IP Library Granted Patent US 9,271,978
Granted Patent B2
US 9,271,978 · App. 14/134,793 · Granted Mar 1, 2016

Heterocyclic compounds as bromodomain inhibitors

Inventors: Shuang Liu (Schenectady, NY); Bryan Cordell Duffy (Glenmont, NY); John Frederick Quinn (Albany, NY); May Xiaowu Jiang (Guilderland, NY); Ruifang Wang (Schenectady, NY); Gregory Scott Martin (Colonie, NY); He Zhao (Madison, CT); Bruce Francis Molino (Slingerlands, NY); Peter Ronald Young (San Francisco, CA)
Assignee: Zenith Epigenetics Corp.
A61K31/501A61K31/4439A61K31/496A61K31/50A61K45/06C07D237/04C07D401/12C07D413/04C07D413/14C07D417/04
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,271,978
App. No.
14/134,793
Granted
Mar 1, 2016
Kind
B2
Abstract

The present disclosure relates to compounds, which are useful for inhibition of BET protein function by binding to bromodomains, and their use in therapy.

Claims (184)

1. A compound of Formula II:

or a stereoisomer, tautomer, pharmaceutical acceptable salt, or hydrate thereof, wherein:

W 1 is selected from N and CR 5 ;

W 2 is CR 4 ;

W 3 is CR 3 ;

each W may be the same or different from each other;

R 1 is a carbocycle or heterocycle,

wherein the carbocycle is a saturated or unsaturated cycloalkyl optionally substituted with alkoxy, aryloxy, alkyl, alkenyl, alkynyl, amide, amino, aryl, arylalkyl, carbamate, carboxy, cyano, cycloalkyl, ester, ether, formyl, halogen, haloalkyl, hydroxyl, ketone, nitro, phosphate, sulfide, sulfinyl, sulfonyl, sulfonic acid, sulfonamide and thioketone;

wherein the heterocycle is optionally substituted with alkoxy, aryloxy, alkyl, alkenyl, alkynyl, amide, amino, aryl, arylalkyl, carbamate, carboxy, cyano, cycloalkyl, ester, ether, formyl, halogen, haloalkyl, heteroaryl, heterocyclyl, hydroxyl, ketone, nitro, phosphate, sulfide, sulfinyl, sulfonyl, sulfonic acid sulfonamide and thioketone, and

wherein the cycloalkyl or heterocycle may be fused to other cycloalkyl, aryl, or heterocyclyl groups;

V is an optionally substituted isoxazole;

wherein V is optionally substituted with alkyl (C 1 -C 4 ), alkoxy(C 1 -C 4 ), amino, —NHC(O)NHalkyl), halogen, amide, —CF 3 , CN, —N 3 , ketone (C 1 -C 4 ), —S(O)Alkyl(C 1 -C 4 ), —SO 2 alkyl(C 1 -C 4 ), -thioalkyl(C 1 -C 4 ), carboxyl, ester, each of which may be optionally substituted with hydrogen, F, Cl, Br, —OH, —NH 2 , —NHMe, —OMe, —SMe, oxo, and thio-oxo;

R 3 , R 4 , and R 5 are each independently selected from hydrogen, alkyl, —OH, —NH 2 , thioalkyl, alkoxy, ketone, ester, carboxylic acid, urea, carbamate, carbonate, amino, amide, halogen, carbocycle, heterocycle, sulfone, sulfoxide, sulfide, sulfonamide, and —CN,

R 3 and R 4 may be connected to form an optionally substituted 5-, 6-, or 7-membered carbocycle or heterocycle;

X is selected from O and S;

A is selected from —CR x R y —, C═O, —C(O)CR x R y —, —CR x R y CR z R v —, —SO 2 —, —CR x R y CR z R v O—, —CR x R y CR z R v N—, —CR x R y CR z R v S—, and —CR x R y CR z R v CR Q R R —,

with the proviso that R x and R y cannot both be an unsubstituted phenyl ring,

and with the proviso that if A is —CH 2 CH 2 O— then R 1 is not

R x , R y , R z , R Q and R R are each independently selected from hydrogen, alkyl(C 1 -C 8 ), halogen, —OH, —CF 3 , amino, alkoxy (C 1 -C 8 ), carboxyl, —CN, sulfone, sulfoxide, carbocycle, and heterocycle, or two substituents selected from R x , R y , R z , R v , R Q and R R may form an oxo or thio-oxo group, or

two substituents selected from R x , R y , R z , R v , R 5 , and R 1 may be connected in a 5- or 6-membered ring to form a bicyclic carbocycle or bicyclic heterocycle;

