5-(Phenyl)-1,6-naphthyridin-2(1H)-ones, their cardiotonic use an

Details 5-(Phenyl)-1,6-naphthyridin-2(1H)-ones, their cardiotonic use an 5-(Phenyl)-1,6-naphthyridin-2(1H)-ones, their cardiotonic use an

1984-07-13

1985-12-24

Jiles, Henry R.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

546122, 546298, 514350, A61K 3144, C07D21350, C07D21346, C07D47104

Patent

active

045606919

ABSTRACT:
1-R-5-Ar-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is hydrogen or methyl, and Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, hydroxy, amino, acetylamino, methanesulfonylamino, bromo, chloro, fluoro, cyano or carbamyl are useful as cardiotonic agents and corresponding compounds where Ar is nitrophenyl are useful as intermediates. Also shown as intermediates, are 5-(Ar--CO)-6-[2-(di-lower-alkylamino)-ethenyl]-2(1H)-pyridinones (II) or salts thereof, where Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, bromo, chloro, fluoro, cyano or nitro and 5-(Ar--CO)-6-methyl-2(1H)-pyridinones (III) where Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, bromo, chloro, fluoro, hydroxy, cyano or nitro; said compounds (III) where Ar is phenyl or hydroxyphenyl also are useful as cardiotonic agents. Processes for preparing the compounds of formulas I, II and III are shown.

REFERENCES:
patent: 4412077 (1983-10-01), Lesher et al.
patent: 4415580 (1983-11-01), Lesher et al.
Robert Morrison and Robert Boyd, "Organic Chemistry", Second Ed., Allyn and Bacon, Inc., Boston (1966).
Calain A. Buehler and Donald E. Pearson, "Survey of Organic Syntheses", Wiley-Interscience, 1970.
Hawes et al., J. Het. Chem. 11 (2), 151-155 (1974).
Kato et al., [J. Heterocyclic Chem. 18, 603-606 (1981)].
Kato et al., [Chem. Pharm. Bull. 17, 2411-2416 (1969)].

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