6-(benzo[d]thiazol-5-yl)-n-(3,4-dimethoxyphenyl)imidazo[1,2-a]pyrazin-8-amine

Abstract

Provided are imidazopyrazine compounds, particularly including 6-(benzo[d]thiazol-5-yl)-N-(3,4-dimethoxyphenyl)imidazo[1,2-a]pyrazin-8-amine, structure below, and methods and formulations for their use in inhibiting Spleen Tyrosine Kinase in treating conditions including B-cell lymphomas or leukemias and inflammatory conditions: ##STR00001##

Claims

1. A compound having the structure: ##STR00622## or a pharmaceutically acceptable salt thereof.

2. A pharmaceutical composition comprising the compound of claim 1, or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable vehicle chosen from carriers, adjuvants, and excipients.

Description

EXAMPLES

(1) The invention is further illustrated by the following non-limiting examples.

(2) In the examples below, the following abbreviations have the following meanings. If an abbreviation is not defined, it has its generally accepted meaning. DME=dimethyl ether DMEM=Dulbecco's modified Eagle's medium DMF=N,N-dimethylformamide DMSO=dimethylsulfoxide Et.sub.2O=diethylether g=gram h=hour mg=milligram min=minutes mL=milliliter mmol=millimoles mM=millimolar ng=nanogram nm=nanometer nM=nanomolar PBS=phosphate buffered saline μL=microliter μM=micromolar

Example I

Preparation of 6-(benzo[d]thiazol-5-yl)-N-(3,4-dimethoxy-phenyl)imidazo[1,2-a]pyrazin-8-amine(4)

(3) ##STR00017## ##STR00018##

(4) Preparation of 6,8-dibromoimidazo[1,2-a]pyrazine (1) A 1-L four-neck round bottom flask equipped with a temperature probe, mechanical stirrer and reflux condenser was charged with 2-bromo-1,1-diethoxyethane (68.1 g, 346 mmol) and 48% aqueous hydrogen bromide (11.3 mL, 99.2 mmol), and the reaction mixture was stirred at reflux for 2 h. The resulting mixture was allowed to cool to 40° C. and solid sodium bicarbonate (8.50 g, 101 mmol) was added in small portions until gas evolution was observed to cease. Caution: initial addition of sodium bicarbonate to the warm solution resulted in vigorous gas evolution (foaming). The resulting suspension was filtered into a 1-L four-neck round bottomed flask and the filter cake was washed with ethanol (200 mL). The flask was equipped with a temperature probe, mechanical stirrer and reflux condenser. 3,5-Dibromopyrazin-2-amine (50.0 g, 198 mmol) was added and the reaction mixture was heated at reflux, with vigorous stirring, for 16 h. After this time, the suspension was cooled to 0° C. and filtered. The filter cake was washed with cold ethanol (50 mL), dried under vacuum and added to a 1-L three-neck round bottomed flask equipped with a mechanical stirrer. Water (200 mL) was added and the vigorously stirred suspension was treated portion-wise with solid potassium carbonate (27.4 g, 198 mmol). Caution: gas evolution upon the addition of potassium carbonate observed. After stirring for 30 min, the resulting precipitate was isolated by filtration and the filter cake washed with water (100 mL) followed by ethanol (50 mL). The filter cake was dried at 50° C. to a constant weight, under vacuum to provide 6,8-dibromoimidazo[1,2-a]pyrazine (1) (52.0 g, 94%) as a light yellow solid: .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 9.02 (s, 1H), 8.23 (s, 1H), 7.90 (s, 1H).

(5) Preparation of 6-bromo-N-(3,4-dimethoxyphenyl)imidazo[1,2-a]pyrazin-8-amine (2) A mixture of 3,4-dimethoxyaniline (18.0 g, 118 mmol), 6,8-dibromoimidazo[1,2-a]pyrazine (25.0 g, 90.4 mmol), and N,N-diisopropylethylamine (11.7 g, 90.4 mmol) in DMF (500 mL) was stirred at 120° C. overnight. After this time, the reaction was cooled to room temperature and concentrated to approximately 100 mL under reduced pressure. The dark brown reaction mixture was poured into ice-cold water (300 mL) and stirred for 10 min. The resulting brown precipitate was filtered and the filter cake washed with water (100 mL). The filter cake was dried under vacuum and recrystallization from methanol (˜800 mL) to afford 6-bromo-N-(3,4,5-trimethoxyphenyl)imidazo[1,2-a]pyrazin-8-amine (2) (23.3 g, 74%) as a light brown needle-shaped solid: .sup.1H NMR (300 MHz, DMSO-d.sub.6) 9.81 (s, 1H), 8.22 (s, 1H), 7.93 (s, 1H), 7.75 (d, J=2.4 Hz, 1H), 7.62 (s, 1H), 7.53 (dd, J=8.7, 2.4, 1 H), 6.94 (d, J=8.7 Hz, 1H), 3.77 (s, 3H), 3.75 (s, 3H); ESI MS m/z 349.2 [M+H].sup.+; HPLC, 6.92 min, >99% (AUC).

(6) Preparation of 5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-yl)benzo[d]thiazole (3) A mixture of 5-bromobenzo[d]thiazole (428 mg, 2.00 mmol), bis(pinacolato)diboron (558 mg, 2.20 mmol) and potassium acetate (588 mg, 6.00 mmol) in dimethyl sulfoxide (7 mL) was sparged with nitrogen while stirring for 5 min. Dichloro 1,1-bis(diphenylphosphino)ferrocene palladium(II) dichloromethane (293 mg, 0.40 mmol) was then added and the reaction stirred at 85° C. for 3 h. After this time, the mixture was filtered through a pad of Celite and the filter cake was washed with ethyl acetate (75 mL) then water (20 mL). The filtrate was diluted with ethyl acetate (100 mL) and washed with water (2×75 mL), then brine (75 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by chromatography (silica, gradient 0% to 50% ethyl acetate in methylene chloride) to afford 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole (3) (200 mg, 38%) as a light brown solid: .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 9.41 (s, 1H), 8.32 (s, 1H), 8.18 (d, 1H, J=8.0 Hz), 7.72 (d, 1H, J=8.0 Hz), 1.33 (s, 12H); ESI MS m/z 262.1 [M+H]+.

(7) Preparation of 6-(benzo[d]thiazol-5-yl)-N-(3,4-dimethoxyphenyl)imidazo[1,2-a]pyrazin-8-amine (4) A mixture of 6-bromo-N-(3,4-dimethoxyphenyl)imidazo[1,2-a]pyrazin-8-amine (2) (209 mg, 0.601 mmol), and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole (3) (180 mg, 0.689 mmol) in 1 M aqueous sodium carbonate (0.76 mL) and 1,4-dioxane (2.4 mL) was sparged with nitrogen while stirring for 5 min. Tetrakis(triphenyl-phosphine) palladium(0) (69 mg, 0.06 mmol) was then added and the resulting mixture reacted under microwave irradiation at 135° C. for 30 min. After this time, the reaction was cooled to ambient temperature, diluted with 1:9 methanol/ethyl acetate (75 mL), and washed with water (50 mL) then brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by chromatography (silica, gradient 0% to 10% methanol in methylene chloride) to afford 6-(benzo[d]thiazol-5-yl)-N-(3,4-dimethoxyphenyl)imidazo[1,2-a]pyrazin-8-amine (4) (169 mg, 70%) as an off-white solid: mp 179-181° C.; .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ9.56 (s, 1H), 9.45 (s, 1H), 8.78 (s, 1H), 8.76 (d, 1H, J=1.2 Hz), 8.26 (d, 1H, J=8.7 Hz), 8.14 (m, 2H), 8.00 (s, 1H), 7.66 (s, 1H), 7.58 (dd, 1H, J=8.7, 2.4 Hz), 6.99 (d, 1H, J=8.7 Hz), 3.87 (s, 3H), 3.76 (s, 3H); MS m/z 404.6 [M+H].sup.+; HPLC, 6.475 min, 98.6% (AUC).

Example 2

(8) The following compounds were prepared using procedures similar to those described above. Those of ordinary skill in the art of organic synthesis will recognize when starting materials or reaction conditions should be varied to obtain the desired compound.

(9) MS data reported in this example was obtained as follows:

(10) MS conditions: Electrospray MS is performed on a MICROMASS LCT equipped with a LockSpray source for accurate mass measurements. Spectra are acquired in positive ion mode from 100-1000 Da at an acquisition rate of 1 spectrum/0.9 s with a 0.1 s interscan delay. The instrument is tuned for a resolution of 5000 (FWHM). Every 5.sup.th scan is taken from the reference position of the Lockspray source. Leucine enkephalin (556.2771 [M+H].sup.+) is used as the reference, or lock mass.

