E. R. Squibb Sons, Inc.

Rudiger D Haugwitz

Venkatachala L Narayanan

Larry R Cruthers

Barbara V Maurer

Joseph E Sundeen

Frederic P Hauck

Christopher M Cimarusti

Joyce Reid

Peter C Wade

Frank L Weisenborn

Peter W Sprague

Glenn A Jacobs

Hans H Gadebusch

Ravi K Varma

George C Rovnyak

Thomas P Kissick

Jack Bernstein

This invention is directed to substituted 4-phenoxy and 4-phenylthio prolines of the formula ##STR1## which possess useful hypotensive activity.

Substituted 4-phenoxy or 4-phenylthio prolines

Compounds of the formula ##STR1## are disclosed. They possess angiotensin converting enzyme inhibition activity and diuretic activity and are therefore useful as antihypertensive agents.

Antiinflammatory activity is exhibited by steroids having the formula ##STR1## or the 1,2-dehydro derivative thereof, wherein R.sub.1 is alkyl, alkanoyloxyalkyl, arylcarbonyloxyalkyl, alkenyl, alkynyl, cycloalkyl, aryl or arylalkyl;

17.beta.-(substituted thio)androstenes

Compounds having the formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently hydrogen, halogen, trifluoromethyl, aminosulfonyl, nitro, alkyl or alkoxy;

Benzothiadiazines having diuretic activity

Compounds having the formula ##STR1## wherein: R.sub.1 is hydrogen, alkyl, aryl or arylalkyl;

Dithioacyldihydropyrazole carboxylic acid derivatives

Phenylguanidine derivatives are provided having the structure ##STR1## wherein R.sup.1 is lower alkyl, cycloalkylalkyl, or phenylalkyl; R.sup.2 is lower alkyl, phenyl or benzyl; and R.sup.3 is lower alkyl, cycloalkylalkyl, lower alkenylalkyl, dihalovinylalkyl, dihalobutadienyl or phenylalkyl; and n is 1 to 5. These compounds are useful as anthelmintic agents.

Substituted phenylguanidines and method

Compounds having the formula ##STR1## wherein R.sub.1 is hydrogen, alkyl, aryl, arylalkyl or a hydrolyzable acyl protecting group;

1-Mercaptoacyl-3-[(aminosulfonyl)

Angiotensin converting enzyme inhibitory action is shown in mammals by compounds having the formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different, and each is hydrogen, halogen, trifluoromethyl, or aminosulfonyl;

Lactam derivatives of mercaptoacylamino acids

Phenylguanidine derivatives are provided having the structure ##STR1## wherein R is hydrogen, lower alkyl, cycloalkyl, lower alkoxy, phenyl, phenylalkyl, phenoxy, phenylalkoxy, lower alkoxyalkyl, phenoxyalkyl, alkylamino, dialkylaminoalkyl, alkylthio, phenylthio, phenylthioalkyl, and alkylthioalkyl; R.sup.1 is lower alkyl or benzyl; R.sup.2 is hydrogen, lower alkoxy carbonyl, and lower alkanoyl; R.sup.3 is lower alkyl, cycloalkylalkyl, lower alkenyl, lower alkynyl or benzyl; and n is 0 or 1. These compounds are useful as anthelmintic agents.

Substituted phenylguanindines and method

Dithioacylproline derivatives

Imidazolo-pyridine derivatives are provided having the structure ##STR1## wherein R is lower alkyl, lower alkenylalkyl, lower alkynylalkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl or phenylalkyl and R.sup.1 is lower alkyl, phenylalkyl or di-lower alkylaminoalkyl and n is 0, 1 or 2. These compounds are useful as anthelmintic agents administered orally or parenterally.

Substituted imidazolo-pyridines and method

Compounds having the formula ##STR1## wherein R.sub.1 and R.sub.2 are each alkyl; and R.sub.4 is hydrogen, halogen, trifluoromethyl, phenylthio, or cyano; have anthelmintic and anti-fungal activity.

Phenylene-bis (substituted thioureas)

Phenylguanidine derivatives are provided having the structure ##STR1## wherein R is lower alkyl, cycloalkyl, cycloalkylalkyl, lower alkenyl, lower alkynyl, phenyl or benzyl; R.sup.1 and R.sup.2 may be the same or different and are lower alkyl or R.sup.1 and R.sup.2 may be taken together to form an alkylene linking group of 2 or 3 carbons or an o-phenylene group; R.sup.3 and R.sup.4 are the same or different and are lower alkyl, benzyl or phenyl; and n is 0 or 1. These compounds are useful as anthelmintic agents.

Polyether derivatives are provided having the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.5 and R.sup.6 are the same or different and are hydrogen, halogen, nitro, lower alkyl or cyano; R.sup.3 and R.sup.4 are the same or different and are hydrogen, halogen or together represent .dbd.O; and n is 1 to 5. These compounds are useful as coccidiostats and anti-inflammatory agents.

Polyether derivatives

New selenium containing derivatives of proline and pipecolic acid which have the general formula ##STR1## are useful as hypotensive agents.

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Titusville, NJ, United States of America

Rudiger D Haugwitz