IP Library Granted Patent US 7,691,850
Granted Patent B2
US 7,691,850 · App. 11/628,705 · Granted Apr 6, 2010

Antibacterial agents

Assignee: Glaxo Group Limited
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Quick Facts
Patent No.
US 7,691,850
App. No.
11/628,705
Granted
Apr 6, 2010
Kind
B2
Abstract

Compounds of formula (I) and derivatives thereof: compositions containing them, their preparation and their use as antibacterials.

Claims (198)

1. A compound of formula (I) or a pharmaceutically acceptable salt thereof:

wherein:

Z 1 , Z 3 , and Z 4 are each independently N or CR 1a ;

Z 2 , Z 5 and Z 6 are each CR 1a ;

R 1 and R 1a are independently at each occurrence hydrogen; cyano; halogen; hydroxy; (C 1-6 )alkoxy unsubstituted or substituted by (C 1-6 )alkoxy, hydroxy, amino, piperidyl, guanidino or amidino any of which is unsubstitued or N-substituted by one or two (C 1-6 )alkyl, acyl, (C 1-6 )alkylsulphonyl, CONH 2 , hydroxy, (C 1-6 )alkylthio, heterocyclylthio, heterocyclyloxy, arylthio, aryloxy, acylthio, acyloxy or (C 1-6 )alkylsulphonyloxy; (C 1-6 )alkyl; (C 1-6 )alkylthio; trifluoromethyl; trifluoromethoxy; nitro; azido; acyl; acyloxy; acylthio; (C 1-6 )alkylsulphonyl; (C 1-6 )alkylsulphoxide; arylsulphonyl; arylsulphoxide; or an amino, piperidyl, guanidino or amidino group unsubstituted or N-substituted by one or two (C 1-6 )alkyl, acyl or (C 1-6 )alkylsulphonyl groups;

or R 1 and R 1a of Z 2 , or R 1 and R 1a of Z 1 together form ethylenedioxy;

A is CR 2 R 3 ;

R 2 is hydrogen; halogen; hydroxy; acyloxy; or (C 1-6 )alkoxy; and R 3 is hydrogen;

W 1 is CR 4 R 5 ;

R 4 is hydrogen; halogen; hydroxy; (C 1-6 )alkyl; (C 1-6 )hydroxyalkyl; C(═O)—NR 1d R 1d′ ; (C 1-6 )alkoxy; NR 1b R 1b′ or acyloxy; and R 5 is hydrogen or (C 1-6 )alkyl;

or R 4 and R 5 together are ═N—OH;

R 1b and R 1b′ are each independently hydrogen; (C 1-6 )alkyl; aryl; heteroaryl; or together with the nitrogen to which they are attached form an aziridine, azetidine, pyrrolidine, piperidine or hexamethyleneimine ring (wherein said aziridine, azetidine, pyrrolidine, piperidine or hexamethyleneimine ring is optionally substituted with 1 to 3 substitutents selected from halogen, (C 1-6 )alkyl, hydroxy and aryl);

R 1d and R 1d′ are each independently hydrogen or (C 1-6 )alkyl;

W 2 is CR 6 ;

R 6 is hydrogen; halogen; hydroxy; (C 1-6 )alkyl; NR 1c R 1c′ ; acyloxy; or (C 1-6 )alkoxy;

R 1c and R 1c′ are each independently hydrogen; (C 1-6 )alkyl; aryl; heteroaryl; or together with nitrogen to which they are attached form an aziridine, azetidine, pyrrolidine, piperidine or hexamethyleneimine ring (wherein said azidirine, azetidine, pyrrolidine, piperidine or hexamethyleneimine ring is optionally substituted with 1 to 3 substituents selected from halogen, (C 1-6 )alkyl, hydroxy and aryl);

B is CR 7 R 8 or a bond;

R 7 and R 8 are each independently hydrogen or (C 1-6 )alkyl;

R 9 is hydrogen; aryl; heteroaryl; (C 1-6 )alkyl unsubstituted or substituted by one or two (C 1-6 )alkoxy, acyloxy, carboxy, hydroxy, amino, piperidyl, piperazinyl, morpholino, guanidino, or amidino, any of which is unsubstituted or N-substituted by one or two aryl, heteroaryl, halogen, unsubstituted (C 1-6 )alkyl, acyl, (C 1-6 )alkylsulphonyl, arylsulphonyl, hydroxy, (C 1-6 )alkylthio, heterocyclylthio, heterocyclyloxy, arylthio, aryloxy, acylthio, acyloxy, or (C 1-6 )alkylsulphonyloxy; (C 1-6 )alkylcarbonyl; or (C 2-6 )alkenylcarbonyl;

