Cycloalkyl-substituted glutaramide antihypertensive agents

Details Cycloalkyl-substituted glutaramide antihypertensive agents Cycloalkyl-substituted glutaramide antihypertensive agents

C - Chemistry, Metallurgy

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C07C 237/24 (2006.01) A61K 31/19 (2006.01) A61K 31/215 (2006.01) C07C 233/65 (2006.01) C07C 235/82 (2006.01) C07C 271/22 (2006.01) C07C 271/24 (2006.01) C07C 311/06 (2006.01) C07C 311/08 (2006.01) C07C 311/19 (2006.01) C07D 207/08 (2006.01) C07D 207/16 (2006.01) C07D 209/18 (2006.01) C07D 209/20 (2006.01) C07D 213/82 (2006.01) C07D 231/56 (2006.01) C07D 233/54 (2006.01) C07D 307/68 (2006.01) C07D 317/40 (2006.01) C07D 521/00 (2006.01) C07F 7/08 (2006.01)

Patent

CA 1341046

Compounds of the formula: (see formula I) Wherein A completes a 5 or 6 membered carbocyclic ring which may be saturated or monounsaturated; R1 is H or (C1-C4)alkyl; R and R4 are H, (C1-C6)alkyl, C3-C7 cycloalkyl, benzyl, or an alternative biolabile ester-forming group; Y is either a direct bond or an alkylene group or from 1 to 6 carbon atoms; R2 is H, aryl, heterocyclyl, R6CONR5-, R7NR5CO-, R7NR5SO2- or ~ R3SO2NR5-, with the proviso that Y is not a direct bond when R2 is H, aryl or heterocyclyl; wherein R5 is H, (C1-C6)alkyl or aryl(C1-C6)alkyl; R6 is (C1-C6)alkyl, aryl, aryl(C1-C6)alkyl, heterocyclyl, heterocyclyl(C1-C6)alkyl or a group of the formula R9R10R11C- wherein R9 is H, OH, (C1-C6)alkoxy, (C1-C6)alkyl, hydroxy(C1-6)alkyl, aryl(C1-C6)alkyl, (C2-C6)alkynyl,~ heterocyclyl, heterocyclyl(C1-C6)alkyl, R12CONH-, R12SO2NH- or (R13)2N-; R10 and R11 are H or (C1-C6)alkyl; or R10 is H and R11 is amino (C1-C6)alkyl, imidazolylmethyl, aryl, aryl(C1-C6)alkyl, aryl(C1-C6)alkoxy(C1-C6)alkoxy, hydroxy(C1-C6)alkyl or me:thylthio(C1-C6)alkyl; or the two groups R10 and R11 form a 3 to 6 membered carbocyclic ring or a pyrrolidine or piperidine ring which may optionally be substituted by amino, (C2-C4)alkanoyl or aroyl; R12 is (C1-C6)alkyl, (C3-C7)cycloalkyl, aryl, aryl(C1-C6)alkyl, heterocyclyl or heterocyclyl(C1-C6)alkyl; each R13 is H, (C1-C6)alkyl, aryl(C1-C6)alkyl or the two groups R13 form a pyrrolidinyl, piperidino, morpholino, piperazinyl or N-(C1-C4)alkyl-piperazinyl group; R7 is (C1-C6)alkyl, aryl, aryl(C1-C6)alkyl, heterocyclyl, heterocyclyl(C1-C6)alkyl or a group of the formula R10R11R14C- wherein R10 and R11 are as previously defined and R14 is (R13)2NCO-, R12OCHG- or F15OCO, wherein R12 and R13 are as previously defined and R15 is (C1-C6)alkyl, (C3-C7)cycloalkyl or aryl(C1-C6)alkyl; and R8 is (C1-C6)alkyl, aryl, aryl(C1-C6)alkyl, heterocyclyl or heterocy clyl(C1-C5)alkyl; R3 is a group of the formula: Image wherein R16 is H, halo, 4-OH, 4-(C1-C6 alkoxy), 4-(C3-C7 cycloalkoxy) 4-(C2-C6 alkenyloxy), 4-[(C1-C6 alkoxy)carbonyloxy), 4-[(C3-C7 cycloalkoxy)carbenyloxe], or 3-(C1-C4 alkyl)SO2NH-; and R20 is H, C1-C4 alkyl, C1-C4 alkoxy, C2-C6 alkanoyl or halo; or R3 is a group of the formula: Image wherein said groups may optionally be substituted in the fused benzene ring by C1-C4 alkyl, C1-C4 alkoxy, OH, halo or CF3; are antihypertensive agents of utility in the treatment of hypertension, heart failure and renal insufficiency.

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