Pyridinyl-2(1h)-pyridinones and preparation

Details Pyridinyl-2(1h)-pyridinones and preparation Pyridinyl-2(1h)-pyridinones and preparation

C - Chemistry, Metallurgy

07

D

260/279.4

C07D 213/64 (2006.01) C07D 213/38 (2006.01) C07D 213/48 (2006.01) C07D 213/53 (2006.01) C07D 213/73 (2006.01) C07D 213/74 (2006.01) C07D 213/75 (2006.01) C07D 213/80 (2006.01) C07D 213/82 (2006.01) C07D 213/85 (2006.01)

Patent

CA 1089860

ABSTRACT OF THE DISCLOSURE Compounds useful as cardiotonic agents are 1-R-3- Q-5-PY-2(1H)-pyridinones of Formula I (herein) 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 sub- stituents. 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.- (R1R2N)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(lH)- pyridinone (Ib); by reacting II or .alpha.-PY-malonaldehyde (II') with .alpha.-cyanoacetamide to produce 1,2-dihydro-2-oxo-5-PY-nicotino- nitrile (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(lH)-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.

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