# US 8,569,484 B2 · Heterocyclic urea derivatives and methods of use thereof

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- Number: US 8,569,484 B2
- Document ID: US8569484B2
- Status: Granted
- Kind: B2
- Application number: 13/322,717
- Filed: 2010-05-28
- Published: 2012-05-17
- Granted: 2013-10-29
- Earliest claimed: 2009-05-29
- Assignees: AstraZeneca AB
- Applicants: Neil Bifulco; Allison Laura Choy; Olga Quiroga; Brian Alan Sherer
- Inventors: Neil Bifulco; Allison Laura Choy; Olga Quiroga; Brian Alan Sherer
- Web page: https://patentgrep.com/patent/US8569484B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/02: Nasal agents, e.g. decongestants
- A61P 11/08: Bronchodilators
- A61P 13/02: of urine or of the urinary tract, e.g. urine acidifiers
- A61P 17/00: Drugs for dermatological disorders
- A61P 27/16: Otologicals
- A61P 31/04: Antibacterial agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds of formula (IA) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.

## Claims

### Claim 1

A compound of formula (IA):
or a pharmaceutically acceptable salt thereof, wherein:
X is CH;
X1 is N;
X2 is CR24;
R1 is ethyl;
R2 is hydrogen
R3 is trifluouromethyl or phenyl;
R5 is selected from —OH, ethoxy, 2-hydroxyethoxy, 3-hydroxypropoxy, 2-(phosphonooxy)ethoxy, 3-(phosphonooxy)propoxy, and 2-{[bis(benzyloxy)phosphoryl]oxy}ethoxy;
R6 is selected from hydrogen, C1-6alkyl, C3-14carbocyclyl-L and heterocyclyl-L-;
wherein said C1-6alkl, C3-14carbocyclyl-L-, or heterocyclyl-L- are optionally substituted with one or more R16; and wherein if said heterocyclyl contains an ═N— or a —S— moiety that nitrogen may be optionally substituted by one oxo group and that sulfur may be optionally substituted by one or two oxo groups; and wherein if said heterocyclyl contains an —NH— moiety that nitrogen may be optionally substituted by a group selected from R17;
R16 is a substituent on carbon which, for each occurrence, is independently selected from halo, nitro, cyano, hydroxy, amino, carboxy, carbamoyl, mercapto, sulphamoyl, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C1-6alkoxy, C1-6alkanoyl, C1-6alkanoyloxy, N—(C1-6alkyl)amino, N,N—(C1-6alkyl)2amino, C1-6alkanoylamino, N—(C1-6alkyl)carbamoyl, N,N—(C1-6alkyl)2carbamoyl, C1-6alkylS(O)a— wherein a is 0, 1 or 2, C1-6alkoxycarbonyl, C1-6alkoxycarbonylamino, N—(C1-6alkyl)sulphamoyl, N,N—(C1-6alkyl)2sulphamoyl, C1-6alkylsulphonylamino, C3-6carbocyclyl, heterocyclyl and —OP(═O)(ORa)2, wherein Ra, for each occurrence is independently H or a C1 -6alkyl; wherein said carbamoyl, C1-6alkyl, C2-6alkenyl, C2-6alkoxy, C1-6alkanoyl, C1-6alkanoyloxy, N—(C1-6alky)amino, N N—(C1-6alkyl)2amino, C1-6alkanoylamino, N—(C1-6alkyl)carbamoyl, N,N—(C1-6alkyl)2carbamoyl C1-6alkylS(O)a-wherein a is 0, 1 or 2, C1-6alkoxcarbonyl, C1-6alkoxy carbonylamino, N—(C1-6alkyl)sulphamoyl, N,N—(C1-6alkyl)2sulphamoyl, C1-6alkysulphonylamino, C3-6carbocyclyl and heterocyclyl independently of each other may be optionally substituted on one or more carbon by one or more R19; and wherein if said heterocyclyl contains an —NH— moiety that nitrogen may be optionally substituted by a group selected from R20; and wherein if said heterocyclyl contains an ═N— or a —S— moiety that nitrogen may be optionally substituted by one oxo group and that sulfur may be optionally substituted by one or two oxo groups;
R17 and R20, for each occurrence, are independently selected from C1-6alkyl, C3-6cycloalkyl, C1-6alkanoyl, C1-6alkylsulphonyl, C1-6alkoxycarbonyl, carbamoyl, N—(C1-6alkyl)carbamoyl, N,N—(C1-6alkyl)carbamoyl, benzyl, benzyloxycarbonyl, benzoyl and phenylsulphonyl; wherein said C1-6alkyl C3-6cycloalky, C1-6alkanoyl, C1-6alkylsulphonyl, C1-6alkoxycarbonyl, carbamoyl, N—(C1-6alkyl)carbamoyl, N, N—(C1-6alkyl)carbamoyl, benzyl, benzyloxycarbonyl, benzoyl and phenylsuphonyl independently of each other may be optionally substituted on carbon by one or more R23;
