Mercaptoacyl derivatives of 4-disubstituted prolines and 4-substituted dehydroprolines

Claim 2

A compound of the formula ##STR24## and pharmaceutically acceptable salts thereof wherein R is hydrogen or lower alkyl; R 1 is lower alkenyl, lower alkynyl, ##STR25## -(CH 2 ) m -cycloalkyl wherein said cycloalkyl ring is of 3 to 7 carbon atoms, α-naphthyl, β-naphthyl, ##STR26## wherein said --(CH 2 ) m -- bridge is attached to an available carbon atom, or ##STR27## wherein said --(CH 2 ) m bridge is attached to an available carbon atom; R 2 and R 3 are independently selected from the group consisting of hydrogen, lower alkyl, lower alkylthio, and halo substituted lower alkyl; n is zero, one or two; R 5 is hydrogen, ##STR28## p-methoxybenzyl, t-butoxycarbonyl, p-methoxybenzyloxycarbonyl, or ##STR29## R 6 is hydrogen, lower alkyl of 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, chloro, fluoro, bromo, trifluoromethyl or hydroxy; m is zero, one, two or three; X is O or S; and R 7 is lower alkyl of 1 to 6 carbons, lower alkyl substituted with one or more chloro, bromo or fluoro groups, ##STR30## --(CH 2 ) m -cycloalkyl wherein said cycloalkyl ring is of 3 to 7 carbons, ##STR31## wherein said --(CH 2 ) m -- bridge is attached to an available carbon atom, or ##STR32## wherein said --(CH 2 ) m -- bridge is attached to an available carbon atom.

Claim 3

The compound of claim 1 wherein R 1 is ##STR33## and said --(CH 2 ) m --bridge is attached to an available carbon atom; X is O or S; and m is zero, one or two.

Claim 4

The compound of claim 1 wherein R 1 is ##STR34## m is zero, one or two; and R 6 is hydrogen, methyl, methoxy, methylthio, chloro, fluoro, trifluoromethyl or hydroxy.

Claim 5

The compound of claim 3 wherein R 1 is phenyl.

Claim 6

The compound of claim 4 wherein R 5 is acetyl; R 3 is hydrogen; R 2 is methyl; and n is one.

Claim 7

The compound of claim 5, [1(S),2S]-1-[(3-acetylthio)-2-methyl-1-oxopropyl]-2,5-dihydro-4-phenyl-1H-pyrrole-2-carboxylic acid.

Claim 8

The compound of claim 4 wherein R 5 is hydrogen; R 3 is hydrogen; R 2 is methyl; and n is one.

Claim 9

The compound of claim 7, [1(S),2S]-2,5-dihydro-1-(3-mercapto-2-methyl-1-oxopropyl)-4-phenyl-1H-pyrrole-2-carboxylic acid.

Claim 10

The compound of claim 1 wherein R 1 is lower alkenyl of 2 to 5 carbons.

Claim 11

The compound of claim 9 wherein R 5 is hydrogen.

Claim 12

The compound of claim 1 wherein R 1 is lower alkynyl of 2 to 4 carbons.

Claim 13

The compound of claim 11 wherein R 5 is hydrogen.

Claim 14

The compound of claim 1 wherein R 1 is cycloalkyl of 3 to 7 carbons.

Claim 15

The compound of claim 13 wherein R 5 is hydrogen.

Claim 16

The compound of claim 2 wherein R 5 is hydrogen.

Claim 17

A composition useful for treating hypertension comprising a pharmaceutically acceptable carrier and one or more hypotensive agents of the formula ##STR35## and pharmaceutically acceptable salts thereof wherein R is hydrogen or lower alkyl; R 1 is lower alkenyl, lower alkynyl, ##STR36## --(CH 2 ) m --cycloalkyl wherein said cycloalkyl ring is of 3 to 7 carbon atoms, α-naphthyl, β-naphthyl, ##STR37## wherein said --(CH 2 ) m -- bridge is attached to an available carbon atom, or ##STR38## wherein said --(CH 2 ) m -- bridge is attached to an available carbon atom; R 2 and R 3 are independently selected from the group consisting of hydrogen, lower alky, lower alkylthio, and halo substituted lower alkyl; n is zero, one or two; R 5 is hydrogen, ##STR39## R 7 is lower alkyl of 1 to 6 carbons, lower alkyl substituted with one or more chloro, bromo or fluoro groups, --(CH 2 ) m cycloalkyl wherein said cycloalkyl ring is of 3 to 7 carbons ##STR40## wherein said --(CH 2 ) m -- bridge is attached to an available carbon atom, and ##STR41## wherein said --(CH 2 ) m -- bridge is attached to an available carbon atom; R 6 is hydrogen, lower alkyl of 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, chloro, fluoro, bromo, trifluoromethyl, or hydroxy; m is zero, one, two or three; and X is O or S.

Claim 18

A composition useful for treating hypertension comprising a pharmaceutically acceptable carrier and one or more hypotensive agents of the formula ##STR35## and pharmaceutically acceptable salts thereof wherein R is hydrogen or lower alkyl; R 1 is lower alkenyl, lower alkynyl, ##STR36## --(CH 2 ) m --cycloalkyl wherein said cycloalkyl ring is of 3 to 7 carbon atoms, α-naphthyl, β-naphthyl, ##STR37## wherein said --(CH 2 ) m -- bridge is attached to an available carbon atom, or ##STR38## wherein said --(CH 2 ) m -- bridge is attached to an available carbon atom; R 2 and R 3 are independently selected from the group consisting of hydrogen, lower alky, lower alkylthio, and halo substituted lower alkyl; n is zero, one or two; R 5 is hydrogen, ##STR39## R 7 is lower alkyl of 1 to 6 carbons, lower alkyl substituted with one or more chloro, bromo or fluoro groups, --(CH 2 ) m cycloalkyl wherein said cycloalkyl ring is of 3 to 7 carbons ##STR40## wherein said --(CH 2 ) m -- bridge is attached to an available carbon atom, and ##STR41## wherein said --(CH 2 ) m -- bridge is attached to an available carbon atom; R 6 is hydrogen, lower alkyl of 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, chloro, fluoro, bromo, trifluoromethyl, or hydroxy; m is zero, one, two or three; and X is O or S.

Claim 19

The method of alleviating hypertension which comprises administering an effective amount of the composition of claim 16.