B is selected from —(CR a R b ) n —, —(CR a R b CR c R d )—, —O—, —OCR a R b —, —CR a R b O—, —NH—, —NHCR a R b —, —CR a R b NH—, —S—, —SCR a R b —, —CR a R b S—, —S(O)—, —S(O)CR a R b —, —CR a R b S(O)—, —SO 2 —, —SO 2 CR a R b —, and —CR a R b SO 2 —;

n is selected from 0 and 1, meaning if n=0 then B is absent; and wherein

R a , R b , R c , and R d are each independently selected from hydrogen, alkyl(C 1 -C 3 ), and alkoxy(C 1 -C 3 ).

2. The compound according to claim 1 , wherein V is

3. The compound according to claim 1 , wherein A is selected from C═O and —CR x R y —.

4. The compound according to claim 1 , wherein R 1 is selected from an optionally substituted 3-, 4-, 5-, and 6-membered carbocycle or heterocycle.

5. The compound according to claim 4 , wherein the carbocycle or heterocycle is selected from cyclopropyl, phenyl, pyridyl, thiophene, cyclobutyl, piperidine, piperazine, cyclopentyl, and cyclohexyl.

6. The compound according to claim 4 , wherein R 1 is selected from an optionally substituted 5- and 6-membered carbocycle or heterocycle.

7. The compound according to claim 6 , wherein the carbocycle or heterocycle is selected from phenyl, pyridyl, thiophene, and cyclopentyl.

8. The compound according to claim 7 , wherein R 1 is selected from an optionally substituted phenyl or pyridyl ring.

9. The compound according to claim 1 , wherein B is selected from —(CR a R b ) n —, —O—, —NH—, —S—, —S(O)—, —SO 2 —, where n is 0 or 1, meaning if n=0 then B is absent.

10. A compound selected from:

6-(3,5-Dimethylisoxazol-4-yl)-2-phenethylpyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(pyridin-2-ylmethyl)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(pyrimidin-2-ylmethyl)pyridazin-3(2H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(3-(trifloromethyl)benzyl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(4-(trifluoromethoxy)benzyl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(4-(trifluoromethyl)benzyl)pyridin-2(1H)-one;

1-(4-((Dimethylamino)methyl)benzyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(piperidin-4-ylmethyl)pyridin-2(1H)-one;

5-(3,5-D methylisoxazol-4-yl)-1-((3,5-dimethylisoxazol-4-yl)methyl)pyridin-2(1H)-one;

1-Benzyl-5-(3,5-dimethylisoxazol-4-yl)-4-methylpyridin-2(1H)-one;

4-((5-(3,5-Dimethylisoxazol-4-yl)-2-oxopyridin-1(2H)-yl)methyl)benzamide;

2-Benzyl-6-(3,5-dimethylisoxazol-4-yl)pyridazin-3(2H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(quinoxalin-6-yl)methyl)pyridin-2(1H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(1-phenylethyl)pyridazin-3(2H)-one;

2-Benzyl-4-methyl-6-(5-methylisoxazol-4-yl)pyridazin-3(2H)-one;

2-Benzyl-6-(3,5-dimethylisoxazol-4-yl)-4-ethylpyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(3-fluorobenzyl)pyridazin-3(2H)-one;

2-(3-Chlorobenzyl)-6-(3,5-dimethylisoxazol-4-yl)pyridazin-3(2H)-one;

2-((3-(3,5-Dimethylisoxazol-4-yl)-6-oxopyridazin-1(6H)-yl)methyl)benzonitrile;

2-(4-Chlorobenzyl)-6-(3,5-dimethylisoxazol-4-yl)pyridazin-3(2H)-one;

