4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid analogs having antihypertensive activity

Claim 1

A compound having the formula (I) ##STR54## and their pharmaceutically acceptable base or acid addition salts; wherein (1) --- is a single or a double bond; (2) one of R 1 is present and is (a) alkyl of from four to twenty carbons, inclusive, (b) ##STR55## wherein y is zero, one, two, three, four or five, R' is cycloalkyl of from four to twenty carbons, inclusive in a one, two or three saturated ring system, said ring consisting of from four to eight carbons inclusive, each ring unsubstituted or substituted by a straight or branched lower alkyl group, naphthyl, heteroaryl consisting of 2-, 3-, or 4-pyridyl; 1-, 2-, or 4-imidazolyl; 1-, 2-, 3-, 4-, 5-, 6-, or 7-indolyl; 2-, or 3-thienyl; 2-, or 3-furyl; or 1-, 2-, or 3-pyrazolyl, phenyl unsubstituted or substituted with of from one through five substituents selected from the group consisting of lower alkyl, halo, trifluoromethyl, hydroxy, lower alkoxy, lower alkyl acyloxy, amino, N-lower monoalkylamino, N,N-lower dialkylamino, lower thioalkyl, lower alkylsulfonyl, nitro and ##STR56## wherein R 10 is lower alkyl, phenyl unsubstituted or substituted by lower alkyl, or --NHR 11 wherein R 11 is hydrogen or lower alkyl, and R" is hydrogen, lower alkyl, cycloalkyl of from four to twenty carbons, inclusive in a one two or three saturated ring system, said ring consisting of from four to eight carbons inclusive, each ring unsubstituted or substituted by a straight or branched lower alkyl group, naphthyl, phenyl unsubstituted or substituted with of from one through five substituents selected from the group consisting of alkyl, halo, trifluoromethyl, amino, N-lower monoalkylamino, N,N-lower dialkylamino, lower thioalkyl, lower alkylsulfonyl, and nitro; (3) R 2 is (a) hydrogen, (b) halo, (c) lower alkyl, (d) R'--(CH 2 )-- x wherein x is one, two, three, four, or five and R' is independently as defined above, (e) ##STR57## wherein R' is independently as defined above, or (f) R'--CH(OH)-- wherein R' is independently as defined above; (4) R 3 is (a) R'--CH) x wherein x and R' are independently as defined above, (b) ##STR58## wherein R' and y are independendently as defined above, and R'" is lower alkyl, cycloalkyl, of from four to twenty carbons, inclusive in a one, two or three saturated ring system, said ring consisting of from four to eight carbons inclusive, each ring unsubstituted or substituted by a straight or branched lower alkyl group, naphthyl, phenyl unsubstituted or substituted with of from one to five substituents selected from the group consisting of alkyl, halo, trifluoromethyl, amino, N-lower monoalkylamino, N,N-lower dialkylamino, lower thioalkyl, lower alkylsulfonyl, and nitro; ##STR59## wherein R 5 is (i) alkyl of from one to fifteen carbons, inclusive, (ii) ##STR60## wherein R', R", and y are independently as defined above, (iv) --CH═CR 6 --R 1 wherein R 6 is hydrogen or lower alkyl and R 1 is as defined above, (v) ##STR61## wherein y, R' and R 6 are independently as defined above, (vi) R'--CH 2 -- y --O-- wherein y and R' are independently as defined above, (vii) ##STR62## wherein R', R", and y are independently as defined above, (d) ##STR63## wherein R 5 is independently as defined above; (5) R 4 is (a) --CH 2 OR 7 wherein R 7 is hydrogen, lower acyl, a lower alkyl, (b) ##STR64## wherein R 7 is independently as defined above and R 8 is hydrogen, lower alkyl, or benzyl, (c) ##STR65## (d) --C.tbd.N, (e) ##STR66## wherein R 9 is hydrogen, lower alkyl, or benzyl; and (6) n is one; with the overall proviso that R 9 cannot be hydrogen, methyl or ethyl when R 3 is R'--(CH 2 )-- x or ##STR67## wherein R 5 is R'--(CH 2 ) y O-- or ##STR68## wherein each of R', R", x, and y are as defined above.