Spiro-substituted glutaramide diuretic agents

Details Spiro-substituted glutaramide diuretic agents Spiro-substituted glutaramide diuretic agents

C - Chemistry, Metallurgy

07

C

167/179, 260/295

C07C 235/82 (2006.01) A61K 31/215 (2006.01) C07D 209/46 (2006.01) C07D 213/56 (2006.01) C07D 241/12 (2006.01) C07D 261/10 (2006.01) C07D 277/36 (2006.01) C07D 277/46 (2006.01) C07D 295/185 (2006.01) C07D 307/16 (2006.01) C07D 307/68 (2006.01) C07D 321/08 (2006.01) C07D 333/34 (2006.01) C07D 521/00 (2006.01)

Patent

CA 1328264

Abstract "Spiro-Substituted Glutaramide Diuretic Agents" Compounds of the formula Image (I) wherein A completes a 4 to 7 membered carbocyclic ring which may be saturated or mono-unsaturated and which may optionally be fused to a further saturated or unsaturated 5 or 6 membered carbocyclic ring; B is (CH2)m wherein m is an integer of from 1 to 3; each of R and R4 is independently H, C1-C5 alkyl, benzyl or an alternative biolabile ester-forming group; R1 is H or C1-C4 alkyl; R2 and R3 are each independently H, OH, C1-C4 alkyl or C1-C4 alkoxy; and R5 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, aryl(C2-C6 alkynyl), C3-C7 cycloalkyl, C3-C7 cycloalkenyl, C1-C6 alkoxy, -NR6R7, -NR8COR9, -NR9SO2R9 or a saturated heterocyclic group; or C1-C6 alkyl substituted by one or more substituents chosen from halo, hydroxy, C1-C6 alkoxy, C2-C6 hydroxyalkoxy, C1-C6 alkoxy (C1-C6 alkoxy), C3-C7 cycloalkyl, C3-C7 cycloalkenyl, aryl, aryloxy, aryloxy(C1-C4 alkoxy), heterocyclyl, heterocyclyloxy, -NR6R7, -NR8COR9, -NR8SO2R9, -CONR6R7, -SH, -S(O)pR10, -COR11 or -CO2R12; wherein R6 and R7 are 2 each independently H, C1-C4 alkyl, C3-C7 cycloalkyl (optionally substituted by hydroxy or C1-C4 alkoxy), aryl, aryl(C1-C4 alkyl), C2-C6 alkoxyalkyl, or heterocyclyl; or the two groups R6 and R are taken together with the nitrogen to which they are attached to form a pyrrolidinyl, piperidino, morpholino, piperazinyl or N-(C1-C4 alkyl)piperazinyl group; R8 is H or C1-C4 alkyl; R9 is C1-C4 alkyl, CF3, aryl, aryl(C1-C4 alkyl), aryl(C1-C4 alkoxy), heterocycyl, C1-C4 alkoxy or NR6R7 wherein R6 and R7 are as previously defined; R10 is C1-C4 alkyl, aryl, heterocyclyl or NR6R7 wherein R6 and R7 are as previously defined; R11 is C1-C4 alkyl, C3-C7 cycloalkyl, aryl or heterocyclyl; R12 is H or C1-C4 alkyl; and p is 0, 1 or 2; and pharmaceutically acceptable salts thereof and bioprecursors therefor are diuretic agents having utility in the treatment of hypertension, heart failure, renal insufficiency and in other disorders.

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