Author: Heid, Richard ; Hayward, Cheryl ; Zeldis, Joseph ; Liu, Weiguo ; Barnhart, Richard W. ; Sutherland, Karen ; Van Alsten, John ; Fung, Peter ; Varsolona, Richard ; Houck, Timothy ; Samp, Lacey ; Li, Bryan

We have successfully adapted a Suzuki-Miyaura coupling reaction to a continuous flow process.The reaction was a triphasic mixture involved with two liquid phases that are only partially miscible in addition to the presence of an insoluble catalyst as a solid phase.The reaction required very rapid reaction heat up and mixing, which were difficult to achieve under batch conditions.A plug flow reactor (PFR) equipped with a static mixer was implemented in this continuous flow process, and the heterogenous reaction mixture was well handled, which is attributed to the high velocity flow rates and fast reaction kinetics.The reaction was successfully carried out on a 1.6 kg scale to give 80% isolated yield of the product with superior reaction high-performance liquid chromatog. profile to the batch process.

18 Jan 2019·Organic LettersQ1 · CHEMISTRY

Synthesis of 4-Iodoisoquinolin-1(2H)-ones by a Dirhodium(II)-Catalyzed 1,4-Bisfunctionalization of Isoquinolinium Iodide Salts

Q1 · CHEMISTRY

Article

Author: Wang, Yuanhua ; Fang, Zaixiang ; Wang, Yi

An efficient Rh₂(II,II)-catalyzed reaction has been developed under mild conditions. This synthetic method proceeds through iodination/oxidation of readily available isoquinolinium iodide salts under aerobic conditions with good to excellent yields. 4-Iodoisoquinolin-1(2 H)-ones are important building blocks for biologically and medicinally important compounds. The developed methodology was applied to the gram-scale synthesis of a key intermediate in the synthesis of the CRTH2 antagonist CRA-680.

27 Feb 2014·Journal of Medicinal ChemistryQ1 · MEDICINE

Discovery of Isoquinolinone Indole Acetic Acids as Antagonists of Chemoattractant Receptor Homologous Molecule Expressed on Th2 Cells (CRTH2) for the Treatment of Allergic Inflammatory Diseases

Q1 · MEDICINE

Article

Author: Mansour, Tarek S. ; Leung, Louis ; Lowe, Michael ; Xu, Xin ; Huang, Adrian ; Morgan, Paul ; Follows, Bruce ; Moretto, Alessandro ; Hubeau, Cedric ; Page, Karen ; Williams, Cara ; Saiah, Eddine ; Fish, Susan ; Thomason, Jennifer ; Janz, Kristin ; Kaila, Neelu

Previously we reported the discovery of CRA-898 (1), a diazine indole acetic acid containing CRTH2 antagonist. This compound had good in vitro and in vivo potency, low rates of metabolism, moderate permeability, and good oral bioavailability in rodents. However, it showed low oral exposure in nonrodent safety species (dogs and monkeys). In the current paper, we wish to report our efforts to understand and improve the poor PK in nonrodents and development of a new isoquinolinone subseries that led to identification of a new development candidate, CRA-680 (44). This compound was efficacious in both a house dust mouse model of allergic lung inflammation (40 mg/kg qd) as well as a guinea pig allergen challenge model of lung inflammation (20 mg/kg bid).

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Indication	Highest Phase	Country/Location	Organization	Date
Anaphylaxis	Preclinical	United States	Pfizer Inc.	27 Feb 2014

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