cas 87199-15-3, 3-(Hydroxymethyl)phenylboronic acid

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Effective Utilization of Flow Chemistry: Use of Unstable Intermediates, Inhibition of Side Reactions, and Scale-Up for Boronic Acid Synthesis
Flow chemistry processes for boronic acid syntheses utilizing lithiation-borylation have been developed. The side reactions in the lithiation step that occur in batch were suppressed, and unstable lithium intermediates were handled safely. Flow technology was applied to several kinds of boronic acid syntheses, and scale-up was successfully conducted to allow kilogram-scale production. Some of the key benefits of flow flash chemistry were utilized, both to avoid side reactions and to enable dianion chemistry that is difficult to perform successfully in batch reactions. The examples showed further perspectives on the utility of flow technologies for process development.
Usutani, Hirotsugu,Cork, David G.
p. 741 - 746
(2018/06/11)

Design and synthesis of novel meta-linked phenylglycine macrocyclic FVIIa inhibitors
Two novel series of meta-linked phenylglycine-based macrocyclic FVIIa inhibitors have been designed to improve the rodent metabolic stability and PK observed with the precursor para-linked phenylglycine macrocycles. Through iterative structure-based design and optimization, the TF/ FVIIa Ki was improved to subnanomolar levels with good clotting activity, metabolic stability, and permeability.
Richter, Jeremy M.,Cheney, Daniel L.,Bates, J. Alex,Wei, Anzhi,Luettgen, Joseph M.,Rendina, Alan R.,Harper, Timothy M.,Narayanan, Rangaraj,Wong, Pancras C.,Seiffert, Dietmar,Wexler, Ruth R.,Priestley, E. Scott
supporting information
p. 67 - 72
(2017/12/12)

MACROCYCLIC FACTOR VIIA INHIBITORS
The present invention provides compounds of Formula (I) as defined in the specification and compositions comprising any of such novel compounds. These compounds are Factor VIIa inhibitors which may be used as medicaments.
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Paragraph 00214

(2015/01/09)

Binding of E-selectin or P-selectin to sialyl Lewisx or sialyl-Lewisa
This invention relates to compounds that inhibit the binding of E-selectin and/or P-selectin to sialyl-Lewisx or sialyl-Lewisa presented on a cell surface having the general structure STR1 wherein X is selected from the group consisting of --(CH2)n CO2 H, --O(CH2)m CO2 H, --(CH2)n O(CH2)m CO2 H, --CONH(CH2)m CO2 H, --CH(OZ)(CO2 H), --CH(Z)(CO2 H), --(CH2)n SO3 H, --(CH2)n PO3 D1 D2, --NH(CH2)m CO2 H, --CONH(CHR6)CO2 H, (1-H-tetrazolyl-5-alkyl-), and --OH; R1 and R2 are independently selected from the group consisting of hydrogen, alkyl, halogen, --OZ, --NO2, --NH2 and --NHZ; R3 is selected from the group consisting of hydrogen, halogen, alkyl, --OZ and --NHZ; R4 is selected from the group consisting of hydrogen, halogen, alkyl, hydroxyl, hydroxyl-O-sulfate and --OZ; R5 is selected from the group consisting of hydroxyl, --CN, --N3, --NH2, --NHNH2, --NE1 E2, --NHE1, --NHCO(CH2)n CO2 H, --S(CH2)m CO2 H and --NHCHNHNH2 ; R6 is selected from the group consisting of hydrogen, alkyl, aralkyl, hydroxyalkyl, aminoalkyl, alkyl carboxylic acid and alkyl carboxamide; wherein n is 0 to 6, m is 1 to 6, p is 0 to 6, b is 0 to 2, Z is alkyl, aryl or aralkyl, D1 and D2 are independantly hydrogen or alkyl, E1 is alkyl or --(CH2)8 CO2 H, and E2 is alkyl, and the pharmaceutically acceptable salts, esters, amides, and prodrugs thereof. This invention also relates to methods of inhibiting the binding of E-selectin and/or P-selectin to sialyl-Lewisx or sialyl-Lewisa presented on a cell surface using said compounds and to pharmaceutically active compositions comprising compounds that inhibit the binding of E-selectin to sialyl-Lewisx and to methods of treatment of septic shock, ARDS, Crohn's disease, chronic inflammatory diseases, such as psoriasis and rheumatoid arthritis, and reperfusion injuries that occur following heart attacks, strokes and organ transplants.
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(2008/06/13)