Hydroxy substituted peptide compounds

Claim 1

A compound of the formula ##STR206## or a pharmaceutically acceptable salt thereof wherein X is ##STR207## R is hydrogen, lower alkyl, cycloalkyl, ##STR208## R 1 is hydrogen, lower alkyl, halo substituted lower alkyl, ##STR209## R 2 is ##STR210## R 3 is hydrogen, lower alkyl, ##STR211## R 4 is hydrogen, lower alkyl, ##STR212## R 5 is hydrogen, lower alkyl, ##STR213## r is an integer from 1 to 4; R 7 is hydrogen, lower alkyl, halogen, hydroxy, ##STR214## a 1- or 2-naphthyl of the formula ##STR215## a 1- or 2-naphthyloxy of the formula ##STR216## R 8 is halogen, ##STR217## --O-lower alkyl, a 1- or 2-naphthyloxy of the formula ##STR218## or a 1- or 2-naphthylthio of the formula ##STR219## R 9 is keto or ##STR220## R 10 is halogen or --Y-R 16 ; R 11 , R 11 ', R 12 and R 12 ' are independently selected from hydrogen and lower alkyl or R 11 ', R 12 and R 12 ' are hydrogen and R 11 is ##STR221## R 13 is hydrogen, lower alkyl of 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, chloro, bromo, fluoro, trifluoromethyl, hydroxy, phenyl, phenoxy, phenylthio, or phenylmethyl; R 14 is hydrogen, lower alkyl of 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, chloro, bromo, fluoro, trifluoromethyl, or hydroxy; m is zero, one, two, three, or four; p is one, two or three provided that p is more than one only if R 13 or R 14 is hydrogen, methyl, methoxy, chloro, or fluoro; R 15 is hydrogen or lower alkyl of 1 to 4 carbons; Y is oxygen or sulfur; R 16 is lower alkyl of 1 to 4 carbons, ##STR222## or the R 16 groups join to complete an unsubstituted 5- or 6-membered ring or said ring in which one or more of the carbons has a lower alkyl of 1 to 4 carbons or a di(lower alkyl of 1 to 4 carbons) substituent; R 19 is lower alkyl, benzyl, or phenethyl; R 20 is hydrogen, lower alkyl, benzyl or phenethyl; R 6 is hydrogen, lower alkyl, benzyl, benzhydryl, ##STR223## R 17 is hydrogen, lower alkyl, cycloalkyl or phenyl; R 18 is hydrogen, lower alkyl, lower alkoxy, phenyl, or R 17 and R 18 taken together are ##STR224## R 24 is hydrogen, lower alkyl, ##STR225## R 21 and R 22 are independently selected from the group consisting of hydrogen and lower alkyl; and R 23 is lower alkyl.