# US 4,396,773 A · 1,1'-[Dithiobis(2-alkyl-1-oxo-3,1-propanediyl)]-bis[2,3-dihydro-1H-indole -2-carboxylic acids and derivatives

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- Number: US 4,396,773 A
- Document ID: US4396773A
- Status: Granted
- Kind: A
- Application number: 06/306,012
- Filed: 1981-09-28
- Granted: 1983-08-02
- Earliest claimed: 1979-08-13
- Assignees: American Home Products Corporation
- Inventors: Dong H. Kim; Ronald J. McCaully
- Web page: https://patentgrep.com/patent/US4396773A

## CPC

- C07D 513/04: Ortho-condensed systems
- C07D 209/42: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Disclosed herein are N-(3-mercapto-2-alkyl-1-oxopropyl)-2,3-dihydro-1H-indole-2-carboxylic acids and derivatives thereof which act as inhibitors of angiotensin converting enzyme and as anti-hypertensive agents. Derivatives include those in which the 3-mercapto group is substituted with phosphate derivatives or is replaced by a variously substituted amino group. The compounds of the invention (excluding disclosed intermediates) have the general formula: ##STR1## wherein: n is 1 or 0; R.sub.1 is hydrogen, lower alkyl, aryl or aralkyl; R.sub.2 is hydrogen or lower alkyl; R.sub.3 is hydrogen, lower alkyl or aroyl; R.sub.5 is hydroxy, amino, or lower alkoxy; X is hydrogen, hydroxy, lower alkyl, lower alkoxy, or halogen; Y is hydrogen, lower alkyl, or aryl; R.sub.4 is -SH, ##STR2## wherein L is O, NR.sub.7 or S (where R.sub.7 is hydrogen or lower alkyl); M is R.sub.8, OR.sub.8, SR.sub.8, or NR.sub.9 R.sub.10 (where R.sub.8 is hydrogen, lower alkyl, aryl, or aralkyl; and R.sub.9 and R.sub.10 are, independently, hydrogen, lower alkyl, or aryl); A is O, NR.sub.13 or S; R.sub.11 and R.sub.12 are, independently, hydrogen, alkyl, aralkyl or aryl; R.sub.13 is hydrogen or lower alkyl; m is 0, 1, 2, or 3; R.sub.20 is hydrogen or aryl; and R.sub.21 is hydroxy or lower alkoxy; or pharmaceutically acceptable salts thereof.

## Claims

### Claim 1

A disulfide compound of the formula: ##STR15## wherein: n is 1 or 0;
R.sub.1 is hydrogen, lower alkyl, aryl, or aralkyl;
R.sub.2 is hydrogen or lower alkyl;
R.sub.3 is hydrogen, lower alkyl, or aroyl;
R.sub.5 is hydroxy, amino, or lower alkoxy;
X is hydrogen, hydroxy, lower alkyl, lower alkoxy, or halogen; and
Y is hydrogen, lower alkyl, or aryl;
or pharmaceutically acceptable salts thereof, wherein aryl is phenyl or phenyl substituted by a halogen, lower alkyl, lower alkoxy, or hydroxy group; aralkyl is benzyl or benzyl substituted on the phenyl ring by a halogen, lower alkyl, lower alkoxy, or hydroxy group; aroyl is benzoyl or benzoyl substituted as above for phenyl; and lower alkyl and lower alkoxy refer to such groups having 1-4 carbon atoms.

### Claim 2 (depends on 1)

A compound of claim 1 wherein R.sub.3 is hydrogen or lower alkyl.