1,4-dihydropyridine derivatives with calcium agonist and alpha1 -antagonist activity

Claim 1

Compounds having the formula: ##STR362## or a pharmaceutically acceptable salt thereof wherein Ar is ##STR363## where Z and R 5 are taken together as ##STR364## where t is 0 to 6; R 1 and R 2 independently are H, alkyl of 1-4 carbon atoms, haloalkyl of 1-4 carbon atoms, haloalkoxy of 1-4 carbon atoms, alkoxy of 1-10 carbon atoms, halogen, NO 2 , (CH 2 ) q XR 7 , XCH 2 (C 2 -C 9 alkenyl)R 7 , or XCH 2 (C 2 -C 9 alkynyl)R 7 ; provided that both R 1 and R 2 are not hydrogen except when R 5 is CO 2 R 7 or COR 7 ; R 3 independently is NO 2 , H, CN, or CONH 2 , or taken together with R 4 is ##STR365## R 4 and R 6 independently are alkyl of 1-4 carbon atoms CN, CH 2 OH, or CH 2 OCH 2 CH 2 NH 2 ; R 5 independently is CO 2 R 7 or COR 7 when R 1 and R 2 are other than (CH 2 ) q XR 7 , XCH 2 (C 2 -C 9 alkenyl)R 7 , or XCH 2 (C 2 -C 9 alkynyl)R 7 , and can also be an alkyl ester of 1-10 carbon atoms, ##STR366## NO 2 , or ##STR367## when one of R 1 or R 2 is (CH 2 ) q XR 7 , XCH 2 (C 2 -C 9 alkenyl)R 7 , or XCH 2 (C 2 -C 9 alkynyl)R 7 , or is taken together with Z as ##STR368## R 7 is selected from --(A) r --NH--Y--Ar', or ##STR369## where A is a straight or branched alkyl, alkenyl or alkynyl chain; Ar' is phenyl with one or two substituents selected from alkyl of 1-4 carbon atoms, haloalkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, halogen, and NO 2 ; 2-, 3- or 4-pyridine; 2,6-pyrimidine; ##STR370## R 8 is H or OCH 3 ; R 9 is H, halogen, NO 2 , alkoxy of 1-4 carbon atoms, or alkyl of 1-4 carbon atoms; X is O, S or NH; Y is (CH 2 ) q , (CH 2 ) n O, (CH 2 ) n NH or (CH 2 ) n S; n is independently 1, 2 or 3; p is 0 to 10; q is 0, 1 or 2 and: r is 1 to 10 provided that: (1) when R 5 is CO 2 R 7 and R 7 is ##STR371## or where R 2 is (CH 2 ) q XR 7 , then p cannot be 0; and (2) when R 5 is COR 7 , then R 7 must be ##STR372## and p must be 0.