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1,4-Dihydro-4-oxo-7-pyridyl-3-quinolinecarboxylic acid derivatives

Assignee: STWB Inc
•
Filing: 1973-05-03
•
Granted: 1975-09-23
•
Expires: 1993-05-03
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Abstract

Abstract 1,4-Dihydro-1-(lower-alkyl)-4-oxo-5(or 6)-R''-7-pyridyl-3quinolinecarboxylic acids and lower-alkyl esters, where R'' is hydrogen, halo, lower-alkyl or lower-alkoxy and pyridyl is unsubstituted or substituted, having antibacterial activity, are prepared by reacting the corresponding 1,4-dihydro-4-oxo-7pyridyl-3-quinolinecarboxylic acid or lower-alkyl ester with an alkylating agent, e.g., lower-alkyl halide, sulfate or sulfonate, and by other methods.

Inventors

  • 👤 George Y Lesher
  • 👤 Philip M Carabateas

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 15:10
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/28; C07D213/30; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/435; A61K31/44; C07C; C07C255/00; C07D211/00; C07D211/02; C07D211/04; C07D211/68; C07D211/72; C07D211/78; C07D211/80; C07D211/84; C07D211/90; C07D213/26; C07D213/36; C07D213/38; C07D213/44; C07D213/46; C07D213/48; C07D213/60; C07D213/62; C07D213/63; C07D213/64; C07D213/72; C07D213/73; C07D213/78; C07D213/79; C07D213/80; C07D213/84; C07D213/85; C07D213/89; C07D229/00; C07D401/00; C07D401/02; C07D401/04

