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US 4,374,131 AGranted
Amino and substituted amino phosphinyl-alkanoyl compounds
AssigneeE. R. Squibb & Sons, Inc.
InventorEdward W. Petrillo, Jr.
Life of this patent
Estimating the term…
Abstract
Compounds of the formula ##STR1## wherein X is an imino acid or ester and R.sub.1 is hydrogen, ##STR2## are useful hypotensive agents due to their angiotensin converting enzyme inhibition activity.
Claims37
A compound of the formula ##STR254## wherein X is an imino acid of the formula ##STR255## R.sub.7 is hydrogen, lower alkyl, halogen, keto, hydroxy, ##STR256## R.sub.8 is keto, halogen, ##STR257## R.sub.9 is keto or ##STR258## R.sub.10 is halogen or --Y--R.sub.16 ;
- R.sub.11, R.sub.11 ', R.sub.12 and R.sub.12 ' are independently selected from hydrogen and lower alkyl or R.sub.11 ', R.sub.12 and R.sub.12 ' are hydrogen and R.sub.11 is ##STR259## R.sub.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.sub.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 or three;
- p is one, two or three provided that p is more than one only if R.sub.13 or R.sub.14 is hydrogen, methyl, methoxy, chloro, or fluoro;
- R.sub.15 is hydrogen or lower alkyl of 1 to 4 carbons;
- Y is oxygen or sulfur;
- R.sub.16 is lower alkyl of 1 to 4 carbons, ##STR260## or the R.sub.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;
- n is zero or one;
- R.sub.5 is hydrogen, lower alkyl, halo substituted lower alkyl, benzyl or phenethyl;
- R.sub.3 and R.sub.6 are independently selected from hydrogen, lower alkyl, benzyl, benzhydryl, or ##STR261## wherein R.sub.17 is hydrogen, lower alkyl, or phenyl, and R.sub.18 is hydrogen, lower alkyl, lower alkoxy, phenyl, or R.sub.17 and R.sub.18 taken together are --(CH.sub.2).sub.2 --, --(CH.sub.2).sub.3 --, --CH.dbd.CH--, or ##STR262## R.sub.1 is hydrogen, ##STR263## R.sub.19 is hydrogen, lower alkyl, halo substituted lower alkyl, amino substituted lower alkyl, ##STR264## wherein R.sub.13 and p are as defined above and q is zero or an integer from 1 to 7, cycloalkyl, ##STR265## R.sub.20 is lower alkyl, phenyl, benzyl or phenethyl;
- R.sub.21 is lower alkyl, benzyl or phenethyl;
- R.sub.22 is hydrogen, lower alkyl, benzyl or phenethyl;
- R.sub.2 is hydrogen, lower alkyl, lower alkenyl, halo substituted lower alkyl, ##STR266## wherein q, R.sub.13, p and m are as defined above;
- and when either or both of R.sub.3 and R.sub.6 are hydrogen a basic addition salt or an amino acid addition salt thereof.
11 more elements
Dependencies are inferred from the claim text.