R19 and R23, for each occurrence, are independently selected from halo, nitro, cyano, hydroxy, trifluoromethoxy, trifluoromethyl, phenyl, morpholinyl, piperazinyl, piperidinyl, amino, carboxy, carbamoyl, mercapto, sulphamoyl, C1-6alkyl, C1-6alkoxy, acetyl, acetoxy, methylamino, ethylamino, dimethylamino, diethylamino, dipropylamino, N-methyl-N-ethylamino, acetylamino, N-methylcarbamoyl, N-ethylcarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N-methyl-N-ethylcarbamoyl, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, mesyl, ethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulphamoyl, N-ethylsulphamoyl, N,N-dimethylsulphamoyl, N,N-diethylsulphamoyl and N-methyl-N-ethylsulphamoyl;
R24 is selected from hydrogen, halo, nitro, cyano, hydroxy, amino, mercapto, heterocyclyl, C1-6alkyl, C2-6alkenyl, C2-6alkenyl, C1-6alkoxy, N—(C1-6alkyl)amino, N,N—(C1-6alkyl)2amino, and C1-6alkylsulfanyl; wherein said heterocyclyl, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C1-6alkoxy, N—C1-6alkyl)amino, N,N—(C1-6alkyl)2amino and C1-6alkylsulfanyl may be optionally substituted on one or more carbon by one or more R25; wherein if said heterocyclyl contains an —NH—moiety that nitrogen may be optionally substituted by C1-6 alkyl;
R25 is a substituent on carbon which, for each occurrence, is independently selected from halo, nitro, cyano, hydroxy, amino, carboxy, carbamoyl, mercapto, sulphamoyl, C2-6alkenyl, C2-6alkynyl, C1-6alkoxy, C1-6alkanoyl, C1-6alkanoyloxy, N—(C1-6alkyl)amino, N,N—(C1-6alkyl)2amino, C1-6alkanoylamino, N—(C1-6alkyl)carbamoyl, N,N—(C1-6alkyl)2carbamoyl, C1-6alkylS(O)a— wherein a is 0, 1 or 2, C1-6alkoxycarbonyl, C1-6alkoxycarbonylamino, N—(C1-6alkyl)sulphamoyl, N,N—(C1-6alkyl)2sulphamoyl, C1-6alkylsulphonylamino, C3-6carbocyclyl and heterocyclyl; wherein said carbamoyl, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C-6alkoxy, C1-6alkanoyl, C1-6alkanoyloxy, N—(C1-6alkyl)amino, N,N—(C1-6alkyl)2amino, C1-6alkanoylamino, N—(C1-6alkyl)carbamoyl, N,N—(C1-6alkyl)2carbamoyl, C1-6alkylS(O)a— wherein a is 0, 1 or 2, C1-6alkoxycarbonyl, C1-6alkoxycarbonylamino N—(C1-6alkyl)sulphamoyl, N,N—(C1-6alkyl)2sulphamoyl, C1-6alkylsulphonylamino, C3-6carbocyclyl and heterocyclyl may be optionally substituted on one or more carbon by one or more R26; and wherein if said heterocyclyl contains an —NH— moiety that nitrogen may be optionally substituted by a group selected from R27; and wherein if said heterocyclyl contains an ═N— or a —S— moiety that nitrogen may be optionally substituted by one oxo group and that sulfur may be optionally substituted by one or two oxo groups;
R26 and R28, for each occurrence, are independently selected from halo, nitro, cyano, hydroxy, trifluoromethoxy, trifluoromethyl, amino, carboxy, carbamoyl, mercapto, sulphamoyl, C1 -6alkyl, C1-6alkoxy, acetyl, acetoxy, methylamino, ethylamino, dimethylamino, diethylamino, N-methyl-N-ethylamino, acetylamino, N-methylcarbamoyl, N-ethylcarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N-methyl-N-ethylcarbamoyl, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, mesyl, ethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulphamoyl, N-ethylsulphamoyl, N,N-dimethylsulphamoyl, N,N-diethylsulphamoyl and N-methyl-N-ethylsulphamoyl;
R27, for each occurrence, is independently selected from C1-6alkyl, C3-6cycloalkyl, C1-6alkanoyl, C1-6alkylsulphonyl, C1-6alkoxycarbonyl, carbamoyl, N—(C1-6alkyl)carbamoyl, N,N—(C1-6alkyl)2carbamoyl, benzyl, benzyloxycarbonyl, benzoyl and phenylsulphonyl; wherein said C1-6alkyl, C3-6cycloakyl, C1-6alkylsulphonyl, C1-6alkoxycarbonyl, carbamoyl, N—(C1-6alkyl)carbamoyl, N,N—(C1-6alkyl)2carbamoyl, benzyl, benzyloxycarbonyl, benzoyl and phenylsulphonyl may be optionally substituted on carbon by one or more R28; and
L is a direct bond or a C1-6alkylene.

