Substituted 4-phenoxy or 4-phenylthio prolines

A compound of the formula ##STR107## and a pharmaceutically acceptable salt thereof wherein

• X is oxygen or sulfur;
• --A.sub.1 -A.sub.2 -- is --CH--NH-- or --C.dbd.N--;
• A is ##STR108## p is one, two, three or four;
• R, R.sub.8 and R.sub.9 are independently selected from the group consisting of hydrogen, lower alkyl, benzyl, benzhydryl, and salt forming ion;
• R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, halo substituted lower alkyl, nitro, and --SO.sub.2 NH.sub.2 ;
• Z is ##STR109## R.sub.3 is hydrogen, lower alkyl, halo substituted lower alkyl, phenyl, benzyl, phenethyl or cycloalkyl;
• R.sub.4 is hydrogen or ##STR110## R.sub.5 is lower alkyl, ##STR111## n is zero, one, two, three or four;
• R.sub.6 is hydrogen, lower alkyl, lower alkoxy, halogen, or hydroxy;
• R.sub.7 is lower alkyl or cycloalkyl;
• R.sub.10 is hydrogen, lower alkyl, ##STR112## halo substituted lower alkyl, hydroxy substituted lower alkyl, --(CH.sub.2).sub.q -cycloalkyl, --(CH.sub.2).sub.q -N(lower alkyl).sub.2, --(CH.sub.2).sub.q --NH.sub.2, --(CH.sub.2).sub.q -carboxy, --(CH.sub.2).sub.q --SH, --(CH.sub.2).sub.q -S-lower alkyl, ##STR113## q is one, two, three or four;
• R.sub.11 is hydrogen, lower alkyl, halo substituted lower alkyl, hydroxy substituted lower alkyl, --(CH.sub.2).sub.q --NH.sub.2, --(CH.sub.2).sub.q -N(lower alkyl).sub.2, --(CH.sub.2).sub.q -quanidinyl, ##STR114## R.sub.12 is alkyl of 1 to 10 carbons, ##STR115## cycloalkyl--(CH.sub.2).sub.m --;
• m is zero or an integer from 1 to 7;
• R.sub.13 is hydrogen, lower alkyl, benzyl, benzhydryl, salt forming ion or ##STR116## R.sub.15 is hydrogen, lower alkyl, cycloalkyl or phenyl;
• p0 R.sub.16 is hydrogen, lower alkyl, lower alkoxy, cycloalkyl, phenyl, benzyl, or phenethyl;
• and
• R.sub.14 is hydrogen, lower alkyl, cycloalkyl-(CH.sub.2).sub.n --, ##STR117## halo substituted lower alkyl, hydroxy substituted lower alkyl, --(CH.sub.2).sub.q --N(lower alkyl).sub.2, or --(CH.sub.2).sub.q --NH.sub.2.