Sterling Drug Inc.

Sanofi

Sterling Winthrop Inc.

Nanosystems L.l.c.

Eastman-kodak Company

Sanofi Winthrop Inc.

Baldev Singh

George Y Lesher

Edward R Bacon

George Y Lesher, Deceased

Sol J Daum

William B Dickinson

Gee-Hong Kuo

Michael Reuman

Stanley C Laskowski

Carl R Illig

Chester J Opalka, Jr

Joseph C Collins

Philip M Carabateas

Shaughnessy Robinson

Sol J Daurn

George V Lesher

6-Substituted pyrazolo[3,4-d]pyrimidin-4-one derivatives, pharmaceutical compositions containing them and methods for effecting c-GMP-phosphodiesterase inhibition and for treating heart failure and/or hypertension.

6-substituted pyrazolo[3,4-d]pyrimidin-4-ones and compositions and

6-Aryl pyrazolo�3,4-d!pyrimidin-4-one derivatives, pharmaceutical compositions containing them and methods for effecting c-GMP-phosphodiesterase inhibition and for treating heart failure and/or hypertension.

6-aryl pyrazolo �3,4-d! pyrimidin-4-ones and compositions and methods of

6-aryl pyrazolo�3,4-D! pyrimidin-4-ones and compositions and method of

6-Substituted pyrazolo[3,4 -d]pyrimidin-4-one derivatives, pharmaceutical compositions containing them and methods for effecting c-GMP-phosphodiesterase inhibition and for treating heart failure and/or hypertension.

6-substituted pyrazolo (3,4-d)pyrimidin-4-ones and compositions and

This invention relates to methods of x-ray diagnostic imaging the blood pool, liver, spleen and/or lymph system of a mammal comprising administering a contrast effective amount of a contrast agent having the structure: ##STR1## wherein: n is 2; R.sup.1 is H or alkyl containing from 1 to 4 carbon atoms' R.sup.2 is H, alkyl containing from 1 to 4 carbon atoms, aryl or heteroaryl; and R.sup.3 is alkyl containing from 1 to 18 carbon atoms. This invention further relates to novel contrast agents having the above structure wherein R.sup.1 is H and R.sup.2 and R.sup.3 are CH.sub.3 to x-ray contrast compositions comprising such agents, and to method of x-ray diagnostic imaging utilizing such agents.

3 5-bis alkanoyl amino-2 4 6-triiodobenzyl esters

This invention relates to methods of x-ray diagnostic imaging the blood pool, liver, spleen and/or lymph system of a mammal comprising administering a contrast effective amount of a contrast agent having the structure: ##STR1## wherein: X is O, S or NR.sup.4 ;

Diagnostic imaging x-ray contrast agents

Novel 6-heterocyclyl-pyrazolo[3,4-d]pyrimidin-4-ones, useful in treating cardiovascular disease, are prepared by reacting a 5-amino-1H-pyrazole-4-carboxamide with heterocyclyl-carboxaldehyde or by reacting a 5-amino-1H-pyrazole-4-carbonitrile with a heterocyclylcarboxamidine, followed by diazotization and hydrolysis of the resulting 4-amino-6-heterocyclyl-pyrazolo[3,4-d]pyrimidine.

6-heterocycyclyl pyrazolo[3,4-d]pyrimidin-4-ones and compositions and

Compounds having the structure ##STR1## wherein (Z--COO is the residue of an iodinated aromatic acid; n is an integer from 0 to 20; R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently H, alkyl, fluoroalkyl, cycloalkyl, aryl, aralkyl, alkoxy, aryloxy, halogen, hydroxy, acylamino, acetamidoalkyl, acetamidoaryl, --COO-alkyl, --COO-aryl, --COO-aralkyl, --CO-alkyl, --CO-aryl, --CO-heterocyclyl, cyano or heterocyclyl; R.sup.5 is H, alkyl, fluoroalkyl, cycloalkyl, aryl, aralkyl, alkoxyalkyl, heterocyclyl, or a Z-CO.sub.2 -CR.sup.1 R.sup.2 (CR.sup.3 R.sup.4).sub.n group, wherein Z, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and n are as defined above, m is an integer from 0 to 10, p is an integer from 0 to 10, and m+p.gtoreq.1 are useful as contrast agents in x-ray imaging compositions and methods.