2-(2-Chlorobenzyl)-6-(3,5-dimethylisoxazol-4-yl)pyridazin-3(2H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(2-fluorobenzyl)pyridin-2(1H)-one;

6-(3,5-Dimethylisoxazol-4H)-2-(2-methylbenzyl)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(4-methylbenzyl)pyridazin-3(2H)-one;

6-(3,6-(3,5-Dimethylisoxazol-4-yl)-2-(3-(trifluoromethyl)benzyl)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(3-fluoro-5-methylbenzyl)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(4-methoxybenzyl)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(1-(2-(trifluoromethyl)phenyl)ethyl)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(3-methoxybenzyl)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(3-(trifluoromethoxy)benzyl)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-((tetrahydro-2H-pyran-4-yl)methyl)pyridazin-3(2H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(1-(2-(trifluoromethyl)phenyl)ethyl)pyridin-2(1H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(2-(trifluoromethoxy)benzyl)pyridazin-3(2H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(2-(trifluoromethoxy)benzyl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(4-methylbenzyl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(3-fluorobenzyl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(1-phenylpropyl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(pyridin-3-ylmethyl)pyridin-2(1H)-one;

2-(Cyclopropylmethyl)-6-(3,5-dimethylisoxazol-4-yl)pyridazin-3(2H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-((6-methylpyridin-2-yl)methyl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(quinolin-8-ylmethyl)pyridin-2(1H)-one;

1-(Cyclopropylmethyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-(Cyclobutylmethyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-(3-(Difluoromethyl)benzyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(2-phenoxyethyl)pyridin-2(1H)-one;

1((5-Chloropyridin-2-yl)methyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-Benzyl-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-Benzyl-5-(5-methylisoxazol-4-yl)pyridin-2(1H)-one;

1-Benzyl-5-(isoxazol-4-yl)pyridin-2(1H)-one;

1-Benzyl-5-(isothiazol-4-yl)pyridin-2(1H)-one;

2-Benzyl-6-((3,5-dimethylisoxazol-4-0)amino)pyridazin-3(2H)-one;

1-Benzyl-5-(3,5-dimethylisoxazol-4-yl)-3-fluoropyridin-2(1H)-one;

1-Benzyl-3-chloro-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-Benzyl-5-(3,5-dimethylisoxazol-4-yl)-3-methylpyridin-2(1H)-one;

1-Benzyl-3-cyclopropyl-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(4-fluorobenzoyl)pyridin-2(1H)-one,

1-(4-Chlorobenzol)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-Benzyl-5-(3,5-dimethylisoxazol-4-yl)-3-(4-fluorophenyl)pyridin-2(1H)-one;

N-(1-Benzyl-5-(3,5-dimethylisoxazol-4-yl)-2-oxo-1,2-dihydropyridin-3-yl)ace amide;

1-Benzyl-5-(3,5-dimethylisoxazol-4-yl)-3-(phenylamino)pyridin-2(1H)-one,

3-Amino-1-benzyl-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-Benzyl-3-(benzylamino)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-Benzyl-5-(3,5-dimethylisoxazol-4-yl)-3-(methylamino)pyridin-2(1H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(4-(trifluoromethoxy)benzyl)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(naphthalen-2-ylmethyl)pyridazin-3(2H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(3-methoxybenzyl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(thiophen-3-ylmethyl)pyridin-2(1H)-one;

1-Benzyl-5-(thiazol-5-yl)pyridin-2(1H)-one;

1-Benzyl-5-(5-methyl-1H-imidazol-4-yl)pyridin-2(1H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(2-fluorobenzyl)-4-methylpyridazin-3(2H)-one;

2-(Cyclopropylmethyl)-6-(3,5-dimethylisoxazol-4-yl)-4-methylpyridazin-3(2H)-one;

2-Benzyl-6-(3,5-dimethyl-1H-pyrazol-4-0)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-4-methyl-2-(pyridin-4-yl)methyl)pyridazin-3(2H)-one;

2-(Cyclobutylmethyl)-6-(3,5-dimethylisoxazol-4-yl)pyridazin-3(2H)-one;

4-((3-(3,5-Dimethylisoxazol-4-yl)-6-oxopyridazin-1(6H)-yl)methyl)-N-methylbenzamide;

