Pyrazine compounds

US6599905B2 · kind B2 · utility

Assignee

• SmithKline Beecham Limited · US

Inventors

• Brian Cox · Stevenage, GB
• Dean David Edney · Hatton, GB
• Michael Simon Loft · Hatton, GB
• Malcolm Stuart Nobbs · Sydenham, GB
• Gita Punjabhai Shah · Stevenage, GB

Key dates

• Filing date: May 16, 2001
• Grant date: Jul 29, 2003
• Expiry date: May 16, 2021

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D241/26
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Compounds of formula (I) where R1 is phenyl substituted by one or more halogen atoms, naphthyl and naphthyl substituted by one or more halogen atoms; R2 is —NH2 and —NHC(═O)Ra; R3 is —NRbRc, —NHC(═O)Ra or hydrogen; R4 is hydrogen, —C1-4 alkyl, —CN, —CH2OH, —CH2ORd, —CH2S(O)xRd and —C1-4 alkyl substituted by one or more halogen atoms in which Ra represents C1-4 alkyl or C3-7cycloalkyl, and Rb and Rc, which may be the same or different, are hydrogen or C1-4 alkyl, or together with the nitrogen atom to which they are attached, form a 6-membered nitrogen containing heterocycle, which heterocycle can be further substituted with one or more C1-4 alkyl; Rd is C1-4 alkyl or C1-4 alkyl substituted by one or more halogen atoms; x is an integer zero, one or two; and salts, solvates and prodrugs thereof, provided that R1 does not represent: when R2 is —NH2, and both R3 and R4 are hydrogen. The compounds are useful as analgesics, anticonvulsants, for treating bipolar disorder and as neuroprotectants.