Claims
- 1. A compound of the formula: ##STR18## wherein R.sub.9 is alkyl of 1 to 4 carbon atoms, wherein R.sub.p.sup.o is alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, cycloalkylalkyl in which the cycloalkyl is of 3 to 6 carbon atoms and the alkyl portion is of 1 or 2 carbon atoms, or ##STR19## M.sub.p is hydrogen or a pharmaceutically acceptable cation, n is 0 or 1,
- Y and Y' are independently hydrogen, fluoro, chloro, bromo, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, trifluoromethyl or nitro with the proviso that only one of Y and Y' can be from the group of nitro and trifluoromethyl, and
- R.sub.p and R.sub.p ' are independently hydrogen, fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro or trifluoromethyl, with the proviso that only one of R.sub.p and R.sub.p ' can be from the group consisting of nitro and trifluoromethyl,
- with the further proviso that the unsaturation in any alkenyl or alkynyl is on other than the alpha carbon atom.
- 2. A compound of claim 1 in which M.sub.p is hydrogen.
- 3. A compound of claim 1 in which R.sub.p.sup.o is alkenyl.
- 4. A compound of claim 1 in which R.sub.p.sup.o is alkynyl.
- 5. A compound of claim 1 in which R.sub.p.sup.o is cycloalkyl.
- 6. A compound of claim 1 in which R.sub.p.sup.o is cycloalkylalkyl.
- 7. A compound of claim 1 in which R.sub.p.sup.o is ##STR20##
- 8. A compound of claim 7 in which n is 0.
- 9. A compound of claim 7 in which n is 1.
- 10. A compound of claim 1 in which R.sub.p and R.sub.p ' are each alkoxy of 1 to 4 carbon atoms.
- 11. A compound of claim 10 in which R.sub.p and R.sub.p ' represent 6,7-dialkoxy.
- 12. A compound of claim 11 in which R.sub.p and R.sub.p ' represent 6,7-dimethoxy.
- 13. A compound of claim 12 in which R.sub.p.sup.o is allyl.
- 14. The compound of claim 3 which is N-allyl-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
- 15. The compound of claim 13 which is N-allyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
- 16. The compound of claim 9 which is N-(p-fluorobenzyl)-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
- 17. The compound of claim 5 which is N-cyclopentyl-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
- 18. The compound of claim 6 which is N-cyclopropylmethyl-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
- 19. The compound of claim 4 which is N-propargyl-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
- 20. The compound of claim 8 which is N-phenyl-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
- 21. A compound of the formula: ##STR21## wherein R.sup.o is alkyl of 1 to 6 carbon atoms,
- R" is hydrogen, fluoro, chloro, bromo or alkoxy of 1 to 4 carbon atoms, and
- R.sub.9 is alkyl of 1 to 4 carbon atoms.
- 22. The compound of claim 21 which is N-hexyl-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
- 23. The compound of claim 21 which is N-ethyl-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
- 24. The compound of claim 21 which is N-butyl-7-chloro-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
- 25. The compound of claim 21 which is N-methyl-6-methoxy-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
- 26. The compound of claim 21 which is N-methyl-6-chloro-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
- 27. A compound of the formula: ##STR22## wherein R.sub.9 is alkyl of 1 to 4 carbon atoms, wherein R.sub.p.sup.o is alkyl of 1 to 6 carbon atoms,
- M.sub.p is hydrogen or a pharmaceutically acceptable cation, and
- R.sub.p and R.sub.p ' are independently alkoxy of 1 to 4 carbon atoms.
- 28. A compound of claim 27 in which R.sub.p and R.sub.p ' represent 6,7-dialkoxy.
- 29. A compound of claim 28 in which R.sub.p and R.sub.p ' represent 6,7-dimethoxy.
- 30. A compound of claim 29 in which R.sub.p.sup.o is methyl.
- 31. The compound of claim 30 which is N-methyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
- 32. A compound of the formula: ##STR23## wherein R.sub.9 is alkyl of 1 to 4 carbon atoms, wherein R.sub.p.sup.o is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, cycloalkylalkyl in which the cycloalkyl is of 3 to 6 carbon atoms and the alkyl portion is of 1 or 2 carbon atoms, or ##STR24## M.sub.p is hydrogen or a pharmaceutically acceptable cation, n is 0 or 1, and
- Y and Y' are independently hydrogen, fluoro, chloro, bromo, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, trifluoromethyl or nitro, with the proviso that only one of Y and Y' can be from the group consisting of nitro and trifluoromethyl,
- with the further proviso that the unsaturation in any alkenyl or alkynyl is on other than the alpha carbon atom.
- 33. A compound of claim 32 in which R.sub.p.sup.o is alkyl.
- 34. A compound of claim 32 in which R.sub.p.sup.o is alkenyl.
- 35. A compound of claim 34 in which R.sub.p.sup.o is allyl.
- 36. The compound of claim 35 which is N-allyl-6,7-methylenedioxy-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
- 37. The compound of claim 13 which is N-allyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid n-butyl ester.
- 38. The compound of claim 13 which is N-allyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid t-butyl ester.
- 39. A compound of claim 3 in which R.sub.p.sup.o is allyl.
- 40. A compound of claim 39 in which R.sub.p is alkyl of 1 to 4 carbon atoms in the 7-position and R.sub.p ' is alkoxy of 1 to 2 carbon atoms in the b 6-position.
- 41. The compound of claim 40 which is N-allyl-6-methoxy-7-ethyl-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
- 42. The compound of claim 40 which is N-allyl-6-methoxy-7-methyl-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester.
Parent Case Info
This is a division of application Ser. No. 807,898 filed June 20, 1977 now U.S. Pat. No. 4,190,659, which in turn is a continuation-in-part of Ser. No. 662,148, filed Feb. 27, 1976, now abandoned, which in turn is a continuation-in-part of Ser. No. 557,984, filed Mar. 12, 1975, now abandoned, which in turn is a division of Ser. No. 454,070, filed Mar. 25, 1974, now abandoned which in turn is a continuation-in-part of Ser. No. 303,099, filed Nov. 2, 1972 and of Ser. No. 392,082, filed Aug. 27, 1973, now both abandoned.
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Foreign Referenced Citations (7)
Number |
Date |
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806848 |
Oct 1973 |
BEX |
2431584 |
Jan 1975 |
DEX |
2705446 |
Aug 1977 |
DEX |
2554772 |
Mar 1978 |
DEX |
43-23948 |
Oct 1968 |
JPX |
1121411 |
Jul 1968 |
GBX |
1334705 |
Oct 1973 |
GBX |
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Entry |
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Related Publications (1)
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Date |
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392082 |
Aug 1973 |
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Divisions (2)
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Number |
Date |
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Parent |
807898 |
Jun 1977 |
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Parent |
454070 |
Mar 1974 |
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Continuation in Parts (3)
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662148 |
Feb 1976 |
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Parent |
557984 |
Mar 1975 |
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303099 |
Nov 1972 |
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