Pharmaceutically active pyrazine derivatives

US9630931B2 · kind B2 · utility

Assignee

• SENTINEL ONCOLOGY LIMITED · GB

Inventors

• Robert George Boyle · Cambridge, GB
• Richard J. Boyce · Elkton, US

Key dates

• Filing date: Nov 16, 2012
• Grant date: Apr 25, 2017
• Expiry date: Nov 16, 2032

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D413/12
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The invention provides compounds which inhibit or modulate the activity of Chk-1 kinase and which are useful in the treatment of cancer. The compounds have the general formula (1):and salts, N-oxides and tautomers thereof, wherein m is 2, 3 or 4; n is 0 or 1; Q1 is selected from a bond; C(═O); S(O); SO2; and an alkylene chain of 1 to 4 carbon atoms in length between the moiety R4 and the nitrogen atom. N, wherein (a) one or more of the 1 to 4 carbon atoms of the alkylene chain may optionally be substituted with one or two C1-4 alkyl groups; and/or (b) one carbon atom of the 1 to 4 carbon atoms of the alkylene chain may optionally be replaced by a cyclopropane-1,1-diyl or 1,1-cyclobutanediyl group; and/or (c) one carbon atom of the 1 to 4 carbon atoms of the alkylene chain may optionally be replaced by C(═O), S(O), or SO2, provided that Q1 contains no more than one C(═O), S(O), or SO2 moiety; R1 is selected from hydrogen, methyl, chlorine and bromine; R2 is selected from hydrogen, methyl, methoxy and a group —(O)p-Q2-R5; R3 is selected from hydrogen, a group Hyd1, a group —O-Hyd1 and a group —(O)p-Q2-R5; provided that when one of R2 and R3 is —(O)p-Q2-R5, the other is selected from …