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Claims for Patent: 4,072,746

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Claims for Patent: 4,072,746

Title: 3-Amino-5-(pyridinyl)-2(1H)-pyridinones
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. (East Greenbush, NY), Opalka, Jr.; Chester J. (Schodack, NY)
Assignee: Sterling Drug Inc. (New York, NY)
Application Number:05/707,235
Patent 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 nitro, amino, lower-alkylamino di-(lower-alkyl)amino, or NHAc where Ac is lower-alkanoyl or lower-carbalkoxy, or pharmaceutically-acceptable acid-addition salt thereof.

2. A 1-R-3-Q-5-PY-2 (1H)-pyridinone having the formula ##STR5## 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 nitro, lower-alkylamino, di-(lower-alkyl)amino, or NHAc where Ac is lower-alkanoyl or lower-carbalkoxy, or pharmaceutically-acceptable acid-addition salt thereof.

3. A 1-R-3-amino-5-PY-2 (1H)-pyridinone having the formula ##STR6## where PY is 4- or 3- or 2-pyridinyl or 4- or 3- or 2-pyridinyl having one or two lower-alkyl substituents and R is hydrogen, lower-alkyl or lower-hydroxyalkyl, or pharmaceutically-acceptable acid-addition salt thereof.

4. A compound according to claim 2 where Q is nitro.

5. A compound according to claim 3 where R is hydrogen.

6. A compound according to claim 3 where R is lower-alkyl.

7. 3-Amino-5-(4-pyridinyl)-2 (1H)-pyridinone .

8. 3-Amino-5-(3-pyridinyl)-2 (1H)-pyridinone according to claim 5.

9. 3-Amino-1-methyl-5-(4-pyridinyl)-2 (1H)-pyridinone according to claim 6.

10. 3-Amino-1-ethyl-5-(4-pyridinyl)-2 (1H)-pyridinone according to claim 6.

11. N-[1,2-Dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]-acetamide according to claim 2.

12. Methyl N-[1,2-dihydro-2-oxo-5-(4-pyridinyl)-3-pyridinyl]carbamate according to claim 2.

13. 3-Nitro-5-(4-pyridinyl)-2 (1H)-pyridinone according to claim 4.

14. A cardiotonic composition for increasing cardiac contractility, said composition comprising a pharmaceutically-acceptable inert carrier and, as the active component thereof, an effective amount of a cardiotonic 1-R-3-Q-5-PY-2 (1H)-pyridinone having the formula ##STR7## 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 amino, lower-alkylamino, di-(lower-alkyl)amino or NHAc where Ac is lower-alkanoyl or loer-carbalkoxy, or pharmaceutically-acceptable acid-addition salt thereof.

15. A composition according to claim 14 where the active component is 3-amino-5-(4-pyridinyl)-2 (1H)-pyridinone.

16. The method for increasing cardiac contractility in a patient requiring such treatment which comprises administering orally or parenterally in a solid or liquid dosage form to such patient an effective amount of a cardiotonic 1-R-3-Q-5-PY-2 (1H)-pyridinone having the formula ##STR8## 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 amino, lower-alkylamino, di-(lower-alkyl) amino or NHAc where Ac is lower-alkanoyl or lower-carbalkoxy, or pharmaceutically acceptable acid-addition salt thereof.

17. The method according to claim 16 where the 1-R-3-Q-5-PY-2 (1H)-pyridinone is 3-amino-5-(4-pyridinyl)-2 (1H)-pyridinone.

18. A compound according to claim 2 where Q is lower-alkylamino and R is hydrogen.

19. 3-Methylamino-5-(4-pyridinyl)-2 (1H)-pyridinone according to claim 18.

20. A compound according to claim 2 where Q is di-(lower-alkyl) amino and R is hydrogen.

21. 3-Dimethylamino-5-(4-pyridinyl)-2 (1H)-pyridinone according to claim 20.
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