Claims
- 1. 1-R"-3-Q-4-R'-5-R-1,6-naphthyridin-2(1H)-one having the formula ##STR4## or acid-addition or cationic salt thereof, where R is lower-alkyl, R' is hydrogen or methyl, R" is hydrogen or lower-alkyl, and Q is cyano, carbamyl, carboxy or aminocarbamyl.
- 2. A compound according to claim 1 where R is methyl, ethyl or propyl, R' and R" are each hydrogen, and Q is cyano.
- 3. 1,2-Dihydro-5-methyl-2-oxo-1,6-naphthyridin-3-carboxamide according to claim 1.
- 4. 1,2-Dihydro-5-methyl-2-oxo-1,6-naphthyridin-3-carbonitrile according to claim 1.
- 5. A cardiotonic composition for increasing cardiac contractility which comprises a pharmaceutically acceptable carrier and, as the active component thereof, a cardiotonically effective amount of the 1-R"-3-Q-4-R'-5-R-1,6-naphthyridin-2(1H)-one of claim 1 or pharmaceutically acceptable acid-addition or cationic salt thereof, where R, R' and R" have the meanings given in claim 1, and Q is cyano or carbamyl.
- 6. A cardiotonic composition according to claim 5 where in the active component R is methyl, ethyl or propyl, R' and R" are each hydrogen, and Q is cyano.
- 7. A 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 a cardiotonically effective amount of the 1-R"-3-Q-4-R'-5-R-1,6-naphthyridin-2(1H)-one of claim 1 or 1,6-naphthyridin-2(1H)-one or pharmaceutically acceptable acid-addition or cationic salt thereof, where R, R' and R" have the meanings given in claim 1 and Q is cyano or carbamyl.
- 8. A method according to claim 7 where in the active component R is methyl, ethyl or propyl, R' and R" are each hydrogen, and Q is cyano.
- 9. The process which comprises reacting 3-Q'-4-R'-5-(RCO)-6-methyl-2(1H)-pyridinone with di-(lower-alkyl)formamide di-(lower-alkyl)acetal to produce 3-Q'-4-R'-5-(RCO)-6-[2-(di-lower-alkylamino)ethenyl]-2(1H)-pyridinone where Q' is hydrogen or cyano, R' is hydrogen or methyl, and R, R.sub.1 and R.sub.2 are each lower-alkyl.
- 10. The process according to claim 9 which comprises reacting 5-acetyl-6-methyl-2(1H)-pyridinone with dimethylformamide dimethyl acetal to produce 5-acetyl-6-(2-dimethylaminoethenyl)-2(1H)-pyridinone.
- 11. The process according to claim 9 which comprises reacting 6-methyl-5-(n-propanoyl)-2(1H)-pyridinone with dimethylformamide dimethyl acetal to produce 6-(2-dimethylaminoethenyl)-5-(n-propanoyl)-2(1H)-pyridinone.
- 12. The process which comprises reacting 3-Q'-4-R'-5-(RCO)-6-[2-(di-lower-alkylamino)ethenyl]-2(1H)-pyridinone with formamidine, ammonia or salt thereof to produce 3-Q-4-R'-5-R-1,6-naphthyridin-2(1H)-one of claim 1 where Q and Q' are each cyano or hydrogen, R' is hydrogen or methyl, R is lower-alkyl and R" is hydrogen.
- 13. The process according to claim 12 which comprises reacting 5-acetyl-6-(2-dimethylaminoethenyl)-2(1H)-pyridinone with formamidine or ammonium acetate to produce 5-methyl-1,6-naphthyridin-2(1H)-one.
- 14. The process according to claim 12 which comprises reacting 6-(2-dimethylaminoethenyl)-5-(n-propanoyl)-2(1H)-pyridinone with formamidine or ammonium acetate to produce 5-ethyl-1,6-naphthyridin-2(1H)-one.
CROSS-REFERENCE TO RELATED APPLICATION
This application is a division of copending U.S. patent application Ser. No. 502,858, filed June 9, 1983 and now U.S. Pat. No. 4,517,190, issued May 14, 1985, which in turn is a continuation-in-part of copending application Ser. No. 404,454, filed Aug. 2, 1982 and now U.S. Pat. No. 4,415,580, issued Nov. 15, 1983.
Non-Patent Literature Citations (7)
Entry |
Robert Morrison and Robert Boyd, "Organic Chemistry," 2nd Ed., Allyn and Bacon, Inc., Boston, (1966). |
Alfred Burger, J. of Chemical Education, 33, 362(8), 1956. |
Chemical Abstracts 72, 12,615d, (1970). |
Ogata et al., [Chem. Pharm. Bull. 20, 2264, (1972)]. |
Hawes et al., [J. Med. Chem. 16, 849, (1974)]. |
Hawes et al., [J. Heterocycl. Chem. 11, 151, (1974)]. |
Moller et al., [Ann. 612, 153, (1957)]. |
Divisions (1)
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502858 |
Jun 1983 |
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Continuation in Parts (1)
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404454 |
Aug 1982 |
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