Claims Analysis

Total Claims: 27
Claim 1
Independent Claim 180 words
A COMPOUND SELECTED FROM: 1-R1-1,4-DIHYDRO-3(COOR)-4-OXO-5(OR 6)-R''-7-PY-QUINOLINE WHERE R1 NONTERTIARY LOWER-ALKYL, LOWER-HYDROXYALKYL OR LOWER-HALOALKYL, R IS HYDROGEN, NON-TERIARY LOWER-ALKYL OR CH2OAC WHERE AC IS LOWER-ALKANOL OR BENZOYL, R'' IS HALO, NON-TERTIARY LOWER-ALKYL OR LOWER-ALKOXY OR R'' IS HYDROGEN WHEN R IS CH2OAC, AND PY IS Q-1-(O)N-4(3 OR 2)-PYRIDYL, Q-1-Q''-4(3 OR 2)-PIPERIDYL OR 1-(LOWER-ALKYL)-1,2-DIHYDRO-2-OXO-4-PYRIDYL, WHERE N IS ZERO OF 1, Q IS FROM ZERO TO FOUR SUBSTITUENTS SELECTED FROM NON-TERTIARY LOWER-ALKYL WHERE TWO OF FOUR SAID SUBSTITUTENTS AT THE 3AND 5-POSITIONS OF 4-PYRIDYL CAN BE REPLACED BY LOWERCARBALKOXY OR CARBOXY, OR Q IS FROM ONE TO TWO SUBSTUENTS SELECTED FROM LOWER-ALKOXY, HALO, HYDROXY, LOWER-ALKANOYLOXY, HYDROXYMETHYL, FORMYL, CARBOXY AND LOWER-CARBALKOXY WHERE ONE OF THE TWO SAID SUBSTITENTS CAN BE REPLACED BY NON-TERIARY LOWER-ALKYL, OR Q IS A SINGLE SUBSTITUENT SELECTED FROM AMINOMETHYL, LOWER-ALKANOYALMINOMETHYL, AMINO, CYANO AND CARBAMYL, AND Q'' IS HYDROGEN OR NON-TERIARY LOWER-ALKYL, WHERE LOWER IN EACH OF LOWER-ALKYL, LOWERALKOXYL, LOWER-ALKANOYL AND ALKOXYL OF LOWER-CARBALKOXY DESIGNATES FROM ONE TO SIX CARBON ATOMS AND IN EACH OF LOWERHYDROXYALKYL AND LOWERHALOALKYL DESINGANTES FROM TWO TO SIX CARBON ATOMS, AND, A MEDICINALLY ACCEPTABLE SALT THEREOF.
Claim 2
Dependent Claim 180 words
A COMPOUND SELECTED FROM: 1-R1-1,4-DIHYDRO-3(COOR)-4-OXO-5(OR 6)-R''-7-PY-QUINOLINE WHERE R1 NONTERTIARY LOWER-ALKYL, LOWER-HYDROXYALKYL OR LOWER-HALOALKYL, R IS HYDROGEN, NON-TERIARY LOWER-ALKYL OR CH2OAC WHERE AC IS LOWER-ALKANOL OR BENZOYL, R'' IS HALO, NON-TERTIARY LOWER-ALKYL OR LOWER-ALKOXY OR R'' IS HYDROGEN WHEN R IS CH2OAC, AND PY IS Q-1-(O)N-4(3 OR 2)-PYRIDYL, Q-1-Q''-4(3 OR 2)-PIPERIDYL OR 1-(LOWER-ALKYL)-1,2-DIHYDRO-2-OXO-4-PYRIDYL, WHERE N IS ZERO OF 1, Q IS FROM ZERO TO FOUR SUBSTITUENTS SELECTED FROM NON-TERTIARY LOWER-ALKYL WHERE TWO OF FOUR SAID SUBSTITUTENTS AT THE 3AND 5-POSITIONS OF 4-PYRIDYL CAN BE REPLACED BY LOWERCARBALKOXY OR CARBOXY, OR Q IS FROM ONE TO TWO SUBSTUENTS SELECTED FROM LOWER-ALKOXY, HALO, HYDROXY, LOWER-ALKANOYLOXY, HYDROXYMETHYL, FORMYL, CARBOXY AND LOWER-CARBALKOXY WHERE ONE OF THE TWO SAID SUBSTITENTS CAN BE REPLACED BY NON-TERIARY LOWER-ALKYL, OR Q IS A SINGLE SUBSTITUENT SELECTED FROM AMINOMETHYL, LOWER-ALKANOYALMINOMETHYL, AMINO, CYANO AND CARBAMYL, AND Q'' IS HYDROGEN OR NON-TERIARY LOWER-ALKYL, WHERE LOWER IN EACH OF LOWER-ALKYL, LOWERALKOXYL, LOWER-ALKANOYL AND ALKOXYL OF LOWER-CARBALKOXY DESIGNATES FROM ONE TO SIX CARBON ATOMS AND IN EACH OF LOWERHYDROXYALKYL AND LOWERHALOALKYL DESINGANTES FROM TWO TO SIX CARBON ATOMS, AND, A MEDICINALLY ACCEPTABLE SALT THEREOF.
Claim 3
Dependent Claim 9 words
A compound selected from: a compound of the formula
Claim 4
Dependent Claim 9 words
A compound selected from: a compound of the formula
Claim 5
Dependent Claim 94 words
1-R1-1,4-dihydro-3-(COOR)-4-oxo-5(or 6)-R''-7-PY-quinoline where R1 is non-tertiary lower-alkyl or CH2OAc where Ac is lower-alkanoyl or benzoyl, R'' is halo, non-tertiary lower-alkyl or lower-alkoxy or R'' is hydrogen when R is CH2OAc, and PY is 4(or 3)-pyridyl or 4(or 3)-pyridyl having one to three non-tertiary lower-alkyl substituents or having two non-tertiary lower-alkyl substituents and two carboxy or lower-carbalkoxy substituents or having one non-tertiary lower-alkyl and one halo substituents or having one halo substituent, where lower alkyl, lower-alkoxy, lower-alkanoyl or alkoxy of lower-carbalkoxy each has from one to six carbon atoms; or a medicinally acceptable salt thereof.
Claim 6
Dependent Claim 94 words
1-R1-1,4-dihydro-3-(COOR)-4-oxo-5(or 6)-R''-7-PY-quinoline where R1 is non-tertiary lower-alkyl or CH2OAc where Ac is lower-alkanoyl or benzoyl, R'' is halo, non-tertiary lower-alkyl or lower-alkoxy or R'' is hydrogen when R is CH2OAc, and PY is 4(or 3)-pyridyl or 4(or 3)-pyridyl having one to three non-tertiary lower-alkyl substituents or having two non-tertiary lower-alkyl substituents and two carboxy or lower-carbalkoxy substituents or having one non-tertiary lower-alkyl and one halo substituents or having one halo substituent, where lower alkyl, lower-alkoxy, lower-alkanoyl or alkoxy of lower-carbalkoxy each has from one to six carbon atoms; or a medicinally acceptable salt thereof.
Claim 7
Dependent Claim 5 words
A compound of the formula
Claim 8
Dependent Claim 5 words
A compound of the formula
Claim 9
Dependent Claim 5 words
A compound of the formula
Claim 10
Dependent Claim 5 words
A compound of the formula
Claim 11
Dependent Claim 5 words
A compound of the formula
Claim 12
Dependent Claim 5 words
A compound of the formula
Claim 13
Dependent Claim 12 words
1-Ethyl-1,4-dihydro-5-methyl-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylic acid according to claim 5 or a medicinally acceptable salt thereof.
Claim 14
Dependent Claim 13 words
1-Ethyl-1,4-dihydro-5-methyl-7-(2-methyl-4-pyridyl)-4-oxo-3 -quinolinecarboxylic acid according to claim 5 or a medicinally acceptable salt thereof.
Claim 15
Dependent Claim 13 words
1-Ethyl-1,4-dihydro-6-methyl-7-(2,6-dimethyl-4-pyridyl)-4-oxo-3 -quinolinecarboxylic acid according to claim 5 or a medicinally acceptable salt thereof.
Claim 16
Dependent Claim 12 words
Pivaloyloxymethyl 1-ethyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylate according to claim 6 or a medicinally acceptable salt thereof.
Claim 17
Dependent Claim 12 words
Benzoyloxymethyl 1-ethyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylate according to claim 6 or a medicinally acceptable salt thereof.
Claim 18
Dependent Claim 8 words
1-Ethyl-1,4-dihydro-7-(2-methyl-5-pyridyl)-4-oxo-3-quinolinecarboxylic acid or a medicinally acceptable salt thereof.
Claim 19
Dependent Claim 8 words
1-Ethyl-1,4-dihydro-7-(2-methyl-5-pyridyl)-4-oxo-3-quinolinecarboxylic acid or a medicinally acceptable salt thereof.
Claim 20
Dependent Claim 8 words
1-Ethyl-7-(2-ethyl-4-pyridyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid or a medicinally acceptable salt thereof.
Claim 21
Dependent Claim 8 words
1-Ethyl-7-(2-ethyl-4-pyridyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid or a medicinally acceptable salt thereof.
Claim 22
Dependent Claim 5 words
A compound of the formula
Claim 23
Dependent Claim 5 words
A compound of the formula
Claim 24
Dependent Claim 5 words
A compound of the formula
Claim 25
Dependent Claim 5 words
A compound of the formula
Claim 26
Dependent Claim 5 words
A compound of the formula
Claim 27
Dependent Claim 5 words
A compound of the formula

References Cited (Backward Citations)

US3287458A Cited
US3472859A Cited
US3524858A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-09-22 1979-03-24 1979-09-23 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-09-22 1983-03-24 1983-09-23 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-09-22 1987-03-24 1987-09-23 $7700.00 Window Closed / Lapsed

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