(11) TABLE-US-00001 Structure Name [M + H].sup.+ N-(3,4-dimethoxyphenyl)-6-(3- methylphenyl)imidazo[1,2- a]pyrazin-8-amine 361.2 0 N-(3,4-dimethoxyphenyl)-6-(3- nitrophenyl)imidazo[1,2-a]pyrazin- 8-amine 392.1 N-(3,4-dimethoxyphenyl)-6-{3- [(ethylamino)methyl]phenyl}imidazo [1,2-a]pyrazin-8-amine 404.7 N-(3,4-dimethoxyphenyl)-6-[3- (trifluoromethyl)phenyl]imidazo[1,2- a]pyrazin-8-amine 415.5 N-(3,4-dimethoxyphenyl)-6-(3- methoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 377.5 N-(3,4-dimethoxyphenyl)-6- (pyridin-4-yl)imidazo[1,2-a]pyrazin- 8-amine 348.3 N-(3,4-dimethoxyphenyl)-6- (pyridin-3-yl)imidazo[1,2-a]pyrazin- 8-amine 348.2 N-(3,4-dimethoxyphenyl)-6- phenylimidazo[1,2-a]pyrazin-8- amine 347 3-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}benzonitrile 372 N-(3,4-dimethoxyphenyl)-6-(4- fluorophenyl)imidazo[1,2- a]pyrazin-8-amine 365.2 4-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}benzene-1- sulfonamide 426.2 0 N-(3,4-dimethoxyphenyl)-6-{4- [(ethylamino)methyl]phenyl}imidazo [1,2-a]pyrazin-8-amine 404.7 6-(4-chlorophenyl)-N-(3,4- dimethoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 381.2 6-(3-chlorophenyl)-N-(4-ethoxy-3- methoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 395.2 N-(3,4-dimethoxyphenyl)-6-(4- methanesulfonylphenyl)imidazo[1, 2-a]pyrazin-8-amine 425.2 4-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}benzonitrile 372.1 N-(3,4-dimethoxyphenyl)-6-(4- methylphenyl)imidazo[1,2- a]pyrazin-8-amine 361.2 N-(4-ethoxy-3-methoxyphenyl)-6- (3-methylphenyl)imidazo[1,2- a]pyrazin-8-amine 375.2 N-(4-ethoxy-3-methoxyphenyl)-6- (3-fluorophenyl)imidazo[1,2- a]pyrazin-8-amine 379.1 6-(3,4-difluorophenyl)-N-(4-ethoxy- 3-methoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 397.1 6-(4-chloro-3-methylphenyl)-N-(4- ethoxy-3- methoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 409 0 3-{8-[(4-ethoxy-3- methoxyphenyl)amino]imidazo[1,2- a]pyrazin-6-yl}benzene-1- sulfonamide 440.1 N-(4-ethoxy-3-methoxyphenyl)-6- (3- methanesulfonylphenyl)imidazo[1, 2-a]pyrazin-8-amine 439.3 N-(4-ethoxy-3-methoxyphenyl)-6- (4-fluoro-3- methylphenyl)imidazo[1,2- a]pyrazin-8-amine 393.2 N-(4-ethoxy-3-methoxyphenyl)-6- (3-fluoro-3- methylphenyl)imidazo[1,2- a]pyrazin-8-amine 393.2 6-(3-chloro-4-methylphenyl)-N-(4- ethoxy-3- methoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 409.2 N-(4-ethoxy-3-methoxyphenyl)-6- (2-fluoropyridin-4-yl)imidazo[1,2- a]pyrazin-8-amine 380.3 N-(4-ethoxy-3-methoxyphenyl)-6- (5-methylpyridin-3-yl)imidazo[1,2- a]pyrazin-8-amine 376.5 6-(5-chloropyridin-3-yl)-N-(4- ethoxy-3- methoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 396.2 N-(4-ethoxy-3-methoxyphenyl)-6- (pyrimidin-5-yl)imidazo[1,2- a]pyrazin-8-amine 363.5 1-{4-[(4-{8-[(4-ethoxy-3- methoxyphenyl)amino]imidazo[1,2- a]pyrazin-6- yl}phenyl)methyl]piperazin-1- yl}ethan-1-one 487.5 0 1-{4-[(3-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6- yl}phenyl)methyl]piperazin-1- yl}ethan-1-one 487.1 N-(3,4-dimethoxyphenyl)-6-[3- (piperazin-1- ylmethyl)phenyl]imidazo[1,2- a]pyrazin-8-amine 445.3 N-(3,4-dimethoxyphenyl)-6-[4- (piperazin-1- ylmethyl)phenyl]imidazo[1,2- a]pyrazin-8-amine 445.3 6-(2,3-dihydro-1,4-benzodioxin-6- yl)-N-(3,4- dimethoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 404.42 N-(3-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}phenyl)acetamide 404.9 6-(3-aminophenyl)-N-(3,4- dimethoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 362.8 N-(4-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}phenyl)acetamide 404.6 N-(3,4-dimethoxyphenyl)-6- (thiophen-3-yl)imidazo[1,2- a]pyrazin-8-amine 353.5 N-(3,4-dimethoxyphenyl)-6-(1H- indazol-5-yl)imidazo[1,2-a]pyrazin- 8-amine 387.2 N-(3,4-dimethoxyphenyl)-6-[4-(1H- imidazol-2-yl)phenyl]imidazo[1,2- a]pyrazin-8-amine 413.3 0 N-(3,4-dimethoxyphenyl)-6- (quinolin-6-yl)imidazo[1,2- a]pyrazin-8-amine 398 N-(3,4-dimethoxyphenyl)-6-(1H- indazol-6-yl)imidazo[1,2-a]pyrazin- 8-amine 387.4 6-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}-3,4-dihydro-2H- 1,4-benzoxazin-3-one 418.6 6-(1,3-benzothiazol-5-yl)-N-(3,4- dimethoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 404.6 6-(1,3-benzothiazol-6-yl)-N-(3,4- dimethoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 404.9 6-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}quinazolin-2- amine 414.4 N-(3,4-dimethoxyphenyl)-6- (thiophen-2-yl)imidazo[1,2- a]pyrazin-8-amine 353.4 3-amino-5-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}-1-methyl-1,2- dihydropyridin-2-one 393.3 6-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}quinolin-2-amine 413.3 6-(4-aminophenyl)-N-(3,4- dimethoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 362.6 0 6-(1H-1,3-benzodiazol-5-yl)-N- (3,4-dimethoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 387.1 N-(3,4-dimethoxyphenyl)-6-[3-(1H- imidazol-5-yl)phenyl]imidazo[1,2- a]pyrazin-8-amine 413.3 7-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}-3,4-dihydro-2H- 1,4-benzoxazin-3-one 418.7 N-(4-ethoxy-3-methoxyphenyl)-6- (1H-indazol-5-yl)imidazo[1,2- a]pyrazin-8-amine 401.2 N-(3,4-dimethoxyphenyl)-6-[4-(1H- imidazol-5-yl)phenyl]imidazo[1,2- a]pyrazin-8-amine 413.4 N-(4-ethoxy-3-methoxyphenyl)-6- (1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-amine 401.1 6-(1,3-benzothiazol-6-yl)-N-(4- ethoxy-3- methoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 418.7 N-(3,4-dimethoxyphenyl)-6-[3-(1,3- thiazol-2-yl)phenyl]imidazo[1,2- a]pyrazin-8-amine 430.5 N-(3,4-dimethoxyphenyl)-6-(1- methyl-1H-1,3-benzodiazol-5- yl)imidazo[1,2-a]pyrazin-8-amine 401.3 5-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}-1,2- dihydropyridin-2-one 364.5 0 6-(1,3-benzothiazol-5-yl)-N-(4- ethoxy-3- methoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 418.7 N-(3,4-dimethoxyphenyl)-6-[4-(1,3- oxazol-2-yl)phenyl]imidazo[1,2- a]pyrazin-8-amine 414.1 (3-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)methanol 357 5-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}pyridin-2-amine 363.2 N-(3,4-dimethoxyphenyl)-6-[3-(1,3- oxazol-2-yl)phenyl]imidazo[1,2- a]pyrazin-8-amine 414.3 N-[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]-3,4-dihydro-2H-1,4- benzoxazin-6-amine 384 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)ethan-1-ol 371.1 N-(3,4-dimethoxyphenyl)-6-[4-(1,3- thiazol-2-yl)phenyl]imidazo[1,2- a]pyrazin-8-amine 430.5 (5-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- methoxyphenyl)methanol 387.2 N-(3,4-dimethoxyphenyl)-6-(1H- indol-6-yl)imidazo[1,2-a]pyrazin-8- amine 386.3 0 N-(3,4-dimethoxyphenyl)-6-(1- methyl-1H-1,3-benzodiazol-6- yl)imidazo[1,2-a]pyrazin-8-amine 401.2 N-(4-ethoxy-3-methoxyphenyl)-6- (1-methyl-1H-indazol-5- yl)imidazo[1,2-a]pyrazin-8-amine 415.6 N-(4-ethoxy-3-methoxyphenyl)-6- (1-methyl-1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8-amine 415.5 N-(3,4-dimethoxyphenyl)-6-(1- methyl-1H-indazol-5- yl)imidazo[1,2-a]pyrazin-8-amine 401.3 6-(1H-1,2,3-benzotriazol-6-yl)-N- (3,4-dimethoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 388.2 N-(3,4-dimethoxyphenyl)-6-{1H- imidazo[4,5-b]pyridin-6- yl}imidazo[1,2-a]pyrazin-8-amine 388.3 6-(1,3-benzoxazol-5-yl)-N-(3,4- dimethoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 388.7 6-(1,3-benzoxazol-6-yl)-N-(3,4- dimethoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 388.3 6-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}-4-methyl-3,4- dihydro-2H-1,4-benzoxazin-3-one 432.4 N-(3,4-dimethoxyphenyl)-6-(1- methyl-1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8-amine 400.3 00 N-(3,4-dimethoxyphenyl)-6-(1H- indol-5-yl)imidazo[1,2-a]pyrazin-8- amine 386.4 01 6-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}quinolin-3-amine 413.7 02 2-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)propan-2-ol 385.1 03 5-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}-1H-indazol-3- amine 402.1 04 6-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}-1H-1,3- benzodiazol-2-amine 402.3 05 6-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}-2H,3H,4H- pyrido[3,2-b][1,4]oxazin-3-one 419.5 06 6-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}-2-methyl-3,4- dihydro-2H-1,4-benzoxazin-3-one 432.5 07 6-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}-2,2-dimethyl-3,4- dihydro-2H-1,4-benzoxazin-3-one 446.4 08 7-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}quinolin-2-ol 414.3 09 2-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-2-methylpropan- 1-ol 399.3 0 6-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}-1H-indazol-3- amine 400.2 (4-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- methoxyphenyl)methanol 385.3 6-(2,3-dihydro-1H-indol-6-yl)-N- (3,4-dimethoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 388.8 N-[6-(3-amino-1H-indazol-5- yl)imidazo[1,2-a]pyrazin-8-yl]-3,4- dihydro-2H-1,4-benzoxazin-6- amine 399.2 N-{4-[3-(dimethylamino)propoxy]- 3-methoxyphenyl}-6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8-amine 458.7 3-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2- methoxyphenoxy)propan-1-ol 431.6 6-(1H-indazol-6-yl)-N-[4-methoxy- 3-(pyrrolidin-1- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 426.3 5-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2,3-dihydro- 1H-indol-2-one 382.3 7-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}quinoxalin-2-ol 413.5 7-{8-[(3,4- dimethoxyphenyl)amino]imidazo[1, 2-a]pyrazin-6-yl}-1H,2H,3H- pyrido[2,3-b][1,4]oxazin-2-one 419.5 0 N-[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]-4-methyl-3,4- dihydro-2H-1,4-benzoxazin-7- amine 398.3 N-(2-fluoro-4-methoxyphenyl)-6- (1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-amine 375.3 6-(1H-indazol-6-yl)-N-[3-methoxy- 4-(pyrrolidin-1- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 425.5 N-[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]-2,3,4,5-tetrahydro- 1,5-benzoxazepin-7-amine 398.5 1-(4-{[6-(3-amino-1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)ethan-1-ol 386.4 6-(3,4-dihydro-2H-1,4-benzoxazin- 6-yl)-N-(3,4- dimethoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 404.5 N-[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]-4-methyl-3,4- dihydro-2H-1,4-benzoxazin-6- amine 396.3 6-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2,3-dihydro- 1H-indol-2-one 382.3 N-(3,4-dimethoxyphenyl)-6-{1H- pyrrolo[3,2-b]pyridin-6- yl}imidazo[1,2-a]pyrazin-8-amine 387.6 N-[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]-3,4-dihydro-2H-1,4- benzoxazin-7-amine 384.3 0 6-{8-[(4-ethoxy-3- methoxyphenyl)amino]imidazo[1,2- a]pyrazin-6-yl}-1H-indazol-3-amine 416.8 N-[6-(2-aminoquinazolin-6- yl)imidazo[1,2-a]pyrazin-8-yl]-4- methyl-3,4-dihydro-2H-1,4- benzoxazin-6-amine 425.2 2-methyl-2-(4-{[6-(1-methyl-1H- 1,3-benzodiazol-5-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)propan-1-ol 413.7 6-(3,4-dihydro-2H-1,4-benzoxazin- 6-yl)-N-(4-ethoxy-3- methoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 418.4 N-[6-(2,3-dihydro-1H-indol-6- yl)imidazo[1,2-a]pyrazin-8-yl]-3,4- dihydro-2H-1,4-benzoxazin-6- amine 385.3 (2-methoxy-5-{[6-(1-methyl-1H-1,3- benzodiazol-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)methanol 401.2 6-(1H-indazol-6-yl)-N-{4-[2-methyl- 1-(morpholin-4-yl)propan-2- yl]phenyl}imidazo[1,2-a]pyrazin-8- amine 468.6 N-[6-(1H-indol-6-yl)imidazo[1,2- a]pyrazin-8-yl]-3,4-dihydro-2H-1,4- benzoxazin-6-amine 383.4 7-{8-[(4-methyl-3,4-dihydro-2H-1,4- benzoxazin-7- yl)amino]imidazo[1,2-a]pyrazin-6- yl}quinoxalin-2-ol 426.2 1-(4-{[6-(1,3-benzothiazol-5- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)ethan-1-ol 388.7 0 6-(1H-1,2,3-benzotriazol-6-yl)-N- [3-methoxy-4-(propan-2- yloxy)phenyl]imidazo[1,2- a]pyrazin-8-amine 416.6 5-(8-{[3-methoxy-4-(pyrrolidin-1- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazol-3-amine 441.4 2-(4-{[6-(2-aminoquinazolin-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)propan-2-ol 412.4 6-(1H-indazol-6-yl)-N-[3-methoxy- 4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 442.5 2-(4-{[6-(1,3-benzothiazol-5- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)propan-2-ol 402.3 6-(8-{[4-(2-hydroxypropan-2- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,4-dihydro-2H-1,4- benzoxazin-3-one 416.7 6-(1H-indazol-6-yl)-N-(3- methoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 