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US 4,316,905 AGranted
Mercaptoacyl derivatives of various 4-substituted prolines
AssigneeE. R. Squibb & Sons, Inc.
InventorJohn Krapcho
Life of this patent
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Abstract
This invention is directed to compounds of the formula ##STR1## and various intermediates therefore. The final products possess useful hypotensive activity.
Claims37
A compound of the formula ##STR29## including a salt thereof wherein R is hydrogen or lower alkyl;
- R.sub.1 is --(CH.sub.2).sub.m -cycloalkyl wherein cycloalkyl is a saturated ring of 3 to 7 carbons, 1-cyclohexenyl, 1,4-cyclohexadienyl, ##STR30## --(CH.sub.2).sub.m -(.alpha.-naphthyl), --(CH.sub.2).sub.m -(.beta.-naphthyl), ##STR31## or ##STR32## R.sub.2 and R.sub.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.sub.4 is hydrogen, ##STR33## p-methoxybenzyloxycarbonyl, t-butoxycarbonyl, or ##STR34## m is zero, one, two or three;
- R.sub.5 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, phenyloxy, phenylthio, or phenylmethyl;
- q is one, two or three provided that q is more than one only if R.sub.5 is hydrogen, methyl, methoxy, chloro, or fluoro;
- R.sub.6 is lower alkyl, halo substituted lower alkyl, --(CH.sub.2).sub.m -cycloalkyl wherein cycloalkyl is a saturated ring of 3 to 7 carbons, ##STR35## wherein m, q, and R.sub.5 are as defined above;
- and X is oxygen or sulfur.
4 more elements
A compound of the formula ##STR38## wherein R is hydrogen or lower alkyl;
- R.sub.1 is --(CH.sub.2).sub.m -cycloalkyl wherein cycloalkyl is a saturated ring of 3 to 7 carbons, 1-cyclohexenyl, 1,4-cyclohexadienyl, ##STR39## --(CH.sub.2).sub.m -(.alpha.-naphthyl), --(CH.sub.2).sub.m -(.beta.-naphthyl), ##STR40## m is zero, one, two or three;
- R.sub.5 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, phenyloxy, phenylthio, or phenylmethyl;
- q is one, two or three provided that q is more than one only if R.sub.5 is hydrogen, methyl, methoxy, chloro, or fluoro;
- and
- X is oxygen or sulfur.
2 more elements
A composition useful for treating hypertension comprising a pharmaceutically acceptable carrier and an effective amount of a hypotensive agent of the formula ##STR42## including a pharmaceutically acceptable salt thereof wherein R is hydrogen or lower alkyl;
- R.sub.1 is (CH.sub.2).sub.m -cycloalkyl wherein cycloalkyl is a saturated ring of 3 to 7 carbons, 1-cyclohexenyl, 1,4-cyclohexadienyl, ##STR43## --(CH.sub.2).sub.m -(.alpha.-naphthyl), --(CH.sub.2).sub.m -(.beta.-naphthyl), ##STR44## R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, lower alkyl, lower alkylthio, and halo substituted lower alkyl;
- R.sub.4 is hydrogen, ##STR45## or ##STR46## R.sub.5 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, phenyloxy, phenylthio or phenylmethyl;
- m is zero, one, two or three;
- q is one, two or three provided that q is more than one only if R.sub.5 is hydrogen, methyl, methoxy, chloro or fluoro;
- R.sub.6 is lower alkyl of 1 to 6 carbons, halo substituted lower alkyl of 1 to 6 carbons, --(CH.sub.2).sub.m -cycloalkyl wherein cycloalkyl is as defined above, ##STR47## X is oxygen or sulfur.
2 more elements
Dependencies are inferred from the claim text.