Iodinated aroyloxy ketones

Compounds having the structure ##STR1## wherein (Z--COO is the residue of an iodinated aromatic acid; n is an integer from 0 to 6; R.sup.1 and R.sup.2 are independently H, alkyl, fluoroalkyl, cycloalkyl, aryl, aralkyl, alkoxy or aryloxy; R.sup.3 and R.sup.4 are independently H, alkyl, fluoroalkyl, cycloalkyl, aryl, aralkyl, alkoxy, aryloxy, halogen, hydroxy or acylamino; Q represents the atoms necessary to complete a carbocyclic or heterocyclic unsaturated mono- or bicyclic aromatic ring; and R.sup.5 is H, alkyl, cycloalkyl, aryl, aralkyl, alkoxy, aryloxy, halogen, hydroxy, amino, acylamino, alkoxyalkyl, fluoroalkyl, acetamidoalkyl, COO-alkyl, cyano, carboxamido, sulfonate, sulfonamido, ureido, or carbamyl are useful as contrast agents in x-ray imaging compositions and methods.

Iodinated aromatic compounds

Novel 6-heterocyclyl-pyrazolo[3,4-d]pyrimidin-4-ones, useful in treating cardiovascular disease, are prepared by reacting a 5-amino-1H-pyrazole-4-carboxamide with heterocyclylcarboxaldehyde or by reacting a 5-amino-1H-pyrazole-4-carbonitrile with a heterocyclylcarboxamidine, followed by diazotization and hydrolysis of the resulting 4-amino-6-heterocyclyl-pyrazolo[3,4-d]pyrimidine.

6-heterocyclyl pyrazolo [3,4-d]pyrimidin-4-ones and compositions and

Fluorinated 1- cyclopropyl-7-(substituted-pyridinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxy lic acids of the formula ##STR1## wherein R is hydrogen, R' and R' are hydrogen or fluoro, and Z is 3- or 4-pyridinyl substituted by alkyl groups or substituted alkyl groups, are superior antibacterial agents. They are prepared via a coupling reaction between the corresponding esters (R=alkyl) having a halo group in the 7-position and a substituted (trialkylstannyl)-pyridine.

Pyridinyl-quinolone compounds, their preparation and use

Fluorinated 1-cyclopropyl-7-(substituted-pyridinyl)-1,4-dihydro-4-oxo-3-quinolinecarbo xylic acids of the formula ##STR1## wherein R is hydrogen, R' and R' are hydrogen or fluoro, or other groups and Z is 3- or 4-pyridinyl substituted by alkyl groups or substituted alkyl groups, are superior antibacterial agents. They are prepared via a coupling reaction between the corresponding esters (R=alkyl) having a halo group in the 7-position and a substituted (trialkylstannyl)pyridine.

1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones having an aryl or heteroaryl group in the 6-position, useful as phosphodiesterase inhibitors, are prepared by reacting a 2-amino-5-(aryl or heteroaryl)pyridine-3-carboxylic acid with diphenylphosphoryl azide. The compounds are of the formula ##STR1## where R.sub.1 and R.sub.3 are hydrogen or lower-alkyl, R.sub.5 is lower-alkyl or fluorinated lower-alkyl, and Ar is 4-or 3-pyridinyl, or N-oxides thereof, or phenyl or substituted phenyl.

Imidazopyridines, compositions and use

Novel 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones having an aryl or heteroaryl group in the 6-position, useful as phosphodiesterase inhibitors, are prepared by reacting a 2-amino-5-(aryl or heteroaryl)pyridine-3-carboxylic acid with diphenylphosphoryl azide. The compounds are of the formula ##STR1## where R.sub.1 and R.sub.3 are hydrogen or lower-alkyl, R.sub.5 is lower-alkyl or fluorinated lower-alkyl, and Ar is 4- or 3-pyridinyl, or phenyl or substituted phenyl.

Imidazopyridines, their preparation and use

5-[1H-(5-membered-N-aromatic-heteryl)-1-yl]-7-R'-1,6-naphthyridin-2(1H)-one s (formula I) or salts thereof are useful as cardiotonic agents. Also shown as intermediates are 5-X-7-R'-1,6-naphthyridin-2(1H)-ones (formula II) or salts thereof, where X is bromo, chloro or hydrazino, 2-[2-(di-lower-alkylamino)ethenyl]-1,6-dihydro-6-oxo-3-pyridinecarbonitril e (formula III), and 2-[2-(di-lower-alkylamino)-2-propenyl]-6-methoxy-3-pyridinecarbonitrile (formula IIIa). Processes shown include the preparation of I from II, preparation of II from III or IIIa and the preparation of III from 1,6-dihydro-2-methyl-6-oxo-3-pyridinecarbonitrile, and the preparation of IIIa from 6-methoxy-2-methyl-3-pyridinecarbonitrile.

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East Greenbush, NY, United States of America

Baldev Singh