357.3 6-(1H-indazol-6-yl)-N-(4- methoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 357.3 2-(4-{[6-(1-methyl-1H-1,3- benzodiazol-5-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)propan-2-ol 399.1 2-(4-{[6-(1-methyl-1H-1,3- benzodiazol-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)propan-2-ol 399.2 0 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2- methoxyphenyl)piperidin-4-ol 456.5 6-(1H-indazol-6-yl)-N-[4-(pyrrolidin- 1-yl)phenyl]imidazo[1,2-a]pyrazin- 8-amine 396.1 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)pyrrolidin-3-ol 412.3 2-(4-{[6-(4-methyl-3,4-dihydro-2H- 1,4-benzoxazin-7-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)propan-2-ol 416.5 2-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)propan-2-ol 402.5 2-(4-{[6-(1,4-dimethyl-1,2,3,4- tetrahydroquinoxalin-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)propan-2-ol 429.4 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2- methoxyphenyl)azetidin-3-ol 428.3 2-(4-{[6-(1H-indol-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)propan-2-ol 384.2 2-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-7-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)propan-2-ol 402.5 2-(4-{[6-(4-methyl-3,4-dihydro-2H- 1,4-benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)propan-2-ol 416.7 0 2-(4-{[6-(2,3-dimethyl-2H-indazol- 5-yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)propan-2-ol 413.4 2-(4-{[6-(3-methyl-1H-indazol-5- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)propan-2-ol 399.2 N-[3-methoxy-4-(morpholin-4- yl)phenyl]-6-(1-methyl-1H-1,3- benzodiazol-6-yl)imidazo[1,2- a]pyrazin-8-amine 456.3 6-(8-{[3-methoxy-4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)quinazolin-2-amine 469.4 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)azetidin-3-ol 398.3 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2- methoxyphenyl)pyrrolidin-3-ol 442.5 6-(3,4-dihydro-2H-1,4-benzoxazin- 6-yl)-N-[3-methoxy-4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 459.7 6-(1H-indazol-6-yl)-N-[4-(2- methoxypropan-2- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 399.4 N-(4-ethoxy-3-methoxyphenyl)-6- (1H-indol-6-yl)imidazo[1,2- a]pyrazin-8-amine 400.1 N-[3-methoxy-4-(morpholin-4- yl)phenyl]-6-(1-methyl-1H-1,3- benzodiazol-5-yl)imidazo[1,2- a]pyrazin-8-amine 456.4 0 N-[4-(4-ethylpiperazin-1-yl)-3- methoxyphenyl]-6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8-amine 469.7 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-3- methylpiperidin-3-ol 440.5 N-[4-(4-ethylpiperazin-1-yl)phenyl]- 6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-amine 439.4 6-(8-{[3-methoxy-4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazol-3-amine 457.6 5-(8-{[3-methoxy-4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazol-3-amine 457.5 6-(8-{[4-(2-hydroxypropan-2- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 399.45 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)piperidin-4-ol 426.2 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2-methoxyphenoxy)-2- methylpropan-2-ol 443.6 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2-methoxyphenyl)-4- methylpiperidin-4-ol 470.9 2-[(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2- methoxyphenyl)(methyl)amino] ethan-1-ol 430.5 0 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-4- methylpiperidin-4-ol 440.4 4-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenol 343.2 2-(4-{[6-(2,3-dihydro-1H-indol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)propan-2-ol 386.2 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-3- methylpyrrolidin-3-ol 426.2 N-[3-methoxy-4-(morpholin-4- yl)phenyl]-6-(2-methyl-1H-1,3- benzodiazol-5-yl)imidazo[1,2- a]pyrazin-8-amine 456.3 N-(4-ethoxy-3-methoxyphenyl)-6- (1-methyl-1H-1,3-benzodiazol-5- yl)imidazo[1,2-a]pyrazin-8-amine 415.6 (3R)-1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)pyrrolidin-3-ol 412.2 (3R)-1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2- methoxyphenyl)pyrrolidin-3-ol 442.7 (3S)-1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2- methoxyphenyl)pyrrolidin-3-ol 442.7 [4-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)morpholin-2- yl]methanol 442.7 0 N-(4-ethoxy-3-methoxyphenyl)-6- (1-methyl-1H-1,3-benzodiazol-6- yl)imidazo[1,2-a]pyrazin-8-amine 415.4 6-(5-fluoro-1H-indazol-6-yl)-N-[3- methoxy-4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 460.6 2-[1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)piperidin-4- yl]propan-2-ol 468.5 (3S)-1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)pyrrolidin-3-ol 412.1 N-[3-methoxy-4-(morpholin-4- yl)phenyl]-6-(3-methyl-1H-indazol- 6-yl)imidazo[1,2-a]pyrazin-8-amine 456.2 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2-methoxyphenyl)-3- methylpyrrolidin-3-ol 456.2 6-(1H-1,3-benzodiazol-6-yl)-N-(4- ethoxy-3- methoxyphenyl)imidazo[1,2- a]pyrazin-8-amine 401.2 6-(8-{[3-methoxy-4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 457.7 6-(8-{[3-methoxy-4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,3-dimethyl-2,3- dihydro-1H-indol-2-one 485.7 N-(4-ethoxy-3-methoxyphenyl)-6- {1H-pyrrolo[3,2-b]pyridin-6- yl}imidazo[1,2-a]pyrazin-8-amine 401.2 00 4-N-[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8-yl]-2- methoxy-1-N-(2-methoxyethyl)-1- N-methylbenzene-1,4-diamine 444.3 01 4-methyl-1-(4-{[6-(1-methyl-1H- 1,3-benzodiazol-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)piperidin-4-ol 454.1 02 6-(3,4-dihydro-2H-1,4-benzoxazin- 7-yl)-N-[3-methoxy-4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 459.4 03 6-(8-{[4-(1-hydroxy-2- methylpropan-2- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,4-dihydro-2H-1,4- benzoxazin-3-one 430.2 04 1-(4-{[6-(1H-1,3-benzodiazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-2-methylpropan- 2-ol 397.2 05 N-[3-methoxy-4-(morpholin-4- yl)phenyl]-6-{1H-pyrrolo[3,2- b]pyridin-6-yl}imidazo[1,2- a]pyrazin-8-amine 442.7 06 2-(4-{[6-(1H-1,3-benzodiazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-1,1,1,3,3,3- hexafluoropropan-2-ol 493.5 07 2-methyl-2-(4-{[6-(1-methyl-1H- 1,3-benzodiazol-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)propan-1-ol 413.4 08 2-methyl-2-{4-[(6-{1H-pyrrolo[3,2- b]pyridin-6-yl}imidazo[1,2- a]pyrazin-8- yl)amino]phenyl}propan-1-ol 399.2 09 2,2,2-trifluoro-1-(4-{[6-(1H-indazol- 6-yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)ethan-1-ol 425.3 0 2-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenyl)-2- methylpropan-1-ol 416.8 6-(8-{[4-(4-hydroxy-4- methylpiperidin-1- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,4-dihydro-2H-1,4- benzoxazin-3-one 471.7 4-methyl-1-{4-[(6-{1H-pyrrolo[3,2- b]pyridin-6-yl}imidazo[1,2- a]pyrazin-8- yl)amino]phenyl}piperidin-4-ol 440.5 1-(4-{[6-(1H-1,3-benzodiazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-4- methylpiperidin-4-ol 438.2 6-(1H-indazol-6-yl)-N-[4-(1- methoxy-2-methylpropan-2- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 413.3 4-methyl-1-(4-{[6-(1-methyl-1H- 1,3-benzodiazol-5-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)piperidin-4-ol 454.1 6-(1H-1,3-benzodiazol-6-yl)-N-[3- methoxy-4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 442.8 1,1,1-trifluoro-2-(4-{[6-(1H-indazol- 6-yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)propan-2-ol 437.4 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-2-methylpropan- 2-ol 399.3 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)cyclobutan-1-ol 397.2 0 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2-methoxyphenyl)-3- methylpiperidin-3-ol 470.9 4-N-[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8-yl]-1-N- (2-methoxyethyl)-1-N- methylbenzene-1,4-diamine 414.5 6-{8-[(4-ethoxy-3- methoxyphenyl)amino]imidazo[1,2- a]pyrazin-6-yl}-1H-indazole-3- carboxamide 444.8 2-[(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)(methyl)amino] ethan-1-ol 400.2 1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenyl)-4- methylpiperidin-4-ol 457.6 6-(1H-indazol-6-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 412.4 N-[4-(morpholin-4-yl)phenyl]-6- {1H-pyrrolo[3,2-b]pyridin-6- yl}imidazo[1,2-a]pyrazin-8-amine 412.5 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)piperidin-3-ol 426.2 6-(1H-indol-6-yl)-N-[4-(morpholin- 4-yl)phenyl]imidazo[1,2-a]pyrazin- 8-amine 411.2 2-(4-{[6-(1H-1,3-benzodiazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-2-methylpropan- 1-ol 399.1 0 6-(8-{[4-(1-hydroxy-2- methylpropan-2- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 414.5 2-(4-{[6-(1H-indol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenyl)-2- methylpropan-1-ol 398.2 6-{8-[(4-ethoxy-3- methoxyphenyl)amino]imidazo[1,2- a]pyrazin-6-yl}-2,3-dihydro-1H- indol-2-one 416.7 2-(4-{[6-(3-amino-1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-2-methylpropan- 1-ol 414.4 5-{8-[(4-ethoxy-3- methoxyphenyl)amino]imidazo[1,2- a]pyrazin-6-yl}-1H-indazol-3-amine 416.7 2-(4-{[6-(3-amino-1H-indazol-5- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-2-methylpropan- 1-ol 414.6 (3S)-1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2-methoxyphenyl)-3- methylpyrrolidin-3-ol 456.1 (3R)-1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2-methoxyphenyl)-3- methylpyrrolidin-3-ol 456.2 7-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1,2- dihydroquinoxalin-2-one 440.5 N,N-dimethyl-6-(8-{[4-(morpholin- 4-yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazole-3- carboxamide 483.4 0 5-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H-1,3- benzodiazol-2-one 428.3 1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenyl)-2- methylpropan-2-ol 416.8 N-methyl-2-(4-{[6-(2-oxo-2,3- dihydro-1H-indol-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenoxy)acetamide 429.4 N-[3-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6- yl)phenyl]methanesulfonamide 465.4 N-[4-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6- yl)phenyl]methanesulfonamide 465.4 [(2S)-4-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)morpholin-2- yl]methanol 442.3 [(2R)-4-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)morpholin-2- yl]methanol 442.3 6-(8-{[4-(2-hydroxy-2- methylpropyl)phenyl]amino}imidazo [1,2-a]pyrazin-6-yl)-3,4-dihydro- 2H-1,4-benzoxazin-3-one 430.4 1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-7-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- methoxyphenyl)-4-methylpiperidin- 4-ol 487.5 N-(2-hydroxyethyl)-N-methyl-6-(8- {[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indole-3- carboxamide 512.7 0 6′-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1′,2′- dihydrospiro[cyclopropane-1,3′- indole]-2′-one 453.1 3-methyl-1-(4-{[6-(1-methyl-1H- indazol-6-yl)imidazo[1,2-a]pyrazin- 8-yl]amino}phenyl)azetidin-3-ol 426.3 4-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- methoxyphenol 373.2 N-[3-methoxy-4-(morpholin-4- yl)phenyl]-6-(6-methoxypyridin-3- yl)imidazo[1,2-a]pyrazin-8-amine 433.5 6-(1H-1,2,3-benzotriazol-6-yl)-N- [4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 413.5 N,N-dimethyl-6-(8-{[4-(morpholin- 4-yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indole-3- carboxamide 482.4 N-[3-methoxy-4-(morpholin-4- yl)phenyl]-6-(5-methoxypyridin-3- yl)imidazo[1,2-a]pyrazin-8-amine 433.4 6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazol-3-amine 427.4 7-[8-({4-[(3S)-3-hydroxypyrrolidin- 1-yl]phenyl}amino)imidazo[1,2- a]pyrazin-6-yl]-1H,2H,3H- pyrido[2,3-b][1,4]oxazin-2-one 444.8 4-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-N-methyl-N- (oxan-4-yl)benzamide 468.2 0 6-(3-ethyl-1H-indazol-6-yl)-N-{4-[2- methyl-1-(morpholin-4-yl)propan-2- yl]phenyl}imidazo[1,2-a]pyrazin-8- amine 496.9 2,2-difluoro-6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,4-dihydro-2H-1,4- benzoxazin-3-one 479.1 1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-7-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- methoxyphenyl)-3-methylazetidin- 3-ol 459.3 6-(1H-indol-2-yl)-N-[4-(morpholin- 4-yl)phenyl]imidazo[1,2-a]pyrazin- 8-amine 411.3 (3S)-1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-7-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- methoxyphenyl)pyrrolidin-3-ol 459.6 1-(4-{[6-(4-fluoro-1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-3-methylazetidin- 3-ol 430.2 6-(1H-indazol-6-yl)-N-[4-(2H- 