N-biphenyl substituted denitrogen heterocyclic derivative, its production and medicinal composition

PURPOSE: To obtain a novel compd. which has less toxicity and is useful for a hypertension, cardiac failure, glaucoma, diabetic retinal disease, etc. CONSTITUTION: A compd. of formula I [R 1 , R 2 are H, CO 2 N=C (NH 2 ) 2 .CONHNHNONH 2 , etc.; R 3 is H, a (halogen substd.) 1 to 6C alkyl, a 2 to 6C alkenyl, a 3 to 7C cycloalkyl, etc.; R 4 , R 5 are each a 1 to 6C alkyl, a 3 to 7C cycloalkyl, phenyl, etc.; X is O, S; (z), (t) are 0, 1]. For example, 2-nbutyl1-[(2'(5-oxo1,2,4oxadizol3-yl)biphenyl4-yl)methyl]4spirocyclopentane2- imidazolin5-one. The compd. of formula I is obtd. by reaction a compd. of formula IV obtd. by brining a compd. of formula II and a compd. of formula III (Hal is a halogen; R' 1 , R' 2 are respectively the precursors of R 1 , R 2 ) into reaction with a Lawesson's reagent to convert R' 1 , R' 2 to R 1 , R 2 . COPYRIGHT: (C)1993,JPO