on the performance of 4-MeTHP as an organic reaction solvent. Its broad application to organic reactions includes radical, Grignard, Wittig, organometallic, halogen-metal exchange, reduction,o xidation, epoxidation, amidation, esterification, metathesis, and other miscellaneous organic reactions. This breadth suggests4 -MeTHP can serve as a substitute for conventional ethers and harmful halogenated solvents. However,4 -MeTHP was found incompatible with strong Lewis acids, and the CÀOb ond was readily cleaved by treatment with BBr 3 .M oreover,t he radical-based degradation pathwayso f4 -MeTHP, THP and 2-MeTHF were elucidated on the basis of GC-MS analyses. The data reported herein is anticipated to be useful for ab road range of synthetic chemists,e specially industrial process chemists, when selecting the reactions olvent with green chemistry perspectives.[a] Dr.Scheme1.Manufacturing process of 4-MeTHP. IPEA = isopentyl alcohol, MHP = 2-hydroxy-4-methyltetrahydropyran, MPD = 3-methylpentan-1,5-diol.

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Section: Applications Of 4-methp As As Ubstitute For Halogenated Solvmentioning

confidence: 99%

4‐Methyltetrahydropyran (4‐MeTHP): Application as an Organic Reaction Solvent

Kobayashi

Tamura

Yoshimoto

et al. 2019

Chemistry An Asian Journal

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“…3 A recent analysis on structures of USFDAapproved drugs administered in combination with other drugs as reported by Njardarson et al revealed that the major importance of these heterocycles in combination drugs is in variety of therapeutic uses. 4 The rich literature [5][6][7][8][9][10][11][12][13][14] on the synthesis of these USFDA-approved drugs is also gaining momentum since for the clinical use of a drug, the drug molecule has be synthesized on a pilot scale using a suitable toolbox of organic chemistry. 15 A plot of the number of publications versus year of publication performed using Sci-Finder 16 for the search string 'synthesis of heterocyclic scaffolds' revealed the increasing popularity of heterocyclic scaffolds synthesized via several organic transformations (Fig.…”

Section: Introductionmentioning

confidence: 99%

A decennary update on applications of metal nanoparticles (MNPs) in the synthesis of nitrogen- and oxygen-containing heterocyclic scaffolds

et al. 2020

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“…Structure of retaglpitin (184) and antidiabetic drug.Evogliptin: (R)-2,4,5-Trifluorophenylalanine 38b is required for the synthesis of evogliptin (185,Figure 8), an antidiabetic drug in the dipeptidyl peptidase-4 (DPP-4) inhibitor or "gliptin" class of drugs. The South Korean pharmaceutical company Dong-A ST developed evogliptin (185) and it is currently approved for use in South Korea[121][122][123].…”

mentioning

confidence: 99%

Fluorinated phenylalanines: synthesis and pharmaceutical applications

Awad¹,

Ayoup²

2020

Beilstein J. Org. Chem.

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Recent advances in the chemistry of peptides containing fluorinated phenylalanines (Phe) represents a hot topic in drug research over the last few decades. ᴅ- or ʟ-fluorinated phenylalanines have had considerable industrial and pharmaceutical applications and they have been expanded also to play an important role as potential enzyme inhibitors as well as therapeutic agents and topography imaging of tumor ecosystems using PET. Incorporation of fluorinated aromatic amino acids into proteins increases their catabolic stability especially in therapeutic proteins and peptide-based vaccines. This review seeks to summarize the different synthetic approaches in the literature to prepare ᴅ- or ʟ-fluorinated phenylalanines and their pharmaceutical applications with a focus on published synthetic methods that introduce fluorine into the phenyl, the β-carbon or the α-carbon of ᴅ-or ʟ-phenylalanines.

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Synthetic Approaches to the New Drugs Approved During 2015

Cited by 118 publications

References 144 publications

4‐Methyltetrahydropyran (4‐MeTHP): Application as an Organic Reaction Solvent

4‐Methyltetrahydropyran (4‐MeTHP): Application as an Organic Reaction Solvent

A decennary update on applications of metal nanoparticles (MNPs) in the synthesis of nitrogen- and oxygen-containing heterocyclic scaffolds

Fluorinated phenylalanines: synthesis and pharmaceutical applications

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