### Claim 2 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R6 is a C1-6alkyl which is substituted on one or more carbon atoms with one or more independently selected R16.

### Claim 3 (depends on 2)

The compound of claim 2, wherein R6, or a pharmaceutically acceptable salt thereof, is selected from 2-hydroxyethyl, ethyl, 1,3-dimethoxypropan-2-yl, 3,3-dimethylbutyl, 2-methoxyethyl,1-hydroxy-4-methyl-pentan-2-yl, 2-(N,N-dimethylamino)-ethyl, 1-hydroxy-3,3-dimethyl-butan-2-yl, 2-(phosphonooxy)ethoxy, 1-(phosphonooxy)-4-methyl-pentan-2-yl, 2-{[bis(benzyloxy)phosphoryl]oxy}ethyl and 1-{[(benzyloxy)(hydroxy)phosphoryl]oxy}-4-methyl-penan-2-yl.

### Claim 4 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R6 is C3-6cycloalkyl.

### Claim 5 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R6 is a heterocyclyl-L-; wherein said heterocyclyl is optionally substituted on one or more carbon atoms with one or more R16; and wherein if said heterocyclyl contains an ═N— or a —S— moiety that nitrogen may be optionally substituted by one oxo group and that sulfur may be optionally substituted by one or two oxo groups; and wherein if said heterocyclyl contains an —NH— moiety that nitrogen may be optionally substituted by a group selected from R17.

### Claim 6 (depends on 5)

The compound of claim 5, or a pharmaceutically acceptable salt thereof, wherein R6 is selected from 2-(1-methyl-piperidin-4-yl)-ethyl, 1-ethylpyrrolidin-2-yl)methyl, (1-methyl-1 H-imidazol-4-yl)methyl, 2-morpholinopropyl, (2-(diethylamino)ethyl)piperidin-3-yl, cyclohexyl, 1-(2-morpholino-ethyl)-piperidin-3-yl, 1-methyl -piperidin-4-ylmethyl and 1-(tert-butoxycarbonyl)-piperidin-3-yl, piperidin-3-yl.

