US2008176897A1PendingUtilityA1
Substituted Quinolone Carboxylic Acids, Their Derivatives, Site of Action, And Uses Thereof
Est. expiryMay 14, 2022(expired)· nominal 20-yr term from priority
A61P 43/00A61P 25/24A61P 25/00A61P 29/00A61P 25/02A61P 25/18A61P 25/22A61P 25/30A61P 25/20A61P 25/36A61P 25/28A61P 25/08A61P 25/06A61P 21/02C07D 215/56C07D 215/20
47
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Claims
Abstract
Substituted quinolone carboxylic acids and their derivatives are described. These compounds modulate the effect of γ-aminobutyric acid (GABA) via a novel site on the GABA A receptor complex in a therapeutically relevant fashion and may be used to ameliorate CNS disorders amenable to modulation of the GABA A receptor complex.
Claims
exact text as granted — not AI-modified1 - 13 . (canceled)
14 . A method for the treatment of CNS disorders amenable to amelioration via modulation of the GABA A receptor complex, comprising the step of: administering to a patient in need of such treatment an effective amount of compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl; a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen;
R 9 and R 10 are independently selected from the group consisting of optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring.
15 . The method of claim 14 , wherein the compound comprises a compound having the Formula II:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen;
R 9 and R 10 are independently selected from the group consisting of optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring.
16 . The method of claim 14 , wherein the compound comprises a compound having the Formula III:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein: R 1 , R 2 , R 5 , R 7 , R 8 , R 9 are as defined in claim 1 ; n is an integer 0, 1, 2, 3 or 4.
17 . The method of claim 16 , wherein n is 2.
18 . The method of claim 16 , wherein R 1 is alkyl, R 2 , R 5 and R 8 are hydrogen and R 7 is halogen.
19 . The method of claim 14 , wherein the compound is: 7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro (phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid or a pharmaceutically acceptable salt, prodrug or solvate thereof.
20 . A method for the treatment of anxiety and related disorders, which comprises administering to a patient in need of such treatment an effective amount of a compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl; a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl and halogen;
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, aryl, cycloalkyl and cycloaralkyl, or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
21 . A method for the treatment of convulsions, which comprises administering to a patient in need of such treatment an effective amount of a compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl; a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen;
R 9 and R 10 are independently selected from the group consisting of hydrogen optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
22 . A method for the treatment of insomnia, which comprises administering to a patient in need of such treatment an effective amount of compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl, a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen;
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
23 . A method for the treatment of major depressive and bipolar disorders, which comprises administering to a patient in need of such treatment an effective amount of compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl; a group OR 11 and NR 12 R 13 .
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl and halogen;
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
24 . A method for the treatment of chronic or acute pain, which comprises administering to a patient in need of such treatment an effective amount of compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl; a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen;
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
25 . A method for the treatment of neuroses, which comprises administering to a patient in need of such treatment an effective amount of compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl; a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen;
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
26 . A method for the treatment of withdrawal-induced convulsions from substance abuse which comprises administering to a patient in need of such treatment an effective amount of compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl; a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen;
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, aryl, cycloalkyl and cycloaralkyl, or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are, H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
27 . A method for the treatment of phobias, which comprises administering to a patient in need of such treatment an effective amount of compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl; a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen;
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
28 . A method for the treatment of panic disorders, which comprises administering to a patient in need of such treatment an effective amount of compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl, a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen;
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl,
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
29 . A method for the treatment of generalized anxiety disorders which comprises administering to a patient in need of such treatment an effective amount of compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl; a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen;
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
30 . A method for the treatment of obsessive-compulsive disorders which comprises administering to a patient in need of such treatment an effective amount of compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl; a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen;
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl:
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
31 . A method for the treatment of post traumatic and acute stress disorders, which comprises administering to a patient in need of such treatment an effective amount of compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen, an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen;
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
32 . A method for the treatment of migraine pain, which comprises administering to a patient in need of such treatment an effective amount of compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen, an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl, a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen;
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl aralkyl, aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
33 . A method for the treatment of bipolar manic disorders, which comprises administering to a patient in need of such treatment an effective amount of compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl; a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen;
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl aralkyl, aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
34 . A method for the treatment of cognition deficit disorders, which comprises administering to a patient in need of such treatment an effective amount of compound of Formula I:
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen,
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , —R 11 is H, R 5 and R 8 are H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
35 . A method for the treatment of disorders such as anxiety and stress related disorders, depression and other affective disorders, epilepsy and other seizure disorders, insomnia and related sleep disorders, and acute and chronic pain by enhancement of chloride conductance through the site mediating the action of compound of Formula I
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen, an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl; a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen;
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are H, then R 1 is not Et, with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
36 . A method for the treatment of disorders related to learning and memory such as mild cognitive impairment, age related cognitive decline, senile dementia, Alzheimer's disease, sleep disorders involving reduced wakefulness such as narcolepsy and idiopathic hypersomnia by inhibition of chloride conductance through the site mediating the action of compound of Formula I
or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:
R 1 is selected from the group consisting of hydrogen; an optionally substituted alkyl, and aralkyl;
each R 2 is selected from the group consisting of hydrogen and optionally substituted alkyl;
each R 3 is selected from the group consisting of hydrogen, optionally substituted alkyl: a group OR 11 and NR 12 R 13 ;
R 5 , R 7 and R 8 are independently selected from the group consisting of hydrogen, an optionally substituted alkyl, and halogen,
R 9 and R 10 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, cycloalkyl and cycloaralkyl; or R 9 and R 10 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
R 11 is selected from the group consisting of hydrogen, an alkali metal, a negative charge and optionally substituted alkyl;
R 12 and R 13 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, aralkyl, aryl, cycloalkyl and cycloaralkyl; or R 12 and R 13 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring;
with the proviso that when R 9 and R 10 are taken together to form a piperazinyl ring, R 7 is Cl, R 3 is OR 11 , R 11 is H, R 5 and R 8 are H, then R 1 is not Et; with the further proviso that when R 9 and R 10 taken together to form 4-methylpiperazine, R 7 is Cl, R 3 is OR 11 , R 11 is H, and R 5 and R 8 are H, then R 1 is not Et; and with the further proviso that when R 9 and R 10 are taken together to form a morpholinyl ring, R 1 , R 2 , R 5 , R 7 , R 8 are H, R 3 is NR 12 R 13 and either R 12 or R 13 is H, the other is not n-butyl.
37 . The method of claim 20 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
38 . The method of claim 21 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
39 . The method of claim 22 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
40 . The method of claim 23 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
41 . The method of claim 24 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
42 . The method of claim 25 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
43 . The method of claim 26 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
44 . The method of claim 27 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
45 . The method of claim 28 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
46 . The method of claim 29 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
47 . The method of claim 30 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
48 . The method of claim 31 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
49 . The method of claim 32 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
50 . The method of claim 33 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
51 . The method of claim 34 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
52 . The method of claim 35 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.
53 . The method of claim 36 wherein the compound is 7-Chloro-1-ethyl-6-1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (R)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; (S)-7-Chloro-1-ethyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(1-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-aminoindanyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(benzylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(phenethyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[3-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[2-methoxy(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-bromo(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-[4-chloro(phenethylamino)]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(3-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(4-phenylbutyl-2-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenylpropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-ethyl-6-(2-phenoxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or 7-Chloro-1-methyl-6-(1,2,3,4-tetrahydronaphthyl-1-amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; or a pharmaceutically acceptable salt, prodrug or solvate thereof.Join the waitlist — get patent alerts
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