E. R. Squibb Sons, Inc.

Frederic P Hauck

Joseph E Sundeen

Joyce Reid

Christopher M Cimarusti

Venkatachala L Narayanan

Rita T Fox

Michael E Condon

Rudiger D Haugwitz

Glenn A Jacobs

John R Watrous

Tamara Dejneka

Raymond R Pilote

Jeremiah J O'Connor

Frank L Weisenborn

Vinayak V Kane

Compounds are provided having the structure ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and are hydrogen, lower alkyl, lower alkenyl, or hydroxylower alkyl, or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached also form a heterocyclic radical which may contain another heteroatom, namely nitrogen, oxygen or sulfur; R.sup.3 and R.sup.4 may be the same or different and are hydrogen or lower alkyl. These compounds are useful in the treatment of arrhythmia. In addition, novel intermediates are provided having the structure ##STR2## wherein R is hydrogen, benzyl or ##STR3## These intermediates are also useful in treating acute myocardial infarction.

Antiarrhythmic tetrahydronaphthalene derivatives

Compounds having the formula ##STR1## and the pharmaceutically acceptable salts thereof, wherein n is 1 or 2; m is 2, 3 or 4; and R.sub.2 is a tertiary amino group; are intermediates useful in the preparation of compounds having hypotensive activity.

Benzo-cyclitolamines

Compounds are provided having the structure ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and are hydrogen, lower alkyl, lower alkenyl, or hydroxy-lower alkyl, or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached also form a heterocyclic radical which may contain another heteroatom, namely nitrogen, oxygen or sulfur; R.sup.3 and R.sup.4 may be the same or different and are hydrogen or lower alkyl. These compounds are useful in the treatment or arrhythmia. In addition, novel intermediates are provided having the structure ##STR2## wherein R is hydrogen, benzyl or ##STR3## These intermediates are also useful in treating acute myocardial infarction.

Pharmaceutical compositions containing 1-aryl-5-(2-propenylamino)-1-penten-3-ones and salts thereof having the structure ##STR1## wherein R.sup.1 is hydrogen, lower alkyl, lower alkoxy, halogen, hydroxy, lower alkanoyloxy, nitro, cyano, amino, carboxy or lower alkoxycarbonyl, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same or different and are hydrogen or lower alkyl. These compositions are useful in treating inflammatory conditions.

Compositions containing 1-aryl-5-(2-propenylamino)-1-penten-3-ones and

Acetamide derivatives are provided having the structure ##STR1## wherein X is a single bond, --CH.sub.2 -- or --O--, R.sup.1 and R.sup.2 may be the same or different and are lower alkyl, phenyl-lower alkoxy-lower alkyl, lower alkenyl, phenyl-lower alkyl or lower alkoxy, or ##STR2## may be taken together to form a 5- to 7-membered heterocyclic ring optionally containing one other hetero atom, such as nitrogen, sulfur or oxygen; Y is hydroxyl, OR wherein R is lower alkyl, lower alkenyl or lower alkanoyl, or ##STR3## wherein R.sup.1 and R.sup.2, and R.sup.1 and R.sup.2 taken together with the nitrogen to which they are attached are as defined above, and n is 1 to 6. These compounds are useful as anti-arrhythmia agents and have been found to be effective in the treatment of acute myocardial infarction.

Anti-arrhythmia agents

5,6,7,8-Tetrahydronaphthalenes having the structure ##STR1## and the pharmaceutically acceptable salts thereof, are useful as blood pressure lowering agents. In the above formula R.sub.1 can be hydrogen or alkyl; R.sub.2 is alkyl; R.sub.3 and R.sub.4 can each be hydrogen, hydroxyl, alkoxy, or arylalkoxy, but both cannot be hydroxyl. Those compounds wherein at least one of R.sub.3 and R.sub.4 is other than hydrogen are novel, and constitute a part of this invention.

5,6,7,8-Tetrahydronaphthalene hypotensive agents

Morpholinyl acetamide derivatives are provided having the structure ##STR1## wherein R is hydrogen, lower alkyl, lower alkenyl or lower alkanoyl, R.sup.1 and R.sup.2 may be the same or different and are lower alkyl, lower alkenyl, phenyl-lower alkyl or lower alkoxy, or ##STR2## may be taken together to form a 5- to 7-membered heterocyclic ring optionally containing one other hetero atom, such as nitrogen, sulfur or oxygen; Y is hydroxyl, OR wherein R is as defined above, or ##STR3## wherein R.sup.1 and R.sup.2 and R.sup.1 and R.sup.2 taken together with the nitrogen to which they are attached are as defined above, and n is 1 to 6.

Morpholinyl acetamide derivatives and use thereof

6-[(Aryloxy)methyl]-2-morpholinemethanol derivatives are provided having the structure ##STR1## wherein R is hydrogen, lower alkyl, phenyl-lower alkyl, or lower alkenyl, and Ar represents a monocyclic or polycyclic aromatic group including tetraindiols and their analogs. These compounds are useful as adrenergic modifiers, particularly in treating arrhythmia.

6-[(Aryloxy)methyl]-2-morpholinemethanol derivatives and use thereof

The rate of growth and feed efficiency of ruminants is increased by adding to the feed of ruminants an effective amount of the trichloroethyl ester of an essential amino acid.

Ruminant feeds containing trichloroethyl esters of essential amino acids

5-Phenyl-2,4-pentadien-1-amines and salts thereof are provided having the structure ##STR1## wherein R.sup.1 is hydrogen, lower alkyl, lower alkoxy, hydroxy, lower alkanoyloxy, nitro, cyano, amino, carboxy or lower alkoxycarbonyl, and R.sup.2 and R.sup.3 are the same or different and are hydrogen, lower alkyl, alkenyl-lower alkyl, aralkyl, and substituted lower alkyl. These compounds possess useful pharmceutical activites due to their ability to inhibit the prostaglandin-inactivating enzyme 15-.alpha.-hydroxyprostaglandin dehydrogenase.

5-Phenyl-2,4-pentadien-1-amines and method for inhibiting prostaglandin

Compounds are provided having the structure ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is hydrogen or acyl and R.sub.5 is hydrogen or acyl, X is a straight or branched bivalent alkylene radical and Y is ##STR2## These compounds are useful in the treatment of hypertension.

Hypotensive perhydro naphthalene pentol derivatives

Compounds are provided having the structure ##STR1## wherein n is 1, 2 or 3, m is 0, 1 or 2, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 may be the same or different and can be hydrogen, lower alkyl, halo-lower alkyl, acyl, lower alkoxy-carbonyl ##STR2## amido ##STR3## or lower alkoxyalkylene, X is a straight or branched bivalent aliphatic radical and Y is ##STR4## These compounds are useful in the treatment of hypertension.

Precursors of indanpentol derivatives

Compounds having the formula ##STR1## and the pharmaceutically acceptable salts thereof, wherein R.sub.1 is alkanoyl; R.sub.2 is ##STR2## AND N IS 0, 1 OR 2; HAVE USEFUL HYPOTENSIVE PROPERTIES.

Substituted 3,6-dihydro-1(2H)-pyridinylpropanols

Compounds having the formula ##STR1## wherein R.sub.1 is alkanoyl; and one of R.sub.2, R.sub.3 and R.sub.4 is ##STR2## wherein R.sub.5 is alkyl, and the other groups are --CH.sub.2 --; have useful hypotensive activity.

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Somerville, NJ, United States of America

Frederic P Hauck