2-(2,6-Difluorobenzyl)-6-(3,5-dimethylisoxazol-4-yl)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(4-(trifluoromethyl)benzyl)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(2,4,6-trifluorobenzyl)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(2-fluorobenzyl)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(2-(trifluoromethyl)benzyl)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(1-(2-fluorophenyl)ethyl)pyridazin-3(2H)-one;

2-(2-Chloro-6-fluorobenzyl)-6-(3,5-dimethylisoxazol-4-yl)pyridazin-3(2H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(isoxazol-4-ylmethyl)pyridazin-3(2H)-one;

5-(5-Amino-3-methylisoxazol-4-yl)-1-benzylpyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(1-(4-fluorophenyl)ethyl)pyridin-2(1H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(quinolin-8-ylmethyl)pyridazin-3(2H)-one;

1-(1-(2-Chlorophenyl)ethyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(1-(3-fluorophenyl)ethyl)pyridin-2(1H)-one;

1-(1-(4-Chlorophenyl)ethyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(2-phenylpropan-2-yl)pyridin-2(1H)-one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(thiophen-3-ylmethyl)pyridazin-3(2H)-one;

(R)-6-(3,5-Dimethylisoxazol-4-yl)-2-(1-phenylethyl)pyridazin-3(2H)-one;

(S)-6-(3,5-Dimethylisoxazol-4-yl)-2-(1-phenylethyl)pyridazin-3(2H)-one;

(S)-5-(3,5-Dimethylisoxazol-4-yl)-1-(1-yl)-fluorophenyl)ethyl)pyridin-2(1H)-one;

(R)-5-(3,5-Dimethylisoxazol-4-yl)-1-(1-(4-fluorophenyl)ethyl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(1-(pyridin-2-yl)ethyl)pyridin-2(1H)-one;

1-(1-(3-Chlorophenyl)ethyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one,

1-Benzyl-6-chloro-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-Benzyl-5-(3,5-dimethylisoxazol-4-yl)-6-dimethylpyridin-2(1H)-one:

5-(3,5-Dimethylisoxazol-4-yl)-1-(2-methylbenzyl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(3-methylbenzyl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(2-(trifluoromethyl)benzyl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(1-(2-fluorophenyl)ethyl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(1-phenylethyl)pyridin-2(1H)-one;

1-(3-Chlorobenzyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-(2-Chlorobenzyl)-5-(3,5-dimethylisoxazol-4-0)pyr din-2(1H)-one;

1-(4-Chlorobenzyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(pyridin-4-ylmethyl)pyridin-2(1H)-one,

5-(3,5-Dimethylisoxazol-4-yl)-1-(4-methoxybenzyl)pyridin-2(1H)-one;

1-(3,4-Dimethoxybenzyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(4-fluorobenzyl)pyridin-2(1H)-one;

(S)-5-(3,5-Dimethylisoxazol-4-yl)-1-(1-phenylethyl)pyridin-2(1H)-one;

(R)-5-(3,5-Dimethylisoxazol-4-yl)-1-(1-phenylethyl)pyridin-2(1H)-one;

2-((5-(3,5-Dimethylisoxazol-4-yl)-2-oxopyridin-1(2H)-yl)methyl)benzonitrile;

1-(2,4-Dichlorobenzyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

4-((5-(3,5-Dimethylisoxazol-4-yl)-2-oxopyridin-1(2H)-yl)methyl)benzonitrile;

1-(2,4-Difluorobenzyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-(4-Chloro-2-fluorobenzyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-(2-Chloro-4-fluorobenzyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-(4-Chloro-3-fluorobenzyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(3,4,5-trifluorobenzyl)pyridin-2(1H)-one;

2-((1H-Benzo[d]imidazol-5-yl)methyl)-6-(3,5-dimethylisoxazol-4-yl)pyridazin-3(2H) one;

6-(3,5-Dimethylisoxazol-4-yl)-2-(3,4,5-trifluorobenzyl)pyridazin-3(2H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(4-(methylsulfonyl)benzyl)pyridin-2(1H)-one;

1-((1H-Benzo[d]imidazol-5-yl)methyl)-5-(3,5-d methylisoxazol-4-0)pyridin-2(1H)-one;