1,2,3,4-tetrazol-5- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 395.1 7-(8-{[4-(3-hydroxy-3- methylazetidin-1- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H,2H,3H- pyrido[2,3-b][1,4]oxazin-2-one 444.2 6-(1H-indazol-6-yl)-N-[3-methoxy- 4-(2- methoxyethoxy)phenyl]imidazo[1,2- a]pyrazin-8-amine 431.5 6-(2-ethyl-1,2,3,4- tetrahydroisoquinolin-6-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 455.4 0 4-{[6-(3,3-dimethyl-2-oxo-2,3- dihydro-1H-indol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-N- propylbenzamide 455.3 6-(8-{[3-ethoxy-4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,3-dimethyl-2,3- dihydro-1H-indol-2-one 499.7 6-(1H-indol-3-yl)-N-[4-(morpholin- 4-yl)phenyl]imidazo[1,2-a]pyrazin- 8-amine 411.2 6-(1,3-benzothiazol-5-yl)-N-{4-[2- methyl-1-(morpholin-4-yl)propan-2- yl]phenyl}imidazo[1,2-a]pyrazin-8- amine 485.7 (3E)-6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3-(1,3-thiazol-4- ylmethylidene)-2,3-dihydro-1H- indol-2-one 522.6 4-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-N-(oxan-4- yl)benzamide 454 6-(2-methyl-1,3-benzothiazol-5-yl)- N-{4-[2-methyl-1-(morpholin-4- yl)propan-2-yl]phenyl}imidazo[1,2- a]pyrazin-8-amine 499.5 6-(2,3-dihydro-1,4-benzodioxin-6- yl)-N-[3-methoxy-4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 460.6 6-(1H-indazol-6-yl)-N-[4-(2- methoxyethoxy)phenyl]imidazo[1,2- a]pyrazin-8-amine 401.1 6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)quinazolin-2-amine 439.7 0 6-(8-{[4-(4-hydroxy-4- methylpiperidin-1- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,3-dimethyl-2,3- dihydro-1H-indol-2-one 483.5 6-(1H-indazol-6-yl)-N-{4-[(2S)- oxolan-2- ylmethoxy]phenyl}imidazo[1,2- a]pyrazin-8-amine 427.1 6-(3-ethyl-1H-indazol-6-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 440.5 N-(2,3-dihydro-1,4-benzodioxin-6- yl)-6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-amine 385.3 N-(2H-1,3-benzodioxol-5-yl)-6-(1H- indazol-6-yl)imidazo[1,2-a]pyrazin- 8-amine 371.2 1-(2-ethoxy-4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-4- methylpiperidin-4-ol 484.7 6-[8-({4-[(3S)-3-hydroxypyrrolidin- 1-yl]phenyl}amino)imidazo[1,2- a]pyrazin-6-yl]-3,3-dimethyl-2,3- dihydro-1H-indol-2-one 455.2 6-(8-{[4-(3-hydroxy-3- methylazetidin-1- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,3-dimethyl-2,3- dihydro-1H-indol-2-one 455.3 6-(2H-1,3-benzodioxol-5-yl)-N-[3- methoxy-4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 446.3 6-(1H-indol-6-yl)-N-{4-[2-methyl-1- (morpholin-4-yl)propan-2- yl]phenyl}imidazo[1,2-a]pyrazin-8- amine 467.4 0 6-(1H-indazol-6-yl)-N-[4-(pyridin-4- yloxy)phenyl]imidazo[1,2- a]pyrazin-8-amine 420.3 (3E)-6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3-(pyridin-4- ylmethylidene)-2,3-dihydro-1H- indol-2-one 516.4 4-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-N-(oxetan-3- yl)benzamide 426.1 6-{3-[(diethylamino)methyl]-1H- indazol-6-yl}-N-[4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 497.3 1-[(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)carbonyl]-3- methylazetidin-3-ol 440.2 [6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazol-3- yl]methanol 442.3 N-[4-(morpholin-4-yl)phenyl]-6- (1H-pyrazol-4-yl)imidazo[1,2- a]pyrazin-8-amine 362.6 6-(4-fluoro-1H-indazol-6-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 430.3 N-[4-(morpholin-4-yl)phenyl]-6- {1H,2H,3H-pyrido[2,3- b][1,4]oxazin-6-yl}imidazo[1,2- a]pyrazin-8-amine 430.3 N-[4-(morpholin-4-yl)phenyl]-6- (1,3-thiazol-5-yl)imidazo[1,2- a]pyrazin-8-amine 379.2 00 {4-[(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)carbonyl] morpholin-2-yl}methanol 470.8 01 1-[(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)carbonyl]piperidin- 4-ol 454.1 02 N-ethyl-N-(2-hydroxyethyl)-4-{[6- (1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}benzamide 440.2 03 2-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- methoxyphenoxy)-N- methylacetamide 461.4 04 7-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1,2-dihydroquinolin- 2-one 439.5 05 6-(2-ethyl-1,2,3,4- tetrahydroisoquinolin-7-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 455.4 06 1-[(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)carbonyl]-4- methylpiperidin-4-ol 468.4 07 4-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- methoxybenzoic acid 401.1 08 6-(1H-indazol-6-yl)-N-{4-[(4- methylpiperazin-1- yl)carbonyl]phenyl}imidazo[1,2- a]pyrazin-8-amine 453.1 09 1-[(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)carbonyl]azetidin- 3-ol 426.3 0 3,3-dimethyl-6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 455.4 6-(1H-indazol-6-yl)-N-[4-(1- methylpiperidin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 424.2 2-(4-{[6-(4-fluoro-1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-2-methylpropan- 1-ol 417.7 2-[ethyl(4-{[6-(4-fluoro-1H-indazol- 6-yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)amino]ethan-1-ol 431.47 6-(1H-indazol-7-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 412.2 6-[8-({4-[ethyl(2- hydroxyethyl)amino]phenyl}amino) imidazo[1,2-a]pyrazin-6-yl]-3,3- dimethyl-2,3-dihydro-1H-indol-2- one 457.6 N-{4-[2- (dimethylamino)ethoxy]phenyl}-6- (1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-amine 414.6 6-(3,4-dihydro-2H-1,4-benzoxazin- 6-yl)-N-{4-[2- (dimethylamino)ethoxy]phenyl} imidazo[1,2-a]pyrazin-8-amine 431.4 1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenyl)-3- methylazetidin-3-ol 429.3 2-[6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2H-indazol-2- yl]ethan-1-ol 456.3 0 3-(2-ethoxy-4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenoxy)-2,2- dimethylpropan-1-ol 473.4 3-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenoxy)-2,2- dimethylpropan-1-ol 429.5 2-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2-methoxyphenoxy)-N- methylacetamide 444.8 2-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenoxy)-N- methylacetamide 431.4 2-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenoxy)-N- methylacetamide 414.4 2-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenoxy)acetic acid 401.1 N-(2-hydroxyethyl)-4-{[6-(1H- indazol-6-yl)imidazo[1,2-a]pyrazin- 8-yl]amino}-2-methoxybenzamide 442.1 6-(1,3-benzothiazol-5-yl)-N-[3- ethoxy-4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 473.2 6-(1H-indazol-6-yl)-N-{3-methoxy- 4-[(2R)-oxolan-2- ylmethoxy]phenyl}imidazo[1,2- a]pyrazin-8-amine 457.4 6-(1H-indazol-6-yl)-N-{4-[(2R)- oxolan-2- ylmethoxy]phenyl}imidazo[1,2- a]pyrazin-8-amine 427 0 6-(8-{[4-(3-hydroxy-3- methylazetidin-1- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,4-dihydro-2H-1,4- benzoxazin-3-one 443.2 6-(1H-indazol-6-yl)-N-[4- (morpholin-4- ylcarbonyl)phenyl]imidazo[1,2- a]pyrazin-8-amine 440.3 N-(2-hydroxyethyl)-4-{[6-(1H- indazol-6-yl)imidazo[1,2-a]pyrazin- 8-yl]amino}-N-methylbenzamide 428.2 2-[(2-ethoxy-4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)(methyl)amino] ethan-1-ol 444.6 N-[2-(dimethylamino)ethyl]-4-{[6- (1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-N- methylbenzamide 455.3 1-(2-fluoro-4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-3-methylazetidin- 3-ol 430.4 (3S)-1-(4-{[6-(4-fluoro-1H-indazol- 6-yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)pyrrolidin-3-ol 430.4 2-[6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazol-1- yl]ethan-1-ol 456.3 6-(8-{[4-(3-hydroxy-3- methylazetidin-1- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 427.2 N-[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]-2-methyl-1,2,3,4- tetrahydroisoquinolin-6-amine 396.1 0 N-[3-ethoxy-4-(morpholin-4- yl)phenyl]-6-(4-fluoro-1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8-amine 474.2 1-(2-ethoxy-4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenoxy)-2- methylpropan-2-ol 459.4 (3R)-3-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-1,4- dimethylpiperazin-2-one 453.4 N-(2-hydroxyethyl)-4-{[6-(1H- indazol-6-yl)imidazo[1,2-a]pyrazin- 8-yl]amino}benzamide 414.5 6-(8-{[3-ethoxy-4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 471.7 6-(3,4-dihydro-2H-1,4-benzoxazin- 6-yl)-N-[3-ethoxy-4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 473.2 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-N,N- dimethylpiperidin-4-amine 453.1 1-(4-{[6-(1,3-benzothiazol-5- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenoxy)-2- methylpropan-2-ol 432.4 (3R)-1-(2-ethoxy-4-{[6-(1H-indazol- 6-yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)pyrrolidin-3-ol 456.4 2-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenoxy)ethan-1-ol 387.3 0 1-(2-ethoxy-4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-3-methylazetidin- 3-ol 456.2 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2-methoxyphenyl)-3- methylazetidin-3-ol 442.2 4-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}benzoic acid 371 N-[3-ethoxy-4-(4-ethylpiperazin-1- yl)phenyl]-6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8-amine 483.3 4-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-N- propylbenzamide 412.1 1-(4-{[6-(4-fluoro-1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-4- methylpiperidin-4-ol 458.6 3-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2-methoxyphenoxy)-2,2- dimethylpropan-1-ol 459.5 6-(4-fluoro-1H-indazol-6-yl)-N-[4- (1,4-oxazepan-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 444.7 6-(8-{[3-ethoxy-4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,4-dihydro-2H-1,4- benzoxazin-3-one 487.5 1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenoxy)-2- methylpropan-2-ol 432.4 0 2-methyl-1-(4-{[6-(1-methyl-1H- 1,3-benzodiazol-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenoxy)propan-2-ol 429.3 6-(8-{[4-(2-hydroxy-2- methylpropoxy)phenyl]amino}imidazo [1,2-a]pyrazin-6-yl)-2,3-dihydro- 1H-indol-2-one 430.2 N-[3-fluoro-4-(morpholin-4- yl)phenyl]-6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8-amine 430.4 1-(4-{[6-(1,3-benzothiazol-5- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-3-methylazetidin- 3-ol 429.1 N-[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]-1,2,3,4- tetrahydroisoquinolin-6-amine 382.2 N-[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]-2,3-dihydro-1H- indol-6-amine 368.2 1-[6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1,2,3,4- tetrahydroisoquinolin-2-yl]ethan-1- one 469.6 1-[7-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1,2,3,4- tetrahydroisoquinolin-2-yl]ethan-1- one 469.7 N-[4-(morpholin-4-yl)phenyl]-6- {1H,2H,3H-pyrido[2,3- b][1,4]oxazin-7-yl}imidazo[1,2- a]pyrazin-8-amine 430.4 6-(1-methyl-1H-indazol-6-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 426.1 0 N-[4-(morpholin-4-yl)phenyl]-6- {2H,3H,4H-pyrido[3,2- b][1,4]oxazin-7-yl}imidazo[1,2- a]pyrazin-8-amine 430.4 6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H,2H,3H- pyrido[2,3-b][1,4]oxazin-2-one 444.2 (3S)-1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-7-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenyl)-3- methylpiperidin-3-ol 457.2 5-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 427 1-methyl-6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 441.4 6-(8-{[4-(2-hydroxy-2- methylpropoxy)phenyl]amino}imidazo [1,2-a]pyrazin-6-yl)-3,4-dihydro- 2H-1,4-benzoxazin-3-one 446.3 2-[4-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)piperazin-1- yl]ethan-1-ol 455.2 6-(1H-indazol-4-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 412.2 N-[3-ethoxy-4-(morpholin-4- yl)phenyl]-6-(1-methyl-1H-1,3- benzodiazol-6-yl)imidazo[1,2- a]pyrazin-8-amine 470.2 6-(1H-indazol-6-yl)-N-[4-(piperazin- 1-yl)phenyl]imidazo[1,2-a]pyrazin- 8-amine 411.2 0 N-[4-(morpholin-4-yl)phenyl]-6- (1,2,3,4-tetrahydroisoquinolin-7- yl)imidazo[1,2-a]pyrazin-8-amine 427.1 N-[4-(morpholin-4-yl)phenyl]-6- (1,2,3,4-tetrahydroisoquinolin-6- yl)imidazo[1,2-a]pyrazin-8-amine 427 7-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H,2H,3H- pyrido[2,3-b][1,4]oxazin-2-one 444.8 6-{1-methyl-1H-pyrrolo[3,2- b]pyridin-6-yl}-N-[4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 426.2 6-(1-methyl-1H-indol-6-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 425.3 6-(1,3-benzoxazol-5-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 413.5 6-(4-methyl-3,4-dihydro-2H-1,4- benzoxazin-7-yl)-N-[4-(morpholin- 4-yl)phenyl]imidazo[1,2-a]pyrazin- 8-amine 