Muscarinic antagonists

A compound according to the structural formula I, ##STR169## including all isomers and pharmaceutically acceptable salts, esters, and solvates thereof,

• wherein Y and Z are each N;
• X is --O--, --S--, --SO--, --SO.sub.2 --, --NR.sup.6 --, --CO--, --CH.sub.2 --, --CS--, --C(OR.sup.5).sub.2 --, --C(SR.sup.5).sub.2 --, --CONR.sup.20 --, --C(alkyl).sub.2 -, --C(H)(alkyl)-, --NR.sup.20 --SO.sub.2 --, --NR.sup.20 CO--, ##STR170## --O--CO--NH--, or --NH--CO--O--R is ##STR171## (wherein X.sup.1 is --CH.sub.2 --, --O--, or --NR.sup.7 --), ##STR172## hydrogen, acyl, alkyl, alkenyl, cycloalkyl, cycloalkyl substituted with up to two alkyl groups, cycloalkenyl, bicycloalkyl, arylalkenyl, benzyl, benzyl substituted with up to three independently selected R.sup.3 groups, cycloalkylalkyl, polyhaloacyl, benzyloxyalkyl, hydroxyC.sub.2 -C.sub.20 alkyl, alkenylcarbonyl, alkylarylsulfonyl, alkoxycarbonylaminoacyl, alkylsulfonyl, or arylsulfonyl, additionally, when X is --CH.sub.2 --, R may also be --OH;
• in further addition, when X is not N, R may also be hydroxymethyl, in further addition, R and X may combine to form the group Prot-(NOAA).sub.r -NH-- wherein r is an integer of 1 to 4, Prot is a nitrogen protecting group and when r is 1, NOAA is a naturally occurring amino acid or an enantiomer thereof, or when r is 2 to 4, each NOAA is an independently selected naturally occurring amino acid or an enantiomer thereof;
• R.sup.1 and R.sup.21 are independently selected from the group consisting of H, alkyl, alkenyl, cycloalkyl, cycloalkenyl, bicycloalkyl, alkynyl, cyano, aminoalkyl, alkoxycarbonyl, aminocarbonyl, Hydroxyamidino, alkoxycarbonylalkyl, phenyl alkyl, alkylcarbonlyoxyalkyl, ##STR173## H, formyl, --CO alkyl, --COacyl, --COaryl, and hydroxyalkyl;
• additionally R.sup.1 and R.sup.21 together may form the group .dbd.CH.sub.2, .dbd.N--OR.sup.5, .dbd.N--CN, .dbd.N--N(R.sup.5).sub.2, .dbd.CH-Alkyl, alkylene, .dbd.O, ##STR174## .dbd.C(halo).sub.2, in further addition, R.sup.1 and R.sup.21 together with the carbon atom to which they are attached may form the group ##STR175## or R.sup.1 and R.sup.21 together with the carbon atom to which they are attached may form a saturated heterocyclic ring containing 3 to 7 carbon atoms, one or more of which may optionally be substituted by alkyl, and one or two groups independently selected from S, O, and N--R.sup.20 ;
• R.sup.30 is H, alkyl, aryl, cycloalkyl, hydroxyalkyl, aminoalkyl, --COOR.sup.20, --CON(R.sup.20).sub.2 or cyano;
• R.sup.31 and R.sup.32 are the same as R.sup.30 and in addition, two R.sup.30, R.sup.31 and R.sup.32 groups may form the group --(CH.sub.2).sub.r --, (wherein r is 1 to 6), in further addition, R.sup.31 and R.sup.32 can also be hydroxy, --N(R.sup.20).sub.2, --O-acyl, --N(R.sup.20)acyl, --OCOOR.sup.20, or --OCON(R.sup.20).sub.2 ;
• R.sup.33 is aryl or heteroaryl, with the proviso that when R.sup.33 is heteroaryl, the CO--R.sup.33 bond is to a carbon atom in R.sup.33 ;
• and
• R.sup.34 is alkyl, cycloalkyl or aryl and in addition R.sup.34 may also be H when R.sup.1 and R.sup.21 together with the carbon atom to which they are attached form a saturated heterocyclic ring containing 3 to 7 carbon atoms and two groups independently selected from S, O, and N--R.sup.20.