1-(3-Chloro-4-fluorobenzyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-(OH-Indazol-5-yl)methyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-((1H-Indol-4-yl)methyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-((4-Chlorophenyl)sulfonyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

5-(3-Amino-5-methylisoxazol-4-yl)-1-benzylpyridin-2(1H)-one;

3-Amino-1-(4-chlorobenzyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one;

1-Benzyl-5-(3,5-dimethylisoxazol-4-yl)-3-(4-methylpiperazin-1-yl)pyridin-2(1H)-one;

1-Benzyl-5-(3,5-dimethylisoxazol-4-yl)-4-methoxypyridin-2(1H)-one;

1-(3,4-Dichlorobenzyl)-5-(3,5-dimethylisoxazol-4-yl)pyridin-2(1H)-one,

1-Benzyl-5-(3,5-dimethylisoxazol-4-yl)-3-((4-fluorophenyl)amino)pyridin-2(1H)-one;

1-Benzyl-5-(3,5-dimethylisoxazol-4-yl)-3-((3-fluorophenyl)amino)pyridin-2(1H)-one;

1-Benzyl-5-(3-(hydroxymethyl)-5-methylisoxazol-4-yl)pyridin-2(1H)-one;

1-(4-Chlorobenzyl)-5-(3-(hydroxymethyl)-5-methylisoxazol-4-yl)pyridin-2(1H)-one;

1-Benzyl-5-(3-methylisothiazol-4-yl)pyridin-2(1H)-one;

1-Benzyl-5-(3,5-dimethylisoxazol-4-yl)-3-(piperazin-1-yl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(2-methoxybenzyl)pyridin-2(1H)-one;

5-(3,5-Dimethylisoxazol-4-yl)-1-(pyrimidin-2-ylmethyl)pyridin-2(1H)-one;

2-Benzyl-4-(3,5-dimethylisoxazol-4-yl)isoquinolin-1(2H)-one,

2-Benzyl-4-(3,5-dimethylisoxazol-4-yl)-2H-phthalazin-1-one;

6-Benzyl-8-(3,5-dimethylisoxazol-4-yl)-1,6-naphthyridin-5(6H)-one;

7-Benzyl-5-(3,5-dimethylisoxazol-4-yl)-1,7-naphthyridin-8(7H)-one;

2-Benzyl-4-(3,5-dimethylisoxazol-4-yl)-2,7-naphthyridin-1(2H)-one;

2-Benzyl-4-(3,5-dimethylisoxazol-4-yl)-2,6-naphthyridin-1(2H)-one; and

stereoisomers, tautomers, pharmaceutical acceptable salts, or hydrates thereof.

11. A pharmaceutical composition comprising a compound according to claim 1 .

12. A compound according to any one of claims 1 and 2 - 9 wherein W 1 is N.

13. A compound according to any one of claims 1 and 2 - 9 wherein W 1 is CR 5 .

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 23, 2016
From: ZENITH CAPITAL CORP.
To: ZENITH EPIGENETICS LTD.
Reel/Frame 041182/0891 →
CHANGE OF NAME Recorded Dec 21, 2016
From: ZENITH EPIGENETICS CORP.
To: ZENITH CAPITAL CORP.
Reel/Frame 041120/0548 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 3, 2015
From: LIU, SHUANG; DUFFY, BRYAN CORDELL; JIANG, MAY XIAOWU; WANG, RUIFANG; QUINN, JOHN FREDERICK; MARTIN, GREGORY SCOTT; ZHAO, HE; MOLINO, BRUCE FRANCIS; YOUNG, PETER RONALD
To: RESVERLOGIX CORP.
Reel/Frame 036947/0373 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 3, 2015
From: RESVERLOGIX CORP.
To: RVX THERAPEUTICS INC.
Reel/Frame 036947/0382 →
GENERAL CONVEYANCE AND ASSUMPTION AGREEMENT Recorded Jul 14, 2014
From: RVX THERAPEUTICS INC.
To: ZENITH EPIGENETICS CORP.
Reel/Frame 033312/0422 →
Continuity (2)
Provisional Application 61745274 · Dec 21, 2012
Related Publication 20140179648A1 · Jun 26, 2014