Miles Laboratories, Inc.

Robert N Schut

Max E Safdy

Enrique Hong

Michael P Kotick

David L Leland

John W Van Dyke, Jr

Joseph O Polazzi

Edgar O Snoke

Harold Eugene Hartzler

Disclosed is the novel compound methyl 3-acetamido-2-(5-methoxyindol-3-yl) propanoate which is useful as an anti-hypertensive agent.

Methyl 3-acetamido-2-(5-methoxy-indol-3-yl) propanoate and hypotensive

Disclosed are compounds characterized by the structural formula: ##STR1## Various compounds circumscribed by the foregoing formula in which: R is H, CH.sub.3 or CH.sub.2 CH.sub.3,

3-Amino or amido-2-(1H-indol-3-yl) propanoic acid derivatives

The compounds having Formula I, ##STR1## wherein X is a fluorine or methoxy group, and R is a hydrogen or methyl group, such that R is hydrogen only when X is fluorine are novel. The compounds having Formula I and their acid addition salts are useful for the treatment of hypertension. Processes for the preparation of the compounds having Formula I and useful intermediates are described.

Process for the preparation of 3-amino-2-(5-fluoro and

Disclosed are 7,8 and 7-8 substituted 4,5.alpha.-epoxymorphinan-6-one compounds characterized by the structural formula: ##STR1## In the foregoing formula R.sub.1 may be H or methyl, R.sub.2 is cyclopropylmethyl, cyclobutylmethyl, allyl or tetrahydrofurfuryl, R.sub.3 is H, .beta.-methyl, .beta.-ethyl or .alpha.-ethyl and R.sub.4 is H or .alpha.-methyl. Particular compounds corresponding to the foregoing description are useful as mixed analgesics/narcotic antagonists whereas others have been found to be pure narcotic antagonists.

7,8 and 7-8 Substituted 4,5.alpha.-epoxymorphinan-6-one compounds, and

Disclosed are novel isoquinoline propionamides and their acid salts represented by the structural formula: ##STR1## wherein R is alkyl of 1 to 6 carbon atoms, methylcycloalkyl of 4 to 7 carbon atoms or alkaryl of 7 to 8 carbon atoms;

Isoquinoline propionamides exhibiting analgesic properties

Disclosed are 7-methyl, 8.beta.-lower alkyl and 7 methyl-8-lower alkyl substituted B/C Cis or Trans morphinan-6-one compounds characterized by the structural formula: ##STR1## Specific compounds, included within the scope of the foregoing general formula wherein R.sub.1 is H or methyl, R.sub.2 is cyclopropylmethyl or cyclobutylmethyl, R.sub.3 is H, methyl, ethyl or n-propyl and R.sub.4 is H or methyl are useful as mixed analgesics/narcotic antagonists.

7-Methyl-8.beta.-lower alkyl or 7-methyl-8-lower alkyl B/C cis or trans

Novel 3-substituted salicylamides having increased analgesic activity and prolonged analgesic activity are disclosed.

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Edwardsburg, MI, United States of America

Robert N Schut