443.6 6-(4-methyl-3,4-dihydro-2H-1,4- benzoxazin-6-yl)-N-[4-(morpholin- 4-yl)phenyl]imidazo[1,2-a]pyrazin- 8-amine 443.9 6-[8-({4-[(3S)-3-hydroxypyrrolidin- 1-yl]phenyl}amino)imidazo[1,2- a]pyrazin-6-yl]-3,4-dihydro-2H-1,4- benzoxazin-3-one 443.7 (3R)-1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-7-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenyl)-3- methylpiperidin-3-ol 457.2 0 6-[8-({4-[(3S)-3-hydroxy-3- methylpiperidin-1- yl]phenyl}amino)imidazo[1,2- a]pyrazin-6-yl]-3,4-dihydro-2H-1,4- benzoxazin-3-one 471.7 6-[8-({4-[(3R)-3-hydroxy-3- methylpiperidin-1- yl]phenyl}amino)imidazo[1,2- a]pyrazin-6-yl]-3,4-dihydro-2H-1,4- benzoxazin-3-one 471.6 6-[8-({4-[(3S)-3-hydroxy-3- methylpiperidin-1- yl]phenyl}amino)imidazo[1,2- a]pyrazin-6-yl]-2,3-dihydro-1H- indol-2-one 455.4 6-[8-({4-[(3R)-3-hydroxy-3- methylpiperidin-1- yl]phenyl}amino)imidazo[1,2- a]pyrazin-6-yl]-2,3-dihydro-1H- indol-2-one 455.2 (3R)-1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenyl)-3- methylpiperidin-3-ol 457.2 (3S)-3-methyl-1-(4-{[6-(1-methyl- 1H-1,3-benzodiazol-5- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)piperidin-3-ol 454.6 (3R)-3-methyl-1-(4-{[6-(1-methyl- 1H-1,3-benzodiazol-5- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)piperidin-3-ol 454.2 (3R)-3-methyl-1-(4-{[6-(1-methyl- 1H-1,3-benzodiazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)piperidin-3-ol 454.1 6-(8-{[4-(4-ethylpiperazin-1- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,4-dihydro-2H-1,4- benzoxazin-3-one 470.8 6-(1,3-benzothiazol-6-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 429.3 00 6-(1,3-benzothiazol-5-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 429.4 01 6-(1,3-benzoxazol-6-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 413.5 02 6-(1H-indazol-5-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 412.3 03 (3S)-1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenyl)-3- methylpiperidin-3-ol 457.6 04 (3S)-3-methyl-1-(4-{[6-(1-methyl- 1H-1,3-benzodiazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)piperidin-3-ol 450.4 05 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-3-methylazetidin- 3-ol 412.3 06 N-{4-[(4-ethylpiperazin-1- yl)methyl]phenyl}-6-(1-methyl-1H- 1,3-benzodiazol-6-yl)imidazo[1,2- a]pyrazin-8-amine 467.5 07 2-[ethyl(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)amino]ethan-1-ol 414.4 08 1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-7-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)azetidin-3-ol 415.2 09 7-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2H,3H,4H- pyrido[3,2-b][1,4]oxazin-3-one 444.8 0 6-(1-methyl-1H-indazol-5-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 426.1 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenoxy)-2- methylpropan-2-ol 415.4 6-(3,4-dihydro-2H-1,4-benzoxazin- 6-yl)-N-[4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 429.3 4-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)piperazin-2-one 425.1 6-(1-methyl-1H-1,3-benzodiazol-6- yl)-N-[4-(morpholin-4- ylmethyl)phenyl]imidazo[1,2- a]pyrazin-8-amine 440.4 6-(1H-1,3-benzodiazol-6-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 412.2 1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)azetidin-3-ol 415.4 6-(1H-indazol-6-yl)-N-[4-(1,4- oxazepan-4-yl)phenyl]imidazo[1,2- a]pyrazin-8-amine 426.1 (3S)-1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-3- methylpiperidin-3-ol 440.3 (3R)-1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-3- methylpiperidin-3-ol 440.3 0 (3S)-1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-3- methylpyrrolidin-3-ol 426.1 (3R)-1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-3- methylpyrrolidin-3-ol 426.2 6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,4-dihydro-2H-1,4- benzoxazin-3-one 443.7 6-(8-{[4-(3-hydroxyazetidin-1- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 413.4 6-(8-{[4-(3-hydroxy-3- methylpyrrolidin-1- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,4-dihydro-2H-1,4- benzoxazin-3-one 457.6 6-(1-methyl-1H-1,3-benzodiazol-6- yl)-N-[4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 426.2 6-(3,4-dihydro-2H-1,4-benzoxazin- 7-yl)-N-[4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 429.2 1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-7-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenyl)-4- methylpiperidin-4-ol 457.2 1-(4-{[6-(1H-indol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenyl)-4- methylpiperidin-4-ol 439.7 1-(4-{[6-(1H-indol-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)azetidin-3-ol 397.1 0 1-(4-{[6-(1-methyl-1H-1,3- benzodiazol-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)azetidin-3-ol 412.3 1-(4-{[6-(1-methyl-1H-1,3- benzodiazol-5-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)azetidin-3-ol 412.2 6-(1-methyl-1H-1,3-benzodiazol-5- yl)-N-[4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 426.1 6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 427.1 6-(8-{[4-(3-hydroxyazetidin-1- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,4-dihydro-2H-1,4- benzoxazin-3-one 429.3 5-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1,3- benzoxazol-2-one 429.3 4-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-N,N- dimethylbenzene-1-sulfonamide 434.3 6-(1H-indazol-6-yl)-N-{4-[4- (propan-2-yl)piperazin-1- yl]phenyl}imidazo[1,2-a]pyrazin-8- amine 453.9 2-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-7-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenyl)-2- methylpropan-1-ol 416.8 4-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)thiomorpholine- 1,1-dione 460.4 0 6-(1H-indazol-6-yl)-N-[4-(2- methylmorpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 426.1 N-(4-ethoxy-3-methoxyphenyl)-6- (1H-indazol-6-yl)-5- methylimidazo[1,2-a]pyrazin-8- amine 415.3 1-(4-{[6-(1H-indazol-6-yl)-5- methylimidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-4- methylpiperidin-4-ol 454.2 N,6-bis[4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 457.3 2-[1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)piperidin-4- yl]ethan-1-ol 454.1 6-[3-(morpholin-4-yl)phenyl]-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 457.6 2-[6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indol-3-yl]ethan- 1-ol 455.2 [1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)piperidin-4- yl]methanol 440.4 1-[4-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)piperazin-1- yl]ethan-1-one 453 6-(5-chloro-8-{[3-methoxy-4- (morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 491.3 0 5-chloro-N-[3-methoxy-4- (morpholin-4-yl)phenyl]-6-{1H- pyrrolo[3,2-b]pyridin-6- yl}imidazo[1,2-a]pyrazin-8-amine 476.4 N-methyl-5-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)pyridin-3-amine 402.3 6-(1H-indazol-6-yl)-N-(4-{7-oxa-2- azaspiro[3.5]nonan-2- yl}phenyl)imidazo[1,2-a]pyrazin-8- amine 452.3 6-(2-methyl-1H-1,3-benzodiazol-6- yl)-N-[4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 426.2 5-(8-{[4-(3-hydroxy-3- methylazetidin-1- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1-methyl-2,3- dihydro-1H-1,3-benzodiazol-2-one 442.7 N-{4-[(2R,6S)-2,6- dimethylmorpholin-4-yl]phenyl}-6- (1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-amine 440.3 N-[6-(1H-indazol-6-yl)-5- methylimidazo[1,2-a]pyridin-8-yl]- 5-(morpholin-4-yl)pyridin-2-amine 426.2 [(2R)-6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,4-dihydro-2H-1,4- benzoxazin-2-yl]methanol 459.3 6-(1H-indazol-6-yl)-N-[3- (methoxymethyl)-4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 456.3 7-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1,2,3,4- tetrahydroquinoxalin-2-one 442.4 0 5-chloro-6-(1H-indazol-6-yl)-N-[3- methoxy-4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 476.1 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-3-methylazetidin- 3-amine 411.3 [(2S)-6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,4-dihydro-2H-1,4- benzoxazin-2-yl]methanol 459.3 7-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1,2,3,4- tetrahydroquinolin-2-one 441.5 5-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- (morpholin-4-yl)benzonitrile 437.1 6-(3,4-dihydro-2H-1,4-benzoxazin- 6-yl)-3-methyl-N-[4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 443.9 N-[3-methoxy-4-(morpholin-4- yl)phenyl]-3-methyl-6-{1H- pyrrolo[3,2-b]pyridin-6- yl}imidazo[1,2-a]pyrazin-8-amine 456.4 5-methyl-6-(2-methyl-1H-1,3- benzodiazol-6-yl)-N-[4-(morpholin- 4-yl)phenyl]imidazo[1,2-a]pyrazin- 8-amine 440.2 5-ethyl-6-(1H-indazol-6-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 440.4 1-methyl-6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H-1,3- benzodiazol-2-one 442.7 0 6-(3-methyl-8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 441.3 1,3-dimethyl-5-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H-1,3- benzodiazol-2-one 456.2 2-[6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazol-3- yl]propan-2-ol 470.8 6-(4-fluoro-1H-indol-6-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 429.3 5-{[6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- (morpholin-4-yl)benzamide 455.2 5-(8-{[3-methoxy-4-(morpholin-4- yl)phenyl]amino}-5- methylimidazo[1,2-a]pyrazin-6-yl)- 2,3-dihydro-1H-1,3-benzodiazol-2- one 472.4 5-(5-methyl-8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H-1,3- benzodiazol-2-one 442.4 [2-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)phenyl]methanol 402.2 1-methyl-5-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H-1,3- benzodiazol-2-one 442.7 2-[6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,4-dihydro-2H-1,4- benzoxazin-4-yl]ethan-1-ol 473.2 0 (3R)-2,2-dimethyl-6-(8-{[4- (morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-3-ol 457.6 6-(1H-indazol-6-yl)-N-{3-methoxy- 4-[4-(2-methoxyethyl)piperazin-1- yl]phenyl}imidazo[1,2-a]pyrazin-8- amine 499.6 2-(4-{2-methoxy-4-[(6-{1H- pyrrolo[3,2-b]pyridin-6- yl}imidazo[1,2-a]pyrazin-8- yl)amino]phenyl}piperazin-1- yl)ethan-1-ol 485.7 1-[6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazol-3- yl]ethan-1-ol 456.5 2-[6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazol-3- yl]ethan-1-ol 456.5 2-{[5-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)pyridin-3- yl]amino}ethan-1-ol 432.6 N-[3-methoxy-4-(morpholin-4- yl)phenyl]-5-methyl-6-{1H- pyrrolo[3,2-b]pyridin-6- yl}imidazo[1,2-a]pyrazin-8-amine 456.2 (3S)-2,2-dimethyl-6-(8-{[4- (morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-3-ol 457.8 N-{4-[4-(3-fluoropropyl)piperazin-1- yl]phenyl}-6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8-amine 471.4 6-(1H-indazol-6-yl)-N-[4-(oxan-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 411.3 0 N-[4-(4-fluoropiperidin-1-yl)phenyl]- 6-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-amine 428.2 6-(1H-indazol-6-yl)-N-[3-(2- methoxyethoxy)-4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 486.6 6-(1H-indazol-6-yl)-N-[4-(4H-1,2,4- triazol-4-yl)phenyl]imidazo[1,2- a]pyrazin-8-amine 394.3 N-[4-(3,3-difluoropyrrolidin-1- yl)phenyl]-6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8-amine 432.3 6-(1H-indazol-6-yl)-N-[3-methoxy- 4-(morpholin-4-yl)phenyl]-5- methylimidazo[1,2-a]pyrazin-8- amine 456.3 2,2-dimethyl-6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-3-one 455.3 6-(1H-indazol-6-yl)-N-[3-methoxy-4- (methoxymethyl)phenyl]imidazo[1, 2-a]pyrazin-8-amine 401.2 1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2-methoxyphenyl)-2- methylpropan-2-ol 429.4 [(2S)-4-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)morpholin-2- yl]methanol 459.3 N-[4-(4,4-difluoropiperidin-1- yl)phenyl]-6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8-amine 446.3 00 6-(1H-indazol-6-yl)-N-{3-methoxy- 4-[(2- methoxyethoxy)methyl]phenyl} imidazo[1,2-a]pyrazin-8-amine 445.5 01 2-[2-(morpholin-4-yl)-5-[(6-{1H- pyrrolo[3,2-b]pyridin-6- yl}imidazo[1,2-a]pyrazin-8- yl)amino]phenoxy]ethan-1-ol 472.4 02 6-(1H-indazol-6-yl)-N-[4-(3- methoxy-3-methylazetidin-1- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 426.2 03 5-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)pyridin-3-amine 388.8 04 N-[4-(morpholin-4-yl)phenyl]-6- (1,5-naphthyridin-3-yl)imidazo[1,2- a]pyrazin-8-amine 424.2 05 3-ethyl-1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)azetidin-3-ol 426 06 