R 10 is a group —U—R 11 where:

R 11 is:

R 12 , R 14 and R 15 are at each occurrence independently selected from: H; (C 1-4 )alkylthio; halo; (C 1-4 )alkyl; (C 2-4 )alkenyl; hydroxy; hydroxy(C 1-4 )alkyl; mercapto(C 1-4 )alkyl; (C 1-4 )alkoxy; trifluoromethoxy; nitro; cyano; carboxy; and amino or aminocarbonyl unsubstituted or substituted by (C 1-4 )alkyl;

R 13 is at each occurrence independently hydrogen; trifluoromethyl; (C 1-4 )alkyl unsubstituted or substituted by hydroxy, carboxy, (C 1-4 )alkoxy, (C 1-6 )alkylthio, halo or trifluoromethyl; (C 2-4 )alkenyl; or aminocarbonyl wherein the amino group is optionally substituted with (C 1-4 )alkyl;

U is C(═O); SO 2 ; or CR 16 R 17 ; and

R 16 and R 17 are independently selected from H; aryl; heteroaryl; (C 1-6 )alkyl; (C 1-6 )alkyl substituted by (C 1-6 )alkoxy, hydroxy, amino, piperidyl, piperazinyl, morpholino, guanidino, or amidino, any of which is substituted or N-substituted by one or two H, aryl, heteroaryl, halogen, cyano, CF 3 , (C 1-6 )alkyl, acyl, (C 1-6 )alkylsulphonyl, arylsulphonyl, hydroxy, (C 1-6 )alkylthio, heterocyclylthio, heterocyclyloxy, arylthio, aryloxy, acylthio, acyloxy, or (C 1-6 )alkylsulphonyloxy; (C 1-6 )alkoxy-substituted (C 1-6 )alkyl; hydroxy-substituted(C 1-6 )alkyl; amino-substituted(C 1-6 )alkyl, which is N-substituted by one or two (C 1-6 )alkyl, acyl, (C 1-6 )alkylsulphonyl, or arylsulphonyl; (C 1-6 )alkylcarbonyl; (C 2-6 )alkenylcarbonyl; (C 1-6 )alkoxycarbonyl; CO 2 H; and CF 3 .

2. The compound according to claim 1 , wherein Z 1 and Z 4 are N and Z 3 is CR 1a .

3. The compound according to claim 1 , wherein R 1 is OCH 3 .

4. The compound according to claim 1 , wherein R 1a is at each occurrence independently hydrogen, halogen or cyano.

5. The compound according to claim 2 , wherein R 1a of Z 2 , Z 3 and Z 5 are each hydrogen; R 1a of Z 6 is hydrogen, halogen or cyano; and R 1 is OCH 3 .

6. The compound according to claim 1 , wherein R 2 is hydrogen or hydroxy.

7. The compound according to claim 1 , wherein B is CH 2 .

8. The compound according to claim 1 , wherein R 4 is hydroxyl and R 5 is hydrogen.

9. The compound according to claim 1 , wherein R 9 is hydrogen.

10. The compound according to claim 1 , wherein U is CH 2 .

11. The compound according to claim 1 , wherein R 11 is:

4H-Pyrido[3,2-b][1,4]thiazin-3-oxo-6-yl;

4H-Pyrido[3,2-b][1,4]oxazin-3-oxo-6-yl;

7-Chloro-4H-pyrido[3,2-b]oxazin-3-oxo-6-yl; or

7-Methyl-4H-pyrido[3,2-b][1,4]thiazin-3-oxo-6-yl.

12. The compound according to claim 1 , wherein the compound of formula (I) is:

a) 6-({[((3S)-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

b) 6-({[((3R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

f) 6-({[((3R)-1-{2-[3,8-difluoro-6-(methyloxy)-4-quinolinyl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

g) 6-({[((3S)-1-{2-[3-fluoro-6-(methyloxy)-4-quinolinyl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

h) 6-({[((3S)-1-{2-[3-fluoro-6-(methyloxy)-4-quinolinyl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

j) 7-chloro-6-({[((3R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

m) 6-(methyloxy)-4-{2-[(3S)-3-({[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methyl]amino}methyl)-1-pyrrolidinyl]ethyl}-3-quinolinecarbonitrile;

