6-alkyl-5-(pyridinyl)-3-substituted-2(1h)-pyridinones,...

Details 6-alkyl-5-(pyridinyl)-3-substituted-2(1h)-pyridinones,... 6-alkyl-5-(pyridinyl)-3-substituted-2(1h)-pyridinones,...

C - Chemistry, Metallurgy

07

D

260/279.4

C07D 213/64 (2006.01) C07D 213/50 (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) C07D 401/04 (2006.01)

Patent

CA 1143736

D.N. 3678A ABSTRACT OF THE DISCLOSURE 1-R1-3-[amino, cyano, carbamyl, halo, lower- alkylamino, di-(lower-alkyl)amino or lower-acylamino]-6- (lower-alkyl)-5-(pyridinyl)-2(lH)-pyridinones or pharma- ceutically-acceptable acid-addition or cationic salts thereof are useful as cardiotonic agents, where R1 is hydrogen, lower-alkyl or lower-hydroxyalkyl. l-R1-3-amino- 6-(lower-alkyl)-5-(pyridinyl)-2(lH)-pyridinones are prepared by hydrolyzing the corresponding 3-cyano compounds to produce the corresponding 3-carbamyl compounds and reacting the latter with a reagent capable of converting carbamyl to amino. The l-R1-3-cyano-6-(lower-alkyl)-5-(pyridinyl)- 2(lH)-pyridinones are prepared by reacting (pyridinylmethyl) lower-alkyl ketones with dimethylformamide di-(lower-alkyl) acetal to produce 1-(pyridinyl)-2-(dimethylamino)ethenyl lower-alkyl ketone and reacting said ketones with N-R1-o- cyanoacetamide to produce the 1-R1-3-cyano-6-(lower-alkyl)- 5-(pyridinyl)-2(1H)-pyridinones. Also shown are the conversions: of the 3-cyano compounds to the 3-H compounds; of the 3-H compounds to the 3-halo compounds; of the 3-halo compounds to the 3-[mono-(lower-alkyl)-or di-(lower-alkyl)- amino]compounds; and, of the 3-amino compounds to the 3- lower-acylamino or 3-[mono-(lower-alkyl)- or di-(lower- alkyl)amino] compounds.

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