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35370-80-0

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Dihydrothiazolopyridone derivatives as a novel family of positive allosteric modulators of the metabotropic glutamate 5 (mGlu5) receptor
Starting from a singleton chromanone high throughput screening (HTS) hit, we describe a focused medicinal chemistry optimization effort leading to the identification of a novel series of phenoxymethyl-dihydrothiazolopyridone derivatives as selective positive allosteric modulators (PAMs) of the metabotropic glutamate 5 (mGlu5) receptor. These dihydrothiazolopyridones potentiate receptor responses in recombinant systems. In vitro and in vivo drug metabolism and pharmacokinetic (DMPK) evaluation allowed us to select compound 16a for its assessment in a preclinical animal screen of possible antipsychotic activity. 16a was able to reverse amphetamine-induced hyperlocomotion in rats in a dose-dependent manner without showing any significant motor impairment or overt neurological side effects at comparable doses. Evolution of our medicinal chemistry program, structure activity, and properties relationships (SAR and SPR) analysis as well as a detailed profile for optimized mGlu5 receptor PAM 16a are described.
Bartolomé-Nebreda, José Manuel,Conde-Ceide, Susana,Delgado, Francisca,Iturrino, Laura,Pastor, Joaquín,Pena, Miguel ángel,Trabanco, Andrés A.,Tresadern, Gary,Wassvik, Carola M.,Stauffer, Shaun R.,Jadhav, Satyawan,Gogi, Kiran,Vinson, Paige N.,Noetzel, Meredith J.,Days, Emily,Weaver, C. David,Lindsley, Craig W.,Niswender, Colleen M.,Jones, Carrie K.,Conn, P. Jeffrey,Rombouts, Frederik,Lavreysen, Hilde,Macdonald, Gregor J.,Mackie, Claire,Steckler, Thomas
p. 7243 - 7259
(2013/10/21)

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Chemical Properties

Melting Point: 114-116 °C
Boiling Point: 302.9 °C at 760 mmHg
Flash Point:137 °C
Density: 1.206 g/cm³
Vapor Pressure: 0.000962mmHg at 25°C
Refractive Index: 1.615
PSA: 67.34000
LogP: 2.05180

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