N-[4-(3-fluoro-3-methylazetidin-1- yl)phenyl]-6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8-amine 414.5 07 N-[4-(3,3-difluoropiperidin-1- yl)phenyl]-6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8-amine 446.2 08 [(2R)-4-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)morpholin-2- yl]methanol 459.4 09 N-[4-(3,3-difluoroazetidin-1- yl)phenyl]-6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8-amine 418.6 0 (3S)-1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- methoxyphenyl)pyrrolidin-3-ol 459.5 (3R)-1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- methoxyphenyl)pyrrolidin-3-ol 459.5 N-[4-(3-fluoroazetidin-1-yl)phenyl]- 5-(1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-amine 400.2 6-(3,4-dihydro-2H-1,4-benzoxazin- 6-yl)-N-[3-methoxy-4-(morpholin-4- yl)phenyl]-5-methylimidazo[1,2- a]pyrazin-8-amine 473.2 N,N-diethyl-6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazol-3-amine 483.6 (3S)-3-hydroxy-3-methyl-6-(8-{[4- (morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 457.6 N-[4-(morpholin-4-yl)phenyl]-6- (quinoxalin-6-yl)imidazo[1,2- a]pyrazin-8-amine 424.3 (3R)-3-hydroxy-3-methyl-6-(8-{[4- (morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 457.6 6-(1H-indazol-6-yl)-N-{3-methoxy- 4-[(2S)-oxolan-2- ylmethoxy]phenyl}imidazo[1,2- a]pyrazin-8-amine 457.5 6-(8-{[3-methoxy-4-(morpholin-4- yl)phenyl]amino}-5- methylimidazo[1,2-a]pyrazin-6-yl)- 2,3-dihydro-1H-indol-2-one 471.7 0 6-(8-{[3-methoxy-4-(morpholin-4- yl)phenyl]amino}-5- methylimidazo[1,2-a]pyrazin-6-yl)- 3,4-dihydro-2H-1,4-benzoxazin-3- one 487.5 (3S)-1-{4-[(6-{1H,2H,3H- pyrido[2,3-b][1,4]oxazin-7- yl}imidazo[1,2-a]pyrazin-8- yl)amino]phenyl}pyrrolidin-3-ol 430.4 (3R)-1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)pyrrolidin-3-ol 429.4 6-[8-({4-[(3R)-3-hydroxypyrrolidin- 1-yl]-3- methoxyphenyl}amino)imidazo[1,2- a]pyrazin-6-yl]-2,3-dihydro-1H- indol-2-one 457.3 N-[4-(1H-imidazol-1-yl)phenyl]-6- (1H-indazol-6-yl)imidazo[1,2- a]pyrazin-8-amine 393.3 6-(1H-indazol-6-yl)-N-[4-(1H- pyrazol-1-yl)phenyl]imidazo[1,2- a]pyrazin-8-amine 393.2 6-[8-({4-[(3R)-3-hydroxypyrrolidin- 1-yl]phenyl}amino)imidazo[1,2- a]pyrazin-6-yl]-2,3-dihydro-1H- indol-2-one 427.1 6-[8-({4-[(3S)-3-hydroxypyrrolidin- 1-yl]phenyl}amino)imidazo[1,2- a]pyrazin-6-yl]-2,3-dihydro-1H- indol-2-one 427 1-(4-{[6-(1H-indazol-6-yl)-5- methylimidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-3-methylazetidin- 3-ol 426.2 (3S)-1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)piperidin-3-ol 426.2 0 (3R)-1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)piperidin-3-ol 426.2 2-[3-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)phenyl]propan-2-ol 430.2 6-(5-methyl-8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,4-dihydro-2H-1,4- benzoxazin-3-one 457.2 N-ethyl-6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazol-3-amine 455.2 2-[4-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2- methoxyphenyl)piperazin-1- yl]ethan-1-ol 485.6 6-[8-({4-[(3S)-3-hydroxypyrrolidin- 1-yl]-3- methoxyphenyl}amino)imidazo[1,2- a]pyrazin-6-yl]-2,3-dihydro-1H- indol-2-one 457.6 2-(5-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2-(morpholin-4- yl)phenoxy)ethan-1-ol 472.4 (3S)-1-(4-{[6-(1-methyl-1H-indazol- 6-yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)pyrrolidin-3-ol 426.2 6-(5-methyl-8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 441.3 2-methyl-1-[6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2H-indazol-2- yl]propan-2-ol 484.6 0 2-methyl-1-{4-[(6-{1H-pyrrolo[3,2- b]pyridin-6-yl}imidazo[1,2- a]pyrazin-8- yl)amino]phenyl}propan-2-ol 399.2 (3S)-1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)pyrrolidin-3-ol 429.4 2-[4-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)phenyl]propan-2-ol 430.2 6-(1H-indazol-6-yl)-3-methyl-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 426.2 N-(2-hydroxyethyl)-N-methyl-6-(8- {[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazole-3- carboxamide 513.6 5-chloro-6-(1H-indazol-6-yl)-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 446.4 N-(2-hydroxyethyl)-2-(4-{[6-(1H- indazol-6-yl)imidazo[1,2-a]pyrazin- 8-yl]amino}phenoxy)acetamide 444.8 1-(4-{[6-(1H-indol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- methoxyphenyl)-3-methylazetidin- 3-ol 441.4 1-(4-{[6-(1H-indol-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}phenyl)-3- methylazetidin-3-ol 411.4 2-methyl-1-[6-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazol-1- yl]propan-2-ol 484.7 0 6-(1H-indazol-6-yl)-N-[3-methoxy- 4-(oxan-4- yloxy)phenyl]imidazo[1,2- a]pyrazin-8-amine 457.6 N-[3-methoxy-4-(morpholin-4- yl)phenyl]-6-(1-methyl-1H-indazol- 6-yl)imidazo[1,2-a]pyrazin-8-amine 456.2 6-(3,4-dihydro-2H-1,4-benzoxazin- 6-yl)-5-methyl-N-[4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 443.3 2-methyl-2-(4-{[6-(1-methyl-1H- indazol-6-yl)imidazo[1,2-a]pyrazin- 8-yl]amino}phenyl)propan-1-ol 413.5 1-(3-hydroxy-3-methylazetidin-1- yl)-2-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenoxy)ethan-1-one 470.7 1-[6-(1,3-benzothiazol-5- yl)imidazo[1,2-a]pyridin-8-yl]-3- methylurea 324.2 1-[6-(1,3-benzothiazol-5- yl)imidazo[1,2-a]pyridin-8-yl]-3- ethylurea 338.3 1-{2-ethoxy-4-[(6-{1H-pyrrolo[3,2- b]pyridin-6-yl}imidazo[1,2- a]pyrazin-8-yl)amino]phenyl}-3- methylazetidin-3-ol 456.4 1-{2-methoxy-4-[(6-{1H- pyrrolo[3,2-b]pyridin-6- yl}imidazo[1,2-a]pyrazin-8- yl)amino]phenyl}-3-methylazetidin- 3-ol 442.4 6-(1H-indol-6-yl)-N-[3-methoxy-4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 441.5 0 6-(1H-indazol-6-yl)-N-[4-(oxan-4- yloxy)phenyl]imidazo[1,2- a]pyrazin-8-amine 427 6-(8-{[3-methoxy-4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-3,4-dihydro-2H-1,4- benzoxazin-3-one 473.2 6-(1H-indazol-6-yl)-N-[3- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 412.5 2-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenoxy)-N,N- dimethylacetamide 428.3 3-methyl-1-{4-[(6-{1H-pyrrolo[3,2- b]pyridin-6-yl}imidazo[1,2- a]pyrazin-8- yl)amino]phenyl}azetidin-3-ol 412.3 1-methyl-5-(5-methyl-8-{[4- (morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H-1,3- benzodiazol-2-one 456.5 1-ethyl-5-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H-1,3- benzodiazol-2-one 456.5 6-(3,4-dihydro-2H-1,4-benzoxazin- 6-yl)-5-ethyl-N-[4-(morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 457.6 6-(5-ethyl-8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 455.1 (3S)-1-{4-[(6-{1H-pyrrolo[3,2- b]pyridin-6-yl}imidazo[1,2- a]pyrazin-8- yl)amino]phenyl}piperidin-3-ol 426.2 0 (3S)-1-{2-methoxy-4-[(6-{1H- pyrrolo[3,2-b]pyridin-6- yl}imidazo[1,2-a]pyrazin-8- yl)amino]phenyl}piperidin-3-ol 456.2 2-(1-{4-[(6-{1H-pyrrolo[3,2- b]pyridin-6-yl}imidazo[1,2- a]pyrazin-8- yl)amino]phenyl}piperidin-4- yl)ethan-1-ol 454.2 2-[6-(5-methyl-8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazol-3- yl]ethan-1-ol 470.6 1-[4-({6-[3-(2-hydroxyethyl)-1H- indazol-6-yl]imidazo[1,2-a]pyrazin- 8-yl}amino)phenyl]-3- methylazetidin-3-ol 456.4 6-[8-({4-[(2R)-2- (hydroxymethyl)morpholin-4- yl]phenyl}amino)imidazo[1,2- a]pyrazin-6-yl]-2,3-dihydro-1H- indol-2-one 457.5 6-[8-({4-[(2S)-2- (hydroxymethyl)morpholin-4- yl]phenyl}amino)imidazo[1,2- a]pyrazin-6-yl]-2,3-dihydro-1H- indol-2-one 457.6 5-(5-ethyl-8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1-methyl-2,3- dihydro-1H-1,3-benzodiazol-2-one 470.7 5-ethyl-N-[4-(morpholin-4- yl)phenyl]-6-{1H-pyrrolo[3,2- b]pyridin-6-yl}imidazo[1,2- a]pyrazin-8-amine 440.4 (3R)-1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- methoxyphenyl)piperidin-3-ol 473.3 N-[4-(morpholin-4-yl)phenyl]-6- (1,2,3,5-tetrahydro-4,1- benzoxazepin-8-yl)imidazo[1,2- a]pyrazin-8-amine 443.4 0 [(3R)-4-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)morpholin-3- yl]methanol 442.3 [(3S)-4-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)morpholin-3- yl]methanol 442.2 (3S)-1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- methoxyphenyl)piperidin-3-ol 473.2 (1-{4-[(6-{1H-pyrrolo[3,2-b]pyridin- 6-yl}imidazo[1,2-a]pyrazin-8- yl)amino]phenyl}piperidin-4- yl)methanol 440.3 [(2R)-4-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- methoxyphenyl)morpholin-2- yl]methanol 489.4 [(2S)-4-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8-yl]amino}-2- methoxyphenyl)morpholin-2- yl]methanol 489.4 4-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenoxy)cyclohexan-1-ol 441.5 6-(1H-indazol-6-yl)-N-(4-{2-oxa-6- azaspiro[3.3]heptan-6- yl}phenyl)imidazo[1,2-a]pyrazin-8- amine 424.2 2-[6-(8-{[3-methoxy-4-(morpholin- 4-yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indazol-3- yl]ethan-1-ol 486.6 [(2S)-4-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2- methoxyphenyl)morpholin-2- yl]methanol 472.4 0 [(2R)-4-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}-2- methoxyphenyl)morpholin-2- yl]methanol 472.4 2-[1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)piperidin-4- yl]ethan-1-ol 471.8 6-(1H-indazol-6-yl)-N-(4-{8-oxa-3- azabicyclo[3.2.1]octan-3- yl}phenyl)imidazo[1,2-a]pyrazin-8- amine 438.3 [(3R)-1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)pyrrolidin-3- yl]methanol 426.2 [(3S)-1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)pyrrolidin-3- yl]methanol 426.2 5-chloro-6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)-N-[3-methoxy-4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 493.5 2-[6-(8-{[3-methoxy-4-(morpholin- 4-yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1H-indol-3-yl]ethan- 1-ol 485.6 (3R)-1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)piperidin-3-ol 443.8 [1-(4-{[6-(3,4-dihydro-2H-1,4- a]pyrazin-8- yl]amino}phenyl)piperidin-4- yl]methanol 457.5 (3S)-1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)imidazo[1,2- a]pyrazin-8- yl]amino}phenyl)piperidin-3-ol 443.3 00 [(2S)-4-{4-[(6-{1H-pyrrolo[3,2- b]pyridin-6-yl}imidazo[1,2- a]pyrazin-8- yl)amino]phenyl}morpholin-2- yl]methanol 442.7 01 [(2R)-4-{4-[(6-{1H-pyrrolo[3,2- b]pyridin-6-yl}imidazo[1,2- a]pyrazin-8- yl)amino]phenyl}morpholin-2- yl]methanol 442.5 02 2-[1-(4-{[6-(1H-indazol-6- yl)imidazo[1,2-a]pyrazin-8- yl]amino}phenyl)pyrrolidin-3- yl]ethan-1-ol 440.3 03 6-(1H-indazol-6-yl)-N-[4-(oxan-4- ylmethoxy)phenyl]imidazo[1,2- a]pyrazin-8-amine 441.4 04 N-[5-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)pyridin-3- yl]acetamide 430.4 05 6-(8-{[3-methoxy-4-(oxan-4- yloxy)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-2,3-dihydro-1H- indol-2-one 472.4 06 6-(1H-indol-6-yl)-N-[3-methoxy-4- (morpholin-4-yl)phenyl]-5- methylimidazo[1,2-a]pyrazin-8- amine 455.2 07 6-(1H-indol-6-yl)-5-methyl-N-[4- (morpholin-4- yl)phenyl]imidazo[1,2-a]pyrazin-8- amine 425.2 08 1-(4-{[6-(3,4-dihydro-2H-1,4- benzoxazin-6-yl)-5- methylimidazo[1,2-a]pyrazin-8- yl]amino}phenyl)-4- methylpiperidin-4-ol 471.8 09 N-[3-methoxy-4-(oxan-4- yloxy)phenyl]-6-{1H-pyrrolo[3,2- b]pyridin-6-yl}imidazo[1,2- a]pyrazin-8-amine 457.4 0 6-(1H-indazol-6-yl)-N-(4-{2-oxa-7- azaspiro[3.5]nonan-7- yl}phenyl)imidazo[1,2-a]pyrazin-8- amine 452.2 6-(1H-indazol-6-yl)-N-[3-methoxy- 4-(oxan-4- ylmethoxy)phenyl]imidazo[1,2- a]pyrazin-8-amine 471.8 1-(4-{4-[(6-{1H-pyrrolo[3,2- b]pyridin-6-yl}imidazo[1,2- a]pyrazin-8- yl)amino]phenyl}piperazin-1- yl)ethan-1-one 453.1 5-(8-{[3-(2-hydroxyethoxy)-4- (morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1-methyl-2,3- dihydro-1H-1,3-benzodiazol-2-one 502.2 [(3S)-1-{2-methoxy-4-[(6-{1H- pyrrolo[3,2-b]pyridin-6- yl}imidazo[1,2-a]pyrazin-8- yl)amino]phenyl}pyrrolidin-3- yl]methanol 456.5 5-(8-{[3-methoxy-4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-N-methylpyridin-3- amine 432.5 5-(8-{[3-methoxy-4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1-methyl-2,3- dihydro-1H-1,3-benzodiazol-2-one 472.3 5-[8-({4-[(3R)-3-hydroxypiperidin-1- yl]phenyl}amino)imidazo[1,2- a]pyrazin-6-yl]-1-methyl-2,3- dihydro-1H-1,3-benzodiazol-2-one 456.2 (3R)-1-{2-methoxy-4-[(6-{1H- pyrrolo[3,2-b]pyridin-6- yl}imidazo[1,2-a]pyrazin-8- yl)amino]phenyl)piperidin-3-ol 456.4 4-methyl-7-(8-{[4-(morpholin-4- yl)phenyl]amino}imidazo[1,2- a]pyrazin-6-yl)-1,2,3,4- tetrahydroquinoxalin-2-one 456.5 0 [(2R)-4-{2-methoxy-4-[(6-{1H- pyrrolo[3,2-b]pyridin-6- yl}imidazo[1,2-a]pyrazin-8- yl)amino]phenyl}morpholin-2- yl]methanol 472.5 (3R)-1-{4-[(6-{1H-pyrrolo[3,2- b]pyridin-6-yl}imidazo[1,2- a]pyrazin-8- yl)amino]phenyl}piperidin-3-ol 426