o) 6-(methyloxy)-4-{2-[(3S)-3-({[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}methyl)-1-pyrrolidinyl]ethyl}-3-quinolinecarbonitrile;

p) 6-(methyloxy)-4-{2-[(3S)-3-({[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methyl]amino}methyl)-1-pyrrolidinyl]ethyl}-1,5-naphthyridine-3-carbonitrile;

s) 6-({[((3S)-1-{2-[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

t) 6-({[((3S)-1-{2-[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

v) 6-({[((3S)-1-{2-[3,8-difluoro-6-(methyloxy)-4-quinolinyl]ethyt}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

w) 6-({[((3S)-1-{2-[3,8-difluoro-6-(methyloxy)-4-quinolinyl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

y) 7-chloro-6-({[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-y]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

z) 6-({[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-y]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

aa) 6-({[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

ac) 6-({[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-7-methyl-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

ad) 6-({[((3S)-1-{(2S)-2-hydroxy-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

ae) 6-({[((3S)-1-{(2S)-2-hydroxy-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)9methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

af) 6-({[((3R)-1-{(2S)-2-hydroxy-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

ag) 6-({[((3R)-1-{(2S)-2-hydroxy-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

ah) 6-({[((3S)-1-{(2R)-2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-2-hydroxyethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

ao) (±)-6-({[(1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

ap) (±)-6-({[(trans-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

aq) 6-({[(trans-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

ar) 6-({[(trans-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

as) (±)-6-({[(trans-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1 ,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

at) 6-({[(trans-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

au) 6-({[(trans-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

av) (±)-6-({[((cis-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

aw) 6-({[((3S,4S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

ax) 6-({[((3R,4R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

ay) 6-({[((3S,4S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

az) 6-({[((3R,4R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

ba) (±)-7-chloro-6-({[((cis-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

bb) 7-chloro-6-({[((3S,4S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

bc) 7-chloro-6-({[((3R,4R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

bh) 6-({[((3S,4S)-1-{2-[3-fluoro-6-(methyloxy)-4-quinolinyl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

bi) 6-({[((3S,4S)-1-{2-[3-fluoro-6-(methyloxy)-4-quinolinyl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

bj) (±)-6-({[((cis-3,4)-4-hydroxy-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

bk) 6-({[((3S,4S)-4-hydroxy-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

bl) (±)-6-({[((cis-3,4)-4-hydroxy-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

bm) 6-({[((3S,4S)-1-{2-[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

bn) 6-({[((3S,4S)-1-{2-[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

bp) (±)-6-[({[(cis-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-(methyloxy)-3-pyrrolidinyl]methyl)amino}methyl]-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

bq) (±)-6-[({[(cis-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-(methyloxy)-3-pyrrolidinyl]methyl}amino)methyl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

br) (±)-6-({[(3-fluoro-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

bt) (±)-6-({[((3S,4R)-4-fluoro-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

bu) (±)-6-({[((3S,4S)-4-fluoro-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

bv) (±)-6-({[(1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-methyl-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

bw) (±)-6-({[(1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-methyl-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

bx) (±)-6-({[(1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-4-methyl-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

by) (±)-6-({[(1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-4-methyl-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

bz) (±)-6-({[(1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-methyl -3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

ca) (±)-6-({[(1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-methyl -3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

cd) (±)-4-{2-[3-methyl-3-({[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methyl]amino}methyl)-1-pyrrolidinyl]ethyl}-6-(methyloxy)-3-quinolinecarbonitrile;

cf) 6-({[1-((3R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)-1-methylethyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

ch) N-[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]lethyl}-3-pyrrolidinyl)methyl]-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxamide;

ci) N-[((3S)-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxamide;

cj) N-[((3S,4S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxamide;

ck) (±)-N-[((cis-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]-N-methyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxamide;

cl) (±)-N-[(1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]-N-methyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxamide;

cn) 6-({[((3S,4S)-1-{2-[8-fluoro-6-(methyloxy)-4-quinolinyl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

co) 6-({[((3S,4S)-1-{2-[8-fluoro-6-(methyloxy)-4-quinolinyl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

cp) 6-({[((3S,4S)-1-{2-[6-fluoro-5-(methyloxy)-4-quinolinyl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

cq) 6-({[((3S,4S)-1-{2-[6-fluoro-5-(methyloxy)-4-quinolinyl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

cr) 6-({[((3S,4S)-1-{2-[3,8-difluoro-6-(methyloxy)-4-quinolinyl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

cs) 6-({[((3S,4S)-1-{2-[3,8-difluoro-6-(methyloxy)-4-quinolinyl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

