American Cyanamid Company

Andrew S Tomcufcik

William B Wright, Jr

Walter E Meyer

John P Dusza

Joseph W Marsico, Jr

Nancy H Eudy

Howard Hancock Newman

Jay Donald Albright

Raymond G Wilkinson

Joseph W Marsico

William V Curran

Ralph G Child

Adolph E Sloboda

Adma S Ross

Lawrence W Torley

Jeffrey B Medwid

Jeffery B Press

Shin S Tseng

Peter S Chan

David L Crandall

John E Emma

Joseph William Epstein

Yang-I Lin

Robert G Lees

William J Fanshawe

Stanley A Lang, Jr

Gary H Birnberg

Martin L Sassiver

Corris M Hofmann

Paul Frank Fabio

James S Dixon

Bernard Beer

Joseph William Hinson

Joseph W Marisco, Jr

N-methyl-N-(3-&lcub;3-&lsqb;2-thienylcarbonyl&rsqb;-pyrazol-&lsqb;1,5-&agr;&rsqb;-pyrimidin-7-yl&rcub;phenyl)acetamide, and use of the same as a sedative-hypnotic, anxiolytic, anticonvulsant, and skeletal muscle relaxant agent. Compositions containing N-methyl-N-(3-&lcub;3-&lsqb;2-thienylcarbonyl&rsqb;-pyrazol-&lsqb;1,5-&agr;&rsqb;-pyrimidin-7-yl&rcub;phenyl)acetamide, as well as pharmaceutically acceptable salts thereof, are also disclosed.

N-methyl-N-(3-&lcub;3-&lsqb;2-thienylcarbonyl&rsqb;-pyrazol-&lsqb;1, 5-&agr;&rsqb;-pyrimidin-7-yl&rcub;phenyl)acetamide and compositions and methods related thereto

The present invention relates to substituted .omega.-�phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl! �alkyl, alkenyl or alkynyl!amine carboxamides, sulfonamides and phosphonylamides which are useful as antiarrhythmic agents.

N-�4-(imidazolyl or pyrazolyl)phenyl(oxy, sulfinyl, sulfenyl or

Disclosed are 3-substituted-7-[3-(imidazol-1-yl)phenyl]-pyrazolo[1,5-a]pyrimidines of the formula: ##STR1## wherein R.sup.1, R.sup.3 and R.sup.4 are defined in the specification which compounds have anxiolytic, anti-convulsant, sedative-hypnotic and skeletal muscle relaxant activity.

3-Substituted-7-[3-(imidazol-1-yl)phenyl]-pyrazolo[1,5-a]pyrimidines

Compounds of the formula: ##STR1## wherein R.sup.1, R.sup.2 and m are defined in the specification are provided. These compounds are useful as antihypertensive agents.

Substituted benz[cd]indol-2-(1H)-ones and use as antihypertensive agents

Omega-((hetero)alkyl)benz(cd)indol-2-amines useful in inhibition of thromboxane synthetase and in treatment of hypertension in warm-blooded animals are disclosed.

Omega-((hetero)alkyl)benz(cd)-indol-2-amines

N.sup.1 substituted benz [cd] indol -2(1H)-imines useful as inhibitors of Thromboxane synthetase enzyme, hypertension and arrhythmia are described.

N.sup.1 -substituted benz(cd)indol-2-imine compounds as cardiovascular

(3-Amino-1H-pyrazol-4-yl)(aryl)methanones which are new compounds having utility as intermediates for the preparation of aryl and heteroaryl-[7-(aryl and heteroaryl)pyrazolo[1,5-a]pyrimidin-3-yl]methanones, which are therapeutic agents.

Method of making (3-amino-1H-pyrazol-4-yl) (aryl)methanones

This disclosure describes novel substituted guanidinedicarbonyl derivatives which possess anxiolytic activity and are also useful as agents for the treatment of cognitive and related neural behavioral problems in mammals.

Substituted guanidinedicarbonyl derivatives

Novel 10,10-Dihydro-10-[substituted carbonyl)imino]-10-phenyl-10H-phenoxaphines of the formula: ##STR1## wherein A is selected from the group consisting of hydrogen and COOR.sub.1, where, when A is hydrogen the compound is in the form of a water soluble salt HnX, where n is an integer 1 or 2 and X is selected from the group consisting of sulfate, trefluoroacetate, bromide and chloride and R.sub.1 is selected from the group consisting of straight or branched chain alkyl(C.sub.1 -C.sub.4), alkenyl(C.sub.2 -C.sub.4), alkynyl(C.sub.2 -C.sub.4), cycloalkyl(C.sub.3 -C.sub.6), cycloalkyl(C.sub.3 -C.sub.6)methyl, benzyl, pyridylmethyl and tetrahydro-3-furanyl; methods for using these compounds for effecting diuresis, treating hypertension and edema and lowering plasma renin activity in mammals; pharmaceutical compositions of matter containing these compounds and processes for their preparation.