### Claim 7 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, represented by the following formula:

### Claim 8 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient or carrier.

### Claim 9 (depends on 1)

The compound of claim 1, wherein the compound is selected from the group consisting of:
Ethyl 6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
Ethyl 1-cyclopropyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
Ethyl 6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-1-[(2S)-1-hydroxy-4-methylpentan-2-yl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
Ethyl 6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-1-[(2S)-1-hydroxy-3,3-dimethylbutan-2-yl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
1-Ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
1-Cyclopropyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin -3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluorornethyl)-1,3-thiazol-2-yl]pyridin-3-yl}1-1-[(2S)-1-hydroxy-4-methylpentan-2-yl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluorornethyl)-1,3-thiazol-2-yl]pyridin-3-yl}1-1-[(2S)-1-hydroxy-3,3-dimethylbutan-2-yl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
1-(2-{[bis(benzyloxy)phosphoryl]oxy}ethyl)-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}1-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
6-{6-[(ethylcarbamoyl)amino ]-4-[4-(trifluorornethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1-[2-(phosphonooxy)ethyl]-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
Ethyl 1[2-(dimethylamino)ethyl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
1-[2-(dimethylamino)ethyl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
2-hydroxyethyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
3-hydroxypropyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
2-{[bis(benzyloxy)phosphoryl]oxy}ethyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
2-(phosphonooxy)ethyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
3-{[Bis(benzyloxy)phosphoryl]oxy}propyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
3-(Phosphonooxy)propyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluorornethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
Ethyl 1-[(2S)-1-{[(benzyloxy)(hydroxy)phosphoryl]oxy}-4-methylpentan-2-yl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
1-[(2S)-1-{[(benzyloxy)(hydroxy)phosphoryl]oxy}-4-methylpentan-2-yl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluorornethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-1-[(2S)-4-methyl-1-(phosphonooxy)pentan-2-yl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
(R)-ethyl 1-(1-(tert-butoxycarbonyl)piperidin-3-yl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethypthiazol-2-yl)pyridin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
(R)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethypthiazol-2-yl)pyridin-3-yl)-4-oxo-1-(piperidin-3-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
(R)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethypthiazol-2-yl)pyridin-3-yl)-1-(1-(2-morpholinoethyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylat;
(R)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethypthiazol-2-yl)pyridin-3-yl)-1-(1-(2-morpholinoethyl)piperidin-3-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;
Ethyl 1-(2-{[bis(benzyloxy)phosphoryl]oxy}ethyl)-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-y}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
(S)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(1-(2-morpholinoethyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
(S)-1-((1-ethylpyrrolidin-2-yl)methyl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-y1)pyridin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
(R)-1-((1-ethylpyrrolidin-2-yl)methyl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-y1)pyridin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
(S)-1-(1-(2-(diethylamino)ethyl)piperidin-3-yl)-6-(6-(3-ethylureido)-4-(4-isobutylthiazol-2-yl)pyridin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
(S)-1-(1-(2-(diethylamino)ethyl)piperidin-3-yl)-6-(6-(3-ethylureido)-4-(4-phenylthiazol-2-yl)pyridin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
7-(2-(dimethylamino)ethylamino)-1-(((S)-1-ethylpyrrolidin-2-yl)methyl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethypthiazol-2-yl)pyridin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
7-(2-(dimethylamino)ethylamino)-1-ethyl-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol -2-yl)pyridin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
1-ethyl-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
(R)-1-(1-(2-(diethylamino)ethyl)piperidin-3-yl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethypthiazol-2-yl)pyridin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
1-(1,3-dimethoxypropan-2-yl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(2-morpholinoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(1-methylazetidin-3-yI)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;
(S)-1-((1-ethylpyrrolidin-2-yl)methyl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-y1)pyridin-3-yl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
(S)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(1-hydroxy-3,3-dimethylbutan-2-yl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
(S)-7-(3-(aminomethyl)pyrrolidin-1-yl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(2-(4-methylpiperazin-1-yl)ethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;
(S)-7-(3-aminopyrrolidin-1-yl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(2-(4-methylpiperazin-1 -yl)ethyl)-4-oxo-1 ,4-dihydro-1 ,8-naphthyridine-3-carboxylic acid;
7-(3-aminopyrrolidin-1-yl)-1-ethyl-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; and
7-(3-aminopyrrolidin-1-yl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-y1)-1-((S)-1-hydroxy-3,3-dimethylbutan-2-yl)-4-oxo-1 ,4-dihydro-1 ,8-naphthyridine-3-carboxylic acid, or a pharmaceutically acceptable salt thereof.