ct) 6-{[({(3S,4S)-1-[2-(9-chloro-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-10-yl)ethyl]-4-hydroxy-3-pyrrolidinyl}methyl)amino]methyl}-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

cu) 6-{[({(3S,4S )-1-[2-(9-chloro-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-10-yl)ethyl]-4-hydroxy-3-pyrrolidinyl}methyl)amino]methyl}-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

cv) 6-{[({(3S,4S)-1-[2-(2,3-dihydro[1,4]dioxino[2,3-f]quinolin-10-yl)ethyl]-4-hydroxy-3-pyrrolidinyl}methyl)amino]methyl}-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

cw) 6-({[((3S,4S)-4-hydroxy-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

cy) 7-chloro-6-({[((3S,4S)-4-hydroxy-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

dc) 6-({[((3S,4S)-4-hydroxy-1-{2-[6-(methyloxy)-4-quinolinyl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

dd) 6-({[((3S,4S)-4-hydroxy-1-{2-[6-(methyloxy)-4-quinolinyl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

dg) N-[((3S,4S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carboxamide;

dh) (±)-6-[({[(3R,4S)/(3S,4R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-(hydroxymethyl)-3-pyrrolidinyl]methyl}amino)methyl]-2H-pyrido[3,2-b][1,4]thiazin -3(4H)-one;

di) (±)-6-[({[(3R,4S)/(3S,4R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-(hydroxymethyl)-3-pyrrolidinyl]methyl}amino)methyl]-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

dj) 6-[({[(3R,4S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-(hydroxymethyl)-3-pyrrolidinyl]methyl}amino)methyl]-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

dk) (±)-6-[({[(3S,4R)/(3S,4R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-(hydroxymethyl)-3-pyrrolidinyl]methyl}amino)methyl]-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

dm) 6-[({[(3R,4Z)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-(hydroxyimino)-3-pyrrolidinyl]methyl}amino)methyl]-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

dn) 6-[({[(3R,4Z)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-(hydroxyimino)-3-pyrrolidinyl]methyl}amino)methyl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

dp) (±)-(3S,4S)/(3R,4R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-({[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methyl]amino}methyl)-3-pyrrolidinecarboxamide;

dq) (±)-(3S,4S)/(3R,4R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-({[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}methyl)-3-pyrrolidinecarboxamide;

ds) 4-{2-[(3S,4S)-3-hydroxy-4-({[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methyl]amino}methyl)-1-pyrrolidinyl]ethyl}-6-(methyloxy)-1,5-naphthyridine-3-carbonitrile;

dt) 4-{2-[(3S,4S)-3-hydroxy-4-({[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}methyl)-1-pyrrolidinyl]ethyl}-6-(methyloxy)-1,5-naphthyridine-3-carbonitrile;

dv) (±)-6-{[((3S,4R)/(3R,4S)-4-hydroxy-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)amino]methyl}-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one; or

dw) (±)-6-{[((3S,4R)/(3R,4S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)amino]methyl}-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one.

13. A pharmaceutical composition comprising the compound according to claim 1 and at least one pharmaceutically acceptable excipient.

14. The compound according to claim 1 , wherein:

Z 1 and Z 4 are N;

Z 3 is CR 1a ;

R 1 is OMe;

R 1a of Z 2 , Z 3 , and Z 5 are hydrogen;

R 1a of Z 6 is hydrogen, fluoro, chloro, or cyano;

R 2 is hydrogen or hydroxy;

R 4 is hydrogen, hydroxy, fluoro, methyl, or methoxy;

R 5 is hydrogen or methyl;

R 6 is hydrogen; hydroxy; fluoro; or methyl;

R 7 and R 8 are independently hydrogen or methyl;

R 9 is hydrogen or methyl; and

U is CH 2 ; SO 2 or C(═O).

15. The compound according to claim 14 , wherein R 11 is 4H-Pyrido[3,2-b][1,4]thiazin-3-oxo-6-yl, 4H-Pyrydo[3,2-b]oxazin-3-oxo-6-yl, 7-Chloro-4H-pyrido[3,2-b]oxaxin-3-6-yl, or 7-Methyl-4H-pyrido[3,2-b][1,4]thiazin-3-oxo-6-yl.

