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Serving hundreds of leading biopharmaceutical companies globally:

Fish and Richardson
Argus Health
Daiichi Sankyo

Generated: May 21, 2018

DrugPatentWatch Database Preview

Details for Patent: 4,137,233

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Title: 1,2-Dihydro-2-oxo-5-(pyridinyl)nicotinamides
Abstract:Compounds useful as cardiotonic agents are 1-R-3-Q-5-PY-2(1H)-pyridinones (I) where R is hydrogen, lower-alkyl or lower-hydroxyalkyl, Q is amino (preferred), lower-alkylamino, di-(lower-alkyl)amino or NHAc, Ac is lower-alkanoyl or lower-carbalkoxy, and PY is 4- or 3- or 2-pyridinyl or 4- or 3- or 2-pyridinyl having one or two lower-alkyl substituents. The corresponding compounds where Q is nitro, carbamyl, cyano, halo or hydrogen are useful as intermediates and those where Q is hydrogen or cyano also are useful as cardiotonic agents. Said compounds are prepared: by reacting .alpha.-PY-.beta.-(R.sub.1 R.sub.2 N)acrolein (II) with malonamide to produce 1,2-dihydro-2-oxo-5-PY-nicotinamide (Ia) and reacting Ia with a reagent capable of converting carbamyl to amino to produce 3-amino-5-PY-2(1H)-pyridinone (Ib); by reacting II or .alpha.-PY-malonaldehyde (II') with .alpha.-cyanoacetamide to produce 1,2-dihydro-2-oxo-5-PY-nicotinonitrile (III) and partially hydrolyzing III to produce Ia; and, by heating 1,2-dihydro-2-oxo-5-PY-nicotinic acid (IV) with a mixture of concentrated sulfuric acid and concentrated nitric acid to produce 3-nitro-5-PY-2(1H)-pyridinone (Ic) and then either reducing Ic to produce Ib or first reacting Ic with an alkylating agent to produce 1-R'-3-nitro-5-PY-2(1H)-pyridinone (Id) and reducing Id to produce 1-R'-3-amino-5-PY-2(1H)-pyridinone (Ib) where R' is lower-alkyl or lower-hydroxyalkyl. Other derivatives of I where Q is amino are shown.
Inventor(s): Lesher; George Y. (Schodack, NY), Opalka, Jr.; Chester J. (Schodack, NY)
Assignee: Sterling Drug Inc. (New York, NY)
Filing Date:Feb 10, 1978
Application Number:05/876,571
Claims:1. A 1-R-3-Q-5-PY-2(1H)-pyridinone having the formula ##STR4## where PY is 4- or 3- or 2-pyridinyl or 4- or 3- or 2-pyridinyl having one or two lower-alkyl substituents, R is hydrogen, lower-alkyl or lower-hydroxyalkyl and Q is carbamyl, or pharmaceutically-acceptable acid-addition salt thereof.

2. A compound according to claim 1 where Q is carbamyl and R is hydrogen.

3. 1,2-Dihydro-2-oxo-5-(4-pyridinyl)nicotinamide according to claim 2.

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Serving hundreds of leading biopharmaceutical companies globally:

Argus Health
Cantor Fitzgerald
Fish and Richardson

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