Example 3

Biochemical Syk Assay

(12) A generalized procedure for one standard biochemical Syk Kinase Assay that can be used to test compounds disclosed in this application is as follows.

(13) A master mix minus Syk enzyme is prepared containing 1× Cell Signaling kinase buffer (25 mM Tris-HCl, pH 7.5, 5 mM beta-glycerophosphate, 2 mM dithiothreitol, 0.1 mM Na.sub.3VO.sub.4, 10 mM MgCl.sub.2), 0.5 μM Promega PTK Biotinylated peptide substrate 1, 0.01% casein, 0.01% Triton-X100, and 0.25% glycerol. A master mix plus Syk enzyme is prepared containing 1×Cell Signaling kinase buffer, 0.5 μM PTK Biotinylated peptide substrate 1, 0.01% casein, 0.01% Triton-X100, 0.25% glycerol and 0.4 ng/well Syk enzyme. Syk enzyme is purchased from Cell Signaling Technologies, expressed in baculovirus and is an N-terminally GST-tagged full length human wildtype Syk (accession number NM-00377). The Syk protein was purified in one step using glutathione-agarose. The purity of the final protein preparation was assessed by SDS-PAGE and Coomassie staining. A solution of 200 μM ATP is prepared in water and adjusted to pH7.4 with 1N NaOH. A quantity of 1.25 μL of compounds in 5% DMSO is transferred to a 96-well 1/2 area Costar polystyrene plate Compounds are tested singly and with an 11-point dose-responsive curve (starting concentration is 10-1 μM; 1:2 dilution). A quantity of 18.75 μL of master mix minus enzyme (as a negative control) and master mix plus enzyme is transferred to appropriate wells in 96-well ½ area costar polystyrene plate. 5 μL of 200 μM ATP is added to that mixture in the 96-well ½ area Costar polystyrene plate for final ATP concentration of 40 μM. The reaction is allowed to incubate for 1 hour at room temperature. The reaction is stopped with Perkin Elmer 1× detection buffer containing 30 mM EDTA, 80 nM SA-APC, and 4 nM PT66 Ab. The plate is read using time-resolved fluorescence with a Perkin Elmer Envision using excitation filter 330 nm, emission filter 665 nm, and 2.sup.nd emission filter 615 nm. IC.sub.50 values are subsequently calculated using a linear regression algorithm.