16. The compound according to claim 1 , wherein the compound of formula (I) is selected from:

6-({[((3S)-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[((3R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[((3R)-1-{2-[3,8-difluoro-6-(methyloxy)-4-quinolinyl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[((3S)-1-{2-[3-fluoro-6-(methyloxy)-4-quinolinyl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[((3S)-1-{2-[3-fluoro-6-(methyloxy)-4-quinolinyl]ethyl}-3-pyrrotidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

7-chloro-6-({[((3R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-(methyloxy)-4-{2-[(3S)-3-({[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b1][1,4]thiazin-6-yl)methyl]amino}methyl)-1-pyrrolidinyl]ethyl}-3-quinolinecarbonitrile;

6-(methyloxy)-4-{2-[(3S)-3-({[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}methyl)-1-pyrrolidinyl]ethyl}-1,5-naphthyridine-3-carbonitrile;

6-(methyloxy)-4-{2-[(3S)-3-({[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methyl]amino}methyl)-1-pyrrolidinyl]ethyl}-1,5-naphthyridine-3-carbonitrile;

6-({[((3S)-1-{2-[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[((3S)-1-{2-[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-({[((3S)-1-{2-[3,8-difluoro-6-(methyloxy)-4-quinolinyl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-({[((3S)-1-{2-[3,8-difluoro-6-(methyloxy)-4-quinolinyl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

7-chloro-6-({[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-({[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-({[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

-({[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[((3S)-1-{(2S)-2-hydroxy-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-({[((3R)-1-{(2S)-2-hydroxy-2-[6-methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[((3R)-1-{(2S)-2-hydroxy-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-({[((3R)-1-{(2S)-2-hydroxy-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-({[((3S)-1-{(2R)-2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-2-hydroxyethyl}-3-pyrrolidinyl )methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

(±)-6-({[(trans-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[(trans-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl )methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one (Enantiomer 1);

6-({[(trans-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl )methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one (Enantiomer 2);

(±)-6-({[(trans-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl )methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-({[(trans-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl )methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (Enantiomer 1);

6-({[(trans-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl )methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (Enantiomer 2);

(±)-6-({[((cis-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-][1,4]thiazin-3(4H)-one;

6-({[((3S,4S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[((3R,4R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[((3S,4S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-({[((3R,4R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrotidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

(±)-7-chloro-6-({[((cis-3,4)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

7-chloro-6-({[((3S ,4S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

7-chloro-6-({[((3R,4R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-({[((3S,4S)-1-{2-[3-fluoro-6-(methyloxy)-4-quinolinyl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[((3S,4S)-1-{2-[3-fluoro-6-(methyloxy)-4-quinolinyl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

(±)-6-({[((cis-3,4)-4-hydroxy-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]lethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[((3S,4S)-4-hydroxy-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

(±)-6-({[((cis-3,4)-4-hydroxy-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrotidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-({[((3S,4S)-1-{2-[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-({[((3S,4S)-1-{2-[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[((3S,4S)-1-{2-[8-fluoro-6-(methyloxy)-4-quinoliny]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[((3S,4S)-1-{2-[8-fluoro-6(methyloxy)-4-quinoliny]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-({[((3S,4S)-1-{2-[3,8-difluoro-6-(methyloxy)-4-quinolinyl]ethyl}-4-hydroxy-3-pyrroidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-({[((3S,4S)-1-{2-[3,8-difluoro-6-(methyloxy)-4-quinolinyl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[((3S,4S)-4-hydroxy-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

7-chloro-6-({[((3,S4S)-4-hydroxy-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

6-({[((3S,4S)-4-hydroxy-1-{2-[6-(methyloxy)-4-quinolinyl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one;

6-({[((3S,4S)-4-hydroxy-1-{2-[6-(methyloxy)-4-quinolinyl]ethyl}-3-pyrrolidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;

4-{2-[(3S,4S)-3-hydroxy-4-({[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methyl]amino}methyl)-1-pyrrolidinyl]ethyl}-6-(methyloxy)-1,5-naphthyridine-3-carbonitrile; and

4-{2-[(3S,4S)-3-hydroxy-4-({[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}methyl)-1-pyrrolidinyl]ethyl}-6-(methyloxy)-1,5-naphthyridine-3-carbonitrile.

17. A pharmaceutical composition comprising the compound according to claim 16 and at least one pharmaceutically acceptable excipient.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 16, 2007
From: MILLER, WILLIAM HENRY; PENDRAK, ISRAIL; SEEFELD, MARK ANDREW
To: GLAXO GROUP LIMITED
Reel/Frame 018773/0540 →
Continuity (2)
Provisional Application 6057987300 · Jun 15, 2004
Related Publication 20070287701A1 · Dec 13, 2007