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US 2010/0137397 A1Published application
Chemical Compounds
AssigneeAstraZeneca AB
InventorsAlan Martin Birch, Craig Johnstone, Alleyn Thomas Plowright, Iain Simpson, Paul Robert Owen Whittamore
Life of this patent
Estimating the term…
Abstract
A compound of the formula (1) or a pharmaceutically-acceptable salt: possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity such as 2 diabetes. Processes for the manufacture of compounds and pharmaceutical compositions containing them are described.
Claims15
A compound of formula (1):
- wherein:
- Z is CH or nitrogen;
- R4 and R5 together are either —S—C(R6)═C(R7)— or —C(R7)═C(R6)—S—;
- R6 and R7 are independently selected from hydrogen, halo, nitro, cyano, hydroxy, fluoromethyl, difluoromethyl, trifluoromethyl, trifluoromethoxy, carboxy, carbamoyl, (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, (1-4C)alkoxy and (1-4C)alkanoyl;
- n is 0, 1 or 2;
- R1 is independently selected from halo, nitro, cyano, hydroxy, carboxy, carbamoyl, N-(1-4C)alkylcarbamoyl, N,N-((1-4C)alkyl)2carbamoyl, sulphamoyl, N-(1-4C)alkylsulphamoyl, N,N-((1-4C)alkyl)2sulphamoyl, (1-4C)alkylS(O)b (wherein b is 0, 1, or 2), —OS(O)2(1-4C)alkyl, (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, (1-4C)alkoxy, (1-4C)alkanoyl, (1-4C)alkanoyloxy, hydroxy(1-4C)alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, trifluoromethoxy and —NHSO2(1-4C)alkyl;
- or, when n is 2, the two R1 groups, together with the carbon atoms to which they are attached, may form a 4 to 7 membered saturated ring, optionally containing 1 or 2 heteroatoms independently selected from O, S and N, and optionally being substituted by one or two methyl groups;
- Z1 is either
- a) of the formula —Y—COOH wherein Y is (1-6C)alkylene or (3-6C)cycloalkylene;
- or
- b) of the formula —Y—COOH wherein Y is (1-6C)alkylene which is:
- i) interrupted by one heteroatom selected from —N(R7)—, —O—, —S—, —SO— and —SO2— (provided that the heteroatom is not adjacent to the carboxy group and wherein R7 is hydrogen, (1-4C)alkyl, (1-4C)alkanoyl or (1-4C)alkylsulphonyl);
- and/or
- ii) substituted on carbon by 1 or 2 substituents independently selected from cyano, oxo, hydroxyl, (1-3C)alkoxy, (1-3C)alkanoyl, (1-3C)alkoxy(2-3C)alkoxy, hydroxy(1-3C)alkyl, hydroxy(2-3C)alkoxy, (3-6C)cycloalkyl, (3-6C)cycloalkyl(1-3C)alkyl, (3-6C)cycloalkyloxy, (3-6C)cycloalkyl(1-3C)alkoxy, (1-3C)alkylS(O)c (wherein c is 0, 1 or 2), —CON(R2)R3, —N(R2)COR3, —SO2N(R2)R3 and —N(R2)SO2R3 wherein R2 and R3 are independently selected from hydrogen and (1-3C)alkyl;
- or when the alkylene group is interrupted by one heteroatom it may also be optionally substituted on a carbon by 2 substituents which together with the carbon atom to which they are attached form a (3-6C)cycloalkyl ring;
- or a pharmaceutically acceptable salt thereof;
- provided the compound is not
- (+/−)-trans-(-2-{[(2-chloro-6H-thieno[2,3-b]pyrrol-5-yl)carbonyl]amino}-2,3-dihydro-1H-inden-1-yl)acetic acid.
15 more elements
11-15. (canceled)
Dependencies are inferred from the claim text.