Example 4

Ramos Cell pBLNK(Y96) Assay

(14) Another generalized procedure for a standard cellular Syk Kinase Assay that can be used to test compounds disclosed in this application is as follows.

(15) Ramos cells are serum starved at 2×10.sup.6 cells/ml in serum-free RPMI for 1 hour in an upright T175 Falcon TC flask. Cells are centrifuged (1100 rpm×5 min) and incubated at a density of 0.5×10.sup.7 cells/ml in the presence of test compound or DMSO controls for 1 hr at 37° C. Cells are then stimulated by incubating with 10 pg/ml anti-human IgM F(ab).sub.2 for 5 minutes at 37° C. Cells are pelleted, lysed in 40 ul cell lysis buffer, and mixed with Invitrogen SDS-PAGE loading buffer. 20 ul of cell lysate for each sample are subject to SDS-PAGE and western blotting with anti-phosphoBLNK(Tyr96) antibody (Cell Signaling Technology #3601) to assess Syk activity and anti-Syk antibody (BD Transduction Labs #611116) to control for total protein load in each lysate. The images are detected using fluorescent secondary detection systems and the LiCor Odyssey software.

Example 5

B-Cell Proliferation Assay

(16) A generalized procedure for a standard cellular B-cell proliferation assay that can be used to test compounds disclosed in this application is as follows.

(17) B-cells are purified from spleens of 8-16 week old Balb/c mice using a B-cell isolation kit (Miltenyi Biotech, Cat #130-090-862). Test compounds are diluted in 0.25% DMSO and incubated with 2.5×10.sup.5 purified mouse splenic B-cells for 30 min prior to addition of 10 μg/ml of an anti-mouse IgM antibody (Southern Biotechnology Associates Cat #1022-01) in a final volume of 100 μl. Following 24 hr incubation, 1 μCi .sup.3H-thymidine is added and plates are incubated an additional 36 hr prior to harvest using the manufacturer's protocol for SPA[.sup.3H] thymidine uptake assay system (Amersham Biosciences # RPNQ 0130). SPA-bead based fluorescence is counted in a microbeta counter (Wallace Triplex 1450, Perkin Elmer).

Example 6

T Cell Proliferation Assay

(18) A generalized procedure for a standard T cell proliferation assay that can be used to test compounds disclosed in this application is as follows.

(19) T cells are purified from spleens of 8-16 week old Balb/c mice using a Pan T cell isolation kit (Miltenyi Biotech, Cat #130-090-861). Test compounds are diluted in 0.25% DMSO and incubated with 2.5×10.sup.5 purified mouse splenic T cells in a final volume of 100 μl in flat clear bottom plates precoated for 90 min at 37° C. with 10 μg/ml each of anti-CD3 (BD #553057) and anti-CD28 (BD #553294) antibodies. Following 24 hr incubation, 1 μCi .sup.3H-thymidine is added and plates incubated an additional 36 hr prior to harvest using the manufacturer's protocol for SPA[.sup.3H] thymidine uptake assay system (Amersham Biosciences # RPNQ 0130). SPA-bead based fluorescence was counted in a microbeta counter (Wallace Triplex 1450, Perkin Elmer).

Example 7

CD69 Inhibition Assay

(20) A generalized procedure for a standard assay for the inhibition of B cell activity that can be used to test compounds disclosed in this application is as follows.

(21) Total mouse splenocytes are purified from spleens of 8-16 week old Balb/c mice by red blood cell lysis (BD Pharmingen #555899). Testing compounds are diluted to 0.5% DMSO and incubated with 1.25×10.sup.6 splenocytes in a final volume of 200 μl in flat clear bottom plates (Falcon 353072) for 60 min at 37° C. Cells are then stimulated with the addition of 15 μg/ml IgM (Jackson ImmunoResearch 115-006-020), and incubated for 16 hr at 37° C., 5% CO.sub.2. Following the 16 hr incubation, cells are transferred to conical bottom clear 96-well plates and pelleted by centrifugation at 1200×g×5 min. Cells are preblocked by CD16/CD32 (BD Pharmingen #553142), followed by triple staining with CD19-FITC (BD Pharmingen #553785), CD69-PE (BD Pharmingen #553237), and 7AAD (BD Pharmingen #51-68981E). Cells are sorted on a BD FACSCalibur and gated on the CD19.sup.+/7AAD.sup.− population. The levels of CD69 surface expression on the gated population is measured versus test compound concentration.

Example 8

BMMC Degranulation

(22) A generalized procedure for a standard assay for bone-marrow derived mouse mast cell (BMMC) degranulation that can be used to test compounds disclosed in this application is as follows.

(23) Bone-marrow derived mast cells were cultured for >4 weeks with IL-3 (10 ng/ml) and SCF (10 ng/ml). The cells were determined to be >90% cKit.sup.+/FceRI.sup.+ by FACS analysis at the time of use. Cells (6×10.sup.7 cells/50 ml) were serum-starved in a T150 tissue culture flask for 16 h in the absence of IL-3 and SCF containing IgEα-DNP at 1 μg/ml. Overnight sensitized cells are washed twice in Tyrodes buffer and resuspended to 5×10.sup.6 cells/ml. 5×10.sup.5 cells (100 ul) are plated in a 96 well microtiter plate (Falcon 353072) and test compounds are serially diluted to a final concentration 0.25% DMSO in the plate for 1 hr at 37° C., 5% CO.sub.2. Wells are treated with a DNP-BSA antigen challenge (50 ng/ml) and incubated for and additional 30 min at 37° C. Supernatants are assayed for hexosamimidase release versus control wells. Cell pellets are simultaneously lysed and assed for total hexosamimidase release to calculate specific release. Dose-response curves are generated using 4-parameter logistical fit and IC50s calculated.

Example 9

Passive Cutaneous Anaphylaxis (PCA)

(24) The following is a procedure for a standard PCA model used for measuring in vivo IgE anti-DNP Ab sensitization and DNP-BSA antigen for triggering mast cell degranulation and release of immune regulators that cause acute vessel permeability monitored by Evan's blue dye into the inflamed area in the mouse ear.

(25) Reagents: Anti-DNP IgE: is supplied as 1.2 mg/ml in a phosphate buffered solution with BSA for additional protein and azide for sterility. This is diluted 1:100 in sterile PBS as a 12 ug/ml working stock that can be further diluted in PBS to the appropriate concentration for injection. A further 1:5 dilution give a final 1:500 solution at 2.4 ng/ul. (10 ul/ear=24 ng). Sterile PBS alone will be used as a negative control. -DNP-BSA: will be made up at 4 mg/ml in sterile ddH.sub.2O and stored at 40° C. solution. It is further diluted 1:1 with sterile saline prior to use. This solution or a further dilution in saline is diluted 1:1 with 2% Evan's Blue in sterile saline that has been filtered though 0.02 um filter and refiltered prior to injection. For these experiments a final solution of 0.5 mg/ml of DNP-BSA in 1% Evans blue can be used. Tail vein injections will be held constant at 200 ul=100 ug in 1% Evan's Blue. —Evan's blue dye: A 2% stock in saline will be sterile filtered and diluted 1:1 with DNP-BSA saline solution for final concentration of 1% for injection.

(26) General PCA Protocol Using Intradermal Ear Sensitization

(27) 1) On d0, animals, anesthetized with isofluorine, are passively sensitized by intradermal injections of IgE anti-DNP using a 29-gauge insulin syringe. By convention, the right ear receives 10 ul intradermal injection of anti-DNP IgE while the left ear receives PBS. 2) 20 hr post sensitization, antigen challenge is administered by tail i.v. injection of DNP-BSA in 200 ul of 1% Evan's blue dye solution in saline. Tails are immersed in warm water prior to iv injection to improve success. 3) 30 minutes to 2 hr prior to this antigen challenge, drug is delivered sc or po in 10% EtOH/20% cremaphor/70% saline. 4) Animals are sacrifice by CO.sub.2 inhalation 30-60 min post antigen challenge and ears are removed for extraction of Evan's blue dye in 500 ul of formamide overnight at 65° C. 5) Blood is obtained by cardiac puncture just prior to final cervical dislocation and processed for plasma to provide PK analysis. 6) Evan's blue dye is quantified by reading absorbency of 200 ul of extracted solution in microtiter plates at 620 nm.

(28) Study Design of Experiment

(29) Each animal has one anti-DNP IgE sensitized ear (right ear by convention) and one PBS control ear (left ear by convention). Groups 1-8: represent the vehicle and compound testing arms; Group 9: represents the non-antigen negative control; Group 10: represents the non-sensitized challenged negative control; Group 11: represents the non-antigen challenged, non-sensitized negative control group (Groups 9-11 represent negative controls for background levels only and require only minimal number of animals per group.)

(30) The compounds disclosed in the examples above were tested in the Syk biochemical assay described herein (Example 3) and certain of those compounds exhibited an IC.sub.50 value less than or equal to 1 micromolar. Certain of those compounds exhibited an IC.sub.50 value less than or equal to 100 nM. Certain of those compounds exhibited an IC.sub.50 value less than or equal to 10 nM. Certain of those compounds exhibited an IC.sub.50 value less than or equal to 1 nM.

(31) Some of the compounds disclosed in Example 2 were tested in the B-cell proliferation assay (as described in Example 5) and exhibited an IC.sub.50 value less than or equal to 10 micromolar. Certain of those compounds exhibited an IC.sub.50 value less than or equal to 1 micromolar.

(32) Certain of those compounds did not inhibit T-cell proliferation and had IC.sub.50 values greater than or equal to 5 micromolar when assayed under conditions described herein (as described in Example 6).

(33) Certain compounds described herein exhibited IC.sub.50 values for inhibition of T-cell proliferation that were at least 3-fold, and in some instances 5-fold, greater than the IC.sub.50 values of those compounds for inhibition of B-cell proliferation.

(34) Some of the compounds described herein were tested in an assay for inhibition of B cell activity (under the conditions described in example 7), and exhibited an IC.sub.50 value less than or equal to 10 micromolar. Certain of those compounds exhibited an IC.sub.50 value less than or equal to 1 micromolar.

(35) Some of the compounds disclosed in described herein exhibited both biochemical and cell-based activity. For example, some of the compounds described herein exhibited an IC.sub.50 value less than or equal to 10 micromolar in the Syk biochemical assay described herein (Example 3) and an IC.sub.50 value less than or equal to 10 micromolar in at least one of the cell-based assays (other than the T-cell assay) described herein (Examples 4, 5, 7 or 8). Certain of those compounds exhibited an IC.sub.50 value less than or equal to 1 micromolar in the Syk biochemical assay described herein (Example 4) and an IC.sub.50 value less than or equal to 10 micromolar in at least one of the cell-based assays (other than the T-cell assay) described herein (Examples 4, 5, 7 or 8). Certain of those compounds exhibited an IC.sub.50 value less than or equal to 0.1 micromolar and an IC.sub.50 value less than or equal to 10 micromolar in at least one of the cell-based assays (other than the T-cell assay) described herein (Examples 4, 5, 7 or 8).

(36) While some embodiments have been shown and described, various modifications and substitutions may be made thereto without departing from the spirit and scope of the invention. For example, for claim construction purposes, it is not intended that the claims set forth hereinafter be construed in any way narrower than the literal language thereof, and it is thus not intended that exemplary embodiments from the specification be read into the claims. Accordingly, it is to be understood that the present invention has been described by way of illustration and not limitations on the scope of the claims.