10,10-Dihydro-10-((

(3-Amino-1H-pyrazol-4-yl)(aryl)methanones which are new compounds having utility as intermediates for the preparation of aryl and heteroaryl[7-(aryl and heteroaryl)pyrazolo[1,5-a]pyrimidin-3-yl]methanones, which are therapeutic agents.

(3-amino-1H-pyrazol-4-yl) (aryl)methanones

Novel triarylphosphinimide derivatives having the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are each at the ortho or meta position, represent mono- or disubstituents and are selected from the group consisting of hydrogen, alkyl(C.sub.1 -C.sub.3), alkoxy(C.sub.1 -C.sub.3), trifluoromethyl and halogen; and R.sub.4 is selected from the group consisting of alkyl (C.sub.1 -C.sub.3), alkenyl(C.sub.2 -C.sub.3), alkynyl(C.sub.2 -C.sub.4), alkynyl(C.sub.2 -C.sub.4), cycloalkyl(C.sub.3 -C.sub.5), cycloalkyl(C.sub.3 -C.sub.6)methyl, 4-oxopentyl, 3-tetrahydrofuranyl, 2,3-dihydro-1H-iden-1-yl, 1-alkyl(C.sub.1 -C.sub.3)cyclopentyl, trans-2-alkyl(C.sub.1 -C.sub.3)cyclopentyl, trans-2-alkoxy(C.sub.1 -C.sub.3)cyclopentyl, 1-cyclopropylethyl, 2-methylcyclopropylmethyl, dicyclopropylmethyl, 2-, 3- or 4-pyridinylmethyl, 2-cyclopenten-1-yl, tetrahydro-2H-pyran-4-yl and cis and trans-2-methoxycyclohexyl; with the proviso that when R.sub.4 is alkyl(C.sub.1 -C.sub.3), R.sub.1, R.sub.2 and R.sub.3 may not each be hydrogen or ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are each at the ortho or meta position and are selected from hydrogen and alkyl(C.sub.1 -C.sub.3), and X is an acid addition salt; processes for producing them, compositions containing them, and methods for using them in mammals to effect diuresis; to lower plasma renin levels and to increase cardiac contractility.

Certain triphenylphosphinimide derivatives

This disclosure describes novel esters of (triarylphosphoranylidene)carbamic acid which are useful as diuretic agents.

Esters of (triarylphosphoranylidene)carbamic acid for effecting diuresis

This disclosure describes certain substituted piperazine-1,4-naphthalenediones useful as anti-asthmatic agents.

Substituted piperazine-1,4-naphthalenediones useful as anti-asthmatic

This invention concerns novel 2-heteroarylalkyl-1H-benz[de]isoquinoline-1,3(2H)-diones which are useful as inhibitors of thromboxane synthetase and/or as hypotensive agents in the treatment of hypertension and myocardial ischemia.

2-heteroaryl-alkyl-1H-benz[de]-isoquinoline-1,3(2H)-diones

Novel 10,10-Dihydro-10-[(substituted carbonyl)imino]-10-phenyl-10H-phenoxaphines of the formula: ##STR1## wherein A is selected from the group consisting of hydrogen and COOR.sub.1, where, when A is hydrogen the compound is in the form of a water soluble salt HnX, where n is an integer 1 or 2 and X is selected from the group consisting of sulfate, trefluoroacetate, bromide and chloride and R.sub.1 is selected from the group consisting of straight or branched chain alkyl(C.sub.1 -C.sub.4), alkenyl(C.sub.2 -C.sub.4), alkynyl(C.sub.2 -C.sub.4), cycloalkyl(C.sub.3 -C.sub.6), cycloalkyl(C.sub.3 -C.sub.6)methyl, benzyl, pyridylmethyl and tetrahydro-3-furanyl; methods for using these compounds for effecting diuresis, treating hypertension and edema and lowering plasma renin activity in mammals; pharmaceutical compositions of matter containing these compounds and processes for their preparation.

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Old Tappan, NJ, United States of America

Andrew S Tomcufcik